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 Jessies Landing Chatham, MA Welcome to this beautifully crafted residence in Jessie's Landing, an exclusive Eastward C...	3 beds \| 4 baths \| 2,940 sq.ft.	$3,299,900	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.37% Airbnb Rental Income: $2063 Traditional Rental Income: $4966 Airbnb ROI: -0.76% Traditional ROI: 0.37%
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%
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.	$2,100,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.64% Airbnb Rental Income: $2063 Traditional Rental Income: $3808 Airbnb ROI: -0.53% Traditional ROI: 0.64%
39 Jedidiah Way Chatham, MA 39 Jedidiah Way, has been gently utilized by the same family for the past 29 years, servin...	2 beds \| 2 baths \| 1,810 sq.ft.	$1,650,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.71% Airbnb Rental Income: $1648 Traditional Rental Income: $3017 Airbnb ROI: -0.49% Traditional ROI: 0.71%
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.	$919,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.35% Airbnb Rental Income: $2063 Traditional Rental Income: $3219 Airbnb ROI: 0.38% Traditional ROI: 2.35%
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: -2.01% Traditional cash on cash: -1.53% Airbnb Rental Income: $1648 Traditional Rental Income: $3622 Airbnb ROI: -2.01% Traditional ROI: -1.53%
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: -0.69% Traditional cash on cash: -0.18% Airbnb Rental Income: $3498 Traditional Rental Income: $4824 Airbnb ROI: -0.69% Traditional ROI: -0.18%
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.	$3,850,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.51% Airbnb Rental Income: $2063 Traditional Rental Income: $6157 Airbnb ROI: -0.79% Traditional ROI: 0.51%
230 Barcliff Avenue Chatham, MA Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underwa...	4 beds \| 6 baths \| 5,300 sq.ft.	$4,525,000	Airbnb cash on cash: -1.6% Traditional cash on cash: -0.25% Airbnb Rental Income: $3498 Traditional Rental Income: $8387 Airbnb ROI: -1.6% Traditional ROI: -0.25%
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%
246 Stage Island Road Chatham, MA Set on nearly an acre in one of Chatham's most coveted enclaves, this Stage Island residen...	4 beds \| 5 baths \| 4,717 sq.ft.	$7,999,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.1% Airbnb Rental Income: $3498 Traditional Rental Income: $8921 Airbnb ROI: -0.93% Traditional ROI: -0.1%
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 \| 3 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%
425 Main Street unit: 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.	$450,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 2.74% Airbnb Rental Income: $1558 Traditional Rental Income: $1812 Airbnb ROI: 1.08% Traditional ROI: 2.74%
28 Lakeview Avenue Chatham, MA Welcome to 28 Lakeview Ave...a Riverbay gem in a natural setting. Beautifully renovated wi...	3 beds \| 3 baths \| 2,441 sq.ft.	$1,495,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.13% Airbnb Rental Income: $2063 Traditional Rental Income: $3352 Airbnb ROI: -0.18% Traditional ROI: 1.13%
8 Kingsbury Way Chatham, MA Tucked away at the end of a private lane in the heart of town, this charming 3-bedroom, 2....	3 beds \| 3 baths \| 1,651 sq.ft.	$2,199,900	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.44% Airbnb Rental Income: $2063 Traditional Rental Income: $3467 Airbnb ROI: -0.51% Traditional ROI: 0.44%
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.	$1,495,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.8% Airbnb Rental Income: $2063 Traditional Rental Income: $2860 Airbnb ROI: -0.16% Traditional ROI: 0.8%
50 Eldredge Square S Chatham, MA Ideally situated just moments from Chatham's Village boutiques and restaurants, this excep...	3 beds \| 2 baths \| 1,488 sq.ft.	$1,995,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 0.39% Airbnb Rental Income: $2063 Traditional Rental Income: $3101 Airbnb ROI: -0.45% Traditional ROI: 0.39%
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%
121 Queen Anne Road Chatham, MA Set in one of Chatham's most coveted in-town locations, this refined coastal residence off...	4 beds \| 6 baths \| 3,702 sq.ft.	$5,400,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.45% Airbnb Rental Income: $3498 Traditional Rental Income: $8649 Airbnb ROI: -0.73% Traditional ROI: 0.45%
169 Tisquantum Road Chatham, MA Nestled in Chatham's exclusive Morris Island neighborhood, this home embodies the quintess...	5 beds \| 5 baths \| 5,587 sq.ft.	$5,400,000	Airbnb cash on cash: -0.35% Traditional cash on cash: -0.16% Airbnb Rental Income: $5760 Traditional Rental Income: $5582 Airbnb ROI: -0.35% Traditional ROI: -0.16%
1 Seastrand Way unit: 1 Chatham, MA Rare opportunity to own this totally renovated secluded end unit which feels like a 1296 s...	2 beds \| 2 baths \| 1,296 sq.ft.	$695,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.86% Airbnb Rental Income: $1648 Traditional Rental Income: $2755 Airbnb ROI: 0.43% Traditional ROI: 2.86%
16 Old Salt Works Road Chatham, MA This charming Cape-style home is located in Eastward Point, one of Chatham's most coveted ...	3 beds \| 3 baths \| 2,426 sq.ft.	$2,500,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.34% Airbnb Rental Income: $2063 Traditional Rental Income: $3919 Airbnb ROI: -0.68% Traditional ROI: 0.34%
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: -0.68% Traditional cash on cash: 0.77% Airbnb Rental Income: $2063 Traditional Rental Income: $7553 Airbnb ROI: -0.68% Traditional ROI: 0.77%
66 Ethelma Drive Chatham, MA 66 Ethelma Drive is a rare pond front opportunity in Chatham, MA, set along the shores of ...	4 beds \| 1 baths \| 1,547 sq.ft.	$949,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 1.98% Airbnb Rental Income: $3498 Traditional Rental Income: $2981 Airbnb ROI: 1.69% Traditional ROI: 1.98%
146 Old Field Bend Chatham, MA Elevated on a .57 acre lot in a serene North Chatham setting within Ryder's Cove Landing A...	3 beds \| 3 baths \| 2,039 sq.ft.	$1,750,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 0.91% Airbnb Rental Income: $2063 Traditional Rental Income: $3642 Airbnb ROI: -0.39% Traditional ROI: 0.91%
912 Main Street unit: 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: 1.08% Traditional cash on cash: 4.61% Airbnb Rental Income: $1558 Traditional Rental Income: $2627 Airbnb ROI: 1.08% 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.	$1,450,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.08% Airbnb Rental Income: $2063 Traditional Rental Income: $3270 Airbnb ROI: -0.21% Traditional ROI: 1.08%
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.	$4,150,000	Airbnb cash on cash: -0.43% Traditional cash on cash: -0.22% Airbnb Rental Income: $3498 Traditional Rental Income: $3505 Airbnb ROI: -0.43% Traditional ROI: -0.22%
118 Wilfred Road Chatham, MA PONDFRONT: Welcome to 118 Wilfred Road, a charming Cape-style home tucked into one of Chat...	3 beds \| 3 baths \| 1,804 sq.ft.	$1,200,000	Airbnb cash on cash: 0% Traditional cash on cash: 1.37% Airbnb Rental Income: $2063 Traditional Rental Income: $3052 Airbnb ROI: 0% Traditional ROI: 1.37%
100 Heritage Lane Chatham, MA Located in desirable Chatham, this 4-bedroom, 1.5-bath home presents a rare opportunity to...	4 beds \| 2 baths \| 1,144 sq.ft.	$599,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 4.01% Airbnb Rental Income: $3498 Traditional Rental Income: $3094 Airbnb ROI: 3.35% Traditional ROI: 4.01%

Real Estate investment in Chatham, MA

There are 30 properties for sale in the city of Chatham . The median list price in Chatham is $1,872,500 and the average price per square foot is $715. In April 2026, the average monthly cash on cash return in Chatham is 1.00%. The average monthly rental income in Chatham is $3,516.

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

There are 30 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 $2,063.

Your search for investment property begins and ends here

Investment Property for Sale in Chatham, MA

20 Jessies Landing

Chatham, MA

3 beds | 4 baths | 2,940 sq.ft.

$3,299,900

Airbnb cash on cash: -0.76%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $2063

Traditional Rental Income: $4966

Airbnb ROI: -0.76%

Traditional ROI: 0.37%

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%

55 Christopher Harding Lane

Chatham, MA

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

$2,100,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 0.64%

Airbnb Rental Income: $2063

Traditional Rental Income: $3808

Airbnb ROI: -0.53%

Traditional ROI: 0.64%

39 Jedidiah Way

Chatham, MA

2 beds | 2 baths | 1,810 sq.ft.

$1,650,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $1648

Traditional Rental Income: $3017

Airbnb ROI: -0.49%

Traditional ROI: 0.71%

46 Chippingstone Road

Chatham, MA

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

$919,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $2063

Traditional Rental Income: $3219

Airbnb ROI: 0.38%

Traditional ROI: 2.35%

99 Uncle Alberts Drive Ext

Chatham, MA

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

$5,495,000

Airbnb cash on cash: -2.01%

Traditional cash on cash: -1.53%

Airbnb Rental Income: $1648

Traditional Rental Income: $3622

Airbnb ROI: -2.01%

Traditional ROI: -1.53%

346 Morris Island Road

Chatham, MA

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

$4,500,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: -0.18%

Airbnb Rental Income: $3498

Traditional Rental Income: $4824

Airbnb ROI: -0.69%

Traditional ROI: -0.18%

287 Cedar Street

Chatham, MA

3 beds | 5 baths | 3,640 sq.ft.

$3,850,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: 0.51%

Airbnb Rental Income: $2063

Traditional Rental Income: $6157

Airbnb ROI: -0.79%