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100 South Road Chilmark MA 02535

Chilmark, MA100 South Road

Sale Price$1,260,000

Sold

Listing Id 33322

  • Residential
  • Mls Status Closed
  • Village South
  • Bedrooms 4
  • Bathroom 3

Classic features blend seamlessly with modern sensibilities in this expanded Cape Cod-style home. With double the square footage of the original and updated for the 21st-century lifestyle (including a first-floor master suite), this home is perfect for year-round living or as an all-seasons Vineyard retreat. The property adjoins acres of untouched woods, providing ample privacy, while remaining easily accessible throughout the year on a town-maintained paved road. First floor consists of formal living room with fireplace, separate dining room, master suite with large sitting room and private screened-in sunroom, laundry room, additional bedroom and bath, kitchen, 650 sq. ft. mahogany deck for outdoor entertaining, and sun-filled, 530 sq. ft. great room with 14' ceiling, exposed antique beams and radiant floor heating for the ultimate in winter comfort. Second floor contains two large bedrooms with cozy dormer alcoves, and full bath. Oversized two-car garage with built-in work bench. 1500 sq. ft. basement provides lots of storage space, additional refrigerator and freezer, and second laundry room. The many updates and improvements include new well, architectural-shingle roof, cedar-siding shingles, HVAC, Title V septic system, top-quality insulation, upgraded electrical and plumbing, and energy-efficient Marvin windows and French doors throughout. This home is turn key. Beautifully furnished right down to the grand piano!

Listed by Brenda Codding of Up Island Realty

Listing Sold by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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 Teaberry Lane Edgartown MA 02539

Edgartown, MA25 Teaberry Lane

Sale Price$1,260,000

Sold

Listing Id 37862

  • Residential
  • Mls Status Closed
  • Village Sengy
  • Bedrooms 4
  • Bathroom 3

Craftsman style contemporary Cape with many recent improvements, including fresh exterior paint. Almost 2,000 sq. ft. of living space with partially finished basement (adds another 600 usable sq. ft.) Plus... a 1-year old free-standing 3 bay garage (with radiant floor heat so if perfect for any type of workshop) has a fully equipped and furnished 1 bedroom apartment above! Can you say income producer? Soooo many options here. Main house is finished with wood floors, open staircase to 2nd floor, vaulted ceiling in the dining room, stainless steel appliances in the captivating kitchen and a wonderful wood stove in the sun-room . The rear deck is so inviting that you won't want to spend any time indoors. There is a "grassy" green yard (with irrigation) that has plenty of room for games and the rich soil in the garden is enhanced by the adjoining chicken coop. This is a unique opportunity in a great Edgartown location close to the town Landing on Sengekontacket Pond for kayaking, shell-fishing and more.

Listed by Doug Reece of RE/MAX on Island

Listing Sold by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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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71 State Road Vineyard Haven MA 02568
Sold

Listing Id 36675

  • Residential
  • Mls Status Closed
  • Village Downtown
  • Bedrooms 4
  • Bathroom 6.5

A truly spectacular residence with rooms of gracious proportion and grand scale, plentiful natural light, modern amenities, and exquisite craftsmanship in a recent renovation. Includes over 3800 sq. ft. of living space, a gourmet kitchen with professional appliances, dining room, spacious living room with fireplace, home office, walk-in pantry and powder room on the main level. The second floor features 4 bedrooms each with en-suite baths including a master bedroom suite with private porch and 2 full baths. The fully finished lower level includes a digital projection theatre with state-of-the-art surround sound, a rec-room with stunning brick detail, sauna, full tile bath, bunkroom, and laundry room with double washer/dryers. An inviting bluestone patio surrounded by gardens adorns the rear of the property and is perfect for outdoor entertaining. Beautiful gardens, outdoor shower and stone fireplace complete this outdoor oasis. A special place, 71 State Road awaits a new owner to enjoy gracious living while being close to Downtown Vineyard Haven shops, restaurants, harbor and ferry. Ample off-street parking.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

Listing Sold by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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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23 Pine Tree Lane Vineyard Haven MA 02539
Sold

Listing Id 42838

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.49

Not listed in LINK.

Listed by LINK of LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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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11 Flamingo Drive Edgartown MA 02539

Edgartown, MA11 Flamingo Drive

Sale Price$1,260,000

Sold

Listing Id 42996

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.5

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 room is open to the tiled eat-in kitchen area and the hallway leads to a pantry, full bathroom and two first floor bedrooms. The second floor offers a full bathroom and two generously sized bedrooms. The interior has been completely painted and sparkles brand new with new paint on ceilings, walls, windows, doors, baseboard heaters, and all trim. Brand new carpeting in the first-floor hallway and bedrooms. Do not miss the opportunity to purchase this great investment! *Seller credit to Buyer at time of closing of $30,000 to help with closing costs!

Listed by Skip Dostal of Martha's Vineyard R.E.

Listing Sold by Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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 Plum Bush Point Road West Tisbury MA 02575
Sold

MLS Number 43385

  • Land
  • Mls Status Closed
  • Acreage 4.12

This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle. The large, flat building envelope offers many siting possibilities and, should you choose, the property is grandfathered for a 1000 sq ft guesthouse, could also support a 900 sq ft ADU and offers room for a barn, pool and/or studio as well. Create an expansive meadow and open gardens or keep a more wooded feel. The sought after Plum Bush Point neighborhood is located between two large conservation preserves, the 91-acre Short Cove Preserve and the 173 acre-Sepiessa Point Reservation. Launch your kayak or small boat from the Sepiessa Point Reservation just around the corner. This is a wonderful piece of land in a special location…private and close to nature yet convenient to West Tisbury town center and centrally located on the island, essentially equidistant from here to Menemsha Harbor, Edgartown Main Street and Tisbury Main Street. This property provides natural beauty and easy access to all the Vineyard has to offer, including access to Lambert's Cove Beach. Spend your day hiking miles of walking trails or exploring the waters and beaches of the South Shore, Tiah's Cove and Tisbury Great Pond, and then come home to your private and quiet country retreat.

Listed by Tea Lane Associates

Listing Sold by Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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 Plum Bush Point Road West Tisbury MA 02575
Sold

MLS Number 40903

  • Land
  • Mls Status Closed
  • Acreage 4.12

This 4.12 acre wooded parcel is situated with easy access just around the corner from the entrance to the coveted Sepiessa Point Preserve with its beautifully conserved waterfront, kayak and boat launches onto Tiah's Cove and the Tisbury Great Pond and miles of hiking trails. A well is in place and a perc test approved by the Town of West Tisbury for a 5-bedroom house. The parcel is also grandfathered for a possible guest house providing an opportunity to create a spectacular family compound in a special West Tisbury location.

Listed by Stoney Hill Realty

Listing Sold by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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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11 Jordan Way Edgartown MA 02539

Edgartown, MA11 Jordan Way

Sale Price$1,250,000

Sold

MLS Number 37704

  • Land
  • Mls Status Closed
  • Village Downtown
  • Acreage 1.27

Foreclosure

Listed by LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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 Motick Trail Edgartown MA 02539

Edgartown, MA7 Motick Trail

Sale Price$1,250,000

Sold

MLS Number 37998

  • Land
  • Mls Status Closed
  • Acreage 1.5

Not listed in LINK.

Listed by LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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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4 Lagoon Pond Road Vineyard Haven MA 02568
Sold

MLS Number 36843

  • CommercialSale
  • Mls Status Closed
  • Village Downtown
  • Bathroom 1
  • Acreage 0.0918

The best location on the Island for visibility! This working Bike Rental and Sales Business has the attention of every car that drives off the Vineyard Haven Ferry! Selling Bikes, Electric Bikes and bicycle paraphernalia this is a ready made business waiting for the next buyer to take the "helm". A once in a lifetime opportunity !

Listed by Fred Mascolo of Jane Brown Assoc.

Listing Sold by Jane Brown Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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 Evelyn Way Vineyard Haven MA 02568
Sold

MLS Number 42575

  • CommercialSale
  • Mls Status Closed
  • Bathroom 0.5
  • Half Baths 1
  • Acreage 0.26

Not listed in LINK.

Listed by LINK of LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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.

Ask A QuestionMore Details

2 Pilots Landing Aquinnah MA 02535

Aquinnah, MA2 Pilots Landing

Sale Price$1,250,000

Sold

Listing Id 31823

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 3.2

A sublime contemporary take on the perfect beach house, or, the absolutely perfect year round retreat. Designed by award winning architect Charles Rose, whose ultra modern concept of three living area pavilions separated by grass courtyards and a roof deck with sweeping ,excellent views,of the Vineyard Sound and Elizabeth Islands, satisfies all the senses.The central locus is living room, dining room and kitchen.The front of the building is immense glass sliding doors, with large screen doors which can slide into place to convert the living room into a screened porch in communion with the gardens outside.The master suite and bath is separated by its own courtyard for privacy.Two additional bedrooms and full bath guest house has its own grassy courtyard to define its area apart.The house is designed to accommodate multi functions while preserving privacy in each area.The house sits above one of the Island's most coveted north shore beaches .This seaside gem has won many accolades and can be viewed in publications: Barefoot Beach Houses, Metropolitan Home, The Houses of Martha's Vineyard, to name a few. Definitely delve into the amazing and savvy body of work for Charles Rose Architects at www.charlesrosearchitects.com. For those who want to enjoy the views, and a very special communion with Nature in one of its most sacred places.

Listed by Lucinda Buehler Schweikert of Feiner Real Estate

Listing Sold by Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 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.

Ask A QuestionMore Details

Based on information submitted to LINKMV as of June 21, 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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