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Edgartown, Massachusetts: Country Homes, Houses, and Rural Real Estate

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$22,500,000 29.3 acres 7 Beds | 8 Baths | 6892 sqft
79 Turkeyland Cove Road, Edgartown, MA 02539 - Dukes County

29.3 acres Edgartown, MA

Rarely does a property of such natural beauty and privacy become available for sale. Undoubtedly one of the most prominent locations on Edgartown Great Pond. The 29 + acres provides majestic water views, easy access to the crashing waves of the Atlantic Ocean and private water frontage on the pond. Family compound opportunities are quite significant. The residence is equally as impressive as the setting. This Vineyard contemporary of 7,000 +/- square foot has 7 bedrooms and 7.5 baths. Amenities include: a heated pool, spacious living room with a large stone fireplace, modern gourmet kitchen, circular dining room overlooking the pond, screened porch with stone fireplace, 2nd floor meeting room, 2 guest wings, stunning master bedroom suite wi
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$20,000,000 5.95 acres 8 Beds | 11 Baths | 10099 sqft
22 Lelands Path, Edgartown, MA 02539 - Dukes County

5.95 acres Edgartown, MA

Magnificent Chappy estate overlooking Katama Bay and surrounded by conservation land. This custom residence is perched high on a hill on 5.95 acres with over 180 degrees of unobstructed water views. Designed for today's lifestyle and technology, the property has numerous amenities which include, an expansive living room for large family gatherings, 4 fireplaces, screened porch, wine cellar, gym, sauna, steam shower, roof top deck, custom woodwork, arched ceilings, 3 car garage and a top of the line gourmet kitchen with adjacent morning room. Offering over 10,000 square feet of luxurious living space, this home features 8 bedrooms and 11 baths. Truly a rare and unique opportunity to own and enjoy a generational quality estate.
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$6,500,000 3 acres 4 Beds | 5 Baths | 5310 sqft
44 Caleb Pond Road, Edgartown, MA 02539 - Dukes County

3 acres Edgartown, MA

A stunning location with more than 300' of sandy frontage on Edgartown Harbor. The deep water dock is 4' wide dock, affording more than 8' depth with two T's and several tie-offs; a harbor mooring is also available. The house was superbly designed to afford views from nearly every room, and constructed with the finest quality materials of the time making it most competitive with today's new construction. The landscaping is simple, focusing on the views overlooking the Harbor, which are incredible. All privately situated at the end of the road yet within close proximity to the village. *A separate property, the Pond House, located on Calebs Pond with 3 acres and a contemporary house is currently used as a guest house for the subject prope
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$5,450,000 3.4 acres 4 Beds | 3 Baths | 3298 sqft
82 Turkeyland Cove Road, Edgartown, MA 02539 - Dukes County

3.4 acres Edgartown, MA

A serene retreat! This 2 house compound on almost 4 acres, offers waterfront living at its best. Set on the 16,000 acre Edgartown Great Pond; with only trees and water in its view, this property offers a private dock, private beach, oak-shaded lawns and expansive decks. Yet, it is only 8 minutes from the restaurants and shops of Edgartown. The contemporary main house is centered around a great room with vaulted ceilings, skylights, a Count Rumford fireplace; and an adjacent dining area - all ideal for both formal and casual entertaining. The open kitchen includes a morning room which transforms the space into a living area. 2 master suites and an additional bedroom complete the first level. The lower level has a guest bedroom with private b
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$3,900,000 4.8 acres 4 Beds | 3 Baths | 1788 sqft
9 Briggs Road, Edgartown, MA 02539 - Dukes County

4.8 acres Edgartown, MA

Stunning views and exceptional privacy on Edgartown Great Pond. The main house is at 1990's contemporary in excellent condition and the guest house sits at the water's edge with exceptional views down the pond to the south. Offering over 400' of frontage and adjacent to and protected by 40+ acres of conservation land. An extraordinary opportunity. The front entry leads to the kitchen, dining and living area - waterviews can be enjoyed from all these area. Two sets of glass doors lead to the expansive deck. Off the entry is a mud room/laundry room. First floor master offers waterviews and has private bath and doors to the outside. One guest bedroom on this level. Two guest bedrooms with shared bath complete the second level.
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$2,495,000 3.01 acres 6 Beds | 5 Baths | 2162 sqft
72 Chappaquiddick Avenue, Edgartown, MA 02539 - Dukes County

3.01 acres Edgartown, MA

Ultimate Chappy Compound With Tennis Court, Pool, Jacuzzi, Pool House & More - Sited on three acres atop Sampson's Hill, with 180-degree views across to Nantucket Sound, this ultimate Chappy compound offers all the amenities for an idyllic island lifestyle. This attractive 6-bedroom, 4.5-bath contemporary features an open-designed Great Room with vaulted ceilings and a full wall of glass to maximize the views. An expansive wraparound deck and large screened porch with Jacuzzi beautifully expand the indoor-outdoor living spaces on two levels of the home. A detached pool house offers bonus space for poolside dining and entertaining. There are also approved plans for a 2-bedroom Guest House (plans and permits included). Established rental hist
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$2,100,000 3.6 acres 6 Beds | 4 Baths | 2559 sqft
20 Litchfield Road, Edgartown, MA 02539 - Dukes County

3.6 acres Edgartown, MA

Simply Stunning. This perfectly appointed Chappaquiddick compound, perched on the shores of Caleb's Pond, is a true rarity. A 3 bedroom main house captures views from almost every room and the substantial 3 bedroom guest house is the perfect complement to this idyllic escape. Watch nature's own screenplay unfold from the comforts of the waters edge, deck or the essential screened in porch. Enjoy shell fishing and fishing in the tranquil waters or a simple kayak paddle around the bend to explore the comings and goings on Edgartown Harbor. Located within close proximity to both ferry and beach, this property can't be missed!
$2,025,000 3.05 acres 5 Beds | 5 Baths | 4025 sqft
1 Quampache Lane, Edgartown, MA 02539 - Dukes County

3.05 acres Edgartown, MA

Located in the exclusive Oyster Pond enclave, this spacious 5-bedroom house offers privacy and seclusion. There is deeded access to a private Atlantic Ocean beach, and the launch area to keep your boat is just 500 yards away. The living space is spread out over 5,000 sq ft. Landscaping is by Donaroma's, with one of the focal points being an arbor covered with climbing roses. The home was designed for multi-generational living, with no fewer than 4 separate sitting areas on the first floor, a third story sitting room with views of Oyster Pond, and a walkout basement rec room, bedroom, and full bath where the kids can run wild. There is a very large first floor master bedroom suite, and on the second floor, three bedrooms and two baths. Above
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$1,395,000 3.7 acres 6 Beds | 5 Baths | 3662 sqft
17 Narragansett Avenue, Edgartown, MA 02539 - Dukes County

3.7 acres Edgartown, MA

Chappaquiddick Compound - House and guest house located within close proximity to the ferry, abutting conservation and offering distant outer harbor views! The reverse style four bedroom main house lives large complete with multiple interior and exterior living areas and an open floor plan. The privacy and separation offered by the two bedroom guest cottage provides the perfect space for friends and family or even a separate rental opportunity - complete with soaring ceilings, full dry basement and porch, it is the perfect compliment to this Chappy retreat. A must see!
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$995,000 4.22 acres 2 Beds | 2 Baths | 1932 sqft
5 Old Pocha Road, Edgartown, MA 02539 - Dukes County

4.22 acres Edgartown, MA

This custom home perched atop a charming drive is a true delight! Warm and welcoming with wood floors and oversized windows, no detail was overlooked in this two bedroom Chappaquiddick retreat. Perfectly appointed, the open floor plan flows effortlessly into the essential screened porch and oversized deck. Sited on over four acres with a four bedroom septic system already installed, there are countless expansion possibilities. Pristine and private, affording endless blue sky and garden views, this home must be seen to be appreciated!
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$895,000 2.8 acres 5 Beds | 3 Baths | 2120 sqft
38 Old Indian Trail, Edgartown, MA 02539 - Dukes County

2.8 acres Edgartown, MA

Classic Edgartown Colonial: Picture Perfect And Private - This classic Colonial is privately set on nearly an acre of land surrounded by perennial gardens and conservation land. You are warmly welcomed by a dramatic two story foyer and a sunlit, open Living/Dining area with fireplace, custom built-ins, hardwood floors and two sets of sliding glass doors which open to a wraparound south-facing deck. The adjacent gourmet kitchen is a cook's delight, with granite counters, breakfast bar, and stainless appliances throughout. A hallway off the kitchen leads to a large first-floor bedroom, that can also be used an office/den, plus a full bathroom and laundry. The second floor has three additional bedrooms, and two full baths, including a large Ma
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$775,000 3 acres 3 Beds | 4 Baths | 1933 sqft
8 Macgregor Lane, Edgartown, MA 02539 - Dukes County

3 acres Edgartown, MA

Tucked quietly off Pocha Road and nestled among acres of conservation, with access to Poucha Pond Reserve and the Cross Chappy Trail, rests a retreat like no other. This perfectly appointed home offers a unique yet functional floor plan affording equal parts privacy and openness. The main portion of the home offers a large living area accented with a wood burning fireplace, a fully equipped kitchen and master bedroom. The sensational screened in porch, serving as an annex and a sanctuary, flows effortlessly to the remaining two guest rooms with their own separate living quarters. A large detached studio, ideal for early morning meditation or the ever-present overflow of guests, is the perfect complement to this Chappy property.