Dukes County MA Homes for Sale

/66
$1,899,000

$101K PRICE DROP
- 5 Beds
- 3.5 Baths
- 2,075 Sq Ft
63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

Valene Pires The Agency

63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
/8
$330,000
- Land
- 1.26 Acres
- $261,905 per Acre
0 Moshup Trail Unit 73508205, Aquinnah, MA 02535

Enjoy coveted access to one of Martha's Vineyard’s most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah’s iconic “Painted House,” the property includes use of a private gated parking area for 1 vehicle and a picturesque stretch of shoreline

Alyssa Halisky Wallace & Co. Sotheby's International Realty

0 Moshup Trail Unit 73508205, Aquinnah, MA 02535
/3
$525,000
- Land
- 10,454 Sq Ft
- $2,187,500 per Acre
Lot 1 Dolan Ave, Tisbury, MA 02568

A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

Lot 1 Dolan Ave, Tisbury, MA 02568
/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
/40
$1,350,000

$45K PRICE DROP
- 4 Beds
- 3 Baths
- 1,305 Sq Ft
46 Kennebec Ave, Oak Bluffs, MA 02557

This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs'

Cathy Gargiulo Ocean Park Realty Inc

46 Kennebec Ave, Oak Bluffs, MA 02557
/25
$7,300,000
- 5 Beds
- 5.5 Baths
- 3,539 Sq Ft
65 Carl's Way, West Tisbury, MA 02568

Stylized Private Waterfront Retreat close to townperched along the tranquil shores of the beloved Tisbury Great Pond, this stunning Hutker-designed waterfront home is a seamless blend of coastal elegance and timeless island charm. Designed to capture the essence of Vineyard living, the home features intimate water views, sun-drenched interiors, and carefully curated finishes

Jill Napior Tea Lane Associates

65 Carl's Way, West Tisbury, MA 02568
/26
$1,850,000
- 4 Beds
- 2 Baths
- 1,833 Sq Ft
22 Old Harbor Ln, Oak Bluffs, MA 02557

Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard.

Lisa Stewart Sandpiper Realty, Inc.

22 Old Harbor Ln, Oak Bluffs, MA 02557
/25
$1,450,000

$100K PRICE DROP
- 5 Beds
- 5 Baths
- 2,266 Sq Ft
345 North Rd, Chilmark, MA 02535

This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected

Jessica Campbell Flanders Real Estate

345 North Rd, Chilmark, MA 02535
/78
$35,000,000
- 8 Beds
- 8 Baths
- 6,841 Sq Ft
146 Quenames Rd, Chilmark, MA 02535

Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

Grace Hagerty Grace Hagerty Real Estate Inc

146 Quenames Rd, Chilmark, MA 02535
/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
/28
$2,395,000

$100K PRICE DROP
- 4 Beds
- 3 Baths
- 1,968 Sq Ft
105 Whalers Walk, Edgartown, MA 02539

Fresh, stylish, and fun best describe this inviting four-bedroom Edgartown home with a newly completed pool! Thoughtfully renovated from top to bottom, the interior offers warm, functional living spaces where every detail has been carefully considered. The same level of attention carries outdoors to a true backyard oasis, complete with a heated saltwater pool, multiple patios, a pergola, and an

Katherine Donahue Sandpiper Realty

105 Whalers Walk, Edgartown, MA 02539
/34
$1,295,000

Open Sun 11AM - 12:30PM $100K PRICE DROP
- 4 Beds
- 2.5 Baths
- 1,783 Sq Ft
51 Summer St, Vineyard Haven, MA 02568

NEWLY PRICED AT $1,295,000 — CLASSIC VINEYARD CHARACTER, THOUGHTFUL UPDATES AND MOVE-IN-READY CONVENIENCE Just moments from Main Street, the harbor, ferry, shops and restaurants, 51 Summer Street offers the warmth of a classic Vineyard home with the comfort of meaningful modern improvements. Originally built in 1950 and extensively renovated and expanded in 2014, this four-bedroom,

Janet Scott eXp Realty

51 Summer St, Vineyard Haven, MA 02568
/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
/14
$5,100,000
- Land
- 2.34 Acres
- $2,182,285 per Acre
7 Overview Ln Unit 47, Oak Bluffs, MA 02557

A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

Alyssa Halisky Wallace & Co. Sotheby's

7 Overview Ln Unit 47, Oak Bluffs, MA 02557
/7
$2,000,000
- Land
- 21,801 Sq Ft
- $3,996,004 per Acre
0 State Rd Unit 29.3, Vineyard Haven, MA 02568

1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

Peter Cronig Cronigs Real Estate

0 State Rd Unit 29.3, Vineyard Haven, MA 02568
/34
$1,499,000

$100K PRICE DROP
- 5 Beds
- 2 Baths
- 1,440 Sq Ft
393 Lighthouse Rd, Aquinnah, MA 02535

Ranch style home & Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Living/Dining as well as the wrap-around deck. Enjoy the open concept main living area, two bedrooms,

Julianna Flanders Flanders Real Estate

393 Lighthouse Rd, Aquinnah, MA 02535
/14
$1,325,000
- Land
- 4.28 Acres
- $309,579 per Acre
0 N Road 15 Belhaven Way Unit 4-2, Chilmark, MA 02535

Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of

Stacy Ickes Donnelly + Co

0 N Road 15 Belhaven Way Unit 4-2, Chilmark, MA 02535
/22
$2,150,000

$100K PRICE DROP
- 3 Beds
- 2 Baths
- 1,867 Sq Ft
237 Lagoon Pond Rd, Vineyard Haven, MA 02568

Ideally located at the beginning of Hines Point, this light-filled, well-maintained home offers a central setting with easy access to the Lagoon, the MV Museum, and town. Public water access is just a short walk away, making it easy to enjoy all the benefits of this special area.Set on a gentle rise overlooking the Lagoon, the home is filled with natural light and offers beautiful water

Alison Rich Carroll & Vincent R.E.

237 Lagoon Pond Rd, Vineyard Haven, MA 02568
/10
$1,325,000
- Land
- 4.28 Acres
- $309,579 per Acre
0 North Way, Chilmark, MA 02535

Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of

Stacy Ickes Donnelly + Co.

0 North Way, Chilmark, MA 02535
/13
$1,645,000
- Land
- 3.32 Acres
- $495,482 per Acre
26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575

Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides - a setting unlike

Dawn Bellante-Holand Sandpiper Realty

26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
/64
$2,579,000
- 4 Beds
- 2 Baths
- 1,399 Sq Ft
34 Windemere Rd, Oak Bluffs, MA 02557

Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full

Alisan Lohan-Conway Alisan Lohan-Conway Properties

34 Windemere Rd, Oak Bluffs, MA 02557
/22
$325,000

$5K PRICE DROP
- Land
- 7,313 Sq Ft
- $1,935,676 per Acre
00 Moshup Trail Unit 6, Aquinnah, MA 02535

Tucked along the south shore of Aquinnah on Martha’s Vineyard, this beach lot presents a chance to enjoy true oceanfront ownership. Accessed via Moshup Trail, this lot features a private gated entry with a pea stone parking area. A boardwalk, that winds through natural coastal vegetation, connects to a sandy trail that brings you over the bluff to the expansive shoreline. Secure your own stretch

Diana Gilmore Island Real Estate

00 Moshup Trail Unit 6, Aquinnah, MA 02535
/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
/39
$3,295,000

$100K PRICE DROP
- 3 Beds
- 4 Baths
- 2,500 Sq Ft
27 Clambelly Rd, Chilmark, MA 02535

A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood

Julianna Flanders Flanders Real Estate

27 Clambelly Rd, Chilmark, MA 02535
/10
$3,750,000

$245K PRICE DROP
- Land
- 1.92 Acres
- $1,956,182 per Acre
98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568

Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views over Sengekontacket Pond to the Vineyard Sound, creating a stunning backdrop for your future Martha’s

Andrew McElhinney Compass LLC

98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568
/34
$1,250,000
- 3 Beds
- 3 Baths
- 1,682 Sq Ft
261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. This well-maintained 3-bedroom, 3-bath end-unit condo offers a rare combination of privacy, space, and access to one of Vineyard Haven’s most sought-after communities. As an end unit with its own private driveway, this home offers added separation and a more single-family feel—along with a one-car garage and additional storage for bikes and beach

Jennifer O'hanlon Compass LLC

261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
/32
$1,755,000

$40K PRICE DROP
- 3 Beds
- 3 Baths
- 2,695 Sq Ft
68 Front St, Oak Bluffs, MA 02557

Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon. Thoughtfully maintained, the sun-filled main level boasts an open floor plan with large windows that frame views of the surrounding property. The generously sized kitchen features

Jayne Isford Ocean Park Realty, Inc.

68 Front St, Oak Bluffs, MA 02557
/32
$1,625,000
- 2 Beds
- 2.5 Baths
- 1,532 Sq Ft
26 Union St Unit 7, Tisbury, MA 02568

Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect

Alyssa Halisky Wallace & Co. Sotheby's

26 Union St Unit 7, Tisbury, MA 02568
/70
$5,295,000

$200K PRICE DROP
- 3 Beds
- 7 Baths
- 3,608 Sq Ft
385 Barnes Rd, Vineyard Haven, MA 02568

SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and

Stephanie Roache Donnelly + Co

385 Barnes Rd, Vineyard Haven, MA 02568
/10
$1,425,000
- Land
- 3.01 Acres
- $473,422 per Acre
38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568

The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated building envelope of

Elissa Lash Tea Lane Associates

38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
/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
/13
$1,645,000
- Land
- 3.32 Acres
- $495,482 per Acre
26 Flint Hill Rd, West Tisbury, MA 02575

Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no

Dawn Bellante Sandpiper Realty, Inc.

26 Flint Hill Rd, West Tisbury, MA 02575
/42
$4,995,000

$655K PRICE DROP
- 4 Beds
- 4.5 Baths
- 5,402 Sq Ft
205 South Rd, Chilmark, MA 02535

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a

Tina Miller Donnelly + Co.

205 South Rd, Chilmark, MA 02535
/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
/53
$6,750,000
- 5 Beds
- 3.5 Baths
- 4,050 Sq Ft
78 Hammett Rd, Chilmark, MA 02535

This magnificent Spring Point waterfront property, perched 50 ft above sea level and 425 ft back from the North Shore bluff, boasts beautiful views of the Vineyard Sound, Aquinnah coastline and the Elizabeth Islands -- and year dramatic year round sunsets. The property at the end of a well maintained wide dirt road 1 mile from North Rd is SECLUDED and TRANQUIL. It's a SHORT WALK TO THE BEACH,

Robert Kenney Tea Lane Associates

78 Hammett Rd, Chilmark, MA 02535
/27
$869,000
- 1 Bed
- 1 Bath
- 797 Sq Ft
37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location Unit #5 comes with an amazing roof top deck that is only shared with one other condo (#4). This well appointed sleeps 4 with custom wood features and a staircase to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area,, large bedroom with alcove, a sleep nook, a tiled

Lisa Lucier Anchor Realty of MV

37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
/20
$899,000
- 2 Beds
- 1 Bath
- 990 Sq Ft
37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2nd floor comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a nautical feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest

Lisa Lucier Anchor Realty of MV

37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
/3
$785,000
- Land
- 3.8 Acres
- $206,579 per Acre
0 Jeffers Way Unit 165, Aquinnah, MA 02535

Nestled within the serene landscape of Aquinnah, this 3.8-acre parcel offers a unique blend of natural beauty and historical significance. Bordered by ancient stone walls and mature vegetation, the elevated terrain provides a bucolic setting for a private residence. Already in place is a private well, 3-bedroom septic, and full engineering.

Michele Casavant Vineyard Village Realty

0 Jeffers Way Unit 165, Aquinnah, MA 02535
/37
$3,999,999

$500K PRICE DROP
- 4 Beds
- 3 Baths
- 2,715 Sq Ft
94 Weaver Ln, Vineyard Haven, MA 02568

Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows

Emma Kennedy Sandpiper Realty, Inc.

94 Weaver Ln, Vineyard Haven, MA 02568
/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

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