Airbnb Properties for Sale in Chatham, MA

Looking for a vacation rental investment in Chatham, MA with high ROI ?

Explore a range of newly added short-term rental homes in Chatham, MA. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chatham, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
73 Joshua Jethro Road Chatham, MA Located in Chatham's highly sought after Riverbay Estates community, this 3-bedroom, 2-bat...	3 beds \| 2 baths \| 2,307 sq.ft.	$1,570,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.04% Airbnb Rental Income: $6412 Traditional Rental Income: $3418 Airbnb ROI: 2.24% Traditional ROI: 1.04%
74 Deering Drive Chatham, MA Walk to the beach! Enjoy Ridgevale Beach and warm water swimming in Nantucket Sound from t...	3 beds \| 4 baths \| 3,057 sq.ft.	$1,795,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 1.71% Airbnb Rental Income: $6412 Traditional Rental Income: $4959 Airbnb ROI: 1.82% Traditional ROI: 1.71%
93 Orleans Road Chatham, MA Welcome to the meticulous and delightful 93 Orleans Road Chatham. Enter onto the beautiful...	3 beds \| 2 baths \| 1,702 sq.ft.	$1,399,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 1.2% Airbnb Rental Income: $6412 Traditional Rental Income: $3224 Airbnb ROI: 2.69% Traditional ROI: 1.2%
55 Christopher Harding Lane Chatham, MA Step into coastal elegance in this light-filled home, perfectly nestled in a peaceful neig...	3 beds \| 3 baths \| 2,510 sq.ft.	$2,299,999	Airbnb cash on cash: 1.13% Traditional cash on cash: 0.5% Airbnb Rental Income: $6412 Traditional Rental Income: $3808 Airbnb ROI: 1.13% Traditional ROI: 0.5%
32 Gladen Lane Chatham, MA Effortlessly blending Cape Cod charm with bohemian chic flair, this 3BR 2.5 bath Cape is a...	3 beds \| 3 baths \| 1,999 sq.ft.	$2,449,000	Airbnb cash on cash: 1% Traditional cash on cash: 0.36% Airbnb Rental Income: $6412 Traditional Rental Income: $3680 Airbnb ROI: 1% Traditional ROI: 0.36%
19 Stoughton Lane Chatham, MA Here is your chance to own a slice of seaside Chatham! This prime location is only a short...	3 beds \| 2 baths \| 1,356 sq.ft.	$600,000	Airbnb cash on cash: 7.71% Traditional cash on cash: 4.07% Airbnb Rental Income: $6412 Traditional Rental Income: $3114 Airbnb ROI: 7.71% Traditional ROI: 4.07%
319 Riverview Drive Chatham, MA Sited on nearly an acre of land in Riverbay Estates, this spacious 3 bedroom, 3 bath home ...	3 beds \| 3 baths \| 2,202 sq.ft.	$1,195,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.09% Airbnb Rental Income: $6412 Traditional Rental Income: $3846 Airbnb ROI: 3.27% Traditional ROI: 2.09%
116 Happy Valley Road Chatham, MA Located off a private way to Ridgevale Beach overlooking a majestic cranberry bog sits thi...	2 beds \| 3 baths \| 1,861 sq.ft.	$1,399,500	Airbnb cash on cash: 1.62% Traditional cash on cash: 1.06% Airbnb Rental Income: $4814 Traditional Rental Income: $3101 Airbnb ROI: 1.62% Traditional ROI: 1.06%
109-4 Misty Meadow Ln Chatham, MA Tucked away on a quiet street in the heart of North Chatham, this charming second-floor co...	2 beds \| 1 baths \| 869 sq.ft.	$475,000	Airbnb cash on cash: 6.14% Traditional cash on cash: 2.23% Airbnb Rental Income: $4814 Traditional Rental Income: $2086 Airbnb ROI: 6.14% Traditional ROI: 2.23%
109-2 Misty Meadow Ln 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: 3.77% Traditional cash on cash: 2.31% Airbnb Rental Income: $3128 Traditional Rental Income: $1874 Airbnb ROI: 3.77% Traditional ROI: 2.31%
9 Bettys Path Chatham, MA Welcome to 9 Bettys Path, your private hideaway w/panoramic views of nature's finest artwo...	3 beds \| 2 baths \| 2,008 sq.ft.	$1,700,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 1.02% Airbnb Rental Income: $6412 Traditional Rental Income: $3663 Airbnb ROI: 1.97% Traditional ROI: 1.02%
68 Chippingstone Road Chatham, MA Welcome to Riverbay Estates, where year-round living meets the perfect Cape Cod escape! Th...	4 beds \| 3 baths \| 2,391 sq.ft.	$1,400,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 1.97% Airbnb Rental Income: $5632 Traditional Rental Income: $4356 Airbnb ROI: 2.08% Traditional ROI: 1.97%
235 Training Field Road Chatham, MA NEED AN IN-LAW APARTMENT? Tucked away from the road in desirable Riverbay, this comfortabl...	4 beds \| 3 baths \| 1,990 sq.ft.	$1,750,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 1.12% Airbnb Rental Income: $5632 Traditional Rental Income: $3799 Airbnb ROI: 1.55% Traditional ROI: 1.12%
144 Lakeview Avenue Chatham, MA Three bedroom ranch house in desirable Riverbay Estates. All bedrooms on first floor for e...	3 beds \| 2 baths \| 1,726 sq.ft.	$995,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 2.18% Airbnb Rental Income: $6412 Traditional Rental Income: $3272 Airbnb ROI: 4.21% Traditional ROI: 2.18%
307 Riverview Drive Chatham, MA Discover luxury and comfort in this stunning Riverbay home nestled with beautiful landscap...	3 beds \| 3 baths \| 2,340 sq.ft.	$1,575,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.22% Airbnb Rental Income: $6412 Traditional Rental Income: $3730 Airbnb ROI: 2.2% Traditional ROI: 1.22%
213 Main Street Chatham, MA Location! Location! Nestled In the heart of Chatham historic Old Village district, this 18...	4 beds \| 2 baths \| 1,238 sq.ft.	$2,300,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 0.02% Airbnb Rental Income: $5632 Traditional Rental Income: $3107 Airbnb ROI: 0.68% Traditional ROI: 0.02%
292 Stage Harbor Road Chatham, MA Approximately a half mile to either Oyster Pond Beach or Stage Harbor and 3/4 of a mile to...	3 beds \| 5 baths \| 1,834 sq.ft.	$2,150,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.91% Airbnb Rental Income: $6412 Traditional Rental Income: $4526 Airbnb ROI: 1.22% Traditional ROI: 0.91%
92 Barcliff Avenue Chatham, MA Honored with the prestigious 2004 Chatham Preservation Award, this iconic historical resid...	5 beds \| 4 baths \| 2,659 sq.ft.	$3,500,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 0.28% Airbnb Rental Income: $8269 Traditional Rental Income: $4964 Airbnb ROI: 0.81% Traditional ROI: 0.28%
51 Shattuck Place Chatham, MA This exquisitely renovated Cape is located on one of the most coveted streets in Chatham V...	3 beds \| 3 baths \| 2,133 sq.ft.	$2,395,000	Airbnb cash on cash: 1% Traditional cash on cash: 0.33% Airbnb Rental Income: $6412 Traditional Rental Income: $3669 Airbnb ROI: 1% Traditional ROI: 0.33%
7 Squanto Drive Chatham, MA This Nantucket-style home features extraordinary views across a tidal salt marsh, Oyster P...	3 beds \| 4 baths \| 3,014 sq.ft.	$3,295,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 0.38% Airbnb Rental Income: $6412 Traditional Rental Income: $4844 Airbnb ROI: 0.48% Traditional ROI: 0.38%
595 Main Street unit: 37 #37 Chatham, MA Exquisite downtown condo that combines a central location with a serene retreat. This eleg...	3 beds \| 3 baths \| 2,148 sq.ft.	$2,199,000	Airbnb cash on cash: 0.61% Traditional cash on cash: -0.06% Airbnb Rental Income: $6412 Traditional Rental Income: $3776 Airbnb ROI: 0.61% Traditional ROI: -0.06%
71 Potonumecot Road Chatham, MA Welcome to your new Chatham home! This lovely 3 bedroom, 2 bath ranch offers one-floor liv...	3 beds \| 2 baths \| 1,744 sq.ft.	$1,150,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 1.71% Airbnb Rental Income: $6412 Traditional Rental Income: $3246 Airbnb ROI: 3.49% Traditional ROI: 1.71%
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.	$1,050,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 1.72% Airbnb Rental Income: $4814 Traditional Rental Income: $2989 Airbnb ROI: 2.57% Traditional ROI: 1.72%
55 Meadowview Road S Chatham, MA Spend your days boating to Stage Harbor or Nantucket Sound from the private neighborhood m...	4 beds \| 3 baths \| 1,897 sq.ft.	$1,900,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 0.84% Airbnb Rental Income: $5632 Traditional Rental Income: $3807 Airbnb ROI: 1.23% Traditional ROI: 0.84%
80 Tisquantum Road Chatham, MA Perched on 1.68 acres high above Chatham Harbor on private Morris Island, this shingle-sty...	3 beds \| 4 baths \| 2,821 sq.ft.	$3,399,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 0.18% Airbnb Rental Income: $6412 Traditional Rental Income: $4761 Airbnb ROI: 0.31% Traditional ROI: 0.18%
67 A Leonard Way Chatham, MA Welcome to 67 A Leonard Way, a charming ranch-style 2-bedroom home tucked away on a quiet ...	2 beds \| 2 baths \| 1,340 sq.ft.	$975,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 1.79% Airbnb Rental Income: $4814 Traditional Rental Income: $2847 Airbnb ROI: 2.86% Traditional ROI: 1.79%
56 Riverview Drive Chatham, MA Located in Chatham's sought after Riverbay Estates, known for its treelined streets and co...	3 beds \| 2 baths \| 1,708 sq.ft.	$1,195,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 1.55% Airbnb Rental Income: $6412 Traditional Rental Income: $3188 Airbnb ROI: 3.32% Traditional ROI: 1.55%
1775 Main Street Chatham, MA Completed in 2023 and gently lived in-never rented-this immaculate 3-bedroom, 2-bath ranch...	3 beds \| 2 baths \| 1,775 sq.ft.	$1,299,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 1.52% Airbnb Rental Income: $6412 Traditional Rental Income: $3485 Airbnb ROI: 2.91% Traditional ROI: 1.52%
114 Bucks Creek Road Chatham, MA 'Float to the ocean with the tide'' Fish, crab kayak, paddleboard and launch off the priva...	4 beds \| 3 baths \| 2,289 sq.ft.	$1,750,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 1.19% Airbnb Rental Income: $5632 Traditional Rental Income: $4017 Airbnb ROI: 1.49% Traditional ROI: 1.19%
17 Bog Way Road Chatham, MA This contemporary home combines modern design with elevated, sweeping marsh views, just 0....	2 beds \| 1 baths \| 1,633 sq.ft.	$1,395,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 0.54% Airbnb Rental Income: $4814 Traditional Rental Income: $2370 Airbnb ROI: 1.66% Traditional ROI: 0.54%
24 Hillcrest Road Chatham, MA Located in an exclusive North Chatham neighborhood of $3M+ homes, this 5-bedroom, 3-bath r...	5 beds \| 3 baths \| 3,098 sq.ft.	$1,575,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 1.6% Airbnb Rental Income: $8269 Traditional Rental Income: $4330 Airbnb ROI: 3.22% Traditional ROI: 1.6%
56 Chatham Crest Drive Chatham, MA Experience classic Cape Cod living in this inviting 3-bedroom, 2-bath Cape, just minutes f...	3 beds \| 2 baths \| 1,729 sq.ft.	$939,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 2.24% Airbnb Rental Income: $6412 Traditional Rental Income: $3199 Airbnb ROI: 4.47% Traditional ROI: 2.24%
61 Cod Lane Chatham, MA Enjoy easy living with everything Chatham at your doorstep. In a storybook neighborhood wh...	2 beds \| 2 baths \| 1,188 sq.ft.	$849,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.11% Airbnb Rental Income: $4814 Traditional Rental Income: $2747 Airbnb ROI: 3.47% Traditional ROI: 2.11%

Vacation Rentals in Chatham

There are 33 vacation rental properties available for sale in the city of Chatham . The median list price of Airbnb properties available for sale in Chatham is $2,199,000 and the average price per square foot is $733. The cash on cash return on vacation rentals in Chatham is 1.00%. The average monthly short term rental income in Chatham is $6,412.

Chatham, MA Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 33 Airbnb properties available for sale in Chatham.

In 2025, the best neighborhood to buy short term rental property is Chatham.

In September 2025, the average Airbnb occupancy rate in Chatham is 32%.

Airbnb data on vacation rentals in Chatham, MA is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chatham, MA market insights, guest information and booking details, seasonality trends and historical Chatham, MA Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Chatham, MA

73 Joshua Jethro Road

Chatham, MA

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

$1,570,000

Airbnb cash on cash: 2.24%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $6412

Traditional Rental Income: $3418

Airbnb ROI: 2.24%

Traditional ROI: 1.04%

74 Deering Drive

Chatham, MA

3 beds | 4 baths | 3,057 sq.ft.

$1,795,000

Airbnb cash on cash: 1.82%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $6412

Traditional Rental Income: $4959

Airbnb ROI: 1.82%

Traditional ROI: 1.71%

93 Orleans Road

Chatham, MA

3 beds | 2 baths | 1,702 sq.ft.

$1,399,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $6412

Traditional Rental Income: $3224

Airbnb ROI: 2.69%

Traditional ROI: 1.2%

55 Christopher Harding Lane

Chatham, MA

3 beds | 3 baths | 2,510 sq.ft.

$2,299,999

Airbnb cash on cash: 1.13%

Traditional cash on cash: 0.5%

Airbnb Rental Income: $6412

Traditional Rental Income: $3808

Airbnb ROI: 1.13%

Traditional ROI: 0.5%

32 Gladen Lane

Chatham, MA

3 beds | 3 baths | 1,999 sq.ft.

$2,449,000

Airbnb cash on cash: 1%

Traditional cash on cash: 0.36%

Airbnb Rental Income: $6412

Traditional Rental Income: $3680

Airbnb ROI: 1%

Traditional ROI: 0.36%

19 Stoughton Lane

Chatham, MA

3 beds | 2 baths | 1,356 sq.ft.

$600,000

Airbnb cash on cash: 7.71%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $6412

Traditional Rental Income: $3114

Airbnb ROI: 7.71%

Traditional ROI: 4.07%

319 Riverview Drive

Chatham, MA

3 beds | 3 baths | 2,202 sq.ft.

$1,195,000

Airbnb cash on cash: 3.27%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $6412

Traditional Rental Income: $3846

Airbnb ROI: 3.27%

Traditional ROI: 2.09%

116 Happy Valley Road

Chatham, MA

2 beds | 3 baths | 1,861 sq.ft.

$1,399,500

Airbnb cash on cash: 1.62%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $4814

Traditional Rental Income: $3101

Airbnb ROI: 1.62%