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Chatham MA Real Estate

Browse through Chatham, Cape Cod real estate listings below to find your next property! Situated on the "elbow" of the Cape, you'll be sure to find quintessential Cape Cod real estate in Chatham, including single family homes, condos, commercial properties, land, and multifamily homes. Buy a property right on Main Street, with a view of the famous Chatham Lighthouse, or right on the beach!

Let us know if you would like to learn more about any of the listings below or set up a tour.  You can also sign up with our site to save all of your favorite Chatham properties and be notified when new listings match your search criteria.  

You may also like to browse homes in Orleans MA or homes in Barnstable MA.

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97 Tilipi Chatham MA 02633

Village: Chatham
Town: Chatham MA 97 Tilipi Run

Price: $25,000,000

Est. Mortgage: $/month

MLS Number 21306159

  • Single Family
  • Acreage 1.90
  • Village Chatham
  • Bedrooms 6
  • Bathroom 10

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.

Listed by Pine Acres Realty

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

157 Wapoos Trail Chatham MA 02633

Village: Chatham
Town: Chatham MA 157 Wapoos Trail

Price: $18,000,000

Est. Mortgage: $/month

MLS Number 21305971

  • Single Family
  • Acreage 13.80
  • Village Chatham
  • Bedrooms 5
  • Bathroom 8

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

Listed by John C Ricotta & Assoc.

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

96 Tilipi Run Chatham MA 02633

Village: Chatham
Town: Chatham MA 96 Tilipi Run

Price: $8,795,000

Est. Mortgage: $/month

MLS Number 21200173

  • Single Family
  • Acreage 1.88
  • Village Chatham
  • Bedrooms 6
  • Bathroom 9

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.

Listed by Pine Acres Realty

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

75 Tilipi Run Chatham MA 02633

Village: Chatham
Town: Chatham MA 75 Tilipi Run

Price: $7,995,000

Est. Mortgage: $/month

MLS Number 21309377

  • Single Family
  • Acreage 1.45
  • Village Chatham
  • Bedrooms 6
  • Bathroom 6

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.

Listed by Pine Acres Realty

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

74 Sears Point Chatham MA 02633

Village: Chatham
Town: Chatham MA 74 Sears Point Rd

Price: $7,500,000

Est. Mortgage: $/month

MLS Number 21407880

  • Single Family
  • Acreage 6.63
  • Village Chatham
  • Bedrooms 5
  • Bathroom 4

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.

Listed by Pine Acres Realty

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Whidah Road Chatham MA 02650

Village: Chatham
Town: Chatham MA Whidah Road

Price: $6,000,000

Est. Mortgage: $/month

MLS Number 21407854

  • Lots and Land
  • Village Chatham

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.

Listed by LandVest, Inc.

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

80 Quasson Chatham MA 02633

Village: Chatham
Town: Chatham MA 80 Quasson Rd

Price: $4,999,000

Est. Mortgage: $/month

MLS Number 21408013

  • Single Family
  • Acreage 0.54
  • Village Chatham
  • Bedrooms 4
  • Bathroom 3

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.

Listed by Bohman Thayer Real Estate

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

180 Stage Island Chatham MA 02633

Village: Chatham
Town: Chatham MA 180 Stage Island Rd

Price: $4,500,000

Est. Mortgage: $/month

MLS Number 21406168

  • Single Family
  • Acreage 0.91
  • Village Chatham
  • Bedrooms 4
  • Bathroom 5

One of the most stunning waterfront settings with a dock in Chatham, this incredible Cape home is front and center on Stage Island overlooking Stage Harbor. Well known for it's ever changing landscape of sailing and motor yachts, Stage Harbor evokes the truest sense of being on Cape Cod. Lovely four bedroom, 4.5 bath home nestled on a knoll and surrounded by mature coastal gardens, it offers dramatic views and open floor plan. Filled with light and spacious windows opening to the outside. First or second floor master suites, comfortable guest accommodations and recently finished walk out lower level with room for office, game room and gym, all with ceramic tile floors. Two oversized decks perfect for outdoor entertaining. Enjoy boating from your backyard from your own private dock. Association offers sandy beach on Chatham Harbor.

Listed by Pine Acres Realty

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

53 Grist Mill Chatham MA 02633

Village: Chatham
Town: Chatham MA 53 Grist Mill Ln

Price: $4,350,000

Est. Mortgage: $/month

MLS Number 21401049

  • Single Family
  • Acreage 0.96
  • Village Chatham
  • Bedrooms 5
  • Bathroom 7

A stunning waterfront estate within steps to the center of the village. Spectacular views of the Mill Pond and stairs leading to the water and onto a catwalk providing access to the waters edge. Open floor plan, cathedral living room, charming sunroom, brick terrace with outdoor cooking and wet bar and hot tub. Mill Pond is Chatham's finest protected water allowing deep water access to Stage Harbor and Nantucket Sound.

Listed by William Raveis RE & Home Serv.

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

720 Orleans Chatham MA 02633

Village: North Chatham
Town: Chatham MA 720 Orleans Rd

Price: $3,500,000

Est. Mortgage: $/month

MLS Number 21408409

  • Single Family
  • Acreage 1.18
  • Village North Chatham
  • Bedrooms 4
  • Bathroom 6

This extraordinary setting on Ryder's Cove offers spectacular views, privacy and the opportunity for a completely renovated Eastward Companies home in North Chatham. Sited on aprox. 1.18 acres, this property is comprised of a newly located historic Captain's home that offers fabulous additions and modern amenities. Spanning 3, 400 s.f., it feautures a four bedroom main house with a bonus room, two car garage and a one bedroom guest house. This is a very unique waterfront opportunity in North Chatham, steps from the marina, and a short drive to town.

Listed by Pine Acres Realty

Martha Murray Real Estate
63 Lower County Road
Dennisport MA, 02639
Office: 508.394.2115

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.12% last updated on 2014-09-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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