Homes for Sale in 02539

/4
$3,495,000
- Land
- 28,314 Sq Ft
- $5,376,923 per Acre
48 Plaintingfield Way Unit 10, Edgartown, MA 02539

Set on an exceptional .65 -acre parcel, this rare offering combines privacy, space, and an unbeatable location just moments from town and the water. The expansive lot offers a unique opportunity to expand and create a custom estate tailored to your vision. Surrounded by mature landscaping and generous outdoor space, the property offers a peaceful retreat while remaining conveniently close to

Julia Smith Donnelly + Co

48 Plaintingfield Way Unit 10, Edgartown, MA 02539
/10
$896,000
- 2 Beds
- 1 Bath
- 834 Sq Ft
21 Clay Pit Rd, Edgartown, MA 02539

This home is walk in ready to enjoy while you let your imagination go to work for this ideal property. Located a short walk along the bike path to Post Office square you will find this quiet location is perfect. You feel the old Vineyard charm along this peaceful lane. This represents the best entry way into Edgartown Real Estate today so do not let this opportunity pass you by. A 3rd bedroom

Jim Joyce Carroll & Vincent R.E.

21 Clay Pit Rd, Edgartown, MA 02539
/30
$2,295,000
- 5 Beds
- 4 Baths
- 3,119 Sq Ft
2 Old Pocha Rd, Edgartown, MA 02539

Tucked away down a quiet country road, this one-of-a-kind Chappaquiddick retreat invites you to exhale the moment you arrive. With no visible neighbors and the sounds of nature all around, the property offers a rare sense of privacy, peace, and timeless island charm.Built in an era when homes were crafted with artistry and intention, this distinctive post-and-beam residence blends warmth,

Jim Feiner Feiner Real Estate

2 Old Pocha Rd, Edgartown, MA 02539
/26
$3,850,000
- Land
- 1.14 Acres
- $3,377,193 per Acre
10 Pease Point Rd Unit 57, Edgartown, MA 02539

PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned at the end of a private drive, on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Possibility of a fourth-bedroom with proper

Emma Bryant Studio Realty

10 Pease Point Rd Unit 57, Edgartown, MA 02539
/56
$3,695,900
- 3 Beds
- 4.5 Baths
- 3,056 Sq Ft
9 Thaxter Ln, Edgartown, MA 02539

A CONTEMPORARY KATAMA RETREAT, NEWLY REFRESHED AND READY FOR SUMMER. Set in one of Edgartown’s most coveted coastal enclaves, this contemporary retreat captures the effortless rhythm of Katama living: sun-filled interiors, generous gathering spaces, ocean breezes, and a private backyard oasis designed for long summer days by the pool. Moments from South Beach, this tri-level contemporary offers

Wendy Harman

Compass | Point B

9 Thaxter Ln, Edgartown, MA 02539
/30
$1,850,000
- 4 Beds
- 2.5 Baths
- 2,064 Sq Ft
99 Old Purchase Rd, Edgartown, MA 02539

Enjoying a private setting at the end of a quiet Edgartown cul-de-sac, this post-and-beam home is set on .71 acres with easy access to more than 25 acres of Land Bank conservation land. Conveniently located near Morning Glory Farm, the bike path, downtown Edgartown, and South Beach, the property offers both privacy and accessibility. Filled with natural light, the home features a well-designed

Stephanie Roache Donnelly + Co

99 Old Purchase Rd, Edgartown, MA 02539
/51
$7,999,000
- 7 Beds
- 6.5 Baths
- 7,133 Sq Ft
9 Sutton's Way, Edgartown, MA 02539

Nestled in an enviable Katama setting, this masterfully designed shingle-style farmhouse compound epitomizes the peak of casual Vineyard luxury across a manicured coastal landscape. From the sprawling covered entry porch, the front door opens into an impeccably choreographed layout where a grand entry hall flows seamlessly into an expansive great room, an elegant formal dining space and a

Jennifer DaSilva Compass | Point B

9 Sutton's Way, Edgartown, MA 02539
/33
$1,225,000

$25K PRICE DROP
- 3 Beds
- 2 Baths
- 1,338 Sq Ft
37 Dodgers Hole Rd, Edgartown, MA 02539

This split-level home in the highly desirable Dodger’s Hole neighborhood offers a central location with easy access to VTA bus routes, the bike path, all down-island towns and both South Beach and State Beach. The main level features a bright and open living room, dining area, and kitchen designed for comfortable island living. A hallway leads to the primary bedroom with private bath, along with

Beth Welch Viewpoints

37 Dodgers Hole Rd, Edgartown, MA 02539
/25
$1,696,000

$199K PRICE DROP
- 4 Beds
- 2 Baths
- 1,638 Sq Ft
21 Schoolhouse Rd, Edgartown, MA 02539

Located in the heart of Katama between South beach and Edgartown Village. Biking or walking distance along the the shared use path to beach or town. With 2 first floor bedrooms along with a full bath for one floor living. Second floor has 2 more bedrooms, bath along with a loft area for extra bed space. The full basement could be finished off for additional living areas. Plenty of room to grow on

Jim Joyce Carroll & Vincent R.E.

21 Schoolhouse Rd, Edgartown, MA 02539
/66
$2,675,000

$275K PRICE DROP
- 4 Beds
- 8 Baths
- 3,740 Sq Ft
15 21st St N, Edgartown, MA 02539

Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main

Jennifer O'hanlon Compass LLC

15 21st St N, Edgartown, MA 02539
/52
$2,195,000
- 5 Beds
- 3.5 Baths
- 2,628 Sq Ft
7 Pip'N Rd, Edgartown, MA 02539

A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everything in between.Gather around the custom firepit under a canopy of stars, soak in the sauna and

Dawn Bellante-Holand Sandpiper Realty

7 Pip'N Rd, Edgartown, MA 02539
/29
$2,950,000
- 4 Beds
- 3 Baths
- 2,208 Sq Ft
13 Young St, Edgartown, MA 02539

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

Stacy Ickes Donnelly + Co.

13 Young St, Edgartown, MA 02539
/56
$9,995,000
- 6 Beds
- 7.5 Baths
- 7,205 Sq Ft
25 Lelands Path, Edgartown, MA 02539

YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent residence is privately sited at the end of a winding drive on 16.4 acres, offering more than 7,200

Wendy Harman

Compass | Point B

25 Lelands Path, Edgartown, MA 02539
/30
$6,995,000
- 4 Beds
- 3 Baths
- 2,624 Sq Ft
103 Edgartown Bay Rd, Edgartown, MA 02539

Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an

Bonnie Pierce Wallace & Co. Sotheby's International Realty

103 Edgartown Bay Rd, Edgartown, MA 02539
/41
$2,195,000
- 5 Beds
- 3.5 Baths
- 2,628 Sq Ft
7 Pipn Cir, Edgartown, MA 02539

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

Dawn Bellante Sandpiper Realty, Inc.

7 Pipn Cir, Edgartown, MA 02539
/35
$3,850,000
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
10 Pease Point Rd, Edgartown, MA 02539

PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Possible fourth-bedroom opportunity with proper permiting and approvals.

Emma Bryant Studio Realty

10 Pease Point Rd, Edgartown, MA 02539
/42
$21,500,000
- 10 Beds
- 14 Baths
- 7,598 Sq Ft
56 N Summer St, Edgartown, MA 02539

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha’s Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant

Alyssa Halisky Wallace & Co. Sotheby's International Realty

56 N Summer St, Edgartown, MA 02539
/5
$439,500
- Land
- 24,393 Sq Ft
- $784,821 per Acre
5 Candle Maker Cir, Edgartown, MA 02539

Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows

Alyssa Halisky Wallace & Co. Sotheby's International Realty

5 Candle Maker Cir, Edgartown, MA 02539
/33
$3,150,000
- 4 Beds
- 3.5 Baths
- 2,791 Sq Ft
8 Atwood Cir, Edgartown, MA 02539

This charming and historic home is ideally situated at the head of Atwood Circle, a private neighborhood just off Dunham Road, and only a short stroll to town. Recently renovated, the residence blends classic character with modern comfort. The main level features a spacious living room, a cozy den with fireplace, a dining area, and an updated kitchen—perfect for both everyday living and

Gerrett Conover Landvest MV

8 Atwood Cir, Edgartown, MA 02539
/22
$1,000,000

$100K PRICE DROP
- 2 Beds
- 1 Bath
- 1,118 Sq Ft
4 5th St N, Edgartown, MA 02539

An exciting rare find off the Edgartown / Tisbury road directly across from the bike path. The first floor open plan includes a fire place, family room and kitchen with a walk out to the wrap around porch. Two pleasant bedrooms and a full bath are on the first floor. The upper level loft opens to the living room visually expanding the living space. The house has the benefit of a full basement

Doug Burke Signal House Group at Compass

4 5th St N, Edgartown, MA 02539
/6
$2,795,000
- Land
- 3.05 Acres
- $916,393 per Acre
Lot 4B Browns Farm Ln Unit 10, Edgartown, MA 02539

Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy

Courtney Marek Sandpiper Realty

Lot 4B Browns Farm Ln Unit 10, Edgartown, MA 02539
/22
$8,900,000
- 4 Beds
- 8 Baths
- 7,767 Sq Ft
4 Jacobs Neck Rd, Edgartown, MA 02539

Great Potential with Pond & Beach Access ~Set on ten private wooded acres in the Boldwater community, this unique property combines privacy, flexibility, and exceptional potential. It includes a beautifully appointed guest house ready to enjoy, plus an approximately 5,400 sq. ft. structure offering the opportunity to create a custom main residence with a swimming pool. Owners enjoy deeded

Deb Hancock Hancock Real Estate

4 Jacobs Neck Rd, Edgartown, MA 02539
/7
$2,795,000
- Land
- 3.05 Acres
- $916,393 per Acre
Lot 4A Browns Farm Ln Unit Portion of 10, Edgartown, MA 02539

Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore.

Courtney Marek Sandpiper Realty

Lot 4A Browns Farm Ln Unit Portion of 10, Edgartown, MA 02539
/21
$19,900,000
- 5 Beds
- 7 Baths
- 6,577 Sq Ft
33 Boldwater Rd, Edgartown, MA 02539

Experience the timeless beauty of Martha's Vineyard from this luxurious waterfront retreat where the landscape feels so effortlessly connected to daily life. This property embodies understated luxury and timeless design, featuring a meticulously crafted stone residence and guest house. The setting overlooking Edgartown Great Pond has a sandy pond beach and deeded access to the pristine Atlantic

Deb Hancock Hancock Real Estate

33 Boldwater Rd, Edgartown, MA 02539
/6
$2,795,000
- Land
- 0 Sq Ft
Lot 4B Browns Farm Ln, Edgartown, MA 02539

Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy

Courtney Marek Sandpiper Realty, Inc.

Lot 4B Browns Farm Ln, Edgartown, MA 02539
/3
$1,650,000
- Land
- 1.57 Acres
- $1,050,955 per Acre
63 Division Rd Unit 46, Edgartown, MA 02539

LOT #4 - The last lot available in this 5-lot Edgartown subdivision! 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 new residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own

Cheri Mason Landvest MV

63 Division Rd Unit 46, Edgartown, MA 02539
/34
$10,850,000

$400K PRICE DROP
- 7 Beds
- 8 Baths
- 10,142 Sq Ft
14 Trapps Pond Rd, Edgartown, MA 02539

Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. This is one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in a Vineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from the oversized

Gerrett Conover Landvest MV

14 Trapps Pond Rd, Edgartown, MA 02539
/6
$2,795,000
- Land
- 0 Sq Ft
Lot 4A Browns Farm Ln, Edgartown, MA 02539

Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore.

Courtney Marek Sandpiper Realty, Inc.

Lot 4A Browns Farm Ln, Edgartown, MA 02539
/41
$4,600,000

$200K PRICE DROP
- 4 Beds
- 3.5 Baths
- 3,715 Sq Ft
9 Martha's Way, Edgartown, MA 02539

ONE MILE FROM HISTORIC EDGARTOWN VILLAGE; Welcome to this NEWLY CONSTRUCTED gorgeous gambrel home with a POOL that is close to SOUTH BEACH and EDGARTOWN VILLAGE! This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home presents an inviting covered porch with free standing columns, a granite entry step, mahogany decking and shiplapped ceiling. Attention to

Michele Casavant Vineyard Village Realty

9 Martha's Way, Edgartown, MA 02539
/37
$14,500,000

$500K PRICE DROP
- 7 Beds
- 9 Baths
- 6,462 Sq Ft
14 Cow Bay Rd, Edgartown, MA 02539

Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remarkable seclusion,

Gerrett Conover Landvest MV

14 Cow Bay Rd, Edgartown, MA 02539
/40
$2,895,000

$305K PRICE DROP
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
24 Beetle Swamp Rd, Edgartown, MA 02539

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

Kathleen Dawson Donnelly + Co.

24 Beetle Swamp Rd, Edgartown, MA 02539
/42
$6,275,000
- 4 Beds
- 5.5 Baths
- 4,136 Sq Ft
10 Tilton Way, Edgartown, MA 02539

This Greek Revival style home blends timeless architecture with a bright, modern open floor plan, all presented in impeccable condition. A welcoming front foyer leads into a beautifully appointed kitchen featuring high-end appliances, a large center island, and seamless flow into the dining and living areas. The living room is anchored by a fireplace and filled with natural light throughout.

Gerrett Conover Landvest MV

10 Tilton Way, Edgartown, MA 02539
/26
$7,850,000

$150K PRICE DROP
- 4 Beds
- 6 Baths
- 5,884 Sq Ft
24 Katama Bay View Rd, Edgartown, MA 02539

This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighted by a cozy fireplace and

Tom Wallace Wallace & Co. Sotheby's International Realty

24 Katama Bay View Rd, Edgartown, MA 02539
/6
$2,300,000
- 3 Beds
- 2.5 Baths
- 2,016 Sq Ft
60 Crocker Dr, Edgartown, MA 02539

Close to South Beach! Close to Katama Airpark and nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start from scratch to make it your own. The main house is a reverse-style home with a

Sheila Morse Island Real Estate

60 Crocker Dr, Edgartown, MA 02539
/6
$1,125,000
- Land
- 10,018 Sq Ft
- $4,891,304 per Acre
15 Chapman La, Edgartown, MA 02539

Opportunity Abounds - This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the benefits of

Wendy Harman

Compass

15 Chapman La, Edgartown, MA 02539
/6
$550,000

$100K PRICE DROP
- Land
- 1.02 Acres
- $538,529 per Acre
23 Calebs Common Ln Unit 101, Edgartown, MA 02539

CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create your own island retreat. Per the Board of Health, the lot may support a three-bedroom home with an

Katherine Donahue Sandpiper Realty

23 Calebs Common Ln Unit 101, Edgartown, MA 02539
/6
$550,000

$100K PRICE DROP
- Land
- 1.02 Acres
- $539,216 per Acre
23 Calebs Common Ln, Edgartown, MA 02539

CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create your own island retreat. Per the Board of Health, the lot may support a three-bedroom home with an

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

23 Calebs Common Ln, Edgartown, MA 02539
/46
$2,400,000
- 5 Beds
- 3.5 Baths
- 3,873 Sq Ft
50 Hidden Cove Rd, Edgartown, MA 02539

Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering

Sean Federowicz Landmarks at TODAY Real Estate

50 Hidden Cove Rd, Edgartown, MA 02539
/28
$2,950,000
- 4 Beds
- 3 Baths
- 2,927 Sq Ft
2 Bold Meadow Rd, Edgartown, MA 02539

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

Stacy Ickes Donnelly + Co.

2 Bold Meadow Rd, Edgartown, MA 02539
/20
$2,495,000
- 1 Bed
- 1.5 Baths
- 1,236 Sq Ft
218 Upper Main St, Edgartown, MA 02539

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

Madelyn Silvia Wallace & Co. Sotheby's International Realty

218 Upper Main St, Edgartown, MA 02539

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