Martha's Vineyard, MA Homes

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  $3,690,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft

  13 Plantingfield Way, Edgartown, MA 02539

  Set in the heart of Edgartown Village, this pristine Cape offers an exceptional combination of charm, comfort, and in-town convenience. Just moments from boutique shopping, acclaimed galleries, fine dining, and the scenic harbor, this four-bedroom, three-bath home captures the quintessential Vineyard lifestyle. Two entrances enhance the home’s functionality: a formal front entry leads directly to

  Stephanie Roache Donnelly + Co

  13 Plantingfield Way, Edgartown, MA 02539
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  /19

  $24,000 per month

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

  44 Flanders Ln, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

  Karen Overtoom Karen M. Overtoom R.E.

  44 Flanders Ln, Chilmark, MA 02535
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  $899,000 Sold Jul 11, 2025

  8 Rock Ave, Oak Bluffs, MA 02557

  • 3 Beds
  • 1.5 Baths
  • 955 Sq Ft
  • Built 1871

  Last Sold Summary

  • $941/SF
  • 6 Days On Market

  Current Estimated Value $921,674

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  8 Rock Ave, Oak Bluffs, MA 02557
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  Est $1,952,325 Not Listed For Sale

  165 W Tisbury Rd, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 2007

  165 W Tisbury Rd, Edgartown, MA 02539

  Last Sold Summary

  • 9% Above List Price
  • $1,019/SF
  • 37 Days On Market

  • Last Sold Price $1,783,000
  • Oct 25, 2023

  Last Listing Agent Lisa Gilberto C McManus Realty Group
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  $9,499,000

  • 4 Beds
  • 7 Baths
  • 5,902 Sq Ft

  43 Peases Point Way S, Edgartown, MA 02539

  Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown's most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  43 Peases Point Way S, Edgartown, MA 02539
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  $36,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  29 Cemetery Rd Ch216, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

  Karen Overtoom Karen M. Overtoom R.E.

  29 Cemetery Rd Ch216, Chilmark, MA 02535
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  $7,926,400 Sold Apr 28, 2025

  32 Boldwater Rd, Edgartown, MA 02539

  • 5 Beds
  • 4.5 Baths
  • 4,520 Sq Ft
  • Built 1990

  Last Sold Summary

  • 7% Below List Price
  • $1,754/SF
  • 205 Days On Market

  Last Listing Agent Robert Kenney Tea Lane Associates

  32 Boldwater Rd, Edgartown, MA 02539
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  /19

  Not Listed For Sale

  43 Look St, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 1,714 Sq Ft
  • Built 1900

  43 Look St, Vineyard Haven, MA 02568

  Last Sold Summary

  • $592/SF
  • 19 Days On Market

  • Last Sold Price $1,015,000
  • Apr 16, 2024

  Last Listing Agent Andrew McElhinney Compass LLC
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  $3,895,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  44 Plantingfield Way, Edgartown, MA 02539

  Post-and-beam style Edgartown home in a quiet, established neighborhood just minutes from downtown. This year-round home offers functional living spaces, a thoughtful layout, and generous outdoor areas ideal for relaxing or entertaining. Currently configured with a 3BR/1.5BA main house and 1BR/1BA accessory apartment over a one-car garage, this property affords multiple options for would-be

  David Dickinson Compass | Point B

  44 Plantingfield Way, Edgartown, MA 02539
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  $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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  $1,250,000 Sold Nov 12, 2025

  1054 State Rd, Vineyard Haven, MA 02568

  • 6 Beds
  • 2 Baths
  • 1,845 Sq Ft
  • Built 1881

  Last Sold Summary

  • 16% Below List Price
  • $678/SF
  • 60 Days On Market

  Current Estimated Value $1,274,063

  Last Listing Agent Stephanie Roache Donnelly + Co.

  1054 State Rd, Vineyard Haven, MA 02568
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  Est $1,935,899 Not Listed For Sale

  82 South Rd, Chilmark, MA 02535

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft
  • Built 1960

  82 South Rd, Chilmark, MA 02535

  Last Sold Summary

  • 6% Above List Price
  • $983/SF
  • 10 Days On Market

  • Last Sold Price $1,830,000
  • Dec 05, 2024

  Last Listing Agent Meg Bodnar Tea Lane Associates
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  $1,700,000

  • Land
  • 37,026 Sq Ft
  • $2,000,000 per Acre

  4 Wilson's Landing Unit 49.2, Edgartown, MA 02539

  Build your dream home in Katama just 2 miles to the parking area at South Beach, and the same distance to the heart of vibrant Edgartown village. This wooded parcel of vacant land is almost an acre in size and will support SEVEN bedrooms once tied into town sewer. Swimming pool and Accessory Dwelling Unit are allowed "by right" (certain restrictions apply to ADUs; an unrestricted 900 sq ft

  Mark Jenkins Wallace & Co. Sotheby's

  4 Wilson's Landing Unit 49.2, Edgartown, MA 02539
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  $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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  $3,750,000 Sold Oct 31, 2025

  29 Oxcart Rd, Aquinnah, MA 02535

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 2009

  Last Sold Summary

  • 11% Below List Price
  • $2,943/SF
  • 380 Days On Market

  Current Estimated Value $3,466,251

  Last Listing Agent Michelle Kelly Tea Lane Associates

  29 Oxcart Rd, Aquinnah, MA 02535
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  Est $1,774,865 Not Listed For Sale

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,461 Sq Ft
  • Built 1994

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6% Above List Price
  • $683/SF
  • 52 Days On Market

  • Last Sold Price $1,680,000
  • Oct 26, 2023

  Last Listing Agent Peyton Wallace Studio Realty
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  $599,000

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft

  124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

  MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island. At the bottom of the hill you will find

  Rene Jackson Island Real Estate

  124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
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  $34,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  15 Loon Lane Ch203, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

  Karen Overtoom Karen M. Overtoom R.E.

  15 Loon Lane Ch203, Chilmark, MA 02535
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  $15,725,000 Sold Oct 22, 2025

  111 N Water St, Edgartown, MA 02539

  • 6 Beds
  • 4.5 Baths
  • 3,606 Sq Ft
  • Built 1850

  Last Sold Summary

  • 5% Below List Price
  • $4,361/SF
  • 41 Days On Market

  Last Listing Agent Wendy Harman Compass

  111 N Water St, Edgartown, MA 02539
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  Est $1,474,820 Not Listed For Sale

  101 Dunham Ave, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 2,287 Sq Ft
  • Built 1982

  101 Dunham Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 23% Above List Price
  • $525/SF
  • 0 Days On Market

  • Last Sold Price $1,200,000
  • Jul 07, 2023

  Last Listing Agent LINK Email Cache LINK
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  $4,695,000

  • 3 Beds
  • 4 Baths
  • 2,606 Sq Ft

  95 Hines Point Rd, Vineyard Haven, MA 02568

  A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the water where you can watch sunrise over the water. A first floor

  Elissa Lash Tea Lane Associates

  95 Hines Point Rd, Vineyard Haven, MA 02568
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  $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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  $1,525,000 Sold Jun 18, 2025

  54 Lake St, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,016 Sq Ft
  • Built 1967

  Last Sold Summary

  • 12% Below List Price
  • $756/SF
  • 110 Days On Market

  Current Estimated Value $1,570,313

  Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

  54 Lake St, Vineyard Haven, MA 02568
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  Est $1,991,791 Not Listed For Sale

  83 Dolan Ave, Vineyard Haven, MA 02568

  • 5 Beds
  • 4.5 Baths
  • 3,841 Sq Ft
  • Built 1994

  83 Dolan Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6% Above List Price
  • $488/SF
  • 24 Days On Market

  • Last Sold Price $1,875,000
  • Apr 01, 2025

  Last Listing Agent Courtney Marek Sandpiper Realty
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  $1,125,000

  • Land
  • 10,097 Sq Ft
  • $4,853,322 per Acre

  15 Chapman Ln Unit 111.1, Edgartown, MA 02539

  OPPORTUNITY ABOUNDS: This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer (see notes below) creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the

  Wendy Harman Compass | Point B

  15 Chapman Ln Unit 111.1, Edgartown, MA 02539
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  $20,000 per month

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • House for Rent

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

  Karen Overtoom Karen M. Overtoom R.E.

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557
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  $4,150,000 Sold Feb 19, 2026

  97 Longview Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 5.5 Baths
  • 4,003 Sq Ft
  • Built 2008

  Last Sold Summary

  • 12% Below List Price
  • $1,037/SF
  • 74 Days On Market

  Last Listing Agent Stephanie Roache Donnelly + Co.

  97 Longview Rd, Vineyard Haven, MA 02568
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  Est $2,788,454 Not Listed For Sale

  89 Main St, Vineyard Haven, MA 02568

  • 4 Beds
  • 5 Baths
  • 2,728 Sq Ft
  • Built 1830

  89 Main St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 9% Above List Price
  • $935/SF
  • 445 Days On Market

  • Last Sold Price $2,550,000
  • Oct 29, 2024

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's International Realty
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  $14,500,000

  • 6 Beds
  • 9 Baths
  • 1,320 Sq Ft

  68 N Water St, Edgartown, MA 02539

  This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury.Just steps away from Edgartown's finest restaurants and shops, this stunning property has been completely renovated by SternMcCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details.Upon entering,

  Tom Wallace Wallace & Co. Sotheby's International Realty

  68 N Water St, Edgartown, MA 02539
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  $14,200 per month

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

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

  Karen Overtoom Karen M. Overtoom R.E.

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557
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  $665,000 Sold Mar 06, 2026

  2 Hope's Way Unit 31, Oak Bluffs, MA 02557

  • Land
  • 11,133 Sq Ft
  • $2,601,721 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 37 Days On Market

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  2 Hope's Way Unit 31, Oak Bluffs, MA 02557
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  Est $1,476,007 Not Listed For Sale

  152 Main St, Vineyard Haven, MA 02568

  • 6 Beds
  • 5.5 Baths
  • 2,417 Sq Ft
  • Built 1720

  152 Main St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 14% Above List Price
  • $538/SF
  • 370 Days On Market

  • Last Sold Price $1,300,000
  • Apr 28, 2023

  Last Listing Agent Elise Ryan LandVest MV
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  $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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  $18,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,027 Sq Ft
  • House for Rent

  12 Cottle Lane Ed341, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This four bedroom Victorian home is located close to the Edgartown Village for shopping, theater or restaurants. Walk to Fulton Street Beach. All new appliances have been added recently as well as a number of room AC units throughout the house.

  Karen Overtoom Karen M. Overtoom R.E.

  12 Cottle Lane Ed341, Edgartown, MA 02539
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  $3,350,000 Sold Jun 05, 2025

  25 Simpson's Ln, Edgartown, MA 02539

  • 6 Beds
  • 6 Baths
  • 3,156 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Below List Price
  • $1,061/SF
  • 138 Days On Market

  Last Listing Agent Greg Hartel Hartel Realty

  25 Simpson's Ln, Edgartown, MA 02539
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  Not Listed For Sale

  52 Marthas Rd, Edgartown, MA 02539

  • 3 Beds
  • 3.5 Baths
  • 3,780 Sq Ft
  • Built 1978

  52 Marthas Rd, Edgartown, MA 02539

  Last Sold Summary

  • $556/SF
  • 53 Days On Market

  • Last Sold Price $2,100,000
  • Jun 01, 2023

  Last Listing Agent Frank Markwica Sandpiper Realty Inc
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  $849,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  26 Winthrop Ave, Oak Bluffs, MA 02557

  Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  26 Winthrop Ave, Oak Bluffs, MA 02557
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  $16,400 per month

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • House for Rent

  20 Katama Bay Rd Ed350, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,100. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely Edgartown Bay Road area. This 3 bedroom newly decorated home is very close to South Beach. Easy access to town. Large grassy yard for the kids to play on.

  Karen Overtoom Karen M. Overtoom R.E.

  20 Katama Bay Rd Ed350, Edgartown, MA 02539
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  $880,000 Sold Oct 17, 2025

  5 Johns Way, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft
  • Built 1987

  Last Sold Summary

  • $645/SF
  • 0 Days On Market

  Current Estimated Value $1,034,468

  Last Listing Agent LINK Email Cache LINK

  5 Johns Way, Oak Bluffs, MA 02557
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  Est $1,415,728 Not Listed For Sale

  48 Puritan Dr, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft
  • Built 1985

  48 Puritan Dr, Vineyard Haven, MA 02568

  Last Sold Summary

  • 25% Above List Price
  • $565/SF
  • 25 Days On Market

  • Last Sold Price $1,130,000
  • Feb 27, 2024

  Last Listing Agent Jennifer B. DaSilva Compass

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