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$2,678,000
4 Beds ⋅ 4 Baths ⋅ 22604054 MLS
Due to ongoing construction, the property may pose safety risks. Entry is at your own risk, and access is permitted only when accompanied by a licensed real estate agent. The agent of the buyer must be present at all buyer-client showings, inspections, and walkthroughs unless otherwise agreed to in advance by the listing agent.

31 Temahigan Avenue, Oak Bluffs
$6,150,000
6 Beds ⋅ 7 Baths ⋅ 73565263 MLS
Tucked away on a quiet street in coveted West Chop, this pristine property offers exceptional privacy, stunning scenery, and easy access to downtown Vineyard Haven. Designed for effortless indoor-outdoor living, this sophisticated compound combines timeless charm with every modern amenity. The first floor features an inviting open-concept layout ideal for both relaxed family living and entertaining. The kitchen overlooks the dining area, an intimate sitting area, and a versatile game and reading area beyond. The spacious TV and family room features custom built-in bookcases and French doors that open onto a bluestone patio and the pool area beyond. A generous screened porch provides additional living space. Completing the first floor is a large guest bedroom with an ensuite bath, along with a powder room, pantry, mudroom, and laundry room. Upstairs, the gracious primary suite features vaulted ceilings, a sitting area, and a luxurious bath with a soaking tub. There are two additional guest bedrooms, each with an ensuite bath. A private sun deck overlooks the pool and beautifully landscaped grounds, offering a wonderful spot to relax and enjoy distant water views. A dedicated office with water views toward Woods Hole and the Elizabeth Islands provides an inspiring setting for work or quiet retreat. Above the garage, a separate one-bedroom apartment offers a full kitchen, bath, and laundry, with convenient interior and exterior access. The living space in the apartment is currently being used as the sixth bedroom. Outside, the property transforms into a private oasis. The upper garden patio features an inviting sofa seating, while a stone staircase leads down to the heated 20' x 40' pool with spa. The expansive pool terrace is furnished with comfortable loungers and the pool cabana provides additional seating and a welcome retreat from the sun, all surrounded by lush, mature plantings. Other amenities include a gym, two enclosed outside showers and a pool powder room. With its exceptional privacy, generous living spaces, water views, pool and cabana, guest accommodations, this stunning property is truly one of the Grand Dames of West Chop.

59 Hagerty Drive, Tisbury
$2,850,000
6 Beds ⋅ 1 Baths ⋅ 22604053 MLS
Two side by side cottages built in 1945 Directly Pondfront on Sengekontacket with 180 degree views over the pond out to the Causeway, State Beach, Nantucket Sound and beyond. A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound and beyond. Set along the Boulevard, behind a traditional white picket fence, this .66 acre property features two side-by-side cottages dating back to the 1940s and captures the relaxed character of an earlier Vineyard. The larger cottage is a quintessential Vineyard retreat with beautiful direct waterviews from the Main living areas, dining area and porch. Upstairs, a sitting area and small upper deck provide exceptional views across Sengekontacket Pond to State Beach extending out towards Cape Cod. The porch and the spacious lush side yard with lawn and lovely plantings, offer an inviting setting for morning coffee, summer dinners, entertaining, or simply enjoying the changing light and activity on the water. The larger cottage has an established rental history. An attractive option for seasonal rental income. The second smaller cottage offer the opportunity for a new owner to renovate and make the space their own as additional living space, a guest cottage or studio, subject to applicable approvals. Another compelling option is to explore removing the cottages and combining the existing square footage together with a percentage of additional square footage as allowed, to create one larger residence to take full advantage of this extraordinary waterfront setting. Any renovations, expansion or redevelopment would be subject to all applicable approvals and zoning regulations. Additionally, just a stone's throw away, the nearby boat landing provides convenient access to the pond, with openings into the Nantucket Sound, for launching kayaks, paddleboards and trailered boats. putting one of the Vineyard's most beautiful waterways practically at your doorstep. With two cottages, acreage, established rental history, convenient boating access and remarkable views.#49 The Boulevard offers a special opportunity to enjoy a classic Vineyard property today while imagining and planning its possibilities for the future.

49 The Boulevard, Edgartown
$3,650,000
73565039 MLS
Set in the heart of Katama, this exceptional 5.5-acre building lot offers a rare opportunity to create a private island retreat surrounded by nature and conservation land. The property is bordered by 87 acres of Sheriffs Meadow conservation land and an additional 75 acres of town-owned land, providing an extraordinary sense of privacy and protected open space. Located in a well-established Katama neighborhood, the property captures the essence of the island lifestyle, with the sights, sounds, and salt air of the Atlantic Ocean close by. Just minutes from South Beach and Wilson’s Landing, easily enjoy swimming, boating, fishing, and long summer days by the water. A remarkable opportunity to build in one of the Vineyard’s most coveted settings, with expansive protected land and the beauty of Katama all around.

8 Turkeyland Cove Road, Edgartown
$4,725,000
3 Beds ⋅ 5 Baths ⋅ 73564664 MLS
Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home’s comfortable, refined character, while a thoughtfully designed single-level layout offers the ease and convenience of true first-floor living, with a private primary suite and separate guest wing providing an ideal sense of space and privacy. The detached studio with workshop is a hobbyist’s dream, overlooking the pool and offering a versatile space for creative pursuits, hobbies, or use as a pool cabana.

149 Litchfield Road, Edgartown
$2,200,000
2 Beds ⋅ 2 Baths ⋅ 22604013 MLS
This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom main house is complemented by a spacious two-bedroom, one-bathroom guest studio with a fireplace, offering a combined 3,771 square feet of living space. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up and down Island destinations. Future expansion to 12 bedrooms is possible with a septic upgrade, although the current system meets all regulations. Enjoy effortless access to Lambert's Cove Beach, 7a Foods, North Tisbury Farm, State Road Restaurant, and all the iconic West Tisbury landmarks.

99 Oak Lane, West Tisbury
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 73564420 MLS
This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious two-bedroom, one-bathroom Guest Studio with a fireplace, offering a combined 3,771 square feet of living space. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up and down Island destinations. Future expansion to 12 bedrooms is possible with a septic upgrade, although the current system meets all regulations. Enjoy effortless access to Lambert’s Cove Beach, 7a Foods, North Tisbury Farm, State Road Restaurant, and all the iconic West Tisbury landmarks.

99 Oak Lane, West Tisbury
$1,350,000
2 Beds ⋅ 2 Baths ⋅ 22604010 MLS
Discover the charm of West Tisbury with the perfect blend of country living and village convenience. Ideally located just a short stroll from the heart of town, you'll enjoy easy access to all the West Tisbury Village has to offer. Set on a lovely lot, the home features a spacious southeast-facing deck overlooking a sunny yard. Four detached outbuildings. A generous south-facing living room is filled with natural light and offers peaceful views of the surrounding landscape. The kitchen provides an opportunity to create a space tailored to your vision. Off the kitchen is a large dinning area with a beautiful custom cabinet. The primary suite includes a sitting area and sunroom, while a second bedroom off the front entry features a half bath and access to the outdoor shower. Although the home is currently configured as a two-bedroom residence, it is served by an existing four-bedroom Title V septic system. This property presents an exceptional opportunity for buyers looking to renovate and make a home their own. Heating is provided by a mini-split systems. The expansive outdoor living areas blend seamlessly with the natural surroundings. The house is being sold in as-is condition.

29 Scotchmans Lane, West Tisbury
$2,995,000
4 Beds ⋅ 2 Baths ⋅ 22604007 MLS
WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock.

27 Beach Road, Oak Bluffs
$2,500,000
4 Beds ⋅ 3 Baths ⋅ 73564299 MLS
Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

9 Codman Spring Road, Edgartown
$1,895,000
3 Beds ⋅ 2 Baths ⋅ 22603999 MLS
Rarely does such a unique, waterfront location become available. With amazing, 180+ degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Wake up to glorious sunrises. Be entertained by a variety of waterfowl throughout the seasons. Have your vessel at the ready right off the shore. The moment you walk onto the property, the tranquil feel and the cooling shade trees will make you forget that you are still so close to town and ferry. The property is hugged by the Lagoon on one side and Vineyard Haven Harbor across the street on the other. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private water access, is a year-round home with breathtaking, expansive views up and across the lagoon. The upper level has a spacious deck overlooking the gardens and sweeping views of the lagoon. The waterside patio has beautiful perennial gardens. A canopy of mature shade trees keeps the property cool. Enjoy meals al fresco in the shade while enjoying the water views. There are many creative details throughout. The sellers have been actively making improvements to increase the commercial usage. Soon the be an art gallery, the commercial building is currently used as an artist's studio. Built with SIPS construction, this building is energy efficient and wind resistant. Property is connected to the town sewer and town water. Please note: This property is being sold "as is". Buyer is responsible for completing the necessary due diligence with the town and an engineer about this unique property that offers a plethora of opportunities.

129 Beach Road, Tisbury
$3,875,000
5 Baths ⋅ 73564126 MLS
EXCEPTIONAL MIXED-USE INVESTMENT AND OWNER-OCCUPANT OPPORTUNITY JUST MINUTES FROM HISTORIC EDGARTOWN ON BEAUTIFUL MARTHA'S VINEYARD! This meticulously maintained 6,712 SF property offers three commercial units plus a residential apartment with an additional side attic future expansion potential to add an additional apartment. Commercial spaces include a dental practice with finished lower level (full bath, kitchenette, living area & bedroom, and storage room), a Pilates studio with reception area, two studios & half bath, and a commercial catering kitchen with a full basement prep/expansion kitchen and half bath. The spacious 1+ bedroom condo features open-concept living, kitchen, bonus room (area with built in couch/bed) & full bath. Unfinished attic includes architectural plans for a second residential apartment - enhancing future value and income potential. Ideal for medical, dental, restaurant, wellness, professional offices, retail, creative studios or investors. Property has town water and sewer - a great bonus. Ample on-site parking, flexible layout, and an outstanding Edgartown location just outside the Historic District.

258 Edgartown-Vineyard Haven Rd, Edgartown
$3,100,000
3 Beds ⋅ 1 Baths ⋅ 73564072 MLS
HINES POINT WATERFRONT GEM with 85 feet of frontage on the Lagoon, offering ever-changing water views and the perfect vantage point to watch the Steamship Authority ferries arrive in Vineyard Haven Harbor. Enjoy the charming, timeless cottage with a one-car garage as an idyllic summer retreat, or bring your Vineyard vision to life with beautiful architectural plans by Sullivan +Associates Architects. Perched atop a gentle embankment, this exceptional property captures expansive views of the Lagoon, harbor, and town. A private staircase leads to the water's edge, where you can launch a kayak, paddle board, or small boat and explore the Lagoon and beyond. Just a short stroll to the Martha's Vineyard Museum, downtown Vineyard Haven, shops, restaurants, and the ferry, this is a rare opportunity to own in one of the Island's most coveted waterfront locations.

36 Hines Point Rd, Tisbury
$1,195,000
3 Beds ⋅ 2 Baths ⋅ 22603994 MLS
Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you'll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha's Vineyard so special. Martha's Vineyard Hospital is also just a short two-minute drive away. Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The roof is approximately 10 years old, and recent improvements have focused primarily on the basement, where the space has been transformed to expand the home's usable living and recreational area. Whether you envision a TV room, game room, home office, exercise area, or a combination of uses, there are plenty of possibilities. A newly completed "doghouse"-style exterior basement entry provides convenient direct access to the lower level. The first and second floors would benefit from a little TLC and personal touches to brighten and refresh the space, providing a great opportunity for the next owner to make the home their own. Outside, the property offers a small, manageable yard with off-street parking, along with a classic Vineyard outdoor shower—a favorite feature after a day at the beach and something many consider a must-have for Island living. Set on a 5,000-square-foot lot, the property offers the best of both worlds—a quieter location at the Eastville side of Winemack Street while still being just minutes from downtown Oak Bluffs. Title 5 System failed, Seller is offering a credit at closing to cover costs(to be determined). Prequalification letter from your lending source or proof of funds required. Owner and tenants currently occupy the home; 24-hour notice for showings is preferred.

2 Winemack Street, Oak Bluffs
$1,255,000
3 Beds ⋅ 2 Baths ⋅ 22603967 MLS
Nestled on a cul-de-sac is this sweet 3 bedroom ranch. Located on a .34 acre lot with plenty of room to expand this solid home and still have enough space for an ADU on this spacious lot. Well maintained over the years with recent upgrades including, roof, siding, new insulation, flooring and paint. Natural light floods the house from the bank of windows in the living room to the sliding glass doors in the dining area leading to the deck. A spacious garden shed with a front porch and electricity complete the yard. Plenty of room for a nice pool to make those summer days extra special.

11 Stanley Street, Oak Bluffs
$1,800,000
4 Beds ⋅ 4 Baths ⋅ 73563290 MLS
Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and bedroom—perfect for extended family or guests. There are two driveways. The home also features a garage and a finished basement offering excellent storage or future expansion potential. A detached studio at the rear of the property provides wonderful overflow space for a home office, art studio, or guests. The property is only 2/10ths of a mile to the town beach at the end of Grove Ave, and half a mile to the town beach on Owen Little Way. Ready for a new owner's vision and updates, this well-located property presents an exceptional opportunity to enjoy the convenience and charm of this desirable neighborhood. This property is being offered "as-is." *Please note there is only AC in the primary bedroom wing addition.

528 Main Street, Tisbury
$12,250,000
7 Beds ⋅ 4 Baths ⋅ 73563263 MLS
You truly can have it all—just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village, yet set along one of the most spectacular stretches of beach, with a 190’ private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of the harbor. Inside, casual elegance defines the home, with a seamless blend of gracious formal spaces and inviting areas for relaxed gatherings. An enclosed porch opens onto a spacious deck overlooking the harbor, creating the perfect setting to take in picture-worthy sunsets, the beloved Fourth of July fireworks display, and the ever-changing scenery. The grounds are equally captivating, made even more exceptional by the inclusion of 75 Landing Place Road and a beloved clay tennis court framed by sweeping water views. Cherished by the same family for generations, this extraordinary waterfront compound is a truly special place.

139 Chappaquiddick Road, Edgartown
$1,225,000
1 Beds ⋅ 2 Baths ⋅ 22603763 MLS
This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment. The home features a bright, open-concept kitchen, dining, and living area with beautiful hardwood floors that create a warm and inviting atmosphere. A first-floor den, complete with a daybed, provides flexible space for two additional overnight guests, while a full bathroom on the main level adds convenience. Sliding glass doors from the dining area open to a spacious deck overlooking the beautifully landscaped gardens, creating the perfect setting for outdoor dining, entertaining, or simply relaxing. Additional outdoor amenities include a hot tub and an outdoor shower, allowing you to fully enjoy the Vineyard lifestyle. Upstairs, you'll find a spacious primary bedroom, a large open loft that can serve as an additional living or sleeping area, and a second full bathroom. Adding even more value, the home is equipped with transferable solar panels .

323 County Road, Oak Bluffs
$1,600,000
4 Beds ⋅ 3 Baths ⋅ 22603890 MLS
A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you will find two large bedrooms, a full bathroom with walk-in shower and plenty of attic storage. Set on a picturesque two-acre parcel, the property also features a detached 384-square-foot studio, offering exceptional flexibility. Set back and private from the main house, it is independent and private with its own parking area, yard, and septic system, it presents wonderful possibilities for hosting family and friends or creating a private artist's studio or home office. Ideally located just minutes from Nip 'n Tuck Farm, Up-Island Cronig's Market, Conroy's Apothecary, and Main Street in Vineyard Haven. As a West Tisbury resident, you'll also enjoy access to the coveted Lambert's Cove Beach with a resident permit, one of Martha's Vineyard's most treasured shoreline beaches. *Estate Rules Apply

150 Field View Lane, West Tisbury
$1,795,000
3 Beds ⋅ 3 Baths ⋅ 22603889 MLS
Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming living room, anchored by a pristine Vermont Castings wood stove, opens seamlessly to a covered porch and spacious deck--perfect for morning coffee or evening gatherings. The spacious first-floor primary suite provides a private retreat with two en-suite baths and two walk-in closets. Upstairs, you'll find two bedrooms with beautiful wood floors, built-in drawers, and cabinets that add both charm and functionality to the rooms. These bedrooms share a hall bath, making the second floor an ideal space for family or guests. A generous bonus room above the garage offers flexible space for a home office, gym, or additional sleeping quarters. A separate studio on the property adds further versatility.

174 Middle Road, Chilmark
$16,250,000
6 Beds ⋅ 8 Baths ⋅ 22603861 MLS
Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets. The home centers on a soaring great room with 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, chef's kitchen, and walls of glass opening to the landscape. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room. Across the lawn, a finished barn offers flexible guest and entertaining space, a loft with full bath, and three-car garage. Open meadows, exceptional privacy, and private paths lead to Great Rock Bight, while the five-member association offers an additional 100 feet of private beach with a bluff-top camp and fire pit. Chilmark's Lucy Vincent and Squibnocket beaches and Menemsha village complete this rare up-island offering.

25 Brickyard Road, Chilmark
$1,995,000
5 Beds ⋅ 3 Baths ⋅ 73560676 MLS
Ideally situated just minutes from the ferry, downtown Vineyard Haven, and West Tisbury, this charming, meticulously maintained property offers exceptional flexibility for year-round living, seasonal escape, or income potential. The main residence features three bedrooms and an inviting open-concept floor plan, seamlessly connecting an updated kitchen, living room, and dining area, perfect for entertaining or relaxed island living. Expansive decks extend the living space outdoors, overlooking mature plantings and beautifully established garden areas throughout the property. The home is powered by an owned 5kw solar panel system serving the entire property, offering energy efficiency and reduced utility costs. Agent has a list of detailed upgrades upon request. Adding remarkable versatility, a 900 square foot barn style studio offers space for a home office, artist's studio, workshop, or creative retreat, while a private two bedroom garden apartment, complete with its own separate entrance, provides excellent rental income potential or comfortable accommodations for extended family and guests. Ample parking and move-in ready condition round out this rare combination of location, character, and income producing flexibility on Martha's Vineyard. Please note: the property is located within the Vineyard Haven watershed, and a new or upgraded nitrogen-mitigating septic system will be required.

135 Mayflower Lane, Tisbury
$3,225,000
3 Beds ⋅ 5 Baths ⋅ 73560514 MLS
Hidden behind a veil of privacy on a generous coastal sanctuary, an extraordinary property waits to be discovered. This custom masterpiece blends timeless architecture with a modern, elusive sophistication, offering comfortable finished living space within an impressive total structure. Cross the threshold onto rich hardwood floors where light dances beneath a dramatic cathedral ceiling, drawing you toward a luxurious modern kitchen and the quiet warmth of a central masonry fireplace. Secrets unfold across multiple levels, from a secluded bonus room to an expansive lower level offering basement space—including 624 square feet of finished living space perfectly suited for a private lounge, studio, or hidden sanctuary. Climate is effortlessly controlled through central air conditioning and gas forced hot air, ensuring year-round comfort. Yet the true mystery of this property lies just beyond the newly renovated exterior siding and doors: a private outdoor paradise completely shielded from the outside world. Here, summer days dissolve into long, twilight evenings around a pristine 18' x 38' in-ground gunite pool, framed by a sprawling entertaining patio, an intimate gazebo, a 693-square-foot wooden deck and an essential outdoor shower. Anchored by an attached two-car garage, a powered shed and a classic gravel driveway, this renovated haven isn't just a home—it is a private world waiting for those who live extraordinary lives.

8 Woodhaven Dr, Edgartown
$425,000
73560451 MLS
Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails, town beaches, and ferry landings. Bring your vision, architect, and builder to create a bespoke sanctuary in one of the Vineyard's most vibrant communities.The property is limited to 1 bedroom and has no Title V bathroom limit.

Heather Ln, Oak Bluffs
$2,695,000
5 Beds ⋅ 4 Baths ⋅ 73560291 MLS
Historic Water View Elegance Meets Modern Luxury in Vineyard Haven: Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in contemporary living. There are 5 total bedrooms, 2 on the first floor and 3 on the second floor. There are 2 en suite bedrooms, 1 on the first floor and 1 on the second floor. In addition, there are 4 full bathrooms (3 newly renovated), and a light-filled, spacious kitchen, designed to blend old world charm with modern needs. Additional updates include central air conditioning, 3 lined chimneys, and an upgraded septic system. A bluestone patio is ideal for al fresco dining and summer barbecues. And a lovely, professionally maintained backyard and garden complete the storybook picture. Perfectly positioned right across from picturesque Owen Park, this property places you at the very heart of Vineyard Haven culture and coastal convenience. Take in water views and the boat activity of scenic Vineyard Haven Harbor. Enjoy front-row access to Owen Park with the newly built town dock and the historic bandstand where you can enjoy the Vineyard Haven Band play Sunday evenings in the summer. When you want to explore further, you are a short walk from the village where there are several exciting new restaurants, a multitude of shops, and the historic Playhouse. Whether you are looking for a gracious year-round island residence, a seasonal getaway, or a desirable vacation rental income producer, this historic gem delivers on every front. Schedule your private tour today and experience the magic of Vineyard Haven living. Offer mostly furnished and equipped with some exclusions.

124 Main St., Tisbury
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 73559452 MLS
CHAPPAQUIDDICK – Opportunity awaits on this conforming 3-acre parcel, featuring a year-round home with a 5-bedroom septic system, offering exceptional potential for future expansion, including a guest house. Privately tucked away off the main road, yet conveniently located just minutes from the Chappaquiddick Community Center, the Ferry, Wasque Beach, and Quammox Preserve with its public access to Katama Bay, this property is perfectly positioned to enjoy the best of Chappy. Abutting conservation land, with the Cross Chappy Trail and Pocha Pond Reservation just outside your door, it offers direct access to some of the island's most treasured natural landscapes. The home's efficient floor plan features a first-floor bedroom, open living spaces, and a cozy sunroom, creating the perfect retreat to enjoy all that Chappaquiddick has to offer today, while providing outstanding opportunities for future expansion.

8 Pip'n Circle, Edgartown
$1,285,000
3 Beds ⋅ 3 Baths ⋅ 73559180 MLS
Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this beautifully maintained three-bedroom home combines distinctive character with thoughtfully updated spaces, modern comforts, and a peaceful residential setting. The home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An updated custom kitchen by French Accent, with a walk-in pantry, opens to the dining area, while a first-floor powder room with laundry adds everyday convenience. A substantial 2010 addition expanded the home with a spacious, light-filled living room and a generous second-floor primary suite. Two additional bedrooms and a full bath comfortably accommodate family and guests. Outside, a large deck overlooks landscaped grounds with native plantings, stonework, and a fire pit gathering area. A full walk-out basement is perfect for both a work space and storage. Whether you’re searching for a year-round home, vacation retreat, or investment opportunity, this property offers something increasingly rare on Martha’s Vineyard: a home with genuine character, generous living space, and the comforts of modern living.

41 Cook Road, Tisbury
$4,125,000
7 Beds ⋅ 5 Baths ⋅ 22603630 MLS
An Inspirational Oasis -- Nestled along the gentle slopes of Indian Hill, this secluded three-dwelling compound offers more than three acres of exceptional privacy where rural tranquility meets effortless island living. Centered around a heated saltwater pool, the main house, studio barn, and guest house provide 4,464 square feet of living space surrounded by wildflower meadows, perennial gardens, mature trees, and sweeping lawns. The sun-filled main house features a timeless stone fireplace, inviting living and dining spaces, and a thoughtfully designed kitchen, all oriented toward picturesque garden views. The Studio Barn offers exceptional flexibility for creative pursuits, wellness, guests, or multigenerational living. The two-story Guest House includes three bedrooms, one-and-a-half baths, and a loft-style living area. Together, the property offers seven bedrooms, four-and-a-half baths, and remarkable versatility. Owners enjoy access to Lambert's Cove Beach, Long Point Beach & Wildlife Refuge, nearby farm stands, village amenities, trails, bike paths, and Cedar Tree Neck Sanctuary. Three Dwellings. One Property. Endless Possibilities.

31 Josiah Sachem Way, West Tisbury
$1,750,000
3 Beds ⋅ 4 Baths ⋅ 22603069 MLS
GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate entrance for an in-law or ADU. 1st FL en suite BR & a common half bath at the foyer entry. Large kitchen w/ full appliances & a 10' stone topped island for large gatherings. Gas fireplace in the family room, sliders to rear yard, a well-designed mudroom area w/ 1st FL laundry, large overflow pantry & a built in bench seating area. The 2nd FL offers 2 en-suite BRs, w/ a large common area. Close to the Lagoon & Sailing Camp Park.Short ride downtown- ideal for year round occupancy and/ or high season rentals. House related plans, professional photos, interior, exterior & aerial video avail upon request.

28 Grovedale Road, Oak Bluffs
$1,745,000
2 Beds ⋅ 1 Baths ⋅ 22603245 MLS
Oceanfront Cottage on .21 acre of waterfront property and over 50ft of shoreline on East Chop. Wake up to breathtaking ocean views and the soothing sound of waves from this charming two-bedroom oceanfront cottage. Perfectly positioned along the shoreline, this inviting coastal retreat offers the rare opportunity to own a slice of waterfront paradise. Designed for relaxed seaside living, the home features a bright, open living area filled with natural light, a eat-in kitchen, and two comfortable bedrooms that provide a peaceful escape after a day by the water. Expansive windows frame spectacular ocean vistas, while a spacious open porch is ideal for morning coffee, sunset dinners, or simply enjoying the ever-changing seascape. Whether you're looking for a vacation getaway, or an investment property, this cottage offers timeless coastal charm in an unbeatable location. Just imagine what you could build on this magnificent property.

11 Beach Road, Oak Bluffs

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