Dukes County MA Homes for Sale

/40
$1,895,000
- 4 Beds
- 3.5 Baths
- 2,061 Sq Ft
174 Middle Rd, Chilmark, MA 02535

Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

Sheila Morse Island Real Estate

174 Middle Rd, Chilmark, MA 02535
/42
$3,199,000
- 3 Beds
- 3.5 Baths
- 3,082 Sq Ft
53 Stoney Hill Rd, Vineyard Haven, MA 02568

This custom-built residence is nestled in one of Martha’s Vineyard’s most coveted up-island towns. At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, Wolf stove and wall oven, Sub-Zero refrigerator, Miele dishwasher, Kohler farmhouse sink, and Rohl satin nickel gooseneck faucet. A custom bar is appointed with

Jennifer B. DaSilva Compass

53 Stoney Hill Rd, Vineyard Haven, MA 02568
/4
$625,000
- Land
- 14,997 Sq Ft
- $1,815,277 per Acre
0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

Andrew McElhinney Compass LLC

0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
/4
$675,000
- Land
- 9,997 Sq Ft
- $2,941,176 per Acre
0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568

Oak Bluffs Buildable Lot – Prime LocationThis flat 3-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to

Andrew McElhinney Compass LLC

0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
/10
$330,000
- Land
- 1.26 Acres
- $261,905 per Acre
0 Moshup Trail Unit 27 & 146 43498, 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

0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535
/19
$9,250,000
- 5 Beds
- 2.5 Baths
- 2,794 Sq Ft
33 Goethals Way, Vineyard Haven, MA 02568

A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the

Buder Team Sandpiper Realty, Inc.

33 Goethals Way, Vineyard Haven, MA 02568
/36
$5,325,000
- 6 Beds
- 4 Baths
- 2,890 Sq Ft
4 Canonicus Ave, Oak Bluffs, MA 02557

Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

4 Canonicus Ave, Oak Bluffs, MA 02557
/20
$925,000
- 2 Beds
- 1 Bath
- 834 Sq Ft
21 Clay Pit Rd, Edgartown, MA 02539

EDGARTOWN COTTAGE ON A COUNTRY LANE - Nestled on a spacious .56-acre lot in the Lily Pond District, this charming 2-bedroom, 1-bath cottage offers a rare opportunity to create your own Island haven. Renovate or build to suit just a short distance from all that Edgartown village has to offer — shops, restaurants, harbor, and beaches — you’ll enjoy both privacy and convenience in one of the

Leslie C. Floyd Portfolio Properties

21 Clay Pit Rd, Edgartown, MA 02539
/42
$1,275,000
- 3 Beds
- 1 Bath
- 1,033 Sq Ft
9 Brunswick Ave, Oak Bluffs, MA 02557

PRIME LOCATION! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively UPDATED inside and out. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts NEW flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new

Alice Pierce Coldwell Banker Realty - Martha's Vineyard

9 Brunswick Ave, Oak Bluffs, MA 02557
/41
$2,950,000
- 5 Beds
- 4 Baths
- 3,361 Sq Ft
735 Franklin St, Vineyard Haven, MA 02568

Welcome to this stunning 4-bedroom, 3-bathroom primary residence along with a 1-bedroom studio apartment over the one-car garage, ideally located in West Chop! Together, they include approximately 3,871 square feet of beautifully renovated living space (an additional 510 sqft of living space on the 3rd floor in the main house is not included on the town assessment). Situated on a .99-acre lot,

Emily Flake Viewpoints

735 Franklin St, Vineyard Haven, MA 02568
/36
$1,390,000
- 4 Beds
- 2 Baths
- 1,332 Sq Ft
40 Scotchmans Ln, Vineyard Haven, MA 02568

A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

Jim Osmundsen Donnelly + Co.

40 Scotchmans Ln, Vineyard Haven, MA 02568
/4
$4,800,000
- 4 Beds
- 4.5 Baths
- 3,816 Sq Ft
7 Marthas Rd, Edgartown, MA 02539

Welcome to this coastal chic farmhouse set in the heart of Katama, a few blocks from the Field Club, close to SOUTH BEACH and close to Edgartown Village. To be built is a four bedroom en-suite home with a heated saltwater POOL. This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home offers an inviting covered porch with free standing columns, a granite entry

Michele Casavant Vineyard Village Realty

7 Marthas Rd, Edgartown, MA 02539
/40
$4,800,000
- 6 Beds
- 5.5 Baths
- 5,394 Sq Ft
23 Pinehurst Rd, Edgartown, MA 02539

New Construction with POOL, GUEST HOUSE and PRIMARY HOME, all within close proximity to Main Street, Edgartown. This four bedroom gambrel homes welcomes you with a two story foyer which opens to a great room with a gourmet kitchen, a bar area and a central island offering seating for at least four. The kitchen flows into the open dining and living room with a gas fireplace. The great room

Michele Casavant Vineyard Village Realty

23 Pinehurst Rd, Edgartown, MA 02539
/4
$4,800,000
- 4 Beds
- 4.5 Baths
- 3,816 Sq Ft
7 Martha's Way, Edgartown, MA 02539

Welcome to this coastal chic farmhouse set in the heart of Katama, a few blocks from the Field Club, close to SOUTH BEACH and close to Edgartown Village. To be built is a four bedroom en-suite home with a heated saltwater POOL. This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home offers an inviting covered porch with free standing columns, a granite entry

Michele Casavant Vineyard Village Realty

7 Martha's Way, Edgartown, MA 02539
/42
$9,499,000
- 4 Beds
- 7 Baths
- 5,902 Sq Ft
43 Peases Point Way S, Edgartown, MA 02539

Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown's most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

43 Peases Point Way S, Edgartown, MA 02539
/8
$3,495,000
- Land
- 11.49 Acres
- $304,178 per Acre
0 Pocha Rd, Edgartown, MA 02539

CHAPPAQUIDDICK -Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to 1⁄2 mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your backyard.

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

0 Pocha Rd, Edgartown, MA 02539
/8
$3,495,000
- Land
- 11.39 Acres
- $306,848 per Acre
0 Pocha Road Extension Unit 1.1,1.2 43325, Edgartown, MA 02539

CHAPPAQUIDDICK - Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to 1⁄2 mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding, and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your

Katie Donahue Sandpiper Realty

0 Pocha Road Extension Unit 1.1,1.2 43325, Edgartown, MA 02539
/55
$4,450,000
- 6 Beds
- 4.5 Baths
- 2,960 Sq Ft
104 Pond View Farm Rd, Vineyard Haven, MA 02568

Two homes on over 3 flat acres of waterfront on the Tisbury Great Pond. This remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond.Both the main house and guest house boast unobstructed water views, creating a

Alexis Holden Tea Lane Associates

104 Pond View Farm Rd, Vineyard Haven, MA 02568
/8
$695,000
- Land
- 11,417 Sq Ft
- $2,651,660 per Acre
35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557

GOING, GOING... GONE!This is the LAST 3-bedroom lot available in Cluster C.12 lots SOLD 9 homes already built.Welcome to Lagoon Ridge Oak Bluffs’ newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes.The lot is ready

Marilyn Moses Ocean Park Realty Inc

35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
/29
$2,275,000
- 2 Beds
- 1.5 Baths
- 1,176 Sq Ft
9 Moshup Trail, Aquinnah, MA 02535

Spectacular property in Aquinnah, featuring a newly installed and town-approved 6-bedroom septic system, ready to support your vision for expansion and renovation. Located on 4.7 acres filled with rolling meadows and stone walls, this property boasts a truly remarkable barn that was transported from Maine, and rebuilt on the Island. The grandfathered-in barn spans approximately 61' by 45' with

Patrick McCarthy Grace Hagerty Real Estate Inc

9 Moshup Trail, Aquinnah, MA 02535
/4
$445,000
- Land
- 23,958 Sq Ft
- $809,091 per Acre
11 Boylston Dr Unit 1.314, Edgartown, MA 02539

A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island’s top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

Alyssa Halisky Wallace & Co. Sotheby's

11 Boylston Dr Unit 1.314, Edgartown, MA 02539
/28
$22,950,000
- 7 Beds
- 8.5 Baths
- 8,200 Sq Ft
60 Bartimus Luce Rd, Vineyard Haven, MA 02568

This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design,

Gerrett Conover Landvest MV

60 Bartimus Luce Rd, Vineyard Haven, MA 02568
/39
$12,500,000
- 5 Beds
- 3.5 Baths
- 3,700 Sq Ft
18 Spruce Gate Rd, Chilmark, MA 02535

Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm—a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the

Alyssa Halisky Wallace & Co. Sotheby's

18 Spruce Gate Rd, Chilmark, MA 02535
/37
$1,195,000
- 4 Beds
- 2 Baths
- 2,059 Sq Ft
4 Rock Pond Rd, Vineyard Haven, MA 02568

4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and sunlight

Kerry Quinlan-Potter Breakwater MV

4 Rock Pond Rd, Vineyard Haven, MA 02568
/4
$2,995,000
- 4 Beds
- 4.5 Baths
- 3,024 Sq Ft
9 Hagerty Dr, Tisbury, MA 02568

West Chop Dream Home in the Making! Experience the charm of this brand-new Shingle Style Colonial, currently under construction. Featuring 4 spacious bedrooms, 4 full and one half bath. This thoughtfully designed home offers generous space. Venture outside into your private oasis, complete with an in-ground pool (36' x18') — perfect for sun-soaked afternoons and evening gatherings. Situated in a

Lisa Gilberto C McManus Realty Group

9 Hagerty Dr, Tisbury, MA 02568
/12
$1,295,000
- Land
- 4.4 Acres
- $294,318 per Acre
37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535

This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation, NHESP has been completed and there are no restrictions on the lot, there's a septic design and the

Elissa Lash Tea Lane Associates

37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
/43
$1,600,000
- 3 Beds
- 3 Baths
- 1,737 Sq Ft
150 Cove Rd Unit 10, Vineyard Haven, MA 02568

The Premiere Townhouse at Tashmoo Wood. Elegantly renovated, this sun-filled end unit is fresh and modern with fine finish details. From the moment you step onto the expanded wrap-around deck, you will begin to see the fine craftsmanship of the property. Walk through the front entry and you will gain further appreciation for the meticulous attention to detail. Expansive windows fill the living

Michele Moore Island Real Estate

150 Cove Rd Unit 10, Vineyard Haven, MA 02568
/2
$799,000
- Land
- 39,996 Sq Ft
- $870,181 per Acre
22 Bramble Path Unit 214, West Tisbury, MA 02568

Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

Michele Casavant Vineyard Village Realty

22 Bramble Path Unit 214, West Tisbury, MA 02568
/2
$799,000
- Land
- 39,639 Sq Ft
- $878,022 per Acre
22 Bramble Path, West Tisbury, MA 02568

Flat building lot centrally located in West Tisbury. A perc test has been done that supports a four bedroom title five system. It is the buyers responsibility to install utilities, well and septic.

Michele Casavant Vineyard Village Realty

22 Bramble Path, West Tisbury, MA 02568
/29
$10,950,000
- 4 Beds
- 3.5 Baths
- 2,050 Sq Ft
16 Shotnaigher Ln, Chilmark, MA 02535

New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet

Rebecca V Conroy Conroy & Company R.E., Inc.

16 Shotnaigher Ln, Chilmark, MA 02535
/31
$2,395,000
- 4 Beds
- 3 Baths
- 1,918 Sq Ft
25 Fulling Mill Rd, Chilmark, MA 02535

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

Thomas Wallace Wallace & Co. Sotheby's

25 Fulling Mill Rd, Chilmark, MA 02535
/4
$465,000
- Land
- 9,997 Sq Ft
- $2,026,144 per Acre
0 California Ave Unit 76 42933, Oak Bluffs, MA 02568

Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows for a one bedroom home of any size. Water and electric are nearby.

Jim Joyce Carroll & Vincent R.E.

0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
/42
$7,950,000
- 5 Beds
- 7 Baths
- 4,531 Sq Ft
85 Reservoir Rd, Vineyard Haven, MA 02568

Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

Alyssa Halisky Wallace & Co. Sotheby's

85 Reservoir Rd, Vineyard Haven, MA 02568
/63
$2,999,000
- 8 Beds
- 7.5 Baths
- 3,770 Sq Ft
72 Chappaquiddick Ave, Edgartown, MA 02539

WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the

Michele Casavant Vineyard Village Realty

72 Chappaquiddick Ave, Edgartown, MA 02539
/4
$1,875,000
- Land
- 24,393 Sq Ft
- $3,348,214 per Acre
11A Duarte Cir, Edgartown, MA 02539

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

David White OwnerEntry.com

11A Duarte Cir, Edgartown, MA 02539
/12
$2,950,000
- 3 Beds
- 1 Bath
- 936 Sq Ft
9 N Neck Rd, Edgartown, MA 02539

COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming,

Leslie C. Floyd Portfolio Properties

9 N Neck Rd, Edgartown, MA 02539
/73
$3,200,000
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
70 Spring St, Vineyard Haven, MA 02568

NOW INCLUDING RARE 12,527 S.F. TOWN APPROVED BUILDING LOT ON WILLIAM STREET! Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House*, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District, just two blocks to all the shops, restaurants, galleries, town beach, tennis,

June Flake Viewpoints

70 Spring St, Vineyard Haven, MA 02568
/7
$2,500,000
- Land
- 1.4 Acres
- $1,785,714 per Acre
2 Other House Rd Unit 173, Chilmark, MA 02535

Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in

Russell Maloney Russell Maloney Real Estate

2 Other House Rd Unit 173, Chilmark, MA 02535
/27
$14,250,000
- 6 Beds
- 9 Baths
- 4,820 Sq Ft
68 N Water St, Edgartown, MA 02539

This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown’s finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon

Thomas Wallace Wallace & Co. Sotheby's

68 N Water St, Edgartown, MA 02539
/27
$8,950,000
- 5 Beds
- 7 Baths
- 4,078 Sq Ft
1 Field Club Dr, Edgartown, MA 02539

Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and

Thomas Wallace Wallace & Co. Sotheby's

1 Field Club Dr, Edgartown, MA 02539

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