Vineyard Haven, MA Homes

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  /12

  $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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  /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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  /42

  $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 $1,357,691

  Last Listing Agent Stephanie Roache Donnelly + Co

  169 Clover Hill Dr, Vineyard Haven, MA 02568
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  /17

  Est $1,242,091 Not Listed For Sale

  22 Briarwood Ln, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft
  • Built 2018

  22 Briarwood Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Below List Price
  • $1,048/SF
  • 4 Days On Market

  Last Sold Price $1,300,000

  Last Listing Agent Carol Shore Donnelly + Co
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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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  /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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  /30

  $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 $1,667,700

  Last Listing Agent Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
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  /10

  Not Listed For Sale

  0 Shawanue Ave Unit 32400336, Oak Bluffs, MA 02557

  0 Shawanue Ave Unit 32400336, Oak Bluffs, MA 02557

  Last Sold Summary

  • 70 Days On Market

  Last Sold Price $550,000

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

  $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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  /18

  $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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  Est $1,082,211 Not Listed For Sale

  18 Brunswick Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 875 Sq Ft
  • Built 1870

  18 Brunswick Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 3% Above List Price
  • $1,206/SF
  • 115 Days On Market

  Last Sold Price $1,055,000

  Last Listing Agent Cheri Mason LandVest MV
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  /28

  $1,799,000

  • 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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  /38

  $2,860,000 Sold Mar 10, 2025

  49 William St, Vineyard Haven, MA 02568

  • 5 Beds
  • 4.5 Baths
  • 3,752 Sq Ft
  • Built 1836

  Last Sold Summary

  • 12% Below List Price
  • $762/SF
  • 290 Days On Market

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

  49 William St, Vineyard Haven, MA 02568
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  /2

  Not Listed For Sale

  49 Oak Ln, West Tisbury, MA 02575

  • 4 Beds
  • 3.5 Baths
  • 2,576 Sq Ft
  • Built 1974

  49 Oak Ln, West Tisbury, MA 02575

  Last Sold Summary

  • $639/SF
  • 6 Days On Market

  Last Sold Price $1,645,000

  Last Listing Agent Dawn Bellante Sandpiper Realty Inc
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  /33

  $1,750,000

  • 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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  /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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  /26

  $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 $1,759,970

  Last Listing Agent Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
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  /34

  Est $1,136,715 Not Listed For Sale

  2 Nahomon St, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1978

  2 Nahomon St, Oak Bluffs, MA 02557

  Last Sold Summary

  • 20% Above List Price
  • $731/SF
  • 87 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Jarrod Smith Romano Real Estate
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  /37

  $1,750,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,058 Sq Ft

  2 Farm Path, Oak Bluffs, MA 02557

  "Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

  Sean Federowicz Landmarks at TODAY Real Estate

  2 Farm Path, Oak Bluffs, MA 02557
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  /30

  $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 $783,349

  Last Listing Agent Stacy Ickes Donnelly + Co.

  41 Trinity Park, Oak Bluffs, MA 02557
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  /3

  Est $1,591,742 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

  • 6% 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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  /39

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 2,064 Sq Ft

  18 Wood Duck Way, Edgartown, MA 02539

  Being sold turnkey and fully furnished, this modern home has four bedrooms and three full baths. Large windows and high ceilings, the home lets in bright natural light. The first floor has three bedrooms and a full bath with double sinks. Beautiful oak and maple floors complement the cherry stairs and living room built-ins. Open concept second level contains the open concept kitchen, living room,

  Janna O'Loughlin Portfolio Properties

  18 Wood Duck Way, Edgartown, MA 02539
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  /10

  $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 $1,170,058

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

  31 9th St N, Edgartown, MA 02539
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  /36

  Est $2,617,652 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

  • 14% 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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  /23

  $2,260,000

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

  4 High Meadow Ln, Oak Bluffs, MA 02557

  Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

  Kate Burnside Portfolio Properties

  4 High Meadow Ln, Oak Bluffs, MA 02557
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  /8

  $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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  /31

  $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 $1,259,725

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

  191 Spring Hill 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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  /24

  $1,950,000

  • 2 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  378 State Rd, Vineyard Haven, MA 02568

  MIXED USE PROPERTY WITH PROFESSIONAL OFFICES AND TWO-BEDROOM APARTMENT - Extensively renovated mixed-use property offering commercial + residential use in a high-visibility location on State Road in Tisbury. This versatile property presents a true live-work opportunity with strong income-producing potential.The first floor offers four offices including a reception area, 1.5 baths, and a

  Lesley Heidt Sandpiper Realty Inc

  378 State Rd, Vineyard Haven, 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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  /38

  Est $1,034,721 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

  • 22% 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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  /44

  $1,650,000

  • 4 Beds
  • 3 Baths
  • 2,760 Sq Ft

  52 Carrolls Way, Vineyard Haven, MA 02568

  SHOWINGS START TUESDAY FEBRUARY 3. It's a home but also used as a business! R-20 zoning with historical home business uses next to Carrolls Trucking and other mixed uses. Currently its used as a 3-bedroom home with a 1-bedroom apartment, a business is being run out of the huge 576 sq. ft office. There are multiple storage and garage options to lend to a variety of needs. Being in the R-20 zoning

  Jim Feiner Feiner Real Estate

  52 Carrolls Way, Vineyard Haven, MA 02568
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  /8

  $11,800 total monthly price

  • 4 Beds
  • 4 Baths
  • 2,612 Sq Ft
  • House for Rent

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

  Karen Overtoom Karen M. Overtoom R.E.

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
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  /25

  $949,000 Sold Jun 23, 2025

  345 Franklin St, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,012 Sq Ft
  • Built 1986

  Last Sold Summary

  • $938/SF
  • 49 Days On Market

  Current Estimated Value $963,496

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

  345 Franklin St, Vineyard Haven, MA 02568
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  /17

  Est $1,541,098 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

  • 12% 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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