Dukes, MA Homes

/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
/2
$700,000 Sold Dec 06, 2024
- 1,066 Sq Ft
- $657/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 1868
29 Butler Ave, Oak Bluffs, MA 02557

This well hidden yet wonderfully sited cottage has loads of charm inside! With generous rooms that can multi task with ease, it's a project worthy of restoration. The circular flow of the first floor and several interior doors allows for a multitude of room uses. Front to back the first floor is expanded with a high ceilinged "sun parlor" as well as ample storage, charming built-ins and vintage

Helena Kirschenbaum Studio Realty

29 Butler Ave, Oak Bluffs, MA 02557

/27
Est $2,385,359 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,456 Sq Ft
80 Bellevue Ave, Vineyard Haven, MA 02568

80 Bellevue Ave, Vineyard Haven, MA 02568

/23
$1,164,000
- 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

Michele Moore Island Real Estate

96 Manchester Ave, Oak Bluffs, MA 02557
/26
$1,830,000 Sold Dec 05, 2024
- 1,862 Sq Ft
- $983/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 1960
82 South Rd, Chilmark, MA 02535

This charming Chilmark home sits on over 3 acres and features an updated, move-in ready home, expansive outdoor living space with deck, lawn and firepit area, and a six-bedroom septic system for future expansion. The welcoming foyer opens into the dining room, kitchen and a large airy living room with vaulted ceiling and stone fireplace. Beyond the kitchen there are two bedrooms and a shared

Meg Bodnar Tea Lane Associates

82 South Rd, Chilmark, MA 02535

/5
Est $1,833,874 Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,756 Sq Ft
47 Carl Lairs Ln, Vineyard Haven, MA 02568

47 Carl Lairs Ln, Vineyard Haven, MA 02568

/18
$1,195,000
- 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
/20
$1,100,000 Sold Dec 05, 2024
- 1,200 Sq Ft
- $917/SF
- 15 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
4 Mockingbird Dr, Edgartown, MA 02539

This 3BR, 1 & half BA salt box home in Dodger's Hole has been enjoyed by the same family for thirty years. First floor kitchen, dining and living are open concept with vaulted ceilings over the living and dining room. Also included on the first floor are a nice size bedroom and a half bath with laundry. Upstairs are two more bedrooms and a shared bath. Full unfinished basement. Recent

Alyson Parker Karen M. Overtoom R.E.

4 Mockingbird Dr, Edgartown, MA 02539

/22
Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 576 Sq Ft
189 Winyah Ln, Vineyard Haven, MA 02568

189 Winyah Ln, Vineyard Haven, MA 02568

/37
$3,400,000
- 5 Beds
- 2 Baths
- 3,133 Sq Ft
19 Old Woods Rd, Chilmark, MA 02535

Nestled in the heart of Chilmark, this 12.5-acre property offers two charming dwellings, each with 3 bedrooms, set in a landscape of privacy and timeless Vineyard character. Built in 1950 and 1963 for American artist, Thomas Hart Benton, the homes were lovingly created as a compound for friends and family to return to year after year. Tucked down a quiet driveway, the two share a special legacy

Cheri Mason Landvest MV

19 Old Woods Rd, Chilmark, MA 02535
/32
$1,585,000 Sold Dec 05, 2024
- 1,949 Sq Ft
- $813/SF
- 53 Days On Market
- 3 Beds
- 3 Baths
- Built 2016
42 8th St N, Edgartown, MA 02539

Located at the end of a quiet street in Edgartown, yet convenient to all down-island amenities and public access to Sengekontacket, stands this custom three-bedroom home. Offering a casual, yet practical layout, complete with a large living area accented with propane fireplace and spacious kitchen with separate dining area. The quality is carried to the exterior, where you can enjoy the lush

Katie Donahue Sandpiper Realty

42 8th St N, Edgartown, MA 02539

/35
Est $1,489,160 Not Listed For Sale
- 1 Bed
- 1.5 Baths
- 1,123 Sq Ft
53 Weaver Ln, Vineyard Haven, MA 02568

53 Weaver Ln, Vineyard Haven, MA 02568

/11
$1,250,000
- Land
- 6 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
/20
$1,000,000 Sold Dec 04, 2024
- 1,701 Sq Ft
- $588/SF
- 9 Days On Market
- 3 Beds
- 2 Baths
- Built 1989
16 Hudson Ave, Oak Bluffs, MA 02557

This three-bedroom, two-bathroom Cape home is nestled in a quiet neighborhood with woodsy areas on two sides. This location offers easy access to walking trails, bike path, Lagoon, Farm Neck Golf Club/ Café, dog park, and downtown Oak Bluffs is just a mile and a half away.The first floor has a kitchen with granite counter tops which is built for efficiency and feeds directly into the

JoJo Lambert Island Home Realty Inc.

16 Hudson Ave, Oak Bluffs, MA 02557

/20
Est $1,060,480 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,200 Sq Ft
33 Renear St, Vineyard Haven, MA 02568

33 Renear St, Vineyard Haven, MA 02568

/2
$199,000
- Land
- 0.52 Acre
- $382,692 per Acre
36 Boylston Dr Unit 1.329, Edgartown, MA 02539

Unique OPPORTUNITY with POSSIBILITIES! .52 acres of flat vacant land in a convenient and super location! Bounds have been flagged. This property is being sold as is and Currently Unbuildable. A Buyer is responsible to confirm what the town will allow. Think creatively! Sellers motivated!

Martha Smith C McManus Realty Group

36 Boylston Dr Unit 1.329, Edgartown, MA 02539
/26
$2,100,000 Sold Dec 03, 2024
- 680 Sq Ft
- $3088/SF
- 1 Day On Market
- 2 Beds
- 1 Bath
- Built 1978
59 The Blvd, Edgartown, MA 02539

Waterfront cottage

Jennifer DaSilva Compass | Point B

59 The Blvd, Edgartown, MA 02539

/16
Est $1,937,648 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,068 Sq Ft
39 Burts Way, Vineyard Haven, MA 02568

39 Burts Way, Vineyard Haven, MA 02568

/40
$6,395,000
- 8 Beds
- 7 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
/24
$1,900,000 Sold Dec 03, 2024
- 2,672 Sq Ft
- $711/SF
- 211 Days On Market
- 4 Beds
- 4 Baths
- Built 2016
142 Lake St, Vineyard Haven, MA 02568

Modern Contemporary designed by noted Vineyard architect, Bruce MacNelly. The furnishings (excluding artwork) complete the design. You can move in and unpack. The well-designed layout provides plenty of room for family and friends to gather while having ample private spaces to relax or work from home.The first floor is bright with open Living, Dining, Kitchen. Large doors open out to the deck

Kathryn Tate Kathryn Tate Gothard

142 Lake St, Vineyard Haven, MA 02568

/42
Est $1,739,614 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,677 Sq Ft
201 Lagoon Pond Rd, Vineyard Haven, MA 02568

201 Lagoon Pond Rd, Vineyard Haven, MA 02568

/42
$1,675,000
- 3 Beds
- 2 Baths
- 2,015 Sq Ft
48 Vineyard Avenue Extension, Oak Bluffs, MA 02568

Bright, Open Living Steps from the Lagoon!This sun-filled 3-bedroom, 2-bath home offers easy single-level living with a spacious, open-concept layout—ideal for entertaining and everyday comfort. A welcoming sitting area flows into the living room, dining space, and modern kitchen. A separate home office/den adds flexibility to this 2,015 sq ft home. Set on a generous 11,000 sq ft corner lot,

Susie Wallo Compass

48 Vineyard Avenue Extension, Oak Bluffs, MA 02568
/4
$1,350,000 Sold Dec 03, 2024
- 2,179 Sq Ft
- $620/SF
- 0 Days On Market
- 4 Beds
- 2 Baths
- Built 1987
47 Willow Tree Hollow Rd, West Tisbury, MA 02568

SERENE & PRIVATE WEST TISBURY PROPERTY - Down a country lane off West Tisbury Road, this 1.55 acre property is a serene location for a vacation or year round home. Set on a knoll with established gardens, the outdoor spaces are cool and inviting with a large deck, level back yard, and an outdoor shower. Newly painted walls and trim throughout. There is room to spread out and relax after a day

Leslie Floyd Portfolio Real Estate Inc.

47 Willow Tree Hollow Rd, West Tisbury, MA 02568

/23
Est $1,557,173 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,200 Sq Ft
26 Davis St, Vineyard Haven, MA 02568

26 Davis St, Vineyard Haven, MA 02568

/108
$4,800,000
- 6 Beds
- 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
/17
$310,000 Sold Dec 02, 2024
- 279 Sq Ft
- $1111/SF
- 223 Days On Market
- 1 Bed
- 1 Bath
- Built 1950
15 Mill St Unit 31F, Edgartown, MA 02539

Edgartown Commons Condo – Seasonal pied de terre and solid investment opportunity.Located steps from charming downtown Edgartown, this beautifully furnished second-floor studio unit is bright, clean, and comfortable. Conveniently located near the pool and hot tub, where you can relax in the sunshine between trips to the beach. Just a short stroll to Edgartown harbor, Fuller Street Beach,

Michele Moore Island Real Estate

15 Mill St Unit 31F, Edgartown, MA 02539

/10
Est $1,395,925 Not Listed For Sale
- 4 Beds
35 Mount Aldworth Rd, Vineyard Haven, MA 02568

35 Mount Aldworth Rd, Vineyard Haven, MA 02568

/8
$749,500
- Land
- 0.26 Acre
- $2,882,692 per Acre
35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557

Welcome to Lagoon Ridge.....Oak Bluffs’ newest and most sought-after neighborhood! Build your 3 bedroom dream home with M Duffany Builders on this lofty setting, 95 feet above Lagoon Pond, featuring sweeping sky views, colorful sunsets, and refreshing salty sea breezes. This exceptional building lot is among the last of the remaining opportunities in this thriving new community. Utilities are

Marilyn Moses Ocean Park Realty Inc

35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
/20
$870,000 Sold Nov 26, 2024
- 1,024 Sq Ft
- $850/SF
- 7 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
57 Netock Ave, Oak Bluffs, MA 02557

Charming three-bedroom home just under a mile from downtown Oak Bluffs where the restaurants, shops, beaches, and lively harborfront await! The casual design offers an open-concept first-floor layout, which flows easily onto a large deck, expanding your seasonal living space. The spacious shed is ideal for storing all beach, bike, and boating gear or a creative space for recreation and fun on a

Katie Donahue Sandpiper Realty

57 Netock Ave, Oak Bluffs, MA 02557

/25
Est $1,029,939 Not Listed For Sale
- 1 Bed
- 1 Bath
- 1,244 Sq Ft
21 Walker Way, Vineyard Haven, MA 02568

21 Walker Way, Vineyard Haven, MA 02568

/4
$1,725,000
- Land
- 2.00 Acres
- $862,500 per Acre
501 W Tisbury Rd, Edgartown, MA 02539

Prime 2-acre parcel situated close to the bike path, state forest, Morning Glory Farm and Edgartown village. Per Edgartown BOH, this lot is approved to support a 5-bedroom home with a standard septic system. Additionally, with an advanced treatment system and a variance, the potential exists to expand with one or two extra bedrooms. Enjoy the perfect blend of convenience and tranquility in this

Stacy Ickes Donnelly + Co.

501 W Tisbury Rd, Edgartown, MA 02539
/20
$870,000 Sold Nov 26, 2024
- 1,024 Sq Ft
- $850/SF
- 7 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1986
57 Netock Ave, Oak Bluffs, MA 02568

Charming three-bedroom home just under a mile from downtown Oak Bluffs where the restaurants, shops, beaches, and lively harborfront await! The casual design offers an open-concept first-floor layout, which flows easily onto a large deck, expanding your seasonal living space. The spacious shed is ideal for storing all beach, bike, and boating gear or a creative space for recreation and fun on a

Katherine Donahue Sandpiper Realty Inc

57 Netock Ave, Oak Bluffs, MA 02568

/6
Est $626,208 Not Listed For Sale
- 3 Beds
92 Rogers Farm Rd, Vineyard Haven, MA 02568

92 Rogers Farm Rd, Vineyard Haven, MA 02568

/4
$1,725,000
- Land
- 2.00 Acres
- $862,500 per Acre
501 W Tisbury Rd Unit 2.1, Edgartown, MA 02539

Prime 2-acre parcel situated close to the bike path, state forest, Morning Glory Farm and Edgartown village. Per Edgartown BOH, this lot is approved to support a 5-bedroom home with a standard septic system. Additionally, with an advanced treatment system and a variance, the potential exists to expand with one or two extra bedrooms. Enjoy the perfect blend of convenience and tranquility in this

Stacy Ickes Donnelly + Co

501 W Tisbury Rd Unit 2.1, Edgartown, MA 02539
/7
$4,251,350 Sold Nov 25, 2024
- 3,299 Sq Ft
- $1289/SF
- 39 Days On Market
- 4 Beds
- 5 Baths
- Built 2024
57 Curtis Ln, Edgartown, MA 02539

The sales price of $4,251,350 did NOT include landscape, hardscape, spa install, pool upgrade, and many other upgrades.

Michele Casavant Vineyard Village Realty

57 Curtis Ln, Edgartown, MA 02539

/17
Est $1,158,023 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,111 Sq Ft
48 Look St, Vineyard Haven, MA 02568

48 Look St, Vineyard Haven, MA 02568

/63
$5,975,000
- 5 Beds
- 4 Baths
- 4,050 Sq Ft
78 Hammett Rd, Chilmark, MA 02535

Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

Robert Kenney Tea Lane Associates

78 Hammett Rd, Chilmark, MA 02535
/33
$1,300,000 Sold Nov 22, 2024
- 1,704 Sq Ft
- $763/SF
- 114 Days On Market
- 3 Beds
- 2 Baths
- Built 1980
38 Schoolhouse Village, Oak Bluffs, MA 02568

WELCOME TO ROSEWOOD COTTAGE - This meticulously cared for, and conveniently located home, is just minutes from the centers of three island towns. The property currently consists of three bedrooms and two full bathrooms. Previously used as a four bedroom prior to the expansion of the first floor master. There is an additional 600+ square feet of finished space in the lower level which includes a

John O'Connell Portfolio Real Estate, Inc.

38 Schoolhouse Village, Oak Bluffs, MA 02568

/25
Est $1,237,219 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,171 Sq Ft
112 Spring St, Vineyard Haven, MA 02568

112 Spring St, 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

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