Edgartown, MA 5 Bedroom Homes for Sale

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Newest Edgartown, MA 5 Bedroom Homes for Sale

$3,950,000

5 Beds ⋅ 5 Baths ⋅ 73592553 MLS

Welcome home to this meticulously renovated Martha's Vineyard property, where coastal elegance meets effortless indoor-outdoor living. Offered fully furnished, "turn-key" ready and spanning over 4,100 square feet of beautiful living space, this property offers a total of 5 bedrooms and 4.5 baths between the main house and detached 1 bedroom guest suite. In the main house, the spacious great room boasts cathedral ceilings, wood-burning fireplace, and glass doors that seamlessly connect the interior to the outdoors. The custom kitchen is outfitted with an expansive granite center island, stainless steel appliances and a generous dining area. The private primary retreat includes a custom walk-in closet and en suite bath, featuring a double sink vanity and a walk-in shower with dual shower heads. 3 private guest rooms and 2 additional full baths, located on a separate floor, ensure plenty of privacy for everyone. The finished basement offers approximately 670 square feet of additional living space to the main house and is perfect for entertaining, complete with a custom bar, built-in cabinetry, and a half bath. The detached 1 bedroom and 1 bath guest suite is located above the oversize 2-bay garage and is ideal for extended family and friends. This beautifully appointed space features an open floor plan, high-end materials throughout and a large private deck. From the moment you arrive, the professionally landscaped grounds invite you to enjoy everything this property has to offer. With dedicated outdoor entertaining areas, multiple decks, outdoor tv, firepit and hot tub, the space is perfectly designed for both grand hosting and quiet relaxation. This exceptional property checks off all the boxes for the perfect Vineyard home.

6 Hollow Way, Edgartown

Listing courtesy of Listing Agent: Theresa Geary from Listing Office: Donnelly + Co..

$4,195,000

5 Beds ⋅ 4 Baths ⋅ 73586815 MLS

Nestled within Edgartown’s coveted Katama/Island Grove enclave, 32 Martha’s Road is a masterfully crafted 2023 modern farmhouse where elevated design meets the effortless elegance of Vineyard living. Built by renowned island builder Shawn Chapps, this five-bedroom residence is a study in sophistication—rich with architectural intention, bathed in natural light, and thoughtfully composed for both intimate daily living and memorable entertaining. Set on .5 acres, the home unfolds across approximately 3,594 square feet, with an additional 2,300+ square feet of high-ceilinged, unfinished basement space offering extraordinary future potential. Cathedral ceilings, refined millwork, and expansive windows throughout create an atmosphere of lightness and luxury. A soaring, cathedral-height entryway immediately captivates, framed by striking two-story windows that draw the eye through the home to the serene, professionally landscaped backyard beyond. The foyer’s scale and natural light set the tone for the residence’s modern, airy aesthetic. The open-concept kitchen, dining, and living areas form an inviting central gathering space anchored by a warm gas fireplace and illuminated by windows on both sides. The gourmet kitchen is a true showpiece, featuring Thermador appliances, an expansive center island, and exceptional craftsmanship. It opens to a deep, walk-in pantry and a beautifully designed entertaining area complete with a sink, Zephyr beverage refrigerator, generous shelving, and abundant storage—functioning perfectly as a wet bar when hosting family and friends. Just beyond, a stunning screened porch extends the living space outdoors, offering a wood-burning fireplace and direct access to the stone patio and level backyard. With ample room for recreation and the potential for a future pool, the property invites endless enjoyment. With commanding curb appeal, flexible expansion opportunities, and abundant outdoor space, 32 Martha’s Road stands as an exceptional offering in one of Edgartown’s most desirable neighborhoods. Beautifully conceived, crafted with care, and designed with intention, this modern farmhouse is ready to be made uniquely your own—a rare opportunity to enjoy Vineyard living at its most refined.

32 Marthas Road, Edgartown

Listing courtesy of Listing Agent: Patricia Lyman from Listing Office: Compass.

$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

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

$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..

$21,700

5 Beds ⋅ 3 Baths ⋅ 73313240 MLS

YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky and shimmering sea. Grab bikes from the garage and hop on a path to visit picturesque Edgartown for boutique shopping and dining or head to historic Oak Bluffs for ice cream and carousel rides. Enjoy a day at the beach with boogie boards, chairs and cooler in tow before returning to the cottage for a barbecue where an additional first floor kitchen makes for effortless entertaining. Unwind in the primary bedroom and greet the sunrise with coffee on the balcony. Four more bedrooms and living areas easily accommodate everyone. WEEKLY RENTAL OPTIONS AVAILABLE

97 3rd St N, Edgartown

Listing courtesy of Listing Agent: Fine Homes Group from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.

$19,000

5 Beds ⋅ 5 Baths ⋅ 73007813 MLS

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all on the first floor. French doors lead out to a screened in porch. Five spacious bedrooms located on the second floor feature private or shared baths, and a spacious mahogany deck overlooking the landscaped backyard. This is an ideal in-town Edgartown vacation home.

19 Morse St Ed333, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$56,800

5 Beds ⋅ 4 Baths ⋅ 72844897 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool surrounded by meadows and lots of privacy. Take the Boston Whaler motor boat or kayak across Oyster Pond to private beach (used by Presidents Clinton and Obama in past summers.) Outdoor and indoor games galore to entertain..Crocquet, horseshoes, ping pong and a pool table in the finished basement... 2 master bedroom suites with king beds, and separate guest quarters with a king bedroom and bath. One bedroom with twin beds. Newly added hot tub for you to enjoy!

2 Nonamesset Rd Ed319, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$100,000

5 Beds ⋅ 4 Baths ⋅ 72843894 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $25,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gorgeous waterfront home is well equipped with gourmet kitchen, stone fireplace, numerous sitting areas, and multiple decks each with water views over the Edgartown Harbor. Both the main and upper level have beautiful master suites and also washers & dryers. Easy access to downtown Edgartown, South Beach and the Bike Path. A lush green path leads you down to the dock and boat house, where there is also a mooring for larger boats.

60 Witchwood Lane Ed317, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$50,000

5 Beds ⋅ 5 Baths ⋅ 72843706 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to the beach. The location is close to South Beach and downtown Edgartown.

17 Edgartown Bay Rd Ed328, Edgartown

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

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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.

Edgartown, MA 5 Bedroom Homes for Sale

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