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 for real vacation vibes!
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). Tisbury is thriving! 
Don’t miss this opportunity to live where design, comfort, and location converge.

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81 Leland Avenue

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Affectionately referred to as ‘The Treehouse', this property encompasses all the elements of a modern, sophisticated residence while providing the warmth and comfort of a private retreat. Professionally designed by Hutker Architects, this four-bedroom home, with a den/potential fifth bedroom, is sited in a private area, conveniently located with easy access to grocery store, pharmacy, and post office, and also to the island’s most beautiful beach at Lambert’s Cove. This home boasts meticulous attention to detail and exceptional craftsmanship. From the moment you step foot inside, you will notice the open floor plan design that creates a spacious and inviting atmosphere. Each of the four bedrooms has been thoughtfully designed and appointed to provide maximum comfort and privacy. The primary bedroom and ensuite bath and the den are at each end of the upper level, joined by a walkway across the living space.  The main level also features a bedroom with ensuite bath, in addition to the large, open kitchen/dining/living space.  Two more light-filled bedrooms plus a shared hall bath are located on the above-ground lower level. This is a meticulously maintained home with an open floor plan that is both functional and aesthetically pleasing. The open concept design includes a wood burning fireplace in the living room and a wonderful screened porch with open decks on either side. A back deck includes an outdoor shower.

14 Rebekahs Way

NEW CONSTRUCTION – Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island’s harbors, shops, and beaches.

Spread across two thoughtfully designed levels, the interiors are bathed in natural light, highlighting the clean lines, open spaces, and high-end finishes throughout. Highlights include a chef’s kitchen with Thermador appliances, a 9-foot island, and 7-inch oak flooring. The exterior is clad in timeless cedar shingles with crisp white trim, while expansive windows create a seamless indoor-outdoor connection.

A walk-out unfinished lower level provides the option for a home office, gym, or media room. The professionally designed landscape plan by Contemporary Landscape allows you to customize the outdoor experience—whether adding a fire pit, pool, or spa.

Perfect as a year-round residence, summer retreat, or investment property with strong rental potential, this home is truly an island gem. *Agent is owner.

34 Davis Street

Prime Commercial Building – Main Street, Vineyard Haven
Exceptional opportunity in the heart of downtown Vineyard Haven. This well-maintained mixed-use property offers over 3,100 sq ft of versatile space, featuring two ground-floor retail storefronts with excellent street visibility and two updated 1-bedroom apartments above—ideal for staff housing or rental income. A full basement provides flexible storage or utility space, and deeded rear access allows for deliveries and logistical ease. Recent updates include plumbing improvements and a fully renovated apartment. Whether you're an investor seeking steady income, a business owner looking for a flagship location, or a developer exploring mixed-use potential, this property delivers exceptional value in one of Martha’s Vineyard’s most desirable commercial corridors.

15 Main Street

Well-maintained three bedroom, 2 bath home on a level .51 acre lot. Primary en-suite and open floor plan offers the best in first-floor living. Large unfinished basement, outdoor shower and recent Title V inspection of the four bedroom septic system. Deck overlooks the spacious backyard with room for a pool. Convenient to shellfishing or kayaking in Sengekontacket, Caroline Tuthill Preserve and bike paths to Edgartown Village, Vineyard Haven or Oak Bluffs.

30 Teaberry Lane

Drone shots and virtual staging coming soon.
Welcome to 36 Ferro Way in beautiful Tisbury, MA! This stunning Colonial-style home, built in 2020, is where classic charm meets modern comfort. As you step onto the inviting farmer’s porch, you can immediately feel the warmth this home exudes.
Inside, spread out across 4,032 square feet of well-designed space, you'll find five spacious bedrooms and three and a half bathrooms. The main floor boasts a primary suite with an ensuite bathroom and a roomy walk-in closet—ideal for your personal retreat.
The heart of this home is its expansive eat-in kitchen, perfect for those who love to cook and entertain. Equipped with dual ovens and a gas stove, along with high-end cabinetry and elegant countertops, it's a chef’s dream come true. The kitchen flows seamlessly into the living areas, making it perfect for gatherings.
Need more space? Head up to the fully finished walk-up attic. Whether you envision it as a cozy lounge, home office, or play area, the possibilities are endless.
For those who appreciate convenience, this home features a central vacuum system and off-street parking. The outdoor space is equally impressive, offering a private area to relax and enjoy the serene surroundings.
Tile and carpet floors run throughout the home, adding both style and comfort. And when it comes to staying comfortable year-round, you'll appreciate the efficient heating and air conditioning systems in place.
Located near the vibrant amenities of Main Street, this home offers the perfect balance of peaceful living with easy access to shops, restaurants, and the marina.

36 Ferro Way

Nestled off Hidden Village Road on 2.1 private wooded acres, this spacious 4-bedroom, 2-bath home offers the perfect blend of peace and convenience—just 1.5 miles from Lambert’s Cove Beach and a short distance to Ice House Pond. Inside, enjoy an open-concept layout with cathedral ceilings, skylights, and an abundance of natural light. Sliding doors lead to a sunny, south-facing deck with tranquil woodland views. The main level features a large primary bedroom with an adjoining full bath, while the second floor includes a second spacious bedroom, full bath, and two additional guest bedrooms.
Additional highlights include a full basement with finishing potential, outdoor shower, large deck with awning, great yard, and hot tub. Located minutes from Up-Island Cronig’s, State Road Restaurant, West Tisbury Post Office, and Conroy’s Apothecary.

42 Hidden Village Road

Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows for a home of up to 1,850 sq. ft. of heated living space. Use as a seasonal residence or short-term rental is not permitted, ensuring a stable year-round neighborhood setting. Please note, the property may not be used as a seasonal residence or short-term rental. An excellent opportunity to design and build your future home on Martha’s Vineyard.

5 Candlemaker Circle

Enjoy dynamic, panoramic views from this charming and thoughtfully updated single-story Chappaquiddick cottage. Designed for effortless living, the home features an expansive deck overlooking the outer harbor and iconic lighthouse, perfect for entertaining or relaxation. A rooftop observation area provides additional seating and even more breathtaking vistas. Deeded beach access is conveniently located just across the way, offering a tranquil spot to enjoy the sandy shore and calm waters of the outer harbor. Ideally situated just off the Chappy Ferry, Manaca Hill offers the best of both worlds: easy access to the shops, dining, and vibrant charm of Downtown Edgartown, while embracing the laid-back, coastal lifestyle that makes Chappaquiddick so special.

23 Manaca Hill Road

Move-In Ready Raised Ranch – Just 1 Mile from Circuit Ave, Harbor Shops, Restaurants & Ferry Terminal!

Tucked away on a private side road, a rare find in this price range is ready for you to move in and make it your own! Whether you're looking for a year-round residence or a charming summer cottage, this home offers the ideal blend of comfort and convenience.

Step inside to an efficient single-level layout featuring an open kitchen and living area with hardwood flooring throughout. A spacious sunroom adds an additional 260 sq ft (not included in the total living area) and flows seamlessly onto the back deck, perfect for relaxing or entertaining.

The home includes three ample sized bedrooms and a renovated full bathroom, making everyday living easy. The walk-out lower level is a bonus, offering 960 sq ft of additional space with full-size windows and two egresses—ideal for a family room, home office and additional storage.
This is a must-see opportunity just minutes from everything Oak Bluffs has to offer!  *Town of Oak Bluffs will require cesspool to be upgraded upon sale. Very easy to show!

25 Windy Hill Road

Nestled in Katama, this vacation home offers easy access to South Beach, Edgartown Great Pond/Wilson’s Landing, and Edgartown Village. The property includes three bedrooms, two baths, a cozy living room with a fireplace, a kitchen, and a sunroom/dining area—ready for your personal touch.  An excellent opportunity for a relaxed Island lifestyle, second home, or vacation rental.

8 Court Street

Nestled in the heart of Katama and tucked away on a generous sized lot sits this four-bedroom, four-and-a-half-bath home offering an exceptional opportunity for year-round living or investment potential. Ideally located, there is easy access to both Edgartown Village and South Beach
The main level features an eat-in kitchen and a living room with a wood-burning fireplace.  There is separate dining area, a spacious first-floor bedroom suite, powder room, and laundry closet for convenience.
The upper floor includes a second primary bedroom suite with an oversized window allowing for lots of natural light, guest bedroom, sitting room, and hall bathroom. Additional potential awaits in the sizable unfinished basement.   
The grounds are meticulously landscaped. There is a stone patio with firepit and cozy front porch. The private backyard abuts association land, and no Vineyard home is complete without an outdoor shower.
Completing this offering is a detached two car garage. Above the garage is a sunny bedroom with high ceilings, sitting area, and full bath. 
Residents of this quiet subdivision enjoy association tennis courts. 
With its thoughtful layout and desirable location, this home provides the perfect blend of comfort and privacy for enjoying all that Katama has to offer.
Don’t miss this unique offering in a coveted neighborhood. Easy to show.
Being sold furnished with a few exclusions.

8 Old Dunhams Corner Way

This could be the best location in the Causeway Harborview Association with view of the pool and away from the busy road of Skiff Ave. Known for it's easy and close access to ferry, shops, and restaurants in Vineyard haven. With a king bed in one bedroom and the Queen bed with twin bunk on top allows for easy sleeping of 5 people. Living room has tile floors along with pergola floor in kitchen/bedroom. A great mix of year round and summer owners makes for a fun established community. Being sold furnished and ready for immediate occupancy. The community is a mix of year round, seasonal and rental units.

124 Skiff Avenue C-10

Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

10 Trotters Lane

Old World Vineyard Charm Meets Modern Katama Living. Welcome to this beautifully crafted Katama family compound, a private, thoughtfully designed estate offering timeless elegance and exceptional amenities. Nestled near Edgartown Village, this stunning property includes a four-bedroom main residence with three levels of living space, a charming two-bedroom guest house, pool house, pool, spa, stone patios, lush gardens, and multiple outdoor entertaining areas. Step into the main residence through a welcoming screened-in porch with dual entries. The main foyer leads to a light-filled great room, the heart of the home, featuring custom built-ins, a fireplace flanked by French doors, and sweeping views of the stone patio, pool, and gardens. The gourmet kitchen is open to the great room and features a central island, access to a mudroom, and a half bath. The formal dining area is complete with a wall of French doors that leads to the outside. Nearby, a first-floor bedroom currently serves as a richly appointed library, with custom built-ins, a compass rose medallion, and a bay window overlooking the back gardens. The first-floor primary suite is a private retreat, accessed through its own hallway with a built-in home office. The bedroom features a bay window, and the ensuite bath includes a soaking tub. Upstairs, a cozy lounge anchors two bedrooms and a full bath. An unfinished bonus room offers potential for expansion or serves as ample storage. The partially finished lower level includes a playroom with custom built-in seating and shelves, a second home office/lounge area, and a walk-in cedar closet. Unfinished areas provide more storage. The Outdoor Living: From the great room and dining room, step onto an expansive stone patio bordered by classic Vineyard stone walls. Multiple seating areas invite entertaining or peaceful relaxation, all with views of the pool, spa, and manicured gardens. The Guest House: The two-bedroom guest house offers complete privacy, with its own driveway, garden entrance, outdoor shower, and patio. The open-concept living space features a cathedral ceiling, French doors, and an eat-in kitchen. One bedroom is on the main level, alongside a full bath and laundry, while the second bedroom is upstairs. This guest house boasts a strong rental history. This unique Vineyard compound offers timeless elegance, privacy, and a stellar location, perfect as a year-round residence, summer retreat, or investment opportunity.

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19 Kitts Field Circle

Just over a mile from South Beach, this inviting Katama retreat is a perfect getaway. This sunlit home and detached living space offer three bedrooms and three baths, providing plenty of room for everyone. Set on a landscaped ¾-acre lot with pastoral views and peeks of the Ocean from the upper-level deck, the property features a wraparound deck for barbecues and a spacious backyard for games or stargazing. Conveniently close to Edgartown Village, the bike path, and the Field Club, it’s a wonderful spot to create lasting Vineyard memories.  A fourth bedroom is possible with a new enhanced system per the BOH.

19 Katama Drive

EDGARTOWN GEM: WALK TO TOWN + RELAX BY THE POOL.  Nestled just a short stroll from all the best of Edgartown Village, this beautifully renovated retreat offers the ideal balance of Vineyard charm and modern convenience. Designed across three levels of living spaces, the home provides a flexible layout that works beautifully for entertaining, relaxing, or hosting guests.

The main floor welcomes you with an inviting living room and a custom bar area complete with wine fridge and dishwasher—perfect for effortless entertaining. The covered porch offers a perfect spot for enjoying al fresco summer dining and relaxation. A sun-filled eat-in kitchen features a Viking gas range, granite countertops with a hint of sea glass green, and a built-in banquette overlooking both the covered front porch and the landscaped backyard. Also on this level, the primary bedroom offers private access to the pool terrace, creating a true indoor–outdoor retreat.

On the second floor, two well-sized bedrooms share a full bath, while the Lower Level offers additional space for gathering or guests, including a large lounge with media area, a bedroom and full bath, and a laundry room. A flexible bonus space currently functions as a home gym or valuable storage space, adding even more versatility.

Step outside to your private backyard oasis, where a heated 8x19 saltwater pool is framed by a stone terrace, professionally designed plantings, and evening accent lighting. The setting is equally suited to summer entertaining or quiet relaxation after a day at the beach.

Energy-efficient extras, including a rooftop solar array and an EV charging station, add to the home’s appeal. Offered with substantial core furnishings and boasting a strong rental history, this property is move-in ready and ideal as a year-round residence, seasonal getaway, or investment opportunity.

2 Orchard Lane

The historic Captain Ellsworth West House is a landmark property in the very heart of downtown Edgartown, offering an extraordinary combination of history, charm, and modern luxury. Just steps from Edgartown’s celebrated restaurants, galleries, shops, and harbor, this rare estate provides both the convenience of in-town living and the privacy of a graciously designed compound. The main residence spans more than 5,800 square feet and has been beautifully renovated over the years, blending contemporary updates with the timeless character of its historic architecture. On the first floor, an updated kitchen with a spacious pantry overlooks the pool, and flows into a welcoming living room anchored by a fireplace. The main living areas also include a more formal dining room with its own fireplace, and an elegant living room where French doors open to a covered porch. From here, sweeping views of the lush lawn and rows of hydrangeas create a quintessential Vineyard setting. Two staircases lead to the second floor, where the primary suite serves as a private retreat, complete with walk-in closets, an additional wardrobe closet, and a spa-like bath featuring a soaking tub. Two additional bedroom suites, each with private baths, along with a comfortable office space, complete this level. A third floor provides further accommodations with an additional bedroom and full bath, ideal for guests. The lower level is equally impressive, featuring a wine cellar, media room, guest bedroom, full bath, and laundry room. The property extends well beyond the main residence. A carriage house with a one-car garage provides additional storage and guest quarters and an expansive driveway accommodates ample parking rare for Downtown. The pool and spa form the centerpiece of the outdoor living space, surrounded by newly installed stone hardscape that adds elegance and durability. Adjacent to the pool, a thoughtfully updated cabana offers a kitchenette and half bath. Above the cabana, a recently renovated guest suite features a spacious bedroom and full tile bath, giving visitors a private and comfortable retreat. A remarkable property that embodies the very best of Edgartown living.

52 South Summer Street

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