Edgartown, Massachusetts listings for sale

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$1,895,000 - Edgartown, MA
99 Old Purchase Road Edgartown, MA - Welcome to this charming post and beam-style home, privately located at the end of a cul-de-sac on .71 acres with proximity to over 50 acres of Land Bank and Sheriff's Meadow land with multiple trails and paths. Conveniently located to the bike path, Morning Glory Farm, the heart of Edgartown, and Meetinghouse Way, with direct access to South Beach, the location is ideal. The floor plan was designed to bathe in natural light, creating a relaxing and inviting atmosphere. The first floor features a fabulous kitchen for the accomplished chef with a large island, desk space, and a walk-in pantry with direct access to the kitchen garden. The dining room enjoys a gorgeous enamel pellet stove and sliders to the expansive deck for outdoor entertaining. The sunken cathedral-ceiling living boasts a stunning floor-to-ceiling brick fireplace with remarkable sunlight and sliders to the deck. The first-floor bedroom is at the back of the house, adjacent to the full bath. The large primary suite with den/office space and a half bath is on the second floor, and two additional bedrooms and a full bath with a skylight complete this floor. The basement offers room for storage and overflow. Outside, enjoy the pleasant front yard, spacious deck, gardens, and outdoor shower in the back. Town sewer connection permits expansion of up to 7 bedrooms. Come and experience this Vineyard retreat with unparalleled privacy, ready for immediate enjoyment. First Floor: The entrance to this delightful home is a welcoming mudroom, where you can leave your shoes and hang your coats! A first-floor bedroom is at the back of the house, adjacent to a full bath. The kitchen is designed for the consummate chef with a large island, plenty of cabinets for storage, a walk-in pantry that leads to the garden, and a cleverly placed desk area. The dining area enjoys a fabulous pellet stove and sliders to the spacious deck. Step down into the dramatic cathedral-ceiling living room with a wood-burning fireplace, skylights to capture great natural light, and another set of sliders to the deck. Second Floor: The primary bedroom occupies the entire left side of this floor, with a half bath and den/office space. There are two additional bedrooms on this floor and a full bath with a walk-in shower and skylight. If you are looking for more storage space, there is plenty of room in the large pull-down attic. Basement: The basement is accessed through the inside of the home and the exterior bulkhead. With 1200 square feet, there is room for storage and extended living space.
1985 | 4 | 2 | 2,064 sqft.
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$1,795,000 - Edgartown, MA
16 Hye Road Edgartown, MA - Edgartown House and Guest House located close to Morning Glory Farm and less than 2 miles to downtown. The main house was recently freshened up and features an open floor plan with 3 bedrooms/2 baths. Freshly painted throughout. The wood floors on the first floor were refinished. New carpet on the stairs and luxury vinyl flooring with extra cushion on the second floor. The main and guest house crawl spaces were re-insulated in 2018. The main house furnace propane/hot air furnace was replaced in 2021. Two mini-splits provide air conditioning. The privately sited guest house has 2 bedrooms/1 baths. Seller will be connecting to town sewer prior to closing. Once that is completed, the property will support up to 6 bedrooms.
1981 | 5 | 3 | 2,020 sqft.
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$1,750,000 - Edgartown, MA
15 Jernegan Pond Road Road Edgartown, MA - Simply enchanting! The setting is picturesque with a pond, towering trees and flowering shrubbery, privately tucked away yet less than 1¼ mile to the Edgartown Village. The existing home is set at the edge of the pond and is awaiting reimagination and renovation. Parcel will support 5 bedrooms once connected to municipal sewer. Structures are being sold 'as is'.
1945 | 2 | 2 | 2,042 sqft.
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$1,650,000 - Edgartown, MA
60 Windsor Drive Edgartown, MA - Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy access to all island amenities, including beaches, bike paths, state forests, and public transportation. Step inside to discover a bright and airy first floor, adorned with hardwood floors and a cozy fireplace. The spacious eat-in kitchen boasts stainless steel appliances and granite countertops, complemented by a slider leading to a sprawling deck overlooking manicured landscaping and gardens. On the first floor, you'll find a convenient bathroom and one bedroom, while the second floor hosts a generously sized primary bedroom with abundant natural light and a skylight. Two additional bedrooms and another full bathroom complete the second level, offering ample space for family and guests. Don't miss out on the opportunity to make this exceptional Edgartown property your own.
1997 | 4 | 2 | 1,666 sqft.
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$1,650,000 - Edgartown, MA
16 Majors Cove Lane Edgartown, MA - Nestled in the prestigious Majors Cove community, this lovingly maintained home offers the perfect blend of comfort, style, and Vineyard charm. Enjoy access to exceptional amenities, including tennis courts, a boat launch ideal for kayaking to State Beach, and proximity to the bike path for easy access to Edgartown, Oak Bluffs, and Vineyard Haven. Set on a pleasantly landscaped lot, this inviting home is filled with natural light. The heart of the home is the cathedral-ceiling living room, centered around a classic wood-burning fireplace ~ an inviting space for gatherings year-round. The open kitchen and dining area seamlessly connect to a spacious new deck, offering an ideal setting for outdoor entertaining or quiet relaxation. A convenient mudroom with laundry sits just off the dining area and provides direct access to the attached garage. Two comfortable bedrooms and a full bathroom complete the main level. The upper level is devoted entirely to the private primary suite. This serene retreat features a generous bedroom, a dressing area, a walk-in closet, and a full bath complete with a soaking tub and separate shower. Additional highlights include a full basement and the quintessential Vineyard outdoor shower. Offered furnished, this property is your opportunity to enjoy the very best of Island life. First Floor: The cathedral-ceiling living room with a wood-burning fireplace is the focal point of the home and offers an abundance of natural light. Enjoy the open kitchen and dining area with direct access to the expansive new deck for extended outdoor living. The mudroom with laundry is off the dining area with direct access to the garage. Two bedrooms and a full bathroom complete this floor. Second Floor: The second floor is dedicated to the spacious and private primary suite. There is a dressing area, a walk-in closet, and full bath with a soaking tub and shower. Basement: Full unfinished basement with plenty of room for storage.
1986 | 3 | 2 | 1,965 sqft.
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$1,625,000 - Edgartown, MA
6 Gerts Way Edgartown, MA - In the heart of Katama, close to south beach and all that the area has to offer, is this traditional 3 bedroom cape with updates. The bright kitchen and dining area offer a modern space, perfect for entertaining. A vaulted ceiling makes the living room light and bright. Three bedrooms, one downstairs and two upstairs, share bathrooms on each level. An outdoor shower, screened porch and outdoor decks make the indoor / outdoor transition comfortable. This property has an excellent rental history, or make it your island getaway or year round home. Sold turn key, as is.
1986 | 3 | 2 | 1,400 sqft.
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$1,600,000 - Edgartown, MA
467 Katama Road Unit: B2 Edgartown, MA - Mattakesett units continue to be in high demand and #B2 is the only unit currently on the market! Take advantage of all the Winnetu Resort amenities and a robust rental program which covers your fees and provides great revenue! This unit offers abundant views of the farm fields out front, open common space next to and behind, and is a short walk or bike to South Beach! There are 3 bedrooms, 2.5 baths and the bonus of a finished loft. With over 1,400 sq ft of living space this is one of the larger units. The outdoor rear deck offers additional space for dining or relaxing after a day at the beach. These units are seasonal, closed down in mid-November and re-opened starting in mid-April. This unit is being offered fully furnished. Available to be shown now, but will be limited to Thursdays, rental turnover day, starting in late May.
1973 | 3 | 2 | 1,411 sqft.
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$1,495,000 - Edgartown, MA
5 Pip'n Road Edgartown, MA - Tucked away in a quiet, wooded setting on picturesque Chappaquiddick, this charming three-bedroom Cape offers a peaceful island retreat. Designed for laid-back living, the home features a cheerful and versatile floor plan with generous indoor and outdoor spaces. The star of the show? A sprawling screened-in porch with a cozy wood-burning fireplace-perfect for summer nights or crisp fall evenings. The backyard is a private oasis, backing up to conservation land for lasting serenity. Direct access to the nearby walking trails means adventure is right outside your door. Less than a mile away, the calm, swimmable waters of Katama Bay beckon, ideal for paddling, picnicking, and memory-making. Whether you're seeking a peaceful escape or a fun-filled summer basecamp, this lovingly maintained home is move-in ready and waiting to welcome you.
1971 | 3 | 2 | 1,800 sqft.
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$1,495,000 - Edgartown, MA
11 Flamingo Drive Edgartown, MA - Located in the Dodger's Hole subdivision is this inviting four bedrooms plus office, two-bathroom cape style home. The property has been well cared for and is a delight to view. Sited on .5 acres of land with a pea stone driveway, wraparound deck, and outdoor shower with new enclosure. The antique garage is a great storage space for lawn equipment, garden supplies or small vehicle. The living room is open to the tiled eat-in kitchen area and the hallway leads to a pantry, full bathroom and two first floor bedrooms. The second floor offers a full bathroom and two generously sized bedrooms. The interior has been completely painted and sparkles brand new with new paint on ceilings, walls, windows, doors, baseboard heaters, and all trim. Brand new carpeting in the first-floor hallway and bedrooms. Do not miss the opportunity to purchase this great investment!
2002 | 4 | 2 | 1,820 sqft.
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$1,395,000 - Edgartown, MA
35 Seventh Street North Edgartown, MA - Welcome to this charming Cape-style home, ideally located with easy access to the bike path, public transportation, and just a short distance to the Village. Set on a spacious half-acre lot, this delightful property has been lovingly maintained by the same family since it was built, with thoughtful updates made over the years. The home features an open layout that seamlessly blends comfort and functionality, making it perfect for both everyday living and entertaining. A sun-filled living room with cathedral ceilings and sliders opens to a multi-level deck—ideal for outdoor gatherings. Adding to the fabulous outdoor space is the large, shady, covered front porch! The kitchen, dining area, which comfortably accommodates 10, and cozy sitting space with a wood-burning stove also offer direct access to the deck. The primary bedroom and a full bath are on the first floor, and a comfortable loft bedroom with built-in drawers occupies the second floor. There is an office in the basement and ample space for storage. Adding even more versatility to the property is a one-bedroom apartment above the detached garage—perfect for guests, rental income, or a peaceful retreat. Enjoy the tranquility of the expansive yard - ideal for gardening, outdoor play, or simply soaking in the serene surroundings. Whether you're looking for your first home, a retreat from the city, or a place to grow, this charming Cape has it all. The abutting .5-acre lot, 27 Seventh Street North, is also available for sale, offering even more possibilities for expansion or investment. First Floor: The open floor plan on the first floor allows for easy living and entertaining. The kitchen, dining and seating area with a wood-burning stove occupy the center of the home and enjoy access to the fabulous deck for outdoor entertaining. The cathedral-ceiling living room is the focal point of the home with sliders to the deck. The primary bedroom and full bath are beyond the kitchen. Second Floor: This floor is dedicated to an open loft bedroom. Apartment above the 2-car garage: Enjoy the privacy of this 1-bedroom apartment above the detached 2-car garage. The space enjoys a full kitchen, bathroom, bedroom, a living room, and creative overflow space with room for a set of bunk beds. There is a large deck off the kitchen and access from both the front and back side of the garage. A true gem!
1980 | 3 | 2 | 1,814 sqft.