Edgartown, MA Homes

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  $3,895,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  44 Plantingfield Way, Edgartown, MA 02539

  Post-and-beam style Edgartown home in a quiet, established neighborhood just minutes from downtown. This year-round home offers functional living spaces, a thoughtful layout, and generous outdoor areas ideal for relaxing or entertaining. Currently configured with a 3BR/1.5BA main house and 1BR/1BA accessory apartment over a one-car garage, this property affords multiple options for would-be

  David Dickinson Compass | Point B

  44 Plantingfield Way, Edgartown, MA 02539
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  $13,600 Per Month

  • 2 Beds
  • 2 Baths
  • 1,967 Sq Ft
  • Condo for Rent

  1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Enjoy this well appointed and immaculately clean two bedroom condo located just steps from the association pool and a short drive to South Beach with its gorgeous white sands. An open living room, kitchen and dining room with walk-out access to the deck and back yard offer plenty of gathering spaces to enjoy your company over meals, snacks and games

  Karen Overtoom Karen M. Overtoom R.E.

  1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539
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  $2,700,000 Sold Dec 19, 2025

  43 Cottage St, Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 1,112 Sq Ft
  • Built 1945

  Last Sold Summary

  • 16% Below List Price
  • $2,428/SF
  • 7 Days On Market

  Current Estimated Value $2,874,398

  Last Listing Agent Michele Casavant Vineyard Village Realty

  43 Cottage St, Edgartown, MA 02539
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  Est $2,491,910 Not Listed For Sale

  53 Peases Point Way N, Edgartown, MA 02539

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • Built 1928

  53 Peases Point Way N, Edgartown, MA 02539

  Last Sold Summary

  • $1,467/SF
  • 0 Days On Market

  • Last Sold Price $2,500,000
  • Sep 03, 2024

  Last Listing Agent Jennifer O'hanlon Compass LLC
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  $3,450,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,327 Sq Ft

  25 Bold Meadow Rd, Edgartown, MA 02539

  This distinguished home in the Bold Meadow neighborhood of Edgartown offers so much. Immediately upon entering one is captivated by the light and bright interiors showcased by the banks of south-facing windows in the cathedral-ceilinged Great Room. This continues through to the new sunroom. The property has been immaculately maintained, and with 3 bedrooms in the main house plus a large detached

  Mark Jenkins Wallace & Co. Sotheby's

  25 Bold Meadow Rd, 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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  $37,500,000 Sold Oct 30, 2025

  48 Witchwood Ln, Edgartown, MA 02539

  • 9 Beds
  • 9.5 Baths
  • 16,209 Sq Ft
  • Built 2000

  Last Sold Summary

  • $2,314/SF
  • 0 Days On Market

  Last Listing Agent Gerrett Conover Landvest MV

  48 Witchwood Ln, Edgartown, MA 02539
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  Not Listed For Sale

  56 Pinehurst Rd, Edgartown, MA 02539

  • 4 Beds
  • 2.5 Baths
  • 2,328 Sq Ft
  • Built 1973

  56 Pinehurst Rd, Edgartown, MA 02539

  Last Sold Summary

  • $1,108/SF
  • 141 Days On Market

  • Last Sold Price $2,580,000
  • Nov 18, 2024

  Last Listing Agent Wendy Harman Compass
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  /39

  $3,195,000

  • 3 Beds
  • 3.5 Baths
  • 2,268 Sq Ft

  23 Thaxter Ln, Edgartown, MA 02539

  OPEN AND AIRY COASTAL RETREAT WITH EASY ACCESS TO SOUTH BEACH and EDGARTOWN VILLAGE. Welcome to this tri-level contemporary home in the heart of KATAMA. This home offers the perfect blend of spacious indoor-outdoor living with three levels of outdoor decking nestled amongst mature vegetation and a quick stroll to South Beach. The home features vaulted ceilings, two first floor bedroom en-suites,

  Michele Casavant Vineyard Village Realty

  23 Thaxter Ln, 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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  $1,000,000 Sold Jan 13, 2026

  48 Edgartown - West Tisbury Rd, Edgartown, MA 02539

  • 3 Beds
  • 3 Baths
  • 1,959 Sq Ft
  • Built 1950

  Last Sold Summary

  • 29% Below List Price
  • $510/SF
  • 86 Days On Market

  Last Listing Agent Mavis Francis eXp Realty

  48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
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  Est $5,822,862 Not Listed For Sale

  100 Meetinghouse Way, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 3,193 Sq Ft
  • Built 1976

  100 Meetinghouse Way, Edgartown, MA 02539

  Last Sold Summary

  • 8% Below List Price
  • $1,988/SF
  • 5 Days On Market

  • Last Sold Price $6,349,000
  • Sep 21, 2023

  Last Listing Agent Jennifer DaSilva Compass | Point B
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  $2,950,000

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft

  9 N Neck Rd, Edgartown, MA 02539

  COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming,

  Leslie C. Floyd Portfolio Properties

  9 N Neck Rd, Edgartown, MA 02539
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  $36,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,556 Sq Ft
  • House for Rent

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The kitchen has granite countertops,

  Karen Overtoom Karen M. Overtoom R.E.

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539
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  $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 Signal House Group at Compass

  96 Pondview Dr, Oak Bluffs, MA 02536
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  Est $3,702,804 Not Listed For Sale

  94 Marthas Rd, Edgartown, MA 02539

  • 6 Beds
  • 4.5 Baths
  • 3,902 Sq Ft
  • Built 2008

  94 Marthas Rd, Edgartown, MA 02539

  Last Sold Summary

  • 11% Above List Price
  • $859/SF
  • 0 Days On Market

  • Last Sold Price $3,350,000
  • Sep 07, 2012

  Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's International Realty
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  $2,999,000

  • 8 Beds
  • 7.5 Baths
  • 3,770 Sq Ft

  72 Chappaquiddick Ave, Edgartown, MA 02539

  WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the

  Michele Casavant Vineyard Village Realty

  72 Chappaquiddick Ave, Edgartown, MA 02539
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  $29,300 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,871 Sq Ft
  • House for Rent

  76 Mattakesett Way Ed313, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while lazing on the porch swing.The

  Karen Overtoom Karen M. Overtoom R.E.

  76 Mattakesett Way Ed313, Edgartown, MA 02539
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  $3,695,000 Sold Nov 20, 2025

  37 Road To the Plains, Edgartown, MA 02539

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1986

  Last Sold Summary

  • $1,478/SF
  • 40 Days On Market

  Current Estimated Value $2,862,109

  Last Listing Agent Wendy Harman Compass

  37 Road To the Plains, Edgartown, MA 02539
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  Est $1,560,358 Not Listed For Sale

  39 Prices Way, Edgartown, MA 02539

  • 4 Beds
  • 2 Baths
  • 1,532 Sq Ft
  • Built 1986

  39 Prices Way, Edgartown, MA 02539

  Last Sold Summary

  • 18% Below List Price
  • $865/SF

  • Last Sold Price $1,325,000

  Last Listing Agent Stephanie Roache Donnelly + Co.
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  $2,700,000

  • 4 Beds
  • 4.5 Baths
  • 2,750 Sq Ft

  6 Laura's Way, Edgartown, MA 02568

  Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for

  Michele Casavant Vineyard Village Realty

  6 Laura's Way, Edgartown, MA 02568
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  $19,000 Per Month

  • 5 Beds
  • 5 Baths
  • 3,137 Sq Ft
  • House for Rent

  19 Morse St, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all

  Karen Overtoom Karen M. Overtoom R.E.

  19 Morse St, Edgartown, MA 02539
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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 $2,180,617

  Last Listing Agent Stephanie Burke Portfolio Properties

  24 Dark Woods Rd, Edgartown, MA 02539
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  Est $1,993,976 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

  • $1,174/SF
  • 169 Days On Market

  • Last Sold Price $2,000,000
  • Nov 16, 2023

  Last Listing Agent Courtney Marek Sandpiper Realty
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  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,927 Sq Ft

  2 Bold Meadow Rd, Edgartown, MA 02539

  Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a

  Stacy Ickes Donnelly + Co.

  2 Bold Meadow Rd, Edgartown, MA 02539
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  $11,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  15 Price's Way Ed322, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The

  Karen Overtoom Karen M. Overtoom R.E.

  15 Price's Way Ed322, Edgartown, MA 02539
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  $1,175,000 Sold Apr 22, 2026

  112 3rd St N, Edgartown, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft
  • Built 1980

  Last Sold Summary

  • 8% Below List Price
  • $982/SF
  • 139 Days On Market

  Last Listing Agent Kristin Buck Donnelly + Co.

  112 3rd St N, Edgartown, MA 02568
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  Est $1,896,881 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

  • 20% Above List Price
  • $366/SF
  • 3 Days On Market

  • Last Sold Price $1,575,000
  • Feb 25, 2025

  Last Listing Agent Robin Perschel Feiner Real Estate
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  $3,250,000 Pending

  • 4 Beds
  • 4 Baths
  • 1,590 Sq Ft

  99 Cooke St, Edgartown, MA 02539

  LUXURY COTTAGE-STYLE LIVING IN THE VILLAGE – WITH A POOL! This updated classic cottage is located in the heart of Edgartown Village, less than a quarter mile to Main Street. Upon arrival, you are greeted by a spacious porch and elegant French door entry that lead you into the dramatic foyer. The open living plan with kitchen, dining, and living area is light and bright. The first floor opens out

  Bonnie Pierce Wallace & Co. Sotheby's

  99 Cooke St, Edgartown, MA 02539
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  $50,000 Per Month

  • 5 Beds
  • 5 Baths
  • 2,975 Sq Ft
  • House for Rent

  17 Edgartown Bay Rd Ed328, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to

  Karen Overtoom Karen M. Overtoom R.E.

  17 Edgartown Bay Rd Ed328, Edgartown, MA 02539
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  $15,000,000 Sold Mar 31, 2026

  30 Oyster Watcha Rd, Edgartown, MA 02539

  • 4 Beds
  • 5.5 Baths
  • 4,153 Sq Ft
  • Built 1986

  Last Sold Summary

  • $3,612/SF
  • 0 Days On Market

  Current Estimated Value $9,406,008

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

  30 Oyster Watcha Rd, Edgartown, MA 02539
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  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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  $3,995,000

  • 8 Beds
  • 6 Baths
  • 4,651 Sq Ft

  23 Beetle Swamp Rd, Edgartown, MA 02539

  Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you’ll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures with grazing horses.

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  23 Beetle Swamp Rd, Edgartown, MA 02539
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  $80,000 Per Month

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

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $20,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Gorgeous new 4 bedroom 4 bath home. Top of the line finishes and appliances. Gourmet kitchen, screened in porch with fireplace and TV. Pool with swim up bar, hot tub and grilling area. This is a cream of the crop Katama house is a short distance to downtown Edgartown and

  Karen Overtoom Karen M. Overtoom R.E.

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539
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  $5,375,000 Sold Nov 14, 2025

  37 Morse St, Edgartown, MA 02539

  • 4 Beds
  • 5.5 Baths
  • 2,911 Sq Ft
  • Built 1820

  Last Sold Summary

  • $1,846/SF
  • 0 Days On Market

  Current Estimated Value $5,296,308

  Last Listing Agent LINK Email Cache LINK

  37 Morse St, Edgartown, MA 02539
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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
  • Sep 16, 2024

  Last Listing Agent Wendy Harman Compass
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  $3,125,000

  • 3 Beds
  • 2 Baths
  • 1,569 Sq Ft

  309 Barnes Rd, Oak Bluffs, MA 02557

  Your Vineyard summer begins the moment you arrive. This rare, fully furnished waterfront retreat offers 175' of private shorefront on Lagoon Pond — one of Martha's Vineyard's most coveted settings. Taken to the studs in 2022 and reimagined by architect Ramsay Gourd, this bright coastal escape features soaring vaulted ceilings, white shiplap, and painted beams. Glass sliders open to bluestone

  Dawn Bellante Sandpiper Realty, Inc.

  309 Barnes Rd, Oak Bluffs, MA 02557
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  $56,800 Per Month

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

  2 Nonamessett Rd, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool

  Karen Overtoom Karen M. Overtoom R.E.

  2 Nonamessett Rd, Edgartown, MA 02539
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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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  Not Listed For Sale

  3 Duarte Cir, Edgartown, MA 02539

  • 6 Beds
  • 7 Baths
  • 6,783 Sq Ft
  • Built 2023

  3 Duarte Cir, Edgartown, MA 02539

  Last Sold Summary

  • $840/SF
  • 329 Days On Market

  • Last Sold Price $5,700,000
  • Aug 23, 2023

  Last Listing Agent Michele Casavant Vineyard Village Realty

Showing Results 41 - 80, Page 2 of 18