Real Estate Investment Properties for Sale in South Chatham, MA

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

Explore a variety of short-term homes & houses in South Chatham, MA. Invest wisely with VRBO & South 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 South Chatham, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2550 Main Street South Chatham, MA One of two new Eastward Company homes being constructed in this private enclave in Chatham...	3 beds \| 4 baths \| 4,393 sq.ft.	$3,999,900	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.3% Airbnb Rental Income: $2131 Traditional Rental Income: $2970 Airbnb ROI: -0.68% Traditional ROI: -0.3%
2548 Main Street South Chatham, MA One of two new Eastward Company homes being constructed in this private enclave in Chatham...	4 beds \| 6 baths \| 3,713 sq.ft.	$3,999,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 1.19% Airbnb Rental Income: $3585 Traditional Rental Income: $8313 Airbnb ROI: -0.29% Traditional ROI: 1.19%
22 Pine Knoll Avenue South Chatham, MA First time offered for sale in over 50 years! Welcome to this charming 3 bedroom 1 bath qu...	3 beds \| N/A baths \| 532 sq.ft.	$549,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 2.48% Airbnb Rental Income: $2131 Traditional Rental Income: $2044 Airbnb ROI: 1.59% Traditional ROI: 2.48%
132 Stage Coach Drive South Chatham, MA This well-maintained 2-bedroom, 2-bath home in South Chatham, MA offers a rare combination...	2 beds \| 2 baths \| 1,372 sq.ft.	$749,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 2.3% Airbnb Rental Income: $2719 Traditional Rental Income: $2593 Airbnb ROI: 1.56% Traditional ROI: 2.3%
Investment Properties for Sale in Other Cities of Massachusetts
671-673 Boylston St #2 Boston , MA 671-673 Boylston St #2, Boston, MA 02116 \| Condo/Coop	1 beds \| 2 baths \| 1,867 sq.ft.	$2,250,000	Airbnb cash on cash: -2.19% Traditional cash on cash: -1.59% Airbnb Rental Income: $1893 Traditional Rental Income: $2639 Airbnb ROI: -2.19% Traditional ROI: -1.59%
11 Robinwood Ave Boston , MA Right in the heart of Jamaica Plain, just steps from Jamaica Pond and the vibrant shops & ...	5 beds \| 4 baths \| 3,390 sq.ft.	$2,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $4593 Airbnb ROI: N/A Traditional ROI: 0.27%
1 Nassau St #2207 Boston , MA 1 Nassau St #2207, Boston, MA 02111 \| Condo/Coop	2 beds \| 2 baths \| 1,448 sq.ft.	$975,000	Airbnb cash on cash: -3.06% Traditional cash on cash: -2.84% Airbnb Rental Income: $3572 Traditional Rental Income: $2990 Airbnb ROI: -3.06% Traditional ROI: -2.84%
1 Franklin St #1205 Boston , MA Move in and see why Millennium Tower Boston is the evolution of luxury residential living!...	2 beds \| 2 baths \| 1,161 sq.ft.	$1,700,000	Airbnb cash on cash: -2.14% Traditional cash on cash: 0.15% Airbnb Rental Income: $2541 Traditional Rental Income: $5552 Airbnb ROI: -2.14% Traditional ROI: 0.15%
65 Victoria Heights Rd #65 Boston , MA 65 Victoria Heights Rd #65, Boston, MA 02136 \| Townhouse	3 beds \| 2 baths \| 1,793 sq.ft.	$425,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 4.11% Airbnb Rental Income: $3257 Traditional Rental Income: $3279 Airbnb ROI: 2.21% Traditional ROI: 4.11%
496 Shore Road unit: 21 #21 Truro , MA The Captains Quarters, is the most sought after '' YEAR ROUND'', rental and investment pro...	3 beds \| 2 baths \| 2,018 sq.ft.	$1,299,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.78% Airbnb Rental Income: $2850 Traditional Rental Income: $3609 Airbnb ROI: -0.4% Traditional ROI: 0.78%
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%
1 Franklin St Ph 4E Boston , MA 1 Franklin St Ph 4E, Boston, MA 02110 \| Condo/Coop	3 beds \| 4 baths \| 3,435 sq.ft.	$7,495,000	Airbnb cash on cash: -2.98% Traditional cash on cash: -2.56% Airbnb Rental Income: $3038 Traditional Rental Income: $5277 Airbnb ROI: -2.98% Traditional ROI: -2.56%
27 Quaker Lane Harwich , MA This Harwich home is set in the perfect location! Ideally situated near popular restaurant...	2 beds \| 1 baths \| 1,019 sq.ft.	$549,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 2.88% Airbnb Rental Income: $2729 Traditional Rental Income: $2298 Airbnb ROI: 2.46% Traditional ROI: 2.88%
14 Colonial Road Webster , MA 14 Colonial Drive in Webster is a must see! Located in a sought-after Webster Lake neighbo...	3 beds \| 2 baths \| 1,248 sq.ft.	$399,900	Airbnb cash on cash: 3.39% Traditional cash on cash: 5.76% Airbnb Rental Income: $2687 Traditional Rental Income: $2938 Airbnb ROI: 3.39% Traditional ROI: 5.76%
1203 Bennington St Winthrop , MA 1203 Bennington St, Winthrop, MA 02128 \| Single Family Residential	5 beds \| 3 baths \| 1,568 sq.ft.	$793,721	Airbnb cash on cash: 1.21% Traditional cash on cash: 3.28% Airbnb Rental Income: $3388 Traditional Rental Income: $4159 Airbnb ROI: 1.21% Traditional ROI: 3.28%
118 Driftwood Lane South Yarmouth , MA Cape Cod Luxury Waterfront Living on Follins Pond~Bass River! Imagine waking up to blue sk...	4 beds \| 4 baths \| 3,978 sq.ft.	$3,374,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.71% Airbnb Rental Income: $2197 Traditional Rental Income: $7060 Airbnb ROI: -1.02% Traditional ROI: 0.71%
200 Cove Way unit: 614 #614 Quincy , MA Are you an outdoors type that enjoys sailing, swimming, tennis or do you like dining out, ...	2 beds \| 2 baths \| 1,051 sq.ft.	$415,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 2.25% Airbnb Rental Income: $1458 Traditional Rental Income: $2449 Airbnb ROI: -1.41% Traditional ROI: 2.25%

Real Estate investment in South-chatham, MA

There are 4 properties for sale in the city of South Chatham . The median list price in South Chatham is $2,374,450 and the average price per square foot is $949. In February 2026, the average monthly cash on cash return in South Chatham is 2.00%. The average monthly rental income in South Chatham is $2,782.

South-chatham, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 4 investment properties available for sale in South-chatham.

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

The ROI for Long-Term is higher than the Short-Term in South-chatham with average rental income of $2,782.

Your search for investment property begins and ends here

Investment Property for Sale in South Chatham, MA

2550 Main Street

South Chatham, MA

3 beds | 4 baths | 4,393 sq.ft.

$3,999,900

Airbnb cash on cash: -0.68%

Traditional cash on cash: -0.3%

Airbnb Rental Income: $2131

Traditional Rental Income: $2970

Airbnb ROI: -0.68%

Traditional ROI: -0.3%

2548 Main Street

South Chatham, MA

4 beds | 6 baths | 3,713 sq.ft.

$3,999,900

Airbnb cash on cash: -0.29%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $3585

Traditional Rental Income: $8313

Airbnb ROI: -0.29%

Traditional ROI: 1.19%

22 Pine Knoll Avenue

South Chatham, MA

3 beds | N/A baths | 532 sq.ft.

$549,000

Airbnb cash on cash: 1.59%

Traditional cash on cash: 2.48%

Airbnb Rental Income: $2131

Traditional Rental Income: $2044

Airbnb ROI: 1.59%

Traditional ROI: 2.48%

132 Stage Coach Drive

South Chatham, MA

2 beds | 2 baths | 1,372 sq.ft.

$749,000

Airbnb cash on cash: 1.56%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $2719

Traditional Rental Income: $2593

Airbnb ROI: 1.56%

Traditional ROI: 2.3%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

1 beds | 2 baths | 1,867 sq.ft.

$2,250,000

Airbnb cash on cash: -2.19%

Traditional cash on cash: -1.59%

Airbnb Rental Income: $1893

Traditional Rental Income: $2639

Airbnb ROI: -2.19%

Traditional ROI: -1.59%

Boston , MA

5 beds | 4 baths | 3,390 sq.ft.

$2,399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.27%

Airbnb Rental Income: $null

Traditional Rental Income: $4593

Airbnb ROI: N/A

Traditional ROI: 0.27%

Boston , MA

2 beds | 2 baths | 1,448 sq.ft.

$975,000

Airbnb cash on cash: -3.06%

Traditional cash on cash: -2.84%

Airbnb Rental Income: $3572

Traditional Rental Income: $2990

Airbnb ROI: -3.06%

Traditional ROI: -2.84%

Boston , MA

2 beds | 2 baths | 1,161 sq.ft.

$1,700,000

Airbnb cash on cash: -2.14%

Traditional cash on cash: 0.15%

Airbnb Rental Income: $2541

Traditional Rental Income: $5552

Airbnb ROI: -2.14%

Traditional ROI: 0.15%

Boston , MA

3 beds | 2 baths | 1,793 sq.ft.