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32 Schoolhouse Road Edgartown MA 02539
Sold

Listing Id 37184

  • Residential
  • Mls Status Closed
  • Village Katama
  • Bedrooms 4
  • Bathroom 3.5

GORGEOUS COASTAL-STYLE RETREAT WITH POOL IN KATAMA. Located between Edgartown Village and South Beach, this luxurious island home awaits! The entry opens up to reveal a stunning contemporary layout that is perfect for casual island living and entertaining. The open-designed living areas feature gorgeous hardwood floors, vaulted ceilings, a handsome gas fireplace with custom built-in cabinets and a full wall of French doors and windows that open out onto a mahogany deck and the beautifully landscaped yard with gunite pool, bluestone patio and pergola. The stylish gourmet cook's kitchen features custom milled cabinetry, stone countertops, beautiful tile backsplash and high-end stainless appliances. The first floor also features a spacious and luxurious Owner's Suite with private deck, gas fireplace, walk-in closet and a private bath with double vanity and glass walk-in shower. A beautiful staircase leads from the Main Level to a second-floor loft with bonus sitting area and three bedrooms and two full baths, including a second-floor Owner's Suite with private bath. There is a partially finished lower level space with Game/Billiards Room. This attractive Katama home also has a very strong rental history and furnishings are available separately for a turnkey purchase opportunity.

Listed by Wendy Harman of Compass | Point B

Listing Sold by Compass | Point B

$
$
%
$/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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16 Green Pastures Road Edgartown MA 02539
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Listing Id 38423

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 5.2

This custom Sam Sherman designed home has great flow and comfort for any buyer. Upon entering you are immediately impressed by the custom great room with its cathedral ceiling, open hand hewn beams and oversize stone fireplace. To the right is a powder room for privacy and a separate master bedroom first floor suite. Walking by a custom copper sink wet bar you enter the kitchen which is open and sunny and bathed in a pastoral view of some of the most beautiful grounds of any home on the island. Also, off the great room is a three season porch which also has great view of this beautiful land. The second floor has two nice bedrooms which share a large bath. There is a garage to store two cars and a bonus unfinished room above. The lot is oversize at 5.2 acres and the Green Pastures development also surrounds the property with a large band of conservation. The development also owns the largest dock on Chappy which you have rights to and a mooring comes with the property. This is a well thought out home of comfort and is sited in a well thought out development for an extremely comfortable lifestyle!

Listed by Fred Mascolo of Jane Brown Assoc.

Listing Sold by Jane Brown Assoc.

$
$
%
$/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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50 South Road Chilmark MA 02535

Chilmark, MA50 South Road

Sale Price$2,225,000

Sold

Listing Id 40343

  • Residential
  • Mls Status Closed
  • Bedrooms 5
  • Bathroom 3
  • Acreage 6.4

Authentic and lovely Vineyard homestead on over 6 acres with hedgerow borders and stone walls, this is a special and storied piece of island history. The sweeping views over farm fields are stunning, filling the windows with light and the beauty of this natural rural landscape as it has been for hundreds of years. The 1700s post and beam home was originally a "high double house" and became a three-quarter house with an ell in the 1800s. It retains some original features like wainscoting and ancient wide plank floors. The sturdy barn, which was moved to the property in the early 1900s, is ready for it's next chapter as a work barn again, rec space, studio or entertaining spot. This antique Chilmark home awaits its rejuvenation. The property can support an additional house. Property is being sold AS IS.

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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471 West Tisbury Road Edgartown MA 02539
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Listing Id 40418

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 2.4

COASTAL-STYLE CONTEMPORARY. Set on 2.4-acres and framed by beautifully landscaped grounds, this attractive coastal-style contemporary has been tastefully renovated and is a perfect island retreat for year-round and summer living. The open-designed Great Room features vaulted ceilings, gorgeous hardwood floors and three walls of glass windows and French doors that open onto a three-season porch and an expansive wraparound mahogany deck, perfect for indoor-outdoor living and entertaining. The living area is anchored by an attractive gas fireplace and the beautiful cook's kitchen, which features stainless appliances, stone countertops, wine cooler/beverage center and a center prep island/breakfast bar with counter seating. Recent renovations and upgrades include a new kitchen and new bathrooms, all new carpet, newly refinished hardwood floors, freshly painted interior, and exterior, a fully finished lower level. Split AC/Heat units in every room and basement. There is also central FHW heating. Recently installed Anderson windows & insulation on the porch make it a 3 seasonal area. Recessed lighting in all 1st-floor bedrooms and bathrooms. This attractive property can be enjoyed as-is or there is expansion potential for up to seven (7) bedrooms -- including a Guest House or Carriage House -- and there is plenty of room to add an in-ground pool, hot tub, tennis court, extensive landscaping has been added as well as a refreshed stone drive. Ideally located off the Edgartown-West Tisbury Road, the property would allow signage for an in-home business and there is convenient access to the bicycle path, Morning Glory Farm, Edgartown Village, and Katama/South Beach by way of Meetinghouse Road. There is also a solid rental history in place. Furnishings are included except for some personal items paintings etc.

Listed by Joe Barkett of Compass | Point B

Listing Sold by Compass | Point B

$
$
%
$/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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9 Beetlebung Grove Way Chilmark MA 02535
Sold

Listing Id 42643

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.4

Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light create a warm and inviting atmosphere. French doors open seamlessly to an expansive deck, extending the living space outdoors. Adjacent to the living area, the dining room and well-appointed kitchen flow effortlessly into a fabulous screened porch-perfect for al fresco dining or relaxing in any weather. A cozy den and full bath are thoughtfully tucked off the entrance for additional flexibility. Beyond the kitchen, a spacious mudroom with a separate entrance leads to an outdoor shower and a generous laundry room with built-ins and a sink, offering exceptional functionality for island living. The primary suite is a private wing on the main level, featuring a large walk-in closet, a full bath, and a striking double-sided stone gas fireplace that connects the bedroom to an adjoining office or den with a shiplap ceiling. With direct access to a wrap-around deck, this space is truly the crown jewel of the home. Upstairs, you'll find a large bedroom with a private deck, access to a shared full bath, and two additional bedrooms. The full-length basement, offering over 2,200 square feet, and a detached two-car garage provide ample space for storage, hobbies, or future customization. With a 5-bedroom septic in place, there is room for expansion. Just moments from the Great Rock Bight Preserve, Menemsha, and Chilmark's renowned beaches, this exceptional property captures the essence of up-Island living-private, serene, and quintessentially Chilmark.

Listed by Stephanie Roache of Donnelly + Co

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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437 State Road Aquinnah MA 02535

Aquinnah, MA437 State Road

Sale Price$2,225,000

Sold

Listing Id 40480

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 2
  • Acreage 3.8

Perched on a hill overlooking Menemsha Pond, this single story cottage is the perfect escape. The living and dining area is bright and sunny, facing the pond for dynamic water views and boasting high ceilings and a wide brick fireplace. A cozy, rustic kitchen sits adjacent to the living space, and a short hallway leads to three bedrooms. The grassy yard is spacious and low maintenance, and the deck offers a perfect place to lounge and enjoy outdoor dining with an amazing view.

Listed by Bill Rossi of Compass | MV Team

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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37 Road To The Plains Edgartown MA 02539
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Listing Id 40147

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.04

QUINTESSENTIAL VINEYARD CHARMER. Sited on a private and expansive one-acre lot and surrounded by a natural landscape, this beautiful and classically-styled cape is loaded with Vineyard charm. The welcoming interior features cottage-style detailing including golden yellow pine floors, beaded board paneling, custom built-ins, exposed wood rafters and more! The property was designed with indoor-outdoor living in mind with multiple French doors that open onto inviting porches and an expansive bluestone terrace. There is also a large, 16'x14' screened porch off the main living areas that converts to a three-season room and is a wonderful gathering spot for dining and lounging. This property can be perfectly enjoyed as-is -- and/or with Town Sewer hookup (available at the street) the property can also be expanded to up to seven (7) bedrooms, including a 900-sf Guest House, a detached Carriage House -- PLUS there is plenty of room for an in-ground pool! This property is being offered TURNKEY with all furnishings and contents (less a Seller's exclusions list) and there is rental income history available.

Listed by Wendy Harman of Compass | Point B

Listing Sold by Compass | Point B

$
$
%
$/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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30 Pond Lane West Tisbury MA 02575

West Tisbury, MA30 Pond Lane

Sale Price$2,207,500

Sold

Listing Id 37857

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 1.39

Water views and elegance in West Tisbury. This gracious and impeccably maintained home is in the upscale Deep Bottom Association and offers views of Deep Bottom pond and the rolling pastoral fields of the farm beyond. The elegant and turnkey home is filled with natural light and features an open concept great room, dining space, and chef's kitchen with high ceilings. The kitchen has granite counters and high-end appliances. The living room and dining area offer a fireplace and flow out to the back deck with expansive views of the pond, making it a perfect space for entertaining family and friends. There are three bedrooms and three baths, including a first floor primary bedroom with ensuite bathroom and walk-in closet. In addition there is a bonus room that could be used as an overflow bedroom, office or den. There is a generous first floor laundry room and a large, as yet unfinished basement filled with possibility, and an attached two car garage. The property is 1.4 acres offering room for a pool or home expansion. As part of the Deep Bottom Association in West Tisbury, there is access to walking trails, association tennis, and use of a shared dock on Tisbury Great Pond offering wonderful opportunities for superb fishing, and family fun on the water with kayaks or paddle boarding. MORE PHOTOS PENDING ** Please note that there are leases in place for summer of 2021

Listed by Elle Lash 508-560-1213 of Tea Lane Associates

Listing Sold by Feiner 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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114 Cook Street Vineyard Haven MA 02568
Sold

MLS Number 41872

  • CommercialSale
  • Mls Status Closed
  • Bathroom 2
  • Acreage 0.61

Not listed in LINK.

Listed by LINK of LINK

Listing Sold by LINK

$
$
%
$/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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245 Edgartown Vineyard Haven Road Edgartown MA 02539
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MLS Number 42004

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

Discover an exceptional opportunity at The Triangle in Edgartown with this commercial condominium for sale. Boasting ample parking, coveted high-visibility, and a very convenient location. With its strategic positioning, located at an important junction just off of Edgartown Vineyard Haven Road and within easy range of central Edgartown, it is sure to draw in customers and maximize your business' exposure. Don't miss out on this rare opportunity to secure your place in one of the most sought-after commercial units.

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

Listing Sold by Wallace & Co. Sotheby's

$
$
%
$/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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21 Down Harbor Road Edgartown MA 02539
Sold

Listing Id 34411

  • Residential
  • Mls Status Closed
  • Village Katama
  • Bedrooms 5
  • Bathroom 4

Katama gem not to be missed! It is located in Down Harbor which is well-known for its private association beach on Katama Bay and association dock. The highly desirable location is midway between South Beach and the village. The home itself is in move-in condition. The open-plan living room and kitchen area is the focal point and there is also a formal dining room for when the occasion requires. This is the perfect home for entertaining - there is lots of indoor space that spills out onto a large patio for those warm summer evenings. A three-season porch with adjacent deck is the place to relax with friends and family. There are 5 bedrooms in total, including a master bedroom suite and four additional guest bedrooms. Slips on the association dock are available by lottery; nearby moorings may also be available through the Harbormaster. The path to the association beach and dock is adjacent to the house, and it is just 370 yards to the beach (see images in "Photo Gallery").

Listed by Bonnie Pierce of Wallace & Co. Sotheby's

Listing Sold by Keller Williams 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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29 Llewellyn Way Edgartown MA 02539

Edgartown, MA29 Llewellyn Way

Sale Price$2,200,000

Sold

Listing Id 36661

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 1.04

Set on over one acre of land, this stellar setting overlooks Morning Glory Farm and over 10 acres of Landbank. This custom built home is centered around its spectacular outdoor living spaces that include a large infinity edge pool with beautifully landscaped grounds. Over 3,700 sf of living space occupying 3 floors, with Gourmet kitchen, large vaulted living spaces and wall of glass with views of the property and beyond. Recently tied into town sewer, this lot will accommodate 7 bedrooms per Wastewater. Just off the bike bath and a short hop into town or beach.

Listed by Stacy Ickes of Donnelly + Co

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.

Ask A QuestionMore Details

Based on information submitted to LINKMV as of June 16, 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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