Refine Search
Map
Sort by
72 Chappaquiddick, Edgartown
$2,950,000
8 Beds ⋅ 7 Baths ⋅ 73586117 MLS
Perched atop the highest point on Chappaquiddick, this private compound truly has it all, while still being a short distance from Chappy favorites including the Community Center, Beach Club, Ferry, and Slip Away Farm. Designed for both relaxation and recreation, the property offers endless ways to enjoy time with family and friends. Spend the afternoon on the sports courts, cool off at the pool, or relax on one of the expansive porches or patios. The guest house provides additional space and privacy. The pool house, complete with a half bath and kitchenette, makes entertaining effortless, with everything you need close at hand. A separate gym and game room offer even more ways to stay active or unwind, whatever the weather. With a strong rental history, the property also presents an excellent investment opportunity, while its generous amenities and multiple living spaces make it an ideal generational home to be enjoyed for years to come.

72 Chappaquiddick, Edgartown
no property photo
$1,995,000
4 Beds ⋅ 3 Baths ⋅ 22605031 MLS
Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite. Total square footage represents house (1,400 sq. ft.) and guest house (518 sq. ft.). A shared six (6) bedroom septic system services both houses. 2 miles to Lucy Vincent beach

25 Fulling Mill Road, Chilmark
no property photo
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 22605017 MLS
A peaceful retreat close to Edgartown's amenities, thoughtfully updated and refreshed with a new kitchen and light-filled living spaces, this four bedroom three bath home offers an easy, relaxed setting for family and guests. The main body of the home features one downstairs bedroom with two additional bedrooms upstairs plus a flex space with balcony, and a fourth bedroom with full bath and kitchenette located above the attached garage for a separate guest retreat. The walkout basement provides storage, laundry and future potential. A versatile property thoughtfully designed for comfortable year-round living and quintessential Vineyard summers. Bold Meadow community tennis & pickleball courts nearby and abutting State forest bike path and hiking trails right from your back door.

42 Bold Meadow Road, Edgartown
42 Bold Meadow Road, Edgartown
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 73585957 MLS
A peaceful retreat close to Edgartown's amenities, thoughtfully updated and refreshed with a new kitchen and light-filled living spaces, this four bedroom three bath home offers an easy, relaxed setting for family and guests. The main body of the home features one downstairs bedroom with two additional bedrooms upstairs plus a flex space with balcony, and a fourth bedroom with full bath and kitchenette located above the attached garage for a separate guest retreat. The walkout basement provides storage, laundry and future potential. A versatile property thoughtfully designed for comfortable year-round living and quintessential Vineyard summers. Bold Meadow community tennis & pickleball courts nearby and abutting State forest bike path and hiking trails right from your back door.

42 Bold Meadow Road, Edgartown
12 Boldwater Road, Edgartown
$9,950,000
8 Beds ⋅ 11 Baths ⋅ 73584420 MLS
A winding approach through 9.8 acres sets the tone for 12 Boldwater Road: a private Edgartown estate of uncommon scale and distinction. At its heart stands a seven-bedroom, ten-bath residence designed by Robert A.M. Stern. A gracious foyer introduces light-filled interiors, a dramatic post-and-beam living room, multiple fireplaces, and a gourmet kitchen equally suited to intimate dinners and large gatherings. The grounds offer the ease of a private resort. Spend the day beside the heated 20' x 60' pool, or retreat to the pool house with an exterior hot tub, complete with a fully equipped gym, sauna, massage room, and screened porch with fireplace. Every element of the property invites a slower, more considered way of living on the Vineyard. The Boldwater Association membership adds access to a private ocean beach, boat landing, tennis, and pickleball courts. Together with the estate’s remarkable privacy, these amenities offer a compelling balance of seclusion and coastal recreation. Architectural heritage, expansive land, and a setting designed to be enjoyed across generations make 12 Boldwater Road an extraordinary Vineyard offering.

12 Boldwater Road, Edgartown
24 Myober Ln, Edgartown
$2,995,000
4 Beds ⋅ 5 Baths ⋅ 73583186 MLS
In a beautiful coastal setting, this 4-bedroom, 4.5-bath wood-sided contemporary is perched on 1.8 private waterfront acres in Major’s Cove, with frontage on Sengekontacket Pond, and offers a functional floor plan with exceptional views. Expanded over time, the home now includes a primary suite and laundry on the main living level, with comfortable living spaces opening to expansive wraparound decks. The home offers approximately 3,148 square feet of finished space, including approximately 800 square feet on the finished lower level, with substantial above-grade exposure at the rear. An upper-level ensuite bedroom and two additional bedrooms with two full baths on the lower level provide flexibility for family and guests. Improvements include newer windows and doors, new mini-split systems, new hot water heaters, and work to several bathrooms. The September 2026 Title V inspection passed and supports a five-bedroom septic capacity. With town water, only one existing structure on the 1.8-acre parcel, and substantial acreage, the property may offer long-term potential for expansion or future improvements, subject to applicable approvals. Life at Major’s Cove includes access to tennis and pickleball courts, a community boat launch, and kayak storage. HOA services include private-road maintenance, snow removal, and common-area landscaping. Whether enjoyed as a peaceful waterfront retreat or a home with room to evolve over time, this property offers exceptional privacy, versatility, and a distinctive island setting.

24 Myober Ln, Edgartown
32 Norton Orchard Rd, Edgartown
$1,850,000
4 Beds ⋅ 6 Baths ⋅ 73582365 MLS
Discover this turnkey Edgartown home in a prime location near downtown dining and shopping, Edgartown Golf Club, and popular beaches. The refreshed interior features modern flooring, modern LED lighting, bathroom, and a bright kitchen with dark green granite countertops, tall windows, and a vaulted ceiling. All bedrooms have private en suite full baths, with two bedrooms on each floor. A sunroom opens to the deck and spacious backyard, offering room to relax or entertain. The home has town water and sewer and is being sold turnkey, excluding books and select personal items. Easy to show. This property is part of a First Look program. It allows owner occupant buyers to have their offers negotiated on day 8 of being listed. Owner occupants are those buyers that will occupy the property as their principal residence within 60 days of closing and will maintain their occupancy for at least 1 year. These buyers are required to sign an Owner Occupant Certification as part of the contract. An investor, trust, vacation or part-time residence, or purchasing for another person will be considered an Investor and are not eligible for First Look. Investors are welcomed to make offers the initial 30 DOM, but will not be countered until day 31. Some images in this listing have been virtually staged

32 Norton Orchard Rd, Edgartown
98 Edgartown Bay Rd, Edgartown
$4,995,000
4 Beds ⋅ 5 Baths ⋅ 73581090 MLS
COASTAL LUXURY IN KATAMA — EXCEPTIONAL LIVING NEAR SOUTH BEACH. Set in one of Katama’s most coveted locations, where the sound of the ocean drifts in and South Beach is within easy reach, this distinctive coastal contemporary was thoughtfully designed to maximize natural light, energy efficiency, and long-term flexibility.The reverse-style floor plan places the main gathering spaces on the upper level, where abundant windows fill the interiors with sunlight and frame distant views across the lower reaches of Katama Bay. The open-concept Living, Dining, and Kitchen areas flow seamlessly together, creating an inviting setting for relaxed Vineyard living and effortless entertaining. At the heart of the home, the oversized Chef’s Kitchen opens directly onto a spacious porch for outdoor dining, gathering, and lounging, while two additional porches further extend the living space. The upper porch also enjoys seasonal views of the Edgartown fireworks, and nearby Fisherman’s Wharf and the public boat landing offer convenient access to Katama Bay and Edgartown Harbor.The home features four light-filled en suite bedrooms, each with a private bath and spacious shower. The generous Primary Suite includes dual oversized closets, a walk-in shower, and a private water closet. A bright first-floor bonus room offers flexible use as a Den, In-Home Gym, yoga studio, or additional guest space, with sliding glass doors for privacy, its own porch, and an adjacent half bath.Future accessibility was incorporated into the original design through a fully framed, wired, and mechanically prepared elevator shaft, allowing for the potential installation of an elevator with minimal disruption.Offered turnkey with indoor and outdoor furnishings and an established rental history, 98 Edgartown Bay Road is equally compelling as a personal Vineyard retreat, an income-producing investment, or a combination of both. The property also offers room for a future swimming pool and detached garage, subject to local approvals. Thoughtfully conceived for entertaining, sustainability, accessibility, and lasting enjoyment, this exceptional Katama residence presents a rare opportunity just moments from South Beach.

98 Edgartown Bay Rd, Edgartown
1 Mariners Way Unit A, Edgartown
$1,399,000
1 Baths ⋅ 73580947 MLS ⋅ ["Mariner's Landing"] BLDG.
A standout commercial offering in Edgartown, combining striking contemporary design with exceptional flexibility. Located just outside the historic district and just shy of 2,000 square feet, this commercial condominium offers a beautifully finished, thoughtfully designed interior that feels anything but ordinary. Soaring ceilings, polished concrete floors, dramatic black architectural details and walls of glass create a sophisticated, light-filled space with a modern industrial aesthetic. The versatile layout features an open reception or showroom area, multiple private rooms, a glass-enclosed conference room, additional work areas, and a half bath, allowing the space to adapt easily to a variety of business needs. A full 1,520± square foot basement provides substantial expansion, storage and utility space. Central heat and air conditioning, fire sprinkler system, town water and sewer, on-site parking and a dedicated loading area add everyday convenience and functionality. Renovated in 2021 with an uncommon level of style and attention to detail, this is a compelling opportunity for an owner-user or investor. The Master Deed allows for a broad range of commercial uses, subject to Edgartown zoning and other applicable regulations and restrictions.

1 Mariners Way Unit A, Edgartown
234 County Road, Oak Bluffs
$1,375,000
5 Beds ⋅ 2 Baths ⋅ 73580264 MLS
Surprisingly roomy Cape-style home, centrally located in Oak Bluffs and right across from the bike path. This five-bedroom house offers generously scaled living spaces throughout, including a large living room filled with natural light, an open stairway, a spacious dining room, and an updated kitchen. The first floor features a primary bedroom, a full bath with laundry, and a separate mudroom/back entry. Recent updates include a new kitchen with new appliances, new baths, fresh interior and exterior paint, new lighting, and new flooring and carpet throughout.

234 County Road, Oak Bluffs
4 Farm Way, Edgartown
$1,825,000
7 Beds ⋅ 4 Baths ⋅ 73580261 MLS
Two complete homes on one acre in Edgartown's Smith Hollow neighborhood — a rare find. Set at the end of a paved cul-de-sac, the property gives each house its own septic system, its own landscaped yard, and enough separation for real privacy.The main house has four bedrooms and two baths, along with a basement and a drive-under garage. The guest house features three bedrooms, two baths, a full basement, and laundry. With a solid rental history already in place, this is a chance to get two houses for the price of one.

4 Farm Way, Edgartown
148 Katama Rd, Edgartown
$4,100,000
4 Baths ⋅ 73575543 MLS
A rare mixed-use property on Katama Road, set right between downtown Edgartown and South Beach! Two residential apartments above — a 2BR and a 3BR, each with their own walk-up deck, in-unit laundry and dedicated parking. Both are occupied month-to-month under self-extending leases, giving a new owner flexibility. The first floor was home to an HVAC company for nearly a decade and is now vacant and ready for its next owner: roughly 1,253 sq. ft. of office with high efficiency heat pump heat & A/C, plus 1,148 sq. ft. of garage and storage. Ample on-site parking with 25 designated spaces and a loading dock for your business needs. Owned solar installed in 2018 conveys with the property, and the current owners have put significant capital improvements into the building since 2017 — electrical, roof, windows, integrated fire & security systems, mechanical systems, and irrigation system. This property has a long history of permitted commercial use well before these owners. The Edgartown Zoning Board of Appeals granted a special permit in 2016 for the operation of a small-scale business in a residential neighborhood, and that permit predates the current owners' purchase. A buyer will need approval from the Zoning Board to continue commercial operations.

148 Katama Rd, Edgartown
62 Schoolhouse Rd, Edgartown
$3,400,000
5 Beds ⋅ 5 Baths ⋅ 73577862 MLS
Ideally situated between South Beach and Edgartown Village, this newly renovated Katama compound offers exceptional flexibility for personal use and rental income.The four-bedroom contemporary main house features a newly constructed, expansive great room with a cathedral ceiling and an abundance of windows that fill the space with natural light. The open floor plan flows from the updated kitchen into a living room centered around a classic brick fireplace. Skylights bring in additional sunlight, while sliding doors open to expansive new south-facing decks—perfect for outdoor dining, entertaining, and relaxing after a day at the beach. The third floor provides a second living area, bedroom, and private half bath. A full basement offers ample storage and potential for additional finished living space. The detached two-car garage includes a private one-bedroom apartment above with its own wraparound deck. A bonus room with a half bath on the garage’s main level is ideal for an office. A custom-built cedar shed provides convenient storage for bicycles and beach gear. Set on a half-acre lot with easy access to the nearby bike path leading to Edgartown Village and South Beach, this turnkey property combines an outstanding location with a strong rental history. With multiple living spaces and excellent income-producing potential, this versatile Katama compound is a must-see. Photo's have been enhanced

62 Schoolhouse Rd, Edgartown
20 Hidden Cove, Oak Bluffs
$1,595,000
4 Beds ⋅ 3 Baths ⋅ 73577547 MLS
Set within the sought-after Hidden Cove community, a 65-acre private enclave with direct access to Sengekontacket Pond, this contemporary retreat offers an exceptional Martha’s Vineyard lifestyle. Residents enjoy a private community boat dock, scenic walking trails, pickleball and tennis courts, all just moments from Oak Bluffs and Edgartown.Set on a private, wooded lot, the home blends classic Vineyard character with relaxed coastal living. Cedar siding, an expansive wood deck, screened porch, and outdoor shower create inviting spaces for everything from quiet mornings to long summer evenings and post-beach afternoons.Inside, the home unfolds around a striking two-sided gas and wood-burning fireplace, with large windows bringing the surrounding landscape indoors. Four bedrooms offer comfortable space for family and guests, while a finished lower level adds exceptional versatility — currently configured as a media room and home office, with an unfinished portion ready to become a private gym, wine cellar, or whatever you envision.With water access, exceptional community amenities, and a private setting close to the Island’s favorite towns, Hidden Cove offers a rare combination of active outdoor living, privacy, and quintessential Vineyard ease.

20 Hidden Cove, Oak Bluffs
99 The Boulevard, Edgartown
$2,455,000
4 Beds ⋅ 5 Baths ⋅ 73577541 MLS
Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddle boarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with a strong rental history!

99 The Boulevard, Edgartown
14 High Meadow Ln, Oak Bluffs
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 73577549 MLS
Welcome to this sun-drenched, reverse contemporary-style home located in the lovely Meadow View Farms community! This multi-level home has boundless potential. The second level features a bright, open floor plan with cathedral ceilings, living, dining, and kitchen areas, and 3 sliding doors that take you outside to the upper deck. Open the sliders to the expansive deck and you will almost double the living space on the upper level. There is also a powder room on the upper level. The main floor features the primary suite with bath, walk-in closet, air conditioning, and sliders that open to the first-floor deck; that level offers 2 more spacious bedrooms and a shared bath. Venture downstairs to the above-grade lower level and enjoy the family room, reading nook, and bonus room. There is also a large storage/utility room with a second powder room. Like every true island home, there is an outdoor shower. Plenty of additional storage is under the deck. Solar panels were added in the fall of 2023. With 3 floors of living space and an expansive portion of the land behind it, this property offers so much potential for the next owners. Meadow View Farms Association is a neighborhood less than 2 miles from downtown Oak Bluffs featuring paved roads, tennis courts, and pastoral meadow views. Strong year-round rental history! The home is being sold "as is".

14 High Meadow Ln, Oak Bluffs
61 Canonicus Ave, Oak Bluffs
$2,200,000
3 Beds ⋅ 3 Baths ⋅ 73576858 MLS
Location, location, location: This 1999 home with all the comforts of the 21st Century is nestled on a landscaped lot within mellow surroundings. And yet … it’s located within mere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and a Land Bank trail. The situation hardly gets better. The 3BR/2.5BA house features a deep wraparound farmer’s porch, Brazilian cherry floors, an open and flexible layout, recent kitchen and bath updates, a generous 2nd floor bonus room and an attached single-car garage. The poured basement stands ready for your finishing whims. Kick back in your sunny backyard or on your shady porch with the distant peek of Nantucket Sound. Songbirds will serenade you from towering maples and oaks. Pinkletinks will chime in from Farm Pond. It’s no wonder that this abode has been loved – by vacation tenants as well as the owner. Note: This property lies within the jurisdiction of the Cottage City Historic District and Copeland District of the Town of Oak Bluffs. Passed Title 5.

61 Canonicus Ave, Oak Bluffs
no property photo
$1,755,000
3 Beds ⋅ 3 Baths ⋅ 22604610 MLS
Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living space plus 700+ square feet of newly finished recreation space above the two-car garage, with a private entrance and second-floor deck. The inviting first floor features a spacious kitchen with center island and abundant counter space, an adjacent dining room with wood stove, and glass doors opening to a wood deck and bluestone patio. Multiple sitting areas, a living room with gas fireplace, and private office provide flexible spaces for relaxing and working. Upstairs, two guest bedrooms share an updated bath, while the spacious primary suite features a walk-in closet and light-filled bath with soaking tub and tiled shower. Radiant-heated floors in the primary bedroom and bath add comfort. Additional amenities include a two-car garage and half basketball court. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this versatile home offers an ideal setting for relaxed island living and entertaining.

68 Front Street, Oak Bluffs
68 Front Street, Oak Bluffs
$1,755,000
3 Beds ⋅ 3 Baths ⋅ 73576389 MLS
Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living spaces, along with an additional 700+ square feet of newly finished recreation space above the two-car garage, complete with a private entrance and second-floor deck. The inviting first floor is designed for comfortable living and entertaining, featuring a spacious kitchen with a center island and abundant counter space. The adjacent dining room provides a warm gathering space with a wood stove, while glass doors open to a wood deck and bluestone patio for easy indoor-outdoor living. Multiple sitting areas, a living room with a gas fireplace, and a private office offer plenty of room to relax, gather, or work. Upstairs, two guest bedrooms share a recently updated bathroom, while the spacious primary suite features a walk-in closet and a large, light-filled bath with a soaking tub and tiled shower. Radiant-heated floors in the primary bedroom and bathroom provide an added level of comfort. Additional amenities include a two-car garage, versatile recreation space, second-floor deck, and half basketball court. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this home offers an ideal setting for enjoying all that Martha’s Vineyard has to offer.

68 Front Street, Oak Bluffs
no property photo
$850,000
22604582 MLS
Build Your Dream Home. Close to town and all that Oak Bluffs has to offer, Roger's Way is a small enclave offering a wonderful opportunity to create your own Vineyard retreat. A paved road leads to 15 Roger's Way, one of the last remaining lots in this desirable neighborhood. A three-bedroom septic system is already installed, and electric access is available at the edge of the property. Bring your vision and create your Vineyard dream home.

15 Roger's Way, Oak Bluffs
no property photo
$4,100,000
5 Beds ⋅ 4 Baths ⋅ 22604551 MLS
A rare mixed-use property on Katama Road, set right between downtown Edgartown and South Beach! Two residential apartments above — a 2BR and a 3BR, each with their own walk-up deck, in-unit laundry and dedicated parking. Both are occupied month-tomonth under self-extending leases, giving a new owner flexibility. The first floor was home to an HVAC company for nearly a decade and is now vacant and ready for its next owner: roughly 1,253 sq.ft. of office with high efficiency heat pump & A/C, plus 1,148 sq.ft. of garage and storage. Ample on-site parking with 25 designated spaces & a loading dock for your business needs. The current owners have put significant capital improvements into the building since 2017 — solar, electrical, roof,windows, integrated fire & security systems, mechanical & irrigation systems, and apt. renovations. This property has a long history of permitted commercial use well before these owners. The Edgartown Zoning Board of Appeals granted a special permit in 2016 for the operation of a small-scale business in a residential neighborhood, and that permit predates the current owners' purchase. A buyer will need approval from the town to continue commercial use. first-floor office 1,253 · garage and storage 1,148 · second floor 2,401 · deck 251. Floor plan dimensions are approximate. Buyer to verify all measurements, square footage, systems and permitted use. Commercial permit needs Edgartown approval.

148 Katama Road, Edgartown
125 Mayflower Ln, Tisbury
$2,295,000
4 Beds ⋅ 4 Baths ⋅ 73575143 MLS
Nestled on an acre of beautifully landscaped grounds in a tranquil, park-like setting, this home is tucked away on a quiet lane within an established neighborhood. Located just a quarter mile from miles of Land Bank walking trails and less than two miles from Main Street, it offers the perfect opportunity to embrace the Vineyard lifestyle, just minutes from the vibrant center of Vineyard Haven. Thoughtfully designed for both everyday living and entertaining, the main level boasts hardwood floors, high ceilings, and lots of windows that bathe the living areas and bedrooms in natural light. The kitchen serves as the heart of the home, featuring a center island and a dining area that opens onto a deck and attached gazebo—ideal for outdoor dining and gatherings. The inviting living room, complete with a propane fireplace, provides a warm and welcoming space. Three bedrooms—including a primary with ample closet space and a newly refinished bath are all located on the first floor. Additional highlights include new stainless-steel appliances, a Bertazzoni stove, Andersen windows, renovated baths, fresh paint, refinished floors, custom window treatments, plantation shutters, and a generator. This turnkey property is ready for immediate occupancy, allowing you to settle in and enjoy from day one. On the garden level, you'll find versatile space for additional living, relaxation, or exercise. The family room includes a half-bath and sliders that open to the patio and outdoor shower. A separate guest suite complete with bedroom, den, full bath, and kitchenette provides flexible accommodations for visitors. Meticulously maintained inside and out, this home is ready to welcome its next owner.

125 Mayflower Ln, Tisbury
43 N Slope Lane, Chilmark
$1,649,900
3 Beds ⋅ 2 Baths ⋅ 73573563 MLS
Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring comfortable living spaces ideal for year-round living or seasonal enjoyment. With 3 bedrooms and 2 full baths, the layout offers flexibility for family, guests, or a home office. Custom soapstone countertops add to this home's beauty. Expansive outdoor space invites relaxation, exploration, and the potential for future enhancements, all within a serene woodland environment. An increasingly rare opportunity to own a conservation-abutting property on Martha’s Vineyard—perfect as a primary residence, vacation home, or long-term investment in one of the island's most desireable natural settings.

43 N Slope Lane, Chilmark
no property photo
$1,649,000
3 Beds ⋅ 2 Baths ⋅ 22604496 MLS
Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring comfortable living spaces ideal for year-round living or seasonal enjoyment. With 3 bedrooms and 2 full baths, the layout offers flexibility for family, guests, or a home office. Custom soapstone countertops add to this home's beauty. Expansive outdoor space invites relaxation, exploration, and the potential for future enhancements, all within a serene woodland environment. An increasingly rare opportunity to own a conservation-abutting property on Martha's Vineyard—perfect as a primary residence, vacation home, or long-term investment in one of the island's most desirable natural settings.

43 N Slope Lane, Chilmark
3 Oak Bluffs Avenue, Oak Bluffs
$5,000,000
2 Baths ⋅ 73572959 MLS
Location, Location, Location! A once-in-a-lifetime legacy investment opportunity in one of the most desirable and high-visibility locations on Martha’s Vineyard. Priced to sell and positioned for success, 3 Oak Bluffs Ave is prominently situated at the corner of Seaview Ave and Oak Bluffs Ave—you know the spot. This exceptional property places your business directly in the center of it all, with unmatched exposure to both pedestrian and vehicular traffic. Located directly across from Inkwell Beach, Ocean Park, The Steamship Authority and SeaStreak ferry terminals, and Circuit Ave, and just around the corner from Oak Bluffs Harbor, this is a location that simply speaks for itself. And there’s more: the entire on-site parking lot belongs to this property, providing plenty of dedicated parking, with additional parking options available throughout the surrounding area. In a location where parking can be at a premium, this is a significant advantage. Whether you’re looking to relocate an existing business, expand your footprint, or launch your next venture, it’s hard to imagine a better location to bring your vision to life. Put your business at the gateway to Martha’s Vineyard, take advantage of extraordinary visibility and traffic, and position yourself for long-term success. B1 Zoning allows for a variety of commercial uses, offering flexibility for a range of business opportunities. Opportunities of this caliber—and in a location this prominent—rarely come along. This one won’t last. Secure this incredible property and invest in a location that could become the foundation of your next great success.

3 Oak Bluffs Avenue, Oak Bluffs
267 Barnes Road, Oak Bluffs
$4,395,000
3 Beds ⋅ 6 Baths ⋅ 73572956 MLS
Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a fresh, contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres, the 4,046-square-foot home balances privacy with comfortable spaces for entertaining or relaxing. Oversized windows bring Lagoon views into nearly every room. The main level features soaring ceilings, a wood-burning fireplace, wet bar, and an eat-in kitchen opening to a sunny patio. A separate two-room wing with full bath and private deck offers flexible space for an office, den, studio, or guest accommodations. Upstairs, the primary suite includes a fireplace, walk-in closets, ensuite bath, and Lagoon-facing deck. Two additional ensuite bedrooms open to a wraparound deck and 3-season porch. The refinished 2,000-square-foot walk-out lower level includes a full bath, laundry, and space for a gym, media room, or additional living area. Offered fully furnished, this waterfront retreat is ready to enjoy. Whether you are hosting a full house or savoring a quiet weekend, the Lagoon becomes your backdrop: sunrise coffees, afternoon swims, and sunset gatherings right at the water’s edge.

267 Barnes Road, Oak Bluffs
no property photo
$2,650,000
3 Beds ⋅ 3 Baths ⋅ 22604449 MLS
Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equally suited to quiet Island weekends, a house full of summer guests or comfortable year-round living. At the heart of the home is a beautifully remodeled kitchen, completed in 2023 and designed to be part of daily life rather than separate from it. From here, the home unfolds into a spacious living room warmed by a propane fireplace, a formal dining room and a separate sitting room—giving family and guests the increasingly rare luxury of having both places to come together and places to retreat. Three large bedrooms provide comfortable private quarters, while an open loft creates another flexible destination for working, reading, watching a movie or simply escaping the activity downstairs. Below, a substantial unfinished basement with high ceilings and both interior and exterior access provides exceptional storage and flexibility for the future. Summer living extends naturally outdoors. A generous back deck overlooks the wooded acre-plus setting, offering a private place for morning coffee, long dinners and evenings under the Vineyard sky. And after a day spent at the beach, there is perhaps no more quintessentially Island pleasure than coming home to an outdoor shower. Beyond the property, Woodhaven offers something increasingly difficult to find: a neighborhood setting surrounded by nature with access to trails connecting the Manuel F. Correllus State Forest - opening miles of the Island for walking, running and biking. Private without being isolated, spacious without feeling overwhelming, and thoughtfully updated where it matters most, 10 Woodhaven Drive offers a relaxed approach to Edgartown living—and a home designed to be enjoyed well beyond the summer season.

10 Woodhaven Drive, Edgartown
90 Manaquayak Road, West Tisbury
$7,330,000
73572001 MLS
Lambert’s Cove Inn & Resort is an upscale hospitality asset in West Tisbury, Martha's Vineyard, operating as a 15-room boutique hotel spread across a historic farmhouse, restored stable, and barn. The property generates three distinct revenue streams through its luxury lodging, the high-end restaurant (seating up to 70–80 guests), and its status as a premier wedding venue featuring an English Garden and Great Lawn. The 8- acre estate is being offered for sale with a brand-new 5-year triple-net (NNN) lease yielding $55,000 per month at a 9% Cap Rate, providing a stable passive income opportunity for an investor while the operator manages the day-to-day hospitality and event services. Lamberts Cove represents a rare opportunity to acquire a scaled, income-producing boutique hospitality asset in one of the most supply-constrained resort markets in the United States. Established in 1790 and comprehensively renovated in 2022, the property combines irreplaceable historical character with modern operating infrastructure. The combination of limited competitive supply, meaningful land scale, and enduring destination demand positions Lambert’s Cove Inn as a defensible hospitality investment with stable operating fundamentals and long-term value preservation.

90 Manaquayak Road, West Tisbury
no property photo
$4,100,000
22604423 MLS
A rare mixed-use property on Katama Road, set right between downtown Edgartown and South Beach! Two residential apartments above — a 2BR and a 3BR, each with their own walk-up deck, in-unit laundry and dedicated parking. Both are occupied month-tomonth under self-extending leases, giving a new owner flexibility. The first floor was home to an HVAC company for nearly a decade and is now vacant and ready for its next owner: roughly 1,253 sq.ft. of office with high efficiency heat pump & A/C, plus 1,148 sq.ft. of garage and storage. Ample on-site parking with 25 designated spaces & a loading dock for your business needs. The current owners have put significant capital improvements into the building since 2017 — owned solar, electrical, roof, integrated fire & security systems, mechanical & irrigation systems, and apt. renovations. This property has a long history of permitted commercial use well before these owners. The Edgartown Zoning Board of Appeals granted a special permit in 2016 for the operation of a small-scale business in a residential neighborhood, and that permit predates the current owners' purchase. A buyer will need approval from the town to continue commercial use.

148 Katama Road, Edgartown
Old Country Lane, Tisbury
$450,000
73571746 MLS
Discover peace and privacy without sacrificing location. Nestled under a serene natural tree canopy, this central wooded parcel provides a quiet setting just minutes from local shops, dining, and beautiful beaches. Ready for your custom vision.

Old Country Lane, Tisbury

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.