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.

141 Cotchpinicut, Chatham, MA 02650

Price$4,500,000

Est. Mortgage: $/month

MLS Number 21805829

  • Single Family
  • Village North Chatham
  • Year Built 1734
  • Bathroom 8
  • Full Bathrooms 7

If you are looking for spectacular views you will not want to miss this exceptional estate that sits high on a hill overlooking Pleasant Bay on coveted Cotchpinicut Road. With plenty of room for guests, you will be charmed by the ambiance of this circa 1740 home with all of the updates required for today's stylish living. It features eight bedrooms including an opulent master suite and seven baths , wide pine floor boards, original paneling in the older sections, a large chef's kitchen, gas fireplaces in the den and kitchen, three wood burning fireplaces, a finished basement for the kids, separate apartment, office and man cave by the garage. With a heated inground pool, beach, two decks for entertaining, there is plenty of privacy but also great gathering places for all.

Listed by Evelyn S Doane of William Raveis RE & Home Serv.

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

398 Cedar, Chatham, MA 02633

Price$2,450,000

Est. Mortgage: $/month

MLS Number 21805306

  • Single Family
  • Village Chatham
  • Year Built 2018
  • Bathroom 6
  • Full Bathrooms 5

New construction custom built by Morgan and Sons on the loop to town! Shingled, Cape Cod style home boasts 6BRs on .84 acres and includes an 940 sf accessory building (home office/art studio) and future pool potential.Tasteful design with quality materials includes a light filled Cook's kitchen w/ island and pantry, opening to great room with gas fireplace, vaulted ceilings and built ins.Sliders lead to private rear deck. First floor sitting room and private first floor master suite. Upstairs offers 3 additional bedrooms and playroom/study.The walk out lower level includes two additional bedrooms, full bath and second great room. Central a/c, attached two car garage w/ additional garage space under accessory building, first floor laundry, irrigation, stone walls and outdoor shower.

Listed by Lori L Fanning Smith of Pine Acres Realty

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

11 Aunt Zilpas, Chatham, MA 02633

Price$725,000

Est. Mortgage: $/month

MLS Number 21805135

  • Single Family
  • Village Chatham
  • Year Built 2004
  • Bathroom 3
  • Full Bathrooms 2

Picture perfect Cape, built in 2004, has been meticulously cared for and thoughtfully designed - bathed in natural light. The first floor offers a cook's kitchen with open dining and a spacious living room with wood burning fireplace. The large first floor master suite features a private bath and walk-in closet. The floors are polished oak. The second floor offers a bedroom and bath shared with a loft and large finished room for overflow. The irrigated landscaping is pristine with flowering hydrangeas and tall privacy trees. There is the possibility of a pool as well. The property is located just 5 minutes by car to Hardings Beach and Ridgevale Beach and the same to downtown. The bike trail can be accessed by a path in the immediate neighborhood. A truly lovely home!

Listed by Trudi D Burrows of Pine Acres Realty

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

357 Stony Hill, Chatham, MA 02650

Price$1,289,000

Est. Mortgage: $/month

MLS Number 21805001

  • Single Family
  • Village North Chatham
  • Year Built 2003
  • Bathroom 4
  • Full Bathrooms 3

This very spacious 3,828 square foot, 4+ Bedroom, 3-1/2 bath Cape allows for one-floor living, but will accommodate all your visiting friends and family! You'll enjoy a lovely granite kitchen and two adjacent dining areas. Bright living room w/wood-burning fireplace & built-ins. Large multi-purpose loft, separate den, and bonus room. 1st floor Master BR suite & 1st floor laundry. Other highlights are an expansive deck running the length of the house, hardwood floors, french and pocket doors, natural gas heat, tons of closets, huge walk-out basement, and 2-car garage. This private 1.3 acre property includes a nice yard with room for a pool, well-irrigation, and outside shower. Conveniently located 1/2 mile to water and less than 10 minutes to Town. Rental investment potential, too.

Listed by Lori Jurkowski of Kinlin Grover Real Estate

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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

84 Barcliff, Chatham, MA 02633

Price$2,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 21804475

  • Single Family
  • Village Chatham
  • Year Built 2016
  • Bathroom 5
  • Full Bathrooms 4

New construction! Luxurious home with captivating details a short stroll from downtown Chatham. Thoughtful blend of comfort and elegance, this 4 BD, 4.5 BA home sits on 1.14 private acres.The 4,600sf design shows attention to detail with an open floor plan, 1st floor master suite w/ vaulted ceilings, gas fireplace, hardwood antique pine floors, gourmet kitchen w/ granite countertops, stainless steel appliances & custom cabinetry, laundry room & sunroom.The eat-in kitchen is large enough for casual dining and connects to a private dining area.Upstairs features 2 bedrooms plus a 2nd floor master bedroom and bath, spacious loft, office & 2nd laundry room.The patio provides a space to enjoy quiet mornings and the private yard is large enough to accommodate a pool, fire pit & outdoor kitchen.

Listed by Jack D Bohman of oldCape Sotheby's International Realty

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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

62 Hillcrest, Chatham, MA 02650

Price$2,375,000

Est. Mortgage: $/month

MLS Number 21803721

  • Single Family
  • Village North Chatham
  • Year Built 1988
  • Bathroom 4
  • Full Bathrooms 3

BREATHTAKING VIEWS of Chatham Harbor and Atlantic Ocean from custom built North Chatham home. Inviting and graceful open floor plan with vaulted ceilings, clean lines, creative details, and fabulous ocean views. Two spacious master bedroom suites plus additional bedroom and several multipurpose rooms for sitting, study or games--something for everyone! Open floor plan looks out onto wide ocean views and hosts living, dining, kitchen and auxiliary grill kitchen. Perimeter Azek decks host alfresco dining, entertaining, relaxing. Natural gas heat, central air, private well for irrigation, whole-house generator, oversize two-car garage, exercise room plus plenty of room for a pool! Walk to Chatham shops, restaurants and theater from this private quiet neighborhood. Elevated above flood zone, the home is privately set on quiet street a stone's throw to public access to Chatham Harbor. This inspired and intelligent home is in a class by itself!

Listed by Fran I Schofield of Robert Paul Properties, Inc.

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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

324 Deer Meadow, Chatham, MA 02633

Price$899,900

Est. Mortgage: $/month

Pending

MLS Number 21803590

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

Rare opportunity to have your own private resort at this newly listed home in the Riverbay neighborhood of Chatham. This expansive 4 bedroom, 3.5 bath home has plenty of living space for everyone with a living room, dining room, kitchen, heated sun room plus a large walk-out finished lower level with fireplace. Beautifully landscaped setting with irrigated grounds (irrigation and pool on a well), large refurbished heated in ground pool and tennis court all on over an acre of land. Plenty of space for a large family and a wonderful home for entertaining. Besides the recreation area in the basement there is an extra bedroom, laundry room and workshop area.

Listed by Doug Grattan of Chatham Properties Group

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

155 & 157 Bridge, Chatham, MA 02633

Price$4,995,000

Est. Mortgage: $/month

MLS Number 21803466

  • 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 Pine Acres Realty

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

369 Old Harbor, Chatham, MA 02633

Price$4,950,000

Est. Mortgage: $/month

MLS Number 21803306

  • Single Family
  • Village Chatham
  • Year Built 1839
  • Bathroom 22
  • Full Bathrooms 20

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 Carol M Edmondson of Cape Cod Village Realty

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

342 Pleasant, Chatham, MA 02659

Price$1,099,000

Est. Mortgage: $/month

MLS Number 21803024

  • Single Family
  • Village South Chatham
  • Year Built 1950
  • Bathroom 2
  • Full Bathrooms 2

Exceptional location! Pleasant Beach is only four houses away from this updated 3 bedroom home with coastal accents. The first story features a light, updated kitchen and wine bar area, a dining area with wood burning fireplace and comfortable living room with views of Nantucket Sound. The second story is a private master bedroom with en-suite bath. Amenities include gleaming hardwood floors, split system AC, whirlpool bath, natural gas, stack washer & dryer, 1-car garage, patio, deck & large yard. Walk to South Chatham village to enjoy restaurants, the library, houses of worship and an old fashioned hardware store. Would make a wonderful weekend get-way, year round home or investment property. This home is not in the flood zone & offers rental potential of $4,950 per week in season.

Listed by Shane K Masaschi of Kinlin Grover Real Estate

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

114 Cranberry, Chatham, MA 02650

Price$4,995,000

Est. Mortgage: $/month

Pending

MLS Number 21802938

  • Single Family
  • Village North Chatham
  • Year Built 2017
  • Bathroom 9
  • Full Bathrooms 8

''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 Ward H Brown, III of William Raveis RE & Home Serv.

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

432 Old Harbor, Chatham, MA 02633

Price$2,650,000

Est. Mortgage: $/month

MLS Number 21802860

  • Single Family
  • Village Chatham
  • Year Built 1900
  • Bathroom 4
  • Full Bathrooms 3

Introducing the Bluffs at North Chatham. Offering a commanding presence on the crest of Old Harbor Road, this Federal style home is beautifully sited on a large lot with elevated views of Chatham Harbor. Originally built in 1900 and updated with modern amenities, this home has 6+BR, 3.5BA, a 3 car garage and an expertly designed mahogany porch. The main level features a chef's kitchen with a large island leading to a dining area and an inviting living room with vaulted ceilings and fireplace. There is an adjoining formal dining room, office, mud room, laundry and additional space with a den, kitchen and laundry room. All the bedrooms are above including a master bedroom en-suite, a third floor bunk/activity room, 3 baths and a library. The grounds are expansive with room for a pool

Listed by David C Carter of Pine Acres Realty

{$office->Name}

oldCape Sotheby's International Realty
210 Orleans Road A&B
P.O. Box 385
North Chatham MA, 02650
Office: 508.945.8800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 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.

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 August 21, 2018. 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.