Want to own a slice of Martha's Vineyard? As an owner of this studio style "Condo-tel", you will enjoy the convenience of worry free ownership. This unit has newer flooring, an updated bathroom, updated kitchenette and a cathedral ceiling. This is casual resort style living that includes association pool, 3 tennis courts, playground, and shared grilling area. This wonderful location borders Farm Neck Golf Course and lively Noman's Restaurant. This location is only a 5 minute drive from the Oak Bluffs ferry terminal and is conveniently located close to State Beach, the bus route, bike path and all that downtown Oak Bluffs has to offer. This unit is being sold furnished (wall hangings not included). The association allows for the interior decor of your choosing. A rare corner unit that even your pet can enjoy as this is a pet friendly property! The property is open to owners and guests on a seasonal basis from April - November. **Can be shown during turnovers only**

Island Inn ....tucked behind the ever-popular Noman's Restaurant. Located off the Beach Road in Oak Bluffs. Fully furnished and updated 2nd floor studio. New: floors, appliances, television, mini-split AC and two double mattresses, Fully furnished galley kitchen. Use the convenient bike path to State Beach and then further on into Edgartown ...OR a short distance north to Oak Bluffs center, ferry terminal, and all the excitement of Oak Bluffs. Gulph Creek Hotel Management handles the rentals, housekeeping and management for owners and renters. Management office on site. The expansive property includes 3 clay tennis courts, a heated community pool, barbeque areas, picnic tables and firepits, children's playground area and a community meeting room. The perfect spot to enjoy your vacation or to use the unit for investment purposes. Open April - October. TO BE SOLD FULLY FURNISHED.

Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination of a Martha’s Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular pet-friendly Noman’s, featuring outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, just minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance, making ownership easy and convenient. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM–3PM. Proof of funds required.

Welcome to 27 Island Inn, Unit 9C, an inviting Martha’s Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-bath suite accommodating up to four guests with a queen bed, sofa bed, cozy living area, well-equipped kitchenette with 2-burner cooktop, and patio/deck. Units 9C and 10C can be enjoyed separately or together through the adjoining door. Each is being offered for sale separately, with the opportunity to purchase both together—ideal for additional family, guests or expanded rental possibilities. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular and pet-friendly Noman’s, offering outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, you’re minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM–3PM. Proof of funds required.

Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha’s Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A unique feature is the adjoining door to Unit 9C, a studio with two double beds, full bath and kitchenette. Units 9C and 10C are being offered for sale separately, with the opportunity to purchase both together—perfect for extended family, guests, or expanded rental possibilities while still allowing each unit to be used independently. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular pet-friendly Noman’s, featuring outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, just minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM–3PM. Proof of funds required.

Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area partially divided by a 4' wall with two single beds, a sofa bed, 1.5 baths, and a small kitchen with a two-burner cooktop. The Island Inn is a seasonal resort community, open April–October, with beautifully maintained grounds, heated pool, three association clay tennis courts, outdoor fire pits, and easy access to downtown Oak Bluffs, beaches, restaurants, shops, ferries, golf, and boating. The popular Noman’s outdoor family restaurant is directly next door, offering dining, cocktails, lawn games, live entertainment, and a pet-friendly atmosphere. Gulph Creek Management is conveniently located on site and handles rentals, bookings, cleaning, repairs, and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM–3PM. Proof of funds required.

HERE'S YOUR CHANCE TO OWN A PIECE of the ISLAND!!! Live the beautiful Island Life with this gorgeous seasonal condo at the Island Inn Resort. AFFORDABLE & PRICED APPROX $100,000 less than an identical unit that Just Sold this summer!! Don't miss this delightful one and a half bedroom seasonal condo (sleeps 6) available for your families use. When you’re not here, the management team will rent and take care of everything for you. AMENITIES ARE AMAZING!!! There’s a beautiful pool, spacious outdoor area with lots of seating, fire pits for evening get-togethers-, play area & barbecues. Right next to the popular Noman's restaurant with outdoor music and activities- a delight for all! and Strolling distance to two ocean beaches, bike paths along w/ buses to towns. Very close to Oak Bluffs village! Come and see and I promise you-you won't want to leave!! Brokers must accompany clients.

Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails, town beaches, and ferry landings. Bring your vision, architect, and builder to create a bespoke sanctuary in one of the Vineyard's most vibrant communities.The property is limited to 1 bedroom and has no Title V bathroom limit.

Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha’s Vineyard’s most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park. This level lot includes an existing poured concrete foundation and Martha’s Vineyard Commission–approved plans by Sullivan & Associates Architects for a classic Vineyard-style, 2.5-story mixed-use building. The design includes ground-floor commercial space and two one-bedroom residential apartments, creating three rentable units in total. With plans in place and foundational work already completed, the property offers a clear path forward as a mixed-use development or, alternatively, the opportunity to construct a traditional two-bedroom residence in downtown Oak Bluffs. Some photos virtually altered for seasonality.

Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the Oak Bluffs Water Department, a 6-inch water main runs along California Avenue in front of the property. The lot is inside the Zone II district, which will require a microfast septic system (buyer to confirm). The property is being subdivided from a larger parcel, and buyers are responsible for all due diligence, including engineering, permitting, and utility installation. Additionally, an adjacent 10,000 sq. ft. lot is also available for purchase, providing the potential for a larger compound or investment opportunity.

Oak Bluffs Buildable Lot – Prime Location This flat 3-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the Oak Bluffs Water Department, a 6-inch water main runs along California Avenue in front of the property. The lot is outside the Zone II district, so a standard Title V septic system should be permissible (buyer to confirm). The property is being subdivided from a larger parcel, and buyers are responsible for all due diligence, including engineering, permitting, and utility installation. Additionally, an adjacent 15,000 sq. ft. lot is also available for purchase, providing the potential for a larger compound or investment opportunity.

GOING, GOING… GONE! This is the LAST 3-bedroom lot available in Cluster C. 12 lots SOLD 9 homes already built. Welcome to Lagoon Ridge Oak Bluffs’ newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes. The lot is ready for development with utilities at the site, including town water, electric, and a private Amphidrome wastewater system, eliminating the cost and maintenance of a traditional septic system.Lagoon Ridge borders acres of pristine conservation land with direct access to scenic biking and hiking trails, providing the perfect balance of privacy and outdoor recreation. Ideally located in Oak Bluffs and central to all down-Island towns, this vibrant neighborhood continues to grow with strong construction momentum. Easy to show contact agent for a private tour..

Charming Oak Bluffs Retreat Near Town Tucked away down a quiet lane just moments from downtown Oak Bluffs, this charming home offers the perfect blend of simplicity, comfort, and convenience. Set on just over 8,400 square feet, the property provides easy, single-story living in a sought-after Oak Bluffs neighborhood. The bright, open-concept interior features a welcoming living area and kitchen with a breakfast bar, ample storage, and a stackable washer and dryer. Two comfortable bedrooms and a full bath complete the home. Step outside and enjoy seamless indoor-outdoor living from the expansive wrap-around deck—perfect for morning coffee, afternoon lounging, or entertaining friends. After a day at the beach, rinse off in the quintessential Vineyard outdoor shower. A spacious barn-style shed provides abundant storage and could easily serve as a workshop, studio, or she-shed. Conveniently located near downtown Oak Bluffs, the Lagoon, bike path, Martha’s Vineyard Hospital, public library, and more, this adorable home is an ideal opportunity to create your own Vineyard retreat. The septic system has passed Title V inspection and is certified for two bedrooms. A charming home with plenty of potential, in a location that puts you close to it all.

OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut Avenue and Oak Avenue, increases flexibility for design options, access and privacy. Walking distance to Eastville Beach, Oak Bluffs Harbor, Oak Bluffs Library, Sunset Lake, Campground cottages, shops, restaurants, Oak Bluffs Ferry, beaches and local entertainment. This property is ideal for seasonal enjoyment, multigenerational living, or a strong rental in one of Martha’s Vineyard’s most desirable markets. A chance to acquire a ready to build lot with tons of potential, substantial bedroom capacity, options for two structures, offering long-term and enduring value & BUILDING PERMIT in place for an ADU. This could be yours! Ready to go.

Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to the beach, town, bike path, and more, this home sits in a special location. Enjoy this house as it is or work through the process to create something new. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but not on the MACRIS registry. Buyers should research the process for making major renovations.

In-Town Oak Bluffs Condo with Panoramic Water Views Experience the best of island living in this charming in-town Oak Bluffs condo, offering just under 800 square feet of comfortable and versatile living space. The condo features one generously sized bedroom plus a separate sleep nook, offering flexibility for guests, a home office, or additional sleeping accommodations. The nook could potentially be configured as a second bedroom, subject to applicable requirements and approvals. A true highlight is the rooftop deck shared with just one other unit (# 4 also for Sale). This exceptional outdoor space provides panoramic water views across Nantucket Sound and Oak Bluffs Harbor, creating a spectacular setting for morning coffee, afternoon relaxation, or enjoying the beautiful island sunsets. Ideally situated in the heart of Oak Bluffs, this property places you within easy reach of the harbor, beaches, restaurants, shops, and the vibrant energy of Oak Bluffs center. Whether you're seeking a Martha’s Vineyard getaway, investment opportunity, or your own in-town retreat, this condo offers an appealing combination of location, flexibility, and breathtaking water views. A special island property with the convenience of in-town living and a rooftop view that truly sets it apart.

Located in a desirable waterfront community, this newly painted end-unit condo offers 1 bedroom plus a versatile loft and 1.5 bathrooms, combining comfort with easy, low-maintenance ownership. Residents enjoy a community dock, pond access, kayak storage, boat launch, a clubhouse, and tennis courts. This year-round home is filled with natural light and features a spacious deck —perfect for relaxing or entertaining. Additional highlights include in-unit laundry, dedicated parking, a storage area, a new septic system (2025), and low HOA fees. Ideally located near Farm Neck Golf Club, Felix Neck Wildlife Sanctuary, scenic bike paths, and the down-island towns, this inviting property offers the best of coastal living.

Build Your Dream Home. Close to town and all that Oak Bluffs has to offer, Roger’s Way is a small enclave offering a wonderful opportunity to create your own Vineyard retreat. A paved road leads to 15 Roger’s Way, one of the last remaining lots in this desirable neighborhood. A three-bedroom septic system is already installed, and electric access is available at the edge of the property. Bring your vision and create your Vineyard dream home.

Intown Oak Bluffs Condo with Panoramic Rooftop Views Discover the charm of island living in this exceptional 2-bedroom, 1-bath condo in the heart of Oak Bluffs. Just under 1,000 square feet, this comfortable residence combines character, comfort, and an unbeatable in-town location. Step inside to an inviting custom wood interior that gives the home a distinctive coastal-island feel. Thoughtfully designed spaces provide the perfect setting for relaxing after a day at the beach, enjoying morning coffee, or entertaining family and friends. One of the condo’s true highlights is the semi-private rooftop deck, shared exclusively with Unit 5 (Also for Sale). This extraordinary outdoor space offers a breathtaking panoramic view of the Atlantic Ocean, Nantucket Sound, and Oak Bluffs Harbor — an incredible vantage point for morning sunrises, afternoon breezes, and spectacular island sunsets. Located within easy reach of the best of Oak Bluffs, you can stroll to the harbor, beaches, restaurants, shops, and all the vibrant energy that makes this beloved Martha’s Vineyard village so special. A rare opportunity to own a distinctive island retreat with exceptional rooftop views in the heart of Oak Bluffs.

Welcome to this FULLY FURNISHED, private, 2-bedroom, end-unit townhouse offering 1,208 sq ft of effortless coastal living. With seasonal rentals already in place this opportunity is the defenition of TURN KEY. Thoughtfully designed with both comfort and style in mind, this coastal retreat blends relaxed island charm with modern convenience—perfect for year-round living or as an established rental investment. Sunlight pours in through two walls of sliding glass doors, opening to an expansive 288 sq ft private deck. Ideal for al fresco dining, morning coffee, or evening gatherings, this inviting outdoor space creates a seamless indoor-outdoor lifestyle. The half bathroom, along with the added convenience of first-floor laundry complete the first floor. Upstairs you will find two generously sized bedrooms with lofted ceilings, beautiful patio views and a full bath. If simplicity is what you’re craving in your island home, this condo offers a low-maintenance lifestyle with community services such as trash removal and snow clearing—so you can spend more time enjoying the island and less time managing it. Located within the sought-after Sengekontacket community, residents enjoy an array of amenities including a saltwater dock with kayak and canoe storage, a freshwater pond with clubhouse, tennis and pickleball courts, and a playground area. Centrally positioned, the property offers easy access to downtown Oak Bluffs, Farm Neck Golf Club, pristine public beaches, and the island’s scenic bike paths—placing the very best of island living right at your doorstep. Additional conveniences include a two-car carport and a private owner storage closet. A refined island escape with strong investment potential—this is coastal living at its best. More information about the Sengekontacket Community can be found at: https://www.sengekontacket.com/

A Gem of a Marthas Vineyard Camp Meeting House Association Home, 3 Dukes County Ave. Located down from the Oak Bluffs Harbor. A couple house from Sunset Pond. Convenient to Beaches,Harbor, Resturants, Shopping, Dancing Music and walk to and from the Steamship Authority. 2 bedroom,1 queen bedroom 1 full bed and twin bunk room with built in wardrobe and desk bathroom. Bathroom shower bath combo cast iron tub, sink and toilet, Kitchen gally stone and marble counter top with a 2 seat breakfeast nock. vintage wood cabinets, living room with wood burning fireplace. and access to small attic storage space. attach bunk laundry room with washer and dryer brand New hotter on demand 2025. Town hook up to septic 2015 with update electric and isulation for yearround living. Back outside shower tub and sink all with hot and cold runnning water. lots of yard space front sides and back for your privacy. lots of on site parking. beautiful Lawn, lots of trim replace with axec trim. can be purchased with furnishings if needed. a very private campground house with water shed on one side and parking lot on the other and front side. Come make this beauty your own. Being sold as is

Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process. The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development. Subject to the Town of Oak Bluffs' zoning regulations and permitting requirements, the property offers the potential for a main residence and a guest house, with a combined maximum of six bedrooms. Whether you're envisioning a year-round residence, a seasonal getaway, or an investment property, this parcel presents an outstanding opportunity to build in one of Martha's Vineyard's most sought-after communities.

Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs. Build Your Martha’s Vineyard Dream Home. Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha’s Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a possible future pool. Located in the sought-after Eastville area, where many homes enjoy beautiful water views, this lot offers the potential to capture stunning views of Vineyard Sound and beyond from a thoughtfully designed home. Create a custom residence that embraces all the beauty and lifestyle Martha’s Vineyard has to offer. Enjoy a short walk to Eastville Beach, where you can take in spectacular sunsets, watch the ferries come and go, and experience the charm of island living. Just a short drive away, you’ll have access to everything that makes Oak Bluffs so special — additional beaches, shellfishing, swimming, boating, and the vibrant energy of Circuit Avenue, featuring boutique shopping, diverse restaurants, and convenient ferry service to and from the island via the iconic Oak Bluffs Harbor and nearby ports. This is more than just land — it’s an opportunity to create something truly special. Don’t just dream it — make it reality. Owning a piece of Martha’s Vineyard is an investment in a lifestyle you’ll never regret. Please include a pre approval or proof of funds with offer. Seller is offering a buyers broker consideration.

Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you’ll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha’s Vineyard so special. Martha’s Vineyard Hospital is also just a short two-minute drive away. Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The roof is approximately 10 years old, and recent improvements have focused primarily on the basement, where the space has been transformed to expand the home’s usable living and recreational area. Whether you envision a TV room, game room, home office, exercise area, or a combination of uses, there are plenty of possibilities. A newly completed “doghouse”-style exterior basement entry provides convenient direct access to the lower level. The first and second floors would benefit from a little TLC and personal touches to brighten and refresh the space, providing a great opportunity for the next owner to make the home their own. Outside, the property offers a small, manageable yard with off-street parking, along with a classic Vineyard outdoor shower—a favorite feature after a day at the beach and something many consider a must-have for Island living. Set on a 5,000-square-foot lot, the property offers the best of both worlds—a quieter location at the Eastville side of Winemack Street while still being just minutes from downtown Oak Bluffs. Title 5 System failed, Seller is offering a credit at closing to help with costs(to be determined). Prequalification letter from your lending source or proof of funds required. Owner and tenants currently occupy the home; 24-hour notice for showings is preferred.

This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment. The home features a bright, open-concept kitchen, dining, and living area with beautiful hardwood floors that create a warm and inviting atmosphere. A first-floor den, complete with a daybed, while a full bathroom on the main level adds convenience. Sliding glass doors from the dining area open to a spacious deck overlooking the beautifully landscaped gardens, creating the perfect setting for outdoor dining, entertaining, or simply relaxing. Additional outdoor amenities include a hot tub and an outdoor shower, allowing you to fully enjoy the Vineyard lifestyle. Upstairs, you'll find a spacious primary bedroom, a large open loft that can serve as an additional living area, and a second full bathroom. Adding even more value, the home is equipped with transferable solar panels, providing energy efficiency and long-term savings for the new owner. The location is hard to beat. The property is within walking distance of Farm Neck Golf Club, the scenic Trade Winds Preserve Land Bank walking trails just across the street,

Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a separate utility room. Recent upgrades includes new roofs, new electrical service in front house, and a new 3-bedroom title 5 septic system.

Create an extraordinary Martha's Vineyard estate in the exclusive Lagoon Ridge community of Oak Bluffs. This mostly wooded estate parcel of over one acre features gently rolling topography, providing an exceptional canvas for a custom-designed luxury residence. Privately situated within an intimate enclave of just four estate parcels, the property is accessed by a welcoming paved approach. This thoughtfully planned neighborhood will feature distinctive architect-designed residences, creating a refined and cohesive community setting. Approved for connection to the neighborhood's private Amphidrome® (you will avoid the high expense of a septic system a savings of almost $50,000)on-site wastewater treatment system the parcel is approved for a three-bedroom residence and may offer the potential for additional flex spaces, expansive outdoor living areas, a pool, and attached or detached garages, subject to applicable approvals. Embrace the timeless Martha's Vineyard coastal lifestyle, with beaches, boating, children's sailing programs, the harbor, ferries, boutique shopping, restaurants, and the charm of Oak Bluffs just minutes away. This exceptional offering presents a rare opportunity to create a private Island retreat in one of Oak Bluffs' most desirable neighborhoods. Buyers are encouraged to conduct their own due diligence regarding building plans and intended use.

Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back deck. The second floor has a huge front-to-back primary bedroom, a large landing, full bathroom and two guest bedrooms. Although the property is in need of updates, it will be well worth the effort. There is a ton of potential here. Being offer "as is".

Lovely residential lot with a rural feel. Conforming 1.397 acre wooded lot in R3 with 150ft frontage on County Rd very close to the entrance to Meadow View Farm. Residential with bike path access along County Rd. Has been surveyed, staked & tagged. Town water available along County Rd. Electric access box will need to be installed. Number of bedrooms allowed is more than 7 bedrooms. This is dependent on an approved septic design for what an new owner would like to build. Drone photos coming......

Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure year-round storage. Conveniently located near Farm Neck Golf Club, downtown Oak Bluffs, and more. Easy access to all island destinations via County Road and Barnes Road. Perfect blend of practicality and charm for seasonal or year-round use. Flexible leasing, partnership, or investment opportunities available.

Charming Oak Bluffs Ranch on a Peaceful Cul-de-Sac Welcome to this inviting 3-bedroom, 1.5-bath ranch-style home nestled on a generous .35-acre lot at the end of a peaceful cul-de-sac in Oak Bluffs, Massachusetts. Ideally located near the beach and town center, this property offers a wonderful blend of privacy, convenience, and classic island living. The comfortable single-level layout features three bedrooms and one-and-a-half baths, offering plenty of space for family, guests, or a relaxing Martha’s Vineyard getaway. Step outside onto the sunny deck, an ideal spot for morning coffee, outdoor dining, or unwinding after a day at the beach. The lovely, spacious yard provides plenty of room for outdoor enjoyment, while the storage shed is perfect for beach equipment, bicycles, gardening tools, and seasonal belongings. Set on a quiet cul-de-sac with a desirable .35-acre lot, this home combines the tranquility of a residential setting with the convenience of being close to Oak Bluffs beaches, restaurants, shops, and the town center. A wonderful opportunity to create your own island retreat in one of Martha’s Vineyard’s most beloved communities.

Stylish, thoughtfully designed ranch style home built in 2014 is bright and sunny. Tucked away in a private tranquil setting just a stroll to downtown, harbor, beaches, ferries, library, restaurants and shops, the home features solar panels, large living room with separate dining area, kitchen with stainless steel appliances, 3 bedrooms, 2 full baths with tiled floors, and laundry room. Completing the home is a large rear deck, irrigation system, and a walkout basement that would make a great bonus room, family room or home office. Parking in driveway, plus second parking area off cul-de-sac. Perfect for year-round or summer vacation/rental home.

Surprisingly roomy Cape-style home, centrally located in Oak Bluffs and right across from the bike path. This five-bedroom house offers generously scaled living spaces throughout, including a large living room filled with natural light, an open stairway, a spacious dining room, and an updated kitchen. The first floor features a primary bedroom, a full bath with laundry, and a separate mudroom/back entry. Recent updates include a new kitchen with new appliances, new baths, fresh interior and exterior paint, new lighting, and new flooring and carpet throughout.

New listing tucked away on a dead end road in Oak Bluffs ~Enjoy the best of Vineyard living from this beautifully renovated Oak Bluffs home, ideally located just a short walk from a private Lagoon beach—perfect for swimming, kayaking, paddleboarding and all your favorite water activities. The inviting living area features a dramatic vaulted ceiling and gas fireplace, creating a warm and spacious gathering space. The thoughtfully designed layout offers a private first-floor primary suite, while the second floor features two additional spacious bedrooms and a full bath. Step outside to a spacious back deck, ideal for outdoor dining, entertaining or relaxing after a day at the beach. Beautifully updated for today’s lifestyle, this home offers a wonderful blend of comfort, coastal living and Vineyard charm.

Renovated Cape style home in the desirable East Chop neighborhood of Oak Bluffs, offering the perfect combination of coastal charm, modern updates and an exceptional location. This bright and inviting 3-bedroom, 2-bath home features a spacious open floor plan, coastal-inspired décor throughout, and comfortable spaces designed for relaxed Vineyard living and entertaining. A first-floor bedroom provides added flexibility, while the enclosed 120-square-foot sun porch creates a wonderful extension of the living space. Outdoor living shines with a newer mahogany outdoor shower, bluestone patio and beautifully designed walkway, all surrounded by a private setting. An unfinished basement provides approximately 720 square feet of additional space for storage and future possibilities. Walk or bike to Jetty Beach and the East Chop Lighthouse, enjoy the nearby East Chop Beach Club, or stroll to Oak Bluffs Harbor, downtown restaurants and shops. With a proven rental history and a desirable East Chop location, this move-in-ready property is equally suited as a Vineyard retreat, year-round home or investment opportunity. Please include a pre approval letter with all offers and or proof of funds for cash.

Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style. First showings 7/12/26.

Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style. First showings 7/12/26.

Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an expansive screened porch — ideal for entertaining on warm summer evenings. A welcoming front porch provides additional outdoor living space. The main level is completed by a gracious primary suite with a full bath and a convenient half bath. The walk-out lower level features two additional bedrooms, a full bath, and laundry. A one-car garage offers excellent storage for your car, kayaks, or beach gear. Perfectly positioned between Edgartown and Oak Bluffs. **Additional bedrooms possible with septic upgrade per BOH.

Incredible opportunity for workforce housing, live in one/rent the other, or multi generational family living. Main house has 4 levels of living space. Main floor living/kitchen/dining/full bath and laundry. 2nd floor has two bedrooms and full bath. 3rd floor is a large finished bonus room. The full walkout basement in the main house is finished with private entry, full bath, separate rooms and laundry. The guest house was completely renovated top to bottom in 2023, new everything! Included but not limited to: new kitchen, baths, windows, roof, siding, electrical and plumbing. Landscape around guest house has new stone walls, patio, and pea stone driveway. Guest house is 1 bedroom, 1.5 bath and really is a gem. Main house has been fully rented year-round for years and may need a little TLC for the next owner, a new asphalt roof on main house was installed in 2025. Guest house has been rented via airbnb and has all 5 star reviews. A new septic system was installed in 2018. This property has TONS of potential.

Nestled in this desirable Hidden Cove community, this contemporary residence offers a quintessential retreat centered on outdoor recreation and coastal living. Residents enjoy premier neighborhood amenities, including direct water access to Sengekontacket Pond for seamless kayaking and paddleboarding, as well as community tennis courts just steps from your front door. Set on a private, wooded lot, the home showcases cedar siding, a striking wood burning fireplace, gas fireplace, an expansive wood deck, screened porch and outdoor shower for effortless post-beach relaxation. Featuring a 512 square foot finished lower level not counted in the square footage, ideal for a media room, gym and/or home office, this property perfectly combines island tranquility with an active coastal lifestyle.

Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features Victorian charm, featuring a beautiful stained glass window, painted beam ceilings, wainscoting, and built-in shelves. The second floor has 3 bedrooms, each with its own character, including a generous primary bedroom suite with vaulted ceilings, skylights, a walk-in closet, plus a full bathroom and an extra built-in closet. The 2nd bedroom has an open and airy feel with a vaulted ceiling and a screened porch affording views of the neighborhood. The final room has its own private balcony for viewing the backyard garden oasis. The lower level consists of a finished bonus room, laundry, and a full bathroom with tub and storage area. This home and its established gardens have been lovingly maintained, and its location in a delightful neighborhood of highly sought-after East Chop, gives you all that Martha's Vineyard living can offer. Passed Title V Inspection.

Wake up to breathtaking ocean views and the soothing rhythm of waves from this charming two-bedroom oceanfront cottage on East Chop. Set on approximately .21 acres of waterfront property with more than 50 feet of shoreline, this special retreat offers a rare opportunity to own a true piece of the island's coastline. Positioned directly on the water, the cottage captures the beauty of the ever-changing ocean from sunrise through sunset. Inside, the cozy two-bedroom cottage offers an inviting island escape with an intimate connection to its spectacular surroundings. Step outside and experience the salt air, gentle sea breezes, and the unmistakable magic of waterfront living. Whether you're enjoying your morning coffee while watching the boats pass, gathering with family and friends, or simply listening to the waves from your own waterfront property, this is a place designed to create lasting Martha's Vineyard memories. A rare East Chop opportunity—over 50 feet of oceanfront, .21 acres of waterfront land, and an enchanting two-bedroom cottage in an extraordinary setting. Just imagine what you could build with proper permitting on this special lot.

Welcome to this sun-drenched, reverse contemporary-style home located in the lovely Meadow View Farms community! This multi-level home has boundless potential. The second level features a bright, open floor plan with cathedral ceilings, living, dining, and kitchen areas, and 3 sliding doors that take you outside to the upper deck. Open the sliders to the expansive deck and you will almost double the living space on the upper level. There is also a powder room on the upper level. The main floor features the primary suite with bath, walk-in closet, air conditioning, and sliders that open to the first-floor deck; that level offers 2 more spacious bedrooms and a shared bath. Venture downstairs to the above-grade lower level and enjoy the family room, reading nook, and bonus room. There is also a large storage/utility room with a second powder room. Like every true island home, there is an outdoor shower. Plenty of additional storage is under the deck. Solar panels were added in the fall of 2023. With 3 floors of living space and an expansive portion of the land behind it, this property offers so much potential for the next owners. Meadow View Farms Association is a neighborhood less than 2 miles from downtown Oak Bluffs featuring paved roads, tennis courts, and pastoral meadow views. Strong year-round rental history! The home is being sold "as is".

Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers just over 2,800 square feet of living space, plus an additional 700+ square feet of newly finished recreation space above the two-car garage, with its own private entrance and second-floor deck. The inviting first floor is designed for both comfortable living and entertaining, featuring a spacious kitchen with a center island and abundant counter space. The adjacent dining room offers a warm gathering space with a wood stove, while glass doors open to a wood deck and bluestone patio for seamless indoor-outdoor living. Multiple sitting areas, a living room with a gas fireplace, and a private office provide plenty of space to relax or work. Upstairs, two guest bedrooms share a recently updated bathroom, while the spacious primary suite offers a walk-in closet and a large, light-filled bathroom with a soaking tub and tiled shower. The primary bedroom and bathroom feature radiant-heated floors, adding an extra level of comfort and warmth. Additional amenities include a two-car garage and half basketball court, making this a versatile home with plenty of space for guests and entertaining. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this property offers an ideal setting for enjoying all that the Island has to offer.

Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property includes a newly beautifully renovated 2 bedroom 2 bathroom guest house. This guest house is offered fully furnished. This listing documents include a custom landscape design plan. This very large parcel of land is well suited to get started building an investor dream or family compound.

Your opportunity in Sengekontacket! Being sold turnkey. This modern home has four bedrooms and three full baths. Large windows and high vaulted ceilings, the home lets in bright natural light. The first floor has three bedrooms and a full bath with double sinks. Beautiful oak and maple floors complement the cherry stairs and living room built-ins. Open concept second level contains the kitchen, living room and dining room. The primary en suite includes full private bath with Jacuzzi tub and shower, walk-in closet and dressing area. Three sliders lead onto a large sunny deck from the living area, great for alfresco dining, lounging or entertaining, extending your living space. The fourth slider accesses the deck from the primary bedroom. The full finished basement has eighteen foot high ceilings, multiple windows and glass back door. The basement also includes a third full bath and utility room. This surprising basement would make a fantastic recreation, media room, playroom, dance studio, or home office. This home is being sold in "as is" condition. Located in a private community with wonderful amenities such as tennis, pickleball, mail delivery, freshwater pond, clubhouse, and kayak storage with access to a salt water dock and boat landing. Potential for a boat mooring via the Oak Bluffs Harbormaster. This is a great central Island location near Farm Neck Golf Club, with easy access to all island Towns, shopping, beaches, restaurants and entertainment.

Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities--ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath. Sliding doors open to a deck and patio with manicured lawn. Moments to downtown, beaches and ferries.

An exceptional offering—the final homesite available within The Preserve at The Woodlands, one of Oak Bluffs’ most coveted residential enclaves. Create a custom coastal retreat in an extraordinary setting where architecturally designed residences, protected conservation land, and the timeless beauty of Martha’s Vineyard converge. This 1.87-acre homesite represents the final opportunity to build within this exclusive community, offering underground utilities, town water, and Board of Health approval for up to six bedrooms. Enjoy a peaceful and private setting with direct access to conservation land and miles of scenic walking and biking trails. Ideally located just minutes from downtown Oak Bluffs, pristine beaches, Oak Bluffs Harbor, ferry terminals, and Farm Neck Golf Club, this exceptional property offers an unparalleled blend of privacy, convenience, and enduring value. Whether envisioning a year-round residence or a seasonal Island retreat, this is the opportunity to create a legacy property in one of Martha’s Vineyard’s most sought-after communities.. Easy to Show ! Call Agent for a tour!

East Chop colonial style 2BR/2BA year-round home on East Chop PLUS a separate buildable lot behind the house. The house at 51 Winemack St has a 2-bedroom Title V septic that recently passed inspection, full basement, electric baseboard heat and large yard that allows for expansion potential of the house. Recent improvements include new roof, new shingle siding, and painted trim. The property is conveniently located near the East Chop tennis courts, beach club and public beaches, downtown, the harbor, ferries to the mainland, restaurants and shops. Perfect for year-round or summer vacation rental. The property includes a separately deeded buildable lot (10,246 sq ft) behind the house where the recent perc test indicates that it is suitable for an ADU or a home, and potentially able to support 4-6 bedrooms (but please confirm with appropriate town departments). Access to the lot from Winemack St. is off the paper road Meadow Ave which has recently been approved for opening. Note: Assessed value and estimated taxes shown are for both properties combined. The properties are ideal for a family compound, rental potential and builders.

Location, location, location: This 1999 home with all the comforts of the 21 st Century is nestled on a landscaped lot within mellow surroundings. And yet … it’s located within mere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and a Land Bank trail. The situation hardly gets better. The 3BR/2.5BA house features a deep wraparound farmer’s porch, Brazilian cherry floors, an open and flexible layout, recent kitchen and bath updates, a generous 2nd floor bonus room and an attached single-car garage. The poured basement stands ready for your finishing whims. Kick back in your sunny backyard or on your shady porch with the distant peek of Nantucket Sound. Songbirds will serenade you from towering maples and oaks. Pinkletinks will chime in from Farm Pond. It’s no wonder that this abode has been loved – by vacation tenants as well as the owner. Note: This property lies within the jurisdiction of the Cottage City Historic District and Copeland District of the Town of Oak Bluffs. Passed Title 5.

Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer’s porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined by soaring cathedral ceilings, rich hardwood floors, and a striking hand-cut stone propane fireplace that anchors the open-concept living spaces. The well-appointed kitchen with casual dining area flows seamlessly into a formal dining room and an inviting living room, creating an ideal layout for both everyday living and entertaining. A spacious mudroom offers practicality and convenience after beach days or inclement weather. The primary suite is privately situated on the first floor and features abundant natural light from a bay window overlooking the backyard, a walk-in closet, and an oversized bath complete with skylights and an additional bay window. The first floor features another comfortable sized bedroom conveniently located across the hall from the Primary Suite. The second level features two generously sized and identical ensuite bedrooms, each offering shower/tub combinations and dual closets for exceptional storage. The partially finished lower level offers an additional 1,957 square feet, presenting remarkable opportunities for customization or expansion. The oversized two-car garage is complemented by approximately 576 square feet of space above, ideal for potential guest accommodations, an ADU, studio space, or a private office. Approvals from the Town are required. Meadow View Farms is known for its convenient and quiet setting, close proximity to the bike path, Farm Neck Golf Club, and more than 200 acres of nearby conservation land with extensive trails. Title V inspection has passed and approved for 5-bedrooms. Owner is currently in residence.Please allow a minimum of 24 hours' notice for all showings. *Buyer Agent must be present at all buyer client showings, inspections and walkthroughs unless otherwise agreed to in advance by the listing agent. ** Some images have been virtually enhanced or AI-generated for illustrative and marketing purposes. Images may not represent the property’s actual appearance, finishes, furnishings, or condition.

Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the street, bordered by the Land Bank property of Dougs Preserve. Together a combined total of just over an acre of land. Included is Deeded Access, via a boardwalk to Brush Pond, with more wonderful views. Directly in front of the property lies a sandy beach where a sandy shoreline meet calm, inviting, Lagoon waters. After a day at the beach, rinse off in the beautifully constructed mahogany outdoor shower, an elegant Vineyard touch. The home is equipped with central air conditioning, a full basement, wood and tile floors throughout, updated insulation, and irrigation. Located just minutes from the vibrant centers of Oak Bluffs and Vineyard Haven, as well as their respective Ferry terminals, minutes to Eastville Beach, easy access to stores, restaurants, Farm Neck Golf, Mink Meadows Golf & a host of activities. This property offers both tranquility and convenience in one of Martha’s Vineyard’s most desirable water view settings. An 'Up Island' feeling with a 'Down Island' location. Contents available for purchase separately. Excellent Rental History.

East Chop with Water View! The perfect size vacation house or year round living, with all the bells and whistles, water views and located in the most desired neighborhood on East Chop! Designed by Hutker Architects, built with high quality craftsmanship by J.G. Early and landscape design by Dan Gordon Landscape Architects. This recently completed cozy 2BR/2.5 BA with solar panels providing remarkable results in energy efficiency and cost savings, includes an electric car charging station in the garage with the option to move to either side, landscaped yard and is conveniently located near the East Chop beach club, tennis courts and yacht club, downtown, the harbor, ferries, restaurants and shops. With construction completed in 2024 the property is virtually new. This comfortable year-round home includes an open floor plan with living room, a propane log fireplace, kitchen with countertop seating, a classic dining booth, a mudroom with washer & dryer, and powder room on the 1st floor. The second floor includes primary en-suite bedroom with balcony overlooking the Vineyard Sound, plus a second bedroom with expandable 1/2 bath and small study/studio space. Ample parking in driveway for several cars. Ideal for year-round use, vacation rentals or guests. Seller requests occupancy through mid June of 2027, early closing preferred and will rent back.

Tucked away in a serene setting and set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space with plenty of room for a backyard pool. The main portion of the house includes a gourmet kitchen, multiple entertaining areas including living room, family room, game room, a screened porch, ensuite bedroom and powder room. An attached one-bedroom guest apartment above the garage includes new kitchen, bedroom, living room, washer/dryer and mini-split heat/AC. Recent improvements outlined in the documents section. It's seamless floor plan is great for entertaining and flows family and guests from an oversized living room with fireplace to the dining room, gourmet kitchen and an inviting family room with cathedral ceiling and propane stove. The 2nd floor includes two large bedrooms (one ensuite), a second full bathroom and new washer/dryer. To the side of the garage is a large separate bonus/variable use room with heat/AC that could be used as an office or game/family room. Property includes a spacious rear patio and deck with access off both the kitchen and screened in porch, as well as an outdoor shower and parking for several cars in the driveway. The lot is large enough in this R3 zone for an in-ground pool. Assessed value does not reflect extensive 2026 renovations. Title V septic passed inspection 5/12/25 and in-ground propane tank pressured tested in 2025.

Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood floors that create an airy, light-filled atmosphere. Designed for relaxed coastal living, this partially insulated retreat offers effortless indoor-outdoor flow and functional updates throughout. Enjoy an unbeatable location directly across the street from the neighborhood playground and just a short, scenic walk to pristine beaches, local dining, and the ferry terminal. Whether you are seeking a summer sanctuary or an investment property, this home delivers classic island living at its best! Showings on Saturdays 1-3pm only beginning on August 1.

LARGE PRICE DROP. THIS IS A PERFECT LOCATION FOR WEDDING PARTIES. Just steps from the beach and minutes to both Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal retreat offers an exceptional location paired with a strong, proven rental history. Set on an oversized lot just two parcels from the shoreline, the home features six bedrooms and four bathrooms, providing generous accommodations for family, friends, and guests. From the EXPANSIVE ROOFTOP entertainment deck, enjoy sweeping 180-degree water views of Vineyard Haven Harbor — a spectacular vantage point for watching ferries and sailboats glide by at sunset. Originally built in 1859 by noted whaling captain Shaw Norris, this classic Greek Revival residence seamlessly blends historic character with modern luxury. Extensive renovations — including a new roof, siding, trim, and all-new mechanical systems — have transformed the property into a home that lives like new construction while preserving its architectural integrity, ensuring peace of mind for years to come. The open-concept first floor is thoughtfully designed for effortless entertaining, anchored by a gourmet kitchen that flows seamlessly to a private outdoor dining area. Two first-floor ensuite bedrooms provide exceptional flexibility: one showcasing original architectural details and a historic hearth, the other offering a private entrance and a secluded patio porch. Upstairs, a comfortable lounge opens to a spacious recreation area, creating the ideal setting for gathering and relaxation. Land Bank–protected parcels on two sides of the property enhance privacy and preserve the serene coastal setting. Whether you’re seeking a high-performing investment property or a generational family compound, this one-of-a-kind residence offers timeless charm, breathtaking water views, and modern comfort in a premier Martha's Vineyard location. Broker has an ownership interest in the property.

NEW CONSTRUCTION IN OAK BLUFFS WITH VINEYARD HAVEN HARBOR VIEWS Currently under construction and anticipated to be completed in Fall 2026, this thoughtfully designed four-bedroom, three-and-one-half-bath home pairs contemporary comfort with classic Vineyard character. Offering approximately 2,363 square feet of finished living space, the home features cedar-shingle siding, black United windows, oak hardwood flooring, and an open, light-filled floor plan. The main level centers around a spacious kitchen, dining, and living area designed for gathering and entertaining. The kitchen will feature Shaker-style cabinetry, quartz countertops, a generous center island, and a Bosch appliance package. A first-floor bedroom and full bath provide flexibility for guests, while a study offers additional space for work or relaxation. Upstairs are three additional bedrooms, including a spacious primary suite with a large closet and private bath, two guest bedrooms, an additional full bath, second-floor laundry, and a separate TV den. Carefully selected bathroom finishes incorporate ceramic and marble-look tile, quartz surfaces, and glass shower enclosures. Heating and cooling are provided by a multi-split heat-pump system with discreet ceiling cassette units. Outdoor living is a highlight, with a welcoming front porch, second-floor deck and an expansive rooftop sunset deck offering views toward Vineyard Haven Harbor—an exceptional setting for taking in Island sunsets. An approximately 1,200-square-foot unfinished basement provides substantial additional space and future possibilities. The property will also include off-street driveway parking. A rare opportunity to purchase a newly constructed Oak Bluffs home while construction is underway and look forward to enjoying a brand-new Island residence upon completion. Plans, specifications, finishes, dimensions, and completion date are subject to change during construction. Renderings, if shown, are for illustrative purposes only. Property is currently assessed as land; assessment and real estate taxes are subject to change following completion and reassessment. See rendered video walkthrough here: https://youtu.be/7vnLq1e9-4o

WATERFRONT WITH DOCK – Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock, offering direct access for boating, swimming, paddle boarding, or simply relaxing by the water's edge. A truly special legacy property offered for the first time in over 50 years where history, charm, and an unparalleled waterfront lifestyle come together.

Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home’s original charm. Tucked privately at the rear of the property, the guest cottage offers a peaceful retreat ideal for hosting family and friends or creating a flexible living space. Located in the heart of East Chop, a close-knit and distinguished community, this property is just moments from beaches, the lively harbor, and the vibrant shops and restaurants of downtown Oak Bluffs.

Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built residence offers the perfect blend of sophistication and refined Vineyard style. The spacious floor plan offers over 3,200 square feet of living space, highlighted by a first-floor primary suite, an open-concept great room with high ceilings and oversized windows, gourmet kitchen with pantry, dining area, mud room with laundry and seamless indoor-outdoor living. A screened porch and covered porch are perfect for summer entertaining and relaxed evenings after a day at the beach. The second floor features two additional bedroom suites, a loft-style gathering area or office, dedicated laundry, and a flexible bonus space ideal for media room, fitness space or office. An attached two-car garage provides ample storage for vehicles, bikes, and beach gear. Crafted with high-end materials and attention to detail, this is a terrific opportunity to own a custom, to-be-built home in vibrant Oak Bluffs. Enjoy easy access to beaches, sailing, golf, restaurants, shops, ferry ports, and all the attractions that make the Vineyard a premier vacation destination.

This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor includes a private guest bedroom with its own bath, while the second floor offers two additional guest bedrooms and a generous primary suite with access to a large deck. These rooms share two well-appointed bathrooms. With dual road access, thoughtfully landscaped grounds, and a versatile garage space, this home provides both comfort and flexibility in a prime location.

A Victorian Grand Dame overlooking Ocean Park -- in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ferries, the Campground and the Tabernacle. This treasured property has been home to family and guests that have enjoyed dramatic sunsets, spectacular August fireworks and evening strolls to town for generations. This historic home retains its Victorian character while having been carefully maintained and updated over the years. Recent improvements include a Title V septic, all new windows, ducted mini-splits for heat/AC throughout the house plus two propane monitors and outdoor shower. Lastly, there is parking for three cars in the parking area behind the house -- a big plus in the heart of downtown.

Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres of beautifully maintained grounds, the 4,046-square-foot residence offers generous, light-filled spaces designed to capture the water views from nearly every room. From the moment you enter, the Lagoon is a constant presence, with expansive views enjoyed from the main living spaces, bedrooms, decks, and outdoor areas. The main level features soaring ceilings, a wood-burning fireplace, wet bar, multiple seating areas, and an eat-in kitchen opening to a sunny patio. A separate two-room wing with full bath and private deck provides flexible space for an office, den, studio, or guest accommodations. Upstairs, the primary suite features a fireplace, walk-in closets, en-suite bath, and private deck overlooking the Lagoon. Two additional en-suite bedrooms open to a wraparound deck and 3-season porch. The newly refinished 2,000-square-foot walk-out lower level includes a full bath, laundry, and space for a gym, media room, or additional living area. Offered fully furnished, the home is ready to enjoy. With its small sandy beach, protected waterfront, and easy access for swimming, kayaking, boating, and clamming, this property is built for connection and memory-making. Whether you are hosting a full house or savoring a quiet weekend, the Lagoon becomes your backdrop: sunrise coffees, afternoon swims, and sunset gatherings right at the water’s edge.

This exceptional waterfront estate offers unmatched panoramic views from house and guest house with extraordinary privacy on a nearly two acre setting rarely found in this coveted Oak Bluffs location. Commanding sweeping vistas of Lagoon Pond, Vineyard Haven, Hines Point, the iconic drawbridge, Vineyard Sound, and even distant views of Cape Cod. The property includes a renovated three-bedroom main residence and a two-bedroom guest house, each thoughtfully oriented to capture the ever changing light over the water. The main home offers a spacious open layout with generous living, dining, and sitting areas, ideally suited for entertaining and family gatherings and all with stunning views of the water. A large, bright kitchen serves as the heart of the home, while the living room, dining room, primary bedroom and two elevated decks provide front row seats to boating activity, wildlife, and some of the most spectacular sunsets on the island. The primary bedroom is a serene sanctuary with floor to ceiling water views that feel truly immersive. A second main level bedroom also has water views and its own full bath. On the lower level, a bedroom suite includes a comfortable sitting area with a TV, and spacious full bath. The guest house is a retreat unto itself, offering equally stunning water views from kitchen, living room and private porch. Its large primary bedroom features ample space, while the additional bedroom is a cozy, private nook. Outdoors, the estate’s expansive grounds offer a rare combination of beauty, privacy, and direct waterfront access. Private steps lead to the property’s own sandy beach and mooring, where guests can enjoy swimming, boating, kayaking, paddle boarding, fishing, or simply savor the extraordinary natural beauty. An amazing variety of birds, including osprey complete the scene out on the water. The property also borders 14 acres of conservation land with scenic walking trails, enhancing the sense of seclusion, privacy and connection to nature. This is a truly remarkable island estate that has had only 3 owners in the past 65 years. This is a generational opportunity to enjoy and improve this family compound with unforgettable views, refined living spaces and unparalleled waterfront setting.

Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane presents a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views of the 7th fairway and 8th tee box, across to Sengekontacket Pond, offering a serene backdrop of lush greens and distant water. The historic five-bedroom main residence, along with a separate one-bedroom carriage house, are rich in character and await a thoughtful renovation or reimagining. This is a unique chance to create a bespoke Vineyard estate tailored to modern living while honoring the property’s heritage. Ideally located within close proximity to the clubhouse, restaurant, pro shop, and tennis courts, the home offers seamless access to the best of the Farm Neck lifestyle. While offering a tranquil and private setting, the property is just minutes from boutique shopping, fine dining, the harbor, and ferry terminal—providing both seclusion and convenience. This is an extraordinary chance to secure a property within the esteemed Farm Neck Golf Club community. Included with the offering is a highly sought-after Farm Neck Club Stockholder Membership, enhancing both its prestige and value.

The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an expansive deck, a pergola with a fireplace, and an elevated gazebo overlooking meticulously manicured grounds. Versatility is at the heart of this unique compound. With three kitchens, the home easily accommodates use as a spacious single-family residence or as three separate living quarters—ideal for multi-generational living, hosting extended guests, or generating rental income. Additional highlights include a 10-bedroom septic system in place - allowing for future expansion, an oversized three car garage, and solar. Come experience the very best of Island living.

Location, Location, Location! A once-in-a-lifetime legacy investment opportunity in one of the most desirable and high-visibility locations on Martha’s Vineyard. Priced to sell and positioned for success, 3 Oak Bluffs Ave is prominently situated at the corner of Seaview Ave and Oak Bluffs Ave—you know the spot. This exceptional property places your business directly in the center of it all, with unmatched exposure to both pedestrian and vehicular traffic. Located directly across from Inkwell Beach, Ocean Park, The Steamship Authority and SeaStreak ferry terminals, and Circuit Ave, and just around the corner from Oak Bluffs Harbor, this is a location that simply speaks for itself. And there’s more: the entire on-site parking lot belongs to this property, providing plenty of dedicated parking, with additional parking options available throughout the surrounding area. In a location where parking can be at a premium, this is a significant advantage. Whether you’re looking to relocate an existing business, expand your footprint, or launch your next venture, it’s hard to imagine a better location to bring your vision to life. Put your business at the gateway to Martha’s Vineyard, take advantage of extraordinary visibility and traffic, and position yourself for long-term success. B1 Zoning allows for a variety of commercial uses, offering flexibility for a range of business opportunities. Opportunities of this caliber—and in a location this prominent—rarely come along. This one won’t last. Secure this incredible property and invest in a location that could become the foundation of your next great success.

A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive access to the association’s private dock on Sengekontacket Pond, ideal for kayaking, paddleboarding, and more. This offering also includes a highly coveted stockholder membership to Farm Neck Golf Club, making it a truly unique and valuable investment.

With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the rear of the property, a private guest house—affectionately known as The Nest—has undergone a similar transformation and offers a private escape. Adjacent to the main home, the charming bunk house completes the ensemble, perfectly complementing this unique and inviting expansive compound. Though the wraparound porch invites you to linger with its endless ocean views, the nearby beaches, boutique shops, acclaimed restaurants, and the contagious energy of Circuit Avenue and the Harbor are all steps away, offering something for everyone to enjoy. For those seeking flexibility, the home’s established rental history further highlights the desirability of both the property and its coveted location. An exciting opportunity to own in one of Oak Bluff's iconic settings!

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard.

This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the street, and the Tabernacle, behind the property, host major Island events. Every aspect of the property reflects an outstanding level of craftsmanship and attention to detail. The street level features an expansive commercial space with considerable flexibility for restaurant-bar and/or retail use (for a restauranteur, the kitchen and bar infrastructure are intact and virtually turnkey). The commercial floor includes three handicap-accessible half baths and a convenient and thoughtfully designed rear exterior loading area. The very large newly excavated basement is dry and temperate year-round, providing valuable, clean, safe storage and operational space, an uncommon amenity for downtown Island properties. The second floor includes two beautifully appointed residential apartments, totaling 6 bedrooms and 3 full bathrooms, ideal for creating additional income potential and operational flexibility. The property has a distinctive commercial history, having served in the 1930's as an A&P grocery store (The Great Atlantic & Pacific Tea Company) and, in recent decades, 99-occupancy restaurants and an upscale retail store. Combining outstanding craftsmanship, state-of-the-art building systems, and a highly desirable high-traffic in-town location, this is a premier mixed-use investment offering with broad appeal to investors, business owners, and developers alike.

This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the street, and the Tabernacle, behind the property, host major Island events. Every aspect of the property reflects an outstanding level of craftsmanship and attention to detail. The street level features an expansive commercial space with considerable flexibility for restaurant-bar and/or retail use (for a restauranteur, the kitchen and bar infrastructure are intact and virtually turnkey). The commercial floor includes three handicap-accessible half baths and a convenient and thoughtfully designed rear exterior loading area. The very large newly excavated basement is dry and temperate year-round, providing valuable, clean, safe storage and operational space, an uncommon amenity for downtown Island properties. The second floor includes two beautifully appointed residential apartments, totaling 6 bedrooms and 3 full bathrooms, ideal for creating additional income potential and operational flexibility. The property has a distinctive commercial history, having served in the 1930's as an A&P grocery store (The Great Atlantic & Pacific Tea Company) and, in recent decades, 99-occupancy restaurants and an upscale retail store. Combining outstanding craftsmanship, state-of-the-art building systems, and a highly desirable high-traffic in-town location, this is a premier mixed-use investment offering with broad appeal to investors, business owners, and developers alike.

Perched high above the East Chop bluffs beside the historic lighthouse, this exceptional waterfront estate offers timeless character, breathtaking views, and an unmatched coastal setting. The main residence has beautifully preserved much of its original charm and features a gracious living room with a fireplace, a sun-filled sunroom, and a wraparound covered porch designed to take in the spectacular surroundings. The main house offers five bedrooms and three-and-a-half baths, while a detached two-car garage includes a private one-bedroom apartment above, ideal for guests or extended family. Nearly every room captures sweeping views of Vineyard Sound, where passing boats, ever-changing seascapes, and unforgettable sunsets create a remarkable backdrop. The beautifully landscaped grounds feature expansive lawns stretching to the edge of the bluffs, providing both privacy and dramatic scenery. Completing this rare offering are private steps to the shoreline, a deep-water pier, and a private mooring, an extraordinary opportunity to enjoy one of Martha’s Vineyard’s most coveted waterfront locations.