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
58 Stepping Stones Road Chatham, MA Nestled in the charming coastal town of Chatham, this beautifully updated TURN KEY Cape ho...	3 beds \| 3 baths \| 2,062 sq.ft.	$1,275,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 1.51% Airbnb Rental Income: $2668 Traditional Rental Income: $3364 Airbnb ROI: 0.39% Traditional ROI: 1.51%
26 Hardings Beach Road Chatham, MA Perfectly positioned to capture breathtaking sunsets over Bucks Creek, this meticulously u...	4 beds \| 4 baths \| 2,700 sq.ft.	$2,995,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 0.63% Airbnb Rental Income: $2367 Traditional Rental Income: $5264 Airbnb ROI: -0.63% Traditional ROI: 0.63%
38 Indian Trail Chatham, MA This exceptional coastal retreat was designed to capture sweeping views of tidal salt mars...	4 beds \| 4 baths \| 4,967 sq.ft.	$4,495,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.11% Airbnb Rental Income: $2367 Traditional Rental Income: $6165 Airbnb ROI: -0.94% Traditional ROI: 0.11%
157 Bridge Street Chatham, MA In one of Chatham's most storied and visually captivating settings, adjacent to the iconic...	4 beds \| 6 baths \| 6,234 sq.ft.	$12,999,900	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.4% Airbnb Rental Income: $2367 Traditional Rental Income: $9232 Airbnb ROI: -1.01% Traditional ROI: -0.4%
99 Shane Drive Chatham, MA This charming ranch-style home offers an exceptional opportunity to own in Chatham, with p...	2 beds \| 2 baths \| 1,324 sq.ft.	$1,199,900	Airbnb cash on cash: 0.08% Traditional cash on cash: 1.2% Airbnb Rental Income: $2100 Traditional Rental Income: $2806 Airbnb ROI: 0.08% Traditional ROI: 1.2%
409 Main Street Chatham, MA Location,Location, Location ! 409 Main Street in the heart of downtown Chatham Village off...	1 beds \| 2 baths \| 1,479 sq.ft.	$2,100,000	Airbnb cash on cash: -0.62% Traditional cash on cash: -0.03% Airbnb Rental Income: $1822 Traditional Rental Income: $2479 Airbnb ROI: -0.62% Traditional ROI: -0.03%
558 Fox Hill Road Chatham, MA New co-ownership opportunity: own one-eighth of this professionally managed, turnkey home ...	5 beds \| 8 baths \| 11,000 sq.ft.	$1,469,000	Airbnb cash on cash: -1.88% Traditional cash on cash: 1.07% Airbnb Rental Income: $3611 Traditional Rental Income: $6840 Airbnb ROI: -1.88% Traditional ROI: 1.07%
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.	$5,495,000	Airbnb cash on cash: -1.94% Traditional cash on cash: -1.53% Airbnb Rental Income: $2100 Traditional Rental Income: $3622 Airbnb ROI: -1.94% Traditional ROI: -1.53%
87 Squanto Drive Chatham, MA Distinctive Home, Exceptional Location, Unmatched Lifestyle Discover refined coastal livin...	3 beds \| 4 baths \| 3,902 sq.ft.	$3,250,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 0.05% Airbnb Rental Income: $2668 Traditional Rental Income: $4344 Airbnb ROI: -0.72% Traditional ROI: 0.05%
346 Morris Island Road Chatham, MA Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfr...	4 beds \| 4 baths \| 2,850 sq.ft.	$4,500,000	Airbnb cash on cash: -0.91% Traditional cash on cash: -0.18% Airbnb Rental Income: $2367 Traditional Rental Income: $4824 Airbnb ROI: -0.91% Traditional ROI: -0.18%
30 Indian Trail Chatham, MA Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal showpie...	3 beds \| 3 baths \| 2,418 sq.ft.	$4,200,000	Airbnb cash on cash: -0.79% Traditional cash on cash: -0.26% Airbnb Rental Income: $2668 Traditional Rental Income: $4113 Airbnb ROI: -0.79% Traditional ROI: -0.26%
335 Stage Island Road Chatham, MA Situated on Chatham's exclusive Stage Island, this 4 BR, 5.5 bath, shingle-style residence...	4 beds \| 6 baths \| 5,372 sq.ft.	$4,495,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 0.56% Airbnb Rental Income: $2367 Traditional Rental Income: $8209 Airbnb ROI: -0.98% Traditional ROI: 0.56%
15 Bay Lane Chatham, MA Nestled in an elevated position overlooking Chatham Seaside Links, this architectural mast...	4 beds \| 5 baths \| 5,371 sq.ft.	$4,950,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.17% Airbnb Rental Income: $2367 Traditional Rental Income: $6609 Airbnb ROI: -0.88% Traditional ROI: 0.17%
68 Chippingstone Road Chatham, MA Welcome to Riverbay Estates, where Cape Cod charm meets endless potential. Enjoy peaceful ...	4 beds \| 3 baths \| 2,391 sq.ft.	$1,199,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 2.44% Airbnb Rental Income: $2367 Traditional Rental Income: $4356 Airbnb ROI: 0.13% Traditional ROI: 2.44%
213 Main Street Chatham, MA Perfectly positioned in the heart of Chatham's Old Village, this 4-bed, 2-bath home offers...	4 beds \| 2 baths \| 1,236 sq.ft.	$1,800,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.29% Airbnb Rental Income: $2367 Traditional Rental Income: $3107 Airbnb ROI: -0.51% Traditional ROI: 0.29%
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.	$3,595,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 0.62% Airbnb Rental Income: $2668 Traditional Rental Income: $6157 Airbnb ROI: -0.62% Traditional ROI: 0.62%
55 Winterset Drive Chatham, MA Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Es...	4 beds \| 4 baths \| 4,066 sq.ft.	$2,390,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 1.22% Airbnb Rental Income: $2367 Traditional Rental Income: $5532 Airbnb ROI: -0.47% Traditional ROI: 1.22%
7 Squanto Drive Chatham, MA This Nantucket-style home features extraordinary views across a tidal salt marsh and Oyste...	3 beds \| 4 baths \| 3,014 sq.ft.	$2,995,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 0.43% Airbnb Rental Income: $2668 Traditional Rental Income: $4844 Airbnb ROI: -0.58% Traditional ROI: 0.43%
101 Morris Island Road Chatham, MA LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery...	5 beds \| 5 baths \| 3,225 sq.ft.	$5,495,000	Airbnb cash on cash: -0.8% Traditional cash on cash: 0% Airbnb Rental Income: $3611 Traditional Rental Income: $6901 Airbnb ROI: -0.8% Traditional ROI: 0%
109 Misty Meadow Lane #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: 1.97% Traditional cash on cash: 3.22% Airbnb Rental Income: $2100 Traditional Rental Income: $2117 Airbnb ROI: 1.97% Traditional ROI: 3.22%
137 Shane Drive Chatham, MA Perfectly positioned on a corner lot in a quiet neighborhood, this beautifully maintained ...	3 beds \| 2 baths \| 1,530 sq.ft.	$1,399,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.92% Airbnb Rental Income: $2668 Traditional Rental Income: $2860 Airbnb ROI: 0.29% Traditional ROI: 0.92%
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.	$829,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 2.28% Airbnb Rental Income: $2668 Traditional Rental Income: $2852 Airbnb ROI: 1.22% Traditional ROI: 2.28%
169 Tisquantum Road Chatham, MA Located in Chatham's Quitnesset neighborhood on Morris Island, ideally situated between th...	5 beds \| 5 baths \| 5,587 sq.ft.	$4,900,000	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.07% Airbnb Rental Income: $3611 Traditional Rental Income: $5582 Airbnb ROI: -0.68% Traditional ROI: -0.07%
33 Crowell Road Chatham, MA A distinguished new residence by Eastward Companies, this exceptional home seamlessly blen...	3 beds \| 6 baths \| 5,820 sq.ft.	$4,499,900	Airbnb cash on cash: -0.56% Traditional cash on cash: 0.77% Airbnb Rental Income: $2668 Traditional Rental Income: $7553 Airbnb ROI: -0.56% Traditional ROI: 0.77%
912 Main Street #308 Chatham, MA Park Place is the Premiere Chatham address for an easy-care, maintenance-free lifestyle! T...	1 beds \| 2 baths \| 1,284 sq.ft.	$459,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 4.61% Airbnb Rental Income: $1822 Traditional Rental Income: $2627 Airbnb ROI: 1.59% Traditional ROI: 4.61%
32 Tip Cart Drive Chatham, MA Tucked into a sought-after neighborhood just moments from town, shopping, dining, beaches,...	3 beds \| 2 baths \| 1,802 sq.ft.	$1,350,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 1.23% Airbnb Rental Income: $2668 Traditional Rental Income: $3270 Airbnb ROI: 0.25% Traditional ROI: 1.23%
222 Barcliff Avenue Chatham, MA The location that has it all...walk to both town, fish pier, beach and baseball games....N...	4 beds \| 6 baths \| 3,980 sq.ft.	$4,250,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.13% Airbnb Rental Income: $2367 Traditional Rental Income: $8906 Airbnb ROI: -0.68% Traditional ROI: 1.13%
234 Round Cove Road Chatham, MA Tucked within Chatham's coveted Riverbay community, 234 Round Cove Road offers a rare blen...	3 beds \| 3 baths \| 2,481 sq.ft.	$2,150,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 0.88% Airbnb Rental Income: $2668 Traditional Rental Income: $4298 Airbnb ROI: -0.25% Traditional ROI: 0.88%
70 Judges Way Chatham, MA Experience refined coastal living in this fully renovated waterfront, water view estate on...	5 beds \| 5 baths \| 4,060 sq.ft.	$5,995,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 0.03% Airbnb Rental Income: $3611 Traditional Rental Income: $7171 Airbnb ROI: -0.75% Traditional ROI: 0.03%
48 Glover Square Chatham, MA Chatham By The Sea. Rare 50-year offering where LOCATION presents a premier opportunity in...	3 beds \| 2 baths \| 2,169 sq.ft.	$1,585,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 0.92% Airbnb Rental Income: $2668 Traditional Rental Income: $3342 Airbnb ROI: 0.03% Traditional ROI: 0.92%
60 Harbor Hill Road Chatham, MA Tucked away in Chatham's most desirable residential enclaves, this property offers a blend...	4 beds \| 4 baths \| 3,978 sq.ft.	$3,390,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.48% Airbnb Rental Income: $2367 Traditional Rental Income: $5449 Airbnb ROI: -0.68% Traditional ROI: 0.48%
260 Tanglewood Drive Chatham, MA Designed for one-floor living, this home is ideal as a retreat or year-round residence! In...	3 beds \| 2 baths \| 1,442 sq.ft.	$750,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.06% Airbnb Rental Income: $2668 Traditional Rental Income: $3148 Airbnb ROI: 1.47% Traditional ROI: 3.06%
336 Stage Island Road Chatham, MA Stage Island is among the most exclusive addresses on Cape Cod -- a private, tight-knit en...	3 beds \| 3 baths \| 2,205 sq.ft.	$2,995,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.22% Airbnb Rental Income: $2668 Traditional Rental Income: $4100 Airbnb ROI: -0.53% Traditional ROI: 0.22%
66 Snow Lane Chatham, MA Tucked away in the heart of Chatham, 66 Snow Lane offers a rare blend of privacy, convenie...	2 beds \| 1 baths \| 864 sq.ft.	$849,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 1.34% Airbnb Rental Income: $2100 Traditional Rental Income: $2113 Airbnb ROI: 0.64% Traditional ROI: 1.34%
7 Aunt Matties Road Chatham, MA Move to Chatham just in time for summer! This 2 bedroom home (with a bonus room for guests...	2 beds \| 2 baths \| 1,563 sq.ft.	$799,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 2.56% Airbnb Rental Income: $2100 Traditional Rental Income: $2939 Airbnb ROI: 0.71% Traditional ROI: 2.56%
700 Riverview Drive Chatham, MA Nestled in one of Chatham's sought-after neighborhoods, this home is designed for both eve...	3 beds \| 3 baths \| 3,190 sq.ft.	$1,650,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 1.23% Airbnb Rental Income: $2668 Traditional Rental Income: $3948 Airbnb ROI: -0.02% Traditional ROI: 1.23%
333 Old Comers Road Chatham, MA Tucked into one of Chatham's most coveted pockets - moments from Jackknife and Ryder's Cov...	4 beds \| 3 baths \| 2,384 sq.ft.	$1,495,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 1.81% Airbnb Rental Income: $2367 Traditional Rental Income: $4261 Airbnb ROI: 0.03% Traditional ROI: 1.81%
367 Deer Meadow Lane Chatham, MA Nestled in Chatham's highly sought-after RiverBay neighborhood, this beautifully updated C...	3 beds \| 3 baths \| 2,264 sq.ft.	$1,475,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.38% Airbnb Rental Income: $2668 Traditional Rental Income: $3681 Airbnb ROI: 0.18% Traditional ROI: 1.38%
33 Jeanette Road Chatham, MA Lovingly updated and meticulously maintained, this turnkey 3-bedroom, 2-bath ranch offers ...	3 beds \| 2 baths \| 1,392 sq.ft.	$985,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 2.04% Airbnb Rental Income: $2668 Traditional Rental Income: $3121 Airbnb ROI: 0.86% Traditional ROI: 2.04%

Real Estate investment in Chatham, MA

There are 50 properties for sale in the city of Chatham . The median list price in Chatham is $1,416,652 and the average price per square foot is $480. In July 2026, the average monthly cash on cash return in Chatham is 1.00%. The average monthly rental income in Chatham is $3,531.

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

There are 50 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 $2,367.

Your search for investment property begins and ends here

Investment Property for Sale in Chatham, MA

58 Stepping Stones Road

Chatham, MA

3 beds | 3 baths | 2,062 sq.ft.

$1,275,000

Airbnb cash on cash: 0.39%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $2668

Traditional Rental Income: $3364

Airbnb ROI: 0.39%

Traditional ROI: 1.51%

26 Hardings Beach Road

Chatham, MA

4 beds | 4 baths | 2,700 sq.ft.

$2,995,000

Airbnb cash on cash: -0.63%

Traditional cash on cash: 0.63%

Airbnb Rental Income: $2367

Traditional Rental Income: $5264

Airbnb ROI: -0.63%

Traditional ROI: 0.63%

38 Indian Trail

Chatham, MA

4 beds | 4 baths | 4,967 sq.ft.

$4,495,000

Airbnb cash on cash: -0.94%

Traditional cash on cash: 0.11%

Airbnb Rental Income: $2367

Traditional Rental Income: $6165

Airbnb ROI: -0.94%

Traditional ROI: 0.11%

157 Bridge Street

Chatham, MA

4 beds | 6 baths | 6,234 sq.ft.

$12,999,900

Airbnb cash on cash: -1.01%

Traditional cash on cash: -0.4%

Airbnb Rental Income: $2367

Traditional Rental Income: $9232

Airbnb ROI: -1.01%

Traditional ROI: -0.4%

99 Shane Drive

Chatham, MA

2 beds | 2 baths | 1,324 sq.ft.

$1,199,900

Airbnb cash on cash: 0.08%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $2100

Traditional Rental Income: $2806

Airbnb ROI: 0.08%

Traditional ROI: 1.2%

409 Main Street

Chatham, MA

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

$2,100,000

Airbnb cash on cash: -0.62%

Traditional cash on cash: -0.03%

Airbnb Rental Income: $1822

Traditional Rental Income: $2479

Airbnb ROI: -0.62%

Traditional ROI: -0.03%

558 Fox Hill Road

Chatham, MA

5 beds | 8 baths | 11,000 sq.ft.

$1,469,000

Airbnb cash on cash: -1.88%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $3611

Traditional Rental Income: $6840

Airbnb ROI: -1.88%

Traditional ROI: 1.07%

99 Uncle Alberts Drive Ext

Chatham, MA

2 beds | 3 baths | 1,850 sq.ft.

$5,495,000

Airbnb cash on cash: -1.94%

Traditional cash on cash: -1.53%

Airbnb Rental Income: $2100

Traditional Rental Income: $3622

Airbnb ROI: -1.94%