Chatham Real Estate, Homes and Condos for sale

All Chatham homes currently listed for sale in Chatham as of 09/16/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Chatham homes for sale or other Chatham real estate, please contact us and one of our knowledgeable Chatham REALTORS® would be pleased to assist you.


Sort:
Show:
View:  
  Page 1 of 5  
 
$9,900,000
108 Shore Road, Chatham MA 02633
7
BEDS
8
BATHS
6,276
SQFT
$1,577
$/SQFT
1.62
ACRES
1920
BUILT
"Located on the Gold Coast of Chatham, you will benefit from the combination of essentially new construction with the style of a 1920's Colonial and an open concept contemporary interior. Elevated views of Chatham harbor and the Atlantic will wow your guests who will enjoy the privacy of the newly renovated 3 bedroom guest house with au pair quarters, while you escape to the seaside cabana with a good book and a bottle of wine. The residence includes 4 bedrooms, 4 full and 1 half baths, an office"
* LISTED OVER 120 DAYS 
$7,900,000
150-154 Cross Street, Chatham MA 02633
10
BEDS
10
BATHS
7,640
SQFT
$1,034
$/SQFT
1.30
ACRES
1948
BUILT
"MAGNIFICENT Georgian estate in heart of Chatham Village. Rolling lawns, specimen plantings, bluestone terraces & striking water views surround this residence, which echoes the glamour and grandeur of Newport mansions. With a brick-faced central structure flanked by two projecting wings to the north & south, the residence hosts more than 22 rooms including 10 bedrooms, 7 fireplaces, 7-1/2, 3 interior staircases & 7,500+ SF of finished living space on 4 levels. Each of 3 sections has private entri"
* LISTED OVER 120 DAYS 
$5,999,000
98,100,100 A Oyster Pond Furlong, Chatham MA 02633
9
BEDS
6
BATHS
4,774
SQFT
$1,257
$/SQFT
1.08
ACRES
1940
BUILT
"Please NO DRIVE-BYS! Fabulous family waterfront compound with 2 separate parcels. This in-town location on the Oyster Pond has over 160' of frontage and 3 homes with 2 stairways to the Oyster Pond. One parcel containing 30,720 s.f. known as 100 and 100A Oyster Pond Furlong which has a main house with 3 bedrooms 3 baths & a 2 bedroom 1 bath carriage house with a 2 car garage. The second parcel, containing 16,117 s.f. known as 98 Oyster Pond Furlong has 4 bedrooms and 2 full baths.Enjoy this wate"
$5,495,000
28 Oyster Pond Ln, Chatham MA 02633
5
BEDS
8
BATHS
6,098
SQFT
$901
$/SQFT
1.44
ACRES
2018
BUILT
"This exceptional new luxury Estate is set on 1.4 pastoral acres right in town, and includes a heated gunite pool, spa, and pool house w/kitchenette & bath. Step inside to a beautifully-crafted open floor plan and numerous fine details not found in any other home; such as a curved staircase handmade by the Amish. Abundant natural light fills the living room highlighted by a see-through stone fireplace. Adjacent Chef s kitchen and multiple dining areas are ideal for entertaining or your Thanksgi"
* LISTED OVER 120 DAYS 
$4,950,000
166 Shore Rd, Chatham MA 02633
3
BEDS
4
BATHS
1,745
SQFT
$2,837
$/SQFT
1.12
ACRES
1940
BUILT
"This classic Chatham beach front home enjoys an ideal and prestigious location at the heart of Shore Rd, and is within a few minutes walk to both central Main St., and the Chatham Bars Inn and Resort. Featuring over 120 ft of ocean frontage, this 3 bedroom, 3 full bath home home sits at the top of its private beach, and includes a hard to acquire mooring, which is located directly in front of the home. The ''SandBox'' occupies a prestigious location on billionaires row, and offers 180 degree, f"
* LISTED OVER 120 DAYS  * PRICE INCREASED - $4,200,000 TO $4,950,000 
$4,699,000
255 Seapine Rd, Chatham MA 02650
4
BEDS
5
BATHS
5,507
SQFT
$853
$/SQFT
1.29
ACRES
2000
BUILT
"Enjoy breathtaking views of Crows Pond from this impeccable & unique Timberframe home. This open-concept post & beam home has abundant natural light & water views from most of the first floor, including the first floor master suite with two walk-in closets. The family room, living room, and sitting area are situated around a spectacular 2-story stone fireplace & flow directly into the chef's kitchen with over-sized center island with separate pantry. The second floor includes 3 en-suite bedrooms"
* LISTED OVER 120 DAYS 
$4,500,000
19 Old Wharf Rd, Chatham MA 02650
4
BEDS
3
BATHS
1,820
SQFT
$2,473
$/SQFT
1.35
ACRES
1800
BUILT
"Imagine your view of Pleasant Bay, directly across from Chatham Inlet, to the Atlantic Ocean and a horizon as far as your eye can see... high enough for a fabulous view! Such is Spindrift, the perfect respite to replenish your soul, the ultimate North Chatham location, a circa 1803 Sea Captain's home overlooking spectacular Chatham Harbor. View ships from around the world sailing the Cape coastline, the Chatham fishing fleet going to sea, and pleasure boats out for a bountiful day of fishing. Wh"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $4,850,000 TO $4,500,000 
$4,249,000
34 Salt Marsh Way, Chatham MA 02650
5
BEDS
6
BATHS
7,940
SQFT
$535
$/SQFT
2.54
ACRES
2010
BUILT
"This amazing Magnificent Mid Century Modern architectural masterpiece earns A+ for superlative unsurpassed craftsmanship. Commissioned by a lifelong observer of architecture, his vision for a contemporary glass box of comfort and serenity has been realized in this transparent building. With perfect siting on private 3.57 Acres, you are enveloped in 2 environments simultaneously; as the sun travels, it shines on the wild for breakfast and the cultivated for dinner. Extraordinary landscape det"
* NEW LISTING 
$4,200,000
161 Kelley Ln, Chatham MA 02633
5
BEDS
5
BATHS
4,185
SQFT
$1,004
$/SQFT
1.25
ACRES
2004
BUILT
"Saltwater Waterfront on Chatham's Oyster Pond. This contemporary Cape offers spectacular views from every room. It includes 2 Master Suites with private baths. Located at the end of a dead end road it offers privacy. The location also offers boating interests to access Nantucket Sound while offering a protected anchorage. Very adequate space and includes Furniture subject to an exclusion list to be provided by the Seller. Extra sleeping and great Rental history."
$3,999,000
676and 684 Orleans Rd, Chatham MA 02650
6
BEDS
7
BATHS
5,230
SQFT
$765
$/SQFT
1.31
ACRES
1977
BUILT
"NORTH CHATHAM OCEANFRONT COMPOUND: Two 3 bedroom, 3 bath waterfront homes w/panoramic views and offering inviting floor plans w/separate deeds. This idyllic property provides the opportunity to own a new Dock & sea wall for boating & fishing. An in-ground swimming pool w/awning area & bunk house all situated on a 1.31 acre parcel offering limitless potential. The two homes were built in 1977 & 1900 respectively, the 1900 property has many updates & an addition. Amenities include lovely manicured"
$3,995,000
Whidah Rd, Chatham MA 02650
5
BEDS
6
BATHS
4,496
SQFT
$889
$/SQFT
1.20
ACRES
2019
BUILT
"Sears Point Residential is poised to begin construction of this 5 bedroom, 5.5 bath, 4,496 sf home on 1.2 acres with private beach ownership and commanding elevated Pleasant Bay, Outer Beach and Atlantic Ocean views from virtually every room. Each bedroom will be en-suite with master bedrooms with soaking tubs on both floors. Center stage will be a chef's kitchen with a large island, open floor-plan dining and living space with wide plank hickory floors, 9 ft ceilings and custom woodwork. Two ro"
$3,995,000
617 Fox Hill Rd, Chatham MA 02633
4
BEDS
7
BATHS
7,722
SQFT
$517
$/SQFT
0.99
ACRES
2001
BUILT
"First time offering of this exceptional, custom-designed, palatial center-hall Colonial. This waterfront estate is set water's edge on Crow's Pond, abutting the famed Eastward Ho golf-course. Built in 2001, this home offers over 7,000 square feet of meticulously planned luxury living with attention to every detail. The exterior gardens were laid out and designed by a master gardener to be an outdoor oasis. The interior space is formal and luxurious while also comfortable. The spectacular water v"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $4,250,000 TO $3,995,000 
$3,890,000
24 Andrew Mitchell Ln, Chatham MA 02650
6
BEDS
8
BATHS
5,700
SQFT
$682
$/SQFT
1.54
ACRES
2003
BUILT
"This stunning North Chatham estate was built by James Gable of Gable Building Corp. Sited on 1.54 acres of private grounds, this luxurious residence offers a stately 5,700 square foot main house, heated 2-car garage, beautifully appointed detached guest house over an additional 3-car garage, an in-ground heated pool with pool house, patio, multiple decks and deeded access to an association beach. The open concept first floor features multiple living & dining spaces, a cook's kitchen w/maple cabi"
$3,499,999
581 Shore, Chatham MA 02633
5
BEDS
7
BATHS
4,030
SQFT
$868
$/SQFT
0.50
ACRES
2018
BUILT
"A rare offering on Shore Road in Chatham. A brand new residence in one of Chatham's most desirable areas. This classic home will encompass over 4,000 sq. ft of living space and provide its owners with luxury modern conveniences including a swimming pool suitable for today's discerning buyer. This 5 bedroom, 6 bath home features an inviting open floor plan, great room, chef's kitchen with focus on a large center island, first floor master suite, and blue stone patio area ideal for outside enterta"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,999,999 TO $3,499,999 
$3,495,000
789 Fox Hill Rd, Chatham MA 02633
3
BEDS
2
BATHS
1,275
SQFT
$2,741
$/SQFT
0.47
ACRES
1950
BUILT
"Breathtaking views of Bassing Harbor, Fox's Spit, Pleasant Bay & distant views of North Beach from this gorgeous private sandy beach on Bassing Harbor with access to Crow's Pond. Quintessential Cape Cod home, built in 1950 by the founder of the Camp Avalon Girl's Sailing Camp, is sweet, charming, and beautifully maintained and is located on a well treed 1/2 Acre sloping parcel. The front to back living room with fireplace & wood floors opens to a lovely enclosed porch with walls of windows, ligh"
* LISTED OVER 120 DAYS 
$2,895,000
257 Stage Harbor, Chatham MA 02633
4
BEDS
5
BATHS
4,820
SQFT
$601
$/SQFT
0.50
ACRES
2004
BUILT
"Price Improvement!! Fabulous Chatham near town location on the Loop.Built in 2004,this striking Captains Style home with architectural detail is generously sized and features a significant gathering room with a spacious gourmet kitchen, and breakfast area.This is accentuated with a giant fireplace and access to a seasonal comfortable screened porch. There are 4 bedrooms, including a very private master bedroom suite,that includes a sizable master bath with lots of extras including a heated tile "
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,995,000 TO $2,895,000 
$2,750,000
159 Seapine Road, Chatham MA 02650
5
BEDS
4
BATHS
2,978
SQFT
$923
$/SQFT
0.84
ACRES
1951
BUILT
"Enjoy a serene waterfront setting at this expanded renovated Cape perched directly on Crow's Pond with striking views from every room. Soft sandy beachfront access is right outside your door offering boating, fishing, clamming and mooring area. Rock revetment wall already in place. This 5 bedroom, 4 bath home with inviting floor plan features a fabulous tiled sunroom, remodeled kitchen & dining area, formal living room w/ fireplace. All with panoramic views and open to the 80-ft deck to take in "
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,999,999 TO $2,750,000 
$2,575,000
26 Stage Harbor Road, Chatham MA 02633
4
BEDS
6
BATHS
4,000
SQFT
$644
$/SQFT
0.31
ACRES
2018
BUILT
"Imagine living, laughing and loving life in this stylish, and sharp, comfortable new home with deeded deep water dock and mooring rights at Oyster Pond. Open, spacious, soaring ceiling, sun drenched rooms, thoughtfully designed flow including two master suites. The second level offers even more flexible living spaces for a multi generational family to enjoy together or on their own for game time and reading. Sunny private second floor deck overlooking the park and an enormous mahogany deck just"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,795,000 TO $2,575,000 
$2,495,000
60 Tappan Dr, Chatham MA 02633
4
BEDS
5
BATHS
3,770
SQFT
$662
$/SQFT
0.53
ACRES
2014
BUILT
"Dreamy-Comfortable- Private. Imagine waking up to the gentle sea breeze and scent of the fresh salt air in this breathtaking coastal chic waterfront home. Stylishly designed offering 3 levels of distinctive living with sweeping views from every room. Soaring ceilings, masterful attention to detail & custom craftsmanship abound. The gorgeous master suite with relaxing spacious sitting room with even more views. The kids will love the playful lower level with custom ship style bunk room, bonus "
* PRICE LOWERED - $2,595,000 TO $2,495,000 
$2,495,000
107 School St, Chatham MA 02633
5
BEDS
6
BATHS
2,922
SQFT
$854
$/SQFT
0.33
ACRES
2012
BUILT
"Located in the Old Village of Chatham with a walk to town and Lighthouse Beach location and views of the Mill Pond. This ''like new'' home was built in 2012 by Polhemus, Savery, Desilva builders and it has all of the amenities one could imagine. There are 5 large bedrooms and the master is on the first floor and also there are 5 1/2 baths and a finished basement. The chef's dream kitchen with stainless appliances and granite counter tops will certainly exceed your expectations. There are wonderf"
$2,490,000
63 Cross St, Chatham MA 02633
11
BEDS
11
BATHS
5,055
SQFT
$493
$/SQFT
0.52
ACRES
1877
BUILT
"Tucked away on a quiet street in an oasis of tranquility just steps to the Village and close to Oyster Pond Children's Beach and Lighthouse Beach. Now a family residence but once a bed and breakfast known as The Cyrus Kent House. Built in 1877 for a prominent sea captain.The main house, approximately 3855 s.f. has 8 bedrooms, with 6 fireplaces, and all with en suite baths. A gracious and sun-filled living room with marble fireplace and bay window, dining room, fire-placed family room, wood-panel"
* LISTED OVER 120 DAYS 
$2,375,000
277 Woodland Way, Chatham MA 02650
4
BEDS
3
BATHS
3,299
SQFT
$720
$/SQFT
1.29
ACRES
1969
BUILT
"Perfectly nestled at the end of this sought after neighborhood sits this picturesque setting and sophisticated and stylish home. Open, bright and airy with spacious rooms all with sweeping views of Ryders Cove. This 4 bedroom home has some much to offer, privacy, comfort, great entertaining spaces, lush gardens, views, deeded beach access at Crows Pond and room for a pool. This home is ideal for multi generational families with close proximity to some of the best dining, entertainment and shoppi"
* LISTED OVER 120 DAYS 
$2,250,000
270 Stage Harbor Road, Chatham MA 02633
3
BEDS
5
BATHS
3,900
SQFT
$577
$/SQFT
0.33
ACRES
1853
BUILT
"Sophisticated Luxury Sea Captain's homestead steeped with quintessential charm and modern elegance. Located in the heart of coveted Chatham Village with easy walk to beaches, shops, restaurants, and parks. Showcased by Chatham Garden Club in 2018 for its alluring gardens, koi pond, rose covered white picket fences and ornamental trees. Also a recipient Chatham's Tricentennial Honorable Home award in 2012. Tastefully appointed guest rooms with private baths, sunroom drenched in warm natural light"
* LISTED OVER 120 DAYS 
$2,249,000
830 Fox Hill Road, Chatham MA 02650
4
BEDS
4
BATHS
3,133
SQFT
$718
$/SQFT
0.50
ACRES
1990
BUILT
"Life is bright, light, and beautiful in this magical home on Avalon Point. Its stunning renovation is hot off the presses and features an incredible chef s kitchen, luxurious marble bathrooms, fine woodwork, and sublime spaces. Elegant yet relaxed, you ll revel in its location in one of the most scenic and desirable areas of Chatham, just around the bend from the rolling greens of Eastward Ho!, the breathtaking vistas of Pleasant Bay, and picturesque boats moored in Crow s Pond (where you "
 
View:  
  Page 1 of 5  
 

Explore Chatham Communities

Choose a community below to view homes, condos and Real Estate for sale.

 Properties
are awaiting your review.  We have ALL Active Listings.  You'll receive new listing alerts and price updates ensuring you stay ahead of the market.
Your information will be kept secure and private and you can opt-out at any time.
Get Unlimited MLS Access
Automated New Listing Updates
Price Change Alerts
Join now (it's free):
Name (first/last)
 
Email Address
Member sign in:
Email Address