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28 Holly Bear Lane Edgartown MA 02539
Sold

Listing Id 39603

  • Residential
  • Mls Status Closed
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 0.5017

NEW CONSTRUCTION - EDGARTOWN - JUST COMPLETED and READY FOR SUMMER OCCUPANCY! 5 BEDROOMS, 5 BATHROOMS. 30' x 14' HEATED SALTWATER Swimming POOL. Located on a half acre lot, on a quiet street in Edgartown, within a short distance of Sengekontacket Pond, the boat landing on the Boulevard and only 2 miles to Downtown Edgartown. This expanded Colonial has an open floor plan, yet with clearly defined living spaces. Five (5) bedrooms, one on the Ground Floor w/private bathroom & walk in closet, Five (5) bathrooms - (4 full, 1 half), three of which are Private Suites. Ground floor living level has a wood clad ceilings w/fireplace, custom kitchen cabinetry, oversized upper cabinets, some with glass, under cabinet lighting, large kitchen island, Bosch® stainless steel appliances, marble counter tops, Breakfast Area, Dining Room, Powder Room & Laundry. Oak hardwood floors throughout w/tiled bathrooms. Ground Floor Suite with Direct Exterior Access to Patio and POOL. Second story has Four (4) bedrooms, two (2) are Private Suites, each w/their own bathroom & vaulted ceilings. Two (2) additional guest bedrooms, one with a beamed ceiling. Central Forced Hot Air Heat & Air Conditioning. Full unfinished 1,400sq.ft. basement w/9ft.high ceilings. 30' x 14' Heated SALTWATER SWIMMING POOL surrounded by Bluestone patio, stone clad walls and fenced yard. One car Garage. Professional Landscaping and irrigation. (Days on market include construction period).

Listed by Alisan Lohan-Conway of Alisan Lohan-Conway Properties

Listing Sold by Donnelly + Co

$
$
%
$/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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311 East Chop Drive Oak Bluffs MA 02557
Sold

Listing Id 43858

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.25

Arrive by land or sea to 311 East Chop Drive, a truly rare offering that combines panoramic water views in nearly every direction. Perfectly positioned between Vineyard Haven Harbor, Vineyard Sound, and Crystal Lake, this iconic East Chop residence-known as “The Sandpiper”-offers 100 feet of private beach, a 125-foot dock, and an additional mooring, all just minutes from the restaurants, shops and attractions of Oak Bluffs and Vineyard Haven. Completely renovated from top to bottom, this two-story waterfront haven blends the charm of its 125-year history with the modern conveniences of today. Expansive glass sliders and bay windows capture the ever-changing seascape, while hardwood floors, whitewashed beadboard, and a beach-stone fireplace infuse timeless coastal character. With four bedrooms and two and a half baths, the home offers generous space for family and friends. The fully appointed kitchen with breakfast bar invites casual dining and easy gatherings, flowing effortlessly to multiple outdoor spaces designed for relaxation and entertaining. A fenced beach-stone patio and brick terraces lead to a car barn with expansion potential, an outdoor shower, and seaside gardens blooming with rosa rugosa and native grasses. Whether arriving by boat or by car, 311 East Chop Drive offers an unparalleled combination of privacy, convenience, and coastal beauty-an exceptional Vineyard retreat where every day feels like a seaside escape.

Listed by Dawn Bellante Holand,508.524.1601 of Sandpiper Realty

Listing Sold by

$
$
%
$/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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55 The Boulevard Edgartown MA 02539

Edgartown, MA55 The Boulevard

Sale Price$2,832,000

Sold

Listing Id 40736

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 1
  • Acreage 1.74

This RARE AND STUNNING WATERFRONT PROPERTY boasts breathtaking views of Sengenkontacket Pond and State Beach. The property is situated on a spacious 1.74 acre lot with a marshland and a boardwalk overlooking the pond with geese and swans. Enjoy your afternoon kayaking the pond or sailing over to the beach as well as clamming. The outdoor deck is perfect for viewing of the gorgeous morning sunrises; offers plenty of space for entertaining guests, relaxing in the sun or enjoying the cool sea breeze. The adorable ranch is well-maintained and features elegant original oak floors and lovely wood finishes throughout. The main living area maximizes the natural light and stunning views with large windows and sliding glass doors leading to an outdoor deck which allows you to take in the beauty of the surroundings from every angle. The original kitchen has custom cabinetry, stainless steel appliances and ample counter space. The adjacent dining room is the perfect place to savor meals while enjoying the serene views of the water. The 3 bedrooms feature large windows and are all on the first floor. They are supported by a hall bathroom. There is access to the unfinished basement from the primary bedroom. The home also offers an unfinished attic. Updates for 2023: new asphalt shingle roof, new double walled oil tank, new hot water heater, new thermostats, newly refinished floors This truly exceptional property offers a unique and luxurious waterfront living experience and has been in the same family for 75 years. It is the perfect oasis to escape the hustle and bustle of everyday life and enjoy the natural beauty of the water.

Listed by Jennifer B. DaSilva of Compass | Point B

Listing Sold by Martha's Vineyard Buyer Agents

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$
%
$/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 Whistling Swan Circle Edgartown MA 02539
Sold

Listing Id 40548

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 4.5
  • Acreage 0.52

Located in the exclusive Island Grove neighborhood, this perfectly maintained 4,218 square-foot Edgartown retreat is conveniently located near Morning Glory Farm, Downtown Edgartown, and South Beach. The home was designed with entertaining in mind. The first floor offers a den, custom kitchen, a large dining room, living room, half bathroom, and screened porch, all while flowing seamlessly to the outdoor living areas. In addition, there is a first-floor primary bedroom with a large walk-in closet and a full bathroom. The second floor offers two massive bedrooms, two full bathrooms, and a bonus room. The lower level provides a hangout room with a gas fireplace, wet bar, and full bathroom. Highlights include access to the neighborhood association tennis courts, two laundry rooms, two car garage, four-zone heating and cooling system, and mature landscaping. Town sewer serves the property, allowing up to six bedrooms. Come live the Edgartown lifestyle you have always dreamed of.

Listed by Jarrett Hurwitz of Keller Williams Realty

Listing Sold by Keller Williams Realty

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$
%
$/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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26 Caleb Pond Road Edgartown MA 02539
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Listing Id 37305

  • Residential
  • Mls Status Closed
  • Village Chappy
  • Bedrooms 3
  • Bathroom 3

Imagine a Day in the Life at 26 Caleb's Pond Road. Wake up to the gentle breeze, the sounds of birds, and the sea lapping against the shore line in this waterfront retreat. Then enjoy a cup of coffee on the front deck facing east for the sunrise. There's so much to do - or enjoy doing nothing at all. At one end of the property is some of the best clamming in all of MV. At the other end is your deepwater dock with floating dock for boating, fishing, kayaking, paddle boarding, and more. Want to head into Edgartown for dinner, shopping, or just to enjoy the village buzz? It's a short boat ride over to the town landing, and the Chappy ferry is just a mile away. In the evening, relax on your upper deck overlooking Edgartown Harbor, Katama, and South beach. Enjoy dinner or cocktails with friends as you watch technicolor sunsets. This 3-level home takes full and creative advantage of space sleeping a total of 10. The casual beach decor is exemplified by the shell fireplace. This is a magical destination home with a front row seat to one of the most scenic waterscapes on the Eastern seaboard.

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

Listing Sold by Wallace & Co. Sotheby's

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$
%
$/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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1 Marchants Path Edgartown MA 02539

Edgartown, MA1 Marchants Path

Sale Price$2,803,000

Sold

Listing Id 41700

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.5

Experience luxury living at 1 Marchants Path, a spacious and modern home with classic coastal charm in downtown Edgartown. BRAND NEW hardwood flooring in the expansive primary suite and hardwood throughout. Boasting spacious living areas, a gourmet kitchen with stainless appliances and Quartz countertops and island eat-in. Beautifully appointed outdoor living perfect for relaxation, covered Mahogany deck with Teak furnishings and two outdoor showers. Detached artist shed. Attached one-car garage. Conforming 1/2 acre parcel with connected town wastewater allow for expansion with approvals. Located near Edgartown beaches, shops, and dining, this home offers unmatched convenience and privacy.

Listed by Allison Cameron Parry of Douglas Elliman MV

Listing Sold by Martha's Vineyard Buyer Agents

$
$
%
$/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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8 Boston Hill Road Chilmark MA 02535

Chilmark, MA8 Boston Hill Road

Sale Price$2,800,000

Sold

Listing Id 36621

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

Within walking distance to Chilmark center and Quitsa boat landing,this 4 bedroom home with beautiful grounds and water views of Menemsha Pond has a light filled interior rising above the in-ground pool. The center of the home with soaring cathedral ceilings has a unique open staircase which leads to the second floor Master bedroom en-suite with study and private sunning deck. Creative designed open living, kitchen and dining areas overlook the pool from every room. 6 bedroom septic provides for 2 additional bedrooms or guest house.

Listed by Natalie Conroy of Conroy & Company R.E.,Inc.

Listing Sold by Conroy & Company R.E.,Inc.

$
$
%
$/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 Main Street Edgartown MA 02539

Edgartown, MA37 Main Street

Sale Price$2,800,000

Sold

MLS Number 42810

  • CommercialSale
  • Mls Status Closed
  • Bathroom 2
  • Bedrooms 2
  • Half Baths 2

This historic commercial property, built in 1790, is ideally situated in the vibrant heart of Downtown Edgartown. Currently functioning as a blend of retail and residential units, it presents remarkable opportunities for diverse ventures. The property combines exceptional Main Street frontage with a large open lot that abuts Edgartown's primary downtown commons, the Village Green. Whether you aspire to establish your own business or take advantage of the rental market, this property offers an exceptional chance for both ownership and investment that should not be overlooked.

Listed by Cassie Courtney of Wallace & Co. Sotheby's

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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7 Katama Farm South Edgartown MA 02539
Sold

MLS Number 36087

  • MultiFamily
  • Mls Status Closed
  • Village Katama
  • Bedrooms 6
  • Bathroom 4

Katama. Rare opportunity! 4 Bedroom Main House and 2 Bedroom Guest House on 1.5 acres bordering Katama Farm on 2 sides and within a 5 minute walk to South Beach. Both houses are built in the Upside down style to take advantage of the views and incredible sunsets. Spacious second story decks on both houses welcome you to relax to the sounds of the Atlantic Ocean while reading, sunbathing or entertaining. The houses are nicely set apart to allow privacy for both. Each house has been well maintained with many improvements through the years including renovation of the Main House in 2018. This is an opportunity that does not come available often. Great potential for a family compound or rental investment. Excellent rental history for both houses. Being sold Turnkey. Zoning is R60 Multi Houses.

Listed by Linda Hathaway of Seacoast Properties

Listing Sold by Seacoast Properties

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$
%
$/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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12 Trapps Pond Road Edgartown MA 02539
Sold

Listing Id 33503

  • Residential
  • Mls Status Closed
  • Village Sengy
  • Bedrooms 4
  • Bathroom 2

Over 10 special acres stretching from Beach Road to the waters of Trapps Pond - all less than a mile away from Edgartown village. This property is sub-dividable and has been approved by the planning board of Edgartown (see subdivision plan in documents). The cottage at the water's edge is charming, and from just yards away from the deck you can set off to explore the pond by kayak, paddle-board, or dinghy. The birdlife here is extraordinary, and so are the sunsets over the barrier beach from Nantucket Sound. This waterfront property will be the setting of family memories for generations to come.

Listed by Bonnie Pierce 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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8 Tanglevine Road Chilmark MA 02535

Chilmark, MA8 Tanglevine Road

Sale Price$2,800,000

Sold

Listing Id 40395

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 4.3

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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96 Algonquin Avenue Vineyard Haven MA 02568
Sold

Listing Id 41506

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 1.18

Location, location, location! Beautiful, fully furnished* architect designed year-round home with 3 BR, 2.5B, a/c, generator, full walkout basement, 6 BR septic, custom details and finishes plus the bonus of an additional Town approved half acre building lot. Minutes to the village, close proximity to West Chop Club with beautiful sunsets at the flagpole, Mink Meadows Golf Course, West Chop Woods 84 acre preserve, Vineyard Haven Yacht Club, Tashmoo Town beach, Town dock, pier with boat landing, tennis, and pickleball courts. With southern orientation and lots of glass the 6 bedroom Title 5 septic system affords numerous possibilities for expansion. The tiled foyer with double coat closets opens into the open living area with propane fireplace, custom cabinets, large screen TV plus entertainment equipment, bookcases, half bath, Maple floors, kitchen area with Viking range, Corian counters, bar sink, breakfast bar, dining area accented with Striped Bass motif light fixture made by local Menemsha coppersmith, two sliding doors to the expansive back deck plus sliding door to the breezy screen porch, first floor primary bedroom with slider to the deck and outside shower, walk-in closet, full bath with double vanity, walk-in tile shower, plus separate home office with glass pane pocket doors. The second floor landing affords space for family to relax, read, watch TV, exercise, create a home office (or convert to fourth bedroom), plus two more bedrooms with vaulted ceilings - one with large walk-in closet, the other two closets, full bath with tile tub/shower plus skylight, walk-in finished owners' closet, and extra storage in the eaves. The full walk-out basement includes a workbench, shelving, a safe, south facing windows, and French doors opening onto the subgrade patio and offers a multitude of uses for expanded living. This is a unique offering for a single-family year round home with 6 BR septic plus it's Town approved plan for division of the land for a future building lot and offers possibilities for a multi-generational family compound for a second home or a guest house plus room for a pool. *Seller's list of Furnishings available upon request. New owners to register the Town approved Plan should they wish to develop or sell the buildable lot.

Listed by June Flake c. 508.294.8098 of Viewpoints

Listing Sold by Viewpoints

$
$
%
$/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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