Real Estate Investment Properties for Sale in Chatham, MA

Looking for investment property in Chatham, MA with high ROI ?

Explore a variety of short-term homes & houses in Chatham, MA. Invest wisely with VRBO & Chatham, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Chatham, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
73 Joshua Jethro Road Chatham, MA PERFECT HOUSE FOR A POOL! Located in Chatham's highly sought after Riverbay Estates commun...	3 beds \| 2 baths \| 2,307 sq.ft.	$1,520,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 1.11% Airbnb Rental Income: $2063 Traditional Rental Income: $3418 Airbnb ROI: -0.23% Traditional ROI: 1.11%
144 Barn Hill Road Chatham, MA Ideally situated in the sought-after Hardings Beach area, this home offers views of Sulphu...	3 beds \| 2 baths \| 1,536 sq.ft.	$1,250,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 1.36% Airbnb Rental Income: $2063 Traditional Rental Income: $3110 Airbnb ROI: 0.01% Traditional ROI: 1.36%
14 Pond View Lane Chatham, MA Sears Point Development presents another breathtaking home that could be your new year-rou...	4 beds \| 5 baths \| 4,989 sq.ft.	$5,295,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.67% Airbnb Rental Income: $3498 Traditional Rental Income: $8510 Airbnb ROI: -0.51% Traditional ROI: 0.67%
46 Chippingstone Rd Chatham, MA Riverbay, Chatham... True One Level living with Garage/parking on home level. 8 room custo...	3 beds \| 2 baths \| 1,713 sq.ft.	$949,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.25% Airbnb Rental Income: $2063 Traditional Rental Income: $3219 Airbnb ROI: 0.34% Traditional ROI: 2.25%
99 Uncle Alberts Drive Ext Chatham, MA Experience a rare opportunity to own a prime waterfront property in one of Chatham's most ...	2 beds \| 2 baths \| 1,850 sq.ft.	$5,495,000	Airbnb cash on cash: -2.01% Traditional cash on cash: -1.53% Airbnb Rental Income: $1648 Traditional Rental Income: $3622 Airbnb ROI: -2.01% Traditional ROI: -1.53%
287 Cedar St Chatham, MA NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retre...	3 beds \| 4 baths \| 3,640 sq.ft.	$3,850,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.64% Airbnb Rental Income: $2063 Traditional Rental Income: $6157 Airbnb ROI: -0.66% Traditional ROI: 0.64%
292 Stage Harbor Rd Chatham, MA Approximately a half mile to either Oyster Pond Beach or Stage Harbor and 3/4 of a mile to...	3 beds \| 4 baths \| 1,834 sq.ft.	$1,970,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 1.08% Airbnb Rental Income: $2063 Traditional Rental Income: $4526 Airbnb ROI: -0.55% Traditional ROI: 1.08%
86 Champlain Road Chatham, MA Hidden gem on Chatham's historic Loop with views of Stage Harbor, the Stage Harbor Lightho...	3 beds \| 4 baths \| 4,361 sq.ft.	$2,950,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.66% Airbnb Rental Income: $2063 Traditional Rental Income: $5935 Airbnb ROI: -0.95% Traditional ROI: 0.66%
24 Chickadee Circle Chatham, MA Nature-lovers! A beautifully renovated post 'n beam home perched above the Monomoy River w...	2 beds \| 2 baths \| 1,504 sq.ft.	$995,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.86% Airbnb Rental Income: $1648 Traditional Rental Income: $2989 Airbnb ROI: -0.08% Traditional ROI: 1.86%
230 Barcliff Ave Chatham, MA Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underwa...	4 beds \| 6 baths \| 5,300 sq.ft.	$4,399,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.19% Airbnb Rental Income: $3498 Traditional Rental Income: $8387 Airbnb ROI: -1.58% Traditional ROI: -0.19%
207 Horizon Drive Chatham, MA Tucked in a well-loved Chatham neighborhood, with deeded rights to Lover's Lake, this grac...	4 beds \| 4 baths \| 2,843 sq.ft.	$1,450,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 2.22% Airbnb Rental Income: $3498 Traditional Rental Income: $4849 Airbnb ROI: 0.64% Traditional ROI: 2.22%
27 Martha Kendrick Drive Chatham, MA Welcome to this delightful 3-bedroom, 2.5-bath Cape-style home nestled just moments from t...	3 beds \| 2 baths \| 2,066 sq.ft.	$1,200,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.93% Airbnb Rental Income: $2063 Traditional Rental Income: $3640 Airbnb ROI: 0.04% Traditional ROI: 1.93%
32 Sunset Lane Chatham, MA Extremely rare opportunity! Available for the first time in 60+ years, this property is tu...	3 beds \| 2 baths \| 1,626 sq.ft.	$1,850,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 0.58% Airbnb Rental Income: $2063 Traditional Rental Income: $3256 Airbnb ROI: -0.42% Traditional ROI: 0.58%
109 Misty Meadow Lane unit: Apt 4 #Apt 4 Chatham, MA Tucked away on a quiet street in the heart of North Chatham, this second-floor condominium...	2 beds \| 1 baths \| 869 sq.ft.	$475,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 3.22% Airbnb Rental Income: $1648 Traditional Rental Income: $2117 Airbnb ROI: 1.12% Traditional ROI: 3.22%
109 Misty Meadow Lane unit: Apt 2 #Apt 2 Chatham, MA Set in the desirable Misty Meadow neighborhood, 109 Misty Meadow Unit 2 offers an ideal ga...	1 beds \| 1 baths \| 696 sq.ft.	$399,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.37% Airbnb Rental Income: $1558 Traditional Rental Income: $1862 Airbnb ROI: 1.36% Traditional ROI: 3.37%
56 Skyline Drive Chatham, MA Enjoy breezy summer days and lots of lake time from this updated 4 Bedroom home located on...	4 beds \| 2 baths \| 2,392 sq.ft.	$1,599,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 1.19% Airbnb Rental Income: $3498 Traditional Rental Income: $3630 Airbnb ROI: 0.58% Traditional ROI: 1.19%
425 Main Street unit: D #D Chatham, MA Nestled above Bumbula ''It's All About Me,'' Unit D at 425 Main Street offers an exception...	1 beds \| 1 baths \| 578 sq.ft.	$495,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 2.41% Airbnb Rental Income: $1558 Traditional Rental Income: $1812 Airbnb ROI: 0.89% Traditional ROI: 2.41%
28 Lakeview Ave Chatham, MA Welcome to 28 Lakeview Ave...a Riverbay gem in a natural setting. Beautifully renovated wi...	3 beds \| 2 baths \| 2,441 sq.ft.	$1,495,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 1.09% Airbnb Rental Income: $2063 Traditional Rental Income: $3352 Airbnb ROI: -0.2% Traditional ROI: 1.09%
33 Duck Marsh Ln Chatham, MA Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this h...	3 beds \| 2 baths \| 1,192 sq.ft.	$842,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 2.25% Airbnb Rental Income: $2063 Traditional Rental Income: $2852 Airbnb ROI: 0.57% Traditional ROI: 2.25%
5 Ridge Cove Lane unit: 5 #5 Chatham, MA Welcome to this meticulously maintained, light drenched townhome. Open great room, dining ...	2 beds \| 2 baths \| 2,295 sq.ft.	$1,295,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 1.14% Airbnb Rental Income: $1648 Traditional Rental Income: $2956 Airbnb ROI: -0.34% Traditional ROI: 1.14%
121 Queen Anne Road Chatham, MA Set in one of Chatham's most coveted in-town locations, this refined coastal residence off...	4 beds \| 6 baths \| 3,702 sq.ft.	$5,400,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.45% Airbnb Rental Income: $3498 Traditional Rental Income: $8649 Airbnb ROI: -0.73% Traditional ROI: 0.45%

Real Estate investment in Chatham, MA

There are 22 properties for sale in the city of Chatham . The median list price in Chatham is $1,520,000 and the average price per square foot is $642. In February 2026, the average monthly cash on cash return in Chatham is 1.00%. The average monthly rental income in Chatham is $3,511.

Chatham, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 22 investment properties available for sale in Chatham.

In 2026, the best neighborhood to buy investment property is Chatham.

The ROI for Short-Term is higher than the Long-Term in Chatham with average rental income of $2,063.

Your search for investment property begins and ends here

Investment Property for Sale in Chatham, MA

73 Joshua Jethro Road

Chatham, MA

3 beds | 2 baths | 2,307 sq.ft.

$1,520,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $2063

Traditional Rental Income: $3418

Airbnb ROI: -0.23%

Traditional ROI: 1.11%

144 Barn Hill Road

Chatham, MA

3 beds | 2 baths | 1,536 sq.ft.

$1,250,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 1.36%

Airbnb Rental Income: $2063

Traditional Rental Income: $3110

Airbnb ROI: 0.01%

Traditional ROI: 1.36%

14 Pond View Lane

Chatham, MA

4 beds | 5 baths | 4,989 sq.ft.

$5,295,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 0.67%

Airbnb Rental Income: $3498

Traditional Rental Income: $8510

Airbnb ROI: -0.51%

Traditional ROI: 0.67%

46 Chippingstone Rd

Chatham, MA

3 beds | 2 baths | 1,713 sq.ft.

$949,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $2063

Traditional Rental Income: $3219

Airbnb ROI: 0.34%

Traditional ROI: 2.25%

99 Uncle Alberts Drive Ext

Chatham, MA

2 beds | 2 baths | 1,850 sq.ft.

$5,495,000

Airbnb cash on cash: -2.01%

Traditional cash on cash: -1.53%

Airbnb Rental Income: $1648

Traditional Rental Income: $3622

Airbnb ROI: -2.01%

Traditional ROI: -1.53%

287 Cedar St

Chatham, MA

3 beds | 4 baths | 3,640 sq.ft.

$3,850,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 0.64%

Airbnb Rental Income: $2063

Traditional Rental Income: $6157

Airbnb ROI: -0.66%

Traditional ROI: 0.64%

292 Stage Harbor Rd

Chatham, MA

3 beds | 4 baths | 1,834 sq.ft.

$1,970,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $2063

Traditional Rental Income: $4526

Airbnb ROI: -0.55%

Traditional ROI: 1.08%

86 Champlain Road

Chatham, MA

3 beds | 4 baths | 4,361 sq.ft.

$2,950,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $2063

Traditional Rental Income: $5935

Airbnb ROI: -0.95%