Town of Chatham

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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1239 Main Chatham MA 02633

Chatham, MA1239 Main, Unit X18

Price$899,000

Est. Mortgage: $/month

MLS Number 22105811

  • Condominiums
  • Garage Spaces 1
  • MLS Status Active
  • Village Chatham
  • Zoning R20

A rare opportunity at Oyster Pond Chatham Ma Cape Cod. 1650 square ft. 3 bedrooms, 2 bath Town House Condo on 18+ Acres with only 32 Units. Beautifully landscaped! Salt water swimming pool, Tennis court, Dock, Walking paths along Oyster Pond. ''Inlet to ocean''. With picnic areas. Condo has updated kitchen with newer appliances and dining area. Updated bathrooms with a bonus room on the first floor for possible bedroom. Also this unit comes with a freestanding garage deeded. Partially furnished if you choose. Please email for a video. Will send on request.

Listed by Jennifer Stein of Homelister,Inc.

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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315 Pleasant Chatham MA 02659

South Chatham, MA315 Pleasant Street

Price$1,200,000

Est. Mortgage: $/month

MLS Number 22105773

  • Single Family
  • Village South Chatham
  • Year Built 1977
  • Bedrooms 3
  • Bathroom 3

This beautiful custom colonial style home is just 2/10 of a mile to Chatham Tides and the sandy Pleasant Street Beach! Multiple outdoor hosting areas in this home, which include a large porch, a balcony off the primary suite with ocean views and a newly added 15x15 patio perfect for grilling and entertaining. The windows have been replaced (2011) along with the heating system (2016) and the roof (2018). Newly renovated main level with hard wood floors, stair case, kitchen cabinets, lighting, granite countertops and appliances (2018). Renovated entire upper level with vinyl plank floors, and the two bathrooms full bathrooms, tile, flooring, showers, cabinets, mirrors, lighting (2019). Poured concrete basement and an attached garage with ample storage. New outdoor shower with a hold/cold feature and double spigot with a fenced in back yard complete this home!

Listed by James P O'Brien of Redfin Corporation

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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37 Jessies Chatham MA 02633

Chatham, MA37 Jessies Landing

Price$1,899,900

Est. Mortgage: $/month

MLS Number 22105728

  • Single Family
  • Village Chatham
  • Year Built 2021
  • Bedrooms 3
  • Bathroom 5

Welcome to 37 Jessie's Landing, a new home in an Eastward Companies development located in the heart of Chatham and minutes to town. This superbly designed home lends itself well to gracious seaside living. The striking open floor plan blends the living and kitchen areas nicely together while including a bright sunroom to the mix just off the dining area. Three spacious bedrooms, all with their own private full baths, include an elegant first floor master suite. Additional notables include a large bonus room with a full bath over the garage, a first floor office, pantry, laundry room, powder room, 2 car garage. Exquisite woodwork and high-end finishes throughout reflect the attention to detail that's a trademark of an Eastward Companies home. Room for a pool.

Listed by Doug Grattan of Chatham Properties Group

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$
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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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162 Cedar Chatham MA 02633

Chatham, MA162 Cedar Street

Price$1,340,000

Est. Mortgage: $/month

MLS Number 22105712

  • Single Family
  • Village Chatham
  • Year Built 1860
  • Bedrooms 3
  • Bathroom 2

Location is everything! ''Windsong Cottage'' is located on the back loop to town and offers access to a beautiful deeded path to the Oyster Pond. Boat , kayak and fish from this hidden spot. Classic Antique, 3BR ,2 bath home is framed by a newly planted privet hedge and offers inviting spaces and wide width pine flooring in many rooms.. First floor master bedroom , sunny eat in kitchen with vaulted ceilings and skylight, dining room and front to back living room complete the first floor. Two additional bedrooms are on the second floor. Also offered are a one car garage, rear deck and out door shower,. Enjoy as is or renovate. Included in sale are owner's plans to help with your vision. Proposed plans are subject to approval and seller makes no representations. A split system including heat and a/c is being installed in November. Town sewer is slated for this location and may afford an additional bedroom. Rented during 2021 at $5000 a week.

Listed by Lori L Fanning Smith of Compass Massachusetts,LLC

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$
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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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39 Seaview Chatham MA 02633

Chatham, MA39 Seaview Terrace

Price$4,650,000

Est. Mortgage: $/month

MLS Number 22105668

  • Single Family
  • Village Chatham
  • Year Built 2007
  • Bedrooms 4
  • Bathroom 7

This stunning property is privately set back and offers sweeping vistas of Chatham Seaside Links and distant views of the Atlantic. The open floor plan seamlessly blends indoor and outdoor living with breathtaking views from nearly every room. Architecturally striking, the shingle style gambrel features elegantly appointed interiors, quality craftsmanship, and ample living space with four bedrooms and six and half baths. The impressive main level includes a state-of-the-art kitchen and adjoining great room with fireplace and dining area - both with sliding doors that frame the sublime outdoor living room. The media room with full bath serves as a relaxing haven. Above, are three view-filled en-suite bedrooms and a home office. The primary suite exemplifies modern luxury with its chic interior design and impressive resort-style master bath. The residence offers ample accommodations with a generously sized lower level that comprises an en-suite bedroom and adjoining entertainment room with fireplace and doors to the enticing grounds by Hawk Design. The walkout finished lower level is included in the 3,533+ of living space. The home is complete with an oversized one car garage.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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111 Stephen Chatham MA 02633

Chatham, MA111 Stephen Drive

Price$950,000

Est. Mortgage: $/month

MLS Number 22105518

  • Single Family
  • Village Chatham
  • Year Built 1998
  • Bedrooms 4
  • Bathroom 3

Does your dream Cape Cod home have room for a pool or tennis court? Look no further than 111 Stephen Dr in West Chatham. Located on a private 1.5 acre lot abutting a cranberry bog, this well maintained, custom built 4 bedroom, 3 bath Cape offers an open floor plan, hardwood floors, fireplaced living room and a guest suite over the garage with separate entrance. Just minutes to West Chatham village center, Hardings Beach and downtown Chatham. Plenty of room for family and friends and a favorite summer rental offering attractive rental income.

Listed by Ella Leavitt of Kinlin Grover Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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86 Queen Anne Chatham MA 02633

Chatham, MA86 Queen Anne Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 22105314

  • Single Family
  • Village Chatham
  • Year Built 1846
  • Bedrooms 6
  • Bathroom 7

Exclusive - Deeded access to Oyster Pond....presenting the ''Corner Pearl'' where this property combines the charm of a sea captains house with a fresh updated design overlooking Oyster Pond. You will be captured by the opportunity to rent this blissful getaway, or perhaps...make it your forever home. This renovated home comes complete with 6 bedrooms, 6.5 baths, almost 4,000 square feet of living space that sits on almost half an acre. It is perfect for a family compound, as there are two independent structures: the main house features a spacious custom chef's kitchen, including Sub Zero cabinet faced refrigerator, 5 burner stove, double ovens, pantry storage, beamed ceiling and wood stove. The kitchen opens to a large multi-functional space: a dining room with an abundance of sunlight, moonlight and views of the pond. Beyond the kitchen is the living room with gas fireplace, game/tv room, and office space, all with great natural light. Beyond this, is the first-floor primary suite with his and hers baths. Heading to the second floor you have 3 large bedrooms and two full baths. The detached garage with separate guest space features a fireplaced living room, 2 bedrooms and 2 bathrooms. The expansive patio with outdoor lighting is where you will end your day with a magnificent sunset. Let us not forget the quaint, pillared corner porch with views of Oyster Pond! Walk to Town, walk to the beach....

Listed by Diane Donahue and Kathy A Doyle of Gibson Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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69 Strong Island Chatham MA 02633

Chatham, MA69 Strong Island Road

Price$2,799,900

Est. Mortgage: $/month

MLS Number 22105360

  • Single Family
  • Village Chatham
  • Year Built 1964
  • Bedrooms 3
  • Bathroom 4

What a location! This beautifully renovated coastal home with high end fixtures and beautiful details ticks off plenty of boxes on someone's wish list. It offers splendid views of Pleasant Bay, direct water front on one of Chatham's most picturesque ponds, a gorgeous sandy association beach, and use of a deep water dock for easy boating convenience. Located in one of Chatham's most walkable and water-oriented communities, this home puts you right in the center of it all. Set on almost an acre of land, and sitting directly on Fox Pond, this home provides year-round privacy and ever changing vistas. The home is designed to maximize the views both on the first and second floors. The first floor features a large casual living room with gas fireplace and access to an expansive deck that runs along the back of the home, a spacious kitchen perfect for hosting large gatherings, a powder room, and a master suite with a gas fireplace, spa-like bath, and a walk-in closet. The second floor has 2 additional bedrooms, one being a two-room suite with private bath, and a full bathroom with high end fixtures. The lower level has a family room and walk-out access through the garage. Additionally the home has both second floor and lower level laundry areas, 2 dishwashers, 3 gas fireplaces, irrigation and landscape lighting. Decorated in a coastal theme and meticulously maintained, this home is move-in ready.

Listed by Doug Grattan of Chatham Properties Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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2653 Main Chatham MA 02659

MLS Number 22105225

  • Commercial
  • Property Type Display D
  • MLS Status Active
  • Village South Chatham
  • Zoning SC

This multi-use property is located on the highly visible Route 28 in the midst of a walkable neighborhood which features many seasonal rentals and B&Bs. Currently the business is a very successful 42 seat full service restaurant with a 5-7 seat bar with a full liquor license. Their impeccable reputation has been maintained by it's owner operators for the past 20 years. The property features two additional living spaces with a two bedroom, full bath apartment w/galley kitchen, large Livingroom w vaulted ceilings and a walk out deck along with a newly renovated studio apartment w/full bath, a loft and walkout patio. There are private entrances to all units, a side driveway for parking. There is a large fenced in back yard w/two sheds and a walk-in commercial cooler. Located 1/2 mile from the beach, along the bus route and close to the bike path this location has a history of full occupancy and an award winning reputation as a local culinary treasure. Past business uses include a general store, a coffee shop, real estate offices and its current full service seasonal restaurant with additional residential rental units. This is a turn key restaurant and fully permitted.

Listed by Charles D Kipnes of Premier Commercial

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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2653 Main Chatham MA 02659

South Chatham, MA2653 Main Street

Price$1,200,000

Est. Mortgage: $/month

MLS Number 22105226

  • Single Family
  • Village South Chatham
  • Year Built 1860
  • Bedrooms 3
  • Bathroom 3

This multi-use property is located on the highly visible Route 28 in the midst of a walkable neighborhood which features many seasonal rentals and B&Bs. Currently the business is a very successful 42 seat full service restaurant with a 5-7 seat bar with a full liquor license. Their impeccable reputation has been maintained by it's owner operators for the past 20 years. The property features two additional living spaces with a two bedroom, full bath apartment w/galley kitchen, large Livingroom w vaulted ceilings and a walk out deck along with a newly renovated studio apartment w/full bath, a loft and walkout patio. There are private entrances to all units, a side driveway for parking. There is a large fenced in back yard w/two sheds and a walk-in commercial cooler. Located 1/2 mile from the beach, along the bus route and close to the bike path this location has a history of full occupancy and an award winning reputation as a local culinary treasure. Past business uses include a general store, a coffee shop, real estate offices and its current full service seasonal restaurant with additional residential rental units. This is a turn key restaurant and fully permitted.

Listed by Charles D Kipnes of Premier Commercial

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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62 Oyster Pond Furlong Chatham MA 02633

Chatham, MA62 Oyster Pond Furlong

Price$2,850,000

Est. Mortgage: $/month

MLS Number 22105012

  • Single Family
  • Village Chatham
  • Year Built 1800
  • Bedrooms 4
  • Bathroom 2

The Captain John Crowell House (c. 1800) is nestled on 2.54 acres surrounded by conservation land. It has been lovingly maintained and restored by the same family for 3 generations, and now it opens its doors to you. This home combines all of the charm of an antique with a beautifully updated kitchen and spectacular baths. The chef's kitchen features a Wolf dual-fuel range, Sub-Zero fridge, Miele dishwasher, & many other high-end fixtures as well as one-of-a-kind Belgian blue stone flooring with embedded marine fossils. Hand-planed wainscoting, gorgeous woodwork, three working fireplaces and antique pine floors known as Kings Boards all add to its charm. This 4 bedroom, 2 bath home offers exceptional privacy while sitting just a stone's throw from Oyster Pond for swimming, kayaking, and access to Nantucket Sound and a short stroll to all Chatham has to offer--restaurants, shopping, band concerts, and Mondays on Main music and entertainment in the summer. Lighthouse and Hardings Beaches are just a short drive away, as well. Come visit and witness for yourself the charm, the privacy, and the beautiful gardens.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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119 Scatteree Chatham MA 02650

North Chatham, MA119 Scatteree Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 22104983

  • Single Family
  • Village North Chatham
  • Year Built 1900
  • Bedrooms 6
  • Bathroom 4

This 6 bedroom, 4 bath waterview home presents a unique opportunity for you to turn back the clock and escape to a simpler time, place, and pace in historic North Chatham.Nicely sited on high ground overlooking conservation land, a tidal salt pond, and Pleasant Bay, this circa 1900's homestead will be a welcoming and comforting retreat for family and guests.Expansive open lawn areas are ideal for outdoor recreation and two nearby Town Landings offer perfect launching areas for waterfront activities.Return to Old Cape Cod. Come home to 119 Scatteree Road, North Chatham.

Listed by David H Doherty and Jack P Farrell of Kinlin Grover Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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 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 27, 2021. 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.