Tisbury, MA Homes

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  $1,495,000

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

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors 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

  

  Stephanie Burke

  Portfolio Properties

  (508) 687-6441

  33 Alyssa Ln, Vineyard Haven, MA 02568
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  $7,500 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,435 Sq Ft
  • House for Rent

  43 Edgartown Rd, Vineyard Haven, MA 02568

  Located off of Edgartown-Vineyard Haven Road, close to down-town and bike path, this 3 bedroom, 2 bath property is being offered year round to the right tenants. The home has been completely renovated, is being offered fully furnished and features an open floor plan with wood floors on the first level, wall to wall carpet in the upstairs bedrooms and an in-ground pool in the backyard. Available

  Karen Overtoom Karen M. Overtoom R.E.

  43 Edgartown Rd, Vineyard Haven, MA 02568
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  $1,300,000 Sold Feb 13, 2026

  169 Clover Hill Dr, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft
  • Built 1977

  Last Sold Summary

  • 4% Below List Price
  • $719/SF
  • 9 Days On Market

  Current Estimated Value $1,343,341

  Last Listing Agent Stephanie Roache Donnelly + Co

  169 Clover Hill Dr, Vineyard Haven, MA 02568
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  Est $3,977,492 Not Listed For Sale

  18 Bold Meadow Rd, Edgartown, MA 02539

  • 4 Beds
  • 6 Baths
  • 4,797 Sq Ft
  • Built 2024

  18 Bold Meadow Rd, Edgartown, MA 02539

  Last Sold Summary

  • 8% Below List Price
  • $896/SF
  • 241 Days On Market

  Last Sold Price $4,300,000

  Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties
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  /27

  $1,150,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  70 Carol Ln, Oak Bluffs, MA 02557

  Charming Renovated Ranch in the Heart of Oak Bluffs Discover the perfect blend of comfort, convenience, and coastal charm in this beautifully renovated ranch home, ideally located in a central Oak Bluffs neighborhood close to everything down-Island. Set on a spacious 1/3-acre lot, this property offers both privacy and proximity — just minutes from the Oak Bluffs School, town center, and all the

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 456-5742

  70 Carol Ln, Oak Bluffs, MA 02557
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  /21

  $9,500 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • House for Rent

  155 Skiff Ave, Vineyard Haven, MA 02568

  **SUMMER RENTAL ONLY** RATE IS WEEKLY** Enjoy the serenity of a four bedroom, two full bathroom peaceful oasis complete with private in-ground pool. Close to lively dining and boutiques of downtown Vineyard Haven. Unwind at neighborhood beaches; Eastville, Owen Park, Tashmoo beaches all just a few minutes drive from your vacation retreat.This lovely home spread over 1600ft of living area provides

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  155 Skiff Ave, Vineyard Haven, MA 02568
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  $1,550,000 Sold Oct 16, 2025

  251 State Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,986 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $780/SF
  • 114 Days On Market

  Current Estimated Value $1,573,414

  Last Listing Agent Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
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  /3

  Est $1,598,922 Not Listed For Sale

  18 Towanticut Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 2.5 Baths
  • 2,329 Sq Ft
  • Built 1989

  18 Towanticut Ave, Oak Bluffs, MA 02557

  Last Sold Summary

  • 7% Above List Price
  • $644/SF
  • 13 Days On Market

  Last Sold Price $1,500,000

  Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.
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  /34

  $3,250,000

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft

  6 Brewster Ave, Oak Bluffs, MA 02557

  Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

  Katherine Donahue Sandpiper Realty Inc

  6 Brewster Ave, Oak Bluffs, MA 02557
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  /41

  $13,500 total monthly price

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

  14 Bernard Cir, Vineyard Haven, MA 02568

  ** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar -

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  14 Bernard Cir, Vineyard Haven, MA 02568
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  $1,500,000 Sold Mar 30, 2026

  68 20th St S, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 1,975 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Below List Price
  • $759/SF
  • 28 Days On Market

  Current Estimated Value $1,598,800

  Last Listing Agent Carol Shore Donnelly + Co

  68 20th St S, Edgartown, MA 02539
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  Est $2,644,656 Not Listed For Sale

  28 Woodhaven Dr, Edgartown, MA 02539

  • 3 Beds
  • 3.5 Baths
  • 3,470 Sq Ft
  • Built 2013

  28 Woodhaven Dr, Edgartown, MA 02539

  Last Sold Summary

  • 15% Above List Price
  • $663/SF
  • 261 Days On Market

  Last Sold Price $2,300,000

  Last Listing Agent Stephanie Roache Donnelly + Co.
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  $1,999,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,453 Sq Ft

  34 Davis St, Tisbury, MA 02568

  NEW CONSTRUCTION – Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island’s harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

  Andrew McElhinney Compass LLC

  34 Davis St, Tisbury, MA 02568
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  $8,750 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft
  • House for Rent

  11 High Meadow Ln, Vineyard Haven, MA 02568

  **SUMMER WEEKLY RATE ** INQUIRE FOR LONG TERM OFFSEASON RATE**Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  11 High Meadow Ln, Vineyard Haven, MA 02568
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  $4,250,000 Sold Sep 09, 2025

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 4,125 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $1,030/SF
  • 21 Days On Market

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  /5

  Not Listed For Sale

  0 Bridle Path Rd, Vineyard Haven, MA 02568

  0 Bridle Path Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 7 Days On Market

  Last Sold Price $885,000

  Last Listing Agent Diana Gilmore Island Real Estate
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  /27

  $1,799,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,268 Sq Ft

  7 Upper Meadow Ln, Oak Bluffs, MA 02557

  Meadowview Farms — This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite with walk-in closets and private bath. The main living area flows from a living room with fireplace

  Lesley Heidt Sandpiper Realty, Inc.

  7 Upper Meadow Ln, Oak Bluffs, MA 02557
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  /27

  $21,700 total monthly price

  • 5 Beds
  • 3 Baths
  • 2,168 Sq Ft
  • House for Rent

  97 3rd St N, Edgartown, MA 02539

  YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

  Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

  97 3rd St N, Edgartown, MA 02539
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  $1,700,000 Sold Oct 20, 2025

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  • 5 Beds
  • 3 Baths
  • 1,803 Sq Ft
  • Built 1982

  Last Sold Summary

  • $943/SF
  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  Est $1,006,990 Not Listed For Sale

  287 County Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1998

  287 County Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 18% Above List Price
  • $759/SF
  • 10 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Jill Napior Tea Lane Associates
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  $2,260,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,810 Sq Ft

  4 High Meadow Ln, Oak Bluffs, MA 02557

  Classic Post & Beam set in Meadow View Farms - This stunning and solidly built four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. A farmer’s porch stretches the full length of the home offering a warm welcome and a shady spot to relax overlooking the expansive front lawn. The light-filled, open first floor boasts cathedral ceilings, and

  Kate Burnside Portfolio Properties

  4 High Meadow Ln, Oak Bluffs, MA 02557
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  /22

  $20,000 total monthly price

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

  55 Samoset Ave, Oak Bluffs, MA 02557

  Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  55 Samoset Ave, Oak Bluffs, MA 02557
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  $1,800,000 Sold Oct 15, 2025

  82 Skiff Ave, Tisbury, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 1,913 Sq Ft
  • Built 2020

  Last Sold Summary

  • 10% Below List Price
  • $941/SF
  • 128 Days On Market

  Current Estimated Value $1,663,874

  Last Listing Agent Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
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  Est $1,513,490 Not Listed For Sale

  19 Quantapog Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 2,298 Sq Ft
  • Built 1988

  19 Quantapog Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 10% Above List Price
  • $601/SF
  • 22 Days On Market

  Last Sold Price $1,380,000

  Last Listing Agent Leslie Floyd Portfolio Real Estate Inc.
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  $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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  $28,500 total monthly price

  • 9 Beds
  • 6.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  9 Tuckernuck Ave, Oak Bluffs, MA 02557

  **SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  9 Tuckernuck Ave, Oak Bluffs, MA 02557
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  /19

  $750,000 Sold Nov 07, 2025

  41 Trinity Park, Oak Bluffs, MA 02557

  • 4 Beds
  • 1 Bath
  • 1,154 Sq Ft
  • Built 1867

  Last Sold Summary

  • 6% Below List Price
  • $650/SF
  • 14 Days On Market

  Current Estimated Value $768,170

  Last Listing Agent Stacy Ickes Donnelly + Co.

  41 Trinity Park, Oak Bluffs, MA 02557
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  Est $1,201,052 Not Listed For Sale

  3 Carole Ave, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,997 Sq Ft
  • Built 1985

  3 Carole Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Above List Price
  • $576/SF
  • 209 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Bob Sparks American Real Estate LLC
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  /41

  $1,800,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 1 Sq Ft

  18 Wood Duck Way, Edgartown, MA 02539

  Turnkey modern home with 4 bedrooms and 3 full baths, filled with natural light from large windows and soaring ceilings. The first floor offers three bedrooms and a full bath with double sinks, while warm oak and maple floors are accented by cherry stairs and custom built-ins.The open-concept second level features a spacious kitchen, living, and dining area, along with a private primary en suite

  Janna O'Loughlin Portfolio Properties

  18 Wood Duck Way, Edgartown, MA 02539
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  $20,000 total monthly price

  • 5 Beds
  • 3 Baths
  • 2,352 Sq Ft
  • House for Rent

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

  Karen Overtoom Karen M. Overtoom R.E.

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
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  /19

  $1,110,000 Sold May 08, 2025

  31 9th St N, Edgartown, MA 02539

  • 2 Beds
  • 1.5 Baths
  • 1,275 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $871/SF
  • 45 Days On Market

  Current Estimated Value $1,137,828

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

  31 9th St N, Edgartown, MA 02539
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  Est $1,200,225 Not Listed For Sale

  33 Menahan St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • Built 1993

  33 Menahan St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Above List Price
  • $830/SF
  • 48 Days On Market

  Last Sold Price $1,185,000

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc
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  $1,750,000

  • 3 Beds
  • 2.5 Baths
  • 2,862 Sq Ft

  103 Meadow View Rd, Oak Bluffs, MA 02557

  Nestled on a rare, oversized 1.5-acre lot, this spacious 3-bed/2 1/2 bath contemporary home offers a perfect blend of privacy and coastal convenience. Perched elegantly upon a gentle rise, the residence is bathed in natural light and framed by a beautifully landscaped lawn with mature plantings. The interior is designed for both comfort and scale. An expansive front living room has soaring

  Alyson Parker Karen M. Overtoom R.E.

  103 Meadow View Rd, Oak Bluffs, MA 02557
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  $17,500 total monthly price

  • 8 Beds
  • 4.5 Baths
  • 3,876 Sq Ft
  • House for Rent

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and relaxing

  Karen Overtoom Karen M. Overtoom R.E.

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
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  $1,325,000 Sold Jun 30, 2025

  191 Spring Hill Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 4 Baths
  • 2,292 Sq Ft
  • Built 1992

  Last Sold Summary

  • 5% Below List Price
  • $578/SF
  • 10 Days On Market

  Current Estimated Value $1,238,418

  Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

  191 Spring Hill Rd, Vineyard Haven, MA 02568
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  Est $971,572 Not Listed For Sale

  51 Manchester Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft
  • Built 1978

  51 Manchester Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 2% Above List Price
  • $933/SF
  • 22 Days On Market

  Last Sold Price $955,000

  Last Listing Agent Roy Cutrer LAER Realty Partners
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  /45

  $1,765,000

  • 2 Beds
  • 2 Baths
  • 890 Sq Ft

  2 Great Rock Rd, Oak Bluffs, MA 02568

  Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property

  Susan Lemoie-Zarba Premier Properties

  2 Great Rock Rd, Oak Bluffs, MA 02568
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  /10

  $8,500 total monthly price

  • 3 Beds
  • 2 Baths
  • House for Rent

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

  Karen Overtoom Karen M. Overtoom R.E.

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
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  /26

  $1,600,000 Sold Nov 07, 2025

  96 Pondview Dr, Oak Bluffs, MA 02536

  • 4 Beds
  • 2.5 Baths
  • 2,115 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $757/SF
  • 35 Days On Market

  Last Listing Agent Doug Burke Cronigs Real Estate

  96 Pondview Dr, Oak Bluffs, MA 02536
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  /2

  Est $2,455,030 Not Listed For Sale

  230 Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 4 Baths
  • 3,527 Sq Ft
  • Built 1999

  230 Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 8% Above List Price
  • $646/SF
  • 100 Days On Market

  Last Sold Price $2,280,000

  Last Listing Agent Rose Ryley Sandpiper Realty Inc

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