Dukes, MA Homes

/91
$1,895,000 Open Fri 10AM - 12PM
- 3 Beds
- 3 Baths
- 1,406 Sq Ft
17 John Wesley Ave, Vineyard Haven, MA 02568

Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor

kyle Neyer Tea Lane Associates

17 John Wesley Ave, Vineyard Haven, MA 02568
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/11
$12,500 per month
- 4 Beds
- 1.5 Baths
- 1,413 Sq Ft
- House for Rent
11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. This antique Vineyard home is thoughtfully styled with classic country-chic interior decor. The wraparound porch has plenty of room to enjoy people watching or sipping ice cold tea, perfect for a hot summer day. Alternatively, you can enjoy peering down the street from the master bedroom which opens up to a charming porch with plenty of room for two to enjoy

Karen Overtoom Karen M. Overtoom R.E.

11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557
/24
$665,000 Sold May 23, 2025
- 806 Sq Ft
- $825/SF
- 171 Days On Market
- 3 Beds
- 2 Baths
- Built 1876
51 Rural Cir, Oak Bluffs, MA 02557

The Spirit of '76 is a lovely Campground cottage nestled into the landscape for privacy and shade. Just a couple of blocks to the beach, town center, shops, and restaurants. A fabulous wrap around porch with various seating areas. Built in 1876 this wonderful throwback of yesteryear features some original furnishings included in the sale. With a classic front parlor, dining room, and kitchen, a

Lisa Lucier Anchor Realty of Martha's Vineyard

51 Rural Cir, Oak Bluffs, MA 02557

/18
Est $1,345,375 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,764 Sq Ft
46 Lake Ave, Edgartown, MA 02539

46 Lake Ave, Edgartown, MA 02539

/42
$2,125,000
- 3 Beds
- 4 Baths
- 2,558 Sq Ft
35 Tower Ridge Rd, Oak Bluffs, MA 02557

Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

Katherine Donahue Sandpiper Realty Inc

35 Tower Ridge Rd, Oak Bluffs, MA 02557
/9
$6,500 per month
- 3 Beds
- 3 Baths
- 1,645 Sq Ft
- House for Rent
23 Ocean Ave Unit OB539, Edgartown, MA 02539

THIS IS A SUMMER WEEKLY RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Victorian Cottage located on Ocean Park in the heart of Oak Bluffs with fully equipped and updated kitchen, five bedrooms and three baths, cozy living spaces and multiple amenities will accommodate your family and friends. Smell the sea air and watch the waves break from your front porch. This charming beach house is steps away

Karen Overtoom Karen M. Overtoom R.E.

23 Ocean Ave Unit OB539, Edgartown, MA 02539
/27
$1,600,000 Sold May 22, 2025
- 1,594 Sq Ft
- $1004/SF
- 532 Days On Market
- 3 Beds
- 2 Baths
- Built 1933
2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the

Carol Shore Donnelly + Co

2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

/32
Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,107 Sq Ft
8 Clinton Ave, Oak Bluffs, MA 02568

8 Clinton Ave, Oak Bluffs, MA 02568

/46
$2,495,000
- 5 Beds
- 4 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
/11
$21,000 per month
- 3 Beds
- 2 Baths
- 1,481 Sq Ft
- House for Rent
24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568

THIS IS A SUMMER RENTAL ONLY. Centrally located to Edgartown, Vineyard Haven and Oak Bluffs. Just a short drive will take you to any of the town beaches and the Sailing Camp Park is a quick bike ride away. The home is located on over a 1/2 acre of landscaped property in a beautiful, private, neighborhood, with private roads great for biking and is wonderful for families, friends or even a

Karen Overtoom Karen M. Overtoom R.E.

24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568
/36
$5,500,000 Sold May 20, 2025
- 3,262 Sq Ft
- $1686/SF
- 295 Days On Market
- 4 Beds
- 5 Baths
- Built 1984
12 Tamarack Ln, Oak Bluffs, MA 02536

This bright and sunny home has a spectacular waterview overlooking the Eighth Fairway of Farm Neck Golf Course, Sengekontacket Pond and Nantucket Sound. Professionaly designed landscaping with perennial beds and charming brick courtyard add to its ambiance. Included are Farm Neck Golf Club stockholder membership (meaning immediate entry into golf membership), tennis and dock & mooring privileges.

Betsy Kessler Rutledge Properties

12 Tamarack Ln, Oak Bluffs, MA 02536

/31
Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,520 Sq Ft
107 & 105 Barnes Rd, Oak Bluffs, MA 02557

107 & 105 Barnes Rd, Oak Bluffs, MA 02557

/45
$1,899,000
- 4 Beds
- 3 Baths
- 2,127 Sq Ft
5 Bayes Hill Cir, Vineyard Haven, MA 02568

On a quiet cul-de-sac in the Bayes Hill neighborhood is this spacious traditional Colonial-style home adorned with charm. As you enter the home from the idyllic covered porch, you are welcomed into the foyer. The home is filled with intimate spaces while offering the opportunity for larger parties to gather. The living room has built-in shelving that flank the gas fireplace and it is connected to

Rene Jackson Island Real Estate

5 Bayes Hill Cir, Vineyard Haven, MA 02568
/14
$20,000 per month
- 3 Beds
- 1 Bath
- 1,629 Sq Ft
- House for Rent
67 New York Ave Unit OB536, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. 1900 Oak Bluffs Victorian. Ten minute walk to Nancy’s restaurant/downtown OB and 1/2 mile walk to Jetty beach in East Chop. The house was purchased empty in 2018 so all furnishings are new and the house is freshly painted. On the second floor, there are 3 bedrooms and a full bathroom, which connects to hall and master bedroom. Two bedrooms include queen beds and

Karen Overtoom Karen M. Overtoom R.E.

67 New York Ave Unit OB536, Oak Bluffs, MA 02557
/45
$1,225,000 Sold May 19, 2025
- 1,725 Sq Ft
- $710/SF
- 338 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
51 Head of the Pond Rd, Vineyard Haven, MA 02568

Iron Hill, Centrally located with convenient access to Island villages. 3 Bedroom, 2 Bath Ranch on 1.5+ acres. An empty canvas with limitless possibilities. Mature landscaping designed for privacy, aesthetics, and low maintenance. Paved private road access, with generous setback for residence. Bike path, Bus stop, State Forest, & Walking Trails nearby. Association covenants allow up to two

Bruce Stuart Bruce Stuart and Associates

51 Head of the Pond Rd, Vineyard Haven, MA 02568

/14
Not Listed For Sale
- 2 Beds
- 3 Baths
3 Hope's Way, Oak Bluffs, MA 02568

3 Hope's Way, Oak Bluffs, 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
/16
$40,000 per month
- 4 Beds
- 3 Baths
- 2,748 Sq Ft
- House for Rent
38 Farm Pond Ob524, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. Gracious 4 bedroom home with private beach access and tennis. This home has a reverse design that has been fully renovated and thoughtfully decorated. There is a large deck overlooking gardens and a peep of the water. A separate studio is attached by the deck. You are a short distance from town, less than a mile to the public beach and a minutes to a beautiful

Karen Overtoom Karen M. Overtoom R.E.

38 Farm Pond Ob524, Oak Bluffs, MA 02557
/26
$1,665,000 Sold May 02, 2025
- 2,408 Sq Ft
- $691/SF
- 300 Days On Market
- 3 Beds
- 3 Baths
- Built 1986
33 Clay Ave, Oak Bluffs, MA 02557

East Chop - Tucked away on a quiet tree-lined street, you will find this contemporary three-bedroom home. A distinctive floor plan provides ample living spaces on all three levels. The expansive outdoor deck and large yard expand the living space and are the perfect places to enjoy the quiet setting. The unique layout and five-bedroom septic allows easy reconfiguration. A fantastic opportunity to

Katherine Donahue Sandpiper Realty Inc

33 Clay Ave, Oak Bluffs, MA 02557

/26
Est $992,599 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,355 Sq Ft
4 Quail Run Unit 5, Oak Bluffs, MA 02557

4 Quail Run Unit 5, Oak Bluffs, MA 02557

/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
/21
$13,000 per month
- 4 Beds
- 3 Baths
- 2,500 Sq Ft
- House for Rent
14 Pulpit Rock Rd, Oak Bluffs, MA 02557

PRICES ARE WEEKLY NOT MONTHLY. Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several walking trails. Just minutes to Farm Neck Golf Course, beaches and town.

Karen Overtoom Karen M. Overtoom R.E.

14 Pulpit Rock Rd, Oak Bluffs, MA 02557
/32
$1,100,000 Sold May 01, 2025
- 1,680 Sq Ft
- $655/SF
- 172 Days On Market
- 2 Beds
- 4 Baths
- Built 2003
10 Nunes Way, Oak Bluffs, MA 02557

On approximately .40 of an acre this 21 year old home has much to offer. In a very convenient location close to theFarm Neck golf course, O.B. elementary school, and a land bank conservation property - the 72 acre Tradewinds Field Reserve dog park. Two decks provide summertime fun and the walk out basement with bath offers an opportunity to finish off more living space. An excellent floor plan

Neal Stiller Cronigs Real Estate

10 Nunes Way, Oak Bluffs, MA 02557

/20
Not Listed For Sale
- 1 Bed
- 1 Bath
- 354 Sq Ft
2 Lincoln Ave, Oak Bluffs, MA 02568

2 Lincoln Ave, Oak Bluffs, 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
/15
$40,000 per month
- 6 Beds
- 3 Baths
- 1,704 Sq Ft
- House for Rent
120 Eastville Ave Ob520, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. Watch the boats come and go from the harbor while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom guest house also offers your own dock and mooring.

Karen Overtoom Karen M. Overtoom R.E.

120 Eastville Ave Ob520, Oak Bluffs, MA 02557
/20
$675,000 Sold Apr 23, 2025
- 508 Sq Ft
- $1329/SF
- 298 Days On Market
- 2 Beds
- 2 Baths
- Built 1868
9 Forest Cir, Oak Bluffs, MA 02557

The Size will Surprise~ Cloud Nine~ Located on a quiet hidden circle with 14 enchanting cottages in the Historic Martha's Vineyard Camp Meeting Association. Steps to Circuit Avenue, beaches, shops, ferries, and restaurants. This YEAR ROUND RENOVATED Charming Cottage is FULLY INSULATED with spray foam and in 2022 Brennan and Co. installed a Daikin Multi Position Air Handler with thermostat to

Marilyn Moses Ocean Park Realty Inc

9 Forest Cir, Oak Bluffs, MA 02557

/44
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,746 Sq Ft
64 & 66 Garvin St, Oak Bluffs, MA 02557

64 & 66 Garvin St, Oak Bluffs, MA 02557

/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
/8
$56,000 per month
- 4 Beds
- 2.5 Baths
- 3,000 Sq Ft
- House for Rent
337 Barnes Rd Ob526, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al fresco or try a nearby bistro or 5 star restaurant----the choice is

Karen Overtoom Karen M. Overtoom R.E.

337 Barnes Rd Ob526, Oak Bluffs, MA 02557
/49
$865,000 Sold Apr 17, 2025
- 1,208 Sq Ft
- $716/SF
- 70 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
4 Quail Run Unit 17, Oak Bluffs, MA 02557

LUXURIOUS LIFESTYLE AMENITIES: RENOVATED TOWNHOUSE WITH TENNIS, PICKLEBALL + BOATING ACCESS. Welcome to this beautifully renovated 2-bedroom, 2-bathroom townhouse located in the exclusive Sengekontacket community. This nicely appointed property offers a perfect blend of comfort and convenience, making it an ideal choice for year-round living or as a rental investment opportunity.Spanning 1,208

Wendy Harman Compass | Point B

4 Quail Run Unit 17, Oak Bluffs, MA 02557

/11
Est $1,008,648 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,120 Sq Ft
7 Richmond Ave, Oak Bluffs, MA 02568

7 Richmond Ave, Oak Bluffs, MA 02568

/21
$3,100,000
- 3 Beds
- 1 Bath
- 1 Sq Ft
23 Circuit Avenue Extension, Oak Bluffs, MA 02557

Rare Opportunity with Endless Possibilities - Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound--a setting that captures the very

Rene Ben David Ocean Park Realty, Inc.

23 Circuit Avenue Extension, Oak Bluffs, MA 02557
/8
$12,000 per month
- 3 Beds
- 1.5 Baths
- 820 Sq Ft
- House for Rent
8 Beach Plum Path Ob525, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. This irresistible home is a 3-minute walk away from a deeded, sandy, sheltered beach and only a 5-minute drive to the center of Oak Bluffs and all the fun activities that Circuit Avenue has to offer. The casual getaway has wonderful ambiance enhanced by its soaring ceilings, a wood-burning fireplace, and delightful furnishings.

Karen Overtoom Karen M. Overtoom R.E.

8 Beach Plum Path Ob525, Oak Bluffs, MA 02557
/42
$865,000 Sold Apr 17, 2025
- 1,208 Sq Ft
- $716/SF
- 2 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
4 Quail Run Rd Unit 17, Edgartown, MA 02539

Luxurious Lifestyle Amenities: Renovated Townhouse With Tennis, Pickleball + Boating Access - This nicely appointed condominium in the exclusive Sengekontacket community offers a perfect blend of comfort and convenience. It features two walls of sliding glass doors that lead out to an expansive 288-square foot deck. The property was updated in 2023 with new Pella® sliding glass doors, new

Wendy Harman Compass

4 Quail Run Rd Unit 17, Edgartown, MA 02539

/6
Not Listed For Sale
5 Tori Ln, Oak Bluffs, MA 02568

5 Tori Ln, Oak Bluffs, MA 02568

/37
$1,995,000
- 4 Beds
- 3 Baths
- 3,058 Sq Ft
2 Farm Path, Oak Bluffs, MA 02557

"Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

Sean Federowicz Landmarks at TODAY Real Estate

2 Farm Path, Oak Bluffs, MA 02557
/14
$640,000 Sold Apr 11, 2025
- 647 Sq Ft
- $989/SF
- 178 Days On Market
- 2 Beds
- 1 Bath
- Built 1880
56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557

OAK BLUFFS REAL ESTATE OPPORTUNITY~Explore this spacious first-floor condo, complete with two bedrooms and a full bath. Perfectly located just a leisurely stroll from the beach, a variety of restaurants, charming campgrounds, coffee shops, and the harbor with ferry access. Boasting coveted B1 zoning, this property offers an outstanding opportunity for savvy investors. Its potential as a rental

Marilyn Moses Ocean Park Realty Inc

56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557

/28
Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,754 Sq Ft
40 Hidden Cove Rd Unit 7, Oak Bluffs, MA 02557

40 Hidden Cove Rd Unit 7, Oak Bluffs, MA 02557

/24
$1,699,000
- 2 Beds
- 1 Bath
- 826 Sq Ft
66 Brush Pond Rd, Oak Bluffs, MA 02557

**Charming Vineyard Waterfront Cottage in Oak Bluffs**Nestled in a peaceful cul-de-sac in Oak Bluffs, this newly renovated 2-bedroom, 1-bathroom cottage offers the perfect blend of traditional Vineyard charm and modern sensibility. With stunning panoramic views of Brush Pond, the Lagoon, and the iconic Drawbridge, this cozy retreat provides the ultimate setting for both relaxation and outdoor

Michael Schweikert Ocean Park Realty Inc

66 Brush Pond Rd, Oak Bluffs, MA 02557

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