Vineyard Haven, MA Homes

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  /21

  $869,000

  • 1 Bed
  • 1 Bath
  • 797 Sq Ft

  37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

  In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 544-0253

  37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
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  /29

  $64,000 Per Month

  • 4 Beds
  • 7 Baths
  • 3,600 Sq Ft
  • House for Rent

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557
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  /27

  $1,070,000 Sold Apr 17, 2026

  70 Carol Ln, Oak Bluffs, MA 02557

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Built 1971

  Last Sold Summary

  • 14% Below List Price
  • $713/SF
  • 463 Days On Market

  Current Estimated Value $1,131,267

  Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

  70 Carol Ln, Oak Bluffs, MA 02557
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  /3

  Est $1,571,468 Not Listed For Sale

  18 Towanticut Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 2.5 Baths
  • 2,329 Sq Ft
  • Built 1989

  18 Towanticut Ave, Oak Bluffs, MA 02557

  Last Sold Summary

  • 5% Above List Price
  • $644/SF
  • 13 Days On Market

  • Last Sold Price $1,500,000
  • Apr 29, 2024

  Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.
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  /24

  $899,000

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

  In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 546-9282

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
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  /12

  $15,000 Per Month

  • 5 Beds
  • 6.5 Baths
  • 4,137 Sq Ft
  • House for Rent

  41 Naushon Rd Wt116, Aquinnah, MA 02575

  Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

  Karen Overtoom Karen M. Overtoom R.E.

  41 Naushon Rd Wt116, Aquinnah, MA 02575
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  /42

  $1,300,000 Sold Feb 13, 2026

  169 Clover Hill Dr, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft
  • Built 1977

  Last Sold Summary

  • 4% Below List Price
  • $719/SF
  • 9 Days On Market

  Current Estimated Value $1,337,071

  Last Listing Agent Stephanie Roache Donnelly + Co

  169 Clover Hill Dr, Vineyard Haven, MA 02568
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  /2

  Est $2,575,443 Not Listed For Sale

  28 Woodhaven Dr, Edgartown, MA 02539

  • 3 Beds
  • Built 2013

  28 Woodhaven Dr, Edgartown, MA 02539

  Last Sold Summary

  • 12% Above List Price
  • $662/SF
  • 6,292 Days On Market

  • Last Sold Price $2,300,000
  • Oct 13, 2021

  Last Listing Agent Stephanie Roache Donnelly + Co
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  /41

  $2,295,000

  • 4 Beds
  • 3.5 Baths
  • 3,016 Sq Ft

  3 Hidden Cove Rd, Oak Bluffs, MA 02557

  Hidden Cove Gem with Serene Pond Views And Coveted Water Access - Located in the desirable Hidden Cove enclave—a 65+ acre water-access community—this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The

  

  Wendy Harman

  Compass

  (508) 456-9911

  3 Hidden Cove Rd, Oak Bluffs, MA 02557
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  /20

  $20,000 Per Month

  • 3 Beds
  • 3 Baths
  • House for Rent

  40 Hidden Cove Rd, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

  Karen Overtoom Karen M. Overtoom R.E.

  40 Hidden Cove Rd, Oak Bluffs, MA 02557
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  /30

  $1,550,000 Sold Oct 16, 2025

  251 State Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,986 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $780/SF
  • 114 Days On Market

  Current Estimated Value $1,614,002

  Last Listing Agent Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
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  /10

  Not Listed For Sale

  0 Bridle Path Rd, Vineyard Haven, MA 02568

  0 Bridle Path Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 17 Days On Market

  • Last Sold Price $885,000
  • Jun 29, 2023

  Last Listing Agent Diana Gilmore Island Real Estate
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  /26

  $1,999,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,453 Sq Ft

  34 Davis St, Tisbury, MA 02568

  NEW CONSTRUCTION – Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island’s harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

  Andrew McElhinney Compass LLC

  34 Davis St, Tisbury, MA 02568
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  /26

  $50,000 Per Month

  • 4 Beds
  • 3 Baths
  • 3,237 Sq Ft
  • House for Rent

  29 Naushon Rd Wt142, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

  Karen Overtoom Karen M. Overtoom R.E.

  29 Naushon Rd Wt142, West Tisbury, MA 02575
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  $1,350,000 Sold Nov 20, 2025

  16 Majors Cove Ln, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,965 Sq Ft
  • Built 1986

  Last Sold Summary

  • 26% Below List Price
  • $687/SF
  • 156 Days On Market

  Current Estimated Value $1,436,329

  Last Listing Agent Stephanie Roache Donnelly + Co

  16 Majors Cove Ln, Edgartown, MA 02539
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  /15

  Est $1,164,649 Not Listed For Sale

  15 14th St N, Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 2018

  15 14th St N, Edgartown, MA 02539

  Last Sold Summary

  • 19% Above List Price
  • $923/SF
  • 55 Days On Market

  • Last Sold Price $975,000
  • May 02, 2025

  Last Listing Agent Mike Sawyer Sawyer Realty Group
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  /46

  $2,400,000

  • 5 Beds
  • 3.5 Baths
  • 3,873 Sq Ft

  50 Hidden Cove Rd, Edgartown, MA 02539

  Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and 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

  Sean Federowicz Landmarks at TODAY Real Estate

  50 Hidden Cove Rd, Edgartown, MA 02539
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  /22

  $20,000 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
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  /26

  $1,500,000 Sold Mar 30, 2026

  68 20th St S, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 1,975 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Below List Price
  • $759/SF
  • 28 Days On Market

  Current Estimated Value $1,598,800

  Last Listing Agent Carol Shore Donnelly + Co

  68 20th St S, Edgartown, MA 02539
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  /38

  Est $986,343 Not Listed For Sale

  287 County Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1998

  287 County Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 16% Above List Price
  • $759/SF
  • 10 Days On Market

  • Last Sold Price $850,000
  • Dec 14, 2023

  Last Listing Agent Jill Napior Tea Lane Associates
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  /41

  $1,975,000

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  33 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  33 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  /21

  $9,500 Per Month

  • 4 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • House for Rent

  155 Skiff Ave, Vineyard Haven, MA 02568

  **SUMMER RENTAL ONLY** PRICE IS WEEKLY** 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

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  155 Skiff Ave, Vineyard Haven, MA 02568
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  /2

  $1,850,000 Sold Mar 31, 2026

  7 S Meadow Ln, Oak Bluffs, MA 02557

  • 4 Beds
  • 3 Baths
  • 3,142 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Above List Price
  • $589/SF
  • 74 Days On Market

  Current Estimated Value $2,021,820

  Last Listing Agent Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  7 S Meadow Ln, Oak Bluffs, MA 02557
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  /26

  Est $1,529,549 Not Listed For Sale

  19 Quantapog Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 1,822 Sq Ft
  • Built 1988

  19 Quantapog Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 11% Above List Price
  • $757/SF
  • 177 Days On Market

  • Last Sold Price $1,380,000
  • Jan 23, 2014

  Last Listing Agent Leslie C. Floyd Portfolio Properties
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  /33

  $2,260,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,810 Sq Ft

  4 High Meadow Ln, Oak Bluffs, MA 02557

  Classic Post & Beam set in Meadow View Farms - This stunning and solidly built four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. A farmer’s porch stretches the full length of the home offering a warm welcome and a shady spot to relax overlooking the expansive front lawn. The light-filled, open first floor boasts cathedral ceilings, and

  Kate Burnside Portfolio Properties

  4 High Meadow Ln, Oak Bluffs, MA 02557
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  /25

  $24,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft
  • House for Rent

  5 Laurel Ave, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include

  Karen Overtoom Karen M. Overtoom R.E.

  5 Laurel Ave, Oak Bluffs, MA 02557
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  /27

  $1,560,000 Sold Jan 15, 2026

  36 Ferro Way, Tisbury, MA 02568

  • 5 Beds
  • 3.5 Baths
  • 4,032 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $387/SF
  • 37 Days On Market

  Current Estimated Value $1,568,044

  Last Listing Agent Hope O'Brien Compass LLC

  36 Ferro Way, Tisbury, MA 02568
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  /12

  Est $1,180,880 Not Listed For Sale

  3 Carole Ave, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,997 Sq Ft
  • Built 1985

  3 Carole Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 3% Above List Price
  • $576/SF
  • 209 Days On Market

  • Last Sold Price $1,150,000
  • Jan 30, 2024

  Last Listing Agent Bob Sparks American Real Estate LLC
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  /27

  $1,800,000

  • 3 Beds
  • 3 Baths
  • 2,293 Sq Ft

  10 Trotters Ln, West Tisbury, MA 02575

  Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

  Rebecca V Conroy Conroy & Company R.E., Inc.

  10 Trotters Ln, West Tisbury, MA 02575
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  /8

  $6,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  33 Kennebago Ave Vh414, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

  Karen Overtoom Karen M. Overtoom R.E.

  33 Kennebago Ave Vh414, Tisbury, MA 02568
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  /26

  $1,800,000 Sold Oct 15, 2025

  82 Skiff Ave, Tisbury, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 1,913 Sq Ft
  • Built 2020

  Last Sold Summary

  • 10% Below List Price
  • $941/SF
  • 128 Days On Market

  Current Estimated Value $1,678,573

  Last Listing Agent Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
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  /29

  Est $1,248,599 Not Listed For Sale

  33 Menahan St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • Built 1993

  33 Menahan St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 5% Above List Price
  • $830/SF
  • 30 Days On Market

  • Last Sold Price $1,185,000
  • Feb 18, 2021

  Last Listing Agent Katie Donahue Sandpiper Realty
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  /55

  $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 SeparatelyPerched 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

  Leslie C. Floyd Portfolio Properties

  12 & 14 Maple Ave, Oak Bluffs, MA 02557
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  /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
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  /19

  $750,000 Sold Nov 07, 2025

  41 Trinity Park, Oak Bluffs, MA 02557

  • 4 Beds
  • 1 Bath
  • 1,154 Sq Ft
  • Built 1867

  Last Sold Summary

  • 6% Below List Price
  • $650/SF
  • 14 Days On Market

  Current Estimated Value $766,507

  Last Listing Agent Stacy Ickes Donnelly + Co.

  41 Trinity Park, Oak Bluffs, MA 02557
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  /14

  Est $967,110 Not Listed For Sale

  51 Manchester Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft
  • Built 1978

  51 Manchester Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Above List Price
  • $933/SF
  • 22 Days On Market

  • Last Sold Price $955,000
  • Aug 23, 2024

  Last Listing Agent Roy Cutrer LAER Realty Partners
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  /26

  $2,600,000

  • 3 Beds
  • 1 Bath

  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

  23 Circuit Avenue Extension, Oak Bluffs, MA 02557
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  /28

  $32,000 Per Month

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  37 Mempremagog Ave Vh410, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  37 Mempremagog Ave Vh410, Tisbury, MA 02568
• 

  

  /19

  $1,110,000 Sold May 08, 2025

  31 9th St N, Edgartown, MA 02539

  • 2 Beds
  • 1.5 Baths
  • 1,275 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $871/SF
  • 45 Days On Market

  Current Estimated Value $1,121,247

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

  31 9th St N, Edgartown, MA 02539
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  Est $2,088,418 Not Listed For Sale

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 3,636 Sq Ft
  • Built 1985

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Above List Price
  • $550/SF
  • 0 Days On Market

  • Last Sold Price $2,000,000
  • May 31, 2024

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

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