Dukes, MA Homes

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  /8

  $695,000

  • Land
  • 0.29 Acre
  • $2,396,552 per Acre

  37 Double Ox Rd Unit 44, Oak Bluffs, MA 02557

  This is your opportunity to get in on the ground floor of what will be a stunning, new development --- Lagoon Ridge. Several homes are already in place. This beautiful, wooded parcel is located down meandering, newly paved roads, just .4 mile from Barnes Road and the Lagoon. For the outdoor enthusiast, walk and ride the numerous hiking and biking trails that traverse the abutting conservation

  Lynn Buder Sandpiper Realty

  37 Double Ox Rd Unit 44, Oak Bluffs, MA 02557
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  /22

  $3,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,703 Sq Ft
  • House for Rent

  41 Oak Lane Wt147, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

  Karen Overtoom Karen M. Overtoom R.E.

  41 Oak Lane Wt147, West Tisbury, MA 02575
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  /19

  $1,110,000 Sold May 08, 2025

  • 1,275 Sq Ft
  • $871/SF
  • 45 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  31 9th St N, Edgartown, MA 02539

  Nestled among the trees near the Sengekontacket Pond, this distinctive contemporary home offers privacy while being conveniently close to Downtown Edgartown and the picturesque trails at Felix Neck Sanctuary. Designed by architect Robert Orr, this multi-level residence showcases unique architectural details and striking angled ceilings.The main living area is bathed in natural light, surrounded

  Alyssa Halisky Wallace & Co. Sotheby's

  31 9th St N, Edgartown, MA 02539
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  /40

  Est $6,802,646 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,581 Sq Ft

  733 Main St, Vineyard Haven, MA 02568

  733 Main St, Vineyard Haven, MA 02568
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  /6

  $950,000

  • 1 Bed
  • 1 Bath
  • 534 Sq Ft

  136 W Spring St, Vineyard Haven, MA 02568

  136 Spring Street - Sited on 0.32 acres and just moments from the Tisbury School and downtown Vineyard Haven, this one bedroom, one bathroom home is serviced by a 4-bedroom septic system, allowing for immediate expansion.Note: This property is also being marketed as a compound with the abutting 4BR/2.5BA home at 128 Spring Street.

  David Dickinson Compass | Point B

  136 W Spring St, Vineyard Haven, MA 02568
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  /21

  $11,000 per month

  • 2 Beds
  • 1.5 Baths
  • 800 Sq Ft
  • House for Rent

  55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. Nestled on a quiet country lane, this charming two BR guest house will enchant you with its inviting character and custom features throughout. From the cathedral living area and newly furnished interior to the covered front porch and expansive deck, this lovely cottage has it all. Privately situated , yet convenient to the village, bike path and local

  Karen Overtoom Karen M. Overtoom R.E.

  55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575
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  /6

  $700,500 Sold May 07, 2025

  • Land
  • 0.55 Acre
  • $1,273,636 per Acre

  • 0 Days On Market

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539

  Level building lot ready for your new home ideas. Area of well cared for homes both year round and seasonal use. Bike path at end of street allows easy travel to all down island towns. Ask about a new home package or work with your own builder. Perc test has been done and confirmed it is a 4 bedroom lot with a standard septic design.

  Jim Joyce Carroll & Vincent R.E.

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539
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  /17

  Est $1,508,587 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,503 Sq Ft

  165 Weaver Ln, Vineyard Haven, MA 02568

  165 Weaver Ln, Vineyard Haven, MA 02568
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  /11

  $575,000

  • Land
  • 0.29 Acre
  • $1,982,759 per Acre

  112 County Rd, Oak Bluffs, MA 02557

  Discover the perfect opportunity to build your dream home on this desirable parcel located at 112 County Road, Oak Bluffs. This spacious lot offers convenient access to local amenities, beaches, ferry terminals, and town attractions. With its central location and natural surroundings, this property is ideal for those seeking both privacy and convenience. Bring your vision to life on Martha’s

  Kiet Bordley Fort Hill Brokerage Group

  112 County Rd, Oak Bluffs, MA 02557
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  /22

  $10,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • House for Rent

  21 Leona Lane Wt115, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This very charming post & beam home is the perfect getaway for those who appreciate West Tisbury's rural character. The home is very nicely furnished and equipped, has a lovely, big yard, and the location, adjacent to the bike path, is central to up-Island shopping and the fantastic sandy beaches of Lambert's Cove and Long Point Reservation. There is no land line

  Karen Overtoom Karen M. Overtoom R.E.

  21 Leona Lane Wt115, West Tisbury, MA 02575
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  /15

  $975,000 Sold May 02, 2025

  • 1,056 Sq Ft
  • $923/SF
  • 55 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2018

  15 14th St N, Edgartown, MA 02539

  Great STARTER HOME in EDGARTOWN! The house itself was modular built BRAND NEW just under 7 years ago, so everything is plum, level, well insulated and updated. Featuring 2 beds and 2 baths on the first level, with a unfinished full walk-out basement and unfinished upstairs office space. Lots of room to spread out inside. Just under 1/4 acre lot near Edgartown Vineyard Haven Road, only a 5 minute

  Mike Sawyer Sawyer Realty Group

  15 14th St N, Edgartown, MA 02539
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  /21

  Est $1,621,126 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,066 Sq Ft

  23 Anthiers Way, Edgartown, MA 02539

  23 Anthiers Way, Edgartown, MA 02539
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  /54

  $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 Separately Perched 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 automobiles

  Leslie Floyd Portfolio Properties

  12 & 14 Maple Ave, Oak Bluffs, MA 02557
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  /15

  $21,000 per month

  • 6 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • House for Rent

  12 John Wesley Ave Ob519, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vintage kitchen. This is a house of distinctive "Carpenter Gothic"

  Karen Overtoom Karen M. Overtoom R.E.

  12 John Wesley Ave Ob519, Oak Bluffs, MA 02557
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  /19

  $1,095,000 Sold May 02, 2025

  • 1,945 Sq Ft
  • $563/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  31 Davis St, Vineyard Haven, MA 02568

  Ideal location within close proximity to the lagoon, post office, Steamship Authority, and all the downtown area has to offer. This cape home is perched on a hill and a great distance from the road. The features include a large living room with brick fireplace, kitchen with breakfast bar, separate dining area, first floor bedroom, study and full bathroom. The second-floor features two bedrooms,

  Sheila Morse Island Real Estate

  31 Davis St, Vineyard Haven, MA 02568
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  /17

  Est $1,082,396 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 934 Sq Ft

  10 Briarwood Ln, Vineyard Haven, MA 02568

  10 Briarwood Ln, Vineyard Haven, MA 02568
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  /7

  $1,199,000

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  13 County Rd, Oak Bluffs, MA 02557

  Welcome to an inviting single-story ranch nestled in the heart of Oak Bluffs. This cozy and charming home offers a comfortable living space and is set on a generous, water view landscaped lot with mature trees and natural privacy.Inside, the home features a functional layout with a mix of wood and carpet flooring, a cozy wood-burning fireplace, and abundant natural light throughout. The

  Jennifer DaSilva Compass | Point B

  13 County Rd, Oak Bluffs, MA 02557
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  /16

  $30,000 per month

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • House for Rent

  45A Buttonwood Farm Wt121, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This stunning sanctuary offers a unique balance of simplicity and sophistication. There is a lot of room for family and friends to enjoy both indoors and out. Nestled about midway between Tisbury and West Tisbury, here you will find yourself close to two of Martha's Vineyard's town centers. Enjoy ping pong in the retro style game room or a fire in the fire pit. This

  Karen Overtoom Karen M. Overtoom R.E.

  45A Buttonwood Farm Wt121, West Tisbury, MA 02575
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  /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
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  /34

  Est $1,241,357 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  38 Lake St, Vineyard Haven, MA 02568

  38 Lake St, Vineyard Haven, MA 02568
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  /44

  $6,395,000

  • 6 Beds
  • 6 Baths
  • 7,000 Sq Ft

  400 Barnes Rd, Vineyard Haven, MA 02568

  Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

  Jennifer DaSilva Compass | Point B

  400 Barnes Rd, 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
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  /13

  $2,050,000 Sold May 01, 2025

  • 1,007 Sq Ft
  • $2036/SF
  • 0 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2016

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568

  Exquisite West Tisbury Property: A Unique Opportunity.Discover the allure of a truly exceptional property nestled on 4.85 stunning acres in the serene locale of West Tisbury. This opportunity is not one to be missed, as it combines elegance, foresight, and sustainability in perfect harmony.The home is adorned with beautiful beams throughout, with nickelboard and shiplap covering the walls and

  Joe & Nicole Holland Vineyard Dream Realty LLC

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568
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  /32

  Est $2,625,554 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,276 Sq Ft

  232 Lagoon Pond Rd, Vineyard Haven, MA 02568

  232 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  /52

  $3,950,000

  • 5 Beds
  • 7 Baths
  • 4,372 Sq Ft

  139 Main St, Vineyard Haven, MA 02568

  Nestled just two blocks from Vineyard Haven’s working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses—now gracefully combined into a single half-acre parcel—this home offers rare space, privacy, and timeless character in one of the island’s most approachable villages.From the moment you step through the welcoming

  Leslie C. Floyd Portfolio Real Estate, Inc.

  139 Main St, Vineyard Haven, MA 02568
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  /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
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  /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
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  /36

  Est $1,636,556 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,144 Sq Ft

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  /8

  $3,200,000

  • Land
  • 19 Acres
  • $165,803 per Acre

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

  A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

  Jill Napior Tea Lane Associates

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
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  /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
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  /35

  $900,000 Sold Apr 30, 2025

  • 1,092 Sq Ft
  • $824/SF
  • 1 Day On Market

  • 1 Bed
  • 1.5 Baths
  • Built 2008

  53 Anthiers Way, Edgartown, MA 02539

  This unique and beautifully handcrafted home in Edgartown is a rare find. It features 1 bedroom, 1.5 bathrooms, and a 3-bedroom septic system, offering the potential for additional bedrooms with town approval. The custom woodwork and fireplace create a warm and inviting atmosphere, while the open-concept kitchen and dining area showcase handmade wood countertops and rustic charm--making it the

  Valentina Globa eXp Realty, LLC

  53 Anthiers Way, Edgartown, MA 02539
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  /77

  Est $1,009,862 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  14 Cottage St, Vineyard Haven, MA 02568

  14 Cottage St, Vineyard Haven, MA 02568
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  /31

  $1,350,000

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft

  145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

  Enjoy effortless island living in this beautifully renovated 3-bedroom, 2.5-bath condo, tucked within a quiet and well-maintained association. Thoughtfully updated with modern finishes and quality craftsmanship, this spacious unit offers comfort, style, and functionality. The open-concept living area features a cozy wood pellet fireplace, perfect for cooler evenings, and flows seamlessly into a

  Emily Flake Viewpoints

  145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568
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  /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
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  /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
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  /39

  Est $1,655,856 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft

  68 Tower Ln, Edgartown, MA 02539

  68 Tower Ln, Edgartown, MA 02539
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  /21

  $1,675,000

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  111 Charles Neck Way, Vineyard Haven, MA 02568

  Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

  Emma Kennedy Sandpiper Realty Inc

  111 Charles Neck Way, Vineyard Haven, MA 02568
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  /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
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  /35

  $1,837,500 Sold Apr 18, 2025

  • 1,654 Sq Ft
  • $1111/SF
  • 182 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  55 Charles Neck Way, Vineyard Haven, MA 02568

  LONG POINT BEACH RETREAT. Privately set on 1.6 acres in the highly-coveted Long Point area of West Tisbury, this reverse style beach house is an idyllic island retreat. The open-designed Great Room features vaulted ceilings and a wall of sliding glass doors that open out to an expansive deck, perfect for indoor-outdoor summer living and entertaining. There are also screened porches on both

  Wendy Harman Compass | Point B

  55 Charles Neck Way, Vineyard Haven, MA 02568
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  /18

  Est $1,136,676 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1 Sq Ft

  10 Canterbury Ln, Vineyard Haven, MA 02568

  10 Canterbury Ln, Vineyard Haven, MA 02568

Showing Results 161 - 200, Page 5 of 18