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Vineyard Haven
Lot 1 Dolan Avenue, Vineyard Haven MA 02568

LINK ID: 44352
Town: Vineyard Haven
Type: Unimproved Land
$525,000.00

Property Details

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.

124 Skiff Avenue # 11, Vineyard Haven MA 02568

LINK ID: 44458
Town: Vineyard Haven
Type: Condominium
$550,000.00

Property Details

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.

124 Skiff Avenue # 12, Vineyard Haven MA 02568

LINK ID: 43844
Town: Vineyard Haven
Type: Condominium
$565,000.00

Property Details

MOVE RIGHT IN! Just in time to ENJOY FOR THE SUMMER! 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 playground! 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.

52 Heath Hen Lane, Vineyard Haven MA 02568

LINK ID: 44535
Town: Vineyard Haven
Type: Unimproved Land
$639,000.00

Property Details

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.

96 Dunham Avenue, Vineyard Haven MA 02568

LINK ID: 44578
Town: Vineyard Haven
Type: Single Family Residence
$949,000.00

Property Details

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.

15 Goah Way, Vineyard Haven MA 02568

LINK ID: 44159
Town: Vineyard Haven
Type: Single Family Residence
$1,100,000.00

Property Details

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.

299 Daggett Avenue Unit A, Vineyard Haven MA 02568

LINK ID: 44426
Town: Vineyard Haven
Type: Single Family Residence
$1,175,000.00

Property Details

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.

61 Wood Chips Circle, Vineyard Haven MA 02575

LINK ID: 44510
Town: Vineyard Haven
Type: Single Family Residence
$1,195,000.00

Property Details

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.

261 Sandpiper Lane # 12, Vineyard Haven MA 02568

LINK ID: 44304
Town: Vineyard Haven
Type: Condominium
$1,250,000.00

Property Details

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.

22 Oklahoma Avenue, Vineyard Haven MA 02568

LINK ID: 44007
Town: Vineyard Haven
Type: Single Family Residence
$1,300,000.00

Property Details

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.

116 Franklin Terrace, Vineyard Haven MA 02568

LINK ID: 44136
Town: Vineyard Haven
Type: Single Family Residence
$1,325,000.00

Property Details

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!

51 Summer Street, Vineyard Haven MA 02568

LINK ID: 44326
Town: Vineyard Haven
Type: Single Family Residence
$1,369,000.00

Property Details

Rare under-$1.4M value story in Vineyard Haven. In a Martha’s Vineyard price range where buyers are often choosing between smaller homes, dated interiors, limited bath count, or properties needing immediate improvements, 51 Summer Street offers a cleaner path. This updated 4-bedroom, 2.5-bath home features 1,783 square feet of well-planned living space in a convenient Vineyard Haven setting near restaurants, shops, harbor activity, and ferry service. The home is designed for practical Island living, with comfortable gathering spaces, an updated kitchen, flexible bedroom layout, and the ease of move-in-ready condition. For buyers who want to enjoy Martha’s Vineyard without beginning their ownership with a renovation list, this property stands out. At $1,395,000, 51 Summer Street is not the lowest-priced home in the under-$1.4M market — it is one of the stronger value stories, offering meaningful square footage, functional bedroom/bath configuration, and updated condition in one of the Island’s most accessible year-round locations.

4 Lagoon Pond Road, Vineyard Haven MA 02568

LINK ID: 42148
Town: Vineyard Haven
Type: Single Family Residence
$1,395,000.00

Property Details

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.

39 Ferro Way, Vineyard Haven MA 02568

LINK ID: 44398
Town: Vineyard Haven
Type: Single Family Residence
$1,488,000.00

Property Details

Tucked away on a quiet cul-de-sac, this beautifully maintained single-family home offers the perfect blend of privacy and convenience. Built in 2020, the property features 5 spacious bedrooms and 4 full bathrooms across 2,884 square feet of thoughtfully designed living space.Set on a generous 15,593 sq ft lot, the home provides ample outdoor space with exciting potential for a guest house, garage, or future expansion. A six-bedroom septic system is already in place, offering added flexibility for growth. Ideally located just a short distance from downtown, Lake Tashmoo boat landing, and town tennis courts, this property combines peaceful neighborhood living with easy access to local amenities and recreation. Note: property is located in the Tashmoo Watershed District, but has a NitROE system.

33 Alyssa Lane, Vineyard Haven MA 02568

LINK ID: 43928
Town: Vineyard Haven
Type: Single Family Residence
$1,495,000.00

Property Details

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.

455 State Road # 8, Vineyard Haven MA 02568

LINK ID: 43832
Town: Vineyard Haven
Type: Commercial
$1,500,000.00

Property Details

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.

110 Clover Hill Drive, Vineyard Haven MA 02568

LINK ID: 44254
Town: Vineyard Haven
Type: Single Family Residence
$1,575,000.00

Property Details

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.

22 Old Lighthouse Road, Vineyard Haven MA 02568

LINK ID: 43800
Town: Vineyard Haven
Type: Single Family Residence
$1,595,000.00

Property Details

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.

150 Cove Road # 10, Vineyard Haven MA 02568

LINK ID: 43136
Town: Vineyard Haven
Type: Condominium
$1,600,000.00

Property Details

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.

26 Union Court # 7, Vineyard Haven MA 02568

LINK ID: 43064
Town: Vineyard Haven
Type: Condominium
$1,625,000.00

Property Details

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.

26 Union Court # 7, Vineyard Haven MA 02568

LINK ID: 44294
Town: Vineyard Haven
Type: Single Family Residence
$1,625,000.00

Property Details

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.

37 Old Hedge Row, Vineyard Haven MA 02568

LINK ID: 44612
Town: Vineyard Haven
Type: Single Family Residence
$1,770,000.00

Property Details

Move in ready and easy to show! Just atop a modest knoll sits this well cared for, light filled, privately sited, four bedroom custom home. A six bedroom septic offers further spatial enhancement, or ADU potential with proper Town permitting. Convenient to downtown, public library, shopping, eateries, and ferries, the youthful home has an open floor plan, thoughtful built-ins and attractive appointments throughout that promote comfortable living indoors, with a screened porch and ample sized deck to equally enjoy outdoor living. Mature landscaping and natural canopies along the perimeter of the lot provide texture, privacy and shade. A wonderful family home to consider!

41 & 0 Cook Road, Vineyard Haven MA 02568

LINK ID: 44557
Town: Vineyard Haven
Type: Single Family Residence
$1,790,000.00

Property Details

Experience the perfect blend of character, modern comfort, and future potential with this beautifully maintained Vineyard Haven property, offered together with an adjacent 16,000 square foot buildable lot. Encompassing approximately .69 acres in total, this unique offering provides immediate enjoyment along with the flexibility to create a family compound, construct a second home, or potentially sell the additional lot in the future. Situated just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, the property enjoys a convenient location while maintaining a peaceful residential setting. The main residence spans 1,924 square feet and features three bedrooms and 2.5 bathrooms, complemented by wood flooring throughout and central air conditioning. The main living spaces are warm, inviting, and designed for everyday living and entertaining. An updated kitchen with walk-in pantry opens to the dining area, while a spacious living room addition creates a comfortable gathering space filled with natural light. A powder room with laundry adds convenience to the first floor. A substantial addition completed in 2010 also introduced a generously sized second-floor primary suite. Two additional bedrooms and a full bath provide ample accommodations for family and guests. Outdoor living is equally appealing, with a large deck overlooking beautifully landscaped grounds accented by native plantings, stonework, a charming fire pit gathering area, and a detached studio ideal for creative pursuits, hobbies, or additional workspace. A full walk-out basement offers abundant storage and additional possibilities. Whether you're seeking a year-round residence, a vacation retreat with room to expand, or an investment opportunity with future development potential, this rare Vineyard Haven offering combines comfortable living, a highly desirable location, and the added value of a separate buildable lot.

79 Beach Road # B14, Vineyard Haven MA 02568

LINK ID: 44193
Town: Vineyard Haven
Type: Commercial
$1,799,000.00

Property Details

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!

378 State Road, Vineyard Haven MA 02568

LINK ID: 44091
Town: Vineyard Haven
Type: Commercial
$1,950,000.00

Property Details

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!

33 Lagoon Pond Road, Vineyard Haven MA 02568

LINK ID: 43812
Town: Vineyard Haven
Type: Single Family Residence
$1,975,000.00

Property Details

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!

81 Leland Avenue, Vineyard Haven MA 02568

LINK ID: 44184
Town: Vineyard Haven
Type: Single Family Residence
$1,975,000.00

Property Details

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.

0 State Road, Vineyard Haven MA 02568

LINK ID: 44340
Town: Vineyard Haven
Type: Unimproved Land
$2,000,000.00

Property Details

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.

398 Main Street, Vineyard Haven MA 02568

LINK ID: 44460
Town: Vineyard Haven
Type: Single Family Residence
$2,000,000.00

Property Details

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.

237 Lagoon Pond Road, Vineyard Haven MA 02568

LINK ID: 44301
Town: Vineyard Haven
Type: Single Family Residence
$2,150,000.00

Property Details

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.

21 Woodlawn Avenue, Vineyard Haven MA 02568

LINK ID: 43234
Town: Vineyard Haven
Type: Single Family Residence
$2,200,000.00

Property Details

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.

268 Tashmoo Avenue, Vineyard Haven MA 02568

LINK ID: 43633
Town: Vineyard Haven
Type: Single Family Residence
$2,290,000.00

Property Details

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!

70 Spring Street, Vineyard Haven MA 02568

LINK ID: 42020
Town: Vineyard Haven
Type: Single Family Residence
$2,300,000.00

Property Details

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.

159 Lake Street, Vineyard Haven MA 02568

LINK ID: 44396
Town: Vineyard Haven
Type: Single Family Residence
$2,400,000.00

Property Details

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.

54 Amelias Crossing, Vineyard Haven MA 02568

LINK ID: 44464
Town: Vineyard Haven
Type: Single Family Residence
$2,595,000.00

Property Details

COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living spaces, creating an effortless connection between indoors and out. A wraparound porch, bluestone patio, patio areas, and firepit create multiple spaces for al fresco dining, entertaining, and gathering after a day at the beach or on the harbor. There is also possible pool potential, adding another layer of future enjoyment. Inside, the home features a cook’s kitchen with granite countertops and stainless steel appliances, beautiful hardwood floors throughout, and four bedrooms, each with its own en suite bathroom. Offered furnished, the property is ready for immediate enjoyment and has an established rental history of approximately $70,000 per year. A full unfinished basement provides valuable expansion potential for additional living, recreation, or storage space. With its classic coastal style, strong rental history, and sought-after Vineyard Haven location close to Main Street, the harbor, and ferry, this property is an exceptional opportunity for year-round living, a seasonal retreat, or investment use.

187 Lagoon Pond Road, Vineyard Haven MA 02568

LINK ID: 43834
Town: Vineyard Haven
Type: Single Family Residence
$2,695,000.00

Property Details

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.

322 State Road, Vineyard Haven MA 02568

LINK ID: 44344
Town: Vineyard Haven
Type: Commercial
$2,700,000.00

Property Details

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.

21 Davis Street, Vineyard Haven MA 02568

LINK ID: 44187
Town: Vineyard Haven
Type: Single Family Residence
$2,825,000.00

Property Details

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.

27 Spring Street, Vineyard Haven MA 02568

LINK ID: 44279
Town: Vineyard Haven
Type: Single Family Residence
$2,895,000.00

Property Details

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.

21 Davis Street, Vineyard Haven MA 02568

LINK ID: 44210
Town: Vineyard Haven
Type: Single Family Residence
$2,925,000.00

Property Details

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.

9 Hagerty Drive, Vineyard Haven MA 02568

LINK ID: 42846
Town: Vineyard Haven
Type: Single Family Residence
$2,995,000.00

Property Details

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.

70 Spring Street and William St. Lot, Vineyard Haven MA 02568

LINK ID: 42618
Town: Vineyard Haven
Type: Single Family Residence
$3,200,000.00

Property Details

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

139 Main Street, Vineyard Haven MA 02568

LINK ID: 44486
Town: Vineyard Haven
Type: Single Family Residence
$3,750,000.00

Property Details

Nestled just two blocks from Vineyard Haven’s working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses—now gracefully combined into a single half-acre parcel—this home offers rare space, privacy, and timeless character in one of the island’s most approachable villages. From the moment you step through the welcoming vestibule, it’s clear this is a home with stories to tell. Wood plank floors, rich woodwork, and generously proportioned rooms speak to its heritage, while thoughtful updates have introduced an easy, understated luxury throughout. The kitchen has been beautifully remodeled with custom cabinetry and stone countertops. Light pours through oversized windows into gracious living and dining spaces, with a fireplace adding warmth and character to the living room. Upstairs, the primary suite offers garden views and a peaceful retreat, while guest bedrooms retain period charm with airy, sunlit appeal. Outside, the grounds feel secluded and mature—a private world behind an original wrought iron gate. Paths wind through perennial gardens and wide lawns, while a porch and flagstone patio invite lingering afternoons in the dappled shade. A charming one-bedroom guest cottage sits tucked away from the main house, offering flexibility for guests, work-from-home, or rental income. This home has long been cherished by artists, collectors, and careful stewards—each adding their layer to the property’s quiet patina. Just a short stroll to the ferry, shops, restaurants, library, and beach, 139 Main Street is a rare find: a truly in-town retreat that feels a world apart. This expansive main house offers flexible living with six rooms currently used as bedrooms, including a separate guest suite. The property has a 5-bedroom septic system per Title 5.

94 Weaver Lane, Vineyard Haven MA 02568

LINK ID: 44191
Town: Vineyard Haven
Type: Single Family Residence
$3,999,999.00

Property Details

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.

95 Hines Point Road, Vineyard Haven MA 02568

LINK ID: 44144
Town: Vineyard Haven
Type: Single Family Residence
$4,300,000.00

Property Details

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.

16 Frog Hollow, Vineyard Haven MA 02568

LINK ID: 43954
Town: Vineyard Haven
Type: Single Family Residence
$4,695,000.00

Property Details

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.

30 Water Gate Road, Vineyard Haven MA 02568

LINK ID: 44248
Town: Vineyard Haven
Type: Single Family Residence
$4,695,000.00

Property Details

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.

31 Lamberts Cove Road  & 0 Plum Cove Road, Vineyard Haven MA 02568

LINK ID: 43366
Town: Vineyard Haven
Type: Single Family Residence
$5,800,000.00

Property Details

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.

41 Hagerty Drive, Vineyard Haven MA 02568

LINK ID: 44567
Town: Vineyard Haven
Type: Single Family Residence
$5,950,000.00

Property Details

Welcome to your Vineyard dream home in the highly sought-after West Chop neighborhood. This exceptional brand-new construction offers 6 bedrooms, 6 full baths, and 1 half bath, thoughtfully designed with timeless coastal elegance and modern luxury. Filled with natural light, the home’s bright and airy interior showcases impeccable craftsmanship, spacious living areas, and a gourmet chef’s kitchen featuring premium high-end appliances, custom cabinetry, and an oversized island perfect for entertaining. An inviting home office provides a quiet space to work remotely, while the expansive bonus room with a wet bar offers the ideal setting for gatherings, game nights, or relaxing with family and friends. Designed for seamless indoor-outdoor living, a sun deck overlooks the stunning pool and beautifully landscaped grounds, creating a private retreat for summer enjoyment. The property is set on just under an acre and framed by mature trees, offering both privacy and tranquility. From select vantage points, enjoy distant views of Vineyard Sound and watch the ferry make its way across the water. Ideally located near West Chop’s beautiful beaches, prestigious clubs, and renowned restaurants, this extraordinary residence combines luxury, comfort, and convenience in one of Martha’s Vineyard’s most desirable locations. Whether as a year-round residence or seasonal escape, this is coastal living at its finest.

395 State Road, Vineyard Haven MA 02568

LINK ID: 43655
Town: Vineyard Haven
Type: Commercial
$6,000,000.00

Property Details

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.

33 Goethals Way, Vineyard Haven MA 02568

LINK ID: 43413
Town: Vineyard Haven
Type: Single Family Residence
$9,250,000.00

Property Details

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.

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