Homes in Chatham

49 New/Updated Properties in Chatham
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97 Tilipi Run 1
97 Tilipi Run 297 Tilipi Run 397 Tilipi Run 497 Tilipi Run 5
$25,000,000
6 Bedrooms / 
8.00 Bathrooms
10,974 SqFt / 1.90 Acres
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Boasting one of the most spectacular properties on the Cape Cod shoreline, this shingle-clad home is poised on 1.9 acres and majestically resides over the Atlantic Ocean, Monomoy Islands and Nantucket Sound. With 10,974 square feet of living space spanning three levels, the six bedroom estate has simply breathtaking views, manicured grounds and a glorious stone pool pavilion. The enchanting home is designed with a circular motif and gleams of pure elegance and includes multiple family gathering rooms, a banquet size dining room, chef's kitchen, 11 seat theater, an opulent wine cave and a circular one bedroom carriage house for guests or staff. A Creston smart home system controls security, electronic gate, lighting, audio, and driveway and pool heat with a touch of a button. This idyllic property is incomparable on Cape Cod.
157 Wapoos Trail 1
157 Wapoos Trail 2157 Wapoos Trail 3157 Wapoos Trail 4157 Wapoos Trail 5
$18,000,000
5 Bedrooms / 
7.50 Bathrooms
7,500 SqFt / 13.80 Acres
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Iconic 13+ acre waterfront estate on Morris Island complete w/ a 5 bedroom 7 1/2 bath main house & a 40 X 30 foot boathouse w/ permanent dock & two side floats. Other structures on the sprawling property include a chapel, children's retreat,& garden shed. The Main house includes a two-story entry hall with circular staircase, living room,formal dining room,library,family room,sunroom,gourmet kitchen,screened porch,5 bedrooms,3 w/ private en suite bath,& all w/ spectacular water views.Additional features include a third floor craft room,a fireplaced billiard room on the lower level,& so much more!There are 6 other fireplaces in the main house & a wood stove in the boathouse. A golf cart to navigate from one breathtaking vista to another.The manicured gardens & long winding drive complete this incredible property.CLICK ON VIRTUAL MEDIA TOUR
96 Tilipi Run 1
96 Tilipi Run 296 Tilipi Run 396 Tilipi Run 496 Tilipi Run 5
$8,795,000
6 Bedrooms / 
8.00 Bathrooms
9,700 SqFt / 1.88 Acres
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An impeccable Morris Island property, this grand shingle-style home offers unparalleled views of the Atlantic and Monomoy islands. Offering architectural sophistication and elegant craftsmanship, this six bedroom, eight baths home spans almost 10,000 S.F. over three levels. Completed in 2009, the main entrance features a foyer leading to the main living space and adjoining hallway with elevator. The main level includes an elegant en suite master bedroom, living room, dining room and luxury chef's kitchen, all with panoramic views. The expansive second level offers five additional en suite bedrooms, multiple balconies and sweeping views throughout. The lower level boasts a plethora of stunning living spaces that completes this superlative property. Meticulous attention to detail is shown in every aspect of this home's exceptional design.
75 Tilipi Run 1
75 Tilipi Run 275 Tilipi Run 375 Tilipi Run 475 Tilipi Run 5
$7,995,000
6 Bedrooms / 
5.00 Bathrooms
6,043 SqFt / 1.45 Acres
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Situated in one of Chatham's most prestigious neighborhoods, this luxurious Morris Island residence is truly unique among waterfront properties. Perched high above the shoreline, with panoramic views of the Atlantic Ocean and Monomoy Islands, this world class home offers a magnificent living experience. Commanding views from nearly every room, this six bedroom, four full and two half bath home has excellent flow and generously proportioned rooms. The finest artisan fixtures and custom craftsmanship are seen throughout. Highlights include a magnificent great room with stone and wood architectural touches, a gourmand's kitchen, a magnificent first floor master suite, billiard room, & a lower level filled with every amenity imaginable. Beautifully landscaped with lawns and lovely gardens, this is one of Chatham's finest properties.
74 77 Sears Point Rd 1
74 77 Sears Point Rd 274 77 Sears Point Rd 374 77 Sears Point Rd 474 77 Sears Point Rd 5
$7,500,000
5 Bedrooms / 
3.50 Bathrooms
2,597 SqFt / 6.63 Acres
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This exceptional waterfront property offers arresting panoramas of Stage Harbor and beyond. Situated in one of Chatham's most private enclaves, the property is comprised of two adjoining lots totaling 6.6 acres and 350 feet of water frontage. A long winding driveway and charming barn enhance the property's magical approach. Currently there is an existing five bedroom, three and half bath classic Cape Cod style residence spanning 2,500 s.f. and built in 1959 set back and elevated on the property. This unbeatable setting offers exceptional potential to built a dramatic dream estate or to reinvent the old. Existing Polhemus Savery DaSilva architectural plans are available. Discover more about this spectacular property upon request.
0 Whidah Road 1
$6,000,000
6.33 Acres
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This Pleasant Bay waterfront property presents a unique opportunity to create a family compound that will be a summer gathering place for future generations. Currently the largest undeveloped waterfront listing in Chatham, the property consists of 6.3+/- acres configured into 2 lots with a 50% undivided interest in the sandy beachfront lot on Bassing Harbor. Conceptual plans for 2, 3, and 4 lot subdivisions are available. Chatham is located at the elbow of Cape Cod, half way between Falmouth and Provincetown and is about 90 miles from Boston and Providence. Highly regarded as one of the top summer communities on Cape Cod, it is close to Nauset beach, a famous surfing venue, and world-class saltwater fishing. There are 12 public and private golf courses within 10 miles of Chatham center as well as many fine shops and restaurants.
80 Quasson Rd 1
80 Quasson Rd 280 Quasson Rd 380 Quasson Rd 480 Quasson Rd 5
$4,999,000
4 Bedrooms / 
2.50 Bathrooms
2,419 SqFt / 0.54 Acres
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Stunning unobstructed panoramic Pleasant Bay, Outer Beach and Atlantic Ocean front row views located in the heart of Chatham. This property offers a unique opportunity to find a waterfront estate outside of the new flood zone and build the home of your dreams. Architectural plans with one of our area's most respected design firms are in the works for a five bedroom 5,000 square foot house. The seller is willing to work with the buyer through the permitting process.

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Kinlin Grover Real Estate are marked with the BR logo. This site was last updated Sep 02, 2014.
All properties are subject to prior sale, changes, or withdrawal.
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