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Dukes County, Massachusetts: Land, Ranches, Farms & more

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$22,500,000 29.3 acres 7 Beds | 8 Baths | 6892 sqft
79 Turkeyland Cove Road, Edgartown, MA - 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 - 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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$19,125,000 9.5 acres 6 Beds | 7 Baths | 6967 sqft
8 Snail Road, Chilmark, MA - Dukes County

9.5 acres Chilmark, MA

Majestically perched 120 feet above the Atlantic Ocean, the magnificent Chilmark House is an award-winning triumph of design and execution. A presidential paradise, this estate served as the 2013 summer White House. A comfortable yet luxurious seaside retreat that celebrates panoramic ocean views of Martha's Vineyard South Shore and Chilmark Pond. This home features gracious skylights, huge windows, soaring ceilings and wonderful detail in both design and materials. Heated infinity pool, half-basketball court, large screened porch and outdoor terraces provide a breezy and beautiful venue for all. This secluded residence and 2 bedroom guest cottage sit on 9.5 acres of wooded hillside and includes three private Atlantic Ocean beach lots acces
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$10,500,000 3.5 acres 3 Beds | 3 Baths | 2488 sqft
22 Quitsa Lane, Chilmark, MA - Dukes County

3.5 acres Chilmark, MA

Cliff Cottage enjoys one of the most picturesque settings and water-views on Martha's Vineyard. Originally built in 1850 and painstakingly remodeled by the current owner's, along with one of the Islands finest builders to reflect today's life style and amenities. The recently constructed detached studio with over 1,400 sq' offers 2 additional bedrooms with water-views along with an office and a garage. An association stairway leads to your private sandy beach on the south shore, additionally, there is deeded access to Menemsha Pond a short walk away.
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$6,999,000 22 acres 11 Beds | 8 Baths | 5666 sqft
556 Chappaquonsett Road, North Tisbury, MA - Dukes County

22 acres North Tisbury, MA

This private waterfront compound set on a 22-acre parcel is located in exclusive Northern Pines, off Lambert's Cove Rd. Deserving of superlatives in every category, the property includes three structures nestled on the shore - main house, 1586 sf guesthouse, and romantic 600 sf Pond House. All have stunning, panoramic water views. The main house has classic Vineyard character with its Cape Cod style, shingle exterior, bright interior, and blue exterior shutters. It surprises by opening to more contemporary facades that face the water with lots of glass. Spacious and comfortable, with five bedrooms and seven baths. The guesthouse is a renovated carriage house that includes four bedrooms, a beachy dcor, and a farmer's porch with wood decking
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$6,500,000 3 acres 4 Beds | 5 Baths | 5310 sqft
44 Caleb Pond Road, Edgartown, MA - 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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$5,700,000 6.7 acres 5 Beds | 4 Baths | 3009 sqft
275 South Farm Road, North Tisbury, MA - Dukes County

6.7 acres North Tisbury, MA

This unique waterfront estate on the shores of Lake Tashmoo offers open ocean access with a deep water dock. The 12 room house along with 3 other structures are situated on a peninsula on 6.4 acres. The property offers the ultimate in waterfront privacy with 700' of frontage and a gentle sloping sandy beach ideal for little ones. There is a plentiful supply of shellfish along with a family of otters & a pair of ospreys near the shore with an occasional sighting of harbor seals. Inside offers 12 rooms with an open flowing feel including a spacious gourmet kitchen with updated appliances, walk in pantry, wood floors, skylights, cathedral ceilings , screened waterside porch, living room, den and a private 2nd floor master suite with a wraparou
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$5,450,000 3.4 acres 4 Beds | 3 Baths | 3298 sqft
82 Turkeyland Cove Road, Edgartown, MA - 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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$4,950,000 8 acres 5 Beds | 3 Baths | 2511 sqft
1 Azalea Lane, Chilmark, MA - Dukes County

8 acres Chilmark, MA

Experience extraordinary waterfront living on one of the finest private beaches along Chilmark's south shore. Mesmerizing water views can be enjoyed from almost every room including the living and dining areas, master bedroom, guest bedrooms, and more. The south facing deck & pool area were designed to capture the essence of the ocean while maintaining absolute privacy. Meticulously landscaped from the driveway entrance to the cliff's edge walking path. An association tennis court is shared with 3 other properties.
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$3,950,000 6.42 acres 3 Beds | 2 Baths | 1300 sqft
60 Bartimus Luce Road, West Tisbury, MA - Dukes County

6.42 acres West Tisbury, MA

Simply stunning ~ Only lush lawn and sand exist between the ocean and your door. Truly a place to unwind, relax and revel at the endless views of the Vineyard Sound and the Elizabethan Islands. A winding drive from Lambert's Cove Road leads through oaks, cedars and beautiful stone walls to an oasis at the end of the road. Emerge from the canopy to an expansive and manicured lawn which leads to the bluff and artfully crafted stairs that descend to nearly 250' of sandy beach and sparkling ocean. The existing home sits overlooking the water and comfortably accommodates but expansion options abound.
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$3,900,000 4.8 acres 4 Beds | 3 Baths | 1788 sqft
9 Briggs Road, Edgartown, MA - 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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$3,250,000 3 acres 6 Beds | 3 Baths | 2385 sqft
8 Caleb Pond Lane, Edgartown, MA - Dukes County

3 acres Edgartown, MA

Prominently situated atop Manaca Hill, lies this 6-bedroom home on 3 acres of land with spectacular unobstructed views of the entrance to Edgartown Harbor. The 180-degree panoramic views stretch from North Water Street and sweep through Edgartown Lighthouse and across to the Cape Pogue cliffs. The original home built in 1910 is in good condition and a new 6-bedroom septic system was installed. A long private driveway winds through beautiful fields and the property includes ownership of a beach parcel within 100 yards of the front door and a mooring. A must see for anyone considering a very special Chappaquiddick offering.
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$3,195,000 11.93 acres 5 Beds | 5 Baths | 4300 sqft
8 Boldwater Road, Edgartown, MA - 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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$2,990,000 0.79 acres
15 Island Inn Road, Oak Bluffs, MA - Dukes County

0.79 acres Oak Bluffs, MA

Highly successful LOLA's Restaurant and function center located off Beach Road in Oak Bluffs is now for sale. Established business in ideal setting with parking, separate function rooms, bars, patios, separate catering kitchen and room for expansion. It is located right off the water and next to prestigious Farm Neck golf course. This easily accessible and successful establishment has $750,000 on their calender from year to year for events and such, and current management/owners will stay on if needed! Operated currently as a restaurant, night club, wedding and event destination. Thats over 5,800 square feet on main level, there is a functional Basement, and the 2nd level has ocean views.Certificate of Occupancy has seating for 285, and is
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$2,850,000 8.3 acres
9 Boldwater Road, Edgartown, MA - 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.