Dukes County MA Homes for Sale

/26
$8,500,000
- 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

Tom Wallace Wallace & Co. Sotheby's International Realty

24 Katama Bay View Rd, Edgartown, MA 02539
/39
$2,600,000
- 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
/25
$1,895,000
- 4 Beds
- 2.5 Baths
- 2,064 Sq Ft
99 Old Purchase Rd, Edgartown, MA 02539

Welcome to this charming post and beam-style home, privately located at the end of a cul-de-sac on .71 acres with proximity to over 50 acres of Land Bank and Sheriff's Meadow land with multiple trails and paths. Conveniently located to the bike path, Morning Glory Farm, the heart of Edgartown, and Meetinghouse Way, with direct access to South Beach, the location is ideal. The floor plan was

Stephanie Roache Donnelly + Co

99 Old Purchase Rd, Edgartown, MA 02539
/51
$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
/20
$1,300,000
- 4 Beds
- 2 Baths
- 1,566 Sq Ft
344 Greenwood Ave, Vineyard Haven, MA 02568

This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles

Katie Donahue Sandpiper Realty

344 Greenwood Ave, Vineyard Haven, MA 02568
/41
$8,900,000 Pre-Foreclosure
- 8 Beds
- 9 Baths
- 8,560 Sq Ft
150 E Chop Dr, Oak Bluffs, MA 02557

Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast

Moira Lown Coldwell Banker Realty - Wellesley

150 E Chop Dr, Oak Bluffs, MA 02557
/26
$1,595,000
- 5 Beds
- 3 Baths
- 1,810 Sq Ft
22 Old Lighthouse Rd, Vineyard Haven, MA 02568

This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a 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

Jessie Holtham Wallace & Co. Sotheby's

22 Old Lighthouse Rd, Vineyard Haven, MA 02568
/30
$985,000
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
22 Clark Ave, Vineyard Haven, MA 02568

A Sweet Spot to call Home. West Chop charms are many in this delightful setting. Acres upon acres of nearby conservation trails make walks, hikes and bike rides an easy daily appeal. Equal distance to Owen Little Way town beach and Vineyard Haven Main Street shops and amenities as well as harbor and ferry port. This move-in ready Clark Avenue abode offers the magic formula of single level living

Helena Kirschenbaum Studio Realty

22 Clark Ave, Vineyard Haven, MA 02568
/47
$2,375,000
- 6 Beds
- 4.5 Baths
- 2,970 Sq Ft
128 & 136 Spring St, Vineyard Haven, MA 02568

A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street—two adjacent properties being sold together to create a unique, flexible compound just moments from the Tisbury School and downtown Vineyard Haven. With a spacious main residence and a separate guest house, this rare combination presents a compelling opportunity for multigenerational living, seasonal enjoyment,

David Dickinson Compass | Point B

128 & 136 Spring St, Vineyard Haven, MA 02568
/46
$1,345,000
- 3 Beds
- 2 Baths
- 1,862 Sq Ft
249 State Rd, Vineyard Haven, MA 02568

PRICE REDUCED $150,000!! LARGE LOT ALLOWS ADDITIONAL STRUCTURE perfect for art gallery, business office, studio, etc. Possibilities are endless! WALK TO TOWN, FERRY AND BEAUTIFULLY FURNISHED! This beautifully restored 3-bedroom, 2-bath home has touches from the old Vineyard—a sun porch for napping or reading, a large yard with magnificant magnolia tree, and a detached garage for your Island car.

Barbara Twiss Laer Realty Partners

249 State Rd, Vineyard Haven, MA 02568
/16
$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. There are so many outstanding possibilities for a future Buyer to build their dream home on this

Elissa Lash Tea Lane Associates

37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
/52
$4,900,000
- 5 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 gorgeous four bedroom gambrel home offers comfort and ease of coastal luxurious living. The primary home welcomes you with a two story foyer which opens to a large great room with a gourmet kitchen, with a bar area and a central island offering seating for at least four. The

Michele Casavant Vineyard Village Realty

23 Pinehurst Rd, Edgartown, MA 02539
/46
$1,299,000
- 3 Beds
- 3 Baths
- 1,750 Sq Ft
185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

Experience sun-drenched living in one of Tashmoo Woods’ most desirable floor plans. This beautifully maintained 3-bedroom, 3-bath home offers full access to the coveted Tashmoo Woods amenities, including a pristine pool and pool house, multiple tennis courts, a children’s play area, a private launch on Lake Tashmoo, and a beautiful Association beach on the Sound. Inside, soaring ceilings and

Candy DaRosa Feiner Real Estate

185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
/15
$2,490,000
- Land
- 7.08 Acres
- $351,695 per Acre
2 Jacob's Neck Rd Unit 2, Edgartown, MA 02539

Build your dream home or homes on the special 7.1 acre private wooded property surrounding a 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 convenient to

Robert Kenney Tea Lane Associates

2 Jacob's Neck Rd Unit 2, Edgartown, MA 02539
/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
/32
$2,750,000
- 4 Beds
- 3.5 Baths
- 2,566 Sq Ft
28 Marthas Rd, Edgartown, MA 02539

Nestled on a generous corner lot in one of Edgartown’s sought-after neighborhoods, this beautifully maintained 4BD, 3.5BA home offers the perfect blend of comfort, convenience, and classic Vineyard charm. The home features a spacious and versatile floor plan, ideal for both year-round living and summer getaways. The light-filled living areas, anchored by a floor to ceiling wood burning fireplace,

Stacy Ickes Donnelly + Co.

28 Marthas Rd, Edgartown, MA 02539
/6
$1,795,000
- Land
- 1.87 Acres
- $961,435 per Acre
22 Paddock Rd Unit 85, Oak Bluffs, MA 02568

THE PRESERVE at THE WOODLANDS ~ OAK BLUFFS COVETED COMMUNITY of architecturally designed residences. Live in ONE of the most sought-after locations in Oak Bluffs that is conveniently located to town, beaches, harbor, ferry ports, and Farm Neck Golf & Tennis Club. This is a RARE OFFERING to purchase one of the last remaining building lots and develop a family compound. There are underground

Marilyn Moses Ocean Park Realty Inc

22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
/134
$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
/4
$675,000
- Land
- 0.23 Acre
- $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
$350,000
- Land
- 1.26 Acres
- $277,778 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 and a picturesque stretch of shoreline perfect for

Alyssa Halisky Wallace & Co. Sotheby's

0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535
/32
$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
/21
$1,395,000
- 3 Beds
- 1 Bath
- 1,033 Sq Ft
9 Brunswick Ave, Oak Bluffs, MA 02557

PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! 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

Alice Pierce Coldwell Banker Realty - Hingham

9 Brunswick Ave, Oak Bluffs, MA 02557
/11
$619,000
- Land
- 0.61 Acre
- $1,018,930 per Acre
147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568

Vacant lot - NO LIMIT on bedroom count! You just have to meet setbacks. Once you build your dream home, you will able to explore nature just steps away. Nearby there are two Lagoon access points for kayaking and swimming, as well as walking trails within the Martha's Vineyard Land Bank and Sheriff's Meadow properties. Enjoy the peace of a rural setting, yet remain conveniently close to the ferry

Idalyn Macchia Gilstad Wallace & Co. Sotheby's

147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568
/76
$2,195,000
- 4 Beds
- 2 Baths
- 1,344 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
/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
/17
$1,250,000
- Land
- 5.7 Acres
- $219,298 per Acre
14 Ridge Rd Unit 94, Aquinnah, MA 02535

Idyllic gently rolling parcel of mixed hardwoods, meadow and stone walls awaits your vision. A large level building envelope has been cleared. A house and an ADU are permitted by right and a barn(subject to town approval) will fit nicely on this secluded parcel with room for a horse to graze and access nearby Land Bank and Sheriffs Meadow conservation land .It is walking distance to Menemsha

Jim Wallen Feiner Real Estate

14 Ridge Rd Unit 94, Aquinnah, MA 02535
/11
$495,000
- Land
- 0.23 Acre
- $2,152,174 per Acre
0 Barnes Rd Unit 59 42701, Oak Bluffs, MA 02557

Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residence. Whether you envision a cozy cottage, a modern retreat, or a traditional island dwelling, the

Alyssa Halisky Wallace & Co. Sotheby's

0 Barnes Rd Unit 59 42701, Oak Bluffs, MA 02557
/32
$2,095,000
- 4 Beds
- 2.5 Baths
- 2,706 Sq Ft
35 Mariners Way, Edgartown, MA 02539

35 Mariner’s Way is sited on nearly a half acre lot and lies within walking distance to Edgartown Village shops, restaurants, galleries, and inns and Sheriff’s Meadow conservation land. This 4 bedroom, 2 1⁄2 bath home features a large living room and formal dining room, chef’s kitchen with two ovens and wine room/pantry, and a spacious family room with a gas fireplace. There are two ensuite

Russell Maloney Russell Maloney Real Estate

35 Mariners Way, Edgartown, MA 02539
/26
$2,195,000
- 3 Beds
- 3.5 Baths
- 2,453 Sq Ft
34 Davis St, Tisbury, MA 02568

NEW CONSTRUCTION - Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island's harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

Andrew McElhinney Compass Massachusetts, LLC

34 Davis St, Tisbury, MA 02568
/18
$1,045,000
- 3 Beds
- 2 Baths
- 1,469 Sq Ft
12 Park Ave, Vineyard Haven, MA 02568

Welcome to this delightful Cape-style home offering easy access to Vineyard Haven shopping and the Island's bike paths. Nestled on just under an acre of land, this inviting residence features three spacious bedrooms and two full bathrooms, providing ample space for year-round living or weekend getaways. Inside, you'll find a warm and welcoming open concept, perfect for both relaxing and

Sheila Morse Island Real Estate

12 Park Ave, Vineyard Haven, MA 02568
/16
$389,000
- Land
- 0.17 Acre
- $2,316,855 per Acre
00 Moshup Trail Unit 6, Aquinnah, MA 02535

Private Atlantic Ocean beach lot located on the serene coastline of Aquinnah on Martha's Vineyard. This exceptional beach lot offers a rare opportunity to own a piece of prime oceanfront. Located just off of Moshup Trail is private gated access to your own designated parking area. From there, a picturesque boardwalk meanders through native flora and opens onto a sandy path leading directly to

Alyssa Halisky Wallace & Co. Sotheby's

00 Moshup Trail Unit 6, Aquinnah, MA 02535
/32
$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 COURT that doubles into TWO PICKLE BALL COURTS, and a BASKETBALL

Michele Casavant Vineyard Village Realty

72 Chappaquiddick Ave, Edgartown, MA 02539
/15
$799,000
- 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
/12
$1,495,000
- 1 Bed
- 1 Bath
- 731 Sq Ft
47 E Chop Dr Unit 1, Oak Bluffs, MA 02568

East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condominium, ''Oak Bluffs'', features outstanding water views of the harbor and sound beyond. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch

Perry Patterson MV Luxury Homes, LLC

47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
/52
$1,675,000
- 2 Beds
- 2.5 Baths
- 2,000 Sq Ft
7 Meetinghouse Village Way, Edgartown, MA 02539

Experience refined coastal living in this impeccably renovated 2022 modern condominium nestled within the tranquil enclave of Meetinghouse Village. This sophisticated end-unit residence lives with the ease of new construction, offering bright, sun-washed interiors and an elevated design sensibility throughout.Every detail has been meticulously upgraded — from the all-new appliances, lighting,

Paul Pertile The Agency

7 Meetinghouse Village Way, Edgartown, MA 02539
/38
$1,825,000
- 4 Beds
- 3 Baths
- 3,142 Sq Ft
7 S Meadow Ln, Oak Bluffs, MA 02557

Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs' most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting. A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the

Katherine Donahue Sandpiper Realty Inc

7 S Meadow Ln, Oak Bluffs, MA 02557
/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
/3
$375,000
- Land
- 0.2 Acre
- $1,875,000 per Acre
00 Moshup Trail Unit 7-5, Aquinnah, MA 02535

Spectacular, private beach lot located just off Moshup Trail. Gated entry, parking rights and a deeded 1/5 acre of beach on the Atlantic. This is not a buildable lot, no structures of any kind are permitted. Map 10, Lot 7-5

Russell Maloney Russell Maloney Real Estate

00 Moshup Trail Unit 7-5, Aquinnah, MA 02535
/4
$445,000
- Land
- 0.56 Acre
- $794,643 per Acre
5 Candle Maker Cir Unit 1.331, 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

5 Candle Maker Cir Unit 1.331, 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

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