Sale Price$14,000,000
MLS Number 40582
Beautiful custom built home in a prime location on Plantingfield Way. Very spacious 6,345 square foot house with garage. Designed with modern decor and style, this luxurious property will not disappoint! A must see.
Listed by Paul Pertile of The Agency
Listing Sold by Donnelly + Co
Sale Price$14,000,000
MLS Number 39255
One of the most exquisite waterfront settings on Martha's Vineyard's south shore with breath taking views over meadows and dunes out to the Atlantic Ocean. Walk out your door to 1200 feet of private sandy association beach shared with just the homeowner's who own the eight lots in the Homer Watcha Homeowner's Association. This 22 acre property consists of two separate lots and, should a buyer desire, offers the opportunity to create a family compound with multiple homes and accessory structures. Lot 5A with house (assessed at $11,406,600) is 13.4 acres and abutting vacant Lot 5B (assessed at $4,611,100) is 8.8 acres . Constructed in 1985, this solidly built, year-round architecturally designed home embraces the easy beach lifestyle which this property represents. All of the rooms offer sunlight and ocean views. The house is designed with three different wings which are connected by decks on the first and second floor. This playful approach to island living allows for great communal spaces as well as privacy. This home has a new heating system and a full house generator, both installed in 2021. A buyer will have the option of renovating a very special home or of building a new home(s) of their own design. This property also shares ownership in 40 acres of communal land as well as 141 acres of association conservation land with walking trails. The surrounding conservation protects the value of this sought after private enclave while creating a sense of seclusion and closeness with nature. This one-of-a kind setting in West Tisbury is convenient to Edgartown and the airport yet in a world of its own.
Listed by Abby Rabinovitz cell 617-429-4561 of Tea Lane Associates
Listing Sold by Sandpiper Realty
Sale Price$13,128,000
MLS Number 42559
Located in the heart of historic North Water Street lies this classic 8-bedroom home on an oversized lot with a deep-water pier. The largely original, 1860's building represents one of the last untouched Edgartown harbor front homes. The first floor features a water facing living room, dining room and wonderful wide covered porch, all with amazing views of Edgartown Harbor and Chappaquiddick. The second floor has two water facing master suites, four smaller bedrooms and the third floor has additional living space with two bedrooms, bath and storage. The formal street side landscaping offers a boxwood lined brick path to the front doorway and includes three oversized parking spaces. The water side offers gorgeous, formal gardens surrounding a patio, brick garden walls and an expansive lawn leading to the private pier and the ornamental boathouse. This is an amazing opportunity to acquire a significant harbor front home with boating access, located blocks away from the historic downtown area. Please call to view this very special Edgartown harbor front property.
Listed by Gerrett Conover of Landvest MV
Listing Sold by Landvest MV
Sale Price$13,000,000
MLS Number 34264
Located in the exclusive Herring Creek Farm Association and offering over 10,000 square feet of exquisitely appointed living area, lies this magnificent waterfront estate. The classic architecture is complimented by the well-executed floor plan. The ground floor offers wonderful living spaces including a grand entrance with dining room, gourmet kitchen, family room and screened porch to one side, and a living room, sunroom and den to the other. There is a ground floor suite plus 5 additional 2nd floor bedrooms including a luxurious master suite. The residence is complimented by an attached 3-car garage with parking courtyard, a large pool and patio area and a open porch with stone fireplace. The beautifully landscaped grounds offer sunset views across the pond and barrier beach as well as expansive views across the open fields and stable to the east. The common association land offers over 100 acres of open fields, a horse stable and over 1,500 feet of private Atlantic beach. Complete privacy, a luxurious turn-key house in a amazing setting, with private beach and all within a short drive to downtown Edgartown, makes this property one of the island's finest.
Listed by Gerrett Conover of Landvest MV
Listing Sold by Wallace & Co. Sotheby's
Sale Price$13,000,000
MLS Number 35460
Situated on over 15 waterfront acres on the Edgartown Great Pond, you will enjoy breathtaking views in a truly unique and special setting in Herring Creek Farm. The 5,500+ sq ft main house features hardwood floors, exposed wood beams, six bedrooms, a fitness center, great floor plan, an expansive outdoor patio and stunning water views. The recently built chic guest cottage sits privately next door with three bedrooms, three baths, an open kitchen/living space, deck and gorgeous lawn. Both homes take advantage of a winding boardwalk that leads to your private access to the Pond. Herring Creek Farm also provides homeowners with access to the private association barrier beach on the Atlantic Ocean. This is truly a special opportunity to create a waterfront compound to have for generations to come.
Listed by Thomas Leclair of Landvest MV
Listing Sold by Landvest MV
Sale Price$12,900,000
MLS Number 36618
Truly a once in a lifetime chance to live in one of Edgartown's most desirable locations. Only one of five homes in this exclusive enclave, you have a front row seat to watch the activity of the outer harbor, lighthouse, sailboats, Chappy Beach Club-a 180 degree view. This home embodies all of what in-town Edgartown living is, a quiet winding street, waterfront, walk to town and the beach. Easy in and out of town access without the hassle of traffic. This classic Shingle Style home has been meticulously restored to preserve its exquisite design details. There is a lovely living room with grand views over the water and an intimate seating area near the fireplace. You will find a spacious open dining room to a beautifully paneled billiards room and half bath. The kitchen is well designed and feels open to the house but does allow for privacy if one wanted, a clever design. There are multiple bedroom suites upstairs for generational living as well as a privately sited guest cottage. A two car garage has ample space for boat storage and cars. Enjoy all that Edgartown has to offer with the ease of this location and historic beauty of this home.
Listed by Jill Hobby Napior 508-642-0831 of Tea Lane Associates
Listing Sold by Wallace & Co. Sotheby's
Sale Price$12,865,000
MLS Number 37601
Not listed in LINK.
Listed by LINK of LINK
Listing Sold by LINK
Sale Price$12,600,000
MLS Number 40680
This classically styled home lies on a large prominent North Water Street lot overlooking the Edgartown Lighthouse and the entrance to the Harbor. The home was newly built in 1995 and recently renovated, with all in excellent condition. The house features a large split-level dining/living room with tall ceilings and a fireplace, all leading to a large deck with some of the best views in the harbor. There are 3-bedrooms / 3-baths. There are plans in place that would add a 4th bedroom. Completing the property is a expansive yard leading to private beach with deep-water pier capable of holding up to 10 boats.
Listed by Thomas Leclair of Landvest MV
Listing Sold by Landvest MV
Sale Price$12,500,000
MLS Number 43093
This dramatic contemporary styled house lies on 6.5-acres of beautiful pond front land in the exclusive Herring Creek Farm. The home features cathedral ceilings throughout and an open floor plan with large living room, dining room and kitchen, all with clear story light, fireplaces and 20 ft. breakaway Nana walls. The spiral staircase leads from the living room to a large roof deck with expansive views of the South Shore. There are 5 suites all with luxurious bathrooms, closets, and private garden terraces. Additionally, there is an attached carriage house with 3 additional bedrooms, a billiards room and exercise room. The grounds offer a large, stunning pool, a 12 person Jacuzzi, outdoor kitchen, and parking courtyard. There is a high level of finish throughout, a whole house Lutron control system and advanced audio/video. Herring Creek Farm offers direct access to private South Shore beach and over 150 acres of conserved land.
Listed by Gerrett Conover of Landvest MV
Listing Sold by Landvest MV
Sale Price$12,250,000
MLS Number 39326
Not listed in link
Listed by Landvest MV
Listing Sold by Landvest MV
Sale Price$12,145,000
MLS Number 38839
This classic shingle styled home is located on 2.1 acres of prime water frontage in the exclusive Cow Bay Association. The 4 bedroom, 4 ½ bath main residence designed by Patrick Ahearn is tastefully appointed throughout and features a grand foyer, den, gourmet kitchen / family room, formal dining room and large screened porch. There is a two bedroom guest house, expansive lawns and formal gardens. Homeowners in Cow Bay jointly own common land and over 2000 feet one of the islands premier beaches. Privacy and a pristine setting yet 5 minutes to downtown Edgartown, makes this area very special.
Listed by Gerrett Conover of Landvest MV
Listing Sold by Compass | MV Team
Sale Price$12,000,000
MLS Number 40823
Welcome to your dream waterfront oasis on Vineyard Haven Harbor! This exceptional custom home offers an unparalleled blend of luxury, serenity, and captivating water views. Situated on a sprawling beach front parcel, this residence boasts an array of incredible features that epitomize coastal living at its finest. Step inside and be greeted by the seamless flow of the open-concept living space, designed to maximize both comfort and style. The interior is bathed in natural light, courtesy of the expansive windows that showcase panoramic views of Vineyard Haven Harbor. The gourmet kitchen is a chef's delight, featuring top-of-the-line appliances, custom cabinetry, and a spacious island. The adjacent sitting area features a fireplace and French doors leading to a screened porch. The primary bedroom suite boasts stunning water views, a spacious walk-in closet, and a luxurious en-suite bathroom. The additional guest bedrooms are generously sized, each offering its own unique view of the harbor or the lush surroundings. For those seeking relaxation and recreation, this property offers an outdoor paradise. Step outside to discover meticulously landscaped grounds, an expansive stone patio and pool, perfect for lounging or al fresco dining, while relishing the breathtaking scenes of the ferry passing by. One of the true highlights of this remarkable residence is its private beach, providing exclusive access to the pristine shoreline on Vineyard Haven harbor and allowing for easy boating access. A two-car garage offers ample storage for vehicles and outdoor equipment. Located on Main Street, you'll have easy access to the charming shops, galleries, and restaurants in Downtown Vineyard Haven. Live the waterfront lifestyle you've always dreamed of in this extraordinary home.
Listed by Alyssa Halisky of Wallace & Co. Sotheby's
Listing Sold by Landvest MV
Based on information submitted to LINKMV as of June 13, 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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