Chatham, MA homes for sale & real estate

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NEW 1 DAY AGO3D WALKTHROUGH

ABOUT THIS HOME
Chatham, MA Homes for Sale
This house was designed and built by Grattan Gill, a Taliesin Fellow and Frank Lloyd Wright apprentice (1952-57). This distinctive South Chatham home showcases timeless architecture, thoughtful design, and modern comfort. The main level offers the convenience of first-floor living, featuring a spacious primary bedroom, a full bath and direct access to a private balcony overlooking the expansive rear deck—an ideal setting for morning coffee or evening relaxation. The walkout lower level adds exceptional versatility with a second full bathroom, a generous bonus room perfect for guests, a home office, or recreation space, along with a dedicated laundry area and abundant storage. Addition

$810,000

1 bed2 baths768 sq ft

24 Deep Water Ln, South Chatham, MA 02633

Generous bonus room • Private balcony • Walkout lower level

NEW 12 HRS AGO

ABOUT THIS HOME
Chatham, MA Homes for Sale
This multiuse property won the 2015 Preservation Award it was done with the upmost care and excellence. Calling all investors this amazing property for sale consist of 4 one bedroom apartments, 1 two bedroom apartment, and 1 commercial space. This building has been completely renovated. The building was lifted so it is structurally sound, sprinkler system in place, new furnace, new electrical panels , landscaping , parking for all residents laundry room for residents, storage units, trash removal and security system . These income properties don't come on often in Chatham with great tenants in place. One apartment is open and the commercial space new owner could use for themselves or rent.

$2,500,000

Studio— baths3,436 sq ft

2485 Main St, South Chatham, MA 02659

New furnace • Landscaping • Completely renovated

ABOUT THIS HOME
Chatham, MA Homes for Sale
SOLITUDE | A Sophisticated Chatham Antique Tucked away in one of Chatham's most coveted locations, "Solitude" offers a blend of a private tranquil setting while just moments from town, Seaside Links Golf Course, and Claflin Landing Beach. This exquisite 5-bedroom, 3.5-bath antique has been masterfully restored, with an emphasis preserving its timeless character with refined aesthetics. original glass windows, gorgeous wide pine floors, hand-finished woodwork, and four fireplaces. A stunning kitchen and beautifully appointed modern bathrooms bring effortless refined character to the home, while a subtle peek of Chatham Harbor adds to its coastal allure. Outside, private gardens and

$2,995,000

5 beds3.5 baths1,969 sq ft

156 Chatham Bars Ave, Chatham, MA 02633

Four fireplaces • Masterfully restored • 0.38 acre lot

ABOUT THIS HOME
Chatham, MA Homes for Sale
When offering please include proof of funds or pre-approval letter. Deposits may be paid via Depositlink or check payable to Compass LLC.

$1,199,000

3 beds2.5 baths1,144 sq ft

190 Heritage Ln, Chatham, MA 02633

0.24 acre lot • Garage • Built 1973

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ABOUT THIS HOME
Chatham, MA Homes for Sale
Discover coastal living in this custom-built 2015 contemporary Cape, just 3/10 mile from Forest Beach in desirable South Chatham. Approximately 2,300 sq. ft. includes 3 bedrooms (2 spacious en-suite bedrooms with walk-in closets) and 3½ baths. The open floor plan features 8-10' ceilings, abundant natural light, and white oak floors. The kitchen opens to the dining and living areas with a gas fireplace. Amenities include Anderson Stormwatch windows, gas heat, central air and underground utilities provide year-round comfort. The finished lower level offers a Jacuzzi bath, antique pine bar, and pool table. Quality construction includes double-dipped cedar shingles, Azak trim and decking

$1,795,000

3 beds3.5 baths2,331 sq ft

43 Tobey Turtle, South Chatham, MA 02659

Open floor plan • Gas fireplace • Jacuzzi bath

Property at 166 Shore Rd, Chatham, MA 02633, 4 beds, 3 baths

$8,950,000

4 beds3 baths1,738 sq ft

166 Shore Rd, Chatham, MA 02633

Property at 48 Hunter Rise, Chatham, MA 02633, 3 beds, 3 baths

$3,595,000

3 beds3 baths2,856 sq ft

48 Hunter Rise, Chatham, MA 02633

Property at 43 Tobey Turtle Rd, Chatham, MA 02633, 3 beds, 3.5 baths

$1,795,000

3 beds3.5 baths2,331 sq ft

43 Tobey Turtle Rd, Chatham, MA 02633

Property at 600 Fox Hill Rd, Chatham, MA 02633, 3 beds, 3.5 baths

$4,250,000

3 beds3.5 baths3,071 sq ft

600 Fox Hill Rd, Chatham, MA 02633

Property at 153 Shore Rd, Chatham, MA 02633, 3 beds, 2.5 baths

$9,995,000

3 beds2.5 baths3,079 sq ft

153 Shore Rd, Chatham, MA 02633

Property at 71 Rowland Dr, North Chatham, MA 02650, 2 beds, 2 baths

$1,895,000

2 beds2 baths1,398 sq ft

71 Rowland Dr, North Chatham, MA 02650

Property at 558 Fox Hill Rd, Chatham, MA 02633, 5 beds, 8 baths

$1,469,000

5 beds8 baths11,000 sq ft

558 Fox Hill Rd, Chatham, MA 02633

Property at 55 Winterset Dr, Chatham, MA 02633, 4 beds, 3.5 baths

$2,390,000

4 beds3.5 baths4,072 sq ft

55 Winterset Dr, Chatham, MA 02633

Property at 65 Captain Kendrick Dr, Chatham, MA 02633, 3 beds, 3 baths

$995,000

3 beds3 baths1,752 sq ft

65 Captain Kendrick Dr, Chatham, MA 02633

Property at 66 Ethelma Dr, Chatham, MA 02633, 4 beds, 4.5 baths

$4,500,000

4 beds4.5 baths4,689 sq ft

66 Ethelma Dr, Chatham, MA 02633

Property at 101 Morris Island Rd, Chatham, MA 02633, 4 beds, 4.5 baths

$4,995,000

4 beds4.5 baths3,225 sq ft

101 Morris Island Rd, Chatham, MA 02633

Property at 212 Orleans Rd Apt D, North Chatham, MA 02650, 2 beds, 2 baths

$689,000

2 beds2 baths1,083 sq ft

212 Orleans Rd Apt D, North Chatham, MA 02650

Property at 240 Riverview Dr, Chatham, MA 02633, 3 beds, 2 baths

$1,275,000

3 beds2 baths2,070 sq ft

240 Riverview Dr, Chatham, MA 02633

Property at 336 Stage Island Rd, Chatham, MA 02633, 3 beds, 2.5 baths

$2,850,000

3 beds2.5 baths2,205 sq ft

336 Stage Island Rd, Chatham, MA 02633

Property at 70 Uncle Deane's Rd, South Chatham, MA 02659, 3 beds, 3 baths

$1,999,000

3 beds3 baths3,514 sq ft

70 Uncle Deane's Rd, South Chatham, MA 02659

Property at 56 Stage Island Rd, Chatham, MA 02633, 4 beds, 4 baths

$5,250,000

4 beds4 baths2,932 sq ft

56 Stage Island Rd, Chatham, MA 02633

Property at 739 Main St Unit 1E, Chatham, MA 02633, 2 beds, 3.5 baths

$1,450,000

2 beds3.5 baths1,770 sq ft

739 Main St Unit 1E, Chatham, MA 02633

Property at 60 Harbor Hill Rd, Chatham, MA 02633, 4 beds, 3.5 baths

$2,950,000

4 beds3.5 baths3,978 sq ft

60 Harbor Hill Rd, Chatham, MA 02633

Property at 150-154 Cross St, Chatham, MA 02633, 10 beds, 8.5 baths

$6,500,000

10 beds8.5 baths7,658 sq ft

150-154 Cross St, Chatham, MA 02633

Property at 739 Main St #739, Chatham, MA 02633, 2 beds, 3.5 baths

$1,450,000

2 beds3.5 baths1,770 sq ft

739 Main St #739, Chatham, MA 02633

Property at 95 Cotchpinicut, Chatham, MA 02633, 4 beds, 5 baths

$5,900,000

4 beds5 baths4,394 sq ft

95 Cotchpinicut, Chatham, MA 02633

Property at 157 Bridge St, Chatham, MA 02633, 4 beds, 6 baths

$12,999,900

4 beds6 baths6,234 sq ft

157 Bridge St, Chatham, MA 02633

Property at 38 Indian Trl, Chatham, MA 02633, 4 beds, 3.5 baths

$4,295,000

4 beds3.5 baths4,967 sq ft

38 Indian Trl, Chatham, MA 02633

Property at 95 Cotchpinicut Rd, North Chatham, MA 02633, 4 beds, 5 baths

$5,900,000

4 beds5 baths4,394 sq ft

95 Cotchpinicut Rd, North Chatham, MA 02633

Property at 35 Duncan Ln, Chatham, MA 02633, 3 beds, 2 baths

$1,350,000

3 beds2 baths2,176 sq ft

35 Duncan Ln, Chatham, MA 02633

Property at 41 Court St, North Chatham, MA 02650, 3 beds, 2.5 baths

$2,295,000

3 beds2.5 baths3,504 sq ft

41 Court St, North Chatham, MA 02650

Property at 70 Judges Way, Chatham, MA 02633, 5 beds, 4.5 baths

$5,750,000

5 beds4.5 baths4,060 sq ft

70 Judges Way, Chatham, MA 02633

Property at 50 Sylvan Way, South Chatham, MA 02659, 6 beds, 7 baths

$5,900,000

6 beds7 baths6,183 sq ft

50 Sylvan Way, South Chatham, MA 02659

Property at 409 Main St, Chatham, MA 02633, 1 bed, 1.5 baths

$2,100,000

1 bed1.5 baths1,479 sq ft

409 Main St, Chatham, MA 02633

Property at 33 Duck Marsh Ln, Chatham, MA 02633, 3 beds, 2 baths

$829,000

3 beds2 baths1,192 sq ft

33 Duck Marsh Ln, Chatham, MA 02633

Property at 15 Bay Ln, Chatham, MA 02633, 4 beds, 4.5 baths

$4,950,000

4 beds4.5 baths5,110 sq ft

15 Bay Ln, Chatham, MA 02633

Property at 301 Whidah Rd, North Chatham, MA 02650, 5 beds, 6.5 baths

$12,950,000

5 beds6.5 baths7,259 sq ft

301 Whidah Rd, North Chatham, MA 02650

Property at 30 Indian Trl, Chatham, MA 02633, 3 beds, 3 baths

$4,200,000

3 beds3 baths2,418 sq ft

30 Indian Trl, Chatham, MA 02633

Property at 346 Morris Island Rd, Chatham, MA 02633, 4 beds, 3.5 baths

$4,500,000

4 beds3.5 baths2,850 sq ft

346 Morris Island Rd, Chatham, MA 02633

Property at 109 Misty Meadow Ln #4, North Chatham, MA 02650, 2 beds, 1 bath

$475,000

2 beds1 bath869 sq ft

109 Misty Meadow Ln #4, North Chatham, MA 02650

Property at 222 Barcliff, Chatham, MA 02633, 4 beds, 5.5 baths

$4,250,000

4 beds5.5 baths3,980 sq ft

222 Barcliff, Chatham, MA 02633

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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. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Redfin are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated Wed Aug 19 2026. Neither the listing broker nor Redfin shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. All properties are subject to prior sale, changes, or withdrawal. © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Average home prices near Chatham, MA

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Lower Cape homes for sale
$1,459,500

Chatham, MA real estate trends

All Home Types trends in Chatham, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,231,780

-6.3% YoY | Jun 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2026

Growth

% YoY

Chatham, MA

$1,231,780

-6.3%

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