Martha's Vineyard, MA Homes

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  $1,495,000 Open Fri 11AM - 1PM

  • 3 Beds
  • 4 Baths
  • 2,304 Sq Ft

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 3/4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space. with half bath. Open kitchen, dining & entertainment area. Large side deck. Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary bedroom with cathedral

  Stephanie Burke Portfolio Properties

  33 Alyssa Ln, Vineyard Haven, MA 02568
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  /29

  $64,000 total monthly price

  • 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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  /42

  $15,725,000 Sold Oct 22, 2025

  • 3,606 Sq Ft
  • $4,361/SF
  • 41 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1850

  111 N Water St, Edgartown, MA 02539

  Historic captain’s home circa 1850, brilliantly renovated by architect Patrick Ahearn in 2002, on coveted North Water Street. Enjoy sweeping 180 Edgartown Harbor views from bright, sunlit living spaces with heart pine floors and custom millwork. An open-concept first floor flows to an 18x29' mahogany deck, perfect for al fresco dining and entertaining. The rare double-wide lot offers a lawn

  Wendy Harman Compass

  111 N Water St, Edgartown, MA 02539
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  /36

  Est $2,466,989 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,791 Sq Ft

  225 Great Plains Rd, Vineyard Haven, MA 02568

  225 Great Plains Rd, Vineyard Haven, MA 02568
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  /21

  $2,725,000

  • Land
  • 7.6 Acres
  • $358,553 per Acre

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

  This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

  Peyton Wallace Studio Realty

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
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  /20

  $20,000 total monthly price

  • 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

  $3,067,050 Sold Oct 22, 2025

  • 1,872 Sq Ft
  • $1,638/SF
  • 0 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1985

  114 Park, Oak Bluffs, MA 02557

  Not Listed in LINK

  LINK Email Cache LINK

  114 Park, Oak Bluffs, MA 02557
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  /39

  Est $7,234,025 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 6,546 Sq Ft

  103 Main St, Vineyard Haven, MA 02568

  103 Main St, Vineyard Haven, MA 02568
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  /7

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,324 Sq Ft

  76 Norton Orchard Rd, Edgartown, MA 02539

  Located in the hot new area of downtown where new construction and renovation of older homes is making this the most desirable area of in-town. It is a sleepy quiet area near Edgartown Golf Course that still allows you to walk to shops, restaurants, pharmacy, grocery store, library and conservation trails. Come see why this home on town sewer and town water is best value in the Village today.

  Jim Joyce Carroll & Vincent R.E.

  76 Norton Orchard Rd, Edgartown, MA 02539
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  /29

  $34,000 total monthly price

  • 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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  /2

  $1,700,000 Sold Oct 20, 2025

  • 1,803 Sq Ft
  • $943/SF
  • 0 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1982

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  Not Listed in LINK

  LINK Email Cache LINK

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  Est $1,535,030 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  84 Christiantown Rd, Vineyard Haven, MA 02568

  84 Christiantown Rd, Vineyard Haven, MA 02568
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  /12

  $1,495,000 Open Fri 11AM - 1PM

  • 3 Beds
  • 4 Baths
  • 2,304 Sq Ft

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 3/4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

  Stephanie Burke Portfolio Real Estate, Inc.

  33 Alyssa Ln, Vineyard Haven, MA 02568
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  /25

  $24,000 total monthly price

  • 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 decor 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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  $1,500,000 Sold Oct 20, 2025

  • Land
  • 3.9 Acres
  • $384,615 per Acre

  49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

  3.9-acre parcel in a very distinguished Chilmark neighborhood. The property comes with deeded access to Tisbury Great Pond via the boat landing just 1/3 of a mile away. From there the Atlantic Ocean is just a boat ride away.

  Mark Jenkins Wallace & Co. Sotheby's

  49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
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  Est $1,802,511 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,046 Sq Ft

  8 Harpoon Hollow, Aquinnah, MA 02535

  8 Harpoon Hollow, Aquinnah, MA 02535
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  $2,100,000

  • 3 Beds
  • 3.5 Baths
  • 2,019 Sq Ft

  2 Hope's Way, Oak Bluffs, MA 02557

  ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start building your ISLAND DREAM 3 BR 3.5 home today! Purchase lot ($700,000)& Execute a BUILDING CONTRACT ($1,400,000 )or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty

  Marilyn Moses Ocean Park Realty Inc

  2 Hope's Way, Oak Bluffs, MA 02557
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  $20,000 total monthly price

  • 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

  $4,850,000 Sold Oct 20, 2025

  • 2,955 Sq Ft
  • $1,641/SF
  • 0 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2008

  46 High St, Edgartown, MA 02539

  Historic Edgartown Village Meets Modern Coastal Living Tucked along one of Edgartown’s most storied streets, 46 High Street blends timeless New England architecture with thoughtful modern updates, creating an inviting Village retreat moments from Main Street, the harbor, and iconic Lighthouse Beach. Set on a beautifully landscaped lot, the home captures the charm of its surroundings with classic

  Paul Pertile The Agency

  46 High St, Edgartown, MA 02539
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  /30

  Est $2,380,775 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft

  10 Gerts Way, Edgartown, MA 02539

  10 Gerts Way, Edgartown, MA 02539
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  /4

  $1,100,000

  • Land
  • 1 Acre
  • $1,100,000 per Acre

  25 Coffins Field Rd, Edgartown, MA 02539

  3 bedroom or 1 bedroom per 15,000 sq ft whichever is greater

  Casandra Hyland Landmarks at TODAY Real Estate

  25 Coffins Field Rd, Edgartown, MA 02539
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  $14,200 total monthly price

  • 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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  $475,000 Sold Oct 20, 2025

  • Land
  • 0 Acre

  • 11 Days On Market

  0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535

  Spectacular beach lot at Quansoo. This is the ultimate amenity. Ownership provides access to one of the most stunning beaches on the entire eastern seaboard. On one side is the majestic Atlantic Ocean and on the other the calm waters of Tisbury Great Pond where kids can catch crabs and play safely as you watch. Skip the lines and crowds at other beaches - come and go as you please for sun, sand,

  Mark Jenkins Wallace & Co. Sotheby's

  0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
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  /29

  Est $1,859,301 Not Listed For Sale

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

  165 W Tisbury Rd, Edgartown, MA 02539

  165 W Tisbury Rd, Edgartown, MA 02539
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  /13

  $1,100,000 Open Thu 11AM - 1PM

  • Land
  • 1 Acre
  • $1,100,000 per Acre

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539

  One-Acre Lot in a Peaceful Edgartown Neighborhood. Build your island dream home on this spacious one acre lot, nestled in a quiet, centrally located Edgartown neighborhood. Enjoy the best of both worlds-a tranquil setting that's just minutes from town, beaches, and all the Vineyard's favorite spots.This 3-bedroom lot offers excellent potential. Per the Board of Health, an enhanced septic

  Casandra Hyland Landmarks at TODAY Real Estate

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539
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  $18,000 total monthly price

  • 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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  /19

  $1,330,000 Sold Oct 17, 2025

  • 1,404 Sq Ft
  • $947/SF
  • 112 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1983

  32 MacHipscat Trail, Vineyard Haven, MA 02568

  This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

  Brenda Galligan Karen M. Overtoom R.E.

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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  Est $2,202,915 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 2,705 Sq Ft

  9 Heather Trail, Vineyard Haven, MA 02568

  9 Heather Trail, Vineyard Haven, MA 02568
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  $700,000

  • Land
  • 0.26 Acre
  • $2,738,654 per Acre

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

  ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start designing and building your dream 3BR + home today! Execute a BUILDING CONTRACT or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty setting, 95 feet above Lagoon

  Marilyn Moses Ocean Park Realty Inc

  2 Hope's Way Unit 31, Oak Bluffs, MA 02557
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  /40

  $16,400 total monthly price

  • 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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  $1,550,000 Sold Oct 16, 2025

  • 1,986 Sq Ft
  • $780/SF
  • 114 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  251 State Rd, Vineyard Haven, MA 02568

  This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. Abutting Land Bank property, the charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive

  Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
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  /19

  Not Listed For Sale

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

  43 Look St, Vineyard Haven, MA 02568

  43 Look St, Vineyard Haven, MA 02568
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  /15

  $2,490,000

  • Land
  • 7.2 Acres
  • $345,833 per Acre

  3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539

  Build your dream home on the special 7.2 acre North lot 1 private wooded property with 1/2 ownership in the beautiful 4.5 acre meadow in the grand Boldwater Association(BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all

  Robert Kenney Tea Lane Associates

  3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539
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  /31

  $50,000 total monthly price

  • 5 Beds
  • 5 Baths
  • 2,975 Sq Ft
  • House for Rent

  17 Edgartown Bay Rd Ed328, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to

  Karen Overtoom Karen M. Overtoom R.E.

  17 Edgartown Bay Rd Ed328, Edgartown, MA 02539
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  /30

  $1,226,500 Sold Oct 16, 2025

  • 1,637 Sq Ft
  • $749/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  9 Grovedale Rd, Oak Bluffs, MA 02557

  Welcome to a home full of character and charm in the heart of Oak Bluffs. This 3-bedroom, 2-bathroom property offers comfortable living with a sun-filled open kitchen and dining area featuring a picturesque bay window that flows seamlessly into a warm living room centered around a welcoming fireplace. Just a short distance from the Lagoon, the setting is enhanced by mature plantings that surround

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  9 Grovedale Rd, Oak Bluffs, MA 02557
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  Est $1,824,882 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,519 Sq Ft

  2 Lexington Ave, Edgartown, MA 02539

  2 Lexington Ave, Edgartown, MA 02539
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  /15

  $2,490,000

  • Land
  • 7.08 Acres
  • $351,695 per Acre

  2 Jacob's Neck Rd Unit 2, Edgartown, MA 02539

  Build your dream home or homes on the special 7.1 acre private wooded property surrounding a beautiful 4.5 acre meadow in the grand Boldwater Association (BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all convenient to

  Robert Kenney Tea Lane Associates

  2 Jacob's Neck Rd Unit 2, Edgartown, MA 02539
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  /30

  $20,000 total monthly price

  • 4 Beds
  • 3 Baths
  • 2,226 Sq Ft
  • House for Rent

  54 Schoolhouse Road Ed330, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Perfectly located close to South Beach and Edgartown is this absolutely wonderful 3 bedroom home with a separate guest quarters that has one twin bed and one full bed, kitchenette and bath. The main house has a formal dining room right off of the kitchen, a bright sunny

  Karen Overtoom Karen M. Overtoom R.E.

  54 Schoolhouse Road Ed330, Edgartown, MA 02539
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  /26

  $1,800,000 Sold Oct 15, 2025

  • 1,913 Sq Ft
  • $941/SF
  • 128 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2020

  82 Skiff Ave, Tisbury, MA 02568

  This pristine hidden gem, recently developed home is located downtown, a short walk from shops, the lagoon, the beach, the harbor,and the MV Museum.S et back from the road, the home offers a quiet and peaceful luxury living experience. The property boasts solid hw floors, ducted heating and AC, a gas fireplace, quartz countertops, tiled baths, an open floor plan, a 1st-floor primary bedroom, 2

  Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
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  /18

  Est $1,717,310 Not Listed For Sale

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

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

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