Martha's Vineyard, MA Homes

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  $2,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,024 Sq Ft

  9 Hagerty Dr, Tisbury, MA 02568

  West Chop Dream Home in the Making! Experience the charm of this brand-new Shingle Style Colonial, currently under construction. Featuring 4 spacious bedrooms, 4 full and one half bath. This thoughtfully designed home offers generous space. Step outside into your private oasis, complete with an in-ground pool (36' x18') — perfect for sun-soaked afternoons and evening gatherings. Situated in a

  Lisa Gilberto C McManus Realty Group

  9 Hagerty Dr, Tisbury, MA 02568
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  $16,000 per month

  • 7 Beds
  • 3.5 Baths
  • 4,000 Sq Ft
  • House for Rent

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

  Karen Overtoom Karen M. Overtoom R.E.

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
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  $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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  Not Listed For Sale

  260 South Rd, Chilmark, MA 02535

  • 6 Beds
  • 2.5 Baths
  • 2,604 Sq Ft
  • Built 1688

  260 South Rd, Chilmark, MA 02535

  Last Sold Summary

  • $1,671/SF
  • 109 Days On Market

  • Last Sold Price $4,350,000
  • Oct 19, 2023

  Last Listing Agent Jill Napior Tea Lane Associates
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  $2,395,000

  • 4 Beds
  • 3 Baths
  • 1,918 Sq Ft

  25 Fulling Mill Rd, Chilmark, MA 02535

  Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

  Thomas Wallace Wallace & Co. Sotheby's

  25 Fulling Mill Rd, Chilmark, MA 02535
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  $3,300 per month

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft
  • House for Rent

  849 State Rd Unit 1, Aquinnah, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is

  Karen Overtoom Karen M. Overtoom R.E.

  849 State Rd Unit 1, Aquinnah, MA 02535
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  $37,500,000 Sold Oct 30, 2025

  48 Witchwood Ln, Edgartown, MA 02539

  • 9 Beds
  • 9.5 Baths
  • 16,209 Sq Ft
  • Built 2000

  Last Sold Summary

  • $2,314/SF
  • 0 Days On Market

  Last Listing Agent Gerrett Conover Landvest MV

  48 Witchwood Ln, Edgartown, MA 02539
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  Not Listed For Sale

  2 Squibnocket Rd, Chilmark, MA 02535

  • 6 Beds
  • 5.5 Baths
  • 5,808 Sq Ft
  • Built 2008

  2 Squibnocket Rd, Chilmark, MA 02535

  Last Sold Summary

  • $1,640/SF
  • 297 Days On Market

  • Last Sold Price $9,525,000
  • Apr 24, 2025

  Last Listing Agent Tina Miller Donnelly + Co
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  $2,579,000

  • 4 Beds
  • 2 Baths
  • 1,399 Sq Ft

  34 Windemere Rd, Oak Bluffs, MA 02557

  Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  34 Windemere Rd, Oak Bluffs, MA 02557
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  $7,000 per month

  • 7 Beds
  • 1.5 Baths
  • 2,900 Sq Ft
  • House for Rent

  39 N Neck Rd, Edgartown, MA 02539

  Historic Quaint Waterfront Cottage with spectacular 180 degree views of Edgartown Harbor, Oak Bluffs, Cape Cod and Cape Poge, Over 200 feet of secluded, completely private beach, The back yard abuts the fairways and club house of the ''Royal Ancient Chappaquiddick Links'' Private Golf Course. (You must pay dues to play golf), Great outdoor shower. You can see the fireworks (in 5 locations at

  Charles Petitti Coldwell Banker Realty - Newton

  39 N Neck Rd, Edgartown, MA 02539
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  $1,000,000 Sold Jan 13, 2026

  48 Edgartown - West Tisbury Rd, Edgartown, MA 02539

  • 3 Beds
  • 3 Baths
  • 1,959 Sq Ft
  • Built 1950

  Last Sold Summary

  • 29% Below List Price
  • $510/SF
  • 86 Days On Market

  Last Listing Agent Mavis Francis eXp Realty

  48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
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  Est $5,822,862 Not Listed For Sale

  100 Meetinghouse Way, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 3,193 Sq Ft
  • Built 1976

  100 Meetinghouse Way, Edgartown, MA 02539

  Last Sold Summary

  • 8% Below List Price
  • $1,988/SF
  • 5 Days On Market

  • Last Sold Price $6,349,000
  • Sep 21, 2023

  Last Listing Agent Jennifer DaSilva Compass | Point B
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  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,927 Sq Ft

  2 Bold Meadow Rd, Edgartown, MA 02539

  Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a

  Stacy Ickes Donnelly + Co.

  2 Bold Meadow Rd, Edgartown, MA 02539
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  $6,180 per month

  • 3 Beds
  • 3.5 Baths
  • 1,872 Sq Ft
  • House for Rent

  44 Music St Wt153, West Tisbury, MA 02575

  PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

  Karen Overtoom Karen M. Overtoom R.E.

  44 Music St Wt153, West Tisbury, MA 02575
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  $1,325,000 Sold Jun 30, 2025

  191 Spring Hill Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 4 Baths
  • 2,292 Sq Ft
  • Built 1992

  Last Sold Summary

  • 5% Below List Price
  • $578/SF
  • 10 Days On Market

  Current Estimated Value $1,296,533

  Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

  191 Spring Hill Rd, Vineyard Haven, MA 02568
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  Est $1,380,281 Not Listed For Sale

  45 Pine Tree Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft
  • Built 1961

  45 Pine Tree Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 12% Below List Price
  • $884/SF

  • Last Sold Price $1,237,500

  Last Listing Agent Sheila Morse Island Real Estate
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  $2,690,000

  • 6 Beds
  • 4 Baths
  • 2,618 Sq Ft

  55 Old House Way, West Tisbury, MA 02575

  Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms & 3 bathrooms in Main & 2 bedrooms & 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with stainless

  Leslie Graham Anchor Realty of Martha's Vineyard

  55 Old House Way, West Tisbury, MA 02575
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  $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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  $1,600,000 Sold Nov 07, 2025

  96 Pondview Dr, Oak Bluffs, MA 02536

  • 4 Beds
  • 2.5 Baths
  • 2,115 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $757/SF
  • 35 Days On Market

  Last Listing Agent Doug Burke Cronigs Real Estate

  96 Pondview Dr, Oak Bluffs, MA 02536
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  Est $2,288,109 Not Listed For Sale

  377 State Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 1970

  377 State Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Above List Price
  • $902/SF
  • 518 Days On Market

  • Last Sold Price $2,197,000
  • Oct 12, 2023

  Last Listing Agent Jill Napior Tea Lane Associates
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  $2,495,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  268 Tashmoo Ave, Vineyard Haven, MA 02568

  Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

  Michele Casavant Vineyard Village Realty

  268 Tashmoo Ave, Vineyard Haven, MA 02568
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  $20,000 per month

  • 4 Beds
  • 4.5 Baths
  • 2,306 Sq Ft
  • House for Rent

  3 E Pasture Ln, Aquinnah, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of your favorite hot beverage. PLEASE TAKE NOTE!!!!!THIS IS

  Karen Overtoom Karen M. Overtoom R.E.

  3 E Pasture Ln, Aquinnah, MA 02535
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  $949,000 Sold Jun 23, 2025

  345 Franklin St, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,012 Sq Ft
  • Built 1986

  Last Sold Summary

  • $938/SF
  • 49 Days On Market

  Current Estimated Value $965,478

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

  345 Franklin St, Vineyard Haven, MA 02568
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  Est $3,623,284 Not Listed For Sale

  94 Marthas Rd, Edgartown, MA 02539

  • 6 Beds
  • 4.5 Baths
  • 3,902 Sq Ft
  • Built 2009

  94 Marthas Rd, Edgartown, MA 02539

  Last Sold Summary

  • 8% Above List Price
  • $859/SF
  • 458 Days On Market

  • Last Sold Price $3,350,000
  • Mar 15, 2024

  Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's International Realty
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  $2,395,000

  • 4 Beds
  • 2.5 Baths
  • 2,760 Sq Ft

  69 Whalers Walk, Edgartown, MA 02539

  EDGARTOWN – Beautifully landscaped property set on a lovely open, cleared lot with exceptional curb appeal, located just minutes from Downtown Edgartown and South Beach. This inviting home features many updates including a Tesla Solar Roof with a Tesla Powerwall, attached to Town Sewer with a SEVEN (7) bedroom sewer connection and an approval for a Two Car Garage with a detached bedroom above.

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  69 Whalers Walk, Edgartown, MA 02539
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  $8,250 per month

  • 7 Beds
  • 5 Baths
  • 3,528 Sq Ft
  • House for Rent

  227 S Gate Rd Wt120, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

  Karen Overtoom Karen M. Overtoom R.E.

  227 S Gate Rd Wt120, West Tisbury, MA 02575
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  $1,050,000 Sold Jun 30, 2025

  160 Bernard Cir, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,606 Sq Ft
  • Built 1977

  Last Sold Summary

  • 12% Below List Price
  • $654/SF
  • 45 Days On Market

  Current Estimated Value $1,180,142

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  160 Bernard Cir, Vineyard Haven, MA 02568
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  Est $2,374,536 Not Listed For Sale

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft
  • Built 1948

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Below List Price
  • $1,447/SF
  • 0 Days On Market

  • Last Sold Price $2,398,500
  • Dec 19, 2024

  Last Listing Agent LINK Email Cache LINK
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  $3,995,000

  • 8 Beds
  • 6 Baths
  • 4,651 Sq Ft

  23 Beetle Swamp Rd, Edgartown, MA 02539

  Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you’ll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures with grazing horses.

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  23 Beetle Swamp Rd, Edgartown, MA 02539
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  $18,500 per month

  • 4 Beds
  • 3.5 Baths
  • 1,714 Sq Ft
  • House for Rent

  4 Windy Way Wt143, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

  Karen Overtoom Karen M. Overtoom R.E.

  4 Windy Way Wt143, West Tisbury, MA 02575
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  $3,695,000 Sold Nov 20, 2025

  37 Road To the Plains, Edgartown, MA 02539

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1986

  Last Sold Summary

  • $1,478/SF
  • 40 Days On Market

  Current Estimated Value $2,862,109

  Last Listing Agent Wendy Harman Compass

  37 Road To the Plains, Edgartown, MA 02539
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  Est $1,562,459 Not Listed For Sale

  39 Prices Way, Edgartown, MA 02539

  • 4 Beds
  • 2 Baths
  • 1,532 Sq Ft
  • Built 1986

  39 Prices Way, Edgartown, MA 02539

  Last Sold Summary

  • 18% Above List Price
  • $865/SF
  • 119 Days On Market

  • Last Sold Price $1,325,000
  • Aug 21, 2023

  Last Listing Agent Stephanie Roache Donnelly + Co.
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  $2,650,000 Pending

  • 7 Beds
  • 5.5 Baths
  • 4,115 Sq Ft

  357 W Tisbury Rd, Edgartown, MA 02539

  Here is the Edgartown compound you've been waiting for - a 5-bedroom main house, 2-bedroom guest house, and elevated swimming pool area located on 1.5 acres. Next door there is 25 acres of conservation land. The property is barely 2/10s of a mile to Morning Glory Farm, and just a mile and a half to the village on the bike path. The house combines island country charm with modern amenities - honey

  Bonnie Pierce Wallace & Co. Sotheby's

  357 W Tisbury Rd, Edgartown, MA 02539
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  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • House for Rent

  33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

  THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

  Karen Overtoom Karen M. Overtoom R.E.

  33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
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  $982,000 Sold Dec 19, 2025

  25 Windy Hill Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $1,002/SF
  • 10 Days On Market

  Current Estimated Value $987,608

  Last Listing Agent Rene Jackson Island Real Estate

  25 Windy Hill Rd, Oak Bluffs, MA 02557
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  Est $2,580,689 Not Listed For Sale

  30 Pond Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 2,926 Sq Ft
  • Built 2004

  30 Pond Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 17% Above List Price
  • $754/SF
  • 5 Days On Market

  • Last Sold Price $2,207,500
  • Jan 03, 2024

  Last Listing Agent Elissa Lash Tea Lane Associates
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  $2,950,000

  • 3 Beds
  • 2.5 Baths
  • 1,845 Sq Ft

  33 Ocean Ave, Oak Bluffs, MA 02557

  A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and

  Marcia Sullivan Garvey Donnelly + Co.

  33 Ocean Ave, Oak Bluffs, MA 02557
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  $19,000 per month

  • 5 Beds
  • 5 Baths
  • 3,137 Sq Ft
  • House for Rent

  19 Morse St, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all

  Karen Overtoom Karen M. Overtoom R.E.

  19 Morse St, Edgartown, MA 02539
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  $1,350,000 Sold Aug 15, 2025

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $724/SF
  • 12 Days On Market

  Last Listing Agent Lesley Heidt Sandpiper Realty Inc

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
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  Est $1,812,977 Not Listed For Sale

  179 Main St, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 1 Sq Ft
  • Built 1840

  179 Main St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 18% Above List Price
  • $1,535,625/SF
  • 14 Days On Market

  • Last Sold Price $1,535,625
  • Jul 14, 2023

  Last Listing Agent Judy Federowicz Landmarks at TODAY Real Estate

Showing Results 81 - 120, Page 3 of 18