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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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$13,800,000 6.56 acres
16 Bayside North, Edgartown, MA 02539 - Dukes County

6.56 acres Edgartown, MA

BAYSIDE - The most significant offering on Katama Bay with 6.5 acres creating an expansive waterfront compound with over 380 feet of frontage. A boardwalk over marsh allows for a scenic trespass to the shoreline and permits are in place for a private deep water dock. There are several home sites fronting on the bay that will provide spectacular water views to the south while encompassing the natural meadow to the west. The topography is varied with rolling hills and open grassland. This new enclave in Katama was created to embody and preserve the natural character of the old Vineyard. With over 20 acres of protected open space of native meadow and forest land, the result is an unparalleled setting and the assurance of owner privacy. Additio
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$12,950,000 4.4 acres
18 Bayside South, Edgartown, MA 02539 - Dukes County

4.4 acres Edgartown, MA

BAYSIDE ~ A select offering of 4.4 acres with over 320' of sandy beach and a private deep water dock on Katama Bay. The gentle rise of the topography presents commanding views of the water and the home site provides the opportunity to build a 10 bedroom compound and accessory structures. This new enclave in Katama was created to embody and preserve the natural character of the old Vineyard. With over 20 acres of protected open space of native meadow and forest land, the result is an unparalleled setting and the assurance of owner privacy. Additional parcels also available - please inquire
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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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$6,500,000 3.15 acres 4 Beds | 4 Baths | 3790 sqft
55 North Neck Road, Edgartown, MA 02539 - Dukes County

3.15 acres Edgartown, MA

This private three-acre property on prestigious North Neck offers a charming, winding driveway, sprawling landscaped lawn, deep-water dock, and spectacular views of the Edgartown harbor, lighthouse and waterfront. This classically-designed home offers a spacious kitchen that opens to a large deck, patio and grilling areas - perfect for entertaining, a formal dining and living room, a fabulous screened porch, den, and four bedrooms including a luxurious master suite. The detached three-car garage and two-bedroom carriage suite complete this perfect setting. This is a truly rare and special offering that must be seen to be appreciated.
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$5,450,000 3.4 acres 7 Beds | 5 Baths | 3358 sqft
82 Turkeyland Cove Road, Edgartown, MA 02539 - Dukes County

3.4 acres Edgartown, MA

Rare Find In Katama: Waterfront Compound With Pond, Dock And Private Beach Access. Located at the end of a private winding drive and set on over three bucolic acres, this spectacular waterfront property is comprised of a Main House plus Guest House -- with a total of seven bedrooms -- making it an ideal family compound or rental property. Both shingle-style contemporary homes feature open-designed living spaces with vaulted ceilings, an abundance of glass and expansive decks to maximize indoor and outdoor living. Surrounded by a natural landscape of shady mature oaks, pines and maples, and a lush lawn that leads to the water's edge, this property faces west across the Edgartown Great Pond, providing afternoons basked in warm golden light th
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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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$2,850,000 8.3 acres
9 Boldwater Road, Edgartown, MA 02539 - Dukes County

8.3 acres Edgartown, MA

Wonderful waterfront site located on the Edgartown Great Pond in the Boldwater community. Enjoy boating, shellfishing and swimming from your doorstep. Owner has had an approval for a 10,000 sq' house with swimming pool as an indication of what can be permitted on this site. Boldwater amenities include boat landing, tennis, and association beach on the south shore.
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$2,050,000 3 acres 3 Beds | 2 Baths | 1536 sqft
43 Caleb Pond Road, Edgartown, MA 02539 - Dukes County

3 acres Edgartown, MA

Property Type:Single Family Total Rooms:6 Total Bedrooms:3 Total Bathrooms:2 Water Frontage:Pondfront Water Views:Pond Second Dwelling:None Zoning:R120 Lot Size:3.00 acres Total Sq. Feet (ELA):1,536 sq. feet Year Built:1983 Water / Sewer:Well / Septic -1 Assessment:$ 2,418,000 Land Assessment:$ 2,146,000 Build Assessment:$ 272,000 Estimated Taxes:$ 8,753 A serene pond front setting... Contemporary in design, casual in style with an open living area on the south side of the house with windows, sliders and deck offering pond views. Two generous guest rooms share a jack and jill bath on the first floor. The second floor has an open landing suitable for a small sitting area and a master bedroom with windows to the water, a cathedral cei
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$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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$1,995,000 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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$1,950,000 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! A share in Caleb's Beach, located 5 minutes walking distance away, is also available to the buyer.
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$1,325,000 2 acres
8 Milikin Way, Edgartown, MA 02539 - Dukes County

2 acres Edgartown, MA

KATAMA - 2 acre parcel that can support 8 bedrooms. Create your dream house with guest house and pool if you so desire. Height restriction is 32' therefore a second story waterview is likely depending on where you site your house. Plenty of options makes this unique piece of land very attractive to both the end user or speculative builder. This parcel is surrounded by multimillion-dollar properties and across the road from the Field Club.
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$1,325,000 3.45 acres 3 Beds | 3 Baths | 1900 sqft
289 The, Edgartown, MA 02539 - Dukes County

3.45 acres Edgartown, MA

Edgartown Custom brand new water view contemporary residence abutting the shores of Sengekontacket Pond and acres of wooded salt marsh. Features bright open living/dining/kitchen area with granite counters, custom cabinetry, stainless steel Bosch appliances, gleaming hard pine flooring, gas fireplace, lots of glass, first floor master suite, wonderful mahogany frame screen porch, sliders to sweeping rear deck, 2 more bedrooms on the second floor with another full bathroom with marble and white tile, and large family room/loft area. Excellent privacy! VIEWS galore over the POND and BARRIER BEACH out to Nantucket Sound. Super value!
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$1,295,000 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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$1,250,000 1.54 acres
3 Beach Plum Meadows, Edgartown, MA 02539 - Dukes County

1.54 acres Edgartown, MA

The last vacant parcel in tranquil Beach Plum Meadows, an upscale residential neighborhood of luxury homes. The building site will nicely accommodate a 4 bedroom home, pool and accessory structure and is buffered from the road with 150 feet of Katama flora. Just off the bike path to South beach, which is less than a mile away and only minutes to the Village. A terrific opportunity to create your dream home in a most desired area.
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$1,190,000 3.76 acres
8-10 Blue Heron Way, Edgartown, MA 02539 - Dukes County

3.76 acres Edgartown, MA

Blue Heron Way ~ A distinctive offering only a short walk from State Beach and within close proximity to Edgartown Village. This 3.76 acre parcel, encompassed by conservation, is the ideal building site for your Vineyard home. Convenient and private, the possibilities are endless... Three parcels being sold as one.
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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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$795,000 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.
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$379,000 3.4 acres
9 Ambers Way, Edgartown, MA 02539 - Dukes County

3.4 acres Edgartown, MA

On a small dead end lane, abutting conservation walking trails with unusually tall, mature trees and just off the paved road! Located about equi-distant to East Beach and the ferry. This is a lovely parcel of land and a very nice opportunity.