Dukes County MA Homes for Sale

/31
$1,799,999
- 3 Beds
- 2 Baths
- 1,540 Sq Ft
43 N Slope Ln, Chilmark, MA 02535

Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

Barbara O'Hara

NorthStar Real Estate, LLC

(508) 850-0854

43 N Slope Ln, Chilmark, MA 02535
/12
$1,495,000
- 4 Beds
- 4 Baths
- 2,304 Sq Ft
33 Alyssa Ln, Vineyard Haven, MA 02568

Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary

Stephanie Burke

Portfolio Properties

(508) 687-6441

33 Alyssa Ln, Vineyard Haven, MA 02568
/34
$3,250,000
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
6 Brewster Ave, Oak Bluffs, MA 02557

Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

Katherine Donahue Sandpiper Realty Inc

6 Brewster Ave, Oak Bluffs, MA 02557
/23
$3,100,000
- 1 Bed
- 1 Bath
- 1,250 Sq Ft
114 Meeting House Way, Edgartown, MA 02539

3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach

Rose Ryley Wallace & Co. Sotheby's International Realty

114 Meeting House Way, Edgartown, MA 02539
/7
$4,500,000
- 15 Beds
- 12.5 Baths
- 7,250 Sq Ft
11 Macs Ln, Tisbury, MA 02568

A unique opportunity to own a one of a kind property complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first

Madelyn Silvia Wallace & Co. Sotheby's International Realty

11 Macs Ln, Tisbury, MA 02568
/42
$2,395,000
- 4 Beds
- 3 Baths
- 1,918 Sq Ft
21 & 25 Fulling Mill Rd, Chilmark, MA 02535

Jessie Holtham Wallace & Co. Sotheby's International Realty

21 & 25 Fulling Mill Rd, Chilmark, MA 02535
/42
$2,575,000
- 4 Beds
- 2.5 Baths
- 1,910 Sq Ft
76 Washque Ave, Edgartown, MA 02539

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

76 Washque Ave, Edgartown, MA 02539
/61
$2,250,000
- 5 Beds
- 3.5 Baths
- 3,250 Sq Ft
28 Pine Tree Ln, Vineyard Haven, MA 02568

Enjoy beach-close living—just 0.2 miles to the shore—in sought-after West Chop. This welcoming 5BR/3.5BA colonial blends classic Vineyard character with New Roof '26, modern comforts, including central air, an updated kitchen, and three fireplaces. Approximately 3,152± sq ft (expanded from 2,632± with a 520± sq ft finished space over the garage) offers flexible, easy flow to a large fenced

Lisa Da Silva Compass | Point B

28 Pine Tree Ln, Vineyard Haven, MA 02568
/28
$2,295,000
- 4 Beds
- 3.5 Baths
- 2,690 Sq Ft
151 Tashmoo Ave, Vineyard Haven, MA 02568

The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to

Brenda Galligan Karen M. Overtoom R.E.

151 Tashmoo Ave, Vineyard Haven, MA 02568
/2
$2,700,000
- 4 Beds
- 4.5 Baths
- 2,750 Sq Ft
6 Laura's Way, Edgartown, MA 02568

Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for

Michele Casavant Vineyard Village Realty

6 Laura's Way, Edgartown, MA 02568
/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
/65
$2,690,000
- 6 Beds
- 4 Baths
- 2,618 Sq Ft
55 Old House Way, West Tisbury, MA 02575

Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms & 3 bathrooms in Main & 2 bedrooms & 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with stainless

Leslie Graham Anchor Realty of Martha's Vineyard

55 Old House Way, West Tisbury, MA 02575
/28
$2,495,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
268 Tashmoo Ave, Vineyard Haven, MA 02568

Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

Michele Casavant Vineyard Village Realty

268 Tashmoo Ave, Vineyard Haven, MA 02568
/23
$2,260,000
- 4 Beds
- 3.5 Baths
- 2,810 Sq Ft
4 High Meadow Ln, Oak Bluffs, MA 02557

Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

Kate Burnside Portfolio Properties

4 High Meadow Ln, Oak Bluffs, MA 02557
/39
$2,500,000
- 3 Beds
- 4 Baths
- 2,300 Sq Ft
229 Oak Ln, West Tisbury, MA 02575

A hidden gem in West Tisbury! Beautifully manicured, fenced in 2.2 - acre parcel with 100% privacy, and 84 evergreen trees. This modern, contemporary well maintained home is 3-bedroom, 3 bath with two levels of living and a partially finished basement. The first floor is a sunlight filled, open kitchen and dinning room, with hardwood floors throughout. There are multiple decks leading out to a

Doug Burke Cronigs Real Estate

229 Oak Ln, West Tisbury, MA 02575
/39
$3,250,000
- 5 Beds
- 3.5 Baths
- 4,068 Sq Ft
241 Daggett Ave, Vineyard Haven, MA 02568

Built in 2016 by Squash Meadow Builders, this exceptional five bedroom Colonial sits moments from the sandy shores of Tashmoo Beach on Vineyard Sound. Spanning four levels, it blends timeless architecture with modern comfort. The main floor offers open living with gas fireplace, a gourmet kitchen with custom built-ins and bench seating, and a sunlit sunroom for relaxed coastal living. A private

Alyssa Halisky Wallace & Co. Sotheby's International Realty

241 Daggett Ave, Vineyard Haven, MA 02568
/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
/3
$2,700,000
- 4 Beds
- 4.5 Baths
- 2,750 Sq Ft
6 Lauras Way, Edgartown, MA 02539

Coastal Luxury Meets Versatility in EdgartownWelcome to a rare opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a sprawling one-acre plot with a stunning detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, sun-drenched living room featuring a wall of glass sliders that erase the boundary

Michele Casavant Vineyard Village Realty

6 Lauras Way, Edgartown, MA 02539
/44
$2,700,000
- 4 Beds
- 3 Baths
- 1,399 Sq Ft
34 Windemere Rd, Oak Bluffs, MA 02557

Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to

JoJo Lambert Island Home Realty Inc.

34 Windemere Rd, Oak Bluffs, MA 02557
/27
$2,825,000
- 5 Beds
- 2 Baths
- 2,386 Sq Ft
187 Lagoon Pond Rd, Vineyard Haven, MA 02568

For the very first time, the historic Ben Luce Homestead (circa 1850) is being offered on the open market. This charming farmhouse blends rich Island history with timeless appeal.Once home to Benjamin Norton Luce (1840–1912) — Civil War veteran, blacksmith, and town constable — the property sits on 1.5 acres of pastoral land and offers 5 bedrooms, 2 full baths, solar panels, barn, and a newly

Erin Leighton Compass

187 Lagoon Pond Rd, Vineyard Haven, MA 02568
/9
$2,250,000
- 3 Beds
- 3.5 Baths
- 2,475 Sq Ft
35 Double Ox Rd, Oak Bluffs, MA 02557

Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase$700,000 and building contract $1,550,000.This 3-bedroom dream home is set in an elevated

Marilyn Moses Ocean Park Realty Inc

35 Double Ox Rd, Oak Bluffs, MA 02557
/58
$2,495,000
- 3 Beds
- 3.5 Baths
- 3,530 Sq Ft
61 Causeway Rd, Vineyard Haven, MA 02568

Welcome to this fabulous property nestled just a short stroll from all the best of Vineyard Haven. Easily accessible and within close proximity to the ferry, downtown shops, restaurants, galleries, Owen Park Beach, and the MV Playhouse, the location is ideal. This beautifully designed home has been lovingly maintained and offers a wonderful balance of Vineyard charm and modern convenience.

Stephanie Roache Donnelly + Co

61 Causeway Rd, Vineyard Haven, MA 02568
/67
$2,300,000
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
70 Spring St, Vineyard Haven, MA 02568

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 and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable

June Flake Viewpoints

70 Spring St, Vineyard Haven, MA 02568
/30
$2,950,000
- 3 Beds
- 2.5 Baths
- 1,845 Sq Ft
33 Ocean Ave, Oak Bluffs, MA 02557

A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and

Marcia Sullivan Garvey Donnelly + Co.

33 Ocean Ave, Oak Bluffs, MA 02557
/32
$560,000
- 1 Bed
- 1.5 Baths
- 590 Sq Ft
21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

Diana Gilmore Island Real Estate

21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
/18
$1,100,000
- 2 Beds
- 2 Baths
- 1,583 Sq Ft
25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

Maranda Post Compass | The O'Hanlon Group

25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
/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
/7
$3,100,000
- Land
- 3.04 Acres
- $1,019,737 per Acre
114 Meeting House Way, Edgartown, MA 02539

3 Acre Katama Building Lot with Existing Guest House.This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South

Rose Ryley Wallace & Co. Sotheby's

114 Meeting House Way, Edgartown, MA 02539
/4
$625,000
- Land
- 0.34 Acre
- $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
/9
$2,450,000
- Land
- 5.37 Acres
- $456,238 per Acre
9 Maqua Way, Edgartown, MA 02539

Chappaquiddick: Beautiful 5-acre parcel offering private frontage on Katama Bay. The generous-sized lot affords plenty of development flexibility, with the ability to capture the view from nearly any location. Located on Maqua Way, a quiet subdivision just off the paved road, the property is conveniently situated near all the Chappy favorites: beaches, trails, a community center, and Slip Away

Katherine Donahue Sandpiper Realty Inc

9 Maqua Way, Edgartown, MA 02539
/15
$2,490,000
- Land
- 7.2 Acres
- $345,833 per Acre
3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539

Build your dream home on the special 7.2 acre North lot 1 private wooded property with 1/2 ownership in the beautiful 4.5 acre meadow in the grand Boldwater Association(BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all

Robert Kenney Tea Lane Associates

3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539
/43
$14,500,000
- 4 Beds
- 4.5 Baths
- 3,705 Sq Ft
64 Squibnocket Farm Rd, Chilmark, MA 02535

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

Thomas Wallace Wallace & Co. Sotheby's

64 Squibnocket Farm Rd, Chilmark, MA 02535
/19
$10,500,000
- 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
/30
$1,595,000
- 5 Beds
- 3 Baths
- 1,810 Sq Ft
22 Old Lighthouse Rd, Vineyard Haven, MA 02568

Located in a quiet enclave off Main Street, Vineyard Haven and just a half-mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical,

Jessie Holtham Wallace & Co. Sotheby's International Realty

22 Old Lighthouse Rd, Vineyard Haven, MA 02568
/7
$1,575,000
- 2 Beds
- 1 Bath
- 924 Sq Ft
47 Quenames Rd, Chilmark, MA 02535

On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

Dawn Bellante Sandpiper Realty, Inc.

47 Quenames Rd, Chilmark, MA 02535
/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
/15
$835,000
- 2 Beds
- 1 Bath
- 768 Sq Ft
51 Lantern Ln, Vineyard Haven, MA 02568

Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance

Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

51 Lantern Ln, Vineyard Haven, MA 02568
/15
$610,000
- 2 Beds
- 1 Bath
- 704 Sq Ft
124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island. At the bottom of the hill you will find

Rene Jackson Island Real Estate

124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
/19
$14,950,000
- 6 Beds
- 9 Baths
- 1,320 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 SternMcCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details.Upon entering,

Tom Wallace Wallace & Co. Sotheby's International Realty

68 N Water St, Edgartown, MA 02539
/49
$849,000
- 1 Bed
- 1 Bath
- 803 Sq Ft
26 Winthrop Ave, Oak Bluffs, MA 02557

Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile

Alisan Lohan-Conway Alisan Lohan-Conway Properties

26 Winthrop Ave, Oak Bluffs, MA 02557

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