5-Bedroom Homes for Sale in Dukes County MA

/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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/46
$2,395,000
- 5 Beds
- 3.5 Baths
- 3,873 Sq Ft
50 Hidden Cove Rd, Edgartown, MA 02539

Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The

Sean Federowicz Landmarks at TODAY Real Estate

50 Hidden Cove Rd, Edgartown, MA 02539
/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
/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
/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
/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
/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
/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
/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
/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
/43
$7,450,000
- 5 Beds
- 2.5 Baths
- 2,269 Sq Ft
34 Edys Island Way, Chilmark, MA 02535

Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by anIsland legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the

Jill Napior Tea Lane Associates

34 Edys Island Way, Chilmark, MA 02535
/37
$4,850,000
- 5 Beds
- 3 Baths
- 3,440 Sq Ft
146 Quansoo Rd, Chilmark, MA 02535

Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

Meg Bodnar Tea Lane Associates

146 Quansoo Rd, Chilmark, MA 02535
/60
$14,000,000
- 6 Beds
- 7 Baths
- 6,967 Sq Ft
8 Snail Rd, Chilmark, MA 02535

This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring

Alyssa Halisky Wallace & Co. Sotheby's

8 Snail Rd, Chilmark, MA 02535
/75
$19,900,000
- 5 Beds
- 7 Baths
- 6,577 Sq Ft
33 Boldwater Rd, Edgartown, MA 02539

Exquisite Waterfront Retreat - A rare opportunity to purchase a meticulously crafted 5,600 square-foot stone main house and 900 square-foot stone guesthouse with pool in a naturalized wooded setting. This extraordinary compound redefines the conventions of traditional Vineyard architecture in the most charming and sophisticated of ways. The house was sited to offer views of Edgartown Great Pond

Deb Hancock Hancock Real Estate

33 Boldwater Rd, Edgartown, MA 02539
/39
$10,500,000
- 8 Beds
- 6 Baths
- 3,888 Sq Ft
47 E Chop Dr, Oak Bluffs, MA 02568

East Chop waterfront - Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its

Perry Patterson MV Luxury Homes, LLC

47 E Chop Dr, Oak Bluffs, MA 02568
/46
$14,500,000
- 8 Beds
- 7.5 Baths
- 8,912 Sq Ft
30 Crackatuxet Cove Rd, Edgartown, MA 02539

This dramatic contemporary styled house lies on 6.5-acres of beautiful pond front land in the exclusive Herring Creek Farm. The home features cathedral ceilings throughout and an open floor plan with large living room, dining room and kitchen, all with clear story light, fireplaces and 20 ft. breakaway Nana walls. The spiral staircase leads from the living room to a large roof deck with expansive

Gerrett Conover Landvest MV

30 Crackatuxet Cove Rd, Edgartown, MA 02539
/31
$7,250,000
- 5 Beds
- 6.5 Baths
- 5,454 Sq Ft
54 Fuller St, Edgartown, MA 02539

This stately Greek Revival home lies on beautiful Fuller Street and a short walk to the beach. This 5-bedroom / 5.5-bath home features a beautiful foyer with arches and paneling leading past a grand staircase to a beautiful family room, kitchen and screened porch overlooking the backyard. There is an ensuite ground first floor bedroom and office off the hall as well as a side mudroom entry and

Gerrett Conover Landvest MV

54 Fuller St, Edgartown, MA 02539
/37
$2,995,000
- 5 Beds
- 4.5 Baths
- 4,115 Sq Ft
357 W Tisbury Rd, Edgartown, MA 02539

Here is the Edgartown compound you've been waiting for - a 5-bedroom main house, 2-bedroom guest house, and elevated swimming pool area located on 1.5 acres. Next door there is 25 acres of conservation land. The property is barely 2/10s of a mile to Morning Glory Farm, and just a mile and a half to the village on the bike path. The house combines island country charm with modern amenities - honey

Bonnie Pierce Wallace & Co. Sotheby's International Realty

357 W Tisbury Rd, Edgartown, MA 02539
/42
$3,195,000
- 5 Beds
- 4 Baths
- 2,300 Sq Ft
27 Spring St, Vineyard Haven, MA 02568

Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features five fireplaces, (one currently hidden behind a plastered wall), a gracious living room, dining room,

Alexis Holden Tea Lane Associates

27 Spring St, Vineyard Haven, MA 02568
/41
$1,650,000
- 5 Beds
- 3.5 Baths
- 4,032 Sq Ft
36 Ferro Way, Tisbury, MA 02568

36 Ferro Way, Vineyard Haven – A Stunning Colonial on Martha’s VineyardWelcome to 36 Ferro Way, a beautifully crafted Colonial-style home nestled in the heart of world-famous Martha’s Vineyard. This exceptional five-bedroom, three-and-a-half-bathroom residence boasts an expansive floor plan, abundant natural light, and a charming farmer’s porch that warmly invites you inside.Step into the heart

Michael Harney Sotheby's International Realty

36 Ferro Way, Tisbury, MA 02568
/35
$1,870,000
- 5 Beds
- 3 Baths
- 2,432 Sq Ft
32 Flamingo Dr, Edgartown, MA 02539

This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first

Skip Dostal Martha's Vineyard R.E.

32 Flamingo Dr, Edgartown, MA 02539
/41
$7,950,000
- 5 Beds
- 7 Baths
- 3,762 Sq Ft
85 Reservoir Rd, Vineyard Haven, MA 02568

Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

Alyssa Halisky Wallace & Co. Sotheby's International Realty

85 Reservoir Rd, Vineyard Haven, MA 02568
/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
/73
$13,995,000
- 7 Beds
- 9 Baths
- 6,343 Sq Ft
5 Briggs Rd, Edgartown, MA 02539

NEW CONSTRUCTION - COMPLETED. POND FRONT on WINTUCKET COVE. The epitome of Luxury Living, yet understated. 6,343 sq.ft., 7 Bed, 9 Bath home, w/16ft x 42ft saltwater heated pool, 2 car garage & a dramatic over sized screened porch w/11ft high ceilings. Discover a beautiful Vineyard oasis on 9.2 acres of land on the South Shore w/376ft of frontage on Wintucket Cove. An expansive property, merging

Alisan Lohan-Conway Alisan Lohan-Conway Properties

5 Briggs Rd, Edgartown, MA 02539
/42
$19,900,000
- 8 Beds
- 7.5 Baths
- 6,041 Sq Ft
114 N Water St, Edgartown, MA 02539

The property is currently rented; showings require a minimum of 48 hours’ notice. Move-In Ready – CONSTRUCTION COMPLETE - This stunning 8-bedroom, 7.5-bath generational home, completed in 2025, is fully furnished and move-in ready. The property features a 6-bedroom, 5.5-bath main residence, a 1-bedroom, 1-bath guest house with its own kitchen, and a 2-car carriage house with 1-bedroom living

Erin Hegarty Compass

114 N Water St, Edgartown, MA 02539
/29
$2,500,000 Open Sun 11AM - 1PM
- 6 Beds
- 3.5 Baths
- 1,616 Sq Ft
34 Massasoit Ave, Oak Bluffs, MA 02568

Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to

Carleen Cordwell Anchor Realty of Martha's Vineyard

34 Massasoit Ave, Oak Bluffs, MA 02568
/52
$7,795,000
- 7 Beds
- 4.5 Baths
- 6,921 Sq Ft
19 Locust Ln, Aquinnah, MA 02535

This beautifully designed and built home is privately sited on 12.23 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

Brenda Galligan Karen M. Overtoom R.E.

19 Locust Ln, Aquinnah, MA 02535
/42
$7,775,000
- 6 Beds
- 34.5 Baths
- 5,982 Sq Ft
19 Locust Ln, Aquinnah, MA 02535

This beautifully designed and built home is privately sited on 12.23 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

Brenda Galligan Karen M. Overtoom R.E.

19 Locust Ln, Aquinnah, MA 02535
/23
$1,625,000
- 5 Beds
- 5 Baths
- 2,316 Sq Ft
345 North Rd, Chilmark, MA 02535

Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard.

Mark Jenkins Wallace & Co. Sotheby's International Realty

345 North Rd, Chilmark, MA 02535
/18
$15,950,000
- 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,

Thomas Wallace Wallace & Co. Sotheby's International Realty

68 N Water St, Edgartown, MA 02539
/27
$9,750,000
- 5 Beds
- 7 Baths
- 4,078 Sq Ft
1 Field Club Dr, Edgartown, MA 02539

Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and

Thomas Wallace Wallace & Co. Sotheby's

1 Field Club Dr, 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
/28
$10,500,000
- 7 Beds
- 6 Baths
- 3,888 Sq Ft
47 E Chop Dr, Oak Bluffs, MA 02568

East Chop direct waterfront – Enjoy the ultimate. in waterfront living experiences. Features 6 bedrooms, spectacular water views, dock with 9 slips, and just steps from beaches, tennis club, downtown and ferries to mainland! Property has been extensively renovated recently. Uses include -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion,2.) Currently

Perry Patterson MV Luxury Homes LLC

47 E Chop Dr, Oak Bluffs, MA 02568
/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 house & 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

Leslie Graham Anchor Realty of Martha's Vineyard

55 Old House Way, West Tisbury, MA 02575

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