Chatham Homes with a Pool

Browse current homes with pools for sale in Chatham, MA. Search through hundreds of listings in this oceanside Cape Cod town. Found something you love? Save it when you register with us, and you can get email notifications when new properties match your criteria. If you already have an account, sign in here.

Contact us today for more information, questions, and to schedule a showing!

To view all homes for sale in Chatham - click here.

203 Cross Chatham MA 02633

Chatham, MA203 Cross Street

Price$2,495,000

Est. Mortgage: $/month

Open House

MLS Number 22000232

  • Single Family
  • Next Open House: Sun 26th 10:00 am - 12:00 pm
  • Village Chatham
  • Year Built 1928
  • Bathroom 4

Iconic Chatham home in a premier location close to town and Oyster Pond. Beautifully appointed with exceptional attention to detail and craftsmanship throughout. Spanning over 3,000 s.f. with 4 generous bedrooms including two master suites, gourmet kitchen, well-appointed living room, dining room, screened in porch, home office, family room, second floor sitting area, and roof deck where sunsets and fireworks can be enjoyed. The grounds feature artistic stone work including a beautiful blue stone patio, artistic walkways, fire pit, and thoughtful plantings. This special offering is set back from the road and has room for a pool. This light filled pleasant home is meticulously maintained and well cared for.

Listed by Doug Grattan of Chatham Properties Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

485 Shore Chatham MA 02633

Chatham, MA485 Shore Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 22000076

  • Single Family
  • Village Chatham
  • Year Built 1986
  • Bathroom 6
  • Full Bathrooms 5

The very best value on Shore Road and in Chatham. Picture yourself waking up in this sun drenched home on the most sought after location in all of Chatham. This home has been tastefully updated to create a soft, coastal look and feel with stylish appointments throughout. The generous size bedrooms and floor plan is perfect for multi generational families to enjoy entertaining, walks to the beach and town and still offer plenty of space for privacy. The open and airy living space allows for great indoor and outdoor entertainment, there is even room for a pool. Recent updates include a new architectural Shingle 30 year roof, new gutters, new 1st floor Anderson Window Sliders, all new Kitchen Aid appliances, custom tile kitchen backsplash, new Quartz countertops, entire interior painted, new lighting and refinished White Ash hardwood floors. Close to Chatham Bars Inn which now offers a beach and social club membership. There are also deeded rights to Chatham Harbor.

Listed by Team Guthrie - Mabile of Robert Paul Properties, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

55 Independence Chatham MA 02633

Chatham, MA55 Independence Lane

Price$1,895,000

Est. Mortgage: $/month

MLS Number 22000135

  • Single Family
  • Village Chatham
  • Year Built 1983
  • Bathroom 3
  • Full Bathrooms 3

Located in a prime location, this renovated home offers both privacy and walking distance to Chatham Village and Oyster Pond Beach. Nestled along the loop, the layout covers approximately 3,400 square feet of separate living spaces. Ideal for entertaining, the first floor comprises a custom kitchen with center island, a large dining room, cathedral ceiling living room with stone wood burning fireplace and sliding French doors to a brick patio and a spacious outdoor oasis with beautiful plantings. There is a first-floor bedroom, full bath, a newly designed den and a spacious mudroom. The main stairway leads to a light filled master suite and the back stairway leads two bedrooms with a shared bath. Highlights include gleaming wide pine floors, a two-car garage, and potential for a pool.

Listed by Chris Rhinesmith of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

41 Mooncussers Chatham MA 02633

Chatham, MA41 Mooncussers Lane

Price$1,499,000

Est. Mortgage: $/month

MLS Number 22000138

  • Single Family
  • Village Chatham
  • Year Built 2000
  • Bathroom 5
  • Full Bathrooms 4

SEARS POINT: Surrounded by beautiful homes in an , this impressive, well-maintained residence offers an open layout over 3 floors. The double-height entrance hall opens to an office and 1/2 bath and welcomes you to both the main and lower level. Below is a large family room with fireplace, two en-suite bedrooms and laundry, with sliding doors to a patio. Above, the main level has soaring ceilings, large living room with fireplace, master with Jacuzzi tub, kitchen with open dining room and bar area. Expansive windows bring the light in and sliding doors open to a brand new full-length deck. Above the two-car garage is the lofty, private fourth en-suite bedroom with a large whirlpool tub. The home has extensive amenities and lovely outdoor living space making this a perfect home

Listed by Chris Rhinesmith of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

16 Aunt Lydias Chatham MA 02633

Chatham, MA16 Aunt Lydias Way

Price$3,495,000

Est. Mortgage: $/month

MLS Number 22000129

  • Single Family
  • Village Chatham
  • Year Built 2005
  • Bathroom 6
  • Full Bathrooms 3

This beautiful resort-style residence offers the perfect balance of privacy, tranquility and location. Set on a quiet cul-de-sac just off Shore Rd, the home has deeded access to Aunt Lydia's Cove and is a short walk to the Fish Pier and Chatham Bars Inn. The home is introduced by a grand foyer with soaring ceilings, while the generously proportioned first floor rooms are complete with elegant living and dining rooms, a master suite, a stylish eat-in kitchen and a spacious family room. Above are three bedrooms, a wood paneled clubroom and a third-floor loft currently used as a children's paradise. The meticulously landscaped grounds with stone patio and mature hedging provide a spa-like setting and ideal location for a pool. This showcase residence is Chatham living at its finest.

Listed by Chris Rhinesmith of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

155 & 157 Bridge Chatham MA 02633

Chatham, MA155 & 157 Bridge Street

Price$4,595,000

Est. Mortgage: $/month

MLS Number 22000128

  • Single Family
  • Village Chatham
  • Year Built 1980
  • Bathroom 9
  • Full Bathrooms 7

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 Chris Rhinesmith of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

373 Bridge Chatham MA 02633

Chatham, MA373 Bridge Street

Price$6,995,000

Est. Mortgage: $/month

MLS Number 22000133

  • Single Family
  • Village Chatham
  • Year Built 2019
  • Bathroom 9
  • Full Bathrooms 8

Boasting one of Chatham's most sought-after Light House Beach locations, this stunning estate set on 1.54 acres is a true family compound. The brand new 5 BR main house is masterfully designed with a relaxed open layout combining elegance and sophistication. The first floor has a central kitchen, dining room, multiple living spaces with an en-suite bedroom. The upper floor offers a sumptuous master bedroom-suite with a family room and three additional en-suite bedrooms. The lower level has an entertainment room, family room, wine storage and full bath. The guest house built in 2003 offers striking spaces, three fireplaces, a first and second floor master suite, and an indoor lap pool. The estate is enhanced with lushly landscaped grounds, a pool, and a detached garage. (Note: Furniture Photos in Listing sheet are a combo of virtually and past staging efforts)

Listed by Chris Rhinesmith of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

230 Cedar Chatham MA 02633

Chatham, MA230 Cedar Street

Price$10,500,000

Est. Mortgage: $/month

MLS Number 21908223

  • Single Family
  • Village Chatham
  • Year Built 1960
  • Bathroom 6
  • Full Bathrooms 5

This extraordinary waterfront estate is one of the most significant properties to come to market in Chatham. Set on 7.75 fenced in acres and abutting 20 acres of conservation, the residence offers 300 feet of waterfront footage, a deep-water dock, Pebble-Tec pool, fountain and an impeccable Oyster Pond River setting that is just a short stroll to Chatham's Village. The multi-roomed renovated estate comprises 5 BR 4.1BA with 3 fireplaces, custom kitchen with Aspen wood cabinetry, first floor master suite and views from nearly every room. The estate surprises with a whimsical two-story ''tower'' radiating light that connects to a dramatic lounge with soaring beamed ceilings, state of the art projection systems, billiard room, kitchen, and full bath. Full amenities available upon request.

Listed by Chris Rhinesmith of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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

324 Deer Meadow Chatham MA 02633

Chatham, MA324 Deer Meadow Lane

Price$985,000

Est. Mortgage: $/month

MLS Number 21908160

  • Single Family
  • Village Chatham
  • Year Built 1979
  • Bathroom 4
  • Full Bathrooms 3

Nestled in the heart of Riverbay, this gorgeous gem has it all and then some. Amenities galore, coupled with a pool, AND tennis court on over an acre, pristine landscaping (on a well), and bonus rooms throughout for family and friends to gather and enjoy. Walk-out lower level includes a second living room with fire place, perfect for indoor/outdoor entertaining, full updated bathroom, and additional room for office or guest overflow. Current owners updates include interior painting throughout, new flooring in the master bedroom and lower level, 2 completely renovated bathrooms, and new lighting. Perfect rental investment, family get-a-way retreat, or year round living - move in now and start enjoying right away!

Listed by Team Guthrie - Mabile of Robert Paul Properties, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

300 Stage Neck Chatham MA 02633

Chatham, MA300 Stage Neck Road

Price$14,900,000

Est. Mortgage: $/month

MLS Number 21908121

  • Single Family
  • Village Chatham
  • Year Built 2001
  • Bathroom 9
  • Full Bathrooms 5

Seaside sophistication in a world class setting!The lure of breathtaking water vistas and the appeal of luxurious appointments can be found in this grand waterfront property known as ''Viewpoint Estate.'' An unparalleled location, the secluded 5.2-acre setting offers panoramic water vistas of Oyster Pond River, Hardings Beach and Nantucket Sound. Set atop an elevated bluff surrounded by 1,130 feet of shoreline, the owners painstakingly created this spectacular estate where privacy was paramount, and design incorporated the ideal balance of comfort and elegance. The 10,350 sq. ft. main residence offers sophisticated, striking design, generous yet comfortable living spaces, beautiful architectural detailing, richly variegated water views and flawless craftsmanship. Interior spaces include a welcoming foyer, stunning great room and formal dining room along with a fabulous chef's kitchen with top of the line appliances and a large breakfast area, and a mahogany clad private bar and office. The upper level features five bedrooms including the stunning master suite and a bunkroom over the garage. The lower level offers a custom designed theater room with billiards area and sixth en suite bedroom. An infinity-edge pool, multiple outdoor seating areas and path to the water's edge are havens for entertaining or relaxing and soaking in the sweeping views. Also included is a beautifully designed 1,673 square foot guest house featuring two separate apartments ideal for extended family and friends. 'Viewpoint Estate' offering an unparalleled lifestyle is a legacy property for generations to come.

Listed by Robert B Kinlin of Robert Paul Properties, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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

113 Seapine Chatham MA 02650

Chatham, MA113 Seapine Road

Price$6,250,000

Est. Mortgage: $/month

MLS Number 21908221

  • Single Family
  • Village North Chatham
  • Year Built 2017
  • Bathroom 6
  • Full Bathrooms 5

Completed in 2017 by the award-winning architectural firm Polhemus Savery DaSilva, this stunning 5,850 four-bedroom waterfront home is newly enhanced with upscale finishes by renowned designer Lisa Tharp -and sold with its bespoke furnishings. The open-layout main level boasts a stunning view-filled great room with chef's kitchen, dining room, screened porch that overlook Crows Pond, a spectacular stone patio, infinity pool and deck - a perfect venue for 4th of July fireworks. Coffered ceilings, monochrome palettes, detailed built-ins and striking light fixtures catch the eye. Guests can retreat to a first-floor family suite with private patio and spa bathroom. Above, is a spectacular master suite and bedroom overlooking the water as well as a children's room and central loft. Luxurious amenities extend to the lower level with a bunk room, full bath, entertainment and game room leading to an outdoor shower. This turnkey offering is the ultimate resort style getaway with all the top indoor and outdoor amenities as well as ample space for spillover company and entertaining.

Listed by Chris Rhinesmith of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

178 Old Harbor Chatham MA 02633

Chatham, MA178 Old Harbor Road

Price$2,499,900

Est. Mortgage: $/month

MLS Number 21907570

  • Single Family
  • Village Chatham
  • Year Built 2020
  • Bathroom 5
  • Full Bathrooms 4

This spectacular walk to town setting is a perfect opportunity to live in a brand-new construction Eastward Companies home in a private in-town setting with a pool. Spanning 3.412 sf., the shingle-style home features a spacious open floor plan with luxurious amenities, and on-trend designer finishes. The home welcomes with a light-filled great room, coffered ceilings and a gas fireplace. The custom kitchen has a grand 17' center island, state of the art appliances, desk area, walk-in pantry and butler's pantry. There is a dining room, mudroom, powder room, laundry and luxurious master suite. Above, there are two en-suite bedrooms, and an en-suite bonus room above the two-car garage. The grounds are exceptionally landscaped with privacy hedges and lush landscaping.

Listed by Chris Rhinesmith of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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

This site was last updated January 25, 2020. All properties are subject to prior sale, changes, or withdrawal.

Jack Bohman Real Estate 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.