This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience — just minutes from Lucy Vincent and Squibnocket beaches, and the historic fishing village of Menemsha. Engineering for wells and home sites is complete and utilities are on site. Architectural plans by Morgan Studio for a multi-home compound with a swimming pool and accessory structures are available for review upon request.

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31 Tower Lane and 34 Ebens Lane

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Located in the hot new area of downtown where new construction and renovation of older homes is making this the most desirable area of in-town. It is a sleepy quiet area near Edgartown Golf Course that still allows you to walk to shops, restaurants, pharmacy, grocery store, library and conservation trails. Come see why this home on town sewer and town water is best value in the Village today. Along with tool shed, artist shed, garage, full basement and landscaped yard it is a must see for those who want to live near all the action but want the quiet of a neighborhood. Easy to show and ready for immediate occupancy.

76 Norton Orchard Road

Country Living so close to Town! Lovely 3 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. Half Bath on the first floor. Interior stairs to lower level and garage. 3 Bedrooms 2 full baths on the 2nd floor. Many windows. High Ceilings. Hardwood Floors throughout. Small front porch to entryway on the first floor level. Lower level above ground office/living space with half bath.  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.

33 Alyssa Lane

ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start building your ISLAND DREAM 3 BR 3.5 home today! Execute a BUILDING CONTRACT or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty setting, 95 feet above Lagoon Pond. Enjoy sweeping sky views, colorful sunsets, and refreshing salty sea breezes. This outstanding building lot is among the last remaining opportunities in this thriving community. Utilities are already at the site, including town water, electric, and a private Amphidrome wastewater system, saving you the cost and inconvenience of a septic system. Lagoon Ridge borders acres of pristine conservation land, with easy access to scenic biking and hiking trails, providing the perfect blend of privacy and outdoor adventure. Located in desirable Oak Bluffs and central to all down-Island towns, this active and vibrant community is experiencing significant construction momentum. Don’t miss the chance to be part of this attractive neighborhood! Call for details and to schedule a tour of existing homes in Lagoon Ridge. Price is for the lot only; the home pictured is a sample of what can be built. Contact us today for a private tour of this exceptional offering!

2 Hopes Way

Charming, custom-built, 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, year-round ferries, and miles of ancient way trails through acres of conservation land. Well-maintained with many decorative details, features include a large primary bedroom, a convenient first-floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower—perfect for indoor-outdoor living. Beautifully maintained with wood floors, skylights, and natural light throughout, this move-in-ready home blends comfort, character, and charm. The floor plan offers privacy between the 3 oversized bedrooms. Ideal for year-round living or a seasonal retreat.

12 Wheelhouse Way

One-Acre Lot in a Peaceful Edgartown Neighborhood.

Build your island dream home on this spacious one acre lot, nestled in a quiet, centrally located Edgartown neighborhood. Enjoy the best of both worlds-a tranquil setting that's just minutes from town, beaches, and all the Vineyard's favorite spots.
This 3-bedroom lot offers excellent potential. Per the Board of Health, an enhanced septic system could increase the allowable lot capacity by 25% bringing the total to approximately 54,540 sq.ft.
The property abuts roughly 15 acres of unbuildable land, creating a peaceful, private backdrop of untouched natural beauty. 
Opportunities like this don't come around often-a serene location, central convenience, and plenty of room to design your ideal island retreat.

25 Coffins Field Road

ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start designing and building your dream 3BR + home today! Execute a BUILDING CONTRACT or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty setting, 95 feet above Lagoon Pond. Enjoy sweeping sky views, colorful sunsets, and refreshing salty sea breezes. This outstanding building lot is among the last remaining opportunities in this thriving community. Utilities are already at the site, including town water, electric, and a private Amphidrome wastewater system, saving you the cost and inconvenience of a septic system. Lagoon Ridge borders acres of pristine conservation land, with easy access to scenic biking and hiking trails, providing the perfect blend of privacy and outdoor adventure. Located in desirable Oak Bluffs and central to all down-Island towns, this active and vibrant community is experiencing significant construction momentum. Don’t miss the chance to be part of this attractive neighborhood! Call for details and to schedule a tour of existing homes in Lagoon Ridge. Price is for the lot only; the home pictured is a sample of what can be built. Contact us today for a private tour of this exceptional offering!

Build your dream home or homes on the special 7.1 acre private wooded property surrounding a beautiful 4.5 acre meadow in the grand Boldwater Association (BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach.  BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all convenient to town and airport. BWA amenities also include 2 tennis/pickleball courts and a boat launch which are both nearby. EDGARTOWN PLANNING BOARD APPROVED ON 10/22/25 A SUBDIVISION OF THE 14+ ACRES INTO TWO 7+ ACRE LOTS - North Lot 1 and South Lot 2.  The lots can be purchased together for $4,950,000 or separately for $2,490,000. Both lots enjoy full BWA membership rights and privileges.  The 2 lots will split ownership of the 4.5 acre meadow if sold separately. (see approved subdivision plan in DOCUMENTS)

3 Jacobs Neck Road (South Lot 2)

Build your dream home on the special 7.2 acre North lot 2 private wooded property with 1/2 ownership in the beautiful 4.5 acre meadow in the grand Boldwater Association(BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach.  BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all convenient to town and airport.  BWA amenities also include 2 tennis/pickleball courts and a boat launch which are both nearby. EDGARTOWN PLANNING BOARD APPROVED ON 10/22/25 A SUBDIVISION OF THE 14+ ACRE PROPERTY INTO TWO 7+ ACRE LOTS - North lot 1 and South lot 2.  The lots can be purchased together for $4,950,000 or separately for $2,490,000.  Both lots enjoy full BWA membership rights and privileges.  The 2 lots will split ownership of the 4.5 acre meadow if sold separately. (see approved subdivision plan in DOCUMENTS)

3 Jacobs Neck Road (North Lot 1)

Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance is the newly renovated Tisbury School! The interior delivers classic warmth, showcasing mellow wide pine floors in the living areas. Enjoy the convenience of an efficient kitchen with deck access, a cheerful updated bathroom, and cozy carpeted bedrooms. Need more space? The full, dry basement is a blank canvas, offering massive potential. This is your affordable opportunity to settle on Martha's Vineyard! Schedule your showing now!

51 Lantern Lane

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

0 Pennsylvania Avenue

Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs’ most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting.  A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the sought-after Meadow View Farms community, residents enjoy access to beautifully maintained common meadows, as well as association tennis and pickleball courts. The neighborhood’s peaceful setting fosters a true sense of community, while its prime location, just off the bike path, places Farm Neck Golf Club and all downtown attractions, within easy reach.

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7 South Meadow Lane

Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful beaches—including eligibility for Lambert’s Cove Beach access through West Tisbury residency.
The home exudes warmth and charm with vaulted ceilings, exposed brick accents, and beautiful natural wood beams throughout. The living and dining areas center around a classic wood-burning stove, creating an inviting gathering space that’s both cozy and functional. Off the living room, a sunlit three-season room provides a flexible area perfect for a home office, additional sleeping space, or art studio. A second three-season space off the kitchen offers versatility for use as a reading nook, den, or playroom.
Upstairs, you’ll find one traditional bedroom, a full bathroom, and an open loft-style bedroom that overlooks the living area—adding an airy, architectural feel to the home’s layout. The home includes two bedrooms and two full bathrooms and is currently designed with a three-bedroom septic system, offering flexibility and room for expansion.
Outdoors, the spacious 1.4-acre lot provides privacy, mature plantings, a fenced-in yard, an outdoor shower, and a back deck/patio area accessible from the living room, with ample room to enhance the property further. Buyers are encouraged to explore options for additional bedrooms, a guest house or detached bedroom, or even a pool. A small shed adds convenient storage or potential workshop use.
Thoughtfully priced and offered as is, with the buyer’s right to a home inspection. With its solid structure, Vineyard character, and exceptional location, this property presents a truly special opportunity for buyers seeking charm, character, and potential—whether envisioned as a year-round residence, smart investment, or quintessential island retreat.

25 Vineyard Meadow Farms Road

This Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to a peaceful and private deck. Living room offers a comfortable space for TV and relaxing. There is also nice size first floor primary with walk-in closet and spacious en-suite bathroom. The grand entryway takes you to the second floor which offers a second primary bedroom with walk-in closet and en-suite bath. There are two guest rooms that share a bath and second floor laundry. Wood and tile floors throughout, propane FHA with A/C. The walkout basement features 10'ceiling height and is ready to be finished off for additional living space, workshop or office.

151 Tashmoo Avenue

NEWLY LISTED | Build Your Katama Dream. 
Set in one of Martha’s Vineyard’s most sought-after locations, this newly created 1.5-acre parcel offers a rare opportunity to build your custom island retreat in the heart of Katama.

Perfectly sited near the pristine shores of South Beach, the level and conforming R60 lot provides endless potential for a main residence and an outdoor oasis designed to your vision.

Enjoy the peace and privacy of this exceptional setting while remaining just minutes from downtown Edgartown’s world-class dining, boutiques, and harbor front charm.

Listing agent must be present for all showings as this is private property.

39 Slough Cove Road (part of)

Move-in ready 3-bedroom, 1.5-bathroom house with a warm and welcoming interior. The main level includes an efficient kitchen,  living room, dining room with sliders to the mahogany deck and outdoor shower, 1 bedroom, laundry, and convenient half-bath. A one car garage is attached to the main level. The 2 large bedrooms and a full bath are located upstairs. Enjoy the private backyard with its well established perennial gardens, complete with a "she shed"—perfect for relaxing or entertaining. Great location on a paved road with easy access to kayaking, the bike path, Felix Neck, and Town.Title V has passed. Owner occupied- 24 hrs notice to show please.

14 Twenty First Street North

CREATE YOUR LEGACY ISLAND RETREAT IN THIS IDYLLIC LOCATION. Nestled within the entrance to Sweetened Water Farm, this 1.28-acre parcel represents a rare opportunity to create your own vision within one of Edgartown’s most sought-after settings. Located just one mile from the heart of historic Edgartown Village, this beautifully sited lot offers the ideal balance of privacy and proximity, surrounded by the natural beauty and pastoral elegance that define this storied neighborhood.

Whether imagined as a complement to the adjacent estate at 1/3 Louis Field or developed on its own as a distinctive Vineyard retreat, this property provides the perfect canvas for a custom residence tailored to your lifestyle. With scenic landscapes and timeless charm, 5 Louis Field invites you to become part of a place where refined country living meets coastal sophistication.

Create a signature home in one of Martha’s Vineyard’s most picturesque and desirable locales. This 1.28-acre parcel will support up to six (6) bedrooms with an enhanced septic system, per the Edgartown BOH.

5 Louis Field Road

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, multi-generational living, or a growing family. 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.

31 Tower Lane And 34 Ebens Lane

76 Norton Orchard Road

33 Alyssa Lane

2 Hopes Way

12 Wheelhouse Way

25 Coffins Field Road

2 Hopes Way

3 Jacobs Neck Road (South Lot 2)

3 Jacobs Neck Road (North Lot 1)

51 Lantern Lane

0 Pennsylvania Avenue

7 South Meadow Lane

25 Vineyard Meadow Farms Road

151 Tashmoo Avenue

39 Slough Cove Road (Part Of)

14 Twenty First Street North

5 Louis Field Road

22 Old Lighthouse Road

Featured Properties

31 Tower Lane And 34 Ebens Lane

76 Norton Orchard Road

33 Alyssa Lane

2 Hopes Way

12 Wheelhouse Way

25 Coffins Field Road

2 Hopes Way

3 Jacobs Neck Road (South Lot 2)

3 Jacobs Neck Road (North Lot 1)

51 Lantern Lane

0 Pennsylvania Avenue

7 South Meadow Lane

25 Vineyard Meadow Farms Road

151 Tashmoo Avenue

39 Slough Cove Road (Part Of)

14 Twenty First Street North

5 Louis Field Road

22 Old Lighthouse Road