Dukes, MA Homes

/34
$2,700,000
- 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
/21
$9,500 per month
- 4 Beds
- 2 Baths
- 1,579 Sq Ft
- House for Rent
155 Skiff Ave, Vineyard Haven, MA 02568

Enjoy the serenity of a four bedroom, two full bathroom peaceful oasis complete with private in-ground pool. Close to lively dining and boutiques of downtown Vineyard Haven. Unwind at neighborhood beaches; Eastville, Owen Park, Tashmoo beaches all just a few minutes drive from your vacation retreat.This lovely home spread over 1600ft of living area provides first and second floor living and

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

155 Skiff Ave, Vineyard Haven, MA 02568
/41
$1,850,000 Sold Aug 04, 2025
- 2,210 Sq Ft
- $837/SF
- 22 Days On Market
- 3 Beds
- 3 Baths
- Built 1980
26 Tia Anna Ln, Oak Bluffs, MA 02557

Welcome to 26 Tia Anna Lane! This exquisite residence is immaculate, stylish, and fully renovated, ready to welcome its new owners! Situated on a beautifully landscaped 0.30-acre lot adorned with vibrant plantings, the home boasts pristine conditions both inside and out, featuring newer Hardi Plank siding. The inviting farmer's porch, complete with Mahogany decking, sets the tone for this

Marilyn Moses Ocean Park Realty Inc

26 Tia Anna Ln, Oak Bluffs, MA 02557

/3
Est $1,537,478 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,329 Sq Ft
18 Towanticut Ave, Oak Bluffs, MA 02557

18 Towanticut Ave, Oak Bluffs, MA 02557

/45
$1,250,000
- 2 Beds
- 3 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
/41
$13,500 per month
- 5 Beds
- 5.5 Baths
- 3,000 Sq Ft
- House for Rent
14 Bernard Cir, Vineyard Haven, MA 02568

Unwind in the private luxury of this BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar - fully

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

14 Bernard Cir, Vineyard Haven, MA 02568
/22
$1,000,000 Sold Jul 31, 2025
- 768 Sq Ft
- $1302/SF
- 96 Days On Market
- 2 Beds
- 1 Bath
- Built 1960
130 Wing Rd, Oak Bluffs, MA 02557

This well-maintained property is beautifully landscaped with gardens and generous lawn areas, offering incredible potential for growth and development. Conveniently located close to downtown Oak Bluffs, this property offers easy access to essential amenities and tourist destinations, whether you're driving, biking or relying on public transportation to restaurants, shops, beaches, bike paths and

Lynn Buder Sandpiper Realty Inc

130 Wing Rd, Oak Bluffs, MA 02557

/36
Est $2,634,274 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,470 Sq Ft
28 Woodhaven Dr, Edgartown, MA 02539

28 Woodhaven Dr, Edgartown, MA 02539

/27
$1,170,000 Pending
- 3 Beds
- 2 Baths
- 1,512 Sq Ft
62 Jernegan Ave, Edgartown, MA 02539

Charming 3-Bedroom, 2-Bath Ranch in Edgartown – Spacious, Private, and Conveniently Located Discover this inviting 3-bedroom, 2 full bath ranch-style home set on a generous .5 acre lot in a quiet, private area of Edgartown. Featuring an open-concept layout, this home offers seamless flow between the living, dining, and kitchen spaces—ideal for both everyday living and entertaining. The spacious

Nicholas Silvestri

Keller Williams Realty Evolution

(508) 290-4981

62 Jernegan Ave, Edgartown, MA 02539
/41
$8,750 per month
- 4 Beds
- 2.5 Baths
- 1,811 Sq Ft
- House for Rent
11 High Meadow Ln, Vineyard Haven, MA 02568

Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor full bath, plus additional half bath on main level. The

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

11 High Meadow Ln, Vineyard Haven, MA 02568
/44
$1,650,000 Sold Jul 29, 2025
- 2,320 Sq Ft
- $711/SF
- 35 Days On Market
- 4 Beds
- 2 Baths
- Built 1960
26 Manaquayak Rd, Vineyard Haven, MA 02568

Large comfortable and charming expanded Cape in a lovely setting very close to Lambert's Cove Beach and James Pond Preserve with special walking access to Swimming on Ice House Pond in the Manaquayak Preserve as well as deeded walking access to swim and boat on Seth's Pond. The living room is open to the beautiful newly-renovated kitchen and has an often-used wood-burning fireplace. There is a

Candy DaRosa Feiner Real Estate

26 Manaquayak Rd, Vineyard Haven, MA 02568

/21
Est $1,103,311 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,176 Sq Ft
10 Lagoon Rd, Oak Bluffs, MA 02557

10 Lagoon Rd, Oak Bluffs, MA 02557

/40
$2,495,000 Pending
- 5 Beds
- 5 Baths
- 3,213 Sq Ft
174 Tashmoo Ave, Vineyard Haven, MA 02568

Welcome to your dream home! The perfect blend of comfort and luxury awaits you in this custom-designed 5-bedroom, 4.5-bathroom residence. Over 3200 square feet of spacious living, upscale furnishings, finished basement with entertainment bar, and all the right touches to make every day feel like a retreat. Conveniently located under a half mile from downtown Vineyard Haven, where you will find

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 901-2347

174 Tashmoo Ave, Vineyard Haven, MA 02568
/14
$8,400 per month
- 4 Beds
- 3 Baths
- 2,148 Sq Ft
- House for Rent
39 Old Coach Rd, West Tisbury, MA 02568

Summer weekly rental only! June weekly rate is $8,400 and July weekly rate is $10,000/week - Sunday to Saturday. Recently renovated 4 bedroom, 3 bathroom home that sits on a private 2 acre lot in West Tisbury MA! This large cape house has just been update with new stainless steel appliances, new kitchen cabinets and countertops. Other updates include, new bathroom vanities and hardware,

Joseph D'Amico Dee Development Company

39 Old Coach Rd, West Tisbury, MA 02568
/12
$686,000 Sold Jul 23, 2025
- 725 Sq Ft
- $946/SF
- 31 Days On Market
- 2 Beds
- 1 Bath
- Built 1953
124 Skiff Ave Unit A-10, Vineyard Haven, MA 02568

Vineyard Haven Centrally located Causeway Condominiums just a short distance from town and ferries. Lovely grounds and a community swimming pool, a great place to live year-round or use as an investment property that's easy to manage. On ground level this spacious 2 bedroom condo with a tiled eat-in kitchen has a door accessing the back of condo. The tiled bathroom has been recently renovated and

Carleen Cordwell Anchor Realty of Martha's Vineyard

124 Skiff Ave Unit A-10, Vineyard Haven, MA 02568

/31
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,754 Sq Ft
12 Fairway Dr, Vineyard Haven, MA 02568

12 Fairway Dr, Vineyard Haven, MA 02568

/20
$929,000 Pending
- 3 Beds
- 2 Baths
- 1,286 Sq Ft
299 Franklin St, Vineyard Haven, MA 02568

Walkable to downtown Vineyard Haven, offering shops, dining, and waterfront access. Close to everything, yet tucked away on a peaceful corner lot is this classic 3-bedroom, 1.5-bathroom ranch home. The possibilities abound on a spacious .27-acre level yard where you can add more bedrooms and an ADU. The extra long detached 2-car garage with high ceilings is a great spot to store your vehicles

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 876-3522

299 Franklin St, Vineyard Haven, MA 02568
/27
$21,700 per month
- 5 Beds
- 3 Baths
- 2,168 Sq Ft
- House for Rent
97 3rd St N, Edgartown, MA 02539

YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

97 3rd St N, Edgartown, MA 02539
/32
$899,000 Sold Jul 11, 2025
- 955 Sq Ft
- $941/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1871
8 Rock Ave, Oak Bluffs, MA 02557

Experience the charm of this exquisitely renovated Victorian Gingerbread Cottage, nestled within the historic Martha's Vineyard Camp Meeting Association. Just moments away from Oak Bluffs Harbor, ferry terminals, art galleries, restaurants, public beaches, and vibrant shopping areas, this cottage offers an unparalleled location next to all of Oak Bluffs' picturesque parks.This rare gem

Marilyn Moses Ocean Park Realty Inc

8 Rock Ave, Oak Bluffs, MA 02557

/37
Est $1,519,629 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,754 Sq Ft
12 Fairway Dr, Oak Bluffs, MA 02557

12 Fairway Dr, Oak Bluffs, MA 02557

/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
/20
$14,000 per month
- 5 Beds
- 3 Baths
- 3,000 Sq Ft
- House for Rent
55 Samoset Ave, Oak Bluffs, MA 02557

Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

55 Samoset Ave, Oak Bluffs, MA 02557
/20
$1,715,000 Sold Jul 11, 2025
- 524 Sq Ft
- $3273/SF
- 72 Days On Market
- 1 Bed
- 1 Bath
- Built 1915
61 Hines Point Rd, Vineyard Haven, MA 02568

Tucked away on the serene shores of Lagoon Pond in Vineyard Haven, this cozy one-bedroom cottage offers the perfect island escape. Located on exclusive Hines Point, the home features stunning water views, direct access to a private beach, and the calming sounds of the tide just steps from your door. Inside, the cottage is thoughtfully designed for comfort and simplicity, with an open living area

Alyssa Halisky Wallace & Co. Sotheby's International Realty

61 Hines Point Rd, Vineyard Haven, MA 02568

/38
Est $1,055,023 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,120 Sq Ft
287 County Rd, Vineyard Haven, MA 02568

287 County Rd, Vineyard Haven, MA 02568

/32
$1,550,000
- 4 Beds
- 2 Baths
- 1,304 Sq Ft
11 John Wesley Ave, Oak Bluffs, MA 02568

East Chop Living in this 4 Bedroom Victorian home perched near the shoreline in Oak Bluffs-just a short stroll to the harbor, the shores of East Chop beaches, and the shops and restaurants of downtown Oak Bluffs. Built in 1905, and updated throughout the years, with its Victorian architecture softened by time and salt air, giving it an inviting, warm charm.The exterior features a wide

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 682-5574

11 John Wesley Ave, Oak Bluffs, MA 02568
/30
$28,500 per month
- 9 Beds
- 6.5 Baths
- 3,500 Sq Ft
- House for Rent
9 Tuckernuck Ave, Oak Bluffs, MA 02557

**PEAK SUMMER WEEKLY RATE** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and distinctive design.

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

9 Tuckernuck Ave, Oak Bluffs, MA 02557
/26
$1,400,000 Sold Jul 10, 2025
- 2,019 Sq Ft
- $693/SF
- 8 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1996
73 Dodgers Hole Rd, Edgartown, MA 02539

Situated on .5 acres in established Dodgers Hole, this well-maintained contemporary home has three bedrooms, including a primary ensuite on the first floor with a walk-in closet. Enjoy the cathedral-ceiling living room with a wood-burning fireplace and an adjacent light-filled sunroom with French doors to the deck. The eat-in kitchen is at the back of the house, with direct deck access. A

Stephanie Roache Donnelly + Co.

73 Dodgers Hole Rd, Edgartown, MA 02539

/17
Est $1,551,966 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,298 Sq Ft
19 Quantapog Rd, Vineyard Haven, MA 02568

19 Quantapog Rd, Vineyard Haven, MA 02568

/21
$1,795,000
- 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

(870) 917-0672

9 Brunswick Ave, Oak Bluffs, MA 02557
/10
$20,000 per month
- 5 Beds
- 3 Baths
- 2,352 Sq Ft
- House for Rent
55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

Karen Overtoom Karen M. Overtoom R.E.

55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
/22
$975,000 Sold Jul 07, 2025
- 940 Sq Ft
- $1037/SF
- 61 Days On Market
- 1 Bed
- 2 Baths
- Built 2025
128 Manchester Ave, Oak Bluffs, MA 02568

This delightful, modern cape-style home features thoughtful and impressive finish details. The covered porch welcomes you into the home where you will find well-appointed spaces. The kitchen has stainless appliances including a 5-burner gas range with pot filler, an LG French-door refrigerator and dishwasher. The kitchen area is finished with shiplap. There is an open dining and living area with

Michele Moore Island Real Estate

128 Manchester Ave, Oak Bluffs, MA 02568

/12
Est $1,307,200 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,997 Sq Ft
3 Carole Ave, Vineyard Haven, MA 02568

3 Carole Ave, Vineyard Haven, MA 02568

/42
$5,995,000 Open House 8/17
- 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) 274-5363

385 Barnes Rd, Vineyard Haven, MA 02568
/10
$8,500 per month
- 3 Beds
- 2 Baths
- House for Rent
29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

Karen Overtoom Karen M. Overtoom R.E.

29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
/46
$6,200,000 Sold Jul 03, 2025
- 3,278 Sq Ft
- $1891/SF
- 0 Days On Market
- 4 Beds
- 4 Baths
- Built 1983
79 Rachels Way, Vineyard Haven, MA 02568

EXTRAORDINARY COASTAL RETREAT IN MINK MEADOWS — Welcome to an idyllic haven on Martha’s Vineyard, tucked within the exclusive West Chop area of Tisbury. This contemporary residence offers sweeping water views across a vibrant salt marsh and out to the sparkling expanse of Vineyard Sound, where sailboats quietly pass by across the horizon. Built in 1983 and thoughtfully maintained with numerous

Jen O'Hanlon Compass | The O'Hanlon Group

79 Rachels Way, Vineyard Haven, MA 02568

/13
Est $1,234,075 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
33 Menahan St, Vineyard Haven, MA 02568

33 Menahan St, Vineyard Haven, MA 02568

/39
$2,645,000
- 3 Beds
- 2 Baths
- 1,350 Sq Ft
31 The Blvd, Edgartown, MA 02539

Waterfront Charmer on Sengekontacket Pond - Perched on the shoreline, this contemporary cottage is enveloped by stone walls, lush gardens, and stunning water views. Inside, a bright, airy living space features an open dining area and a well-appointed kitchen. The all-white interior is complemented by hardwood floors, vaulted ceilings, skylights, air conditioning, and ceiling fans. Three sliding

Wendy Harman

Compass

(508) 301-9323

31 The Blvd, Edgartown, MA 02539
/8
$11,800 per month
- 4 Beds
- 4 Baths
- 2,612 Sq Ft
- House for Rent
46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

Karen Overtoom Karen M. Overtoom R.E.

46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
/42
$2,900,000 Sold Jul 03, 2025
- 4,476 Sq Ft
- $648/SF
- 347 Days On Market
- 7 Beds
- 5.5 Baths
- Built 1997
67 Hidden Village Rd, Vineyard Haven, MA 02568

Picturesquely sited on a spacious 4.6-acre parcel this remarkable property is the perfect Vineyard retreat offering a luxurious home, guest house, fenced pastures, and a large barn. Just minutes from Lamberts Cove Beach and all the conveniences of West Tisbury Center, the location is ideal. Designed with three distinctive living levels providing spacious yet private surroundings. The main living

Stephanie Roache Donnelly + Co.

67 Hidden Village Rd, Vineyard Haven, MA 02568

/25
Est $2,093,611 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,636 Sq Ft
131 Shubael Weeks Path, Vineyard Haven, MA 02568

131 Shubael Weeks Path, Vineyard Haven, MA 02568

Showing Results 1 - 40, Page 1 of 18

Massachusetts Dukes County Vineyard Haven

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage