Gosnold, MA Homes

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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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  /8

  $4,800 total monthly price

  • 3 Beds
  • 3 Baths
  • 3,279 Sq Ft
  • House for Rent

  165 Christiantown Rd, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

  Karen Overtoom Karen M. Overtoom R.E.

  165 Christiantown Rd, West Tisbury, MA 02575
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  /9

  $1,500,000 Sold Oct 20, 2025

  49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

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

  Last Sold Summary

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

  49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
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  /30

  Est $2,846,212 Not Listed For Sale

  • 3 Beds
  • 5 Baths
  • 2,926 Sq Ft

  23 Alex Way, Vineyard Haven, MA 02568

  23 Alex Way, Vineyard Haven, MA 02568
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  /37

  $1,495,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 5,384 Sq Ft

  24 White Alder Way, South Dartmouth, MA 02748

  Set on a picturesque 1.79-acre lot just minutes from Padanaram and Russells Mills Villages, this custom shingled residence offers a spacious layout designed for easy living and effortless entertaining. Inside, a welcoming entry foyer opens to an airy living room w/ vaulted ceilings and a gas fireplace. The well-appointed kitchen—anchored by a granite-topped island—connects to the fireplaced

  Team MCM Gibson Sotheby's International Realty

  24 White Alder Way, South Dartmouth, MA 02748
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  /8

  $8,000 total monthly price

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

  56 Chilmark Rd, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master

  Karen Overtoom Karen M. Overtoom R.E.

  56 Chilmark Rd, Chilmark, MA 02535
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  /13

  $2,237,500 Sold Nov 19, 2025

  26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

  • 4 Beds
  • 3 Baths
  • 2,299 Sq Ft
  • Built 1974

  Last Sold Summary

  • 16% Below List Price
  • $973/SF
  • 120 Days On Market

  Last Listing Agent Jill Napior Tea Lane Associates

  26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
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  /20

  Est $1,352,776 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft

  225 Longview Rd, Vineyard Haven, MA 02568

  225 Longview Rd, Vineyard Haven, MA 02568
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  /42

  $1,525,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,029 Sq Ft

  54 Whitman Rd, Woods Hole, MA 02543

  First time offered since 1957, this 1924 Woods Hole classic is a rare opportunity to create your Cape Cod retreat in Gansett Woods. Set in a serene setting w/ deeded rights to Gansett beach, the home is filled w/ timeless charm, original details including built-ins & a warm sense of history. The thoughtful layout offers both gathering spaces & quiet corners, making it ideal for summer escapes or

  Irene O'Connell Sotheby's International Realty

  54 Whitman Rd, Woods Hole, MA 02543
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  /42

  $19,000 total monthly price

  • 6 Beds
  • 6.5 Baths
  • 6,950 Sq Ft
  • House for Rent

  40 Sweet William Way, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

  Karen Overtoom Karen M. Overtoom R.E.

  40 Sweet William Way, West Tisbury, MA 02575
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  /3

  $1,695,000 Sold May 30, 2025

  5 Vincent Rd, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1960

  Last Sold Summary

  • $1,308/SF

  Current Estimated Value $1,383,450

  Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

  5 Vincent Rd, Vineyard Haven, MA 02568
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  /2

  Est $2,389,558 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,269 Sq Ft

  59 Field View Ln, Vineyard Haven, MA 02568

  59 Field View Ln, Vineyard Haven, MA 02568
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  /15

  $1,495,000

  • Land
  • 3.01 Acres
  • $496,678 per Acre

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568

  Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is situated in an area of several multimillion-dollar homes and will accommodate a house, a guesthouse, and a

  Cassie Courtney Wallace & Co. Sotheby's

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568
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  /26

  $50,700 total monthly price

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft
  • House for Rent

  6 Trails End Ch241, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

  Karen Overtoom Karen M. Overtoom R.E.

  6 Trails End Ch241, Chilmark, MA 02535
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  /4

  $1,100,000 Sold Feb 10, 2025

  255 Jordan Rd, South Dartmouth, MA 02748

  • Land
  • 4.35 Acres
  • $252,874 per Acre

  Last Sold Summary

  • 37% Below List Price
  • 95 Days On Market

  Current Estimated Value $933,911

  Last Listing Agent The Mathew J Arruda Group Compass

  255 Jordan Rd, South Dartmouth, MA 02748
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  /13

  Est $4,498,963 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  144 Pond View Farm Rd, Vineyard Haven, MA 02568

  144 Pond View Farm Rd, Vineyard Haven, MA 02568
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  /50

  $1,900,000

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  20 Brook Hollow Rd, Vineyard Haven, MA 02568

  This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

  Jim Feiner Feiner Real Estate

  20 Brook Hollow Rd, Vineyard Haven, MA 02568
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  /3

  $13,200 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • House for Rent

  224 N Rd Ch248, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

  Karen Overtoom Karen M. Overtoom R.E.

  224 N Rd Ch248, Chilmark, MA 02535
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  /2

  $1,500,000 Sold Aug 13, 2025

  82 Christiantown Rd Unit R, West Tisbury, MA 02575

  • Land
  • 7.42 Acres
  • $202,156 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  82 Christiantown Rd Unit R, West Tisbury, MA 02575
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  /42

  Est $1,939,115 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 2,172 Sq Ft

  44 Music St, Vineyard Haven, MA 02568

  44 Music St, Vineyard Haven, MA 02568
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  /4

  $1,449,000 Pending

  • Land
  • 3.9 Acres
  • $371,538 per Acre

  34 Ebens Ln, Chilmark, MA 02535

  Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetables, and/or arbors. The land may also be used for grazing and housing livestock along with any

  Thomas Wallace Wallace & Co. Sotheby's

  34 Ebens Ln, Chilmark, MA 02535
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  /20

  $16,800 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft
  • House for Rent

  31 S Ridge Rd Ch218, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

  Karen Overtoom Karen M. Overtoom R.E.

  31 S Ridge Rd Ch218, Chilmark, MA 02535
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  /46

  $790,525 Sold Oct 14, 2025

  9 James St, Woods Hole, MA 02543

  • 4 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Above List Price
  • $465/SF
  • 18 Days On Market

  Last Listing Agent Dennis Murphy Weichert, Realtors-Donahue Partners

  9 James St, Woods Hole, MA 02543
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  /23

  Est $2,085,280 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,370 Sq Ft

  50 Campbell Rd, Vineyard Haven, MA 02568

  50 Campbell Rd, Vineyard Haven, MA 02568
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  /2

  $799,000

  • Land
  • 0.92 Acre
  • $870,181 per Acre

  22 Bramble Path Unit 214, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path Unit 214, West Tisbury, MA 02568
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  /35

  $22,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,290 Sq Ft
  • House for Rent

  36 Henry Hough Lane Ch206, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

  Karen Overtoom Karen M. Overtoom R.E.

  36 Henry Hough Lane Ch206, Chilmark, MA 02535
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  /42

  $2,900,000 Sold Jul 03, 2025

  67 Hidden Village Rd, Vineyard Haven, MA 02568

  • 7 Beds
  • 5.5 Baths
  • 4,476 Sq Ft
  • Built 1997

  Last Sold Summary

  • 24% Below List Price
  • $648/SF
  • 347 Days On Market

  Last Listing Agent Stephanie Roache Donnelly + Co.

  67 Hidden Village Rd, Vineyard Haven, MA 02568
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  /6

  Est $2,980,493 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,935 Sq Ft

  71 Runner Rd, Vineyard Haven, MA 02568

  71 Runner Rd, Vineyard Haven, MA 02568
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  /45

  $19,500,000

  • 7 Beds
  • 5.5 Baths
  • 3,344 Sq Ft

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535

  This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below.

  Thomas Leclair Landvest MV

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535
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  /32

  $36,000 total monthly price

  • 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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  /28

  $1,400,000 Sold Nov 26, 2025

  5 Scottys Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft
  • Built 1968

  Last Sold Summary

  • 22% Below List Price
  • $879/SF
  • 126 Days On Market

  Last Listing Agent Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  5 Scottys Ln, Vineyard Haven, MA 02568
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  /31

  Est $1,312,470 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 855 Sq Ft

  16 Elias Ln, Vineyard Haven, MA 02568

  16 Elias Ln, Vineyard Haven, MA 02568
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  /39

  $950,000

  • 2 Beds
  • 2 Baths
  • 1,706 Sq Ft

  48 N Shore Dr Unit 8, South Dartmouth, MA 02748

  Enjoy the sweeping panoramic views of Buzzards Bay & the Elizabeth Islands. This home is a rare find in the exclusive guard-gated Community of Round Hill. This Mansion second floor suite could be your year-round home or a summer retreat offering two bedrooms and two full baths. Within the open-concept dining/living room featuring a dramatic original marble fireplace living room, soaring ceilings,

  Fatima Simas Anne Whiting Real Estate

  48 N Shore Dr Unit 8, South Dartmouth, MA 02748
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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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  /11

  $749,000 Sold Apr 14, 2025

  488 Lighthouse Rd, Aquinnah, MA 02535

  • 1 Bed
  • 0.5 Baths
  • 240 Sq Ft
  • Built 1980

  Last Sold Summary

  • $3,121/SF
  • 0 Days On Market

  Current Estimated Value $1,057,679

  Last Listing Agent Meg Bodnar Tea Lane Associates

  488 Lighthouse Rd, Aquinnah, MA 02535
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  /26

  Est $1,051,339 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,182 Sq Ft

  4 Elias Ln, Vineyard Haven, MA 02568

  4 Elias Ln, Vineyard Haven, MA 02568
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  /34

  $4,950,000

  • 5 Beds
  • 4.5 Baths
  • 3,413 Sq Ft

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
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  /8

  $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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  /21

  $1,325,000 Sold Aug 29, 2025

  19 S Vine Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,982 Sq Ft
  • Built 1992

  Last Sold Summary

  • 17% Below List Price
  • $669/SF
  • 89 Days On Market

  Current Estimated Value $1,402,208

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

  19 S Vine Ln, Vineyard Haven, MA 02568
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  /26

  Est $4,921,862 Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 4,800 Sq Ft

  48 Forest Rd, Vineyard Haven, MA 02568

  48 Forest Rd, Vineyard Haven, MA 02568

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