Great opportunity to build in a quiet, well-established Vineyard Haven neighborhood. This level parcel offers excellent potential with flexible zoning that allows for as many bedrooms as can be accommodated within the allowable footprint, defined by 20-foot front and rear setbacks and 10-foot side setbacks. The property is located outside the Major Tisbury Watershed boundaries, meaning an enhanced septic system is not required, helping reduce costs and simplify the construction process. A versatile site well suited for a year-round residence or seasonal use in a highly desirable location.

MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island. At the bottom of the hill you will find a recreation area with basketball hoops, volleyball net and swings! Could this be the opportunity that you have been waiting for to be a homeowner on the Island? Year-round living or investment home with a solid rental history. Additional financial information provided upon request.

One of Vineyard Haven’s most popular and accessible locations in The Tisbury Marketplace. Water views of Lagoon Pond and Vineyard Haven Harbor. Unit C- 9 at 79 Beach Road offers highly visible exposure in a high-demand area in the Vineyard Haven business district—a few minutes from downtown and the ferry. This 1st-floor unit - features 602 square feet of space, flexible layout adaptable to multiple business types (wide range of uses including retail, professional services, office, or health services) 1/2 bath that is shared with adjoining unit. Open floor plan with big open front room, 3 changing rooms, a back office area and another small room, with backdoor access. With excellent with steady vehicle and foot traffic and prominent road frontage , and ample on-site parking; well-maintained complex with professional management; and easy access to ferry, shops, and restaurants.

This home has been patiently awaiting its next chapter in Vineyard living. Built in 1983, it offers a functional center-entrance layout with efficient use of space and modern systems already in place. The generously sized lot, both wide and deep, presents an excellent opportunity to expand the home's footprint and tailor it to your vision. Located in the Spring Hill neighborhood of single-family homes, just one mile from the heart of Vineyard Haven and moments from Lake Tashmoo. This property provides easy access to downtown amenities while remaining close to peaceful water views and natural surroundings for which Martha's Vineyard is known. Please note, this property is being sold in "as-is" condition, and a new septic system is needed at the buyer's expense. Possibility of a 5-bedroom septic allowed. Ring cameras on the property. Please Do Not Walk The Property without an Agent.

A rare opportunity to own a historic Martha’s Vineyard home just moments from town. Originally built in 1900, this charming 3-bedroom, 1.5 bath home in Vineyard Haven offers 1,395 sq ft of living space on a 0.20-acre lot, blending classic island character with an unbeatable location! Enjoy the ease of walk-to-town living in Vineyard Haven, with nearby access to shops, restaurants, the harbor and ferry. With a little TLC and vision, this property can come back to life! It's been a few years, but the yard and gardens were very beautiful and a large maple in the backyard adds some shade and beauty. A large basement for storage and an old-style root cellar allow for extra storage. There is a parking spot for two off-street, plus on-street parking. Please note, this property is being sold in "As-is" condition and with a new septic needed at buyers expense. Possibility of a 4 bedroom septic allowed. Easy to show, come take a look!

2 bedroom 2 bath cottage with 1 bedroom 1 bath ADU. Large 15,950 square foot lot, short distance to school and town. Second floor bedroom space is large and possibly convertable to 2 bedrooms. New windows and 2 mini split systems, ADU also has a mini split unit. ADU is beleived to have been built in 2017. Property is loacted in Tashmoo watershed district and will require an upgrade to an nitrogen reducing septic system at buyers expence. Being sold in AS IS condition.

In a peaceful Vineyard Haven setting just moments from town, 50 Lantern Lane offers a refined take on classic island living. Privately sited in a quiet enclave yet only one mile from Main Street, Owen Park Beach, and dining and just 1.2 miles from the ferry—this property blends convenience with serenity. The three bedroom, two bath residence spans 1,040 square feet and features a thoughtfully designed layout, including a sought after first floor bedroom. Sun filled living and dining spaces open seamlessly to outdoor decking and a tranquil backyard, creating an effortless indoor-outdoor lifestyle synonymous with Martha’s Vineyard. Modern comforts include an efficient heat pump system with mini-split heating and air conditioning. An unfinished lower level provides storage and laundry, while the outdoor shower and private yard complete the quintessential Vineyard experience. Set on 0.22 acres with town water service, the property presents an exceptional opportunity for a year round residence, refined summer retreat, or investment in one of Vineyard Haven’s most convenient locations. A $25,000 seller credit toward the required septic upgrade further enhances the offering. A rare balance of privacy, proximity, and potential—just minutes from the best of Martha’s Vineyard.

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, including 24 trees added for screening, 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. Several images include virtual staging.

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!

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.

Beautifully renovated and full of charm, this Vineyard Haven home combines stylish design with modern function in one of the island’s most sought-after neighborhoods. Every space has been thoughtfully planned to offer flexibility, comfort, and light, while maintaining the relaxed character that defines Martha’s Vineyard living. The result is a home that feels spacious yet inviting—with elegant details inside and a picture-perfect outdoor setting ideal for entertaining or quiet enjoyment. Current home offers 3 bedrooms; septic system/design is for 4-bedroom capacity. Buyer to verify expansion/use potential with the Town of Tisbury and applicable permitting authorities. AI has been used to enhance the exterior of the home and backyard to add spring color.

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, the site is large enough to support a 5-bedroom septic system; a 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.

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.

Welcome to 20 Union Court, Unit C at the Old Stone Bank Condominiums - a unique community in the heart of downtown Vineyard Haven. This two-level condo offers a truly special Vineyard lifestyle. Enter through the inviting porch into an open floor plan filled with character, thoughtful details, and sun-lit rooms that create a warm and welcoming atmosphere throughout. This home features a well-appointed kitchen, an intimate living area with wood-burning fireplace, a wall of built-in shelves and more. As you move around the space, you will enjoy glimpses of the water. Enjoy your coffee and al fresco dining on the side deck while watching the boats in the Vineyard Haven Harbor. The main level is completed by a sun-drenched bedroom with en suite bath. The second level features a bonus room with en suite bath and a loft area. There are wood floors throughout the first level and carpet on the second. Both bathrooms have tile. High-efficiency heat pumps for heating and cooling. The covered brick patio overlooks the courtyard and is a shared space. There is a shared storage area on the opposite side of the building is perfect for bikes and beach chairs. All this just steps from the ferry and everything the downtown Vineyard Haven has to offer. Association is on the harbor with easy beach and water access. Unit comes with a dedicated parking space.

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.

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.

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.

The Premiere Townhouse at Tashmoo Wood. Elegantly renovated, this sun-filled end unit is fresh and modern with fine finish details. From the moment you step onto the expanded wrap-around deck, you will begin to see the fine craftsmanship of the property. Walk through the front entry and you will gain further appreciation for the meticulous attention to detail. Expansive windows fill the living area with light while providing a view to the side yard and fountain down below. Enjoy evenings on the deck or in front of the wood-burning fireplace. Any chef will be happy in the well-appointed kitchen with Thermador appliances that include a 5-burner cook top and double wall ovens, sizable island with seating, and counters topped with quartz. The kitchen affords views to the dining and living areas as well as out to the deck and yard. There is a first-floor room with an en suite bath. Pocket doors allow for the bath to be a powder room while providing privacy to the flex-room. Ascend the modern staircase to be wowed by the primary suite. The spa-like bath has double sinks and a make-up vanity. There is a glass-enclosed, tiled shower with multiple shower heads. The walk-in closet has been finished with hanging rods, shelves, and drawers. and there is a sliding door that opens to a balcony overlooking the yard. The second en suite bedroom has plantation shutters and a bathroom with a tub. Behind a pocket door, in the hall, you will find a well-organized laundry room with commercial-sized washer and dryer. White oak floors throughout the first and second level with tiled baths. Rinnai on demand water heater. Plantations shutters and custom shades throughout. There is an over-sized garage that is larger than many of the other units. With association amenities that include a pool with pool house, multiple tennis courts, playground, basketball court, private access area to Lake Tashmoo, and a beach on Vineyard Sound. If you are looking for luxury with the convenience of townhouse living, look no further than this truly spectacular unit.

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.

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!

MIXED USE PROPERTY WITH PROFESSIONAL OFFICES AND TWO-BEDROOM APARTMENT – Extensively renovated mixed-use property offering commercial + residential use in a high-visibility location on State Road in Tisbury. This versatile property presents a true live-work opportunity with income-producing potential. The first floor offers four offices including a reception area, 1.5 baths, and a kitchenette, with both front and side entrances, including handicap access. The second floor features a bright and sunny two-bedroom apartment with a full bath, living room, and kitchen—ideal for owner occupancy or rental income. The entire building has been renovated and includes heat and air conditioning throughout, off-street parking for multiple vehicles in the rear, and a yard. Seller financing available, please inquire!

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!

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 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.

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 artist and author of New York Times best-seller "Martha's Vineyard, Isle of Dreams," this quintessential Greek Revival gem with Neoclassical touches enjoys over 3,300 s.f. of living space on more than a half acre in town with wood floors throughout and day long, east to west sunlight. 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, eat-in kitchen with wainscotting, east-facing side porch, laundry/storage room, and a half bath. With a convenient back staircase off the kitchen, the second floor includes additional spacious rooms: A large primary bedroom with fireplace and ensuite bath, sitting room, three additional bedrooms, one with bay window, plus two additional full baths. Wonderful two-story carriage house - barn, expansive lawn and yard, tea-house pergola for afternoon tea, cocktail social, and alfresco dining. Seller has plans 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." *Extensive list of furnishings and household items available for purchase by separate bill of sale. 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.

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 property is truly turn-key and has been meticulously maintained. A true gem!

Rare B2 Commercial Property on State Road in Vineyard Haven. Positioned in a high visibility location this 12,697SF commercial parcel offers two structures and ample on site parking. The main building has been extensively renovated and thoughtfully expanded. Currently configured as an open concept retail showroom, the main level is filled with natural light from numerous windows and enhanced by recessed and spotlight lighting. A significant expansion/renovation including enclosing front and rear porch areas, plus a 19' x 22' addition was professionally engineered by John Lolly, PE adding functionality and value. The second floor offers additional flexibility with an open office area and two private rooms. A second detached structure provides approximately 852SF of additional space ideal for storage, studio use or supplemental business operations. The property is currently serviced by a cesspool system. Buyers may consider upgrading to a nitrogen reducing septic system or potentially pursuing a waiver for connection to municipal wastewater subject to local approvals. Ample parking for customers and staff. This is a standout commercial offering in a limited inventory market ideal for investors or owner-operators seeking a strategic Vineyard Haven location. Existing business is not part of the sale though it may be negotiable.

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.

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.

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.

Welcome to this stunning 4-bedroom, 3-bathroom primary residence along with a 1-bedroom studio apartment over the one-car garage, ideally located in West Chop! Together, they include approximately 3,871 square feet of beautifully renovated living space (an additional 510 sqft of living space on the 3rd floor in the main house is not included on the town assessment). Situated on a .99-acre lot, this spacious home provides the perfect blend of modern upgrades and timeless charm, with plenty of room for both relaxation and entertainment. Completely designed and rebuilt in 1999, the home features an open-concept design with a charming living room complete with a cozy fireplace, an inviting dining room, and a cheerful sunroom, all creating a warm atmosphere for gatherings and entertaining. The spacious kitchen has ample cabinetry and a large counter perfect for casual meals and entertaining. The first-floor primary suite provides a serene retreat with generous space and an en-suite bathroom. Upstairs, you’ll find an expansive second-floor primary en-suite bedroom with a cathedral ceiling and a separate dressing area. There are two additional bedrooms and a full bathroom on the second floor, all thoughtfully designed for comfort and privacy. The third floor adds an exciting bonus space that can be customized as a home office, playroom or workout area. Outside, a large porch, a charming gazebo, and a gracious, fully landscaped yard provide a private oasis for outdoor living – whether you’re hosting a barbecue, gardening or simply enjoying the peaceful surroundings, the space offers endless possibilities. The property includes a one-car garage with a separate studio apartment above, ideal for visitors, as a rental opportunity, or a creative workspace. With its prime location, expansive lot, and thoughtful design, this turn-key home offers an incredible opportunity to own a piece of paradise. Don’t miss your chance to experience the perfect blend of luxury and comfort. *Owner exclusion list available upon request*

West Chop Dream Home in the Making! Experience the charm of this brand-new Shingle Style Colonial, currently under construction. Featuring 4 spacious bedrooms, 4 full and one half bath. This thoughtfully designed home offers generous space. Venture outside into your private oasis, complete with an in-ground pool (36' x18') — perfect for sun-soaked afternoons and evening gatherings. Situated in a prime West Chop location, you're just 2 minutes from Mink Meadows Golf Club and a scenic 7-minute journey to the West Chop Tennis Club. Spend the day at nearby Owen Park Beach or Tisbury Town Beach, both just moments away. Then head 1.5 miles into Vineyard Haven for top-tier shopping, dining, and island charm. This serene property isn’t just a home—it’s a lifestyle. Don’t miss your opportunity to own in the heart of West Chop. Targeted completion June 2026. *Virtual images closely represent the home's intended design and finishes, but some variations may occur in the final product.* **Offered unfurnished; renderings have been staged to provide inspiration** *estimated taxes based on 2024 assessed property not new build.

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 artist and author of New York Times best-seller "Martha's Vineyard, Isle of Dreams," this quintessential Greek Revival gem with Neoclassical touches enjoys over 3,300 s.f. of living space on .92 acre in-town with wood floors throughout and cheerful morning and afternoon sunlight. 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, eat-in kitchen with wainscotting, east-facing side porch, laundry/storage room, and a half bath. With a convenient back staircase off the kitchen, the second floor includes additional spacious rooms: A large primary bedroom with fireplace, double closets and ensuite bath, sitting room, three additional bedrooms, two with double closets, one with bay window, plus two additional full baths. Wonderful two-story carriage house - barn, expansive lawn and yard, tea-house pergola for afternoon tea, cocktail social, and alfresco dining. Seller has plans 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." Extensive list of furnishings and household items available for purchase by separate bill of sale. Property is also available for purchase at $2,300,000 without the approved 12,527 s.f. buildable lot

Built in 2016 by Squash Meadow Builders, this exceptional five-bedroom Colonial is ideally situated just moments from the sandy shores of Tashmoo Beach on Vineyard Sound. Thoughtfully designed across four levels of living, the home seamlessly blends timeless architecture with modern comfort. The main level offers an inviting open floor plan with a spacious living room with gas fireplace anchored by a gourmet kitchen with custom built-ins and charming bench seating. The kitchen blends effortlessly into a light-filled sunroom, creating the perfect setting for relaxed coastal living. A generous first floor primary suite provides privacy and convenience. The second level features bedroom suite with a private bath and three well-appointed guest bedrooms share a full bath with recently updated modern tile and vanity. The finished third level offers an expansive bunk room, ideal for extended family or guests. The finished lower level is designed for entertainment and wellness, featuring a media room, home gym, and ample storage. Indoor and outdoor living connect beautifully where the new sunroom opens to a pergola-covered stone patio overlooking a saltwater pool framed by a classic stone wall. The backyard is a private oasis, complete with an outdoor stone fireplace and lush landscaping accented by blue hydrangeas, perennials, and native sea grass. Additional highlights include a one-car garage and solar panels for energy efficiency. A turnkey Martha’s Vineyard retreat offering comfort, style, and effortless summer living near one of the island’s most beloved beaches.

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.

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.

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.

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.