Martha's Vineyard, MA Homes

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  $2,650,000

  • 6 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  63 Crowell Ln, Vineyard Haven, MA 02568

  Extraordinary West Chop Opportunity - Two Homes on 1.80 Acres in Vineyard Haven Nestled next to the desirable West Chop/Mink Meadows neighborhoods, this unique property features two dwellings, making it a perfect opportunity for multi-generational living, guest accommodations, or rental potential.The welcoming, farm-style front porch on the main house looks out onto a large yard. Inside, the

  Heather Dyas-Fried Tea Lane Associates

  63 Crowell Ln, Vineyard Haven, MA 02568
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  /8

  $8,000 total monthly price

  • 4 Beds
  • 4.5 Baths
  • 3,600 Sq Ft
  • House for Rent

  56 Chilmark Rd, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and

  Karen Overtoom Karen M. Overtoom R.E.

  56 Chilmark Rd, Chilmark, MA 02535
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  /18

  $995,000 Sold Nov 06, 2025

  • 990 Sq Ft
  • $1,005/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1983

  2 Flamingo Dr, Edgartown, MA 02539

  Dodger's Hole - Traditional ranch style home with 3 bedrooms and 1 bath, set upon a half acre, corner lot located within a mature association neighborhood. A comfortable outdoor deck and outdoor shower completes the Vineyard experience. Convenient to the waters of Sengekontacket, and immediate access to bikes paths leading to the villages of Edgartown, Oak Bluffs and Vineyard Haven.

  Sean Federowicz Landmarks at TODAY Real Estate

  2 Flamingo Dr, Edgartown, MA 02539
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  /20

  Est $1,519,817 Not Listed For Sale

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

  39 Prices Way, Edgartown, MA 02539

  39 Prices Way, Edgartown, MA 02539
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  /52

  $2,575,000

  • 4 Beds
  • 2.5 Baths
  • 1,910 Sq Ft

  76 Washque Ave, Edgartown, MA 02539

  This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends

  Katherine Donahue Sandpiper Realty Inc

  76 Washque Ave, Edgartown, MA 02539
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  /42

  $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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  /30

  $2,240,000 Sold Nov 06, 2025

  • 1,764 Sq Ft
  • $1,270/SF
  • 27 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  29 Pradas Way, Edgartown, MA 02539

  THE PERFECT KATAMA RETREAT. Located just one mile from South Beach and steps from the bike path connecting Edgartown Village and the shoreline, this charming Katama property offers the ultimate Vineyard lifestyle. Beautifully built in 1998 by a respected Island contractor, this well-maintained home sits privately among soaring pines and welcomes you with a classic farmer’s porch. Inside, the

  Wendy Harman Compass | Point B

  29 Pradas Way, Edgartown, MA 02539
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  /14

  Est $2,461,695 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,926 Sq Ft

  30 Pond Ln, Vineyard Haven, MA 02568

  30 Pond Ln, Vineyard Haven, MA 02568
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  $2,195,000

  • 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 Massachusetts, LLC

  34 Davis St, Tisbury, MA 02568
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  /27

  $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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  /19

  $835,000 Sold Nov 05, 2025

  • 960 Sq Ft
  • $870/SF
  • 119 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2000

  1 Onondaga Ave, Oak Bluffs, MA 02557

  Charming Single Story Cottage on a Beautiful Oak Bluffs Lot – Perfect for Your Vineyard Retreat! Discover the timeless appeal of this cozy 1-bedroom, 1-bath home nestled on a spacious 0.31-acre lot in the heart of Oak Bluffs. Built in 2000 and lovingly owned by the same family since its inception, this property offers a fantastic opportunity for both comfortable living and future expansion.

  Leslie C. Floyd Portfolio Real Estate, Inc.

  1 Onondaga Ave, Oak Bluffs, MA 02557
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  /36

  Est $1,179,160 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  16 Rock Pond Rd, Vineyard Haven, MA 02568

  16 Rock Pond Rd, Vineyard Haven, MA 02568
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  $2,195,000

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  15 Night Heron Rd, Edgartown, MA 02539

  KATAMA - NEWLY RENOVATED! This Quintessential Martha’s Vineyard saltbox blends timeless island character with wonderful thoughtful updates, having been recently renovated. Set in a quiet location, Island Grove, one of the most popular locations in Edgartown, you're just a short drive to Wilson's Landing, South Beach and downtown Edgartown, an ideal location for summer escapes, year-round living,

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  15 Night Heron 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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  /42

  $1,700,000 Sold Nov 03, 2025

  • 2,558 Sq Ft
  • $665/SF
  • 118 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1986

  35 Tower Ridge Rd, Oak Bluffs, MA 02557

  Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

  Katherine Donahue Sandpiper Realty Inc

  35 Tower Ridge Rd, Oak Bluffs, MA 02557
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  /40

  Est $1,720,934 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1 Sq Ft

  179 Main St, Vineyard Haven, MA 02568

  179 Main St, Vineyard Haven, MA 02568
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  /28

  $2,495,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  268 Tashmoo Ave, Vineyard Haven, MA 02568

  Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

  Michele Casavant Vineyard Village Realty

  268 Tashmoo Ave, Vineyard Haven, MA 02568
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  /18

  $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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  /28

  $1,260,000 Sold Nov 03, 2025

  • 1,820 Sq Ft
  • $692/SF
  • 182 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2002

  11 Flamingo Dr, Edgartown, MA 02539

  Located in the Dodger's Hole subdivision is this inviting four bedrooms plus office, two-bathroom cape style home. The property has been well cared for and is a delight to view. Sited on .5 acres of land with a pea stone driveway, wraparound deck, and outdoor shower with new enclosure. The antique garage is a great storage space for lawn equipment, garden supplies or small vehicle. The living

  Skip Dostal, Jr Martha's Vineyard Real Estate

  11 Flamingo Dr, Edgartown, MA 02539
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  /23

  Est $1,944,920 Not Listed For Sale

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

  31 Pulpit Ln, Edgartown, MA 02539

  31 Pulpit Ln, Edgartown, MA 02539
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  /30

  $2,490,000

  • 3 Beds
  • 4 Baths
  • 2,830 Sq Ft

  42 Deacon Vincent Way, Edgartown, MA 02539

  Katama ~ Turnkey Retreat in Edgartown Estates. Located on a quiet, paved road in sought-after Edgartown Estates, this meticulously maintained home offers the perfect blend of privacy, space, and convenience. Ideally positioned equidistant to South Beach and downtown Edgartown, and just moments from the bike path. The home features a bright vaulted-ceiling living room with a gas fireplace and an

  Stephanie Roache Donnelly + Co.

  42 Deacon Vincent Way, Edgartown, MA 02539
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  /25

  $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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  /31

  $3,750,000 Sold Oct 31, 2025

  • 1,274 Sq Ft
  • $2,943/SF
  • 380 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2009

  29 Oxcart Rd, Aquinnah, MA 02535

  Waterfront beach house on Dogfish Bar in Aquinnah. Take in the beauty of this gem of a location with rolling dunes, waterviews and immense sunsets! This property is one of only a few homes on this stretch of private and preserved beach. This 2009 contemporary beach house offers a reverse floor plan with the entire top floor as the living area, kitchen & dining, and more windows than walls to

  Michelle Kelly Tea Lane Associates

  29 Oxcart Rd, Aquinnah, MA 02535
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  /48

  Est $2,869,894 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  8 Coffins Field Rd, Edgartown, MA 02539

  8 Coffins Field Rd, Edgartown, MA 02539
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  /19

  $2,675,000

  • 3 Beds
  • 1.5 Baths
  • 1,540 Sq Ft

  5 Ocean View Farm Rd, Chilmark, MA 02535

  Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

  Natalie Conroy Conroy & Company R.E., Inc.

  5 Ocean View Farm Rd, Chilmark, MA 02535
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  /15

  $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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  /2

  $5,900,000 Sold Oct 31, 2025

  • 3,143 Sq Ft
  • $1,877/SF
  • 0 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1849

  12 Squibnocket Rd, Chilmark, MA 02535

  Not Listed in LINK

  LINK Email Cache LINK

  12 Squibnocket Rd, Chilmark, MA 02535
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  /49

  Not Listed For Sale

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

  670 State Rd, Vineyard Haven, MA 02568

  670 State Rd, Vineyard Haven, MA 02568
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  /42

  $2,375,000

  • 6 Beds
  • 4.5 Baths
  • 2,970 Sq Ft

  128 W Spring St, Vineyard Haven, MA 02568

  A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street - Two adjacent properties being sold together create a flexible compound just moments from downtown Vineyard Haven. The 4-bedroom, 2-1/2 bath main house also includes a separate, 1-bedroom in-law/nanny apartment with a full bath. The guest house has 1 bedroom and 1 bath, with a 4-bedroom septic system allowing

  David Dickinson Compass

  128 W Spring St, Vineyard Haven, MA 02568
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  /26

  $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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  /16

  $1,135,000 Sold Oct 31, 2025

  • 1,344 Sq Ft
  • $844/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  30 Teaberry Ln, Edgartown, MA 02539

  Well-maintained three bedroom, 2 bath home on a level .51 acre lot. Primary en-suite and open floor plan offers the best in first-floor living. Large unfinished basement, outdoor shower and recent Title V inspection of the four bedroom septic system. Deck overlooks the spacious backyard with room for a pool. Convenient to shellfishing or kayaking in Sengekontacket, Caroline Tuthill Preserve and

  Dawn Bellante-Holand Sandpiper Realty

  30 Teaberry Ln, Edgartown, MA 02539
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  /35

  Est $1,162,460 Not Listed For Sale

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

  29 Dunham Ave, Vineyard Haven, MA 02568

  29 Dunham Ave, Vineyard Haven, MA 02568
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  $2,375,000

  • 6 Beds
  • 4.5 Baths
  • 2,970 Sq Ft

  128 & 136 Spring St, Vineyard Haven, MA 02568

  A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street—two adjacent properties being sold together to create a unique, flexible compound just moments from the Tisbury School and downtown Vineyard Haven. With a spacious main residence and a separate guest house, this rare combination presents a compelling opportunity for multigenerational living, seasonal enjoyment,

  David Dickinson Compass | Point B

  128 & 136 Spring St, Vineyard Haven, MA 02568
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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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  $1,100,000 Sold Oct 31, 2025

  • 1,900 Sq Ft
  • $579/SF
  • 91 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1999

  145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

  Enjoy effortless island living in this beautifully renovated 3-bedroom, 2.5-bath condo, tucked within a quiet and well-maintained association. Thoughtfully updated with modern finishes and quality craftsmanship, this spacious unit offers comfort, style, and functionality. The open-concept living area features a cozy wood pellet fireplace, perfect for cooler evenings, and flows seamlessly into a

  Emily Flake Viewpoints

  145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568
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  /75

  Est $3,405,343 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,362 Sq Ft

  4 Tilton Rd, Chilmark, MA 02535

  4 Tilton Rd, Chilmark, MA 02535
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  /36

  $2,500,000

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft

  16 South Rd, Chilmark, MA 02535

  Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been updated

  Michele Casavant Vineyard Village Realty

  16 South Rd, Chilmark, MA 02535
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  /3

  $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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  /12

  $37,500,000 Sold Oct 30, 2025

  • 16,209 Sq Ft
  • $2,314/SF
  • 0 Days On Market

  • 9 Beds
  • 9.5 Baths
  • Built 2000

  48 Witchwood Ln, Edgartown, MA 02539

  Every nice town has an iconic property that is widely considered the most special and this property might just be it. From the moment one enters the driveway, you’re captured by the extraordinary landscaping, the expansive lawns and the general Gatsbyesque feeling that sweeps over you. The drive through carriage house, the symmetry of the classic architecture and courtyards and the spectacular

  Gerrett Conover Landvest MV

  48 Witchwood Ln, Edgartown, MA 02539
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  /52

  Est $5,803,013 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,740 Sq Ft

  12 Plantingfield Wood Cir, Edgartown, MA 02539

  12 Plantingfield Wood Cir, Edgartown, MA 02539

Showing Results 121 - 160, Page 4 of 18