Dukes County MA Homes for Sale

/42
$5,995,000
- 3 Beds
- 6 Baths
- 3,608 Sq Ft
385 Barnes Rd, Vineyard Haven, MA 02568

Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

Wendy Harman

Compass

(508) 205-8817

385 Barnes Rd, Vineyard Haven, MA 02568
/27
$1,649,000
- 3 Beds
- 2.5 Baths
- 1,740 Sq Ft
27 Chapde Ln, Tisbury, MA 02568

Classic Style Meets Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this residence provides a modern and spacious environment for comfortable island living. The home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that

Wendy Harman

Compass

(508) 691-8993

27 Chapde Ln, Tisbury, MA 02568
/42
$5,750,000
- 4 Beds
- 4.5 Baths
- 3,643 Sq Ft
4 Somerset Ln, Edgartown, MA 02539

New Construction: Reimagined Island Living At Somerset. Located in Katama, Somerset is an exclusive five-home luxury enclave perfectly located between Edgartown Village and South Beach -- and developed by Stanmar, owners of the Winnetu Oceanside Resort. The home sites have been designed to maximize outdoor living and entertaining around a spacious and private yard with expansive lawns and room

Wendy Harman

Compass

(508) 715-9594

4 Somerset Ln, Edgartown, MA 02539
/32
$985,000
- 2 Beds
- 1 Bath
- 990 Sq Ft
37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 514-5238

37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
/24
$935,000
- 1 Bed
- 1 Bath
- 797 Sq Ft
37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood

Lisa Lucier

Anchor Realty of MV

(508) 422-4131

37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
/26
$2,795,000
- 3 Beds
- 3 Baths
- 2,750 Sq Ft
109 Herring Creek Rd, Edgartown, MA 02539

Coastal Retreat In Katama - Located in the heart of Katama, with the iconic Katama Airfield and the sandy shores of South Beach nearby, this contemporary coastal retreat is ideal for enjoying all the best of Katama. The reverse-style contemporary features a sunny, open-designed floor plan with vaulted ceilings that seamlessly combine an inviting Living Room with gas fireplace, a Game Room with

Wendy Harman

Compass

(508) 274-5363

109 Herring Creek Rd, Edgartown, MA 02539
/34
$2,500,000
- 6 Beds
- 2.5 Baths
- 1,666 Sq Ft
34 Massasoit Ave, Oak Bluffs, MA 02568

This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to

Lisa Lucier

Anchor Realty of MV

(508) 348-7972

34 Massasoit Ave, Oak Bluffs, MA 02568
/27
$1,200,000
- 2 Beds
- 2.5 Baths
- 1,500 Sq Ft
70 Carol Ln, Oak Bluffs, MA 02557

Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot this ranch home with a finished basement has been recently renovated. The first floor has 1500 sq feet with of a large open kitchen, dining area, and living room with plenty of room for large gatherings. The primary bedroom has a bathroom on suite. Another bedroom has easy access to the hall bath. The

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 456-5742

70 Carol Ln, Oak Bluffs, MA 02557
/4
$6,295,000
- Land
- 0.5 Acre
- $12,590,000 per Acre
3 Somerset Ln, Edgartown, MA 02539

COMING SOON: LUXURY ISLAND LIVING AT SOMERSET - Construction is underway at Three Somerset Lane, part of an exclusive enclave of five luxury homes between Edgartown Village and South Beach. Developed by Stanmar, owner of Winnetu Resorts, Somerset blends modern coastal design with island charm. Designed by Dudley Cannada and built by Adam Moran Construction, this 4-bedroom, 5.5-bath home offers

Wendy Harman

Compass

(508) 419-9057

3 Somerset Ln, Edgartown, MA 02539
/42
$3,495,000
- 3 Beds
- 3.5 Baths
- 3,056 Sq Ft
9 Thaxter Ln, Edgartown, MA 02539

Contemporary coastal retreat near South Beach. Just moments from the ocean, this tri-level home on Thaxter Lane offers modern design, indoor-outdoor living, and a saltwater pool. Hear ocean sounds from your deck and enjoy Edgartown living—ideal as a private escape or rental property. The light-filled living room has vaulted ceilings, a wood-burning fireplace, and sliding doors opening to

Wendy Harman

Compass

(508) 274-5363

9 Thaxter Ln, Edgartown, MA 02539
/22
$1,250,000
- 2 Beds
- 1 Bath
- 742 Sq Ft
47 Winemack St, Oak Bluffs, MA 02557

Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

Lisa Lucier

Anchor Realty of MV

(508) 403-9601

47 Winemack St, Oak Bluffs, MA 02557
/21
$1,650,000
- 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

(508) 715-6242

9 Brunswick Ave, Oak Bluffs, MA 02557
/42
$3,395,000
- 3 Beds
- 3.5 Baths
- 2,527 Sq Ft
5 Katama Dr, Edgartown, MA 02539

Modern Coastal Retreat In Katama: Freshly reimagined and impeccably styled, this modern coastal residence in the heart of Katama offers a rare opportunity to own a newly renovated home just one mile from South Beach. This appealing retreat has been elevated with curated finishes, high-end systems, and a designer-selected furnishing package that perfectly embodies the relaxed luxury of Vineyard

Wendy Harman

Compass

(508) 546-9869

5 Katama Dr, Edgartown, MA 02539
/23
$8,995,000
- 11 Beds
- 8.5 Baths
- 6,289 Sq Ft
1 Louis Field Rd, Edgartown, MA 02539

SWEETENED WATER FARM ESTATE. Located just one mile from the heart of historic Edgartown Village, this compound in Sweetened Water Farm presents a rare opportunity to become the next steward of this extraordinary Martha’s Vineyard estate. Privately sited on 4.6 acres of exquisitely cultivated gardens, this remarkable property has been featured in several publications celebrating the island’s most

Wendy Harman

Compass

(508) 715-8610

1 Louis Field Rd, Edgartown, MA 02539
/41
$9,495,000
- 4 Beds
- 6 Baths
- 4,605 Sq Ft
29 Slough Cove Rd, Edgartown, MA 02539

LUXURIOUS COUNTRY ESTATE IN KATAMA. Sited at the end of a long private drive, amid a bucolic 1.5-acre meadow setting with stone retaining walls and lush perennial gardens, this elegant country estate, designed by noted architect Patrick Ahearn, offers the epitome of luxurious living in Katama. The home’s timeless and charming character is highlighted by thoughtful, top-notch architectural details

Wendy Harman

Compass

(508) 691-8146

29 Slough Cove Rd, Edgartown, MA 02539
/37
$9,995,000
- 6 Beds
- 7.5 Baths
- 7,205 Sq Ft
25 Lelands Path, Edgartown, MA 02539

Casual Elegance On Katama Bay - Welcome to 25 Leland’s Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappquiddick. This magnificent home offers over 7,200 square feet of living space, six bedrooms, all with en suite baths, and a three-room Owner's Suite with sweeping water views and a private second-floor deck. The

Wendy Harman

Compass

(508) 625-9706

25 Lelands Path, Edgartown, MA 02539
/68
$4,175,000
- 6 Beds
- 3.5 Baths
- 3,397 Sq Ft
19 Kitts Field Cir, Edgartown, MA 02539

Old World Vineyard Charm Meets Modern Katama Living. Welcome to this beautifully crafted Katama family compound, a private, thoughtfully designed estate offering timeless elegance and exceptional amenities. Nestled near Edgartown Village, this stunning property includes a four-bedroom main residence with three levels of living space, a charming two-bedroom guest house, pool house, pool, spa,

Michele Casavant Vineyard Village Realty

19 Kitts Field Cir, Edgartown, MA 02539
/29
$2,695,000
- 4 Beds
- 3 Baths
- 2,001 Sq Ft
2 Orchard Ln, Edgartown, MA 02539

EDGARTOWN GEM: WALK TO TOWN + RELAX BY THE POOL. Nestled just a short stroll from all the best of Edgartown Village, this beautifully renovated retreat offers the ideal balance of Vineyard charm and modern convenience. Designed across three levels of living spaces, the home provides a flexible layout that works beautifully for entertaining, relaxing, or hosting guests.The main floor

Wendy Harman Compass | Point B

2 Orchard Ln, Edgartown, MA 02539
/17
$2,500,000
- 3 Beds
- 2.5 Baths
- 1,984 Sq Ft
19 Katama Dr, Edgartown, MA 02539

Just over a mile from South Beach, this inviting Katama retreat is a perfect getaway. This sunlit home and detached living space offer three bedrooms and three baths, providing plenty of room for everyone. Set on a landscaped 3⁄4-acre lot with pastoral views and peeks of the Ocean from the upper-level deck, the property features a wraparound deck for barbecues and a spacious backyard for games or

Emma Kennedy Sandpiper Realty

19 Katama Dr, Edgartown, MA 02539
/24
$4,695,000
- 5 Beds
- 2.5 Baths
- 3,885 Sq Ft
18 Homeward Way, Chilmark, MA 02535

Welcome to 18 Homeward Way — a peaceful Chilmark retreat tucked off scenic North Road, just minutes from the storied fishing village of Menemsha. This rare 15-acre offering includes two buildable parcels, creating an extraordinary opportunity for a Vineyard compound.The impeccably maintained residence, built in 1986, radiates classic Vineyard charm. Its thoughtful single-level layout

Bill Rossi Studio Realty

18 Homeward Way, Chilmark, MA 02535
/39
$2,700,000
- 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

Doug Burke Cronigs Real Estate

229 Oak Ln, West Tisbury, MA 02575
/36
$4,695,000
- 5 Beds
- 5.5 Baths
- 4,003 Sq Ft
97 Longview Rd, Vineyard Haven, MA 02568

This beautifully designed post-and-beam home features stunning views of the Vineyard Sound, Elizabeth Islands, and unforgettable sunsets. Surrounded by beautiful stone walls, sited on 2.2 acres, this serene property offers luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels with generous decks ideal for outdoor living and entertaining. The upper

Stephanie Roache Donnelly + Co.

97 Longview Rd, Vineyard Haven, MA 02568
/39
$2,700,000
- 6 Beds
- 3.5 Baths
- 3,000 Sq Ft
63 Crowell Ln, Vineyard Haven, MA 02568

Extraordinary West Chop Opportunity - Two Homes on 1.80 Acres in Vineyard HavenNestled next to the desirable West Chop/Mink Meadows neighborhoods, this unique property is less than two miles from the center of town and the beach. The property features two dwellings, making it a perfect opportunity for multi-generational living, guest accommodations, or rental potential.The welcoming,

Heather Dyas-Fried Tea Lane Associates

63 Crowell Ln, Vineyard Haven, MA 02568
/45
$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

Katherine Donahue Sandpiper Realty Inc

76 Washque Ave, Edgartown, MA 02539
/34
$3,450,000
- 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
/63
$4,295,000
- 7 Beds
- 6 Baths
- 9,686 Sq Ft
56 N Neck Rd, Edgartown, MA 02539

A RARE CHAPPAQUIDDICK LEGACY ESTATE — Privacy & Island Living at its finest.Step into a world where time slows, ocean breezes carry the scent of salt and cedar, and each day begins and ends with the relaxing sounds of the local fauna and the Vineyard Sound. This 18.4-acre multi-residence estate, with 4 conforming parcels, on Martha’s Vineyard’s treasured Chappaquiddick Island is more than a

Leslie C. Floyd Portfolio Real Estate, Inc.

56 N Neck Rd, Edgartown, MA 02539
/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
/51
$2,750,000
- 5 Beds
- 4.5 Baths
- 4,982 Sq Ft
79 David Ave, Vineyard Haven, MA 02568

BEAUTIFUL CUSTOM-BUILT RETREAT- LAMBERT'S COVE This impressive property offers the perfect blend of privacy and convenient access to downtown and the picturesque James Pond Reserve at Lambert's Cove Beach. Step inside to discover over 4,900 sq ft of recently renovated living space. The home boasts 5 bedrooms and 4.5 bathrooms, including a stunning chef's kitchen that will ignite your culinary

Tina Miller Donnelly + Co

79 David Ave, Vineyard Haven, MA 02568
/42
$2,750,000
- 5 Beds
- 4.5 Baths
- 4,982 Sq Ft
79 David Ave, Vineyard Haven, MA 02568

BEAUTIFUL CUSTOM-BUILT RETREAT – LAMBERT’S COVE This impressive 4,900+ sq ft home offers privacy with easy access to downtown and James Pond Reserve at Lambert’s Cove Beach. Featuring 5 bedrooms, 4.5 baths, and a stunning chef’s kitchen, perfect after trips to local farm stands. Enjoy multiple living areas—oversized family/media room, dining room, sunny living room, and game room. Outdoor

Tina Miller Donnelly + Co.

79 David Ave, Vineyard Haven, MA 02568
/39
$3,200,000
- 3 Beds
- 3.5 Baths
- 2,268 Sq Ft
23 Thaxter Ln, Edgartown, MA 02539

OPEN AND AIRY COASTAL RETREAT WITH EASY ACCESS TO SOUTH BEACH and EDGARTOWN VILLAGE. Welcome to this tri-level contemporary home in the heart of KATAMA. This home offers the perfect blend of spacious indoor-outdoor living with three levels of outdoor decking nestled amongst mature vegetation and a quick stroll to South Beach. The home features vaulted ceilings, two first floor bedroom

Michele Casavant Vineyard Village Realty

23 Thaxter Ln, Edgartown, MA 02539
/45
$2,895,000
- 3 Beds
- 3.5 Baths
- 2,898 Sq Ft
4 Pip'N Rd, Edgartown, MA 02539

Chappaquiddick charm meets Edgartown elegance at this meticulously maintained property. No detail has been overlooked in this spacious custom home. The foyer entry greets you with a sizable dining room to your right which flows into an open eat in kitchen with a built in banquet, a granite kitchen island overlooking the masonry fireplace and wall of glass sliders in the living room. A wet bar

Michele Casavant Vineyard Village Realty

4 Pip'N Rd, Edgartown, MA 02539
/81
$2,998,000
- 3 Beds
- 2 Baths
- 2,558 Sq Ft
12 Duarte Cir, Edgartown, MA 02539

Nestled in the coveted Katama neighborhood of Edgartown, this stylish 3-bedroom, 2-bathroom contemporary home offers a perfect blend of comfort, location, and opportunity. Designed with an open and airy layout, the home features vaulted ceilings, abundant natural light, and a seamless connection to the outdoor living spaces. Set on a generous lot, the property presents a variety of expansion

Jessie Holtham Wallace & Co. Sotheby's

12 Duarte Cir, Edgartown, MA 02539
/30
$2,750,000
- 3 Beds
- 4 Baths
- 2,830 Sq Ft
42 Deacon Vincent Way, Edgartown, MA 02539

Katama ~ Turnkey Retreat in Edgartown Estates. Located on a quiet, paved road in sought-after Edgartown Estates, this meticulously maintained home offers the perfect blend of privacy, space, and convenience. Ideally positioned equidistant to South Beach and downtown Edgartown, and just moments from the bike path, it’s an ideal Vineyard getaway or year-round residence. Thoughtfully designed for

Stephanie Roache Donnelly + Co

42 Deacon Vincent Way, Edgartown, MA 02539
/19
$2,675,000
- 3 Beds
- 1.5 Baths
- 1,540 Sq Ft
5 Ocean View Farm Rd, Chilmark, MA 02535

Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

Natalie Conroy Conroy & Company R.E., Inc.

5 Ocean View Farm Rd, Chilmark, MA 02535
/47
$2,450,000
- 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
/42
$2,450,000
- 6 Beds
- 4.5 Baths
- 2,970 Sq Ft
128 W 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 create a flexible compound just moments from downtown Vineyard Haven. The 4-bedroom, 2-1/2 bath main house also includes a separate, 1-bedroom in-law/nanny apartment with a full bath. The guest house has 1 bedroom and 1 bath, with a 4-bedroom septic system allowing

David Dickinson Compass

128 W Spring St, Vineyard Haven, MA 02568
/36
$3,250,000
- 4 Beds
- 3.5 Baths
- 2,515 Sq Ft
300 North Rd, Chilmark, MA 02535

Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

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

300 North Rd, Chilmark, MA 02535
/36
$2,500,000
- 4 Beds
- 3 Baths
- 2,350 Sq Ft
16 South Rd, Chilmark, MA 02535

Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been

Michele Casavant Vineyard Village Realty

16 South Rd, Chilmark, MA 02535
/32
$2,950,000
- 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
/41
$3,200,000 Open House 10/11
- 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

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