Refine Search
Sort by
$3,650,000
5 Beds 3 Baths 73542542 MLS
A rare opportunity to create a premier in-town compound in one of Edgartown’s most desirable locations. Set on High Street, just moments from downtown Edgartown, this exceptional 16,000+ square foot lot offers tremendous potential to create a substantial five-bedroom residence while enjoying the convenience and charm of village living. The property currently features a 4 bedroom main house, attached 1 bedroom apartment, and an oversized garage with an attached 556-square-foot barn. The property provides a unique foundation for expansion, renovation, or a thoughtfully designed new build. With its generous lot size and coveted location, 49 High Street presents a rare opportunity to create a legacy property within walking distance of Edgartown’s shops, restaurants, harbor, and village amenities.

49 High Street, Edgartown

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

$3,600,000
4 Beds 3 Baths 73494388 MLS
Set in the heart of Edgartown Village, this pristine Cape offers a wonderful blend of charm, comfort, and in-town convenience. Just moments from boutique shopping, galleries, dining, and the harbor, this four-bedroom, three-bath home captures the quintessential Vineyard lifestyle. A formal front entry opens to the inviting living room, while a side entrance leads to the bright kitchen with a built-in banquette dining area. The private primary wing features its own entrance, cathedral-ceiling bedroom, sitting area, full bath, kitchenette, and French doors opening to a pergola patio. The first floor also includes a guest bedroom, full bath, and laundry. Upstairs offers a large primary bedroom, another bedroom, and a full bath. The landscaped backyard features two patios for outdoor dining and entertaining. A full basement, storage shed, and one-car garage with additional parking complete this exceptional in-town offering near Sheriff’s Meadow trails and Fuller Street Beach.

13 Plantingfield Way, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$1,100,000
3 Beds 2 Baths 73534315 MLS
Easy Edgartown living awaits in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout that works beautifully for everyday life, entertaining, or relaxed seasonal stays. The private primary suite includes its own bath, while two additional bedrooms share a full bathroom, creating a practical and comfortable floor plan. A full basement provides excellent storage and added flexibility, with room for bikes, beach gear, tools, or future possibilities. Step outside to enjoy the deck, fenced yard, and quintessential outdoor shower — the perfect Vineyard touch after a day at the beach. With the bus stop conveniently located at the end of the street, getting around the island is simple and stress-free. Just minutes from downtown Edgartown, bike paths, restaurants, shops, and some of the island’s most loved bea

34 Tenth St S, Edgartown

Listing courtesy of Listing Agent: Chrissie Teague from Listing Office: Insight Realty Group, Inc..

$2,595,000
4 Beds 4 Baths 73504062 MLS
COASTAL-STYLE CONTEMPORARY. Ideally located in central Edgartown, the property offers convenient access to the bicycle path, Morning Glory Farm, Edgartown Village and Katama/South Beach by way of Meetinghouse Way. This attractive home has been tastefully renovated and is a perfect island retreat for year-round and summer living. The open layout features vaulted ceilings, gorgeous hardwood floors and three walls of glass windows. French doors that open onto a three-season porch and an expansive wraparound mahogany deck, perfect for indoor-outdoor living and entertaining. The living area is anchored by a lovely gas fireplace and a beautiful kitchen which features stainless appliances, custom tile, countertops, wine cooler/beverage center and a center prep island/breakfast bar with counter seating. Mini split dual AC/heat units are located in every room and also in the basement. This property can be enjoyed as-is or expanded for up to seven bedrooms. Sale is subject to court approval.

471 West Tisbury Road, Edgartown

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.

$2,210,000
3 Beds 3 Baths 73527361 MLS
Private Edgartown Retreat With Timeless Cottage Charm - Tucked away in a quiet and serene setting on the edge of Edgartown Village, this charming Vineyard retreat is ideally positioned halfway between town and State Beach, with the bicycle path nearby for easy access to both. Set along a private lane and bordered by classic Vineyard stonewalls, the property offers a rare sense of privacy with an expansive backyard and a wooded buffer between the property and the Edgartown Golf Club. Full of authentic island character, the home is loaded with charming cottage details and designed for effortless indoor-outdoor living. French doors open to an expansive south-facing deck and stone terrace with a pergola, creating an inviting setting for relaxing, dining, and entertaining. A screened-in porch, vegetable gardens, and ample room to add a pool further enhance the property’s easy Vineyard lifestyle. Inside, timeless charm blends with modern comfort, featuring two fireplaces and bright spaces.

17 Oakdale Dr, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$2,600,000
4 Beds 3 Baths 73525812 MLS
Tucked away on a private 1.5-acre parcel in Katama, this thoughtfully designed 4BR/2.5BA home offers the layout, amenities, and lifestyle buyers seek most in this coveted location. The open main living area features high ceilings, a fireplace, and French doors leading to a spacious deck overlooking the expansive yard with room for a pool. A screened porch adds to the effortless indoor/outdoor Vineyard living experience. The first floor includes a true primary suite, while upstairs offers three additional bedrooms, including a second potential suite with an ensuite bath already rough-plumbed. A full basement provides excellent storage and future expansion potential for media, recreation, or fitness space. Additional highlights include central air, generous storage, and a quiet setting near the bike path with easy access to South Beach and Edgartown Village. Privacy, acreage, convenience, and room to create the ultimate Vineyard retreat.

2 Cosmos Way, Edgartown

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.

$4,700,000
4 Beds 4 Baths 73523238 MLS
Set the tone the moment you arrive with a dramatic first-floor foyer showcasing post-and-beam construction and warm architectural character. The heart of the home is an expansive great room anchored by a gas fireplace, seamlessly flowing through French doors that open to a sun-drenched pool area—perfect for indoor-outdoor living and entertaining. A generous dining area connects effortlessly to a well-appointed kitchen, highlighting double wall ovens, ample storage, built in beverage center and island seating for informal dining. The first floor also offers a versatile office or family room. The spacious primary bedroom is a true retreat with vaulted ceilings, featuring an ensuite bath with oversized shower with ample counter space including a seated vanity. Double closets plus a walk-in closet, and a wall to wall window seat with views overlooking the pool. Step outside to wraparound decks that extend the living space and invite you to unwind in a private, resort-like setting.

27 Knoll Drive, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..

$1,700,000
5 Beds 3 Baths 73509658 MLS
Pristine and superbly maintained, this three-bedroom home and two-bedroom guest house has tremendous upside potential and a substantial rental history. This property is tied to town sewer and will allow for up to 7 bedrooms. One additional bedroom in the main house is possible within the existing footprint with appropriate town approvals. There is an additional 668 sq. ft. of finished space in the lower level that is not included in the ELA above. Potential buyers should consult with the town Building Department. This property has been freshly landscaped with extensive plantings and an irrigation system. The list of improvements is long, and the result is a stylishly updated property inside and out. It is conveniently located halfway between Morning Glory Farm and Meetinghouse Road, a primary access road to South Beach, 3.8 miles distant and only 8 minutes by car. Adjacent to the bike path, it is 2 miles to Main Street in Edgartown. It is being offered fully furnished.

4 Hye Ln, Edgartown

Listing courtesy of Listing Agent: Buder Team from Listing Office: Sandpiper Realty, Inc..

$3,400,000
4 Beds 3 Baths 73460777 MLS
Post-and-beam style Edgartown home in a quiet, established neighborhood just minutes from downtown. This year-round property offers functional living spaces, a thoughtful layout, and generous outdoor areas ideal for relaxing or entertaining. The property is currently configured as a three-bedroom, 1-1/2 bathroom main house with a 1BR/1BA accessory apartment over a one-car, detached garage on a 1/2 acre lot. The garage structure also boasts a finished first floor studio space. The large, level lot also presents an excellent opportunity for those looking to start new and create a custom island retreat or private oasis complete with a pool. This property can be connected to town sewer and support up to six bedrooms with a grandfathered guest house. Located close to shops, restaurants, beaches, and the harbor, the home provides a perfect blend of convenience and privacy — ideal for year-round living, vacation use, or rental potential in one of Edgartown’s most sought-after areas.

44 Plantingfield Way, Edgartown

Listing courtesy of Listing Agent: David Dickinson from Listing Office: Compass.

$3,250,000
4 Beds 4 Baths 73484296 MLS
This updated classic cottage is located in the heart of Edgartown Village, less than a quarter mile from Main Street. Upon arrival, you are welcomed by a spacious front porch and elegant French door entry that lead into a dramatic foyer. The light-filled open floor plan seamlessly connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. The first floor opens to a charming brick terrace and fenced backyard, an ideal setting for outdoor gatherings.The swimming pool serves as the centerpiece of this private outdoor retreat. This delightful cottage features four bedrooms, each with its own full bath, including a convenient first-floor primary bedroom suite. An elegant staircase leads upstairs to two spacious bedrooms with private baths. A charming balcony separates the bedrooms and is lined with a wall of ample storage closets, blending style with exceptional functionality.The partially finished lower level adds over 500 s.f.

99 Cooke St, Edgartown

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.

$3,381,000
4 Beds 4 Baths 73501677 MLS
This distinguished home in Edgartown’s Bold Meadow neighborhood features light-filled interiors highlighted by south-facing windows in a cathedral-ceilinged Great Room that flows into a new sunroom. The main house offers 3 bedrooms, complemented by a spacious detached 900-sf guest apartment above an oversized garage, ideal for hosting. Recent upgrades include a renovated kitchen, updated primary bath, and thoughtfully integrated sunroom. Set on 1.5 acres with greenbelt on three sides, the property offers privacy, expansion potential, and room for a future pool. A full-height basement provides additional possibilities such as a media room or gym. Located less than 3 miles to Edgartown Village and close to Morning Glory Farm, the home also benefits from 30 SunPower solar panels for energy efficiency. Move-in ready and meticulously maintained

25 Bold Meadow Road, Edgartown

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.

$1,150,000
3 Beds 2 Baths 73489567 MLS
Welcome to this light-filled Vineyard Cape brimming with potential, offering an open layout and abundant natural light. Vaulted ceilings enhance the spacious living and dining area, creating an airy setting for relaxing or entertaining. The kitchen flows seamlessly to an outdoor deck, ideal for summer gatherings and al fresco dining. Two bedrooms and a full bathroom with laundry complete the first floor. Upstairs, you’ll find a generous primary bedroom with abundant closet space, an additional full bathroom, and a cozy loft-style den overlooking the main living area. Centrally located just moments from the bike path, with easy access to Edgartown, nearby beaches, and all down-Island amenities, this property presents a wonderful opportunity to make it your own. With a 4-bedroom septic in place there is potential room for expansion. The property is being sold “AS IS”.

18 Windsor Drive, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$1,125,000
3 Beds 2 Baths 73489622 MLS
Nestled on a wooded lot only 3.5 miles from Edgartown Village, this three-bedroom home offers a bright, open-plan main level with kitchen, dining, and living area flowing onto a private deck—ideal for outdoor dining, morning coffee, or enjoying the outdoors. A first-floor bedroom and bath add convenience, while two upstairs bedrooms and a bath provide flexible space for families or guests. The full basement offers generous storage and in-home laundry. BOH says four bedrooms are possible if septic is upgraded. Current three bedroom septic passed Title V. Easy access to multiple towns and Island beaches, this home puts the best of Martha's Vineyard at your doorstep.

52 Windsor Drive, Edgartown

Listing courtesy of Listing Agent: Emma Kennedy from Listing Office: Sandpiper Realty, Inc..

$2,325,000
3 Beds 4 Baths 73494390 MLS
Katama ~ Easy Island Living in Edgartown Estates. Tucked away on a quiet paved road, this inviting home offers the best of Vineyard living, just minutes to South Beach, downtown Edgartown, and the bike path. Bright and comfortable, the interior features a vaulted living room with gas fireplace and an open kitchen/dining area that flows to a spacious back deck—perfect for outdoor dining and summer entertaining. An outdoor shower completes the beach-day routine. The first-floor primary suite includes cathedral ceilings, a walk-in closet, and private bath, while two second-floor bedrooms share a full bath. A bonus space with half bath above the garage is ideal for guests or a home office. Additional highlights include a mudroom/laundry area, oversized two-car garage, and full unfinished basement. Offered fully furnished and ready to enjoy.

42 Deacon Vincent Way, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$1,900,000
5 Beds 3 Baths 73472940 MLS
Tucked away behind association common land, this year-round compound offers the perfect blend of privacy, space, and flexibility. The post-and-beam main house features four bedrooms and combines timeless character with functional design, ideal for everyday living or seasonal enjoyment. A separate one-bedroom guest house with a welcoming farmer's porch is thoughtfully sited to ensure privacy and independence, complete with its own driveway and parking. The detached garage, with a loft above, adds even more versatility—ideal for storage or future finished space. Situated on one of the largest parcels in the Smith Hollow Association, the property enjoys a tranquil, park-like setting. With direct access to the bike path at the end of the road, you're just minutes from Edgartown and all down-island amenities. More than just a house—this is a place to call home.

36 Smith Hollow Dr, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

$1,850,000
4 Beds 4 Baths 73357842 MLS
Welcome to Dark Woods – A Quiet Retreat, moments from the Village, bike paths, pristine beaches, and 27 acres of Sheriff’s Meadow conservation land. This meticulously maintained property is being offered fully furnished and is ready for your immediate enjoyment. The home offers an expansive layout that blends indoor and outdoor living. Step inside to find a spacious living room with a gas fireplace, a dining room, and an open eat-in kitchen overlooking a private backyard. The kitchen flows seamlessly outdoors to a two-tiered deck featuring a hot tub and outdoor shower. Above the two-car garage, a versatile bonus room offers the perfect space for a home office, media room, or private retreat. The primary ensuite enjoys a newly renovated bathroom. Two generously sized guest bedrooms and a full bathroom complete this level. The finished walk-out lower level includes an ensuite bedroom with a comfortable living and dining area. Tied to town water and sewer, you can expand up to 7 bedrooms.

43 C Dark Woods Rd, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$1,175,000
3 Beds 2 Baths 73439891 MLS
Nestled on a lush and private parcel close to The Boulevard, this contemporary three-bedroom, two-bath residence offers the perfect blend of style and comfortable living. Highlights include a gas fireplace, wood floors, an expansive deck to relax on, and established gardens. There’s even a shed to store all your summer gear. Enjoy this oasis as is or use as a foundation for future expansion.Explore the nearby walking trails of Felix Neck Wildlife Sanctuary. For those that love the water, the town landing is less than a mile away. Kayaking, paddleboarding and shell fishing await.Perfect as a year-round residence, summer retreat, or rental (with established history) this versatile home is being sold furnished (with a few exclusions) allowing for a smooth transition for the new owners- just bring your toothbrush.

112 Third Street North, Edgartown

Listing courtesy of Listing Agent: Kristin Buck from Listing Office: Donnelly + Co..

$1,775,000
3 Beds 2 Baths 73485519 MLS
A few blocks to historic Edgartown Village from this updated beach house in desirable Edgartown Estates. The open living area features decorative wood beams, a wood stove, designer tile flooring, and sliding doors to an expansive wraparound Trex deck (2018), creating seamless indoor-outdoor living. The expanded kitchen (2018) includes granite countertops, stainless steel appliances, ample storage, and natural light. Three bedrooms include a private primary suite with renovated en-suite bath, and comfortable guest accommodations. The finished lower-level bonus room with floating Pergo flooring is ideal for recreation or secure owner storage. Outdoor amenities include a classic Vineyard outdoor shower, storage shed, Belgian Block driveway accents, and mature landscaping. A four-bedroom septic system allows for future expansion. Offered turnkey, ideal for year-round enjoyment or strong seasonal rental income, all convenient to Edgartown Village, bike paths, and South Beach.

90 Schoolhouse Road, Edgartown

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..

$1,510,000
4 Beds 3 Baths 73445262 MLS
Edgartown Village Opportunity – Main House & New Guest Cottage Tucked just off Upper Main Street, this unique Edgartown property offers exceptional flexibility with two dwellings—perfect for personal use, rental income, or a combination of both. The main house has been thoughtfully updated with numerous improvements, including a new kitchen, renovated bath, upgraded electrical, and HVAC system for year-round comfort. The guest house, newly built in 2025, provides a fresh, turnkey space ideal for guests or rental potential. With a total of four bedrooms between both structures—and the ability to expand to six bedrooms thanks to town water and sewer connection—this property presents a rare opportunity in a sought-after location. Just moments from shops, restaurants, and all that Edgartown has to offer, this versatile property combines convenience, investment potential, and island charm.

10 Dory Circle, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..

$2,475,000
4 Beds 4 Baths 73391522 MLS
Nestled on a generous corner lot in one of Edgartown’s sought-after neighborhoods, this beautifully maintained 4BD, 3.5BA home offers the perfect blend of comfort, convenience, and classic Vineyard charm. The home features a spacious and versatile floor plan, ideal for both year-round living and summer getaways. The light-filled living areas, anchored by a floor to ceiling wood burning fireplace, flow seamlessly into a well-appointed kitchen and dining area, perfect for entertaining. Step into the inviting screen porch-an ideal spot to enjoy your morning coffee or unwind with evening breezes. A partially finished basement and two-car garage provides ample storage, while the association tennis courts offer recreational opportunities just steps from your door. Outside, the expansive yard provides plenty of room for future expansion of a pool or ADU as the lot will support 6-bedrooms. With its prime location, community amenities, and room to grow, this property is a fantastic opportunity.

28 Martha's Road, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..

$2,470,000
4 Beds 4 Baths 73464407 MLS
CHARMING VINTAGE HOME IN THE HEART OF EDGARTOWN VILLAGE. Nestled within lush perennial gardens and surrounded by hedges and a classic picket fence, the Charles W. Crowell House is a delightful antique home that captures the essence of a bygone era. With its origins dating back to 1760, the home boasts beams crafted from trees that once grew on the property. These timeless timbers are prominently showcased throughout the home, adorning the ceilings and walls with their enduring presence. Renovated in 2010 to incorporate modern conveniences such as updated electrical, central air conditioning and refreshed kitchen and baths, the residence has seamlessly blended contemporary comfort with its original period charm. Noteworthy features include an open staircase, wide-planked pine flooring, two original fireplaces, and exquisite period millwork, as well as built-in cabinets and bookshelves. Comprising a total of four bedrooms and three and one-half baths, including a first-floor Primary Bedr

2 Green Ave, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$2,340,000
4 Beds 5 Baths 73433414 MLS
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.

8 Old Dunhams Corner Way, Edgartown

Listing courtesy of Listing Agent: Kristin Buck from Listing Office: Donnelly + Co..

$2,590,000
4 Beds 3 Baths 73432815 MLS
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. 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. The primary bedroom offers private access to the pool terrace. 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. Step outside to your private backyard oasis, where a heated 8x19 saltwater pool is framed by a stone terrace.

2 Orchard Ln, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$3,120,000
4 Beds 4 Baths 73351506 MLS
Water views with a pool! This chic contemporary 4-bedroom home with a pool and 2-car garage enjoys the ever-changing water views of Sengekontacket Pond and Nantucket Sound on three levels. Fully renovated, this delightful home, being sold turnkey, marries a timeless Vineyard vibe with modern luxury. The mudroom entryway opens to the kitchen with a breakfast island, dining room, and living room with a gas fireplace and sliders to the heated pool. The fabulous family room is off the dining room, and beyond the kitchen is an office with sliders to the deck. A pantry, half bath, and laundry complete the first floor. There are 4 bedrooms on the second floor, including 2 primary suites with views, all with vaulted shiplap ceilings, a den, and a shared bath. The den and one of the suites both have private decks that capture the essence of the views. An outstanding spiral staircase provides access to the fabulous “Lookout Lounge,” with stunning views.

110 Fifth Street North, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

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.