Chatham Luxury Homes $1M+

Dreaming of cool summer breezes and sunshine? Discover luxury homes in Chatham, a picturesque beachside town on Cape Cod, MA. Whether for a summer getaway or a permanent home, you are sure to find what you've been looking for. Save your favorites when you register with us today, and get notifications when similar properties are posted. Contact us for more information and to set up a showing for any listing below.

97 Tilipi, Chatham, MA 02633

Price$19,995,000

Est. Mortgage: $/month

MLS Number 21306159

  • Single Family
  • Acreage 1.9
  • Village Chatham
  • Lot Size Square Feet 82764
  • Bedrooms 6

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. idyllic property is incomparable on Cape Cod.

Listed by Pine Acres Realty

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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150 -154 Cross, Chatham, MA 02633

Price$11,700,000

Est. Mortgage: $/month

MLS Number 21801182

  • Single Family
  • Acreage 1.3
  • Village Chatham
  • Lot Size Square Feet 56628
  • Bedrooms 10

A Landmark in town Estate sited on 1.3 acres of rolling lawns and elevated westerly water views over the Oyster Pond is available for the first time in over a generation. The Beechwood is a stately Federal style home built by Henry Sherman Howes in 1948, using the finest materials and craftsmanship. Unique ability to use as an 8000 s.f.single family, or have three legal townhomes, each with separate entrances. 10 BR's, 7 full and 3 half baths,7 fireplaces, three story elevator, an additional 4000 s.f. on lower level with speakeasy and ballroom. Incredible hand painted murals, curved staircase, and hand carved woodwork are just some special details. The grounds include multiple terraces,specimen plants and terrific privacy. A living piece of history. Peerless in its architechual detail and scale. Steps to both a sandy beach and the vibrant village of Chatham. Please ask broker for full historic information.

Listed by Pine Acres Realty

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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75 Tilipi Run, Chatham, MA 02633

Price$9,900,000

Est. Mortgage: $/month

MLS Number 21607303

  • Single Family
  • Acreage 1.45
  • Village Chatham
  • Lot Size Square Feet 63162
  • Bedrooms 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. gardens, this is one of Chatham's finest properties.

Listed by Pine Acres Realty

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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74 Sears Point, Chatham, MA 02633

Price$6,750,000

Est. Mortgage: $/month

MLS Number 21407880

  • Single Family
  • Acreage 6.63
  • Village Chatham
  • Street Number Modifier 77
  • Lot Size Square Feet 288803

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 built in 1959 spanning 2,500 s.f. sited 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

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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113 Seapine, Chatham, MA 02633

Price$5,695,000

Est. Mortgage: $/month

MLS Number 21714366

  • Single Family
  • Acreage 0.62
  • Village Chatham
  • Lot Size Square Feet 26970
  • Bedrooms 4

Designed and built by Polhemus Savery DaSilva, this impeccable waterfront property offers stunning views of Crows Pond. The shingle style residence features four bedrooms and five and a half baths with direct steps down to the beach. With abundant natural light and views from nearly every room, the open floor plan integrates modern design with a signature beach-style vernacular. The main entry opens to a vista filled great room with fireplace, dining area leading to a waterside patio and infinity edge pool and a grand chef's kitchen with adjoining screened porch. There is a first floor master suite, mudroom, laundry, pantry and powder room. Above is a master suite and two additional en-suite bedrooms. The home is complete with a spectacular lower level and exercise room.

Listed by Pine Acres Realty

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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72 Main, Chatham, MA 02633

Price$5,000,000

Est. Mortgage: $/month

MLS Number 21717503

  • Single Family
  • Acreage 1.17
  • Village Chatham
  • Lot Size Square Feet 50965
  • Bedrooms 5

LIGHTHOUSE BEACH is your front yard Overlooking the Atlantic Ocean and Chatham Harbor with the best white sand beach one could imagine. This incredible FIVE bedroom, 4 1/2 bath home built by Polhemus, Savery and DeSilva is truly spectacular. This most sought after Chatham location is a short walk to town and the private beachfront of this caliber is not only rare but impossible to find. First floor master bedroom, a chef's kitchen, fabulous dining room, a livingroom with fireplace and a covered porch for your rocking chairs for you to soak in the view from. There are 4 more bedrooms upstairs and the finished lower level is truly incredibly finished to make you feel as though your are on a yacht. Please review the pictures and you will agree ! There are stone patios and outdoor fireplace...

Listed by Chatham Real Estate, LLC

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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24 Captain Sears, Chatham, MA 02633

Price$4,999,999

Est. Mortgage: $/month

MLS Number 21802665

  • Single Family
  • Acreage 0.96
  • Village Chatham
  • Lot Size Square Feet 41818
  • Bedrooms 5

Flawlessly renovated Waterfront estate on sheltered inlet with dock boasts 5BR's, 5.5 baths and is sited on a very private lot.A complete and thoughtful renovation in 2003 incorporated the needs of today with a preservation of the unique details of the past. Inviting kitchen with walls of windows overlooking the water also includes Viking and Wolf appliances, copper farmer's sink and breakfast room. The Great room beckons with soaring ceilings, stone fireplace, and multiple french doors leading to patio. A screened in porch with fireplace, solid cherry paneled study and grand gallery are just some additional spaces. A master suite offers his/ her closets, and privacy from additional bedrooms. Surrounded by flowering coastal gardens, Pickle ball court and boating access to Nantucket Sound.

Listed by Pine Acres Realty

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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155 & 157 Bridge, Chatham, MA 02633

Price$4,995,000

Est. Mortgage: $/month

MLS Number 21803466

  • Single Family
  • Acreage 2.83
  • Village Chatham
  • Lot Size Square Feet 123275
  • Bedrooms 8

This remarkable waterfront location overlooks the Mitchell River and Mill Pond and presents a multitude of possibilities for development or renovation. Privately situated within mature landscaping on 2.8 acres with 900 feet of waterfront footage, this current family compound comprises a five bedroom, four and a half bath main house with an inground swimming pool. On a separate parcel resides a three bedroom, two and a half bath, spacious guest house with a tennis court. This is a perfect venue to create a family retreat for generations to come, yet there is also the possibility to subdivide the two lots and develop two brand new waterfront homes in one of Chatham's most picturesque settings.

Listed by Pine Acres Realty

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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114 Cranberry, Chatham, MA 02650

Price$4,995,000

Est. Mortgage: $/month

MLS Number 21802938

  • Single Family
  • Acreage 1.42
  • Village North Chatham
  • Lot Size Square Feet 61760
  • Bedrooms 5

''Cranberry Manor'' is the epitome of luxury living on Cape Cod. This exquisite estate is privately situated down a winding lane in North Chatham. From the minute you enter the dramatic front foyer you will be impressed by the quality and attention to detail thru out. From the furniture quality trim, doors and windows to the 8''white oak flooring with natural finish thru out. Open kitchen with Fantasy Brown marble counter tops and Wolf, Subzero and Asko appliances. In addition there is a home theater, game room and gym in the lower level which opens up to the custom expansive pool area including outdoor kitchen, hot tub, outdoor theater and path to a sandy beach on Pleasant Bay. Adjacent to the home and pool is a guest home of similar quality for overflow or guests. Central a/c and gas hea of course and a 400 amp electrical service. There is also a 22kw Generac back up power system if ever needed. Under "other documents" is an extensive specification sheet for the property. Over 1.4 acres for professionally landscaped property with irrigation and stunning stone walls. The pool is surrounded by wrought iron fencing.

Listed by William Raveis RE & Home Serv.

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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369 Old Harbor, Chatham, MA 02633

Price$4,950,000

Est. Mortgage: $/month

MLS Number 21803306

  • Single Family
  • Acreage 1.77
  • Village Chatham
  • Lot Size Square Feet 77101
  • Bedrooms 18

The ultimate Chatham, Cape Cod experience. This private 1.77 acre compound with multiple historic buildings and lovely manicured grounds and pool could be your family retreat. Includes a modern home adjacent to 369 Old Harbor, located at 36 Manamock Rd. A short stroll to Chatham's Main Street famous for shops, galleries and fine and fun dining. Near sandy ocean beaches, golf, theater, island ferries and everything wonderful to do on the Cape. Your family and guests will enjoy luxury accommodations. Elegant sunny dining room is the perfect sunny spot to entertain. The experience here is all about this amazing location and all that Cape Cod offers. Ample off street parking, furnished. Currently licensed and operating as a B&B Inn. Many possibilities. Business Financials available.

Listed by Cape Cod Village Realty

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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141 Cotchpinicut, Chatham, MA 02633

Price$4,900,000

Est. Mortgage: $/month

MLS Number 21713971

  • Single Family
  • Acreage 1.03
  • Village Chatham
  • Lot Size Square Feet 44867
  • Bedrooms 8

This multi generational landmark, legacy compound is perfectly situated on one of Chatham's most sought after streets. Main house with gorgeous raised wood paneling, over sized kitchen and great room opens to lush gardens and in ground pool area perfect for entertaining family and friends. The master suite features stunning ocean views and private oversized deck. Guest house offers a spacious billiards/game room and loft area and two bedrooms. There is also an additional separate one bedroom apartment attached. This is a once in a lifetime offering at the end of a very special street. The estate is steps to a private sandy neighborhood beach. Watch the video tour to get a better perspective!

Listed by Robert Paul Properties, Inc.

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Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

338 Seapine, Chatham, MA 02650

Price$4,750,000

Est. Mortgage: $/month

MLS Number 21509408

  • Single Family
  • Acreage 1.56
  • Village North Chatham
  • Lot Size Square Feet 68044
  • Bedrooms 4

Paradise Found! Relax and drink in the glorious salt air and sea breezes. Put your toes in the warn soft sandy beach outside your door. This is authentic Cape Cod at it's finest. This is not a glitzy new home by any means but if you are truly looking for a special place to begin your coastal memories- look no further. This is a once in a lifetime legacy property with the most remarkable views anywhere! After a day at the beach or after a round of golf settle back, relax and take in one of the prettiest views on the Cape. On a quiet cul-de-sac, at the very end of the road and sitting on just over an acre of land, this home is a classic Cape with old world charm and views from every room. New isn't always better, this house is drenched in charm & comfort.please watch video

Listed by Robert Paul Properties, Inc.

{$agent->Name}

Brewster Office
15 Cape Lane
Brewster MA, 02631
Office: 508-776-4664

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.15% last updated on Jan 25, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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broker reciprocity 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 Cape Cod Chatelains are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Cape Cod Chatelains shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated May 22, 2018. All properties are subject to prior sale, changes, or withdrawal.

Cape Cod Chatelains has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.