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149 Litchfield Road Edgartown MA 02539
Sold

Listing Id 42017

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 4
  • Acreage 1.7

Please Note: The contract price was $3,425,000 and $285,000 was allocated for furniture. Set privately in the heart of Chappaquiddick, this property offers a rare combination of exceptional landscaping with a tastefully executed, refined home that exudes quality throughout. While beaches, trails, and even downtown Edgartown are readily available nearby, this property is an oasis unto itself. On the exterior the home greets with elegant New England coastal architectural features and high-end materials, including cedar shingle roof and siding, copper accent, and Azek trim. Multiple entrances lend beautifully to indoor/outdoor living, which allow for enjoyment of the extensive bluestone patios, Ipe deck with soaking tub, flower and vegetable gardens, and comfortable open lawns. The interior spaces are beautifully appointed with a thoughtful layout. The center of the home is a cathedral-ceiling great room, with a fieldstone fireplace and perfect chef's kitchen at opposite ends. The primary suite is private, yet conveniently located to the great room, with a luxurious bathroom, walk-in closets, and soaring high ceilings. Two additional bedrooms are set on a separate wing of the house, each with private bathrooms. A sitting room and finished basement rec. room adjoin the secondary bedrooms. There is also a two-car garage and studio/cabana that is a beautifully finished bonus/guest quarters. Throughout the home, quality is everywhere, featuring hardwood, tile and stone floors, extensive white shiplap, central heating and ac, and oversize windows that provide abundant natural light. Room for in-ground swimming pool if desired. 4 bedroom septic system in the ground. A rare find on Chappaquiddick for buyers looking for a turn-key home fully furnished and in immaculate condition.

Listed by Peyton Wallace of Compass | MV Team

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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188 Pond Road West Tisbury MA 02575

West Tisbury, MA188 Pond Road

Sale Price$3,135,000

Sold

Listing Id 40427

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.9

Elegant Deep Bottom Pond property with oversized lot, heated pool, and further development potential. The association offers manicured paved roads, private tennis courts, deeded Great Pond access with kayak storage, and walking trails in the woods and open meadows. This property features a double lot with 2.9 acres of private outdoor living spaces, gardens and heated pool. Through the front entry, an open and voluminous main living room gives access and views to the pool, deck, and private back yard. The first floor has an open kitchen-dining-living room with a fireplace, cathedral ceiling, and ample windows and glass doors. A first floor guestroom and full hall bathroom are included on this level. Upstairs there are two guest bedrooms with one full hall bathroom. The primary suite is also on this second level with its own private bathroom, and walk in closet. There is a third mezzanine level with twin day bed and sunny skylight. The finished basement level has an open living space, and a small private room. Outdoor shower, deck, covered front porch and pool lounging area complete the exterior.

Listed by Rose Ryley of Sandpiper 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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16 Forever Wild Way Edgartown MA 02539
Sold

MLS Number 40407

  • Land
  • Mls Status Closed
  • Acreage 3.05

Listed by Donnelly + Co

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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110 Fifth Street North Edgartown MA 02539
Sold

Listing Id 42516

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.55

Water views with a pool! This chic contemporary 4-bedroom home with a pool and 2-car garage enjoys the ever-changing water views of Sengekontacket Pond and Nantucket Sound on three levels. Fully renovated, this delightful home, being sold turnkey, is flooded with light, open to breezes, and marries a timeless Vineyard vibe with modern luxury. The mudroom entryway opens to the kitchen with an expansive breakfast island, dining room, and living room with a gas fireplace. Sliders from the living room open to the heated pool and hot tub surrounded by granite pavers. The kitchen shares a view of the pond and Nantucket Sound through the wall of windows and sliders in the dining room out to the deck, a perfect spot for outdoor dining. A wine cooler in the dining room has a pass-through space above it to the adjacent family room. The open floor plan lets the cook connect with family and guests. Beyond the kitchen, accessed through a sliding barn door, is a cleverly placed office with built-in bookshelves and sliders to the deck. A pantry, half bath, laundry, and another mudroom adjacent to the outdoor shower complete the first floor. The views of Sengekontacket and Nantucket Sound become more dramatic on the second and third floors. There are 4 bedrooms on the second floor, including 2 primary suites, all with vaulted shiplap ceilings, as well as a den and a shared bath. The den and one of the suites have private decks that capture the essence of the views. A second sliding barn door opens to the den, creating a private primary wing at the front of the house. An outstanding spiral staircase provides access to the fabulous “Lookout Lounge,” where you will enjoy exceptional views inside and outside on 2 decks. The professionally landscaped yard includes a perennial garden, mature trees and shrubs, and a rolling lawn with a fire pit. It's only steps away from the hiking trails of Felix Neck Wildlife Sanctuary, a short trip to the town landing, and an easy drive or bike ride to downtown Edgartown. With ample spaces for relaxation, entertainment, and multiple living areas, this home is the perfect Vineyard experience.

Listed by Stephanie Roache of Donnelly + Co

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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140 Pond Road West Tisbury MA 02575

West Tisbury, MA140 Pond Road

Sale Price$3,120,000

Sold

Listing Id 42713

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.43

Welcome to this beautifully updated and privately situated home in one of West Tisbury's most desirable associations. Residents enjoy exclusive access to tennis courts, walking trails, horse pastures and Tisbury Great Pond. Designed for both comfort and luxury, this spacious 4+ bedroom, 3 bathroom property is ideal as a year-round residence or upscale vacation retreat. The first floor features a sun-filled living room with soaring ceilings, an ample dining room, a spacious bedroom with a cozy fireplace, and a chef's kitchen outfitted with brand-new Thermador appliances. From the front covered porch, you enter a large foyer; the side porch leads into a generous laundry room for easy island living. Multiple decks and a screened-in porch with windows for three-season living create seamless indoor-outdoor flow. Upstairs, the private primary suite includes a spa-like bathroom with a jetted tub, walk-in shower, large walk-in closet, and its own private deck-perfect for morning coffee or stargazing. The finished basement offers a sauna for relaxing after a beach day or trail hike, a large TV viewing area, and extra space for guests. Recent upgrades: brand-new roof, fully net-neutral solar system, all-new insulation, new heating and cooling systems (ducted heat pump), new kitchen appliances, and a Lutron RadioRA home automation system. The professionally landscaped yard includes a lush, irrigated lawn and provides complete privacy-just minutes from Tisbury Great Pond, Edgartown, the West Tisbury Farmers Market, and more. This is Vineyard living at its finest-perfect for making lasting memories. Furnishings available for purchase. Owner and tenants in residence until end of August 2025.

Listed by Jon Hartzband 508-415-4239 call/text anytime of Martha's Vineyard Island-Wide Realty

Listing Sold by Compass | The O'Hanlon 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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74 North Water Street Edgartown MA 02539
Sold

Listing Id 35817

  • Residential
  • Mls Status Closed
  • Village Downtown
  • Bedrooms 7
  • Bathroom 3.5

The Captain Henry Pease II House, dating back to the 1830's, has been nicely maintained and restored to preserve most of the historic details and character. Many nice features include beautiful wide planked pine floors, original molding, built-ins, finish details and six fireplaces. The spacious eat in kitchen has been tastefully renovated with modern amenities that include french doors that lead out to a brick patio and a private and beautifully maintained yard. The perfect spot for summer dining and entertaining. Upon entering the front entrance, there is an entryway with a curved staircase, a traditional front parlor, family room and formal dining room, each with fireplace. The second floor includes 2 guest bedrooms, each with fireplace, that share a full bath. The master has it's own en-suite bath with shower and soaking tub, fireplace and access to a second floor summer porch that offers nice water views of the Edgartown Harbor. A perfect spot for relaxing. A finished third floor with an additional 2 bedrooms and full bath. Easy access to the Edgartown Harbor, the Village and the Lighthouse.

Listed by Brenda Galligan of Karen M. Overtoom R.E.

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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34 Pond View Way Vineyard Haven MA 02568
Sold

Listing Id 33663

  • Residential
  • Mls Status Closed
  • Village Lagoon
  • Bedrooms 3
  • Bathroom 4.5

When a premier builder builds his own home, he applies all the innovative and state-of-the-art qualities, appointments, and technology he has made for his clients over the years. It becomes the best of the best in every respect. This home is that property. The term "over the top" is applicable here. Combining this with the impeccable taste of his wife is a win/win situation. Not only is the home remarkable but the landscaping, the views, and access to the private beach on the Lagoon enhance an already unique property. There are custom cabinets and woodwork throughout the home, each ceiling has a different height and design, and the study/office curved ceiling made of fir bead board. The 8' high custom entrance door and custom sized windows distinguish the building. Ledge stone used at the outside entrance rolls into the interior dining room, living room, and kitchen. The kitchen is as remarkable as the balance of the house. A pizza oven, 2 dishwashers, a Thermador Column System for refrigeration and floor to ceiling wine cooler further demonstrate the details of the house. The kitchen opens to a comfortable den with wood burning fireplace and corner windows overlooking the water. An efficient built in bar is between the den and living room for easy entertaining. A gracious hall takes you by the covered deck with outdoor dining and the office/den with open views of the Lagoon. The luxurious master suite is in the south wing of the house with a fireplace, private deck and outdoor shower and an exceptionally designed bath, laundry area, and closet space. The lower level has direct water views from every room. It is dedicated to the guest area with two en suite bedrooms, a sitting area, an extraordinary second laundry area, closet storage, general storage and access to the two car garage. This description only touches the surface of the incomparable property and the superlative attributes, and has to be seen in person to appreciate the comfortable elegance throughout the home. Click on the video tour in the listing under External Links for a preview! (4 Bedroom septic system.)

Listed by Stephanie Roache of Sandpiper Realty

Listing Sold by Vineyard Village 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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138 Edgartown Vineyard Haven Road Oak Bluffs MA 02557
Sold

Listing Id 39430

  • Residential
  • Mls Status Closed
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 1.2

Luxury home very close to perfection with an oversized privately located lot in the center of the island includes most of the items in your checklist. Spectacular heated shotcrete pool with both a jacuzzi and a stone water fall is surrounded by a thermal bluestone deck. Adjacent to the pool is a stone fire pit perfect for gatherings, this backyard has all the bells and whistles. A beautiful fruit/vegetable garden includes pears, apples, blueberries, and strawberries. A large shed great for storage sits right next to the kids swing set playground, and you still have plenty of room in the yard perfect for entertainment. As you walk in the main house you find yourself amazed with the open concept full of luxury finishes in every corner. Large Master suite includes heated marble floors, and an attached three season porch. Entire house was recently renovated, including a high end finished basement! Solar panels come in handy to help assist with the continuing increase of the energy costs. Above the oversized heated newly constructed 3 car garage you will find a high end one bedroom apartment, and a separate art studio that can be also used as a home office if needed. This is the listing you have been waiting for!

Listed by Antulio Goncalves 774-232-0059 of Premiere Broker Inc

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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20 Paddock Road Oak Bluffs MA 02557

Oak Bluffs, MA20 Paddock Road

Sale Price$3,100,000

Sold

Listing Id 38915

  • Residential
  • Mls Status Closed
  • Bedrooms 5
  • Bathroom 5.5
  • Acreage 2.02

Almost 5000 sq ft of brand-new construction tucked nicely on a beautiful lot in the prestigious subdivision of "The Preserve". This home meets all the modern buyer's needs with its open floor plan, 1st, and 2nd-floor master bedroom suites, chef's kitchen, hardwood floors throughout, custom tile bathrooms, expansive outside entertaining space, and lush landscaping. With its generous living spaces, this home is ideal for entertaining friends and family. There is also lots of opportunity for privacy, thanks to the separate bedroom suite and bathroom above the garage. This is the summer house of your dreams, and can also be your escape during the cooler months thanks to the modern, efficient systems. This spectacular home will be the ideal place to host large family dinners at Thanksgiving or the holiday season with the fireplace as the perfect setting to gather around at the end of the day.

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

Listing Sold by The Agency

$
$
%
$/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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10 Basin Road Chilmark MA 02535

Chilmark, MA10 Basin Road

Sale Price$3,100,000

Sold

Listing Id 43524

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 3
  • Acreage 1

Unique compound in the heart of Menemsha - one of a kind! The cottage (520 sq.ft.), the chandlery buikding(5968 sq.ft.) and deli with an apartment(2172 sq.ft.) on just under an acre of land has tremendous potential for the right buyer! Special permits are required from the town to operate a business but they have approved a deli/restuarant, small stores and a commercial kitchen in the past. Work has been begun but not completed at this time.

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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80 Edgartown Bay Road Edgartown MA 02539
Sold

Listing Id 41499

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.97

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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3 Down Harbor Road Edgartown MA 02539
Sold

Listing Id 43358

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1

Exceptional Opportunity in Down Harbor. Here's a rare chance to own a property in Edgartown's exclusive Down Harbor community. Known for its serene setting and prime access to Katama Bay, this neighborhood offers more than just scenic beauty- Ownership includes deeded rights to a pristine, sandy association beach, along with coveted mooring and dock privileges on Katama Bay - a benefit typically reserved only for direct waterfront estates. Down Harbor is renowned for its tranquility and timeless appeal, attracting discerning homeowners who value understated luxury and proximity to the water. The neighborhood is experiencing a renaissance of elegant new construction and high-end renovations, further elevating its status among Martha's Vineyard's premier destinations. The existing residence features four bedrooms and three bathrooms, complemented by a two-car garage with an artist's studio above. With town approval, a new six-bedroom septic system may be installed, allowing the home to be expanded accordingly-offering exceptional flexibility for customization and future enhancements. Set on a full acre of mature, thoughtfully landscaped grounds, the property provides a tranquil and private setting. Whether you choose to enjoy the home in its current form or customize it to suit your personal vision, the possibilities are as inspiring as the surroundings.

Listed by Susie Wallo 508-776-6050 of Compass | The O'Hanlon Group

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.

Ask A QuestionMore Details

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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