Welcome to Unit B-12 at the Causeway Condominiums, a turnkey studio offering comfortable, low-maintenance island living just a short walk to the charming village of Vineyard Haven. Thoughtfully designed to maximize space and functionality, this inviting residence features warm bamboo flooring throughout, a custom Murphy bed, and a beautifully crafted custom mahogany closet and storage system, providing exceptional organization while making the most of every square foot. The bright, open layout is filled with natural light and offers an ideal blend of comfort, style, and efficiency. Residents enjoy a beautifully maintained in-ground swimming pool with an expansive sun deck and lounge seating the perfect place to relax after a day at the beach or exploring Martha’s Vineyard. The affordable monthly HOA fee of just $221 includes water, on-site dumpster service, grounds maintenance, snow removal, pool maintenance, and master insurance, providing exceptional value and worry-free ownership. Ideally located within walking distance of the Steamship Authority ferry, Vineyard Haven Harbor, Main Street’s shops and restaurants, beaches, and the bike path, this move-in-ready studio offers an exceptional opportunity as a year-round residence, island getaway, or investment property. Enjoy all the convenience and charm of Vineyard Haven with easy access to everything that makes Martha’s Vineyard such a special place to call home. With onsite parking available immediately and strong rental income potential, this property presents a compelling opportunity for investors seeking both lifestyle and return An affordable gem in a highly desirable location.. Call for an appointment.. All offers should include pre approval and or proof of funds.

A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of accessibility and island living. The parcel is not within the Nitrogen Management District, meaning no enhanced septic system is required. A great opportunity to build to suit your needs.

JUST COMPLETED ~ fully renovated exterior including a new roof, siding, shutters, trim, all new windows, doors, stairways, and decks. Outstanding move-in-ready, year-round two-bedroom ground-level condo with dedicated parking in an ideal Vineyard Haven location close to the ferry, Main Street shops, and restaurants. The beautifully maintained common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. Inside, the unit has been tastefully renovated with new hardwood floors, an updated bathroom, updated kitchen appliances, and a freshly painted interior. Being sold furnished, this true gem is ready for immediate occupancy.

GOOD TO GO! This sunny 13,000-square-foot lot is ready for your Vineyard home. The property comes with a complete six-bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process. Conveniently located just off West Spring Street, Heath Hen Lane is a quiet, established dead end neighborhood offering both privacy and accessibility. Enjoy a peaceful residential setting while remaining within an short walk to the Tisbury School or a twenty-minute walk to downtown Vineyard Haven, where you'll find shops, restaurants, galleries, and the ferry terminal. Whether you're planning a year-round residence, vacation retreat, this ready-to-build parcel offers an ideal combination of a location and convenience.

NESTLED ON AN OVERSIZED LOT in a highly convenient Vineyard Haven location, this classic 1972 center-entrance Colonial offers timeless charm and exceptional potential. Inside, an inviting open-concept living space is anchored by a wood-burning fireplace, while soaring vaulted ceilings over the dining area and kitchen create an airy, light-filled atmosphere ideal for gathering with family and friends. The thoughtfully designed floor plan features a desirable first-floor primary suite complete with an en suite bath and a private screened sitting porch—the perfect retreat for morning coffee or quiet summer evenings. Upstairs, two additional bedrooms share a full bath and are connected by an open balcony overlooking the main living area below, adding architectural interest and a sense of openness throughout the home. Outdoor living is equally inviting, with a spacious deck leading to the backyard and providing ample room for entertaining, dining al fresco, or simply enjoying the island breeze. Ideally situated with easy access to the Lagoon, downtown Vineyard Haven, beaches, shops, restaurants, and the Steamship Authority, this property presents an outstanding opportunity to create your own Martha’s Vineyard getaway or year-round residence. Offered as is, this home is ready for its next chapter and the vision of its new owner. Note: Septic will need to be brought into compliance with current regulations.

This cared for contemporary is located in a mature neighborhood abutting Sheriff's Meadow. It has a three bedroom, one bath reverse floor-plan design that captures ample natural light from a serene park-like setting. Hardwoods and ceramic tile flooring, A/C mini-split heat-pumps, a rear balcony deck, outdoor shower, and a delightful terraced patio compliment this new opportunity. *Seller is offering a closing credit of up to $50,000.00 toward the required nitrogen septic system upgrade.

Nestled in a quiet neighborhood just a short stroll from Lake Tashmoo and less than a mile from Main Street, Owen Park Beach, and the Steamship Authority, this lovingly maintained Colonial Saltbox offers the perfect blend of comfort, convenience, and island charm. With a strong rental history, the home is ideally suited as a vacation getaway, year-round residence, or investment property. The first floor features an open-concept living, dining, and kitchen area, along with a bedroom and a full bathroom, providing flexible living options. Upstairs, you'll find two additional bedrooms and a second full bath. The property is located within the Tashmoo Watershed District. To comply with current denitrification requirements, the septic system will require an upgrade.

Some properties you visit, and some properties you experience. Tucked behind mature gardens and a lush natural landscape, 41 Renear Street is a hidden Vineyard treasure — a classic 1927 cottage where timeless character, village convenience, and the beauty of the outdoors come together. Set on a generous .26-acre R10 parcel, this three-bedroom home offers the warmth and craftsmanship of an earlier era, with original architectural details, beautiful wood floors, classic moldings, built-ins, a fireplace, and sun-filled rooms framed by garden views. Thoughtfully cared for over the years, the home retains the authentic charm and easy elegance that make historic Vineyard cottages so beloved. The heart of the home is its connection to nature. Oversized windows invite the gardens inside, filling the living spaces with natural light and views of established plantings, stone pathways, and quiet outdoor sitting areas. Whether enjoying morning coffee overlooking the gardens, gathering by the fireplace, or relaxing among the private outdoor spaces, the property offers a sense of peace rarely found so close to town. With approximately 1,284 square feet of living space, three bedrooms, one and a half baths, an unfinished basement, and outdoor garden shed, the property provides comfortable year-round living today with opportunities to thoughtfully enhance or expand in the future. Just moments from Main Street, Vineyard Haven Harbor, restaurants, shops, beaches, and ferry access, 41 Renear Street offers the best of village living — a private garden sanctuary with the soul of old Martha’s Vineyard. NOTE: An enhanced Title V system will be required wihtin 6 months of purchase.

This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other. Many attractive features include hardwood floors and Indian tile throughout, a large inviting mahogany deck off the front of the house overlooking a koi pond, fully owned solar panels that have covered the electrical costs for the past five years, a nitrogen reducing septic system, a full unfinished walkout basement and a large detached shed. This property is deed restricted to year-round housing and is part of the Daggett Ave. Homeowner’s Association which has a ninety-nine-year ground lease agreement.

Set on a private, wooded lot in Vineyard Haven, this recently built home offers a rare combination of immediate enjoyment and exceptional future potential. Built in 2021, the thoughtfully designed 1-bedroom residence features a bright, modern interior, energy-efficient solar panels, and a peaceful setting surrounded by nature. The true value lies in the property’s remarkable expansion possibilities. A 6-bedroom septic system is already installed, allowing for the future construction of a substantial 5-bedroom main house while retaining the existing home as a guest house, rental property, or secondary dwelling. The lot also has ample room for a pool and outdoor entertaining spaces, creating an ideal Vineyard compound opportunity. Ideally located just over a mile from both the West Chop Club and Mink Meadows Golf Club, as well as downtown Vineyard Haven, the property offers convenient access to golf, boating, dining, shops, and ferry service while still maintaining a quiet, tucked-away feel. Nearby walking trails and conservation land further enhance the property’s unique sense of privacy and connection to the outdoors. Whether you are seeking a turnkey Vineyard retreat, an investment opportunity, or the perfect canvas for a future estate, this offering presents incredible flexibility in one of the island’s most sought-after areas.

END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. This well-maintained 3-bedroom, 3-bath end-unit condo offers a rare combination of privacy, space, and access to one of Vineyard Haven’s most sought-after communities. As an end unit with its own private driveway, this home offers added separation and a more single-family feel—along with a one-car garage and additional storage for bikes and beach gear. Mature plantings enhance the sense of privacy. Inside, the layout is both functional and inviting. The kitchen features granite countertops and high-end appliances and opens seamlessly to the dining area and private deck overlooking peaceful woodlands. The living room, anchored by a wood-burning fireplace, offers a warm and comfortable gathering space, while a first-floor bedroom and full bath provide flexibility for guests or a home office. Upstairs, the primary bedroom includes a private en suite bath with both a soaking tub and separate shower, while the second bedroom is served by a nearby full bath—providing comfortable accommodations with good separation for family and guests. Recent improvements include a new 30-year roof and gutters. Tashmoo Woods is known for its exceptional amenities and ease of ownership, including access to association tennis courts, a heated pool, playground, basketball court, and a private dock on Lake Tashmoo for kayaking and paddle-boarding, along with association beach access on the Vineyard Sound. The community also provides maintenance of roads, building exteriors, landscaping, snow removal, and all shared outdoor spaces and facilities—offering a low-maintenance, turnkey lifestyle ideal for seasonal or year-round living. Mink Meadows Golf Club is just moments away. Seller will offer a credit at closing for septic upgrade. Several images include virtual staging.

3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning solarium or sunroom, a cheerful efficient kitchen, and a sweet living room anchored by a beautiful stone fireplace. The main house has been emptied out and awaits the new owner's touch (please refer to images showing digital staging). Both the main house and the apartment have been freshly painted throughout, radiating a clean and bright atmosphere. Situated on a spacious lot, a 4-bedroom septic design is currently being finalized by Sourati Engineering (buyer to be financially responsible for the upgrade). Other features include oak floors, two decks for outdoor enjoyment, a vintage garden shed, and a full dry basement for additional storage.

Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this beautifully maintained three-bedroom home combines distinctive character with thoughtfully updated spaces, modern comforts, and a peaceful residential setting. The home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An updated custom kitchen by French Accent, with a walk-in pantry, opens to the dining area, while a first-floor powder room with laundry adds everyday convenience. A substantial 2010 addition expanded the home with a spacious, light-filled living room and a generous second-floor primary suite. Two additional bedrooms and a full bath comfortably accommodate family and guests. Outside, a large deck overlooks landscaped grounds with native plantings, stonework, and a fire pit gathering area. A full walk-out basement is perfect for both a work space and storage. Whether you’re searching for a year-round home, vacation retreat, or investment opportunity, this property offers something increasingly rare on Martha’s Vineyard: a home with genuine character, generous living space, and the comforts of modern living.

Nestled on a quiet street just moments from the heart of Vineyard Haven, this well-maintained 4 BR, 3 BA home offers a winning blend of comfort, privacy, and classic island appeal. The sun-filled main level features an open-concept living area flowing seamlessly into a bright, updated kitchen with center island, ideal for everyday living and casual entertaining. Two 1st floor bedrooms and a full bath provide excellent flexibility for guests, home office space, or convenient one-level living, while upstairs offers two spacious en-suite bedrooms designed for privacy and relaxation. Outdoor living shines with a deck overlooking the yard, plus a lower-level bonus with laundry, storage, and workshop potential. Peacefully set yet close to it all, enjoy easy access to public beaches, Tisbury School, and just 0.5 miles to Main Street Vineyard Haven with shops, dining, and ferry access. Perfect as a year-round residence, second home, or investment opportunity—this property checks all the boxes!

Classic Vineyard Charm. Thoughtfully Updated. Move-In Ready. Just moments from Main Street, the harbor, ferry, shops and restaurants, 51 Summer Street offers something increasingly difficult to find—a home that preserves the warmth and character of a classic Vineyard property while providing the comfort and convenience of modern living. Originally built in 1950 and extensively renovated and expanded in 2014, this four-bedroom, two-and-a-half-bath home is ready to enjoy from day one. The welcoming enclosed front porch, with its robin's egg blue beadboard ceiling and walls of windows, sets the tone for the home and creates a favorite gathering place for morning coffee, afternoon reading or evening cocktails. Inside, the open kitchen and living area serve as the heart of the home, complemented by a bright den overlooking the backyard and a flexible first-floor room currently used as an office that is also a legal fourth bedroom. Upstairs, the spacious primary suite offers generous closet space and a beautifully appointed ensuite bath, while two additional bedrooms share an updated full bath. Throughout the home, original five-panel doors, abundant natural light and thoughtful details blend seamlessly with modern updates. Recent improvements include a new roof, new on-demand hot water heater, new washer and dryer, new gas range and new dishwasher, allowing the next owner to simply move in and enjoy Island life. The property has passed Title V inspection, is not located within the watershed district, and the water service line from the street has already been addressed—valuable improvements that provide additional peace of mind. Outside, enjoy a private fenced backyard, mature landscaping, outdoor shower and inviting patio, all just minutes from everything Vineyard Haven has to offer. Whether you're looking for a year-round residence, seasonal getaway or investment opportunity, 51 Summer Street offers timeless Vineyard character with the confidence of significant modern improvements.

Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers require a deed restriction that prevents the property from ever being used as a bike rental shop. Seize this unique chance to establish your business in a highly visible area.

Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs to lower level and garage. 3 Bedrooms 2 full baths on the 2nd floor. Attic. Many windows. High Ceilings. Hardwood Floors throughout. Small front porch to entryway on the first floor level. Lower level above ground office/bedroom with half bath and private entrance from the exterior. Built in Garage and on site parking area. Propane FHW Heat pump A/C. Propane HW Heater. Sited on .23 acres bordered by grassy areas on the side and front of the property. Residential R10 zoning. Small Association. Easy access to Main St, Ferry, Shops, Restaurants, Schools, the Amphitheatre, the Tashmoo Overlook and a direct route to Up Island Towns. Town Water, Title V Four Bedroom Septic System. With the transfer of this property the Septic will need to be upgraded to a Nitrogen reducing Septic system. Owner to provide newly engineered approved septic design when completed.

Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with rental income, investment, employee housing, or multigenerational living. Ready for thoughtful renovation, the property offers an excellent foundation to create long-term value. An attic and basement offer generous storage and space for updated mechanical systems, while an interior staircase provides the opportunity to reconnect the two residences into a single-family home if desired. The seller will provide a $50,000 credit at closing toward the installation of a new septic system.

Discover the opportunity to make this spacious Vineyard Haven home your own, ideally located on the desirable lower end of Lambert's Cove Road. Just across from Pilot Hill Road and approximately one mile from the pristine shores of Lambert's Cove Beach, this well-positioned property offers the perfect blend of convenience, privacy, and potential. Spanning three levels, this five-bedroom, two-and-a-half-bath home offers over 2,000 square feet of living space on a generous 0.26-acre lot, providing an exceptional combination of space, flexibility, and future possibilities. Painted wood floors and inviting living spaces showcase the home's enduring character and timeless appeal. Outside, the property features ample parking, with additional parking and open space both above the home and to the rear of the property, offering endless possibilities for entertaining, recreation, or future enhancements. An approved six-bedroom septic system presents an outstanding opportunity for expansion, allowing the next owner to maximize the property's full potential. Whether you're looking for a year-round residence, a seasonal getaway, or an investment opportunity, this property is ready to be enjoyed today while offering the opportunity to create something truly special for the future.

Charming Property in the Heart of Vineyard Haven. A rare opportunity to own a beautifully maintained main house and guest house nestled on a generous 25,100 square foot lot in Tisbury. This special offering combines charm, privacy and versatility, surrounded by a stunningly landscaped yard. The main house has three full bedrooms and two full bathrooms. The one-bedroom and one-bathroom guest house has a kitchen, loft, private deck, and outside shower. Enjoy easy access to the town's vibrant waterfront, boutique shops, local restaurants, cafés, galleries, and the ferry terminal, making it an ideal location for both year-round living and seasonal escapes. Per the Board of Health, there is no land area restriction; therefore, if a new septic system can be installed without variances, the approved bedroom capacity may be increased. The main house and the guest house both have their own basements with a washer and dryer and plenty of storage.

Tucked away on a quiet cul-de-sac, this beautifully maintained multi-family property offers the perfect blend of privacy, flexibility, and convenience. Built in 2020, the home encompasses 2,884 square feet of thoughtfully designed living space, featuring a total of 5 bedrooms and 4 full bathrooms. The walkout lower level is a fully permitted Accessory Dwelling Unit (ADU), creating an ideal opportunity for multigenerational living, guest accommodations, or rental income while maintaining privacy between living spaces. Situated on a generous 15,593-square-foot lot, the property offers abundant outdoor space with exceptional future potential. A six-bedroom septic system is already in place, providing flexibility for expansion. The home could continue to function as a single-family residence with the addition of a detached guest house/ADU, or it could remain a multi-family property with the potential to add a freestanding ADU, subject to Martha's Vineyard Commission and Zoning Board of Appeals (ZBA) review and approval. Ideally located just a short distance from downtown Vineyard Haven, the Lake Tashmoo boat landing, and town tennis courts, this property combines peaceful cul-de-sac living with convenient access to the island's amenities and recreational opportunities. Note: The property is located within the Tashmoo Watershed District and is equipped with a NitROE wastewater treatment system.Note: property is located in the Tashmoo Watershed District, but has a NitROE system.

Minutes to downtown and the ferry, this updated year-round home checks every box buyers are asking for right now: space, flexibility, and a move-in ready setup in a highly convenient location. 3 bedrooms, 4 bathrooms, and over 3,000 sq ft of living space, including a private lower-level apartment ideal for guests, extended family, or income potential. The main level offers hardwood floors, a renovated kitchen with granite countertops and stainless appliances, and an open living/dining area with fireplace that flows effortlessly for everyday living and entertaining. The primary suite features a private bath and balcony access. The lower level adds a second living/media room, fireplace, laundry, and direct access to the garage. So many upgrades are already done: new roof (2019), 7 mini-splits, updated kitchen and baths, new windows and doors, plus a bright enclosed sunroom. Outside, enjoy a fenced yard, multiple balconies, outdoor shower, firepit, and grilling area, along with a detached garage for boat or vehicle storage. Set on a quiet cul-de-sac with access to 109 acres of trails just beyond your doorstep. Waterloo Biofilter septic system in place (no upgrade required). Title V passed. Water line tested and passed. 4,568 gross sq ft. A rare combination of size, condition, and location this close to town.

Prime commercial opportunity in Vineyard Haven, Martha’s Vineyard’s vibrant year-round community! This 2,614± sq. ft. corner commercial condominium in popular Woodland Center Marketplace —one of the largest in a well-managed association—offers outstanding visibility and versatile space. Currently configured for a tile and flooring business, Unit 8 features a showroom with office area, a workroom/warehouse storage section, kitchenette, and half bath. The flexible layout easily adapts for retail, design, or professional use. With ample parking, professional management, and a high-traffic location, this property is a standout investment. The successful Karpet Kare tile and flooring business is also available separately for those seeking a turnkey operation in a thriving commercial hub.

This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical, evidenced by the well-appointed kitchen which offers direct access to the rear deck for an eat-in or eat-out option. With separate finished living quarters on the garden level, the home easily accommodates guests and multi-generational living. The expansive deck invites morning coffee, summer gatherings, and peaceful evenings surrounded by nature. Mature plantings bloom on stone-scaped retaining walls and evergreen trees provide ultimate privacy. You are just moments from the harbor, shops, and ferry, and yet this property also offers seclusion and privacy - this is a rare combination in this price point.

Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect after a day at the beach. Also on this level is a comfortable guest bedroom with peaks of the harbor, a stylish full tile bath with a glass-enclosed shower, a cozy living area, and washer/dryer for convenience. Upstairs, cathedral ceilings and a gas fireplace create an inviting open-concept living space. The gourmet kitchen is outfitted with sleek Bosch appliances, a large center island ideal for entertaining, and an adjoining dining area. Enjoy panoramic water views of the harbor, passing ferry boats, and Vineyard Sound from the entire second floor, or step out onto your private deck—perfect for alfresco dining or morning coffee. Just steps from your door, a private path leads to the association’s sandy harbor beach, where you can store your kayak or launch your boat. This condo also includes a dedicated parking space and an enclosed storage area under the house ideal for bikes, beach gear, or seasonal items. With easy access to downtown shops, restaurants, ferry terminal, and local beaches, this condo offers the ultimate combination of luxury, convenience, and island charm. A rare opportunity for carefree coastal living on Martha’s Vineyard.

Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect after a day at the beach. Also on this level is a comfortable guest bedroom with peaks of the harbor, a stylish full tile bath with a glass-enclosed shower, a cozy living area, and washer/dryer for convenience. Upstairs, cathedral ceilings and a gas fireplace create an inviting open-concept living space. The gourmet kitchen is outfitted with sleek Bosch appliances, a large center island ideal for entertaining, and an adjoining dining area. Enjoy panoramic water views of the harbor, passing ferry boats, and Vineyard Sound from the entire second floor, or step out onto your private deck, perfect for alfresco dining or morning coffee. Just steps from your door, a private path leads to the association’s sandy harbor beach where you can store your kayak or launch your boat. This condo also includes a dedicated parking space and an enclosed storage area under the house ideal for bikes, beach gear, or seasonal items. With easy access to downtown shops, restaurants, ferry terminal, and local beaches, this condo offers the ultimate combination of luxury, convenience, and island charm. A rare opportunity for carefree coastal living on Martha’s Vineyard.

Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready for your plans or may be sold separately after closing, offering exceptional flexibility for a family compound, second home, or future investment. An easement is being established along the existing driveway to provide access to the residence while allowing the buildable lot to remain an independent parcel. Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this rare offering combines the convenience of in-town living with a peaceful residential setting. The beautifully maintained home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An updated kitchen with walk-in pantry opens to the dining area, while a first-floor powder room with laundry adds convenience. A substantial 2010 addition expanded the home with a spacious, light-filled living room and a generous second-floor primary suite. Two additional bedrooms and a full bath comfortably accommodate family and guests. Outside, a large deck overlooks beautifully landscaped grounds with native plantings, stonework, and a fire pit gathering area. A detached studio provides flexible space for an office, art studio, or hobbies, while the full walk-out basement offers abundant storage. Whether you're searching for a year-round home, vacation retreat, or investment opportunity, this property offers something increasingly rare on Martha's Vineyard: a move-in-ready home paired with a separate buildable lot, all in one purchase.

TISBURY MARKETPLACE offers an active and well-established setting for this beloved eatery. The year 'round destination hub draws proven foot traffic and a healthy commercial environment. Rocco’s Pizzeria anchors the corner of the water view plaza with sustained history and a devoted following. Open throughout every season, the operation inhabits two connecting condo units as well as an additional second floor al fresco dining area. Front facing exterior areas include the raised first level outdoor deck seating as well as a stairway accessing the rooftop dining area with views of Tisbury Harbor and the Lagoon. Rear access provides an easy delivery entrance directly into the kitchen, storage and a rear second staircase up to the outdoor dining area. Permits for seating (81) and beer and wine licenses are transferable with application and approval. Sale package includes commercially appointed kitchen and food prep appliances, fixtures and furnishings. Full inventory and equipment lists available. With 20 years of successful service and consistent offerings no matter the season, it’s easy to envision ownership!

This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and heavily wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water nearby, and an enhanced septic system should allow at least four bedrooms. This quiet, beautiful neighborhood has seen many improvements and new construction in recent years, making it quite desirable. While being a tranquil neighborhood, you are still in close proximity to the shops and restaurants of Main Street, the Steamship Authority, Museum, and the MV Film Center.

Rarely does such a unique, waterfront location become available. With amazing, 180+ degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Wake up to glorious sunrises. Be entertained by a variety of waterfowl throughout the seasons. Have your vessel at the ready right off the shore. The moment you walk onto the property, the tranquil feel and the cooling shade trees will make you forget that you are still so close to town and ferry. The property is hugged by the Lagoon on one side and Vineyard Haven Harbor across the street on the other. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private water access, is a year-round home with breathtaking, expansive views up and across the lagoon. The upper level has a spacious deck overlooking the gardens and sweeping views of the lagoon. The waterside patio has beautiful perennial gardens. A canopy of mature shade trees keeps the property cool. Enjoy meals al fresco in the shade while enjoying the water views. There are many creative details throughout. The sellers have been actively making improvements to increase the commercial usage. Soon the be an art gallery, the commercial building is currently used as an artist’s studio. Built with SIPS construction, this building is energy efficient and wind resistant. Property is connected to the town sewer and town water. Please note: This property is being sold "as is". Buyer is responsible for completing the necessary due diligence with the town and an engineer about this unique property that offers a plethora of opportunities.

Close to town with exceptional indoor / outdoor flow & privacy. Consider this beautifully designed home just minutes from town. The first floor features a bright, open kitchen + dining area flowing into a welcoming living room with a fireplace. From there, step onto a spacious deck—ideal for al fresco dining and lounging—complete with direct access to a hot tub and nearby outdoor shower. The main floor primary suite is a true retreat, with lofty ceilings, a large walk-in closet, and an elegant bathroom with soaking tub. Doors open to a screened porch that feels like a private sitting room—and connects you easily to the outdoor amenities like the hot tub and outdoor shower. Hardwood flooring spans the first floor, with a convenient half bath for guests. Upstairs, find two light-filled bedrooms with generous closets, eave storage, and a full bath, and cozy cork flooring underfoot. The walk out basement is primarily finished into a flexible space with great natural light. This is ideal for a gym, office, or casual living room. There is ample dry storage and potential to use it as a fourth bedroom (septic permitting). Additional Highlights: The level of landscape and hardscape on this property really elevates the setting. The yard is spacious and well-fenced. You can walk past an upper patio area to a private gate where you can jump on trails for a nice walk from your backyard. The sunny front covered porch has ample room for outdoor living and enjoying the south side of the property. The mature plantings really create a feeling of privacy on this serene lot with the Vineyard Haven amenities so close by (restaurants, Mink Meadows conveniently located behind the house, the VH Yacht Club, West Chop Yacht Club, Owen Park, Tashmoo, and the town tennis courts -clay and hard surface). Life is convenient in Tisbury! Don’t miss this opportunity to live where design, comfort, and location converge. An existing five-bedroom septic system allows for easy expansion of an additional lower-level bedroom and bath, as well as an ADU.

Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom tile bathrooms and seamless living both indoors and out. Enjoy water views from the living room, bedrooms and the inviting front porch, perfect for relaxing or entertaining, while the private backyard and spacious back deck provide the privacy many desire. The two-car garage provides a rare in-town convenience, for both parking and storage of your island car and beach gear. The property also boasts impressive rental history, look no further for your next in town purchase - an exceptional, well-rounded offering! Note: This property is also available for purchase with 29 Lagoon Pond Road as a combined offering for $3,295,000.

Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living spaces. At the heart of the home is a chef’s kitchen featuring custom cabinetry, high-end appliances, and stylish finishes—perfect for both everyday living and entertaining. The open-concept living and dining areas flow seamlessly, enhanced by updated systems and central air conditioning for year-round comfort. Upstairs, the primary suite provides a serene escape with a spa-like tile bath and soaking tub. Two additional guest bedrooms share a beautifully appointed full bath that also includes convenient laundry. Unique details like a compass rose stained glass window add a distinctive nautical touch. The finished lower level offers even more living space, including a large bedroom—ideal for guests or extended family. Outdoors, a stunning mahogany deck overlooks the newly landscaped backyard, complete with an outdoor shower and perfect areas for entertaining. With close proximity to downtown Vineyard Haven and the beaches of Vineyard Sound, this exceptional home captures the essence of island living—timeless, refined, and move-in ready.

1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

Ideally situated on Main Street in Vineyard Haven, just moments from the Yacht Club and West Chop, this charming four-bedroom, six-bathroom home offers the perfect blend of convenience, comfort, and Island living. Set on a quarter-acre lot, the property features a private and inviting backyard—ideal for entertaining, gardening, or simply enjoying warm summer evenings. Inside, generous living spaces and a flexible floor plan provide plenty of room for family and guests alike. Enjoy the rare combination of a peaceful residential setting with the convenience of being just a short walk to downtown Vineyard Haven’s shops, restaurants, ferry terminal, and harbor. Whether you’re seeking a year-round residence, seasonal retreat, or investment opportunity, this well-located home captures the best of Martha’s Vineyard living. A wonderful opportunity to own a home in one of Vineyard Haven’s most desirable neighborhoods, where town, beaches, and West Chop are all at your doorstep.

Ideally located at the beginning of Hines Point, this light-filled, well-maintained home offers a central setting with easy access to the Lagoon, the MV Museum, and town. Public water access is just a short walk away, making it easy to enjoy all the benefits of this special area. Set on a gentle rise overlooking the Lagoon, the home is filled with natural light and offers beautiful water views. A bright sitting room welcomes you and flows easily into the kitchen and dining area. The dining room opens to a large deck, perfect for outdoor dining or simply enjoying the view. The cathedral living room is filled with glass and natural light, with a fireplace and sliders to the deck that create an easy indoor outdoor feel. The first floor includes a bedroom with a slider to a private deck and a renovated full bath, ideal for one level living. Upstairs are two comfortable bedrooms connected by a Jack and Jill bath. The grounds are just as inviting, with a park like yard, mature trees, and thoughtful landscaping that provide both beauty and privacy. An irrigation system keeps everything lush, while the pea stone driveway lined with cobblestones adds classic Vineyard charm. The home is equipped with a solar array and heat pumps for efficient, year-round comfort. An easy, comfortable home in a prime location with great light, views, and a setting that feels both private and connected to everything. Seller will provide design, permitting and installation of a 4-bedroom NitROE septic system, as required by the Town of Tisbury.

Thoughtfully designed with custom features throughout, this in-town Vineyard Haven home is the perfect blend of coastal charm and modern sophistication. The 4 bedroom 3 bath property offers a comfortable, easy flowing layout with gleaming hardwood floors and open sun-filled spaces. At the heart of the home is a chef-inspired gourmet kitchen with premium appliances, ample counter space, a generous walk-in pantry and a separate window-lined dining area ideal for both casual or formal dining. Enjoy alfresco dinners on the private deck or unwind on the cozy porch, creating the perfect backdrop for island evenings. Located steps from the ferry, shops, restaurants, and the Vineyard Haven Yacht Club, you’ll have everything at your fingertips while still enjoying a peaceful, private setting. Perfect as a year-round residence or island retreat, this exceptional Vineyard Haven home offers a rare opportunity to enjoy the best of Martha’s Vineyard living.

Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating areas, all overlooking the expansive manicured lawn. On the 1st floor is a full bath and a bedroom that is currently being used as a sewing room. The top floor showcases the expansive primary bedroom en-suite which has a seating area with sliders that lead to a private outdoor balcony. This bedroom offers a large walk in closet and a luxurious bathroom. On the lower level there are two more guest bedrooms, a full bath, a lounge and a home office. This property is complimented by its attached garage and outdoor shower. There is a six bedroom septic system in place.The plot can support a guest house with proper approvals from the HOA and the town. The property is truly turn-key and has been meticulously maintained. A true gem!

Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable lot. For 35 years, home of Susan Branch, the illustrious self-taught illustrator and author of New York Times best-seller "Martha's Vineyard, Isle of Dreams," this quintessential Greek Revival gem with Neoclassical touches enjoys over 3,468 s.f. of indoor space including the summer kitchen (now pantry/laundry) on more than a half acre in town with wood floors throughout and cheerful eastern sunlight mornings and western afternoon sunlight with evening skies. With period paneling, crown molding, and 9' ceilings, the floor plan includes front hall entry with lovely curved staircase, front parlor-studio, formal living room with fireplace and bay window, spacious dining room, second side entrance vestibule used as a dry bar, cozy wood paneled study/tv room ~ "the Snug", eat-in kitchen with wainscotting, east-facing side porch, laundry/pantry/storage room, and a half bath. With a convenient back staircase off the kitchen, the second floor with 8.5" ceilings includes additional spacious rooms: A large primary bedroom with fireplace and ensuite bath, sitting room, linen closet, three additional bedrooms, one with bay window, plus two additional full baths ~ one with claw foot tub. Wonderful two-story carriage house - barn, expansive lawn and yard, tea-house pergola for afternoon tea, cocktail social, and alfresco dining. Seller has drawings for potential renovation of the barn to include a studio apartment - see Documents. Mature plantings including privet, flowering trees and bushes, perennials, historic Linden trees, and herb garden. Six bedroom approved Title 5 septic. A rare opportunity for those who appreciate the history and value of historic homes in a sailing port which as been described as "the sweetest little harbor on the east coast." This property and the owner's abutting Town Approved Building Lot comprised of 12,527 s.f on William Street is available for purchase together for $3,200,000. Some furnishings available for purchase by separate bill of sale.

Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a spacious kitchen with a center island that opens to a dining area. A sunken living room with floor-to-ceiling windows overlooks the surrounding tree canopy, filling the space with natural light. Just off the living room, a large screened porch offers a peaceful setting for relaxing outdoors. Two bedrooms, a full bath, and a laundry room complete this floor. Up the wood staircase, the second level includes a dramatic hallway that overlooks the living area below and leads to a generous primary suite with a spacious bathroom and additional laundry. The third level features a private guest bedroom with its own living area and full bath, ideal for visitors or extended stays. The finished lower level adds even more living space, offering a full bathroom, bedroom windows, and a walkout door to the side yard. A spacious garage provides added convenience and storage. Convenient to the public boat landing on Lake Tashmoo and the Lake Street tennis and pickleball courts, and just a short distance to Downtown, this is the ideal Vineyard Haven location.

Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home encompassing 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect exceptional quality and craftsmanship at every turn. The grounds are equally impressive, featuring beautiful stonework, handcrafted bluestone patios, and professionally landscaped outdoor spaces designed for effortless entertaining. Spend summer evenings by the outdoor fireplace, unwind in the Jacuzzi, or rinse off after the beach in the private outdoor shower, all part of the quintessential Vineyard lifestyle. Lovingly maintained and thoughtfully designed, this home offers an exceptional blend of comfort, style, and convenience just moments from Vineyard Haven Harbor, the ferry, shops, restaurants, and the Island's renowned beaches.

For the very first time, the historic Ben Luce Homestead (circa 1850) is being offered on the open market. This charming farmhouse blends rich Island history with timeless appeal. Once home to Benjamin Norton Luce (1840–1912) — Civil War veteran, blacksmith, and town constable — the property sits on 1.5 acres of pastoral land and offers 5 bedrooms, 2 full baths, solar panels, barn, and a newly updated septic system meeting current standards. Thoughtfully restored for year-round living, the home provides comfort, character, and sustainability. Just minutes from Vineyard Haven’s harbor, shops, and ferry, this rare offering combines privacy with exceptional convenience.Whether enjoyed as-is or further restored as a preservation project, the Ben Luce Homestead is ready for its next chapter — as a year-round residence, summer retreat, or historic Island treasure. The barn offers the perfect foundation for adding an ADU or additional living space, enhancing both functionality and value.

Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five original fireplaces, and 3 zone central heat and AC. Additional conveniences include a mudroom, laundry room and a large screened porch where you’ll find yourself spending more time than anywhere else in the summer time. Two of the five bedrooms are on the first floor, including a private ensuite with a full bath. The home is notable for its unusually large and abundant windows, flooding the south-facing interior with natural light. The winding staircase is a sculptural centerpiece that greets you as you enter through the original front door. Renovations include a new roof over the porch, three modernized bathrooms, and updates throughout the first and second floors, all carefully designed to honor the home’s historic charm. Outside you will find a lawn area and back yard patio that overlook perennial plantings including roses, hydrangeas and dogwood and a white picket fence that creates nice privacy. Plus there is off-street parking for 2 cars. Located just one block from Main Street and two blocks from the Vineyard Haven ferry terminal , this prime location offers easy access to shopping and restaurants and the Tisbury Elementary School. The town tennis courts are just a half-block away, and its a leisurely stroll to the town beach at Owen Park. This is a rare opportunity to own a piece of Vineyard Haven history, where timeless charm meets contemporary comfort.

Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home with 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect the care and craftsmanship the homeowner has poured into every detail. The grounds are equally impressive, featuring beautiful stonework, handcrafted bluestone patios, and professionally landscaped outdoor spaces designed for effortless entertaining. Enjoy summer evenings by the outdoor fireplace, unwind in the Jacuzzi, or rinse off after the beach in the private outdoor shower, all creating a true Vineyard lifestyle experience. Lovingly maintained and thoughtfully designed, this property offers both comfort and refinement just moments from Vineyard Haven Harbor, the ferry, shops, restaurants, and the island’s renowned beaches.

NOW INCLUDING RARE 12,527 S.F. TOWN APPROVED BUILDING LOT ON WILLIAM STREET! Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House*, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District, just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. For 35 years, home of Susan Branch, the illustrious self-taught illustrator and author of New York Times best-seller "Martha's Vineyard, Isle of Dreams," this quintessential Greek Revival gem with Neoclassical touches, enjoys over 3,468 s.f. of indoor space including the summer kitchen, now pantry/laundry room, on .92 acre in-town with wood floors throughout and cheerful eastern sunlight mornings and western afternoon sunlight with evening skies. With period paneling, crown molding, and 9' ceilings, the floor plan includes a welcoming front hall entry with lovely curved staircase, front parlor, formal living room with fireplace and bay window, spacious dining room, second side entrance vestibule used as a dry bar, cozy wood paneled study/tv room~ "the Snug", eat-in kitchen with wainscotting, east-facing side porch, laundry/pantry/storage room, and a half bath. With a convenient back staircase off the kitchen, the second floor includes additional spacious rooms with 8.5' ceilings: A large primary bedroom with fireplace, double closets and ensuite bath, sitting room, linen closet, three additional bedrooms, two with double closets, one with bay window, plus two additional full baths - one with claw foot tub. Wonderful two-story carriage house - barn, expansive lawn and yard, tea-house pergola for afternoon tea, cocktail social, and alfresco dining. Seller has drawings for potential renovation of the barn to include a studio apartment - see Documents. Mature plantings including privet, flowering trees and bushes, perennials, historic Linden trees, and herb garden. Six (6) bedroom approved Title 5 septic. A rare opportunity for those who appreciate the history and value of historic homes in a sailing port which as been described as "the sweetest little harbor on the east coast." Some furnishings available for purchase by separate bill of sale. This property is also available for purchase for $2,300,000 without the approved 12,527 s.f. buildable fronting on William Street.

Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking. 33 Lagoon Pond Road is a newly constructed, thoughtfully designed three bedroom, three bathroom home where luxury meets sophisticated coastal charm. Featuring an open floor plan, a designer kitchen with quartz countertops, custom tile bathrooms, and seamless indoor-outdoor living, the home enjoys water views from the living room, bedrooms, and inviting front porch. A private backyard, spacious rear deck, and attached two car garage provide both privacy and convenience, while the property's impressive rental history adds outstanding investment appeal. Complementing the main residence is 29 Lagoon Pond Road, a beautifully renovated two bedroom, one bath cottage offering its own private retreat with a charming rear patio and outdoor shower. Ideal for extended family, guests, employee housing, or additional rental income, the cottage provides flexibility for a variety of ownership opportunities. A true standout feature of this offering is the oversized rear parking lot at 29 Lagoon Pond Road, accommodating approximately ten vehicles. Parking of this scale is exceptionally rare in downtown Vineyard Haven and significantly enhances the property's versatility. Whether you're seeking a family compound, an income producing investment, or a premier in town property with unmatched flexibility, 29 & 33 Lagoon Pond Road represent a truly one of a kind opportunity in downtown Vineyard Haven.

Set privately in one of Vineyard Haven’s most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and ready access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for both gathering and quiet retreat, with an effortless indoor-outdoor flow that embraces the surrounding landscape. Bedrooms are thoughtfully positioned on opposite wings of the home, with three on one side and two—along with a striking office—on the other. The primary suite is exceptionally private, overlooking neighboring lawns, gardens, and the conservation land. The main living room is warm and inviting, anchored by a massive wood-burning fireplace and complemented by beautiful hardwood floors. A chef’s kitchen connects seamlessly to both indoor and outdoor living areas, ideal for entertaining. An attached two-car garage adds convenience. The grounds feature a wide-open lawn bordered by a classic stone wall, mature plantings, and established garden beds, including a fenced vegetable garden. A post-and-beam barn/boathouse offers flexible space for storage, recreation, or workshop use. Ownership includes access to neighborhood tennis courts and a dock on Lake Tashmoo, making it easy to enjoy morning paddles, sunset swims, and the best of Vineyard coastal living. A property of this scale, setting, and heritage rarely comes to market—an opportunity to carry forward a truly special family estate that combines an "up-island" feel with the convenience of nearby shops and restaurants.

Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its best. Set on 2.25 secluded acres, spectacular panoramic views stretch across the shimmering waters of Lagoon Pond, a private haven for kayaking, sailing, and peaceful exploration. The thoughtfully designed interior features four bedrooms and three full bathrooms, with generous windows framing breathtaking water views from nearly every room. A large family room/library, additional formal living room, and a private guest suite set apart on the far side of the residence offer ample space for homeowners and guests. Outside, the lawn sweeps to the water's edge, where a sandy shoreline invites you to launch a kayak, cast a line, or linger over a sunset picnic. Direct water access puts boating and paddling within easy reach. A detached three-car garage with a finished room above provides generous storage for watercraft, paddleboards, and all the trappings of Island adventure. Just minutes from the shops, restaurants, and harbor are worlds away in feeling, yet close to the best of the Island. Note: Septic Passed Title V inspection, but buyer will need an enhanced de-nitrification septic system Per town of Tisbury regulations. Expansion to six bedrooms possible.

A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the water where you can watch sunrise over the water. A first floor bedroom and bath, expansive living and dining area, and an updated kitchen make up the first floor. There's also an inviting sunroom and large deck perfect for morning coffee or evening cocktails while watching the boats on the Lagoon. The second floor offers a large primary bedroom with en-suite bath and private balcony as well as a second guest bedroom. The bright walk-out finished basement has a family room, full bath, a bonus room, and additional storage space. The property also features a two-car garage and a charming boathouse at the edge of the sloping lawn. The beach is generous and sandy; inviting picnics, swimming, fishing and clamming or you can launch your kayak or paddleboard right from your backyard. The property has a mooring - available to a new owner with proper permitting. The calm Lagoon, which opens to the Vineyard Haven Harbor, is made for boating. The iconic Hines Point neighborhood is a short stroll to Tisbury town center with shops and dining and The Vineyard Haven Yacht Club.

Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage. Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water beyond. The interior feels open, calm, and intentional, with spaces that flow naturally toward the outdoors and keep the focus where it belongs. Outside, the landscape opens gently toward the water. A private beach path sits immediately adjacent to the Vineyard Haven Yacht Club, offering sailing, tennis, dock access, and a café just steps away, an uncommon amenity pairing in such a peaceful, natural setting. Whether enjoyed as a personal escape or leveraged as an income-producing property, the home’s strong rental history reflects its wide appeal. A rare opportunity to own directly on Vineyard Haven Harbor, with a mooring available and the best of Martha’s Vineyard right outside your door.

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and burgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6,000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts. Note: Assessment represents both properties combined.

This well known commercial property, the Pine Village Shops, is being offered to the market for the first time. Currently set up with nine separate rental spaces, all occupied. The location is situated in the center of the State Road commercial district. State Road is heavily trafficked and seen by all when driving by or stopping into to one of the many successful businesses. Additionally a half acre commercial lot next door is also for sale at $2,000,000.

A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. As you enter Vineyard Haven Harbor on the ferry, passing the West Chop Light House, you have the opportunity to own one of the finest estates gracing the harbor front -- so admired by all visitors to the Vineyard. The property is located in the historic Hatch Road neighborhood a short distance to downtown Vineyard Haven and the West Chop Club. From Hatch Road, enter a private way between two stone pillars and experience the bygone era of old Martha’s Vineyard. The home, built in 1900, was the summer residence of Leland and Carol Powers who named their estate “The Mooring.” Leland Powers was a prominent public reader, interpreter of Dickens, once known as the highest paid man in the Lyceum field, and founder of the Leland Powers School of the Spoken Word in Boston. In 1920 the estate was sold to the family of General George Washington Goethals, best known as the Chief Engineer of the Panama Canal. The Goethals family sold to the current owners in 2005 who lovingly restored the elegance of the home over a three-year period. The Goethals family retained the former guesthouse of the estate, with the proviso that the successor owners of the Mooring have a right of first refusal to purchase the guest house property. Enjoy the magnificent views and sounds from the wrap-around porch: spectacular sunrise over East Chop; tell time by the passing ferries; see youngsters learn the art of sailing from the Yacht Club; see the Black Dog tall ships raise their sails in front of you; watch family members and guests enjoy lawn games, and swimming and sunning on the beach; listen to the waves lapping the shore; marvel at the moon light shimmering on the harbor; view firework displays from Oak Bluffs and Edgartown from the comfort of home. Let this home become "The Mooring” for your family.