Dukes County, MA Homes

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  $2,095,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,695 Sq Ft

  43C Dark Woods Rd, Edgartown, MA 02539

  Welcome to Dark Woods – A Quiet Retreat with Prime Convenience. Enjoy the ease and comfort of life in Dark Woods, a tranquil neighborhood ideally located just moments from the Village, scenic bike paths, pristine beaches, and 27 acres of Sheriff’s Meadow conservation land. This meticulously maintained property is being offered fully furnished and is ready for your immediate enjoyment. Sited on a

  Stephanie Roache Donnelly + Co

  43C Dark Woods Rd, Edgartown, MA 02539
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  $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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  $982,000 Sold Dec 19, 2025

  25 Windy Hill Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $1,002/SF
  • 10 Days On Market

  Current Estimated Value $985,447

  Last Listing Agent Rene Jackson Island Real Estate

  25 Windy Hill Rd, Oak Bluffs, MA 02557
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  Est $1,783,584 Not Listed For Sale

  179 Main St, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 1 Sq Ft
  • Built 1840

  179 Main St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 16% Above List Price
  • $1,535,625/SF
  • 14 Days On Market

  Last Sold Price $1,535,625

  Last Listing Agent Judy Federowicz Landmarks at TODAY Real Estate
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  $2,150,000

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  33 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  33 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  $18,840 total monthly price

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  21 William St Vh430, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

  Karen Overtoom Karen M. Overtoom R.E.

  21 William St Vh430, Tisbury, MA 02568
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  $1,350,000 Sold Aug 15, 2025

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $724/SF
  • 12 Days On Market

  Last Listing Agent Lesley Heidt Sandpiper Realty Inc

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
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  /23

  Est $2,061,276 Not Listed For Sale

  31 Pulpit Ln, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • Built 2001

  31 Pulpit Ln, Edgartown, MA 02539

  Last Sold Summary

  • 3% Above List Price
  • $1,174/SF
  • 169 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Courtney Marek Sandpiper Realty
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  $2,790,000

  • 3 Beds
  • 3.5 Baths
  • 2,898 Sq Ft

  4 Pip'N Rd, Edgartown, MA 02539

  Where Chappaquiddick’s natural beauty meets Edgartown sophistication, this impeccably maintained custom home offers thoughtful design and exceptional livability. The professionally styled interior features an inviting foyer, a gracious dining room open to a living room with fireplace and glass doors to the deck, and a gourmet kitchen with island and banquette. A sun porch, wet bar, powder room,

  Lesley Heidt Sandpiper Realty, Inc.

  4 Pip'N Rd, Edgartown, MA 02539
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  $32,000 total monthly price

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  37 Mempremagog Ave Vh410, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  37 Mempremagog Ave Vh410, Tisbury, MA 02568
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  $700,500 Sold May 07, 2025

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539

  • Land
  • 0.55 Acre
  • $1,273,636 per Acre

  Last Sold Summary

  • 3% Above List Price
  • 0 Days On Market

  Last Listing Agent Jim Joyce Carroll & Vincent R.E.

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539
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  Not Listed For Sale

  670 State Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3.5 Baths
  • 2,092 Sq Ft
  • Built 1920

  670 State Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • $550/SF
  • 68 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Nya Clarke Martha's Vineyard Island-Wide Realty
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  $560,000

  • 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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  $10,000 total monthly price

  • 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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  $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
  • 95 Days On Market

  Current Estimated Value $1,081,877

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  112 W Spring St, Vineyard Haven, MA 02568
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  Est $1,162,000 Not Listed For Sale

  29 Dunham Ave, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • Built 1965

  29 Dunham Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 5% Below List Price
  • $892/SF
  • 0 Days On Market

  Last Sold Price $1,220,000

  Last Listing Agent LINK Email Cache LINK
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  $950,000

  • 2 Beds
  • 2 Baths
  • 1,583 Sq Ft

  25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

  Maranda Post Compass LLC

  25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  $10,800 total monthly price

  • 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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  $1,525,000 Sold Oct 07, 2025

  15 Jernegan Pond Rd, Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 2,042 Sq Ft
  • Built 1945

  Last Sold Summary

  • 23% Below List Price
  • $747/SF
  • 233 Days On Market

  Last Listing Agent Lesley Heidt Sandpiper Realty Inc

  15 Jernegan Pond Rd, Edgartown, MA 02539
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  Est $765,972 Not Listed For Sale

  32 Clark Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1968

  32 Clark Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Below List Price
  • $1,011/SF
  • 17 Days On Market

  Last Sold Price $776,500

  Last Listing Agent Diana Gilmore Island Real Estate
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  $1,600,000 Pending

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

  68 20th St S, Edgartown, MA 02539

  This well-maintained custom Cape Cod–style home is ideally suited for year-round living, vacation getaway, or employee housing. Located at the end of a quiet street next to Pennywise Preserve conservation land, it enjoys extra privacy. The main level features an open layout with vaulted ceilings. There is a spacious den above an oversized two-car garage and an expansive deck for entertaining

  Carol Shore Donnelly + Co

  68 20th St S, Edgartown, MA 02539
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  $7,500 total monthly price

  • 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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  $1,662,000 Sold Apr 16, 2025

  395 Edgartown - West Tisbury Rd, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,794 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $926/SF
  • 0 Days On Market

  Current Estimated Value $1,663,949

  Last Listing Agent Janna O'Loughlin Portfolio Properties

  395 Edgartown - West Tisbury Rd, Edgartown, MA 02539
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  Est $655,549 Not Listed For Sale

  5 Village Ct Unit 3, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 658 Sq Ft
  • Built 1972

  5 Village Ct Unit 3, Vineyard Haven, MA 02568

  Last Sold Summary

  • 7% Above List Price
  • $935/SF
  • 87 Days On Market

  Last Sold Price $615,000

  Last Listing Agent Martha Smith C McManus Realty Group
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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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  $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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  $1,865,000 Sold Dec 04, 2025

  71 Netock Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 5 Baths
  • 2,820 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $661/SF
  • 11 Days On Market

  Current Estimated Value $1,891,636

  Last Listing Agent Ellen Valentgas Sotheby's International Realty

  71 Netock Ave, Oak Bluffs, MA 02557
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  Est $2,426,952 Not Listed For Sale

  23 Oak Ln, Vineyard Haven, MA 02568

  • 6 Beds
  • 4.5 Baths
  • 3,035 Sq Ft
  • Built 2007

  23 Oak Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Above List Price
  • $791/SF
  • 213 Days On Market

  Last Sold Price $2,400,000

  Last Listing Agent Lynn Buder Sandpiper Realty Inc
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  $3,100,000

  • Land
  • 3.04 Acres
  • $1,019,737 per Acre

  114 Meeting House Way, Edgartown, MA 02539

  3 Acre Katama Building Lot with Existing Guest House.This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South

  Rose Ryley Wallace & Co. Sotheby's

  114 Meeting House Way, Edgartown, MA 02539
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  $25,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,334 Sq Ft
  • House for Rent

  100 Connie's Way Vh401, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

  Karen Overtoom Karen M. Overtoom R.E.

  100 Connie's Way Vh401, Tisbury, MA 02568
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  $1,125,000 Sold Oct 28, 2025

  140 Longview Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,432 Sq Ft
  • Built 1964

  Last Sold Summary

  • 13% Below List Price
  • $786/SF
  • 97 Days On Market

  Current Estimated Value $1,103,456

  Last Listing Agent Candy DaRosa Feiner Real Estate

  140 Longview Rd, Vineyard Haven, MA 02568
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  Est $1,866,311 Not Listed For Sale

  79 Watcha Path, Edgartown, MA 02539

  • 4 Beds
  • 6 Baths
  • 4,306 Sq Ft
  • Built 1980

  79 Watcha Path, Edgartown, MA 02539

  Last Sold Summary

  • 18% Above List Price
  • $366/SF
  • 3 Days On Market

  Last Sold Price $1,575,000

  Last Listing Agent Robin Perschel Feiner Real Estate
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  $625,000

  • Land
  • 0.34 Acre
  • $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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  $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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  $2,075,000 Sold Sep 29, 2025

  24 Dark Woods Rd, Edgartown, MA 02539

  • 3 Beds
  • 3.5 Baths
  • 2,638 Sq Ft
  • Built 1998

  Last Sold Summary

  • 23% Below List Price
  • $787/SF
  • 372 Days On Market

  Current Estimated Value $2,303,991

  Last Listing Agent Stephanie Burke Portfolio Properties

  24 Dark Woods Rd, Edgartown, MA 02539
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  Est $2,671,684 Not Listed For Sale

  5 Bold Meadow Cir, Edgartown, MA 02539

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

  5 Bold Meadow Cir, Edgartown, MA 02539

  Last Sold Summary

  • 10% Above List Price
  • $750/SF
  • 45 Days On Market

  Last Sold Price $2,438,500

  Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate
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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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  $12,000 total monthly price

  • 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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  $7,289,000 Sold Oct 15, 2025

  25 Osprey Ln, Chilmark, MA 02535

  • 4 Beds
  • 5 Baths
  • 3,777 Sq Ft
  • Built 1988

  Last Sold Summary

  • 9% Below List Price
  • $1,930/SF
  • 77 Days On Market

  Current Estimated Value $6,853,287

  Last Listing Agent Deb Hancock Hancock Real Estate

  25 Osprey Ln, Chilmark, MA 02535
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  Not Listed For Sale

  11 Cummings Way, Edgartown, MA 02539

  • 6 Beds
  • 8 Baths
  • 4,617 Sq Ft
  • Built 2007

  11 Cummings Way, Edgartown, MA 02539

  Last Sold Summary

  • $1,444/SF
  • 100 Days On Market

  Last Sold Price $6,665,000

  Last Listing Agent Wendy Harman Compass

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