Edgartown Massachusetts homes for sale starting at Fifty Thousand Dollars

$3,649,000 - Edgartown, MA

7 Whistling Swan Circle Edgartown, MA - Located in the sought-after Island Grove neighborhood, this Edgartown home is near Morning Glory Farm, Downtown, and South Beach. Designed for entertaining, the first floor features a custom kitchen, dining and living rooms, den, screened porch, half bath, and a seamless flow to outdoor living and a new heated pool. A spacious first-floor primary suite includes a walk-in closet and full bath. Upstairs offers four bedrooms and two full baths. The finished lower level includes a living room with gas fireplace, wet bar, and full bath. Additional highlights: access to association tennis courts, two laundry rooms, two-car garage, four-zone HVAC, and mature landscaping. Recent updates include a heated pool with auto cover, outdoor shower, lighting, paint, and new appliances. The property is connected to town sewer which allows for up to six bedrooms.

$3,600,000 - Edgartown, MA

110 Fifth Street North Edgartown, MA - 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, is flooded with light, open to breezes, and marries a timeless Vineyard vibe with modern luxury. The mudroom entryway opens to the kitchen with an expansive breakfast island, dining room, and living room with a gas fireplace. Sliders from the living room open to the heated pool and hot tub surrounded by granite pavers. The kitchen shares a view of the pond and Nantucket Sound through the wall of windows and sliders in the dining room out to the deck, a perfect spot for outdoor dining. A wine cooler in the dining room has a pass-through space above it to the adjacent family room. The open floor plan lets the cook connect with family and guests. Beyond the kitchen, accessed through a sliding barn door, is a cleverly placed office with built-in bookshelves and sliders to the deck. A pantry, half bath, laundry, and another mudroom adjacent to the outdoor shower complete the first floor. The views of Sengekontacket and Nantucket Sound become more dramatic on the second and third floors. There are 4 bedrooms on the second floor, including 2 primary suites, all with vaulted shiplap ceilings, as well as a den and a shared bath. The den and one of the suites have private decks that capture the essence of the views. A second sliding barn door opens to the den, creating a private primary wing at the front of the house. An outstanding spiral staircase provides access to the fabulous "Lookout Lounge," where you will enjoy exceptional views inside and outside on 2 decks. The professionally landscaped yard includes a perennial garden, mature trees and shrubs, and a rolling lawn with a fire pit. It's only steps away from the hiking trails of Felix Neck Wildlife Sanctuary, a short trip to the town landing, and an easy drive or bike ride to downtown Edgartown. With ample spaces for relaxation, entertainment, and multiple living areas, this home is the perfect Vineyard experience. First Floor: The mudroom entrance leads directly into the kitchen, which boasts an enormous breakfast island with plenty of room for casual dining. Sliders in the cozy living room with a gas fireplace lead directly to the pool and spa. The dining room, with sliders to the expansive deck, is on the right, with direct access to the family room. Separated by a sliding barn door is an office and a second mudroom that leads to the outdoor shower. A half bath and laundry room complete this floor. Second Floor: Two primary suites on this floor enjoy pleasant views of Sengekontacket and Nantucket Sound. A barn door off one of the suites opens to a den with a private deck overlooking the water. There are two additional bedrooms and a shared full bath on this floor. Third Floor: An impressive spiral staircase leads you to the third level. This space has been ordained the "Lookout Lounge" because of the impressive and expansive views with 2 decks, which both take advantage of the views. A truly spectacular experience!

$3,100,000 - Edgartown, MA

114 Meetinghouse Way Edgartown, MA - Discover this private Katama retreat, perfectly situated on over 3 acres of forested and landscaped grounds. Located just a mile from Edgartown Great Pond and a little over 2 miles from both South Beach and Edgartown Village, this contemporary guesthouse offers the ultimate island escape. Built in 2018, it boasts a proven rental history and is outfitted with every modern amenity. With a 6-bedroom septic system already in place, there's ample opportunity to expand by adding a main house or additional structures, pending necessary town approvals. Enjoy now while envisioning its full potential!

$2,650,000 - Edgartown, MA

16 Mockingbird Drive Edgartown, MA - Experience the ultimate Vineyard getaway in this custom Colonial that perfectly balances sophistication with Island charm. This thoughtfully designed property features soaring 9-foot ceilings, authentic Heart Pine flooring, and a show-stopping gourmet kitchen complete with professional-grade Viking appliances, handcrafted soapstone countertops, and a statement Carrara marble island. The spacious floor plan offers four bedrooms and four full bathrooms, complemented by two powder rooms and a fully finished lower level for additional entertainment. Separate guest quarters above the garage provide visitors with their own private retreat, featuring a dedicated living room, convenient wet bar, and private deck. Outdoors, a mahogany deck overlooks beautifully landscaped gardens, with an outdoor shower perfect for post-beach rinses before alfresco dining under the stars. Conveniently located just a short distance from downtown Edgartown's acclaimed restaurants, boutiques, and harbor, this property offers a quintessential Vineyard experience and an established rental history. Note: Additional finished space of approximately 700 SF in the finished basement. (not included in total on list sheet)

$2,550,000 - Edgartown, MA

11 Bernard Way Edgartown, MA - Located at the end of a quiet cul de sac, just half a mile to the top of Main Street, is this 4-bedroom home with a separate studio guest apartment, office, and heated 2-car garage with 10-ft doors. There is also an unfinished full basement. The living space is in excellent condition with a combination of hardwood, carpet, and tile floors. This light and bright home could be a reliable income producer or might be appropriate for the buyer who needs space for guests or employee housing. There is a 10.14 kilowatt rooftop solar array installed by South Mountain Company.

$2,499,000 - Edgartown, MA

24 Dark Woods Road Edgartown, MA - Welcome to 24 Dark Woods Road, a beautifully maintained 3-bedroom, 3.5-bath Contemporary Colonial nestled in an upscale, tranquil neighborhood. This spacious residence abuts acres of Sheriffs Meadow conservation land, offering miles of trails, serene pond views and peaceful privacy at the end of a quiet road, yet is just a mile from the beach and closer to Edgartown Village. This association prides itself in complementing and maintaining the natural surroundings. Step into the entryway to a sunlit, front-facing kitchen featuring granite countertops, custom cabinetry and coordinated built-in desk. The open-concept living room boasts soaring ceilings, a commodious dining area and a wall of sliders leading out to a backyard deck perfect for outdoor living and future expansion. The first-floor primary bedroom with ensuite bath, second bedroom, full bath and study, provide convenience and comfort. An open stairway leads to the second floor with a balcony overlooking the living room, where you'll discover a cozy versatile den, a large third bedroom, full bath and a bright office space. This property has town sewer available at the start of the driveway. Up to 6 bedrooms allowed with a connection to town sewer. There is interior unfinished space on the second level of the home for interior expansion possibilities. Large unfinished basement with interior access and bulkhead. Mudroom/Laundry room with half bath and large closet. Outdoor shower off the deck. Many energy updates. Solar panels. Hear pump system for heat and a/c. Back up oil heating system in place.

$2,275,000 - Edgartown, MA

43C Dark Woods Road Edgartown, MA - Enjoy the convenience of Dark Woods, a quiet neighborhood in an ideal location close to the Village, bike path, beaches, and 27 acres of Sheriff's Meadow conservation land. Tucked in the woods of the pleasant Dark Woods community, this property has been meticulously maintained and is ready for your enjoyment. Sited on a pleasant .77-acre lot, the property offers expansive space with a floor plan that is perfect for entertaining. The first floor features a fabulous living room with a gas fireplace and a formal dining room. Overlooking a private backyard is the open eat-in kitchen with direct access to a 2-tiered deck with a hot tub and outdoor shower, where you will spend much of your time entertaining. A bar/pantry is conveniently located between the dining room and kitchen, and a laundry room off the kitchen. If you are looking to retreat, enjoy the bonus space above the 2-car garage. The primary ensuite with a newly renovated bathroom is cleverly located on the right side of the second floor for privacy and 2 large guest bedrooms and another newly renovated bathroom complete this floor. The lower level enjoys a large walk-out bedroom with direct access to the backyard and a

$1,950,000 - Edgartown, MA

16 Schoolhouse Road Edgartown, MA - Vacation Getaway in Edgartown Estates - This sunny and welcoming contemporary home could be yours this summer! With an open layout, vaulted ceilings, and lots of windows and glass doors, the home feels bright and airy. Step outside to a spacious wrap-around deck—great for relaxing or entertaining. Inside, the living, dining, and kitchen areas flow nicely and are just the right size for gathering. The first floor has three guest bedrooms, while upstairs you'll find a loft, the primary bedroom suite, and a private balcony. Other features include hardwood floors, air conditioning, a full basement, and an outdoor shower—perfect after a day at the beach. The half-acre lot offers a nice lawn with mature trees and plantings that give privacy from the road and neighbors. Edgartown Estates is an excellent location, just off the bike path to South Beach or into Edgartown Village. Come take a look!

$1,950,000 - Edgartown, MA

13 Hotchkiss Lane Edgartown, MA - A beautifully maintained post and beam home situated at the end of a quiet lane in Katama. When you enter the home, you get a sense of the quality and care taken to preserve this truly special property. The entrance foyer opens into a comfortable living area with a handsome fireplace, stairway to the second floor and half bath with full laundry. The dining area has access to the enclosed screened-in porch, and the fully appointed kitchen offers countertop seating and a centered butcher block Island. The side entrance from the outdoor bluestone patio opens to the first-floor hallway and the den/office. The other side of the first floor is a hallway to the primary full bathroom and bedroom with cathedral ceiling. The interior of the house is graced with red oak, post & beam design and complimented with natural pine interior doors and wood trim throughout. The handsome Brazilian Teak flooring adds to the charm of this first floor. The second floor is accessed by an attractive pine staircase that leads to an open sitting area. There are two bedrooms with a shared bathroom. New Andersen windows installed in May of 2025. The perfect vacation home or year-round living.

$1,895,000 - Edgartown, MA

32 Flamingo Drive Edgartown, MA - This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first floor has hardwood flooring throughout, and the living room is open to the kitchen area. A separate formal dining area is adjacent to the kitchen with a full bathroom located in between. The primary bedroom has a vaulted ceiling, tiled bathroom with an air bubble jet tub, double sinks, and large walk-in closet. The second floor has four generous size carpeted bedrooms and a full bathroom. The lower level is partially finished creating additional living space to enjoy and can easily become a home theater room. The laundry room is in the basement area with a sink and storage cabinets. House is equipped with a central vacuum system. Many recent updates include a new furnace in 2023, AZEK exterior trim and deck railings. Currently a five-bedroom dwelling with a septic design for six bedrooms. A great investment property for year-round living or rental income.

Edgartown, Massachusetts listings for sale

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