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
20 Hardings Beach Road Chatham, MA In a coveted Harding's Beach location, this fully renovated Chatham home offers sweeping v...	4 beds \| 4 baths \| 2,770 sq.ft.	$1,995,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 1.38% Airbnb Rental Income: $5632 Traditional Rental Income: $4925 Airbnb ROI: 1.15% Traditional ROI: 1.38%
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%
38 Indian Trail Chatham, MA BREATHTAKING SUNSETS OVER NANTUCKET SOUND. Perched above Buck's Creek with panoramic views...	4 beds \| 4 baths \| 3,878 sq.ft.	$4,750,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.1% Airbnb Rental Income: $5632 Traditional Rental Income: $6165 Airbnb ROI: -0.28% Traditional ROI: 0.1%
290 Old Comers Road Chatham, MA ''On Pink Wink Pond'' embodies the essence of Cape Cod in this remarkable estate. A startl...	4 beds \| 5 baths \| 3,603 sq.ft.	$2,750,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.43% Airbnb Rental Income: $5632 Traditional Rental Income: $6955 Airbnb ROI: 0.47% Traditional ROI: 1.43%
14 Pond View Lane Chatham, MA Sears Point Development presents another breathtaking home that could be your new year-rou...	4 beds \| 6 baths \| 4,989 sq.ft.	$5,295,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 0.67% Airbnb Rental Income: $5632 Traditional Rental Income: $8510 Airbnb ROI: -0.15% Traditional ROI: 0.67%
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: 2.68% Traditional cash on cash: 1.19% Airbnb Rental Income: $6412 Traditional Rental Income: $3224 Airbnb ROI: 2.68% Traditional ROI: 1.19%
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.	$2,200,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 0.57% Airbnb Rental Income: $6412 Traditional Rental Income: $3808 Airbnb ROI: 1.23% Traditional ROI: 0.57%
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%
6 Stephen Drive Chatham, MA Set in one of Chatham's most desirable neighborhoods, just minutes from Hardings and Ridge...	4 beds \| 5 baths \| 3,069 sq.ft.	$2,195,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 1.75% Airbnb Rental Income: $5632 Traditional Rental Income: $6099 Airbnb ROI: 0.97% Traditional ROI: 1.75%
409 Main Street Chatham, MA Location-Location-Location-409 Main Street in downtown Chatham offers you this very rare a...	1 beds \| 2 baths \| 1,479 sq.ft.	$1,995,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 0.05% Airbnb Rental Income: $3128 Traditional Rental Income: $2479 Airbnb ROI: 0.02% Traditional ROI: 0.05%
67 Uncle Alberts Drive Chatham, MA GRACIOUS LIVING ON OVER TWO ACRES NEAR CHATHAM BEACHES AND BELOVED DINING DESTINATIONS // ...	5 beds \| 8 baths \| 5,578 sq.ft.	$3,995,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 0.37% Airbnb Rental Income: $8269 Traditional Rental Income: $6708 Airbnb ROI: 0.37% Traditional ROI: 0.37%
355 Training Field Road Chatham, MA MOTIVATED SELLERS! Just 8/10 of a mile to Jackknife Point Beach, this beautifully appointe...	3 beds \| 4 baths \| 2,225 sq.ft.	$1,475,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 2.08% Airbnb Rental Income: $6412 Traditional Rental Income: $4803 Airbnb ROI: 2.34% Traditional ROI: 2.08%
558 Fox Hill Road Chatham, MA New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed ...	5 beds \| 10 baths \| 11,000 sq.ft.	$1,469,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.26% Airbnb Rental Income: $8269 Traditional Rental Income: $6840 Airbnb ROI: 1.16% Traditional ROI: 1.26%
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 \| 3 baths \| 1,850 sq.ft.	$5,900,000	Airbnb cash on cash: -1.54% Traditional cash on cash: -1.58% Airbnb Rental Income: $4814 Traditional Rental Income: $3622 Airbnb ROI: -1.54% Traditional ROI: -1.58%
106 Stage Neck Road Chatham, MA Nestled on just over an acre of meticulously landscaped grounds with a private well for ir...	4 beds \| 4 baths \| 3,834 sq.ft.	$2,500,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 0.52% Airbnb Rental Income: $5632 Traditional Rental Income: $4552 Airbnb ROI: 0.5% Traditional ROI: 0.52%
30 Indian Trail Chatham, MA Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal masterp...	3 beds \| 3 baths \| 2,418 sq.ft.	$4,395,000	Airbnb cash on cash: -0.02% Traditional cash on cash: -0.27% Airbnb Rental Income: $6412 Traditional Rental Income: $4113 Airbnb ROI: -0.02% Traditional ROI: -0.27%
45 Meadow View Road S Chatham, MA New construction and a deeded boat slip in the Oyster River Hills private neighborhood mar...	4 beds \| 6 baths \| 4,908 sq.ft.	$4,200,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 0.59% Airbnb Rental Income: $5632 Traditional Rental Income: $6677 Airbnb ROI: 0.03% Traditional ROI: 0.59%
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%
169 Shore Road Chatham, MA Steps from the iconic Chatham Bars Inn, this extraordinary coastal residence has been reen...	4 beds \| 5 baths \| 4,020 sq.ft.	$7,950,000	Airbnb cash on cash: -0.64% Traditional cash on cash: -0.65% Airbnb Rental Income: $5632 Traditional Rental Income: $4376 Airbnb ROI: -0.64% Traditional ROI: -0.65%
335 Stage Island Road Chatham, MA Family-friendly home on Chatham's private Stage Island boasts captivating barrier beach an...	4 beds \| 6 baths \| 5,372 sq.ft.	$4,750,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.5% Airbnb Rental Income: $5632 Traditional Rental Income: $8209 Airbnb ROI: -0.34% Traditional ROI: 0.5%
36 Moonbeam Lane Chatham, MA This expansive Cape with timeless curb appeal is located in an exclusive Chatham neighborh...	4 beds \| 4 baths \| 4,857 sq.ft.	$3,495,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 0.29% Airbnb Rental Income: $5632 Traditional Rental Income: $5309 Airbnb ROI: 0.04% Traditional ROI: 0.29%
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%
98 Horizon Drive Chatham, MA A new construction and a great value in Chatham with deeded rights to Lover's Lake for swi...	3 beds \| 5 baths \| 3,310 sq.ft.	$2,195,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 1.96% Airbnb Rental Income: $6412 Traditional Rental Income: $6212 Airbnb ROI: 1.44% Traditional ROI: 1.96%
13 Captain Knowles Way Chatham, MA Experience the perfect blend of luxury, privacy, and convenience in this exceptional new c...	5 beds \| 7 baths \| 5,700 sq.ft.	$6,995,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.32% Airbnb Rental Income: $8269 Traditional Rental Income: $9202 Airbnb ROI: -0.07% Traditional ROI: 0.32%
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%
85 Main Street Chatham, MA OFFERED FULLY FURNISHED INCLUDING ALL CONTENTS SO YOU CAN MOVE RIGHT IN! // Ideally situat...	3 beds \| 4 baths \| 2,998 sq.ft.	$4,400,000	Airbnb cash on cash: -0.01% Traditional cash on cash: -0.06% Airbnb Rental Income: $6412 Traditional Rental Income: $4936 Airbnb ROI: -0.01% Traditional ROI: -0.06%
144 Lakeview Avenue Chatham, MA SIGNIFICANT PRICE REDUCTION......Three bedroom ranch house in desirable Riverbay Estates. ...	3 beds \| 2 baths \| 1,726 sq.ft.	$895,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 2.53% Airbnb Rental Income: $6412 Traditional Rental Income: $3272 Airbnb ROI: 4.79% Traditional ROI: 2.53%
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.	$2,150,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 0.09% Airbnb Rental Income: $5632 Traditional Rental Income: $3107 Airbnb ROI: 0.79% Traditional ROI: 0.09%
287 Cedar Street Chatham, MA NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retre...	3 beds \| 5 baths \| 3,640 sq.ft.	$4,200,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 0.5% Airbnb Rental Income: $6412 Traditional Rental Income: $6157 Airbnb ROI: 0.24% Traditional ROI: 0.5%
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%
25 Wikis Way Chatham, MA TIMELESS COASTAL LUXURY // Prepare to be embraced by one of the most breathtaking panorama...	4 beds \| 5 baths \| 4,654 sq.ft.	$5,900,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -0.13% Airbnb Rental Income: $5632 Traditional Rental Income: $6762 Airbnb ROI: -0.55% Traditional ROI: -0.13%
55 Winterset Drive Chatham, MA Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham'...	4 beds \| 4 baths \| 4,072 sq.ft.	$2,295,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 1.33% Airbnb Rental Income: $5632 Traditional Rental Income: $5532 Airbnb ROI: 0.85% Traditional ROI: 1.33%
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%
2016 Main Street Chatham, MA Stunning Magazine-Quality Home with Resort-Style Living on Main Street Tucked privately of...	4 beds \| 5 baths \| 3,902 sq.ft.	$2,150,000	Airbnb cash on cash: 1% Traditional cash on cash: 1.77% Airbnb Rental Income: $5632 Traditional Rental Income: $6036 Airbnb ROI: 1% Traditional ROI: 1.77%
86 Champlain Road Chatham, MA Hidden gem on Chatham's historic Loop with views of Stage Harbor, the Stage Harbor Lightho...	3 beds \| 5 baths \| 4,361 sq.ft.	$3,399,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 0.44% Airbnb Rental Income: $6412 Traditional Rental Income: $5935 Airbnb ROI: 0.2% Traditional ROI: 0.44%
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%

Real Estate investment in Chatham, MA

There are 66 properties for sale in the city of Chatham . The median list price in Chatham is $2,195,000 and the average price per square foot is $722. In September 2025, the average monthly cash on cash return in Chatham is 1.00%. The average monthly rental income in Chatham is $4,376.

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

There are 66 investment properties available for sale in Chatham.

In 2025, 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 $6,412.

Your search for investment property begins and ends here

Investment Property for Sale in Chatham, MA

20 Hardings Beach Road

Chatham, MA

4 beds | 4 baths | 2,770 sq.ft.

$1,995,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $5632

Traditional Rental Income: $4925

Airbnb ROI: 1.15%

Traditional ROI: 1.38%

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%

38 Indian Trail

Chatham, MA

4 beds | 4 baths | 3,878 sq.ft.

$4,750,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $5632

Traditional Rental Income: $6165

Airbnb ROI: -0.28%

Traditional ROI: 0.1%

290 Old Comers Road

Chatham, MA

4 beds | 5 baths | 3,603 sq.ft.

$2,750,000

Airbnb cash on cash: 0.47%

Traditional cash on cash: 1.43%

Airbnb Rental Income: $5632

Traditional Rental Income: $6955

Airbnb ROI: 0.47%

Traditional ROI: 1.43%

14 Pond View Lane

Chatham, MA

4 beds | 6 baths | 4,989 sq.ft.

$5,295,000

Airbnb cash on cash: -0.15%

Traditional cash on cash: 0.67%

Airbnb Rental Income: $5632

Traditional Rental Income: $8510

Airbnb ROI: -0.15%

Traditional ROI: 0.67%

93 Orleans Road

Chatham, MA

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

$1,399,000

Airbnb cash on cash: 2.68%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $6412

Traditional Rental Income: $3224

Airbnb ROI: 2.68%

Traditional ROI: 1.19%

55 Christopher Harding Lane

Chatham, MA

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

$2,200,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $6412

Traditional Rental Income: $3808

Airbnb ROI: 1.23%

Traditional ROI: 0.57%

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%