Martha's Vineyard, MA Homes

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  $6,395,000

  • 6 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  400 Barnes Rd, Vineyard Haven, MA 02568

  Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

  Jennifer DaSilva Compass | Point B

  400 Barnes Rd, Vineyard Haven, MA 02568
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  /26

  $18,000 per month plus fees

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  40 Lighthouse Rd, Aquinnah, MA 02535

  Great water view property in Aquinnah - this immaculate contemporary has that unique combination of a beautifully designed and constructed, year-round home, AND an outstanding view of the Sound and Elizabeth Islands. Not only is the water view property packed with many custom details, but the home's layout is perfect for relaxed living - with a fantastic kitchen open to the dining and living

  Karen Overtoom Karen M. Overtoom R.E.

  40 Lighthouse Rd, Aquinnah, MA 02535
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  /24

  $665,000 Sold May 23, 2025

  • 806 Sq Ft
  • $825/SF
  • 171 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1876

  51 Rural Cir, Oak Bluffs, MA 02557

  The Spirit of '76 is a lovely Campground cottage nestled into the landscape for privacy and shade. Just a couple of blocks to the beach, town center, shops, and restaurants. A fabulous wrap around porch with various seating areas. Built in 1876 this wonderful throwback of yesteryear features some original furnishings included in the sale. With a classic front parlor, dining room, and kitchen, a

  Lisa Lucier Anchor Realty of Martha's Vineyard

  51 Rural Cir, Oak Bluffs, MA 02557
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  /41

  Est $2,006,915 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,803 Sq Ft

  7 Tar Barrel Rd, Aquinnah, MA 02535

  7 Tar Barrel Rd, Aquinnah, MA 02535
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  /41

  $3,600,000

  • 3 Beds
  • 4 Baths
  • 2,500 Sq Ft

  27 Clambelly Rd, Chilmark, MA 02535

  A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

  Julianna Flanders Flanders Real Estate

  27 Clambelly Rd, Chilmark, MA 02535
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  /15

  $40,000 per month plus fees

  • 6 Beds
  • 3 Baths
  • 1,704 Sq Ft
  • House for Rent

  120 Eastville Ave Ob520, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. Watch the boats come and go from the harbor while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom guest house also offers your own dock and mooring.

  Karen Overtoom Karen M. Overtoom R.E.

  120 Eastville Ave Ob520, Oak Bluffs, MA 02557
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  /27

  $1,600,000 Sold May 22, 2025

  • 1,594 Sq Ft
  • $1,004/SF
  • 532 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1933

  2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

  Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the

  Carol Shore Donnelly + Co

  2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
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  /22

  Est $1,087,284 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,025 Sq Ft

  10 Saddle Club Rd, Edgartown, MA 02539

  10 Saddle Club Rd, Edgartown, MA 02539
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  /52

  $3,750,000

  • 5 Beds
  • 6.5 Baths
  • 4,372 Sq Ft

  139 Main St, Vineyard Haven, MA 02568

  Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses--now gracefully combined into a single half-acre parcel--this home offers rare space, privacy, and timeless character in one of the island's most approachable villages. From the moment you step through the welcoming

  Leslie Floyd Portfolio Properties

  139 Main St, Vineyard Haven, MA 02568
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  /15

  $30,000 per month plus fees

  • 3 Beds
  • 3 Baths
  • 2,888 Sq Ft
  • House for Rent

  101 Peasepoint Way Ed324, Edgartown, MA 02539

  THIS IS A SUMMER RENTAL ONLY. This grand and stately home is located in Starbuck Point in Edgartown. The home is elegantly furnished with traditional charm . The Captain's house is surrounded by neatly manicured lawns and the ocean is at the end of the street. It is a five minute walk to the Edgartown Village and Harbor for shopping, dining or theater.

  Karen Overtoom Karen M. Overtoom R.E.

  101 Peasepoint Way Ed324, Edgartown, MA 02539
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  /13

  $1,195,000 Sold May 22, 2025

  • 1,110 Sq Ft
  • $1,077/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  34 10th St S, Edgartown, MA 02539

  This charming 3 bedroom, 2 bathroom ranch-style Edgartown home offers comfortable single-level living with classic Vineyard appeal. The layout includes a dedicated living room, and an open kitchen and dining area. The primary suite features a private bath, while two additional bedrooms share a full bathroom. Outside, the property provides deck overlooking the yard for enjoying the outdoors.

  Rose Ryley Sandpiper Realty Inc

  34 10th St S, Edgartown, MA 02539
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  /32

  Est $1,169,241 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft

  10 Elm St, Vineyard Haven, MA 02568

  10 Elm St, Vineyard Haven, MA 02568
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  /26

  $3,695,000

  • Land
  • 6.7 Acres
  • $551,493 per Acre

  32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535

  Discover an exceptional opportunity with this rare combination of two abutting parcels spanning more than 6 acres in a coveted location offering water views and Atlantic Ocean private beach access. Surfers and fishermen delight in this location! The Stonewall Association is a beloved area of Chilmark in a supreme location for easy Chilmark living close to the Chilmark Store, the Chilmark

  Jill Napior Tea Lane Associates

  32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535
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  /13

  $27,000 per month plus fees

  • 4 Beds
  • 3.5 Baths
  • 1,962 Sq Ft
  • House for Rent

  20 Bay Lot Circle Ed323, Edgartown, MA 02539

  THIS IS A SUMMER RENTAL ONLY. Vacation by the beach in a relaxed contemporary home offering fabulous panoramic views of Edgartown Harbor, Chappiquidick, Katama Bay and South Beach. Our Katama Bay home is located off of Edgartown Bay Road at the quiet cul-de-sac,close to the beaches and boat launch access. For those who love the ocean breezes and sandy beaches, there is great sunbathing,

  Karen Overtoom Karen M. Overtoom R.E.

  20 Bay Lot Circle Ed323, Edgartown, MA 02539
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  /36

  $5,500,000 Sold May 20, 2025

  • 3,262 Sq Ft
  • $1,686/SF
  • 295 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1984

  12 Tamarack Ln, Oak Bluffs, MA 02536

  This bright and sunny home has a spectacular waterview overlooking the Eighth Fairway of Farm Neck Golf Course, Sengekontacket Pond and Nantucket Sound. Professionaly designed landscaping with perennial beds and charming brick courtyard add to its ambiance. Included are Farm Neck Golf Club stockholder membership (meaning immediate entry into golf membership), tennis and dock & mooring privileges.

  Betsy Kessler Rutledge Properties

  12 Tamarack Ln, Oak Bluffs, MA 02536
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  /30

  Est $1,378,213 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  88 Hopps Farm Rd, Vineyard Haven, MA 02568

  88 Hopps Farm Rd, Vineyard Haven, MA 02568
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  /25

  $3,200,000

  • Land
  • 19.3 Acres
  • $165,803 per Acre

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

  A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

  Jill Napior Tea Lane Associates

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
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  /12

  $12,500 per month plus fees

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

  138 South Rd, Chilmark, MA 02535

  THIS IS A SUMMER RENTAL ONLY. This newly remodeled 3 bedroom 2 bath has a spacious master bedroom suite, cozy sun room and updated kitchen. It has a great yard with garden landscaping, a perfect spot for outdoor dining. 1.5 miles from Alley's store. 3.3 miles to Lucy Vincent Beach.The bathrooms are fully remodeled. An easy, comfortable house in a central location. Three ceiling fans and 3

  Karen Overtoom Karen M. Overtoom R.E.

  138 South Rd, Chilmark, MA 02535
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  /45

  $1,225,000 Sold May 19, 2025

  • 1,725 Sq Ft
  • $710/SF
  • 338 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  51 Head of the Pond Rd, Vineyard Haven, MA 02568

  Iron Hill, Centrally located with convenient access to Island villages. 3 Bedroom, 2 Bath Ranch on 1.5+ acres. An empty canvas with limitless possibilities. Mature landscaping designed for privacy, aesthetics, and low maintenance. Paved private road access, with generous setback for residence. Bike path, Bus stop, State Forest, & Walking Trails nearby. Association covenants allow up to two

  Bruce Stuart Bruce Stuart and Associates

  51 Head of the Pond Rd, Vineyard Haven, MA 02568
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  /22

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,250 Sq Ft

  33 Summer St, Vineyard Haven, MA 02568

  33 Summer St, Vineyard Haven, MA 02568
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  /13

  $6,750,000

  • Land
  • 2.11 Acres
  • $3,199,052 per Acre

  5 Atlantic Dr Unit 5.2, Edgartown, MA 02539

  Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coastal enclave.

  Deb Levin Studio Realty

  5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
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  /13

  $14,000 per month plus fees

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

  88 Quenames Rd, Chilmark, MA 02535

  THIS IS A SUMMER RENTAL ONLY. This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village, with its General Store (Alley's), Farmer's Market, Artisan's Festivals and Flea Market. This home has been recently updated by its new owners. They have chosen the loveliest colors and simple, appropriate cottage touches. There is a new expansive deck

  Karen Overtoom Karen M. Overtoom R.E.

  88 Quenames Rd, Chilmark, MA 02535
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  /18

  $1,850,000 Sold May 19, 2025

  • 1,428 Sq Ft
  • $1,296/SF
  • 158 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1982

  18 Katama Dr, Edgartown, MA 02539

  Ocean views - Nestled on a quiet corner lot, this classic beach house offers a reverse floor plan and distant views of the Atlantic Ocean over the Katama Plain . The upper level features the common living space including the dining area, kitchen, living room with fireplace, and large powder room. The lower level is where you find the more private spaces, including the primary bedroom suite plus

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  18 Katama Dr, Edgartown, MA 02539
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  /44

  Est $4,738,524 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 5,034 Sq Ft

  59 Hagerty Dr, Vineyard Haven, MA 02568

  59 Hagerty Dr, Vineyard Haven, MA 02568
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  /26

  $1,700,000

  • 2 Beds
  • 0.5 Baths
  • 601 Sq Ft

  108 Bay View Ave, Edgartown, MA 02539

  Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

  Derick Freitas Amaral & Associates Real Estate

  108 Bay View Ave, Edgartown, MA 02539
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  /8

  $56,000 per month plus fees

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

  337 Barnes Rd Ob526, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al fresco or try a nearby bistro or 5 star restaurant----the choice is

  Karen Overtoom Karen M. Overtoom R.E.

  337 Barnes Rd Ob526, Oak Bluffs, MA 02557
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  /18

  $1,200,000 Sold May 19, 2025

  • 2,080 Sq Ft
  • $577/SF
  • 590 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  193 Franklin Terrace, Vineyard Haven, MA 02568

  Perched on a sunny sloping lot, this 3-bedroom, 2-bath year-round home in a quiet established neighborhood is walking distance to the heart of town and close to everything. Septic can accommodate 4 bedrooms. Deck with grilling area and outdoor shower looking over the landscaped side yard. On the main level, open kitchen with a large island. On the lower level, 3 bedrooms, 2 have walkout access. A

  Claire Callagy Compass

  193 Franklin Terrace, Vineyard Haven, MA 02568
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  /15

  Est $1,197,123 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 966 Sq Ft

  73 Leonard Cir, Vineyard Haven, MA 02568

  73 Leonard Cir, Vineyard Haven, MA 02568
• 

  

  /26

  $1,700,000

  • Land
  • 0.96 Acre
  • $1,770,833 per Acre

  108 Bay View, Edgartown, MA 02539

  Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

  Derick Freitas Amaral & Associates RE

  108 Bay View, Edgartown, MA 02539
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  /8

  $12,000 per month plus fees

  • 3 Beds
  • 1.5 Baths
  • 820 Sq Ft
  • House for Rent

  8 Beach Plum Path Ob525, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. This irresistible home is a 3-minute walk away from a deeded, sandy, sheltered beach and only a 5-minute drive to the center of Oak Bluffs and all the fun activities that Circuit Avenue has to offer. The casual getaway has wonderful ambiance enhanced by its soaring ceilings, a wood-burning fireplace, and delightful furnishings.

  Karen Overtoom Karen M. Overtoom R.E.

  8 Beach Plum Path Ob525, Oak Bluffs, MA 02557
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  /26

  $1,850,000 Sold May 14, 2025

  • 2,610 Sq Ft
  • $709/SF
  • 8 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1986

  137 Charles Neck Way, Vineyard Haven, MA 02568

  Fantastic opportunity to buy a two house compound in West Tisbury close to Long Point Beach access. A perfect investment, rental income generator or to host extended family and guests.Two well built houses on 1.6 acres, that have been impeccably maintained by the original owner. Offering a total of 5 bedrooms, 4 bathrooms, 2 outdoor showers and 2 garages. There is a charming garden shed and low

  Rebecca V Conroy Conroy & Company R.E., Inc.

  137 Charles Neck Way, Vineyard Haven, MA 02568
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  /16

  Est $1,516,232 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,380 Sq Ft

  44 Jeremiah Rd, Edgartown, MA 02539

  44 Jeremiah Rd, Edgartown, MA 02539
• 

  

  /13

  $1,150,000

  • Land
  • 2.02 Acres
  • $569,307 per Acre

  00 Old Field Rd, Aquinnah, MA 02535

  The nearby roar of the Atlantic can be heard from this pristine two-acre building opportunity in Aquinnah, ideally located at the end of Old Field Road with easy access from Moshup Trail. A storybook walking path through woods and fields over an easement bordering a majestic beetlebung grove and over a bubbling stream, leads directly to the entrance of cherished Philbin Beach. A thoughtfully

  Katherine Donahue Sandpiper Realty Inc

  00 Old Field Rd, Aquinnah, MA 02535
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  /12

  $13,200 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  8 Lobsterville Rd, Aquinnah, MA 02535

  Uniquely designed, 3-bedroom, 2 full bath contemporary home, divided between three floors and set upon an acre of lush grounds with waterviews overlooking Vineyard Sound and the Elizabeth Islands. Privacy enhanced with large tracts of conservation land nearby and walking distance to Lobsterville Beach.

  Karen Overtoom Karen M. Overtoom R.E.

  8 Lobsterville Rd, Aquinnah, MA 02535
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  /39

  $4,762,500 Sold May 14, 2025

  • 5,103 Sq Ft
  • $933/SF
  • 411 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2024

  69 Division Rd, Edgartown, MA 02539

  Welcome to BRAND NEW CONSTRUCTION!! This gorgeous home sits on a spacious lot in a new 5 home luxury private enclave with breathtaking views of the surrounding pastures. The property offers privacy, a serene and picturesque setting, perfect for those seeking tranquility and natural beauty yet a convenient 1.6 mile distance to Edgartown Village. With meticulous attention to detail, this home

  Jennifer DaSilva Compass | Point B

  69 Division Rd, Edgartown, MA 02539
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  /33

  Est $1,907,483 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,508 Sq Ft

  163 Charles Neck Way, Vineyard Haven, MA 02568

  163 Charles Neck Way, Vineyard Haven, MA 02568
• 

  

  /21

  $1,675,000

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  111 Charles Neck Way, Vineyard Haven, MA 02568

  Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

  Emma Kennedy Sandpiper Realty Inc

  111 Charles Neck Way, Vineyard Haven, MA 02568
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  /8

  $7,900 per month plus fees

  • 3 Beds
  • 2.5 Baths
  • 2,107 Sq Ft
  • House for Rent

  2 Paddock Cir, Chilmark, MA 02535

  Karen Overtoom Karen M. Overtoom R.E.

  2 Paddock Cir, Chilmark, MA 02535
• 

  

  /6

  $4,200,000 Sold May 09, 2025

  • 3,600 Sq Ft
  • $1,167/SF
  • 11 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  20 Mill Hill Rd, Edgartown, MA 02539

  NEW CONSTRUCTION, with POOL, walking distance to EDGARTOWN VILLAGE! Approx. 3,600 square feet of open living space. The Great Room has a dramatic Two Story wall of glass, (sliders and an oversized second story window) that overlooks the 14 x 30 foot IN GROUND POOL. In addition to the dramatic Great Room there is a first floor den/lounge area, a first floor primary-en-suite with views to the pool,

  Michele Casavant Vineyard Village Realty

  20 Mill Hill Rd, Edgartown, MA 02539
• 

  

  /25

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,826 Sq Ft

  7 Curtis Ln, Edgartown, MA 02539

  7 Curtis Ln, Edgartown, MA 02539

Showing Results 401 - 440, Page 11 of 18