Chatham Massachusetts Real Estate & Homes For Sale

Listing Results

Sort:
  • Newest
  • Price
  • Bedrooms
  • Featured
$799,900
3bd
2ba
1365sqft
12,197Sqft

1369 Main Street
Chatham, Massachusetts 02633

Lauren T Scioletti
Sotheby's International Realty
Welcome to 1369 Main Street Chatham! This newly renovated 3 bed 2 bath home sits on a beautiful, cleared, private fenced lot , offering ample space for both relaxation and recreation. A pinch under 1400sqft of living space, the property features an attached 2 car garage, providing convenient storage and parking.
$429,000
2bd
1ba
1013sqft
130,680Sqft

409 Orleans Road # B
North Chatham, Massachusetts 02650

Debra A Bassett
Cape Cod Associates R E
Welcome to Quail Run, nestled off-the-beaten-path in beautiful North Chatham-yet convenient, easy access to all! This immaculate, delightful unit opens into a spacious, warm and welcoming living room with vaulted ceiling, hardwood floors, and new picture window overlooking a peaceful wooded area; the dining room has built-ins and the same wooded views; the efficient kitchen offers good storage, u
$4,200,000
4bd
5ba
4372sqft
14,375Sqft

107 School Street
Chatham, Massachusetts 02633

John B Burke
William Raveis Real Estate & Home Services
Beautiful, like new condition home built in 2014 by Polhemus, Savery, and Desilva in the very sought after OLD VILLAGE. Close walk to downtown, shopping, restaurants and all that Chatham has to offer..... AND Lighthouse and Water Street beaches are a close 4 minute walk away,....There are 4 large bedrooms, primary en-suites on first and second floors and 5.
$790,000
3bd
2ba
1414sqft
43,996Sqft

1761 Main Street
Chatham, Massachusetts 02633

Kathleen Phelan
Compass Massachusetts, LLC
Just around the corner from Ridgevale beach in Chatham; lies this terrific opportunity to build a large home and guest house on this 1 acre lot that backs up to a cranberry bog. This lot has potential view of the cranberry bog and is very close to Ridgevale beach. If you are looking to build a large home with a guest house and a pool or even 2 houses; this lot has many possibilities.
$790,000
43,996Sqft

1761 Main Street
Chatham, Massachusetts 02633

Kathleen Phelan
Compass Massachusetts, LLC
Just around the corner from Ridgevale beach in Chatham; lies this terrific opportunity to build a large home and guest house or 2 houses on this 1 acre lot that backs up to a cranberry bog. This lot has potential view of the cranberry bog and is very close to Ridgevale beach. If you are looking to build a large home with a guest house and a pool or even 2 houses; this lot has many possibilities.
$319,900
1284sqft
23,087Sqft

26 George Ryder Road S
Chatham, Massachusetts 02633

Doug Grattan
Christie's International Real Estate Atlantic Brokerage
Why pay rent when you can purchase your own professional office condominium? Conveniently located right off Route 28 in West Chatham, this well-maintained, turnkey office features approximately 1,284 sq. ft. of first-floor space which includes three private offices, three administrative support offices, and a conference room.
$389,000
2bd
2ba
1167sqft

912 Main Street # X209
Chatham, Massachusetts 02633

Phyllis N Power
Kinlin Grover Compass
Ready to downsize for easy living? Come home to Chatham's finest over 62 independent living community in the heart of Chatham. This 2 BED/2BAth condo has been freshly painted & offers maintenance free living, ie peace living/dining area, a '' split plan'' with Primary bedroom en-suite on one end of unit, and guest suite with en-suite bathroom on either side.
$1,200,000
3bd
2ba
1508sqft
20,473Sqft

3 Whiteleys Way
Chatham, Massachusetts 02633

Tiffany Callahan
Greer Real Estate, LLC
If you're looking for a completely renovated home done with quality finish work, this one is a dream come true! Already on town sewer with the lowest tax rate on the Cape, this Chatham beauty features one level living, a cathedral ceiling in the open concept living area, central air, a garage, and the ability to add a pool.
$1,000,000
7,010Sqft

727 Main Street
Chatham, Massachusetts 02633

Matthew P Burger
Kinlin Grover Compass
Take advantage of this last opportunity to build on a vacant lot on Main Street in downtown Chatham! This lot is 7,010 square feet (0.16 acres) located across from Chatham Veterans Field, home of the Chatham Anglers baseball team. This truly is the last opportunity to build on a vacant lot in downtown Chatham.
$869,000
4bd
2ba
2212sqft
10,890Sqft

23 Malabar Road
Chatham, Massachusetts 02633

The Bohman Hartung Group
Gibson Sotheby's International Realty
This is a wonderful opportunity in Chatham to purchase a four-bedroom, two-bath home with a beautiful backyard. The 8-room house totals 2,212 sq ft of finished living space, 1,547 sq ft on the first two floors, and an additional 665 sq ft of finished basement.
$775,000
2bd
1ba
572sqft
6,970Sqft

82 Diane Drive
Chatham, Massachusetts 02633

Doug Grattan
Christie's International Real Estate Atlantic Brokerage
The 4th of July is less than 6 months away! Here is a rare opportunity to be a stone's throw from Ridgevale Beach with private association access via the Buck's Creek Association bridge. This 2-bedroom cape style cottage is ready for rehab, or a total rebuild. It sits on an elevated bluff and is not in the Flood Zone.
$2,399,900
3bd
2ba
2366sqft
20,473Sqft

10 Pursel Drive
North Chatham, Massachusetts 02650

Doug Grattan
Christie's International Real Estate Atlantic Brokerage
Perched on a bluff in one of Chatham's most coveted locations, Summer Wind is an expanded Cape Cod classic offering the perfect blend of traditional charm and modern amenities. With deeded access to picturesque Ryder's Cove, the luxury of an association beach, and the convenience of deep-water access to Pleasant Bay and the Atlantic beyond.
$1,999,000
5bd
3ba
2875sqft
52,359Sqft

0 Reynolds Circle
Chatham, Massachusetts 02633

Derek J Greene
The Greene Realty Group
Sellers can build your custom dream home on this gorgeous 5-bedroom building lot. Private and tranquil location nestled away from the traffic of Chatham's busy main roads. See their plan below, review their other plans or bring your own! This stunning 5-bedroom ranch plan boasts a compact design with maximum impact. 9-Ft. ceilings and a grand 15 Ft.
$1,399,500
2bd
3ba
1416sqft
10,019Sqft

116 Happy Valley Road
Chatham, Massachusetts 02633

Ward H Brown, III
William Raveis Real Estate & Home Services
Located off a private way to Ridgevale Beach overlooking a majestic cranberry bog sits this cozy colonial paradise. Built in 2015 by an award winning design/build company is this very private getaway with numerous builtins and crafted spaces.
$6,995,000
7bd
8ba
5389sqft
61,855Sqft

114 Cranberry Lane
North Chatham, Massachusetts 02650

Brian W Dougherty
Corcoran Property Advisors
Sited on a beautiful private lane in a coveted North Chatham location, this custom turn-key estate with deeded access to a sandy beach on Pleasant Bay epitomizes the absolute best of coastal Cape Cod living. The 5+ bedroom Main House and 2 bedroom Guest House are like new, having been further updated since 2017 and maintained to exacting standards since.
$1,295,000
2bd
2ba
2400sqft
0.28Sqft

00 Victoria Drive
Chatham, Massachusetts 02633

Caroline M McAdams
Covell Realty Inc
Build your dream home on this beautiful lot nestled on a cul de sac in desirable Chatham. Septic design, engineering and wind and energy plan are done. Town water and gas and electric are on the street.Building packages for a Cape and Ranch are available. Capes are approximately 2400 square feet with 2.5 baths and one or two car garage.
$649,000
2bd
1ba
912sqft
37,897Sqft

127 Oak Hill Road
Chatham, Massachusetts 02633

Sarah E Gammons - Ciampa
Berkshire Hathaway HomeServices Robert Paul Properties
Almost 1 acre in a desirable quiet neighborhood. The land provides space to remodel or update the exiting house and make it your own. House needs work and is being sold As Is. Septic Inspection completed early December- passed Title V for 3 bedroom - report attached to listing.
$499,000
2bd
2ba
1013sqft
130,680Sqft

407 Orleans Road # B
Chatham, Massachusetts 02633

John B Burke
William Raveis Real Estate & Home Services
RENOVATED IN 2023...Like new 2 bedroom, 2 bath condominium of over 1013 square feet.... New windows, new flooring, new kitchen cabinets, granite counter tops and stainless steel appliances,. Bathrooms have custom tile and new vanities and all new fixtures. Small private deck and inside parking in a carport.......
$1,895,000
3bd
3ba
2532sqft
9,583Sqft

36 Ocean View Terrace
Chatham, Massachusetts 02633

Kim C Arestad
eXp Realty, LLC
Escape to your Cape Cod dream! This pristine custom-built 3-bedroom, 3-bath Cape features exceptional details and is nestled on a secluded dead-end road, surrounded by conservation land and Chatham Links Golf Course. Enjoy proximity to Veterans Field and the Chatham Anglers, downtown Chatham, and Oyster Pond.
$1,735,000
3bd
2ba
2230sqft
10,890Sqft

315 Pleasant Street
South Chatham, Massachusetts 02659

Kathy A Doyle
Gibson Sotheby's International Realty
Escape to a luxurious single-family home, close proximity to the ocean at Pleasant St. Beach, where water views greet you from main bedroom balcony and the front yard. This coastal retreat boasts an open floor plan, three generously sized bedrooms, perfect for families or small groups seeking comfort and relaxation.
$3,250,000
7bd
3ba
2460sqft
21,344Sqft

30 Mill Hill Lane
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
Rare and unique opportunity to own a classic Cape Cod compound in Chatham's iconic Old Village. Tucked at the end of a quiet lane just moments to town, lighthouse and beach. This hide-a-away compound built in 1840 consists of a four bedroom main house, three bedroom guest cottage and a small carriage house currently used as a workshop with a lively history as a neighborhood entertainment venue.
$2,499,000
107,158Sqft

0 Crows Pond Road
Chatham, Massachusetts 02633

Jen A Pappalardo
Christie's International Real Estate Atlantic Brokerage
2.46 acre waterfront lot in Chatham with 220 feet of frontage directly on salt water Crow's Pond. Land is set on a bluff and has direct water access to Ryders Cove, Pleasant Bay, Chatham Harbor and the Atlantic Ocean. Near Eastward Ho! Country Club. Paved driveway has been installed and there is town water already on the property. Custom build the home of your dreams.
$7,495,000
5bd
6ba
6128sqft
20,473Sqft

30 Fairway Drive
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
This architectural masterpiece perched above Chatham Seaside Links in a highly coveted Village enclave offers an incredible array of breathtaking vistas with easterly views of Chatham Harbor. The five bedroom home embodies elegant coastal style with showpiece finishes, custom detailing and countless amenities.
$1,995,000
3bd
4ba
2884sqft
11,326Sqft

53 Ocean Port Lane
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
South of 28 and situated on a quiet sandy lane in West Chatham, this home is the perfect beach house just a short distance to both Barn Hill Landing and Hardings Beach. Recently renovated, the home exudes coastal style living and offers superbly designed indoor and outdoor spaces.
$1,469,000
5bd
6ba
11000sqft
119,354Sqft

558 Fox Hill Road
Chatham, Massachusetts 02633

John dePreaux
Corcoran Property Advisors
New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock.
$2,899,900
4235sqft
11,326Sqft

697 Main Street
Chatham, Massachusetts 02633

Doug Grattan
Christie's International Real Estate Atlantic Brokerage
This in-town property is an ideal spot for a professional office, commercial space, or retail store. It features over three finished floors and has 13 parking spaces, with additional public parking available across the street. The property was fully renovated by Rick Roy Construction in 2008, and more space was added in 2015.
$1,865,000
3bd
2ba
2844sqft
37,897Sqft

4 Nickerson Circle
South Chatham, Massachusetts 02659

Kerry C Elinskas
Coldwell Banker Realty
Retreat lot in South Chatham. Nestled off Main Street and conveniently located mid-way between Chatham Village and Harwichport with their charming shops, galleries and fabulous restaurants and it is just minutes to several Nantucket Sound beaches! This custom home has so much to offer.
$725,000
3bd
2ba
1356sqft
5,663Sqft

19 Stoughton Lane
Chatham, Massachusetts 02633

Shane K Masaschi
Kinlin Grover Compass
Welcome to 19 Stoughton Lane, Chatham, MA! Here's your chance to build the home of your dreams. Nestled south of Route 28 and just .02 miles to stunning Ridgevale Beach on Nantucket Sound, this prime location has so much potential.
$2,175,000
1bd
1ba
1479sqft
4,356Sqft

409 Main Street
Chatham, Massachusetts 02633

Rick Smith
Gibson Sotheby's International Realty
Location-Location-Location-409 Main Street in downtown Chatham offers you this very rare and desirable combination of a mixed use building with a first floor highly visible commercial space with showcase windows, maximum retail exposure and high foot traffic, as well as a fully renovated spacious apartment on the second floor in the heart of Chatham Village.
$2,175,000
1479sqft
4,356Sqft

409 Main Street
Chatham, Massachusetts 02633

Rick Smith
Gibson Sotheby's International Realty
Location-Location-Location-409 Main Street in Downtown Chatham offers you this very rare and desirable combination of a mixed use building with a first floor highly visible commercial space with showcase windows, maximum retail exposure and high foot traffic, as well as a fully renovated spacious apartment on the second floor in the heart of Chatham Village.
$4,750,000
5bd
6ba
5578sqft
90,169Sqft

67 Uncle Alberts Drive
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
This impressive home sited on 2.07 acres on a quiet cul-de-sac is just a few minutes away from restaurants, the Chatham bike path and nearby Chatham beaches. The 2014 Eastward Companies home offers a tremendous sense of living space spanning 5,578 square feet and defined by lovely grounds, water views, luxurious finishes and a sweeping open floor plan.
$6,995,000
5bd
6ba
6508sqft
43,900Sqft

16 Seapine Road
North Chatham, Massachusetts 02650

Chris Rhinesmith
Compass Massachusetts, LLC
This exceptional custom residence currently under construction is situated in a prime North Chatham location with a nearby association beach. Seamlessly blending comfort and sophistication, the home spans three levels of generous open floor plan spaces and is located on over one acre.
$1,799,000
2bd
2ba
1510sqft
12,632Sqft

450 Old Harbor Road
North Chatham, Massachusetts 02650

Barbara P Garside
Compass Massachusetts, LLC
Once in a lifetime are you fortunate enough to be presented with an opportunity to own beachfront property! Waterfront Haven with Seawall Bulkhead & Stunning Views of Chatham Harbor. Experience the potential of this unique waterfront property nestled along Chatham Harbor. This two-bedroom, two and a half bath home features a private sandy beach with panoramic views out to the Atlantic Ocean.
$2,395,000
3bd
3ba
1863sqft
6,970Sqft

16 Little Beach Road
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
Immerse yourself in the ultimate beach lifestyle. Superbly located in a highly desirable Lighthouse Beach neighborhood, this luxurious beach house built in 2018 was extensively refreshed in 2023 with all new bathrooms, appliances, light and plumbing fixtures, smart technology and exterior curb appeal. The interiors are both elegant and playful offering a timeless coastal character.
$4,495,000
4bd
5ba
4908sqft
16,988Sqft

45 Meadow View Road S
Chatham, Massachusetts 02633

The Bohman Hartung Group
Gibson Sotheby's International Realty
Deeded rights to a boat slip in the Oyster River Hills Association's private neighborhood marina are just steps away. Custom builder Sears Point Residential has begun constructing a stunning new 4 bedroom, 6 bath, 4,908 sf classic Cape. Move in for the summer of 2025.
$2,195,000
4bd
3ba
3899sqft
21,307Sqft

174 Seapine Road
Chatham, Massachusetts 02633

Judith L Smith
John C Ricotta & Assoc.
Don't miss this fabulous home which is part of Harbor Coves Assoc. with association rights to Crows Pond a saltwater pond leading out to Bassing Harbor, Ryder's Cove, Pleasant Bay, Chatham Harbor and the Atlantic. Assoc. beach and mooring field just down the street This 4 bedroom 3 and 1/2 bath home has plenty of extra space for family and friends.
$4,695,000
3bd
3ba
2418sqft
44,394Sqft

30 Indian Trail
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
Nestled in Hardings Beach Hills, Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, presents a stunning display of nature with its panoramic marsh and creek views. The architecture of this residence is a masterful fusion of classic Cape vernacular with modern inspiration, reflective of PSD's signature style.
$1,750,000
5Room(s)
1ba
2586sqft
21,780Sqft

231 Crowell Road
Chatham, Massachusetts 02633

Judith L Smith
John C Ricotta & Assoc.
Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport .
$1,750,000
2586sqft
21,780Sqft

231 Crowell Road
Chatham, Massachusetts 02633

Judith L Smith
John C Ricotta & Assoc.
Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport.
$1,595,000
4bd
3ba
2062sqft
20,473Sqft

54 Rowland Drive
North Chatham, Massachusetts 02650

Barbara P Garside
Compass Massachusetts, LLC
Discover coastal charm and scenic views of Ryder's Cove from this spacious 4-bedroom, 3.5-bathroom home nestled in North Chatham. Deeded rights to the water, provide direct access for boating and water activities on this saltwater inlet leading to Pleasant Bay.Inside, hardwood floors and a spacious kitchen create a warm and inviting atmosphere.
$2,499,999
4bd
3ba
3199sqft
24,829Sqft

92 Absegami Run
Chatham, Massachusetts 02633

Doug Grattan
Christie's International Real Estate Atlantic Brokerage
Don't miss out on living in one of Chatham's most desired neighborhoods. Located in an exclusive enclave near Oyster Pond, this 4 bedroom, 3.5 bath home offers the discriminating buyer the opportunity for an exceptional residence in an area of remarkable homes. With over 3,200 s.f.
$3,499,900
3bd
3ba
3345sqft
20,038Sqft

33 Jessies Landing
Chatham, Massachusetts 02633

Doug Grattan
Christie's International Real Estate Atlantic Brokerage
A new residence is under way by Eastward Companies. This superbly designed 3,300+ sq. ft. home ticks off most boxes on everyone's wish list; spacious open floor plan, gourmet kitchen with butler's pantry, first floor master suite, and plenty of room for entertaining or hosting overnight guests.
$399,900
11,996Sqft

0 Victoria Drive
Chatham, Massachusetts 02633

Caroline M McAdams
Covell Realty Inc
Build your dream home on this beautiful lot nestled on a cul de sac in desirable Chatham. Septic design, engineering, and wind and energy plan are done. Town water, gas and electric are on the street. Seller currently has plans for a 1700 square foot, two bedroom, two and a half bath Cape with two car garage.
$14,950,000
5bd
6ba
7259sqft
94,961Sqft

301 Whidah Road
North Chatham, Massachusetts 02650

Doug Grattan
Christie's International Real Estate Atlantic Brokerage
Experience unparalleled craftsmanship in this remarkably designed contemporary home with commanding views of Pleasant Bay, Bassing Harbor, and Ryder's Cove. This oceanfront property features one of the most picturesque locations offered on the Cape with peaceful evening sunsets to lively 4th of July fireworks over Pleasant Bay.
$1,249,000
3bd
2ba
1617sqft
92,347Sqft

1174 Old Queen Anne Road
Chatham, Massachusetts 02633

Paul McCormick
Gibson Sotheby's International Realty
First time on the market! Experience coastal living surrounded by conservation areas and stunning sunsets. This remarkable Chatham year-round retreat spans 2.1 acres with views along Monomoy River. The main house features single-story living with two bedrooms, cozy living areas, bonus area and captivating outdoor garden spaces.
$1,849,000
6bd
5ba
2572sqft
26,572Sqft

72 Forest Beach Road
Chatham, Massachusetts 02633

Michael Magner
Berkshire Hathaway HomeServices Robert Paul Properties
Property consists of the main house plus 4 private suites completely renovated and offered fully furnished. Located south of Route 28 and 4/10 of a mile to Nantucket Sound, this one time motel has been meticulously renovated and is awaiting its new owner. This 6 bedroom, 5 full bath property would make the perfect compound or short term rental unicorn.
$275,000
31,167Sqft

0 George Ryder Road
Chatham, Massachusetts 02633

Shane K Masaschi
Kinlin Grover Compass
Lot has been filled in! Amazing opportunity to build your dream home in Chatham on this .72-acre, panhandle, private residential lot. Build a 3-bedroom home connected to town sewer, with approvals a 4-bedroom may be possible. Buyer's & buyer brokers verify sewer regulations with Board of Health as rules continue to change. The water, gas, electric, cable and sewer are on George Ryder Road.
$7,250,000
10bd
7ba
8000sqft
56,628Sqft

150-154 Cross Street
Chatham, Massachusetts 02633

John C Ricotta
John C Ricotta & Assoc.
Beautiful Chatham Georgian estate on 1.3 acres within walking distance to the center of town, Oyster Pond beach and all the amenities Chatham has to offer. Spectacular sunset views of the Oyster Pond, rolling lawns, bluestone patios and specimen landscaping surround this magnificent estate in the heart of downtown.
    48 Results returned.Per Page
    Property