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

separator

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%
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.	$1,359,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.26% Airbnb Rental Income: $2063 Traditional Rental Income: $3224 Airbnb ROI: -0.08% Traditional ROI: 1.26%
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: -0.69% Traditional cash on cash: 0.05% Airbnb Rental Income: $1558 Traditional Rental Income: $2479 Airbnb ROI: -0.69% Traditional ROI: 0.05%
46 Chippingstone Road 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.	$979,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 2.15% Airbnb Rental Income: $2063 Traditional Rental Income: $3219 Airbnb ROI: 0.3% Traditional ROI: 2.15%
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.	$5,900,000	Airbnb cash on cash: -2.03% Traditional cash on cash: -1.58% Airbnb Rental Income: $1648 Traditional Rental Income: $3622 Airbnb ROI: -2.03% Traditional ROI: -1.58%
346 Morris Island Road Chatham, MA Views, Views, Views!! Sun splashed Stage Harbor waterfront offering and ever-changing vist...	4 beds \| 4 baths \| 2,850 sq.ft.	$4,900,000	Airbnb cash on cash: -0.69% Traditional cash on cash: -0.23% Airbnb Rental Income: $3498 Traditional Rental Income: $4824 Airbnb ROI: -0.69% Traditional ROI: -0.23%
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: 0.01% Traditional cash on cash: 2.09% Airbnb Rental Income: $2063 Traditional Rental Income: $3846 Airbnb ROI: 0.01% Traditional ROI: 2.09%
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: -0.55% Traditional cash on cash: 0.25% Airbnb Rental Income: $3498 Traditional Rental Income: $5309 Airbnb ROI: -0.55% Traditional ROI: 0.25%
98 Horizon Drive Chatham, MA Ready to move-in! New construction and a great value in Chatham with deeded rights to Love...	3 beds \| 4 baths \| 3,310 sq.ft.	$2,195,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 1.96% Airbnb Rental Income: $2063 Traditional Rental Income: $6212 Airbnb ROI: -0.34% Traditional ROI: 1.96%
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: -0.1% Traditional cash on cash: 0.09% Airbnb Rental Income: $3498 Traditional Rental Income: $3107 Airbnb ROI: -0.1% 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 \| 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 Road 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%
92 Barcliff Avenue Chatham, MA Honored with the prestigious 2004 Chatham Preservation Award, this iconic historical resid...	5 beds \| N/A baths \| 2,659 sq.ft.	$3,500,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.28% Airbnb Rental Income: $5760 Traditional Rental Income: $4964 Airbnb ROI: 0.17% Traditional ROI: 0.28%
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%
30 Tisquantum Road Chatham, MA What. A. View! 180 degree panoramic water vistas over The Atlantic Ocean, Chatham Harbor, ...	5 beds \| 4 baths \| 4,305 sq.ft.	$7,999,000	Airbnb cash on cash: -0.59% Traditional cash on cash: -0.31% Airbnb Rental Income: $5760 Traditional Rental Income: $6683 Airbnb ROI: -0.59% Traditional ROI: -0.31%
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%
127 Wapoos Trail Chatham, MA Tucked within the exclusive & secluded enclave of Morris Island, this one-of-a-kind water ...	5 beds \| 4 baths \| 4,307 sq.ft.	$8,250,000	Airbnb cash on cash: -0.71% Traditional cash on cash: -0.5% Airbnb Rental Income: $5760 Traditional Rental Income: $6242 Airbnb ROI: -0.71% Traditional ROI: -0.5%
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.	$1,450,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 1.64% Airbnb Rental Income: $3498 Traditional Rental Income: $4017 Airbnb ROI: 0.68% Traditional ROI: 1.64%
200 Hardings Beach Road Chatham, MA Located just a short stroll to Hardings Beach and close to many favorite local restaurants...	4 beds \| 2 baths \| 1,820 sq.ft.	$1,495,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 1.2% Airbnb Rental Income: $3498 Traditional Rental Income: $3563 Airbnb ROI: 0.6% Traditional ROI: 1.2%
230 Barcliff Avenue Chatham, MA Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underwa...	4 beds \| 6 baths \| 5,800 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%
291 Ridgevale Road Chatham, MA Idyllic Seaside Cottage is just steps to popular Ridgevale Beach! Enchantment begins with ...	3 beds \| 2 baths \| 1,424 sq.ft.	$1,495,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 0.74% Airbnb Rental Income: $2063 Traditional Rental Income: $2804 Airbnb ROI: -0.18% Traditional ROI: 0.74%
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%
40 Youngs Farm Lane Chatham, MA Tucked away next to a coastal inlet that ebbs and flows with the tide, this remarkable hom...	4 beds \| 4 baths \| 4,797 sq.ft.	$3,495,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.43% Airbnb Rental Income: $3498 Traditional Rental Income: $5428 Airbnb ROI: -0.4% Traditional ROI: 0.43%
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%
558 Riverview Drive Chatham, MA Located in Chatham's desirable Riverbay, this two bedroom, two bath, 2,097 sq. ft. residen...	2 beds \| 2 baths \| 2,097 sq.ft.	$895,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 2.17% Airbnb Rental Income: $1648 Traditional Rental Income: $2986 Airbnb ROI: 0.01% Traditional ROI: 2.17%
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: 0.92% Traditional cash on cash: 2.44% Airbnb Rental Income: $1558 Traditional Rental Income: $1812 Airbnb ROI: 0.92% Traditional ROI: 2.44%
450 Main Street Chatham, MA Welcome to 450 Main Street! A premier mixed-use investment opportunity in the heart of Cha...	5 beds \| N/A baths \| 7,396 sq.ft.	$3,500,000	Airbnb cash on cash: 0.17% Traditional cash on cash: -0.22% Airbnb Rental Income: $5760 Traditional Rental Income: $3315 Airbnb ROI: 0.17% Traditional ROI: -0.22%
93 Bucks Creek Road Chatham, MA Welcome to 93 Bucks Creek Rd, where luxury meets coastal elegance. This architecturally st...	3 beds \| 4 baths \| 3,544 sq.ft.	$3,200,000	Airbnb cash on cash: -0.72% Traditional cash on cash: -0.23% Airbnb Rental Income: $2063 Traditional Rental Income: $2986 Airbnb ROI: -0.72% Traditional ROI: -0.23%
29 Jessies Landing Chatham, MA A new luxury residence is currently under construction by Eastward Companies in Chatham. L...	3 beds \| N/A baths \| 4,565 sq.ft.	$3,499,900	Airbnb cash on cash: -0.62% Traditional cash on cash: -0.12% Airbnb Rental Income: $2063 Traditional Rental Income: $3128 Airbnb ROI: -0.62% Traditional ROI: -0.12%
28 Lakeview Avenue 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.	$1,525,000	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%
404 Stage Harbor Road Chatham, MA This stunning cedar-shingled, four-bedroom residence is just a short stroll from beautiful...	4 beds \| 4 baths \| 2,905 sq.ft.	$2,995,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 0.57% Airbnb Rental Income: $3498 Traditional Rental Income: $5131 Airbnb ROI: -0.3% Traditional ROI: 0.57%
33 Duck Marsh Lane 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%

Real Estate investment in Chatham, MA

There are 38 properties for sale in the city of Chatham . The median list price in Chatham is $1,910,000 and the average price per square foot is $698. In December 2025, the average monthly cash on cash return in Chatham is 1.00%. The average monthly rental income in Chatham is $3,512.

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

There are 38 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 $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%

93 Orleans Road

Chatham, MA

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

$1,359,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $2063

Traditional Rental Income: $3224

Airbnb ROI: -0.08%

Traditional ROI: 1.26%

409 Main Street

Chatham, MA

1 beds | 2 baths | 1,479 sq.ft.

$1,995,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 0.05%

Airbnb Rental Income: $1558

Traditional Rental Income: $2479

Airbnb ROI: -0.69%

Traditional ROI: 0.05%

46 Chippingstone Road

Chatham, MA

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

$979,000

Airbnb cash on cash: 0.3%

Traditional cash on cash: 2.15%

Airbnb Rental Income: $2063

Traditional Rental Income: $3219

Airbnb ROI: 0.3%

Traditional ROI: 2.15%

99 Uncle Alberts Drive Ext

Chatham, MA

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

$5,900,000

Airbnb cash on cash: -2.03%

Traditional cash on cash: -1.58%

Airbnb Rental Income: $1648

Traditional Rental Income: $3622

Airbnb ROI: -2.03%

Traditional ROI: -1.58%

346 Morris Island Road

Chatham, MA

4 beds | 4 baths | 2,850 sq.ft.

$4,900,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: -0.23%

Airbnb Rental Income: $3498

Traditional Rental Income: $4824

Airbnb ROI: -0.69%