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.

Single Family Homes for Sale in Chatham, MA

Search for Single Family Residential for Sale in Chatham, Massachusetts. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 30 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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: N/A Traditional cash on cash: 0.37% Airbnb Rental Income: $null Traditional Rental Income: $4966 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.67% Airbnb Rental Income: $null Traditional Rental Income: $8510 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.64% Airbnb Rental Income: $null Traditional Rental Income: $3808 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.71% Airbnb Rental Income: $null Traditional Rental Income: $3017 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.35% Airbnb Rental Income: $null Traditional Rental Income: $3219 Airbnb ROI: N/A 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: N/A Traditional cash on cash: -1.53% Airbnb Rental Income: $null Traditional Rental Income: $3622 Airbnb ROI: N/A 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: N/A Traditional cash on cash: -0.18% Airbnb Rental Income: $null Traditional Rental Income: $4824 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.51% Airbnb Rental Income: $null Traditional Rental Income: $6157 Airbnb ROI: N/A Traditional ROI: 0.51%
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.	$5,995,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.08% Airbnb Rental Income: $null Traditional Rental Income: $6901 Airbnb ROI: N/A Traditional ROI: -0.08%
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: N/A Traditional cash on cash: -0.25% Airbnb Rental Income: $null Traditional Rental Income: $8387 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.22% Airbnb Rental Income: $null Traditional Rental Income: $4849 Airbnb ROI: N/A 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: N/A Traditional cash on cash: -0.1% Airbnb Rental Income: $null Traditional Rental Income: $8921 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.93% Airbnb Rental Income: $null Traditional Rental Income: $3640 Airbnb ROI: N/A Traditional ROI: 1.93%
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: N/A Traditional cash on cash: 1.13% Airbnb Rental Income: $null Traditional Rental Income: $3352 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.44% Airbnb Rental Income: $null Traditional Rental Income: $3467 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.8% Airbnb Rental Income: $null Traditional Rental Income: $2860 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.39% Airbnb Rental Income: $null Traditional Rental Income: $3101 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.25% Airbnb Rental Income: $null Traditional Rental Income: $2852 Airbnb ROI: N/A Traditional ROI: 2.25%
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: N/A Traditional cash on cash: -0.16% Airbnb Rental Income: $null Traditional Rental Income: $5582 Airbnb ROI: N/A Traditional ROI: -0.16%
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: N/A Traditional cash on cash: 0.34% Airbnb Rental Income: $null Traditional Rental Income: $3919 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.77% Airbnb Rental Income: $null Traditional Rental Income: $7553 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.98% Airbnb Rental Income: $null Traditional Rental Income: $2981 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.91% Airbnb Rental Income: $null Traditional Rental Income: $3642 Airbnb ROI: N/A Traditional ROI: 0.91%
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: N/A Traditional cash on cash: 1.08% Airbnb Rental Income: $null Traditional Rental Income: $3270 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.18% Airbnb Rental Income: $null Traditional Rental Income: $8906 Airbnb ROI: N/A Traditional ROI: 1.18%
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: N/A Traditional cash on cash: 1.74% Airbnb Rental Income: $null Traditional Rental Income: $3467 Airbnb ROI: N/A Traditional ROI: 1.74%
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: N/A Traditional cash on cash: 4.01% Airbnb Rental Income: $null Traditional Rental Income: $3094 Airbnb ROI: N/A Traditional ROI: 4.01%
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.	$2,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.8% Airbnb Rental Income: $null Traditional Rental Income: $4298 Airbnb ROI: N/A Traditional ROI: 0.8%
70 Old Queen Anne Road Chatham, MA Don't miss this inviting 3-bedroom Cape with classic New England appeal, nicely sited on o...	3 beds \| 4 baths \| 2,248 sq.ft.	$1,795,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.33% Airbnb Rental Income: $null Traditional Rental Income: $4332 Airbnb ROI: N/A Traditional ROI: 1.33%
25 Wood Valley Road Chatham, MA Nestled on a quiet cul-de-sac with deeded access to Lovers Lake, this 4-bedroom, 2-bath Ca...	4 beds \| 2 baths \| 2,004 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $3539 Airbnb ROI: N/A Traditional ROI: 2.61%

Your search for investment property begins and ends here

Single Family Homes 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: N/A

Traditional cash on cash: 0.37%

Airbnb Rental Income: $null

Traditional Rental Income: $4966

Airbnb ROI: N/A

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: N/A

Traditional cash on cash: 0.67%

Airbnb Rental Income: $null

Traditional Rental Income: $8510

Airbnb ROI: N/A

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: N/A

Traditional cash on cash: 0.64%

Airbnb Rental Income: $null

Traditional Rental Income: $3808

Airbnb ROI: N/A

Traditional ROI: 0.64%

39 Jedidiah Way

Chatham, MA

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

$1,650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.71%

Airbnb Rental Income: $null

Traditional Rental Income: $3017

Airbnb ROI: N/A

Traditional ROI: 0.71%

46 Chippingstone Road

Chatham, MA

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

$919,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.35%

Airbnb Rental Income: $null

Traditional Rental Income: $3219

Airbnb ROI: N/A

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: N/A

Traditional cash on cash: -1.53%

Airbnb Rental Income: $null

Traditional Rental Income: $3622

Airbnb ROI: N/A

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: N/A

Traditional cash on cash: -0.18%

Airbnb Rental Income: $null

Traditional Rental Income: $4824

Airbnb ROI: N/A

Traditional ROI: -0.18%

287 Cedar Street

Chatham, MA

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

$3,850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.51%

Airbnb Rental Income: $null

Traditional Rental Income: $6157

Airbnb ROI: N/A