Dukes County MA Houses for Sale

/47
$9,795,000
- 6 Beds
- 7 Baths
- 6,135 Sq Ft
52 S Summer St, Edgartown, MA 02539

The historic Captain Ellsworth West House is a landmark property in the very heart of downtown Edgartown, offering an extraordinary combination of history, charm, and modern luxury. Just steps from Edgartown’s celebrated restaurants, galleries, shops, and harbor, this rare estate provides both the convenience of in-town living and the privacy of a graciously designed compound. The main residence

Alyssa Halisky Wallace & Co. Sotheby's

52 S Summer St, Edgartown, MA 02539
Selling your home? Sell it faster and for more with a Homes.com Boost.
Learn More
/23
$1,950,000 Open Tue 12:30PM - 2:30PM
- 3 Beds
- 2 Baths
- 2,237 Sq Ft
10 Duende Ln, Edgartown, MA 02539

Experience the quintessential Martha's Vineyard lifestyle at this charming residence perfectly nestled in a private yet convenient Katama location. This inviting 3-bedroom plus loft, 2-bathroom home is situated on a .52-acre lot, providing ample privacy and outdoor enjoyment. Step inside the light-filled interior featuring multiple windows and skylights that invite the sunshine in. Convenience is

Idalyn Macchia Gilstad Wallace & Co. Sotheby's

10 Duende Ln, Edgartown, MA 02539
/30
$1,500,000
- 1 Bed
- 1 Bath
- 780 Sq Ft
11 Ephriam Allen Rd, West Tisbury, MA 02568

Charming cottage with spectacular water views across stone walls and rolling meadows to Vineyard Sound and the Elizabeth Islands. Set on 1.2 acres, this custom-built home was thoughtfully designed to embrace its serene surroundings, with wood and tile floors, a recent roof (2023), a water filtration system, 3 bedroom septic system, annual maintenance history, and an open-plan kitchen, dining, and

Dawn Bellante-Holand Sandpiper Realty

11 Ephriam Allen Rd, West Tisbury, MA 02568
/25
$1,500,000
- 4 Beds
- 2 Baths
- 1,248 Sq Ft
23 Laurel Ave, Oak Bluffs, MA 02557

LOCATION! YEAR ROUND HOUSE!INVESTMENT PROPERTY!STARTER HOME!A comfortable home in an established, East Chop neighborhood, this four bedroom, two bathroom house is located within walking distance to the Harbor, downtown Oak Bluffs, and the Oak Bluffs Ferries. There is easy access to shops, family entertainment, and the beach. This home provides a welcoming porch and a spacious backyard patio

Sandra Grymes Martha's Vineyard Island-Wide Realty

23 Laurel Ave, Oak Bluffs, MA 02557
/34
$1,395,000
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
1 Ambers Way, Edgartown, MA 02539

This custom three-bedroom post-and-beam home captures the rustic charm and natural beauty of Chappaquiddick. Thoughtfully designed with light-filled spaces and a wood-burning fireplace, the home offers a warm and inviting retreat in every season. A spacious workshop, perfect for the avid outdoorsman, ideal for storing boating, fishing, and woodworking gear. Set on nearly four private acres, the

Katherine Donahue Sandpiper Realty Inc

1 Ambers Way, Edgartown, MA 02539
/57
$1,185,000
- 3 Beds
- 3 Baths
- 1,780 Sq Ft
200 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

Ideally located in the coveted West Chop neighborhood of Tisbury, this desirable 2+ bedroom, 3-bath townhouse in the Tashmoo Wood community offers a rare combination of space, privacy and resort-style amenities. The first floor features a light-filled living room with cathedral ceilings a fireplace, and walls of windows that bring the natural light and views of the surrounding woods. The open

Nora Jardin Island Real Estate

200 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568
/28
$1,500,000
- 1 Bed
- 1 Bath
- 780 Sq Ft
11 Ephraim Allen Rd, Vineyard Haven, MA 02568

Charming cottage with spectacular water views across stone walls and rolling meadows to Vineyard Sound and the Elizabeth Islands. Set on 1.2 acres, this custom-built home was thoughtfully designed to embrace its serene surroundings, with wood and tile floors, a recent roof (2023), and an open-plan kitchen, dining, and living area framing commanding views of the water. Perched at the edge of the

Dawn Bellante Sandpiper Realty Inc

11 Ephraim Allen Rd, Vineyard Haven, MA 02568
/31
$1,150,000
- 2 Beds
- 1 Bath
- 1,040 Sq Ft
73 & 0 Old Country Ln, Vineyard Haven, MA 02568

Charming 2-bedroom, 1-bath ranch house in Vineyard Haven, in town—just minutes from shops, restaurants, and schools. This well-maintained property offers a functional layout with a bright living area, a cozy kitchen overlooking the backyard, two comfortable bedrooms, and a full bathroom. The house has a full basement with ample room for storage and projects. This home is situated on two lots,

Julianna Flanders Flanders Real Estate

73 & 0 Old Country Ln, Vineyard Haven, MA 02568
/11
$915,000
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
8 Hitchings Cir, Oak Bluffs, MA 02557

Nestled in a quiet Oak Bluffs neighborhood, less than a mile from the harbor, beaches, shops, and restaurants, this Cape-style home offers the perfect balance of convenience and tranquility. The interior features an open kitchen and living room, plenty of space for guests, and a full unfinished basement. The two bedroom Title V septic system has passed inspection. Outside, the property features a

Peyton Wallace Studio Realty

8 Hitchings Cir, Oak Bluffs, MA 02557
/39
$1,470,000
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
26 Winne Ave, Vineyard Haven, MA 02568

Welcome to your dream home just a short walk to the lagoon. This home offers easy access for dropping a kayak or taking a refreshing afternoon dip from a public access point. Discover this charming home nestled on a corner lot within a serene neighborhood. This beach home has an updated kitchen and bathrooms. The kitchen is equipped with new appliances and gorgeous quartz countertops, making it a

Joe & Nicole Holland Vineyard Dream Realty LLC

26 Winne Ave, Vineyard Haven, MA 02568
/4
$6,295,000
- 4 Beds
- 5.5 Baths
- 3,950 Sq Ft
3 Somerset Ln, Edgartown, MA 02539

NEW CONSTRUCTION: LUXURY ISLAND LIVING AT SOMERSET.Construction is underway at Three Somerset Lane, the newest residence (and last to be offered) in this exclusive enclave of five luxury homes, perfectly positioned between Edgartown Village and South Beach. Developed by Stanmar, owners of the renowned Winnetu Oceanside Resort, Somerset embodies modern coastal design paired with timeless

Wendy Harman Compass | Point B

3 Somerset Ln, Edgartown, MA 02539
/60
$16,500,000
- 5 Beds
- 7.5 Baths
- 6,781 Sq Ft
3 Field Club Ln, Edgartown, MA 02539

An exquisite offering, also known as Sand Castle, in the highly coveted Field Club. Nestled within the luxury Field Club enclave, this sophisticated 5-bedroom, 7.5-bath residence embodies modern luxury with pristine coastal charm. Step into an expansive open living plan where refined millwork, soaring ceilings, and elegant finishes define each space. A gourmet chef’s kitchen features top-tier

Thomas Wallace Wallace & Co. Sotheby's

3 Field Club Ln, Edgartown, MA 02539
/48
$1,595,000
- 5 Beds
- 4 Baths
- 2,516 Sq Ft
651 State Rd, Vineyard Haven, MA 02568

***COMING SOON*** Showings start Friday 9/5.Fabulous multi-building compound offered in West Tisbury. Well maintained main house dating to 1880 has many features common to classic older homes but has been updated to provide comfort and year-round livability. Bright and cozy there are lots of rooms and spaces to provide for a larger group of individuals with a total of 4 bedrooms in the

Jim Feiner Feiner Real Estate

651 State Rd, Vineyard Haven, MA 02568
/28
$7,450,000
- 5 Beds
- 4.5 Baths
- 5,000 Sq Ft
7 Clay Pit Ln, Aquinnah, MA 02535

Stunning waterfront home with panoramic waterviews. The home was designed by Hutker Associates, built by Andrew Flake, and landscaped by Michael Van Valkenburgh - three of the most renowned names in Martha's Vineyard home creation. Little wonder it was featured on the cover of Beautiful Home magazine and has been included in several other home design magazines and books. The 5000 sq ft house

Mark Jenkins Wallace & Co. Sotheby's

7 Clay Pit Ln, Aquinnah, MA 02535
/46
$14,500,000
- 6 Beds
- 5 Baths
- 4,964 Sq Ft
825 Main St, Vineyard Haven, MA 02568

Set on 1.75 acres this waterfront home features 200+/- feet of sandy beach on the outer harbor in the community of West Chop. Upon entering the home, the stunning view of the outer harbor and Nantucket Sound is breathtakingly beautiful. Perfect for hosting large parties or intimate family gatherings the spacious living room spills onto the large deck through two sets of French doors. Gleaming

Judy Federowicz Landmarks at TODAY Real Estate

825 Main St, Vineyard Haven, MA 02568
/26
$8,650,000
- 4 Beds
- 6 Baths
- 3,497 Sq Ft
24 Katama Bay View Rd, Edgartown, MA 02539

This classic New England waterview home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room

Thomas Wallace Wallace & Co. Sotheby's International Realty

24 Katama Bay View Rd, Edgartown, MA 02539
/26
$2,150,000
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
8 Old Purchase Way, Edgartown, MA 02539

Private, yet close to town. Located at the end of a paved road on a cul-de-sac that abuts 25 acres of conservation land. Enjoy miles of walking/bike trails and ancient roads just out the door. The first floor has an open floor plan with comfortable living / dining area / kitchen areas. There is also a first-floor bedroom/office, new sun room and 1/2 bathroom. Upstairs, there is a large

Tjark Aldeborgh eXp Realty

8 Old Purchase Way, Edgartown, MA 02539
/76
$2,345,000
- 4 Beds
- 2 Baths
- 1,545 Sq Ft
15 Night Heron Rd, Edgartown, MA 02539

KATAMA - NEWLY RENOVATED! This Quintessential Martha’s Vineyard saltbox blends timeless island character with wonderful thoughtful updates, having been recently renovated. Set in a quiet location, Island Grove, one of the most popular locations in Edgartown, you're just a short drive to Wilson's Landing, South Beach and downtown Edgartown, an ideal location for summer escapes, year-round living,

Alisan Lohan-Conway Alisan Lohan-Conway Properties

15 Night Heron Rd, Edgartown, MA 02539
/44
$4,695,000
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
16 Frog Hollow, Vineyard Haven, MA 02568

Timeless Water View Home on Vineyard Haven Harbor. Nestled between historic Main Street and the exclusivity of West Chop, this property combines private coastal living with access to the best of Vineyard Haven. With access to the calm waters of the Harbor, the residence sits at the edge of a sweeping meadow with uninterrupted water views. Built in 2015 the three-bedroom, two-bathroom home is a

Rose Ryley Sandpiper Realty Inc

16 Frog Hollow, Vineyard Haven, MA 02568
/7
$700,000
- 3 Beds
- 1 Bath
- 1,168 Sq Ft
10 Putnam Way, Vineyard Haven, MA 02568

Raised ranch style house on a corner lot near the lagoon. This could be the ''fixer upper'' buyers always ask about. Location is in the Lagoon Pond watershed and BUYER will have to replace the septic system to bring up to latest environmental requirements.

Kathleen Dawson Donnelly + Co.

10 Putnam Way, Vineyard Haven, MA 02568
/42
$4,250,000
- 3 Beds
- 6 Baths
- 3,171 Sq Ft
15 Old Farm Rd, Chilmark, MA 02535

CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level

Tina Miller Donnelly + Co.

15 Old Farm Rd, Chilmark, MA 02535
/42
$1,825,000
- 4 Beds
- 2 Baths
- 1,342 Sq Ft
58 Road To the Plains, Edgartown, MA 02539

KATAMA BEACH HOUSE - This turnkey Katama retreat blends coastal charm with modern comfort, offering a rare combination of location, amenities, and style. A 19-foot heated swim spa with current, and beautiful wooden deck, lets you swim year-round or unwind in the attached Jacuzzi. The property comes fully furnished, making it an effortless purchase, and boasts a strong rental history for

Dawn Bellante Sandpiper Realty Inc

58 Road To the Plains, Edgartown, MA 02539
/30
$1,550,000
- 3 Beds
- 2.5 Baths
- 1,822 Sq Ft
1 Saddle Club Rd, Edgartown, MA 02539

Welcome to your perfect island retreat in the heart of Edgartown conveniently located in a quiet neighborhood off of Edgartown West Tisbury Road. This charming 3-bedroom, 2.5 bathroom home offers the ideal blend of comfort, and functionality. Nestled on a quiet street, the property features an oversized two-car garage--perfect for storing vehicles, bikes, and beach gear, or even setting up a

Madelyn Silvia Wallace & Co. Sotheby's International Realty

1 Saddle Club Rd, Edgartown, MA 02539
/47
$5,450,000
- 4 Beds
- 5.5 Baths
- 3,300 Sq Ft
8 Paddock Rd, Oak Bluffs, MA 02557

Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of a tranquil pond and surrounding grasslands, this beautiful residence offers a masterful blend of traditional coastal architecture and modern luxury. Located in the prestigious enclave of The Preserve, this sprawling home is designed for effortless elegance, privacy, and indoor-outdoor living.At the heart of

Lesley Heidt Sandpiper Realty Inc

8 Paddock Rd, Oak Bluffs, MA 02557
/78
$8,500,000
- 6 Beds
- 6.5 Baths
- 6,927 Sq Ft
6 Janes Cove Rd, Edgartown, MA 02539

Waterfront on Edgartown Great Pond, this newly-renovated Coastal Colonial is set on a very private 9.2 acre lot on Janes Cove. You know you are somewhere very special the moment you enter through the gates. As you travel along the cobblestone lined driveway flanked by lush lawns, the gorgeous home rises before you. Stunning the day it was originally completed, it has now been completely renovated

Mark Jenkins Wallace & Co. Sotheby's International Realty

6 Janes Cove Rd, Edgartown, MA 02539
/38
$4,995,000
- 7 Beds
- 4.5 Baths
- 5,982 Sq Ft
19 Locust Ln, Aquinnah, MA 02535

This beautifully designed and built home is privately sited on 4.02 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views, tall ceilings, a field stone fireplace and concrete floors heated by radiant heat. French doors take

Brenda Galligan Karen M. Overtoom R.E.

19 Locust Ln, Aquinnah, MA 02535
/15
$845,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60 -R Carol Ln, Oak Bluffs, MA 02557

Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

Sheila Morse Island Real Estate

60 -R Carol Ln, Oak Bluffs, MA 02557
/14
$845,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60R Carol Ln, Oak Bluffs, MA 02557

Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

Nora Jardin Island Real Estate

60R Carol Ln, Oak Bluffs, MA 02557
/42
$1,845,000 Open Fri 1:30PM - 2:30PM
- 3 Beds
- 3 Baths
- 1,389 Sq Ft
12 W Farm Rd, West Tisbury, MA 02575

Welcome to your dream home in the picturesque town of West Tisbury, nestled in the coveted Coffins Field neighborhood.This stunning home has undergone a total renovation, resulting in a fresh, modern, and inviting atmosphere. The home boasts an expansive layout with 3 bedrooms and 3 bathrooms and that includes a completely finished, unaccounted approximate 850 sqft walk-out basement. The

Joe & Nicole Holland Vineyard Dream Realty LLC

12 W Farm Rd, West Tisbury, MA 02575
/28
$1,325,000
- 3 Beds
- 2 Baths
- 1,764 Sq Ft
170 Barnes Rd, Oak Bluffs, MA 02557

Calling water and boating enthusiasts. Solid Cape-style home one block from Sailing Camp Park, water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back

Christine Rose Martha's Vineyard Island-Wide Realty

170 Barnes Rd, Oak Bluffs, MA 02557
/32
$2,250,000
- 4 Beds
- 2.5 Baths
- 2,522 Sq Ft
29 Old Nursery Ln, Chilmark, MA 02535

Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

Julianna Flanders Flanders Real Estate

29 Old Nursery Ln, Chilmark, MA 02535
/6
$900,000
- 1 Bed
- 1 Bath
- 534 Sq Ft
136 W Spring St, Vineyard Haven, MA 02568

136 Spring Street - Sited on 0.32 acres and just moments from the Tisbury School and downtown Vineyard Haven, this one bedroom, one bathroom home is serviced by a 4-bedroom septic system, allowing for immediate expansion.Note: This property is also being marketed as a compound with the abutting 4BR/2.5BA home at 128 Spring Street.

David Dickinson Compass | Point B

136 W Spring St, Vineyard Haven, MA 02568
/32
$1,600,000
- 5 Beds
- 3.5 Baths
- 2,436 Sq Ft
128 W Spring St, Vineyard Haven, MA 02568

128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to

David Dickinson Compass | Point B

128 W Spring St, Vineyard Haven, MA 02568
/48
$5,495,000
- 3 Beds
- 3.5 Baths
- 4,131 Sq Ft
36 Crocker Dr, Edgartown, MA 02539

Stunning Katama Retreat ~ Welcome to this newly constructed architectural gem, nestled on half an acre in the heart of Katama. Perfectly positioned just blocks from the Field Club, close to South Beach, the bike path, and Edgartown Village, this home offers the ultimate indoor-outdoor Martha's Vineyard lifestyle. The elegant entryway sets the tone, leading into a spectacular vaulted living room

Stephanie Roache Donnelly + Co.

36 Crocker Dr, Edgartown, MA 02539
/32
$1,725,000
- 3 Beds
- 2.5 Baths
- 1,914 Sq Ft
78 Whalers Walk, Edgartown, MA 02539

Nestled in a tranquil residential neighborhood, at the top of a curved drive through beautiful trees, this well-maintained home in move-in condition offers an idyllic Martha's Vineyard lifestyle. Custom-built for quality and convenience by a prestigious Island builder, every detail was thoughtfully planned for exclusive use by the family as a cherished year-round vacation home. The open floor

Dawn Bellante Sandpiper Realty Inc

78 Whalers Walk, Edgartown, MA 02539
/42
$3,995,000
- 3 Beds
- 4 Baths
- 3,426 Sq Ft
96 Hammett Ln, Chilmark, MA 02535

Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

Brenda Galligan Karen M. Overtoom R.E.

96 Hammett Ln, Chilmark, MA 02535
/44
$6,395,000
- 6 Beds
- 5.5 Baths
- 7,000 Sq Ft
400 Barnes Rd, Vineyard Haven, MA 02568

Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

Jennifer DaSilva Compass | Point B

400 Barnes Rd, Vineyard Haven, MA 02568
/41
$3,600,000
- 3 Beds
- 4 Baths
- 2,500 Sq Ft
27 Clambelly Rd, Chilmark, MA 02535

A place of serenity tucked in the woods of Chilmark. Complete renovation 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 flooring. LED lighting throughout house, Media

Julianna Flanders Flanders Real Estate

27 Clambelly Rd, Chilmark, MA 02535
/52
$3,750,000
- 5 Beds
- 6.5 Baths
- 4,372 Sq Ft
139 Main St, Vineyard Haven, MA 02568

Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses--now gracefully combined into a single half-acre parcel--this home offers rare space, privacy, and timeless character in one of the island's most approachable villages. From the moment you step through the welcoming

Leslie Floyd Portfolio Properties

139 Main St, Vineyard Haven, MA 02568
/26
$1,700,000
- 2 Beds
- 0.5 Baths
- 601 Sq Ft
108 Bay View Ave, Edgartown, MA 02539

Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

Derick Freitas Amaral & Associates Real Estate

108 Bay View Ave, Edgartown, MA 02539

Showing Results 41 - 80, Page 2 of 7

Massachusetts Dukes County

How to Buy a Home How to Finance a Home How to Sell a Home

Dukes County Types of Homes for Sale

More About Living in Dukes County

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage