Dukes County, MA Homes

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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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  $18,000 total monthly price

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

  Karen Overtoom Karen M. Overtoom R.E.

  71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
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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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  Est $1,488,093 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

  Last Listing Agent Elise Ryan LandVest MV
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  $1,299,000

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  9 Galway Rd, Vineyard Haven, MA 02568

  Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

  Julianna Flanders Flanders Real Estate

  9 Galway Rd, Vineyard Haven, MA 02568
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  $36,000 total monthly price

  • 3 Beds
  • 3 Baths
  • 2,556 Sq Ft
  • House for Rent

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The kitchen has granite countertops,

  Karen Overtoom Karen M. Overtoom R.E.

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539
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  $1,675,000 Sold Apr 04, 2025

  7 N Bog Rd, Edgartown, MA 02539

  • 3 Beds
  • 3 Baths
  • 2,094 Sq Ft
  • Built 1994

  Last Sold Summary

  • 27% Below List Price
  • $800/SF
  • 276 Days On Market

  Last Listing Agent Robin Perschel Feiner Real Estate

  7 N Bog Rd, 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

  Last Listing Agent Frank Markwica Sandpiper Realty Inc
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  /31

  $12,500,000 Pending

  • 6 Beds
  • 4 Baths
  • 4,876 Sq Ft

  44 Forest Rd, Vineyard Haven, MA 02568

  Quintessential Seven Gates waterfront compound offering outstanding views and immediate beachfront access. This exceptional Martha’s Vineyard retreat includes a main residence and barn, thoughtfully designed and built by South Mountain Company. Immaculately maintained, both structures are virtually turn-key.The interiors showcase rich detail, the highest level of craftsmanship, and elegant

  Bill Rossi Studio Realty

  44 Forest Rd, Vineyard Haven, MA 02568
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  $29,300 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 1,871 Sq Ft
  • House for Rent

  76 Mattakesett Way Ed313, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while lazing on the porch swing.The

  Karen Overtoom Karen M. Overtoom R.E.

  76 Mattakesett Way Ed313, Edgartown, MA 02539
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  /2

  $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 $964,646

  Last Listing Agent LINK Email Cache LINK

  5 Johns Way, Oak Bluffs, MA 02557
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  /31

  Est $1,389,111 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

  • 23% Above List Price
  • $565/SF
  • 25 Days On Market

  Last Sold Price $1,130,000

  Last Listing Agent Jennifer B. DaSilva Compass
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  $2,850,000

  • Land
  • 1.52 Acres
  • $1,881,064 per Acre

  39 Slough Cove Rd Unit 12.2 (part of), Edgartown, MA 02539

  NEWLY LISTED | Build Your Katama Dream. Set in one of Martha’s Vineyard’s most sought-after locations, this newly created 1.5-acre parcel offers a rare opportunity to build your custom island retreat in the heart of Katama. Perfectly sited near the pristine shores of South Beach, the level and conforming R60 lot provides endless potential for a main residence and an outdoor oasis designed to your

  Fran Agnoli The Agency

  39 Slough Cove Rd Unit 12.2 (part of), Edgartown, MA 02539
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  $11,000 total monthly price

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

  15 Price's Way Ed322, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The

  Karen Overtoom Karen M. Overtoom R.E.

  15 Price's Way Ed322, Edgartown, MA 02539
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  $1,100,000 Sold Jun 17, 2025

  17 Front St, Oak Bluffs, MA 02557

  • 2 Beds
  • 2 Baths
  • 2,912 Sq Ft
  • Built 1989

  Last Sold Summary

  • $378/SF
  • 0 Days On Market

  Current Estimated Value $1,174,686

  Last Listing Agent LINK Email Cache LINK

  17 Front St, Oak Bluffs, MA 02557
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  Est $1,515,783 Not Listed For Sale

  13 Saddle Club Rd, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 2,717 Sq Ft
  • Built 1988

  13 Saddle Club Rd, Edgartown, MA 02539

  Last Sold Summary

  • 21% Above List Price
  • $460/SF
  • 43 Days On Market

  Last Sold Price $1,250,000

  Last Listing Agent Reciprocal Agent Reciprocal Office
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  /5

  $3,895,000 Under Contract

  • Land
  • 0.53 Acre
  • $7,349,057 per Acre

  44 Plantingfield Way Unit 2, Edgartown, MA 02539

  PRIME 0.5-ACRE BUILDING OPPORTUNITY WITH GRANDFATHERED GUEST HOUSE RIGHTS - Exceptional half-acre parcel offering a rare opportunity in a highly desirable location. This level, expansive lot provides an ideal foundation for a custom home, supported by ample frontage, favorable topography, and strong surrounding property values. A key advantage of this property is its grandfathered right to

  David Dickinson Compass | Point B

  44 Plantingfield Way Unit 2, Edgartown, MA 02539
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  $80,000 total monthly price

  • 4 Beds
  • 4.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $20,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Gorgeous new 4 bedroom 4 bath home. Top of the line finishes and appliances. Gourmet kitchen, screened in porch with fireplace and TV. Pool with swim up bar, hot tub and grilling area. This is a cream of the crop Katama house is a short distance to downtown Edgartown and

  Karen Overtoom Karen M. Overtoom R.E.

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539
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  $1,100,000 Sold Oct 29, 2025

  11 Quammox Rd, Edgartown, MA 02539

  • 2 Beds
  • 1 Bath
  • 685 Sq Ft
  • Built 1940

  Last Sold Summary

  • $1,606/SF
  • 0 Days On Market

  Current Estimated Value $1,201,275

  Last Listing Agent LINK Email Cache LINK

  11 Quammox Rd, Edgartown, MA 02539
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  /20

  Est $1,768,635 Not Listed For Sale

  11 Pine Tree Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 1,240 Sq Ft
  • Built 1960

  11 Pine Tree Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Above List Price
  • $1,371/SF
  • 74 Days On Market

  Last Sold Price $1,700,000

  Last Listing Agent Carol Shore Donnelly + Co.
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  $1,875,000

  • Land
  • 0.56 Acre
  • $3,348,214 per Acre

  11A Duarte Cir, Edgartown, MA 02539

  Nestled in the HEART OF KATAMA, this ready-to-build unique deep lot offers the opportunity to create your DREAM COMPOUND just minutes to Edgartown Center & South Beach. Set back on a pristine cul-de-sac this property provides unparalleled privacy for a home in Katama with a country vibe. The SIX BEDROOM COMPOUND allows a MAIN HOUSE, GUEST HOUSE, GARAGE and has amble space for outdoor entertaining

  David White OwnerEntry.com

  11A Duarte Cir, Edgartown, MA 02539
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  $38,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  17 Otis Bassett Rd, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

  Karen Overtoom Karen M. Overtoom R.E.

  17 Otis Bassett Rd, West Tisbury, MA 02575
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  $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
  • 33 Days On Market

  Current Estimated Value $1,653,553

  Last Listing Agent Hope O'Brien Compass Massachusetts, LLC

  36 Ferro Way, Tisbury, MA 02568
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  Est $926,458 Not Listed For Sale

  84 Pine Tree Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft
  • Built 1980

  84 Pine Tree Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 12% Above List Price
  • $743/SF
  • 66 Days On Market

  Last Sold Price $829,000

  Last Listing Agent Michele Moore Island Real Estate
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  $9,250,000

  • 5 Beds
  • 7 Baths
  • 4,078 Sq Ft

  1 Field Club Dr, Edgartown, MA 02539

  Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and

  Thomas Wallace Wallace & Co. Sotheby's

  1 Field Club Dr, Edgartown, MA 02539
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  $56,800 total monthly price

  • 5 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • House for Rent

  2 Nonamessett Rd, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool

  Karen Overtoom Karen M. Overtoom R.E.

  2 Nonamessett Rd, Edgartown, MA 02539
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  $1,390,000 Sold Jul 22, 2025

  57 Colonial Dr, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,299 Sq Ft
  • Built 1984

  Last Sold Summary

  • $1,070/SF
  • 0 Days On Market

  Current Estimated Value $1,079,233

  Last Listing Agent LINK Email Cache LINK

  57 Colonial Dr, Vineyard Haven, MA 02568
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  Est $1,684,820 Not Listed For Sale

  55 Pinehurst Rd, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1996

  55 Pinehurst Rd, Edgartown, MA 02539

  Last Sold Summary

  • 7% Above List Price
  • $1,250/SF
  • 15 Days On Market

  Last Sold Price $1,575,000

  Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's International Realty
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  /31

  $5,995,000

  • 3 Beds
  • 3 Baths
  • 2,234 Sq Ft

  43 Sengekontacket Rd, Oak Bluffs, MA 02557

  Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

  Peyton Wallace Studio Realty

  43 Sengekontacket Rd, Oak Bluffs, MA 02557
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  /21

  $14,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,505 Sq Ft
  • House for Rent

  175 Meetinghouse Way Ed321, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This updated contemporary is located in Katama area and a short bike ride to South Beach. There are 4 bedrooms, 1 down and 3 up, and a beautiful kitchen/dining which opens to a large living room. The house has a nice deck on the front and owners have added a deck off the

  Karen Overtoom Karen M. Overtoom R.E.

  175 Meetinghouse Way Ed321, Edgartown, MA 02539
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  $1,050,000 Sold Oct 06, 2025

  4 Quail Run Unit 2, Oak Bluffs, MA 02557

  • 2 Beds
  • 1.5 Baths
  • 1,323 Sq Ft
  • Built 1972

  Last Sold Summary

  • 11% Below List Price
  • $794/SF
  • 62 Days On Market

  Current Estimated Value $1,017,904

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  4 Quail Run Unit 2, Oak Bluffs, MA 02557
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  Est $1,212,287 Not Listed For Sale

  31 Music St, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1817

  31 Music St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 8% Above List Price
  • $978/SF
  • 0 Days On Market

  Last Sold Price $1,125,000

  Last Listing Agent LINK Email Cache LINK
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  $1,395,000

  • 0.5 Baths
  • 1,283 Sq Ft

  4 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers

  Jarrett Hurwitz Keller Williams Realty

  4 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  $100,000 total monthly price

  • 5 Beds
  • 4 Baths
  • 4,500 Sq Ft
  • House for Rent

  60 Witchwood Lane Ed317, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $25,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gorgeous waterfront home is well equipped with gourmet kitchen, stone fireplace, numerous sitting areas, and multiple decks each with water views over the Edgartown Harbor. Both the main and upper level have beautiful master suites and also washers & dryers. Easy

  Karen Overtoom Karen M. Overtoom R.E.

  60 Witchwood Lane Ed317, Edgartown, MA 02539
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  $5,250,000 Sold Jul 02, 2025

  14 Katama Farm Rd N, Edgartown, MA 02539

  • 3 Beds
  • 4.5 Baths
  • 2,869 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $1,830/SF
  • 54 Days On Market

  Last Listing Agent Courtney Marek Sandpiper Realty Inc

  14 Katama Farm Rd N, Edgartown, MA 02539
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  Not Listed For Sale

  30 Mill Hill Rd, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 2,800 Sq Ft
  • Built 1850

  30 Mill Hill Rd, Edgartown, MA 02539

  Last Sold Summary

  • $1,784/SF
  • 4 Days On Market

  Last Sold Price $4,995,000

  Last Listing Agent Wendy Harman Compass
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  /29

  $10,950,000

  • 4 Beds
  • 3.5 Baths
  • 2,050 Sq Ft

  16 Shotnaigher Ln, Chilmark, MA 02535

  New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet

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

  16 Shotnaigher Ln, Chilmark, MA 02535
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  /26

  $50,000 total monthly price

  • 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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  /2

  $1,555,000 Sold Apr 14, 2025

  7 Clark Dr, Edgartown, MA 02539

  • Land
  • 0.36 Acre
  • $4,349,650 per Acre

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $3,741,926

  Last Listing Agent LINK Email Cache LINK

  7 Clark Dr, Edgartown, MA 02539
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  Est $1,329,974 Not Listed For Sale

  165 Weaver Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1974

  165 Weaver Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 9% Above List Price
  • $815/SF
  • 43 Days On Market

  Last Sold Price $1,225,000

  Last Listing Agent John Best John Best Associates

Showing Results 241 - 280, Page 7 of 18