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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.
$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

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.
$2,700,000
3 Beds ⋅ 3 Baths ⋅ 73553701 MLS
Privately nestled amid sweeping gardens and lush natural landscaping, this 3-bedroom, 3-bath home offers the perfect blend of timeless design and refined contemporary living. Thoughtfully curated interiors feature an open-concept living area, a large kitchen with Viking cooktop, Fisher & Paykel dishwasher and quartz countertops, inviting dining spaces, and comfortable gathering rooms filled with natural light. French doors open to a brick patio with fireplace, surrounded by mature gardens, creating seamless indoor-outdoor living ideal for entertaining or quiet relaxation. With beautifully designed indoor and outdoor spaces in the heart of Katama, this property is a true Vineyard sanctuary.

205 Meetinghouse Way, Edgartown

Listing courtesy of Listing Agent: Thayer Whipple from Listing Office: Sandpiper Realty, Inc..
$2,875,000
3 Beds ⋅ 3 Baths ⋅ 73553681 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 96 at 131 N. Water Street is a beautifully appointed 1061± sq. ft., second and third-floor condominium featuring 3 beds and 3 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cooktop, microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits,.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 96 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

131 North Water St-Huxford Cottage Unit 96, Edgartown

Listing courtesy of Listing Agent: Michele Lawlor from Listing Office: Corcoran Property Advisors.
$2,595,000
2 Beds ⋅ 2 Baths ⋅ 73553678 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. An in-unit washer/dryer, outdoor shower, and elevator access add everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. A rare opportunity to own a luxury residence at one of Martha’s Vineyard’s most celebrated destinations.

131 North Water St-Collins Cottage Unit 22, Edgartown

Listing courtesy of Listing Agent: Michele Lawlor from Listing Office: Corcoran Property Advisors.
$2,425,000
2 Beds ⋅ 2 Baths ⋅ 73553676 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cook-top stove, microwave, and refrigerator/freezer. An outdoor shower adds to everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind.

131 North Water St -Rowley Cottage Unit 62, Edgartown

Listing courtesy of Listing Agent: Michele Lawlor from Listing Office: Corcoran Property Advisors.
$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.
$2,590,000
4 Beds ⋅ 8 Baths ⋅ 73523165 MLS
Located on a quiet street just minutes from Edgartown Village, this versatile compound offers privacy, flexibility, and close proximity to the Island’s best outdoor amenities. Set on over half an acre, the property includes a main house and detached guest house with separate driveways and mature landscaping.The main home features an open kitchen and dining area, sunken living room, and three bedrooms, plus a finished lower level for added living space. Outdoor highlights include a deck, heated pool, patio, pool house, and outdoor shower.The guest house was built in 2011 and provides additional living space, multiple baths, a garage, and its own private setting. Near conservation land and water access, and just 1.5 miles to town, this property offers strong rental potential and exceptional versatility.

15 Twenty First St N, Edgartown

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$2,950,000
4 Beds ⋅ 3 Baths ⋅ 73522670 MLS
This classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a blend of comfort and Vineyard charm. The main living level is bright and airy, featuring a sun-filled kitchen that opens to a sitting area. Sliders lead to a spacious mahogany deck. This level also includes an additional family room, a generously sized bedroom with access to a private terrace and a full bath. Upstairs, the 3rd floor is dedicated to the primary suite, with vaulted, beamed ceilings and walls of glass that flood the space with natural light. The bath features a glass shower, completing the quiet atmosphere. On the first floor, you’ll find a third bedroom, large bath with laundry, and an additional living area with direct access to a covered porch. Set on a generous 0.7-acre lot, the property includes an outdoor shower. The property also boasts a strong rental history. Please inquire

13 Young Street, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..
$2,195,000
5 Beds ⋅ 4 Baths ⋅ 73520213 MLS
Life on Chappaquiddick has a rhythm all its own — and this exceptional compound is designed to savor every moment of it.Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own considered retreat, complete with covered porch, back deck, and outdoor shower. An oversized garage with loft provides additional space to gather and unwind.A circular drive and pea stone pathways connect the buildings across beautifully layered grounds. Adirondack chairs ring a custom firepit for late nights under the stars; a sauna and cold plunge pool on a bluestone patio create your own personal spa. An enclosed garden, garden shed, and multiple outbuildings complete the setting — your own private park among Martha’s Vineyard most beautiful natural setting.

7 Pip'n Circle, Edgartown

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..
$2,895,000
3 Beds ⋅ 2 Baths ⋅ 73511131 MLS
Set in a private community, Sweetened Water Farm offers the pastoral charm of Martha's Vineyard's rural up-island, just minutes from the energy of downtown Edgartown. Residents share access to the association's horse barn and common pastures, ideal for keeping horses or other livestock, adding to the farm's authentic agrarian character. This custom-built home is a true Vineyard gem, crafted over time by local artisans and set against sweeping pastoral views. The main house currently offers 3 bedrooms and 2 bathrooms, with the potential to expand to 6 bedrooms, as approved by the Edgartown Board of Health and Building Department. Inside, the home tells its own story: African mahogany millwork in the library, massive fieldstone fireplaces, and a Jotul wood stove . Built to the same exacting standard, the barn and garage include a custom wood-fired sauna and a two-room office on the second floor.

24 Beetle Swamp Rd, Edgartown

Listing courtesy of Listing Agent: Kathleen Dawson from Listing Office: Donnelly + Co..
$2,950,000
4 Beds ⋅ 3 Baths ⋅ 73494371 MLS
Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a fireplace and a separate TV/family room. The kitchen includes stainless steel appliances, quartz countertops, and a breakfast bar. An eat-in area opens to a spacious mahogany deck, complete with outdoor seating and beautifully landscaped gardens. The first-floor primary suite features vaulted, beamed ceilings and offers a private retreat with an en-suite bath. An additional bedroom/office and a fully renovated hall bath are also located on this level. Upstairs, 2 guest bedrooms share a full bath, while a loft above the two-car garage provides a flexible bonus space.

2 Bold Meadow Road, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..
$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..
$2,399,000
4 Beds ⋅ 3 Baths ⋅ 73472929 MLS
This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres. of pristine conservation land, with scenic trails, abundant wildlife, and direct ocean access. Whether you're seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque has it all. With

76 Washque Ave, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$2,700,000
4 Beds ⋅ 5 Baths ⋅ 73471802 MLS
Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for four.  The first floor hosts a primary suite with a luxurious private bath. Upstairs, you’ll find a cozy second living room and two spacious guest suites, each with private baths. The property includes a 900 sq ft detached accessory dwelling, complete with full kitchen, bath, and bedroom. With one acre of land, this property is poised for a future pool. Ready for your 2026 occupancy!  Note: This property is subject to M.G.L. Chapter 40A Section 6 of the Affordable Homes Act: Single-family residence not to exceed 1,850 sq ft of heated living area, min. 3 bedrooms, no short-term rentals.

6 Laura's Way, Edgartown

Listing courtesy of Listing Agent: Michele Casavant from Listing Office: Vineyard Village Realty.

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