Tisbury, MA Homes

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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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  $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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  $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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  /39

  Est $6,131,941 Not Listed For Sale

  103 Main St, Vineyard Haven, MA 02568

  • 5 Beds
  • 6 Baths
  • 6,546 Sq Ft
  • Built 2008

  103 Main St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 49% Below List Price
  • $1,833/SF
  • 202 Days On Market

  Last Sold Price $12,000,000

  Last Listing Agent Tom Wallace Wallace & Co. Sotheby's International Realty
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  /7

  $475,000

  • Land
  • 0.52 Acre
  • $913,462 per Acre

  36 Boylston Dr, Edgartown, MA 02539

  Buildable lot in an established Edgartown neighborhood. Approvals are in hand for the construction of a single-family residential structure not to exceed 3 bedrooms and not to exceed 1,850 square feet of heated living area (screened porches, patios, etc are not included in this square footage). Note that this property cannot be used as a seasonal home or short-term rental. Septic plan has been

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  36 Boylston Dr, Edgartown, MA 02539
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  /21

  $8,000 total monthly price

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  10 James Pond Way, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

  Karen Overtoom Karen M. Overtoom R.E.

  10 James Pond Way, West Tisbury, MA 02575
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  $665,000 Sold Mar 06, 2026

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

  • Land
  • 0.26 Acre
  • $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 $1,565,448 Not Listed For Sale

  84 Christiantown Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 2018

  84 Christiantown Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 12% Above List Price
  • $964/SF
  • 59 Days On Market

  Last Sold Price $1,400,000

  Last Listing Agent Candy DaRosa Feiner Real Estate
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  /26

  $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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  /20

  $12,000 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,068 Sq Ft
  • House for Rent

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575

  Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

  Karen Overtoom Karen M. Overtoom R.E.

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575
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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 $964,646

  Last Listing Agent LINK Email Cache LINK

  5 Johns Way, Oak Bluffs, MA 02557
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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

  Last Listing Agent Andrew McElhinney Compass LLC
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  $5,800,000

  • 6 Beds
  • 9 Baths
  • 5,732 Sq Ft

  31 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Tashmoo Farm, one of Martha's Vineyard's iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

  31 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  /19

  $30,000 total monthly price

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

  37 Sachem Cir, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

  Karen Overtoom Karen M. Overtoom R.E.

  37 Sachem Cir, West Tisbury, MA 02575
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  /2

  $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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  /18

  Est $1,738,997 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

  • 4% Above List Price
  • $683/SF
  • 52 Days On Market

  Last Sold Price $1,680,000

  Last Listing Agent Peyton Wallace Studio 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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  $19,000 total monthly price

  • 6 Beds
  • 2.5 Baths
  • 2,155 Sq Ft
  • House for Rent

  17 Umbagog Ave Wt109, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

  Karen Overtoom Karen M. Overtoom R.E.

  17 Umbagog Ave Wt109, 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 $1,414,562 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

  • 18% Above List Price
  • $525/SF
  • 0 Days On Market

  Last Sold Price $1,200,000

  Last Listing Agent LINK Email Cache LINK
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  $2,600,000

  • 3 Beds
  • 1 Bath
  • 1,336 Sq Ft

  23 Circuit Avenue Extension, Oak Bluffs, MA 02557

  Rare Opportunity with Endless Possibilities – Unmatched Harbor & Vineyard Sound Views.Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound—a setting that captures the

  Rene Ben David Ocean Park Realty Inc

  23 Circuit Avenue Extension, Oak Bluffs, MA 02557
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  /25

  $13,600 total monthly price

  • 2 Beds
  • 2 Baths
  • 792 Sq Ft
  • House for Rent

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

  Karen Overtoom Karen M. Overtoom R.E.

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
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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 $2,693,879 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

  • 6% Above List Price
  • $935/SF
  • 445 Days On Market

  Last Sold Price $2,550,000

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's International Realty
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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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  /18

  $10,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • House for Rent

  24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

  Karen Overtoom Karen M. Overtoom R.E.

  24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
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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 $1,488,093 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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  $2,925,000

  • 5 Beds
  • 4 Baths
  • 3,704 Sq Ft

  21 Davis St, Vineyard Haven, MA 02568

  Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home with 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect the care and craftsmanship the

  Paul Pertile The Agency

  21 Davis St, Vineyard Haven, MA 02568
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  $46,000 total monthly price

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

  99 Pond Road Wt104, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

  Karen Overtoom Karen M. Overtoom R.E.

  99 Pond Road Wt104, West Tisbury, MA 02575
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  $2,900,000 Sold Mar 30, 2026

  63 Bayes Hill Rd, Oak Bluffs, MA 02557

  • 4 Beds
  • 5 Baths
  • 5,165 Sq Ft
  • Built 1988

  Last Sold Summary

  • $561/SF
  • 35 Days On Market

  Current Estimated Value $2,875,270

  Last Listing Agent Casandra Hyland Sandpiper Realty, Inc.

  63 Bayes Hill Rd, Oak Bluffs, MA 02557
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  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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  $809,000

  • Land
  • 0.39 Acre
  • $2,074,359 per Acre

  7 Highland Ave, Vineyard Haven, MA 02568

  Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

  Shera Toledo eXp Realty, LLC

  7 Highland Ave, Vineyard Haven, MA 02568
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  $12,000 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • House for Rent

  267 Great Plains Road Wt117, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

  Karen Overtoom Karen M. Overtoom R.E.

  267 Great Plains Road Wt117, West Tisbury, MA 02575
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  $1,800,000 Sold Aug 26, 2025

  12 Martha's Park Rd, Oak Bluffs, MA 02557

  • 4 Beds
  • 1.5 Baths
  • 1,351 Sq Ft
  • Built 1910

  Last Sold Summary

  • 1% Below List Price
  • $1,332/SF
  • 0 Days On Market

  Current Estimated Value $1,721,205

  Last Listing Agent Michele Moore Island Real Estate

  12 Martha's Park Rd, 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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  $2,295,000

  • 4 Beds
  • 3 Baths
  • 3,015 Sq Ft

  3 Hidden Cove Rd, Oak Bluffs, MA 02557

  COMING SOON: HIDDEN COVE GEM WITH SERENE POND VIEWS AND COVETED WATER ACCESS. Located in the desirable Hidden Cove enclave, a 65+ acre water-access community with direct access to Sengekontacket Pond and Nantucket Sound, this inviting contemporary home offers privacy, comfort, and high-end finishes throughout. Community amenities include a private boat dock, walking trails, pickleball and tennis,

  Wendy Harman Compass | Point B

  3 Hidden Cove Rd, Oak Bluffs, MA 02557
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  $14,500 total monthly price

  • 5 Beds
  • 5.5 Baths
  • 3,392 Sq Ft
  • House for Rent

  76 School House Lane Wt101, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced proportions

  Karen Overtoom Karen M. Overtoom R.E.

  76 School House Lane Wt101, West Tisbury, MA 02575
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  $860,000 Sold Feb 09, 2026

  8 Hitchings Cir, Oak Bluffs, MA 02557

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Below List Price
  • $698/SF
  • 22 Days On Market

  Last Listing Agent Peyton Wallace Studio Realty

  8 Hitchings Cir, Oak Bluffs, MA 02557
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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.

Showing Results 121 - 160, Page 4 of 18