Dukes County MA Houses for Sale

/26
$2,000,000
- 3 Beds
- 2.5 Baths
- 1,784 Sq Ft
12 Lobsterville Rd, Aquinnah, MA 02535

12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short bike ride to the

Tina Palmer Conroy & Company R.E., Inc.

12 Lobsterville Rd, Aquinnah, MA 02535
/49
$6,490,000
- 6 Beds
- 8 Baths
- 5,660 Sq Ft
60 Meetinghouse Rd, Chilmark, MA 02535

This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

Jim Feiner Feiner Real Estate

60 Meetinghouse Rd, Chilmark, MA 02535
/39
$3,745,000
- 5 Beds
- 3 Baths
- 2,791 Sq Ft
20 James Pond Way, Vineyard Haven, MA 02568

Nestled on a serene 4.5-acre parcel of land off Lambert's Cove Road, this exquisite property offers unparalleled privacy, views and direct access to James Pond and beyond to the Land Bank's Lambert's Cove Beach property. In addition to the custom heated Gunite pool, the expansive yard provides space for many outdoor activities while relishing the tranquility of the location. The residence

Sheila Morse Island Real Estate

20 James Pond Way, Vineyard Haven, MA 02568
/21
$1,795,000
- 3 Beds
- 3.5 Baths
- 2,312 Sq Ft
7 Candlemaker Cir, Edgartown, MA 02539

3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

Roy Cutrer Jr Laer Realty Partners

7 Candlemaker Cir, Edgartown, MA 02539
/3
$1,795,000
- 3 Beds
- 3.5 Baths
- 2,311 Sq Ft
7 Candle Maker Cir, Edgartown, MA 02539

3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

Roy Cutrer LAER Realty Partners

7 Candle Maker Cir, Edgartown, MA 02539
/29
$6,795,000
- 3 Beds
- 2.5 Baths
- 2,589 Sq Ft
57 Hines Point Rd, Vineyard Haven, MA 02568

Lily Hill - a rare Hines Point offering that includes a waterfront home with exquisite views, a deep water mooring and dock, and 130 feet of private fine-sand beach. Poised on a knoll on the western shore of the Lagoon, Lily Hill evokes a more peaceful time with sweeping views of the sky and water. Enjoy a swim at your private beach morning, noon or night. Watch the play of light across the water

Elissa Lash Tea Lane Associates

57 Hines Point Rd, Vineyard Haven, MA 02568
/52
$3,975,000
- 4 Beds
- 3 Baths
- 2,704 Sq Ft
370 Lighthouse Rd, Aquinnah, MA 02535

Stunning waterview living with an active view that will never disappoint. Wake up every morning to breathtaking 180 degree water views in this beautifully appointed 4-bedroom, 3-bath coastal retreat. Perfectly situated to capture sunrise to sunset vistas, this home offers a blend of summer vibes with year-round living amenities. Step inside to find an open-concept living space filled with natural

Jill Napior Tea Lane Associates

370 Lighthouse Rd, Aquinnah, MA 02535
/15
$1,149,000
- 3 Beds
- 2 Baths
- 1,596 Sq Ft
96 Manchester Ave, Oak Bluffs, MA 02557

Nestled in a quiet neighborhood less than two miles from the heart of Circuit Avenue, this contemporary cape-style home is ready to welcome you. A charming farmer's porch invites you into a spacious living area with cathedral ceilings and an open-concept design that seamlessly connects the kitchen, dining, and living spaces--perfect for gathering with family and friends. The main level features a

Michele Moore Island Real Estate

96 Manchester Ave, Oak Bluffs, MA 02557
/30
$1,875,000
- 4 Beds
- 2 Baths
- 1,750 Sq Ft
16 Schoolhouse Rd, Edgartown, MA 02539

Vacation Getaway in Edgartown Estates - This sunny and welcoming contemporary home could be yours this summer! With an open layout, vaulted ceilings, and lots of windows and glass doors, the home feels bright and airy. Step outside to a spacious wrap-around deck--great for relaxing or entertaining. Inside, the living, dining, and kitchen areas flow nicely and are just the right size for

Lesley Heidt Sandpiper Realty Inc

16 Schoolhouse Rd, Edgartown, MA 02539
/35
$13,000,000
- 5 Beds
- 4.5 Baths
- 3,758 Sq Ft
6 Wakeman Rd, Chilmark, MA 02535

A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The

Julianna Flanders Flanders Real Estate

6 Wakeman Rd, Chilmark, MA 02535
/25
$3,600,000
- 3 Beds
- 3 Baths
- 4,382 Sq Ft
88 & 90 Quenames Rd, Chilmark, MA 02535

Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

Julianna Flanders Flanders Real Estate

88 & 90 Quenames Rd, Chilmark, MA 02535
/40
$5,295,000
- 7 Beds
- 4.5 Baths
- 5,320 Sq Ft
8 Fresh Pond Rd, Oak Bluffs, MA 02557

The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

Jarrett Hurwitz Keller Williams Realty

8 Fresh Pond Rd, Oak Bluffs, MA 02557
/44
$3,713,000
- 4 Beds
- 3 Baths
- 3,159 Sq Ft
3 Down Harbor Rd, Edgartown, MA 02539

Exceptional Opportunity in Down Harbor.Here’s a rare chance to own a property in Edgartown’s exclusive Down Harbor community. Known for its serene setting and prime access to Katama Bay, this neighborhood offers more than just scenic beauty— Ownership includes deeded rights to a pristine, sandy association beach, along with coveted mooring and dock privileges on Katama Bay — a benefit

Susan Wallo Compass | The O'Hanlon Group

3 Down Harbor Rd, Edgartown, MA 02539
/3
$925,000
- 2 Beds
90 17th St N, Edgartown, MA 02539

90 Seventeenth Street NorthEdgartown, MassachusettsFOR SALEHere is a chance for you to own a water view property in Edgartown. Property is located just off the Boulevard on a quiet dead end lane. This property has been in the same family for decades and is now offered for sale. It is a blank canvas for you to create your dream home. Interior has been gutted and is ready for your renovation. The

Theodore Saulnier TAS Real Estate, LLC

90 17th St N, Edgartown, MA 02539
/34
$4,350,000
- 3 Beds
- 2 Baths
- 1,260 Sq Ft
131 State Rd, Chilmark, MA 02535

Magical waterfront Quitsa pond cottage with private dock. This home has the most spectacular views including sunsets and an intimate relationship with the charming and timeless waterfront at Quitsa Pond. Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller home. Landscape design by Edwina von Gal accentuates

Jim Feiner Feiner Real Estate

131 State Rd, Chilmark, MA 02535
/46
$1,800,000
- 4 Beds
- 2.5 Baths
- 2,127 Sq Ft
5 Bayes Hill Cir, Vineyard Haven, MA 02568

Beautiful Bayes Hill Association! This nicely maintained 4 bedroom colonial-style home, located on a quiet cul-de-sac, is the perfect blend of comfort and charm. A new Red Cedar Shingle Roof, a newer high-efficiency furnace, newer state-of-the-art 75-gallon hot water heater, central air conditioning, 2 car garage and a freshly painted exterior this residence combines modern conveniences with

Rene Jackson Island Real Estate

5 Bayes Hill Cir, Vineyard Haven, MA 02568
/28
$1,590,000
- 4 Beds
- 1.5 Baths
- 1,592 Sq Ft
5 Scottys Ln, Vineyard Haven, MA 02568

NEWLY PRICED WELL BELOW TOWN ASSESSMENT! Attention Developers and Island Lovers! Take note of this rare opportunity in a prime West Tisbury Location priced. This mid-century home with excellent bones fronts on Seth's Pond, a beloved locale perfect for swimming, paddle-boarding, and kayaking. 5 Scotty's Lane has an existing 4-bedroom main house with the first floor and lower walk-out level

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

5 Scottys Ln, Vineyard Haven, MA 02568
/34
$1,599,000
- 5 Beds
- 2 Baths
- 1,440 Sq Ft
393 Lighthouse Rd, Aquinnah, MA 02535

Ranch style home & Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Living/Dining as well as the wrap-around deck. Enjoy the open concept main living area, two bedrooms,

Julianna Flanders Flanders Real Estate

393 Lighthouse Rd, Aquinnah, MA 02535
/27
$1,795,000
- 3 Beds
- 2.5 Baths
- 2,236 Sq Ft
71 6th St N, Edgartown, MA 02539

Classic three-bedroom farmhouse offers the perfect blend of island charm and laid-back comfort. Located within walking distance to scenic Sengekontacket Pond, it’s an ideal retreat for nature lovers, kayakers, or anyone looking to enjoy the Vineyard lifestyle. The home features a welcoming front porch and back deck—perfect spaces to relax, dine, or entertain outdoors. Inside, you'll find a warm

Erin Leighton Compass

71 6th St N, Edgartown, MA 02539
/58
$5,250,000 Open Fri 11:30AM - 12:30PM
- 5 Beds
- 5 Baths
- 4,185 Sq Ft
41 Crowell Ln, Tisbury, MA 02568

The wait is over, move right into your West Chop dream home! Located in the picturesque landscape of West Chop, this luxurious new development by Novo Builds offers an exquisite blend of modern design and coastal charm. Known for their innovative designs and high-quality craftsmanship, Novo Builds is transforming this iconic island with their latest project, providing an ideal sanctuary for

Joe & Nicole Holland Vineyard Dream Realty LLC

41 Crowell Ln, Tisbury, MA 02568
/26
$2,150,000
- 2 Beds
- 2.5 Baths
- 2,137 Sq Ft
30 Franklin Ave, Oak Bluffs, MA 02568

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

Stacy Ickes Donnelly + Co

30 Franklin Ave, Oak Bluffs, MA 02568
/16
$995,000
- 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
/40
$6,395,000
- 8 Beds
- 6.5 Baths
- 6,921 Sq Ft
19BC 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. There is also an additional 2.02 acre parcel included with purchase. 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

Brenda Galligan Karen M. Overtoom R.E.

19BC Locust Ln, Aquinnah, MA 02535
/55
$1,830,000
- 4 Beds
- 4 Baths
- 1,600 Sq Ft
12 & 14 Maple Ave, Oak Bluffs, MA 02557

Two Historic Oak Bluffs Cottages - Prime Location – Deeded SeparatelyPerched atop a gentle hill, surrounded by lush, established gardens in one of the island’s most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history—just a short distance to the harbor, downtown, and the beloved Winston’s takeout.Built at a time when

Leslie C. Floyd Portfolio Real Estate, Inc.

12 & 14 Maple Ave, Oak Bluffs, MA 02557
/108
$4,800,000
- 6 Beds
- 4.5 Baths
- 2,960 Sq Ft
104 Pond View Farm Rd, Vineyard Haven, MA 02568

An exceptional Waterfront Compound on Tisbury Great Pond. Located across the Tisbury Great Pond from the exclusive Blue Heron Farm, 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

Alexis Holden Tea Lane Associates

104 Pond View Farm Rd, Vineyard Haven, MA 02568
/42
$1,590,000
- 3 Beds
- 2 Baths
- 2,015 Sq Ft
48 Vineyard Avenue Extension, Oak Bluffs, MA 02568

Bright, Open Living, Steps from the Lagoon!Spacious and sun-filled, this charming 3-bedroom, 2-bath home offers effortless single-level living. As you enter the home, you're welcomed by a spacious sitting area that seamlessly flows into an open-concept living room, dining area, and modern kitchen—perfect for entertaining and everyday living. A separate home office or den provides

Susan Wallo Compass | The O'Hanlon Group

48 Vineyard Avenue Extension, Oak Bluffs, MA 02568
/21
$1,149,000
- 4 Beds
- 2 Baths
- 1,306 Sq Ft
113 Leonard Cir, Vineyard Haven, MA 02568

Adorable four bedroom cape features an updated open concept living, kitchen and dining area with a cozy screened in porch accessed via French doors. Wood floors, high ceilings and an abundance of windows throughout the home create a unified and pleasing aesthetic as well as a sense of light and spaciousness. Also included on the first floor are a bedroom with lots of natural light and a nicely

Alyson Parker Karen M. Overtoom R.E.

113 Leonard Cir, Vineyard Haven, MA 02568
/23
$1,790,000
- 2 Beds
- 1 Bath
- 600 Sq Ft
11 Beach Rd, Oak Bluffs, MA 02557

Oak Bluffs: Waterfront Property at Vineyard Haven Outer Harbor**This is an exceptional opportunity to acquire a stunning white sandy beach property on Vineyard Haven Harbor. This charming Island cottage boasts breathtaking panoramic views of the harbor and sound, showcasing magnificent sunsets each evening over the West Chop Peninsula. You can enjoy the lively boating scene, with yachts from

Alan Schweikert Ocean Park Realty Inc

11 Beach Rd, Oak Bluffs, MA 02557
/30
$829,000 Open Sat 11AM - 1PM
- 3 Beds
- 1 Bath
- 907 Sq Ft
17 Siloam Ave, Oak Bluffs, MA 02557

PRISTINE YEAR ROUND COTTAGE RENOVATED THROUGHOUT ~Welcome to 17 Siloam Avenue, a delightful cottage nestled in the historic Martha’s Vineyard Camp Meeting Association, offering spectacular sunset views of Sunset Lake and the distant harbor from its inviting porches. The current owners have cherished this home year-round for 13 years, and it’s easy to see why. This spacious residence features an

Marilyn Moses Ocean Park Realty Inc

17 Siloam Ave, 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
/39
$2,495,000
- 5 Beds
- 2.5 Baths
- 2,577 Sq Ft
16 Atlantic Ave, Oak Bluffs, MA 02557

East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most

Katherine Donahue Sandpiper Realty Inc

16 Atlantic Ave, Oak Bluffs, MA 02557
/16
$1,195,000
- 3 Beds
- 1.5 Baths
- 1,040 Sq Ft
50 Lantern Ln, Vineyard Haven, MA 02568

Nestled in a quiet enclave on Lantern Lane, this charming 3-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and island charm. Located just moments from the heart of Vineyard Haven, you'll enjoy easy access to shops, restaurants, and the ferry. The interior of the home features a bright and welcoming layout with an open living and dining area, hardwood floors, and a private

Madelyn Silvia Wallace & Co. Sotheby's International Realty

50 Lantern Ln, Vineyard Haven, MA 02568
/45
$19,500,000
- 7 Beds
- 5.5 Baths
- 3,344 Sq Ft
104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535

This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below.

Thomas Leclair Landvest MV

104 & 111 Old Herring Creek Rd, West Tisbury, 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
/32
$950,000
- 2 Beds
- 2 Baths
- 1,352 Sq Ft
400 Edgartown-Vineyard Haven Rd, Edgartown, MA 02539

Close to downtown Edgartown, yet far enough away to be in a residential location with a nice yard, this home is a must-see! This is a ranch style home with two bedrooms and two bathrooms, plus an office. Open concept for the living, dining and kitchen area with a slider to the back deck. With a few updates and finishing touches, this could transform into your perfect family home. It is being sold

Kelly Mercier The Agency

400 Edgartown-Vineyard Haven Rd, Edgartown, MA 02539
/29
$6,000,000
- 3 Beds
- 2 Baths
- 2,710 Sq Ft
35 S Bowl Rd, Chilmark, MA 02535

This exceptionally elegant and tranquil home in Seven Gates Farm combines contemporary architectural design with timeless high-end features for Vineyard casual, nature-inspired living. Extraordinary and rare, this move-in ready three-bedroom home with six-bedroom septic system sits on an oversized 5.3-acre parcel in Chilmark. This thoughtful layout has an easy flow, soothing tones with cypress

Meg Bodnar Tea Lane Associates

35 S Bowl Rd, Chilmark, MA 02535
/39
$1,669,000
- 3 Beds
- 4 Baths
- 2,308 Sq Ft
453 Lighthouse Rd, Aquinnah, MA 02535

Aquinnah Retreat set on a private 1.1-acre lot! This beautiful single-family home was lovingly built and cared for by one family, offering peaceful surroundings and ocean views. Now move-in ready, it's the perfect place for new owners to relax and make it their own. The wrap-around deck provides a scenic spot to enjoy the coastal air. Inside, the kitchen and dining area are filled with natural

We Close Deals Team Lamacchia Realty, Inc.

453 Lighthouse Rd, Aquinnah, MA 02535
/52
$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
/51
$7,350,000
- 4 Beds
- 5 Baths
- 3,490 Sq Ft
308 South Rd, Chilmark, MA 02535

Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chilmark residence offers a rare blend of privacy, elegance, and modern comfort. Originally built by Tom Tate and renovated in 2018, it exudes contemporary sophistication while embracing its natural surroundings. A private dock on Chilmark Pond provides direct water access and stunning South Shore sunsets.

Rose Ryley Sandpiper Realty Inc

308 South Rd, Chilmark, MA 02535
/44
$2,699,000
- 6 Beds
- 4 Baths
- 2,400 Sq Ft
111 Eastville Ave, Oak Bluffs, MA 02557

Motivated Seller!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location.FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated on an oversized lot that is two parcels away from the beach. This home offers six bedrooms and four

Ed Charter Arrowhead Homes

111 Eastville Ave, Oak Bluffs, MA 02557

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