Vineyard Haven, MA Homes

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  $1,785,000

  • 3 Beds
  • 2.5 Baths
  • 1,406 Sq Ft

  17 John Wesley Ave, Vineyard Haven, MA 02568

  Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features

  kyle Neyer Tea Lane Associates

  17 John Wesley Ave, Vineyard Haven, MA 02568
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  /30

  $28,500 Per Month

  • 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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  $1,995,000 Sold Aug 29, 2025

  26 Box Turtle Ln, Oak Bluffs, MA 02557

  • 4 Beds
  • 3.5 Baths
  • 2,891 Sq Ft
  • Built 1980

  Last Sold Summary

  • $690/SF
  • 5 Days On Market

  Current Estimated Value $2,091,936

  Last Listing Agent Jayne Isford Ocean Park Realty Inc

  26 Box Turtle Ln, Oak Bluffs, MA 02557
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  /2

  Est $2,613,813 Not Listed For Sale

  5 Bold Meadow Cir, Edgartown, MA 02539

  • 4 Beds
  • 4 Baths
  • 3,252 Sq Ft
  • Built 1995

  5 Bold Meadow Cir, Edgartown, MA 02539

  Last Sold Summary

  • 7% Below List Price
  • $750/SF

  • Last Sold Price $2,438,500

  Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate
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  /31

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 1,431 Sq Ft

  33 Vineyard Ave, Oak Bluffs, MA 02557

  Welcome to 33 Vineyard Ave a completely renovated two-bedroom, two bathroom primary residence and attached one bedroom, one bathroom secondary suite offering a move-in ready, flexible living investment opportunity nestled in the heart of Oak Bluffs. This property offers perfect proximity to Downtown Oak Bluffs with fast access to harbor front, restaurants, shopping, historic parks, multiple

  Allison Parry Douglas Elliman MV

  33 Vineyard Ave, Oak Bluffs, MA 02557
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  /22

  $3,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,703 Sq Ft
  • House for Rent

  41 Oak Lane Wt147, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

  Karen Overtoom Karen M. Overtoom R.E.

  41 Oak Lane Wt147, West Tisbury, MA 02575
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  /18

  $995,000 Sold Nov 06, 2025

  2 Flamingo Dr, Edgartown, MA 02539

  • 3 Beds
  • 1 Bath
  • 990 Sq Ft
  • Built 1983

  Last Sold Summary

  • 5% Below List Price
  • $1,005/SF
  • 5 Days On Market

  Current Estimated Value $1,034,012

  Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

  2 Flamingo Dr, Edgartown, MA 02539
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  Est $4,529,964 Not Listed For Sale

  225 Bigelow Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,603 Sq Ft
  • Built 1976

  225 Bigelow Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 10% Above List Price
  • $1,575/SF
  • 70 Days On Market

  • Last Sold Price $4,100,000
  • Nov 03, 2014

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's
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  /23

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 2,864 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 Per Month

  • 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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  $1,890,000 Sold Aug 29, 2025

  1 Thames Ct, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 3,270 Sq Ft
  • Built 1981

  Last Sold Summary

  • $578/SF
  • 38 Days On Market

  Current Estimated Value $1,963,429

  Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

  1 Thames Ct, Edgartown, MA 02539
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  /20

  Est $1,616,973 Not Listed For Sale

  21 Bold Meadow Ln, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,971 Sq Ft
  • Built 1991

  21 Bold Meadow Ln, Edgartown, MA 02539

  Last Sold Summary

  • 18% Above List Price
  • $698/SF
  • 34 Days On Market

  • Last Sold Price $1,375,000
  • Jul 14, 2023

  Last Listing Agent Martha Smith C McManus Realty Group
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  $2,250,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,983 Sq Ft

  157 Ben Chase Rd, West Tisbury, MA 02575

  You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

  Madelyn Silvia Wallace & Co. Sotheby's

  157 Ben Chase Rd, West Tisbury, MA 02575
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  /18

  $10,000 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • House for Rent

  100 Franklin Terrace Vh411, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

  Karen Overtoom Karen M. Overtoom R.E.

  100 Franklin Terrace Vh411, Tisbury, MA 02568
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  $899,000 Sold Jul 11, 2025

  8 Rock Ave, Oak Bluffs, MA 02557

  • 3 Beds
  • 1.5 Baths
  • 955 Sq Ft
  • Built 1871

  Last Sold Summary

  • $941/SF
  • 6 Days On Market

  Current Estimated Value $921,674

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  8 Rock Ave, Oak Bluffs, MA 02557
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  /27

  Est $1,277,631 Not Listed For Sale

  46 Windsor Dr, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1987

  46 Windsor Dr, Edgartown, MA 02539

  Last Sold Summary

  • 7% Above List Price
  • $786/SF
  • 1,366 Days On Market

  • Last Sold Price $1,195,000
  • Jun 05, 2015

  Last Listing Agent Fran Agnoli The Agency
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  $1,275,000

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  34 10th St S, Edgartown, MA 02539

  Welcome to easy Edgartown living in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout ideal for both everyday life and entertaining. The private primary suite includes its own bath, while two additional

  Chrissie Teague Insight Realty Group, Inc.

  34 10th St S, Edgartown, MA 02539
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  $8,750 Per Month

  • 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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  $1,067,000 Sold Sep 26, 2025

  112 W Spring St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,503 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $710/SF
  • 9 Days On Market

  Current Estimated Value $1,081,951

  Last Listing Agent Katie Donahue Sandpiper Realty

  112 W Spring St, Vineyard Haven, MA 02568
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  Est $5,940,988 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

  • 50% Below List Price
  • $1,833/SF

  • Last Sold Price $12,000,000

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's
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  $510,000

  • 1 Bed
  • 1.5 Baths
  • 590 Sq Ft

  21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

  Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

  Diana Gilmore Island Real Estate

  21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
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  $10,800 Per Month

  • 2 Beds
  • 4 Baths
  • 1,800 Sq Ft
  • House for Rent

  256 Sandpiper Lane Vh417, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

  Karen Overtoom Karen M. Overtoom R.E.

  256 Sandpiper Lane Vh417, Tisbury, MA 02568
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  /20

  $929,000 Sold Aug 18, 2025

  299 Franklin St, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,286 Sq Ft
  • Built 1950

  Last Sold Summary

  • $722/SF
  • 7 Days On Market

  Current Estimated Value $976,490

  Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

  299 Franklin St, Vineyard Haven, MA 02568
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  Est $1,556,989 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

  • 11% Above List Price
  • $964/SF
  • 59 Days On Market

  • Last Sold Price $1,400,000
  • May 20, 2024

  Last Listing Agent Candy DaRosa Feiner Real Estate
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  $5,325,000

  • 6 Beds
  • 4 Baths
  • 2,890 Sq Ft

  4 Canonicus Ave, Oak Bluffs, MA 02557

  Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  4 Canonicus Ave, Oak Bluffs, MA 02557
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  /15

  $7,500 Per Month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  83 Ashtons Way, Vineyard Haven, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

  Karen Overtoom Karen M. Overtoom R.E.

  83 Ashtons Way, Vineyard Haven, MA 02568
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  $1,525,000 Sold Jun 18, 2025

  54 Lake St, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,016 Sq Ft
  • Built 1967

  Last Sold Summary

  • 12% Below List Price
  • $756/SF
  • 110 Days On Market

  Current Estimated Value $1,570,313

  Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

  54 Lake St, Vineyard Haven, MA 02568
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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
  • Apr 16, 2024

  Last Listing Agent Andrew McElhinney Compass LLC
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  $625,000

  • Land
  • 14,997 Sq Ft
  • $1,815,277 per Acre

  0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

  Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

  Andrew McElhinney Compass LLC

  0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
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  $8,000 Per Month

  • 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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  $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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  Est $1,774,865 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

  • 6% Above List Price
  • $683/SF
  • 52 Days On Market

  • Last Sold Price $1,680,000
  • Oct 26, 2023

  Last Listing Agent Peyton Wallace Studio Realty
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  $899,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  17 Mariner Rd, Vineyard Haven, MA 02568

  This home has been patiently awaiting its next chapter in Vineyard living. Built in 1983, it offers a functional center-entrance layout with efficient use of space and modern systems already in place. The generously sized lot, both wide and deep, presents an excellent opportunity to expand the home's footprint and tailor it to your vision. Located in the Spring Hill neighborhood of single-family

  Karl Olsen Carlson & Company, LLC

  17 Mariner Rd, Vineyard Haven, MA 02568
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  /20

  $12,000 Per Month

  • 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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  $665,000 Sold Mar 06, 2026

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

  • Land
  • 11,133 Sq Ft
  • $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 $1,474,820 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

  • 23% Above List Price
  • $525/SF
  • 0 Days On Market

  • Last Sold Price $1,200,000
  • Jul 07, 2023

  Last Listing Agent LINK Email Cache LINK
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  $4,500,000

  • 4 Beds
  • 3 Baths
  • 2,715 Sq Ft

  94 Weaver Ln, Vineyard Haven, MA 02568

  Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows

  Emma Kennedy Sandpiper Realty, Inc.

  94 Weaver Ln, Vineyard Haven, MA 02568
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  $12,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  223 Sandpiper Lane Vh405, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

  Karen Overtoom Karen M. Overtoom R.E.

  223 Sandpiper Lane Vh405, Tisbury, MA 02568
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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 $1,034,468

  Last Listing Agent LINK Email Cache LINK

  5 Johns Way, Oak Bluffs, MA 02557
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  Est $1,991,791 Not Listed For Sale

  83 Dolan Ave, Vineyard Haven, MA 02568

  • 5 Beds
  • 4.5 Baths
  • 3,841 Sq Ft
  • Built 1994

  83 Dolan Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6% Above List Price
  • $488/SF
  • 24 Days On Market

  • Last Sold Price $1,875,000
  • Apr 01, 2025

  Last Listing Agent Courtney Marek Sandpiper Realty

Showing Results 81 - 120, Page 3 of 18