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$2,395,000
4 Beds ⋅ 3 Baths ⋅ 73567153 MLS
Renovated Edgartown Retreat With Pool, Terrace + Outdoor Entertaining Pavilions - Designed for relaxed indoor-outdoor living, this recently renovated four-bedroom, three-bath Edgartown home is set on just under an acre and centered around an exceptional new backyard retreat. From quiet mornings by the pool to leisurely dinners beneath the pergolas, the property offers a welcoming setting for enjoying the Vineyard lifestyle. The pool features a sun shelf and built-in seating and is surrounded by an expansive stone terrace with generous room for lounging and entertaining. Two pergola pavilions create a stylish open-air living area with dedicated lounge and dining spaces, while an outdoor shower completes the resort-like setting. An expanded rear deck provides an easy connection between the home and its impressive outdoor amenities. Inside, thoughtful renovations have created bright, comfortable spaces for everyday living and gathering. The redesigned kitchen features crisp white cabinetry, marble countertops, stainless-steel appliances, and an extended marble breakfast bar that connects the kitchen and dining areas while providing additional seating and workspace. Hardwood floors run throughout both levels, and air conditioning has been added for year-round comfort. The first floor also includes a renovated full bath and a new laundry room with front-loading appliances. Upstairs, a newly created primary suite offers privacy and a beautifully finished bath with a large custom-tiled shower. Two additional bedrooms feature new hardwood floors and fresh paint and share a completely renovated full bath. Further improvements include a new front stoop, Bluetooth-controlled irrigation, and a two-car garage with its own rear deck and outdoor shower, adding convenience for island living. Connected to town sewer with capacity for seven bedrooms, the property presents valuable future expansion possibilities. An established rental income history offers additional flexibility for buyers interested in combining personal enjoyment with income-producing potential. With its renovated interiors, exceptional pool setting, multiple outdoor gathering spaces, and room to envision what comes next, this distinctive Edgartown retreat is ready for memorable days and evenings on Martha's Vineyard.

105 Whalers Walk, Edgartown

Listing courtesy of Listing Agent: Ekaterina Brush from Listing Office: Compass.
$1,395,000
3 Beds ⋅ 2 Baths ⋅ 73549401 MLS
Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential vacation rental, the home features an open living and dining area, efficient kitchen and welcoming living room with wood-burning fireplace. Outdoor living includes a sunny south-facing front deck, newer rear deck for grilling and dining, and a second-floor balcony perfect for morning coffee. Natural landscaping keeps upkeep simple, while a detached Party/Game Shed with French doors opens to the backyard and firepit area, offering flexible bonus space for entertaining, remote work or relaxing after a day at the beach or in town.

44 Prices Way, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$3,495,000
2 Beds ⋅ 2 Baths ⋅ 73545630 MLS
Set on an exceptional .65 -acre parcel, this rare offering combines privacy, space, and an unbeatable location just moments from town and the water. The expansive lot offers a unique opportunity to expand and create a custom estate tailored to your vision. Surrounded by mature landscaping and generous outdoor space, the property offers a peaceful retreat while remaining conveniently close to shops, dining, beaches, and waterfront activities. Whether you're seeking a year-round residence, a seasonal escape, or an investment with long-term upside, this property presents endless possibilities in one of the area's most desirable settings.

48 Plantingfield Way, Edgartown

Listing courtesy of Listing Agent: Julia Smith from Listing Office: Donnelly + Co..
$2,495,000
1 Beds ⋅ 2 Baths ⋅ 73540958 MLS
Located on Upper Main Street in Edgartown’s BII zoning district, this versatile property is currently home to Lucky Hank’s restaurant. Set on a desirable lot with a large private parking area, and in a coveted high-visibility location. The building offers a turnkey restaurant space and thriving business complete with a fully equipped commercial kitchen on the first floor. Upstairs, you’ll find one bedroom with an ensuite full bathroom, currently being used as the office. There is also an additional room being used for restaurant storage. With the flexibility to convert the property back to residential use, if desired, this is a rare opportunity in a prime location that should not be overlooked! This offering is for the real estate and the business. Please inquire with listing agent for additional details and information.

218 Upper Main Street, Edgartown

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.
$21,500,000
10 Beds ⋅ 14 Baths ⋅ 73517157 MLS
A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha’s Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant entertaining and everyday living. The main residence showcases oak floors, nickel board walls, premium appliances, and seamless indoor-outdoor flow with a screened patio. The chef’s kitchen includes dual dishwashers, a Miele coffee bar, and wine storage, while a custom bar can convert to a secondary kitchen. Highlights include multiple living areas, en-suite bedrooms, a luxurious primary suite, bunk room, and a finished lower level with media room and wine cellar. Outdoors, a pool, spa, cabana, and carriage house create a private coastal retreat.

56 North Summer Street, Edgartown

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
$2,225,000
3 Beds ⋅ 3 Baths ⋅ 73493917 MLS
Experience the ease of summer living in your own Martha’s Vineyard beach house. Perched atop a rise with sweeping views, abundant natural light, and star-filled skies, this furnished, move-in-ready home with four levels of lifestyle. A dramatic 30-foot vaulted foyer leads to a fully renovated chef’s kitchen with Sub-Zero refrigeration, premium stainless appliances, stone counters, and a custom banquette seating 10. The home features a formal dining room, oak floors, a wood-burning stone fireplace featured in Architectural Digest, and a view-facing living room with balcony. The primary suite includes a walk-in closet and en-suite bath with soaking tub and double vanity, plus two additional bedrooms. A spiral staircase leads to a loft lounge with private balcony and two bonus rooms. The walk-out lower level adds flexible space for a gym, office, or lounge. Expansion potential allows up to seven bedrooms, plus guest house, pool, and pool house. $25,000 credit at closing for sewer tie-in.

81 Whalers Walk, Edgartown

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..
$1,395,000
3 Beds ⋅ 1 Baths ⋅ 73490019 MLS
Opportunity Knocks - Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat, while building value in a sought-after location. A fantastic opportunity to customize, restore, and make it your own. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

17 Chapman La, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$9,000,000
4 Beds ⋅ 7 Baths ⋅ 73476388 MLS
Behind its classic Village façade lies a home that reimagines Edgartown living, where timeless architecture meets bright, light-filled interiors and an effortless sense of modern luxury. Just moments from Main Street and the harbor, it offers the rare opportunity to enjoy the best of the Village from a residence designed for the way people live and entertain today. Exceptional craftsmanship and thoughtfully curated finishes define every level of the home. The backyard is a true extension of the home, anchored by a fully equipped cabana, heated saltwater pool, sunken fire pit, and striking custom glass wall. A strong rental history further enhances the property's appeal, offering exceptional flexibility as a private family retreat or a compelling investment opportunity. A home where exceptional quality meets effortless living, offering a fresh and relaxed interpretation of luxury in the heart of Edgartown Village.

43 Peases Point Way S, Edgartown

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

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