Homes For Sale Chatham MA

Chatham is located at the ‘elbow’ of Cape Cod and was settled by the English in 1664 at which time it was called Monomoit; it soon became a whaling, fishing and shipping center. Its location has kept it a quaint village with central main street shopping ideal for strolling. There are concerts held during the summer on the Main Street gazebo much like many of the other cape villages.  Also from main street it is not too far to stroll to Arey's Pond (check out the boat yard!), Stage Harbor, Chatham Lighthouse, Chatham Bars Inn and the Chatham Break.

Although one of the smaller Cape Cod towns, Chatham, makes up for its size in the available recreational opportunities, fishing, boating, swimming, Cape Cod Baseball League games, Chatham Orpheum Theater and much more.  Additionally many vacationers and second homeowners find Chatham convenient for its airport access and potential for charter flights.

Chatham has approximately 24 square miles with 33% being water. It features the Monomoy National Wildlife Refuge on Monomoy Island. The current population is approximately 6,000. The town’s villages include Chatham proper, Chatham Port, North Chatham, West Chatham and South Chatham. It is bordered by Harwich to the west, Pleasant Bay and Orleans to the north, the Atlantic Ocean to the east and Nantucket Sound to the south.

Chatham Real Estate Searches:

$300k-$500k | $500k-$1M | Luxury $1M+Condominiums | Walk to Water

Below, browse all Chatham real estate for sale. Contact the Cape Cod Chatelains with your questions about buying real estate on the Cape.

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52 Oyster Bluff Chatham MA 02633

Chatham, MA52 Oyster Bluff

Price$8,995,000

Est. Mortgage: $/month

MLS Number 22304126

  • Residential
  • Bathroom 6
  • Bathrooms Total Decimal 5.5
  • Bedrooms 5
  • Full Bath 5

A rare offering in Chatham....Formerly part of The Plum Estate, this salt waterfront home offers stunning water views over The Oyster Pond , magnificent pool, spa and patio area and large dock capable of handling multiple boats. This 5BR home underwent a meticulous renovation between 2013-2016 ,preserving original details while optimizing the finest of today's conveniences. The original double doors open unto a truly Great room with high ceilings, fireplace, stunning water vistas and room for multiple sitting and dining areas. Adjacent is the renovated kitchen with center island, breakfast nook and ample cabinetry, A luxurious study/media room , half and full bath complete the first floor. The left side of the house opens to a private ''napping house'' with second study/media room, full bath and bedroom. The second floor offers a spacious primary suite with double closets and full bath. Three additional bedrooms share two baths. The lower level boasts a games and more room with pool table ,and additional table seating and lounging space. Coastal gardens and lawns surround for privacy. Close proximity to shopping and downtown Chatham.

Listed by Lori L Fanning Smith of Compass Massachusetts,LLC

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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2388 Main Street Chatham MA 02659

South Chatham, MA2388 Main Street

Price$1,500,000

Est. Mortgage: $/month

MLS Number 22304072

  • Residential
  • Bathroom 4
  • Bathrooms Total Decimal 4
  • Bedrooms 5
  • Full Bath 4

Rare opportunity featuring a legal 2 family even though it is currently functioning as a single family home. With 5 bedrooms, 4 full baths, and a host of impressive features, this home offers the perfect blend of elegance and functionality.Step into a world of culinary delight with a gorgeous kitchen, complete with a custom walk-in pantry, catering to your every need. The high ceilings throughout the home create an open and airy ambiance, elevating the overall sense of luxury.This property also features a convenient mudroom to keep your space organized and a private home office, perfect for remote work or creative pursuits. The walk-out finished lower level adds even more versatility to this home, whether for entertainment, relaxation, or fitness or extra income.Outside, the large private yard beckons for outdoor enjoyment, providing ample space for recreation and leisure. And with its prime location in Chatham, MA, you'll have easy access to all the town's amenities and stunning beaches.Experience the pinnacle of coastal living in this beautifully renovated Chatham property.

Listed by W&W Boston/Cape Cod Connection and Joan Witter of Compass Massachusetts,LLC

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$
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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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71 Crowell Road Chatham MA 02633

MLS Number 22304075

  • CommercialSale
  • Modification Date 09/21/2023
  • Property SubType Restaurant
  • Address 71 Crowell Road
  • Lot Size Square Feet 10,890

Chatham Village For Sale - renovated, turn- key cafe & bakery. Longtime home to the Chatham Village Bakery and most recently EmmaBelle's, this prime location is available for a new operator. Centrally located on Crowell Road, the property is convenient to all Chatham and Lower Cape points. Thoroughly renovated in 2023, the +/- 2,040 square foot space features 16 seats for dining inside or al fresco on the professionally landscaped patio. The front of the house also includes a full service coffee & espresso counter, multiple display & beverage cases, and an ADA accessible customer half bath. The front of the building is fully climate controlled with gas forced hot air heat/central cooling. The back 2/3 of the building consists of professional cooking & prep space including a new hood system, range, and ovens. There is ample cooler & freezer space with the potential to add more. There is a second, employee half bath, private manager's office, and interior access to the basement. The property has onsite parking, excellent signage & visibility, and is connected to municipal sewer. Electrical service to the property is single phase power with a 3-phase converter.

Listed by Bradford Kuhrtz of Commercial Realty Advisors,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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 Sky Way Chatham MA 02633

Chatham, MA150 Sky Way

Price$979,900

Est. Mortgage: $/month

Open House

MLS Number 22304110

  • Residential
  • Next Open House: Sun 10/1 1:00 pm. to 3:00 pm.
  • Parking Spaces 4
  • Bathroom 2
  • Bathrooms Total Decimal 2

This classic cape style home is truly turn key! Beautifully renovated and meticulously maintained, this cream puff greets you at the front door with expansive cathedral ceilings and an airy open floor plan. She features an updated kitchen and bathrooms with granite counters, newer split system AC, hardwood floors and first floor laundry. Enjoy an additional 350 square feet of finished space in the lower level. With deeded access to White Pond, stroll across the street and enjoy kayaking, swimming, canoeing and fishing! Enjoy immediate access to the Bike Path. Close to downtown shopping & dining, The Orpheum Theatre, Chatham market and all charming Chatham has to offer. This lovely property has a rental history of $4500 per peak weeks, so whether you are looking for your quintessential Cape summer home or you are an investor adding another smart investment to your portfolio, let us introduce you to this coastal gem! Please see the Feature Sheet in Documents.

Listed by Susan Piracini of Compass Massachusetts,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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36 Bearses Byway Chatham MA 02633

Chatham, MA36 Bearses Byway

Price$1,575,000

Est. Mortgage: $/month

MLS Number 22303947

  • Condo
  • Parking Spaces 1
  • Bedrooms 3
  • Full Bath 2
  • Bathrooms Total Decimal 2.5

Welcome to this charming three bedroom, three bath townhome ideally nestled on a quiet lane in town just off Main Street. This lovely residence offers a perfect blend of comfort, style, and convenience to experience the very best of Chatham. As you step inside, you'll immediately feel at home in the warm and inviting atmosphere of this townhouse. The spacious and thoughtfully designed layout provides ample room for relaxation and quality time with your loved ones. The living area boasts cozy furnishings and large windows that allow natural light to flood the space, creating a bright and cheerful ambiance. The bedrooms are all spacious enjoying soaring ceilings and an abundance of natural light. Come and experience the carefree lifestyle of Chatham in this beautiful turnkey home.

Listed by Team Guthrie - Mabile and Tony Guthrie of Berkshire Hathaway HomeServices Robert Paul Properties

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$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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21 Northwood Road Chatham MA 02633

Chatham, MA21 Northwood Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 22303852

  • Residential
  • Bathrooms Total Decimal 2
  • Full Bath 2
  • Bathroom 2
  • Bedrooms 3

Enjoy this fabulous cape cod home with room for family and friends. Bike trail just around the corner and Nantucket Sound beaches a bike ride away. Immaculately maintained with hardwood floors throughout the first floor. Primary with private bath, living room, dining area, and family room with cathedral ceiling and gas fireplace. Two large bedrooms with skylights and full bath on the second floor. On those hot humid days enjoy the central air inside and the inviting salt water in-ground gunite pool outside. Beautifully landscaped yard - deck with retractable awning and patio. New gray vinyl fence, new AC in 2023, and pool now salt water. Truly a special place that everyone will want to call home.

Listed by Judith L Smith of John C Ricotta & Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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148 Old Queen Anne Road Chatham MA 02633

Chatham, MA148 Old Queen Anne Road

Price$985,000

Est. Mortgage: $/month

MLS Number 22303807

  • Residential
  • Parking Spaces 5
  • Full Bath 3
  • Bedrooms 4
  • Bathrooms Total Decimal 3

Renovated and ready for your relaxation! Aptly named ''Tucked Away,'' hidden privately off Old Queen Anne Road in Chatham, this sundrenched property offers easy access to the bike path and White Pond and is a quick stroll to town. You'll enjoy cooking in your brand new kitchen with open sight lines to your vaulted, four season sunroom boasting ideal flow for indoor/outdoor entertaining. Dine al fresco under the stars on your backyard patio before retreating to your cozy living room complete with fireplace with a good book. End the day in your new primary bedroom with ensuite bathroom from some solid R&R. Three additional bedrooms provide plenty of room for extended family and guests. Close to saltwater beaches and world class golfing, shopping and dining--and already connected to town sewer. Come experience the good life in Chatham today!

Listed by Christa Zevitas of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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88 Happy Valley Road Chatham MA 02633

Chatham, MA88 Happy Valley Road

Price$1,399,000

Est. Mortgage: $/month

MLS Number 22303833

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Full Bath 3
  • Bathrooms Total Decimal 3

This property is truly a special retreat. Waterfront on flooded cranberry bog. Close to Ridgevale Beach. This home built in 2011 has 3 bedrooms, 3 baths, great room, family room and a wonderful screened porch (24 x 16). The great room has 6 skylights, wood beams, cathedral ceiling, gas fireplace and is open to the kitchen.There are 2 ensuite bedrooms one on the first floor and one on the second. and a fabulous family room in the lower level.

Listed by Judith L Smith of John C Ricotta & Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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31 Great Hill Road Chatham MA 02633

Chatham, MA31 Great Hill Road

Price$1,095,000

Est. Mortgage: $/month

MLS Number 22303804

  • Residential
  • Bathrooms Total Decimal 2
  • Bathroom 2
  • Bedrooms 2
  • Full Bath 2

Come view this two bedroom two bath home with an office perfect for those working from home. Lots of living space for family and friends - living room with fireplace and family room overlooking the back yard. Close to bike trail, basketball, and tennis courts. Wonderful sunroom, screened porch and enormous deck leading out to woodburning fire pit. Large lot with expansion possibilities.

Listed by Judith L Smith of John C Ricotta & Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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407 Orleans Road Chatham MA 02650

North Chatham, MA407 Orleans Road

Price$495,000

Est. Mortgage: $/month

MLS Number 22303725

  • Condo
  • Bathroom 2
  • Full Bath 2
  • Bedrooms 2
  • Bathrooms Total Decimal 2

Just finished a complete remodel on this unit. Some of the recent improvements include new windows, new flooring, new kitchen cabinets with granite counters and stainless appliances. Bathrooms have custom tile with new vanities, and all new plumbing fixtures. Condo features small deck off of kitchen and a 12'x12' storage room in basement. Master bedroom has lots of closet space and a master bath .Condo also comes with a carport for one vehicle.

Listed by Shane Pacheco of SMP Realty Development Co. LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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82 Diane Drive Chatham MA 02633

Chatham, MA82 Diane Drive

Price$895,000

Est. Mortgage: $/month

MLS Number 22303497

  • Residential
  • Full Bath 1
  • Bathrooms Total Decimal 1
  • Bathroom 1
  • Bedrooms 2

Location, location, location! Looking to build or rehab, preview this 2-bed, 1-bath cottage, being sold ''As Is'. As part of the Buck's Creek Association members access the private bridge to Ridgevale Beach, one of Chatham's finest Nantucket Sound beaches. Please note: Cesspool system in place requires upgrading to Title V at buyer's expense within 90 days of purchase, buyer responsible for all permitting, expenses and due diligence. Home is not in flood zone. Don't miss out on 82 Diane Drive, Chatham!

Listed by Shane K Masaschi of Kinlin Grover Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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249 Ridgevale Road Chatham MA 02633

Chatham, MA249 Ridgevale Road

Price$1,200,000

Est. Mortgage: $/month

MLS Number 22303437

  • Residential
  • Parking Spaces 3
  • Full Bath 3
  • Bathrooms Total Decimal 3
  • Bathroom 3

This beautifully updated home in 2022 is only .3 miles from the picturesque sandy beach ''Ridgevale Beach,'' making it an ideal choice for a summer getaway or a profitable rental investment. Step into the sun-filled enclosed front porch and on into the sunny open living room and dining area. The kitchen was tastefully redone with quartz counters, a stainless 6-burner gas stove, a dishwasher, a beverage refrigerator, and a retro refrigerator. In addition, the kitchen has access to a large deck for outdoor dining and entertaining. The first-floor bedroom, laundry, and a full bathroom complete the first floor. The second floor boasts a spacious primary en-suite with a stunning new bath. Great bonus rooms and a full bath is on the lower level, accessed from the walk-out basement.Great rental investment property or your Cape Cod summer retreat at one of Chatham's finest beach neighborhoods.

Listed by Sandra Tanco of Kinlin Grover Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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 TourAsk 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 Chatelain 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 Chatelain Real Estate shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated September 26, 2023 4:22 AM EDT. All properties are subject to prior sale, changes, or withdrawal.

Chatelain 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.