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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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$3,195,000 11.93 acres 5 Beds | 5 Baths | 4300 sqft
8 Boldwater Road, Edgartown, MA 02539 - Dukes County

11.93 acres Edgartown, MA

Sophisticated Country Estate With Great Pond and Ocean Beach Access. Set on 12 acres in the exclusive enclave of Boldwater, this sophisticated country estate offers all the best of island living. This exquisite property has been perfectly designed to integrate indoor and outdoor living around a pool with bluestone terrace, expansive lawn and gardens. There are a total of five bedrooms, including a spacious first-floor Master Suite and two separate sleeping wings for guest. Enjoy the morning kayaking on the Edgartown Great Pond. Come back to the house and enjoy a dip in the pool and time reading on the outdoor covered porch. Head out in your skiff for a spectacular day at the sandy, private association beach. Opportunity to add a guest hous
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$2,750,000 4.3 acres 4 Beds | 4 Baths | 3582 sqft
63 Kanomika Road, Edgartown, MA 02539 - Dukes County

4.3 acres Edgartown, MA

Casual waterfront home in a tranquil setting with sunsets over the Edgartown Great Pond! This warm and inviting home on Kanomika's west edge offers the perfect summer retreat for your friends and family. Expansive deck and screened in porch makes summer time entertaining a pleasure. This home has an open kitchen and dining area, living room with a beautiful fieldstone fireplace along with a library/tv room. The master bedroom en suite is located on the ground level along with an additional bedroom and bathroom. The second level consists of 2 very large bedrooms and a full bathroom. Store your boating gear and car in the attached garage which also has a large bonus room above. Enjoy the association tennis courts or simply follow the pictures
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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!
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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, Edgartown, MA 02539 - Dukes County

2.8 acres Edgartown, MA

Charming Country Compound On Chappy - Perched on Sampson's Hill, the highest point in Edgartown, this charming Chappy compound features two tastefully updated homes set on 2.8 country acres surrounded by beautiful gardens and wildflowers. The Main House is comprised of an open-designed Great Room which opens onto a large screened porch with lovely garden views. The handsome cook's kitchen features marble counters, and stainless appliances. There is a first-floor bedroom with full bath; the remaining two bedrooms and full bath are located on the second floor. The nearby Guest Cottage also features a screened porch as well as an open living/dining area with vaulted ceilings, full kitchen, and warm hardwood floors, along with two cozy bedrooms
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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.