Zip codes 02539 homes for sale starting at Fifty Thousand Dollars

$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.

$2,349,000 - Edgartown, MA

11 Norton Street Edgartown, MA - EDGARTOWN HISTORIC DISTRICT - Terrific opportunity for an INVESTOR and HOMEOWNER alike to have an in town House and Guest house on this size lot in wonderful part of Town, on a lovely Street. Two cottages - One at the front and one at the rear of lot. Yard and parking for each cottage. Room to have a beadevelop the yard and the property in general. Presently a three (3) bedroom lot but Town Sewer is available on Norton Street and once connected FOUR (4) Bedrooms will be allowed. Off Street Parking. Walk to the Harbor, Edgartown Yacht Club, Restaurants, Stores. Many possibilities to enhance!! Tenants in place, but easy to show with reasonable notice. Shared driveway. Being sold in "As Is" condition.

$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

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.

$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.

$1,875,000 - Edgartown, MA

11A Duarte Circle Edgartown, MA - Nestled in the HEART OF KATAMA, this ready-to-build unique deep lot offers the opportunity to create your DREAM COMPOUND just minutes to Edgartown Center & South Beach. Set back on a pristine cul-de-sac this property provides unparalleled privacy for a home in Katama with a country vibe. The SIX BEDROOM COMPOUND allows a MAIN HOUSE, GUEST HOUSE, GARAGE and has amble space for outdoor entertaining with an in-ground pool, pool house/kitchen and more. In a small enclave with several new 5-6-million-dollar homes on oversized lots with natural buffers, you will enjoy unparalleled privacy with quick access to Edgartown Village shops, restaurants, beaches while walking, running or biking from your doorstep. Water sport enthusiasts have access from Wilson's Landing for kayaking, paddle boarding or boating to enjoy the Land Bank beach and Great Pond. Build to reflect your style and budget in one of the most desirable locations in Edgartown. Architectural renditions are underway to inspire and ensure a seamless transition from vision to construction.

$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.

$1,750,000 - Edgartown, MA

63 Division Road Edgartown, MA - LOT #4 - One of the last lots available in this newly created 5-lot Edgartown subdivision! This group of residences will feature over-sized lots with utilities in place. Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The properties will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own family compound including all of the popular requests such as garage, pool and pool house. The Seller continues to improve the area including the access road and the development. Substantial new construction homes are up on surrounding lots 1, 2, and 5. Lot 4, which is 1.57-acres, is currently being offered and is ready for your design concept.

Zip codes 02539 listings for sale

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