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8 Meshacket Wood Road Edgartown MA 02539
Sold

MLS Number 41073

  • Land
  • Mls Status Closed
  • Acreage 4

PRIME 4 ACRE LOT FOR SALE!! Welcome to an exceptional opportunity to own a slice of paradise in one of the island's most sought after locations. Nested along the picturesque shores of Edgartown, this magnificent land listing offers a chance to build your custom dream coastal retreat: main home of up to 10 BEDROOMS as per Edgartown Board of Health, pool, tennis court, garage, carriage house. This exceptional property showcases stunning lush greenery and mature trees for privacy. Conveniently located a few minutes from beaches, boutique shopping and world class dining. Perc test and utilities are the buyer's responsibility. Don't miss this unique chance to build your island retreat!

Listed by Compass | Point B

Listing Sold by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 Squibnocket Road Chilmark MA 02535

Chilmark, MA7 Squibnocket Road

Sale Price$3,400,000

Sold

Listing Id 36015

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 4.5
  • Acreage 3.81

A Classic Vineyard Farmhouse set amidst the rolling hills and ocean views of Squibnocket. This large 6 bedroom farmhouse contains many original details and is loaded with vintage charm. A rambling home perfect for family and friends to enjoy is located within walking distance of Squibnocket beach. A stone patio overlooks the Atlantic and the sound of the ocean waves surround you. Three working fireplaces, a two car garage and an outbuilding adorn this property. Its location affords privacy yet Chilmark center is only a five minute drive away. Lovely views from nearly every room in the house. This home also has a great rental history. A property to be seen and appreciated. OWNER/BROKER has partial ownership interest.

Listed by Julianna Flanders of Flanders Real Estate

Listing Sold by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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22 Herring Creek Road Edgartown MA 02539
Sold

Listing Id 39585

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.5

NEW CONSTRUCTION, contemporary farmhouse style home with a wrap around deck and outdoor shower. This home features a first floor en-suite bedroom with a full double sink bath, a half bath off the foyer entry, an open kitchen/dining and living room area with a gas fireplace, with the rear wall sporting walls of sliding glass doors from both the dining area and living room area. There is a well designed mudroom area, a large overflow pantry and a built in bench seating area. The second floor offers two en-suite bedroom/baths, a large second floor living room area and a second floor laundry. The finished lower level/basement area offers 1,000 square feet of finished space with half bath! The plot has been designed with a future pool and detached garage in mind. The property is located in Katama, close to the Katama General Store, 1 mile from Main Street in Edgartown Village and 2 miles to South Beach. This NEW CONSTRUCTION is in truly a superlative LOCATION.

Listed by Michele Casavant of Vineyard Village Realty

Listing Sold by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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68 Meeting House Road & 0 Rockrose Path Chilmark MA 02535
Sold

Listing Id 39598

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3
  • Acreage 6.16

Enchanting four bedroom home in the heart of Chilmark. Set amongst the rolling hills between South and Middle Roads, this private residence exudes timeless charm, surrounded by ancient stone walls, gorgeous trees and fabulous landscape/hardscape. The living space includes a sprawling, open floorplan with central kitchen, stone fireplace and views of rolling meadows. Primary and guest bedrooms are well-appointed and set privately. A rooftop deck offers an ideal vantage for sunsets with south westerly ocean view. Recent upgrades include refinished floors, new windows, paint and an open kitchen design - some elements still in-progress though property offered as-is. Over 6 acres of land and existing 5 bedroom septic offer lots of options for any desired changes (note that 2.56 acres are conservation restricted). Ownership in Chilmark allows access to town residents' only beaches at Squibnocket and Lucy Vincent. Make this your Martha's Vineyard destination!

Listed by Peyton Wallace of Compass | MV Team

Listing Sold by Carroll & Vincent R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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141 Lighthouse Road Aquinnah MA 02535
Sold

Listing Id 39674

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 5.3

Panoramic water views and sunset views from this newly constructed beach house on a hill in Aquinnah. Open floor plans with a stone fireplace as the focal point and a wall of windows to the views. Sliders open to a wide entertaining deck. Primary bedroom suite located on the main living level. Three bedrooms, two bathrooms, TV room and laundry located on the walk-out lower level. Ancient stone walls run throughout the expansive property. Extensive stonework, firepit and outdoor shower.

Listed by Meg Bodnar 508-221-2782 of Tea Lane Associates

Listing Sold by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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44 Plantingfield Way Edgartown MA 02539
Sold

Listing Id 41585

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.53

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 buyers. The existing structures could be reconfigured and updated to meet a buyer's specific needs, while the large level lot also presents an excellent opportunity for those looking to start new and create a brand new, custom island retreat or private oasis complete with a pool. This property can be connected to town sewer and support up to six bedrooms with a grandfathered guest house. Located close to shops, restaurants, beaches, and the harbor, the home provides a perfect blend of convenience and privacy - ideal for year-round living, vacation use, or rental potential in one of Edgartown's most sought-after areas.

Listed by David Dickinson of Compass | Point B

Listing Sold by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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56 North Neck Road Edgartown MA 02539
Sold

Listing Id 43647

  • Residential
  • Mls Status Closed
  • Bedrooms 7
  • Bathroom 5
  • Acreage 18.38

A RARE CHAPPAQUIDDICK LEGACY ESTATE WITH BEACH ACCESS- Privacy & Island Living at its finest. Step into a world where time slows, ocean breezes carry the scent of salt and cedar, and each day begins and ends with the relaxing sounds of the local fauna and the Vineyard Sound. This 18.4-acre multi-residence estate, with 4 conforming size parcels, on Martha's Vineyard's treasured Chappaquiddick Island is more than a property-it's a rare opportunity to create a generational legacy in one of New England's most sought-after coastal enclaves. Tucked beside the historic Royal & Ancient Chappaquiddick Links and surrounded by conservation land, this compound offers unmatched seclusion while placing you moments from sandy beaches, island trails, and the gentle rhythm of Vineyard life. Main Residence | 8,335 sq. ft. Chef's kitchen with Viking oven, dual Sub-Zero refrigerators, wine fridge, and granite counters. Expansive decks for morning coffee at sunrise and cocktail hours at sunset. Lower level with wet bar opening to pool and patio; private home office for remote work in paradise. Second Residence | 1,351 sq. ft. - 3 bedrooms, 2 bathrooms, full kitchen, screened-in porch, multi-level deck, and outdoor shower. Bunk House Retreat | 1 bedroom, kitchenette, living area, and full bath - perfect for overflow guests or a quiet getaway. Resort-Style Amenities include a Heated Gunite pool with outdoor shower, a Tennis court for friendly matches and a 4-bay garage with room for all the toys. Multiple parcels offering flexibility for expansion, this property invites you to imagine a lifetime of gatherings, celebrations, and quiet escapes. Opportunities of this scale and privacy on Chappaquiddick are exceedingly rare-and once gone, they may never come again. Ready for its next chapter, this property awaits a discerning new steward to restore its former glory and carry it proudly into the future. Call now to arrange a private tour and experience firsthand what it means to live surrounded by natural beauty, boundless privacy, and the authentic Chappy way of life. NOTE: The images and photographs provided are for illustrative purposes only and may not reflect the current state if the state, features, or furnishings of the property. Prospective buyers are encouraged to conduct their own inspections and due diligence to verify all details prior to making any purchase decisions.

Listed by Leslie C. Floyd 508-221-4643 of Portfolio Properties

Listing Sold by Byrne & Company Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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25 Bold Meadow Road Edgartown MA 02539
Sold

Listing Id 44319

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 1.5

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 guest apartment, there is plenty of space to host friends and family. The current owners have undertaken numerous upgrades including renovating the kitchen and primary bathroom and adding the sunroom. All the improvements have been thoughtfully implemented and make the transitions between the living spaces seamless. There's plenty of elbow room, with opportunity to expand further. The large basement with tall ceilings could be transformed into additional living space such as a media room or gym. The configuration of the lot makes a swimming pool an attractive option should the next owners want one. The lot lives larger than its 1.5 acres, with green belt area on three sides. Guests may be hosted in the 900-sf apartment above the oversized garage. Meticulous attention to detail has been observed in the creation of this oasis less than 3 miles to the village and half that distance to Morning Glory Farm. Thanks to the 30 SunPower solar panels installed by South Mountain, the house is energy efficient, too. If you're looking for a move-in ready home in Edgartown, here it is! Please note: Some images have been enhanced to more accurately represent the property's foliage during the summer months.

Listed by Mark Jenkins of Wallace & Co. Sotheby's

Listing Sold by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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179 Tisbury Lane East West Tisbury MA 02575
Sold

Listing Id 42845

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 2
  • Acreage 10.7

Seven Gates Farm: This warm and convivial home in one of the island's most desirable communities is less than 1/10th of a mile to the private association beach. The house was designed to accentuate indoor-outdoor living; there is generous decking for morning or afternoon sun, and a screened porch which is the perfect place to enjoy shade and breeze after a day spent at one of the nearby beaches. There are views of the water from the second floor. The rolling 10.7-acre lot is spectacular with mature trees, stone walls, and open meadow punctuated by dramatic lichen-covered boulders. Seven Gates owns and maintains two miles of private beaches, two large docks for swimming and boating, two tennis courts, and many miles of walking trails through 1600 acres of unspoiled association land.

Listed by Mark Jenkins of Wallace & Co. Sotheby's

Listing Sold by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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25 Simpsons Lane Edgartown MA 02539

Edgartown, MA25 Simpsons Lane

Sale Price$3,350,000

Sold

MLS Number 42734

  • CommercialSale
  • Mls Status Closed
  • Bathroom 6
  • Bedrooms 6
  • Acreage 0.2

Nestled in the heart of Edgartown, is this historic residence known as The Lightkeeper's Inn. This property has five bedrooms, five baths and a separate one bedroom, one bath cottage, on .20 acre. Beautifully decorated in ole Vineyard style, the residence has the island feel of old time Martha's Vineyard. This 5BD/5BA home sits in the heart of Edgartown close to the waterfront. Known as The Lightkeeper's Inn, this historic Inn was said to be home to Henry Lyman Thomas, one of the last lightkeepers of the Edgartown Lighthouse. The property is unique in that it offers onsite parking, which is a rarity on Martha's Vineyard. Currently operated as an Inn, this property may be converted to a single family residence with the required proper permitting and approvals. It is conveniently located close to Edgartown Ferry, Edgartown Lighthouse, and minutes from N. Water Street, which offers shopping and restaurants.

Listed by Greg Hartel of Hartel Realty

Listing Sold by Hartel Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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24 Sumner Park Road Oak Bluffs MA 02557
Sold

MLS Number 39265

  • MultiFamily
  • Mls Status Closed
  • Bedrooms 12
  • Bathroom 10
  • Acreage 0.2

Unique Multi-Family in East Chop. Four units, 12 bedrooms in total. The units include a 7 bedrooms, 7 bath house - a 3 bedroom, 1 bath house and (2) studio apartments. Zoned B1, this property is a must-see to understand the opportunities it presents. Nestled privately, abutting East Chop Association land and open space in a prime location only a short distance to beaches, harbor, and downtown Oak Bluffs. The primary house is a two-story with 2,520+/- square feet and offers 7 bedrooms and 7 bathrooms, kitchen, open living and dining area and laundry /mud-room. There is tons of decking along the side and rear of the house for outside enjoyment. The back house was built in the 1950's and offers 1,500+/- square feet with 3 bedrooms and 1 bath, kitchen and open living and dining area with two story ceiling height and loft. (2) studio apartments, built in 1996, each offer 520 square feet of space with kitchen and full bath.

Listed by Lesley Heidt of Sandpiper Realty

Listing Sold by Portfolio Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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36-R Pulpit Rock Road Oak Bluffs MA 02557
Sold

Listing Id 41000

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 0.8869

UNIQUE Offering in the Waterview Farm WATERFRONT Community~ A Piece of Paradise ~Wake up on Top of the World with the Sunrise on the sparkling waters of Sengekontacket Pond…offering sweeping views of the rolling meadows and a panoramic seascape over the barrier beach, and Nantucket Sound to Chappaquiddick Island! This exceptional custom design is as functional as it is gracious with over 2300 square feet of airy living space offering intimate settings and lots of glass that captures the natural sunlight and highlights the striking visuals throughout each room….includes a 2 car garage and finished basement (285 sq feet) There are 3 perfectly situated bedrooms starting with a stylish primary suite conveniently located on the first floor, and 2 bedrooms, a tiled full bathroom, and a bright open loft on the second floor…..all displaying unparalleled views. This peaceful and tranquil ambience has an acre of land connecting winding foot paths throughout the common meadows and a scenic access to the sandy waterfront beach, association dock, mooring fields and acres of mature meadow. There is a footpath at the side of the property that is golf club accessible to desirable FARMNECK GOLF & TENNIS CLUB! Exquisite setting call for a private tour!

Listed by Ocean Park Realty Inc

Listing Sold by C McManus Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to LINKMV as of June 15, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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