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
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: -0.44% Traditional cash on cash: 1.51% Airbnb Rental Income: $1486 Traditional Rental Income: $3364 Airbnb ROI: -0.44% Traditional ROI: 1.51%
61 Oak Hill Road Chatham, MA Easy one-floor living in Chatham can be yours in this sun-filled 2 bedroom home that inclu...	2 beds \| 2 baths \| 1,688 sq.ft.	$865,900	Airbnb cash on cash: -0.75% Traditional cash on cash: 2.36% Airbnb Rental Income: $888 Traditional Rental Income: $3062 Airbnb ROI: -0.75% Traditional ROI: 2.36%
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.	$4,750,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.05% Airbnb Rental Income: $1908 Traditional Rental Income: $6165 Airbnb ROI: -1.03% Traditional ROI: 0.05%
393 Training Field Road Chatham, MA Welcome to 393 Training Field Road, a beautifully renovated three-bedroom, two full and tw...	3 beds \| 3 baths \| 3,645 sq.ft.	$1,615,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 1.32% Airbnb Rental Income: $1486 Traditional Rental Income: $3894 Airbnb ROI: -0.57% Traditional ROI: 1.32%
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: -1.05% Traditional cash on cash: -0.4% Airbnb Rental Income: $1908 Traditional Rental Income: $9232 Airbnb ROI: -1.05% Traditional ROI: -0.4%
1340 Main Street #9 Chatham, MA Very rare opportunity to own a free-standing cottage in the beloved Waterview Colony on Wh...	2 beds \| 1 baths \| 496 sq.ft.	$490,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.6% Airbnb Rental Income: $888 Traditional Rental Income: $1890 Airbnb ROI: -0.32% Traditional ROI: 2.6%
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: -0.9% Traditional cash on cash: 0.71% Airbnb Rental Income: $888 Traditional Rental Income: $3017 Airbnb ROI: -0.9% Traditional ROI: 0.71%
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: -2.13% Traditional cash on cash: -1.53% Airbnb Rental Income: $888 Traditional Rental Income: $3622 Airbnb ROI: -2.13% 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: -1% Traditional cash on cash: -0.18% Airbnb Rental Income: $1908 Traditional Rental Income: $4824 Airbnb ROI: -1% Traditional ROI: -0.18%
92 Absegami Run Chatham, MA Newly renovated and beautifully refreshed, this exceptional 4-bedroom, 3.5-bath home is se...	4 beds \| 4 baths \| 3,199 sq.ft.	$3,699,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.12% Airbnb Rental Income: $1908 Traditional Rental Income: $4608 Airbnb ROI: -0.82% Traditional ROI: 0.12%
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: -1.04% Traditional cash on cash: -0.26% Airbnb Rental Income: $1486 Traditional Rental Income: $4113 Airbnb ROI: -1.04% Traditional ROI: -0.26%
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: -0.97% Traditional cash on cash: 0.17% Airbnb Rental Income: $1908 Traditional Rental Income: $6609 Airbnb ROI: -0.97% Traditional ROI: 0.17%
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: -0.92% Traditional cash on cash: 0.62% Airbnb Rental Income: $1486 Traditional Rental Income: $6157 Airbnb ROI: -0.92% Traditional ROI: 0.62%
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: -0.93% Traditional cash on cash: 0.43% Airbnb Rental Income: $1486 Traditional Rental Income: $4844 Airbnb ROI: -0.93% 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.	$5,995,000	Airbnb cash on cash: -0.87% Traditional cash on cash: -0.08% Airbnb Rental Income: $3266 Traditional Rental Income: $6901 Airbnb ROI: -0.87% 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: -1.91% Traditional cash on cash: -0.25% Airbnb Rental Income: $1908 Traditional Rental Income: $8387 Airbnb ROI: -1.91% Traditional ROI: -0.25%
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: -1.11% Traditional cash on cash: -0.1% Airbnb Rental Income: $1908 Traditional Rental Income: $8921 Airbnb ROI: -1.11% 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: -0.39% Traditional cash on cash: 1.93% Airbnb Rental Income: $1486 Traditional Rental Income: $3640 Airbnb ROI: -0.39% Traditional ROI: 1.93%
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: -0.3% Traditional cash on cash: 3.22% Airbnb Rental Income: $888 Traditional Rental Income: $2117 Airbnb ROI: -0.3% Traditional ROI: 3.22%
29 Jessies Landing Chatham, MA This exceptional new luxury residence by Eastward Companies offers the rare opportunity to...	3 beds \| 5 baths \| 4,565 sq.ft.	$3,699,900	Airbnb cash on cash: -0.86% Traditional cash on cash: -0.26% Airbnb Rental Income: $1486 Traditional Rental Income: $3128 Airbnb ROI: -0.86% Traditional ROI: -0.26%
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: -0.5% Traditional cash on cash: 0.8% Airbnb Rental Income: $1486 Traditional Rental Income: $2860 Airbnb ROI: -0.5% 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: -0.71% Traditional cash on cash: 0.39% Airbnb Rental Income: $1486 Traditional Rental Income: $3101 Airbnb ROI: -0.71% 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: -0.07% Traditional cash on cash: 2.23% Airbnb Rental Income: $1486 Traditional Rental Income: $2852 Airbnb ROI: -0.07% Traditional ROI: 2.23%
425 Main Street #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: 0.07% Traditional cash on cash: 1.98% Airbnb Rental Income: $1368 Traditional Rental Income: $1755 Airbnb ROI: 0.07% Traditional ROI: 1.98%
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: -0.77% Traditional cash on cash: -0.16% Airbnb Rental Income: $3266 Traditional Rental Income: $5582 Airbnb ROI: -0.77% 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: -0.89% Traditional cash on cash: 0.34% Airbnb Rental Income: $1486 Traditional Rental Income: $3919 Airbnb ROI: -0.89% 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: -0.79% Traditional cash on cash: 0.77% Airbnb Rental Income: $1486 Traditional Rental Income: $7553 Airbnb ROI: -0.79% 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: 0.19% Traditional cash on cash: 1.98% Airbnb Rental Income: $1908 Traditional Rental Income: $2981 Airbnb ROI: 0.19% Traditional ROI: 1.98%
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: 0.71% Traditional cash on cash: 4.61% Airbnb Rental Income: $1368 Traditional Rental Income: $2627 Airbnb ROI: 0.71% 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: -0.57% Traditional cash on cash: 1.08% Airbnb Rental Income: $1486 Traditional Rental Income: $3270 Airbnb ROI: -0.57% 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.	$4,250,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.13% Airbnb Rental Income: $1908 Traditional Rental Income: $8906 Airbnb ROI: -0.78% Traditional ROI: 1.13%
118 Wilfred Road Chatham, MA PONDVIEW: Welcome to 118 Wilfred Road, a charming Cape-style home tucked into one of Chath...	3 beds \| 3 baths \| 1,804 sq.ft.	$1,200,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 1.74% Airbnb Rental Income: $1486 Traditional Rental Income: $3467 Airbnb ROI: -0.43% Traditional ROI: 1.74%
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: -0.75% Traditional cash on cash: 0.88% Airbnb Rental Income: $1486 Traditional Rental Income: $4298 Airbnb ROI: -0.75% Traditional ROI: 0.88%
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: 0.19% Traditional cash on cash: 2.61% Airbnb Rental Income: $1908 Traditional Rental Income: $3539 Airbnb ROI: 0.19% Traditional ROI: 2.61%
22 Starfish Lane #22 Chatham, MA Beautifully renovated inside and out oceanfront townhome nestled in the heart of Chatham. ...	2 beds \| 2 baths \| 950 sq.ft.	$760,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 2.32% Airbnb Rental Income: $888 Traditional Rental Income: $2655 Airbnb ROI: -0.65% Traditional ROI: 2.32%
6-894 Munson Meeting Way Chatham, MA Positioned in the heart of Chatham, 894 Main Street presents a rare mixed-use investment i...	2 beds \| 3 baths \| 1,773 sq.ft.	$699,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 3.9% Airbnb Rental Income: $888 Traditional Rental Income: $3512 Airbnb ROI: -0.65% Traditional ROI: 3.9%
42 Champlain Road Chatham, MA Nestled in a premier Stage Harbor location, this 4-bedroom, 2-bath property presents an ex...	4 beds \| 2 baths \| 1,435 sq.ft.	$1,800,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 0.68% Airbnb Rental Income: $1908 Traditional Rental Income: $3344 Airbnb ROI: -0.48% Traditional ROI: 0.68%
298 Chippingstone Road Chatham, MA Set on a beautifully landscaped half-acre lot in one of Chatham's most sought-after neighb...	4 beds \| 2 baths \| 2,148 sq.ft.	$1,050,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 2.34% Airbnb Rental Income: $1908 Traditional Rental Income: $3626 Airbnb ROI: 0.06% Traditional ROI: 2.34%
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: -0.8% Traditional cash on cash: 0.03% Airbnb Rental Income: $3266 Traditional Rental Income: $7171 Airbnb ROI: -0.8% Traditional ROI: 0.03%
48 Glover Square Chatham, MA Chatham By The Sea. Rare 50-year offering at 48 Glover Square presents a premier opportuni...	3 beds \| 2 baths \| 2,169 sq.ft.	$1,650,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.84% Airbnb Rental Income: $1486 Traditional Rental Income: $3342 Airbnb ROI: -0.66% Traditional ROI: 0.84%

Real Estate investment in Chatham, MA

There are 45 properties for sale in the city of Chatham . The median list price in Chatham is $1,800,000 and the average price per square foot is $673. In May 2026, the average monthly cash on cash return in Chatham is 1.00%. The average monthly rental income in Chatham is $3,522.

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

There are 45 investment properties available for sale in Chatham.

In 2026, the best neighborhood to buy investment property is Chatham.

The ROI for Long-Term is higher than the Short-Term in Chatham with average rental income of $3,522.

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: -0.44%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $1486

Traditional Rental Income: $3364

Airbnb ROI: -0.44%

Traditional ROI: 1.51%

61 Oak Hill Road

Chatham, MA

2 beds | 2 baths | 1,688 sq.ft.

$865,900

Airbnb cash on cash: -0.75%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $888

Traditional Rental Income: $3062

Airbnb ROI: -0.75%

Traditional ROI: 2.36%

38 Indian Trail

Chatham, MA

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

$4,750,000

Airbnb cash on cash: -1.03%

Traditional cash on cash: 0.05%

Airbnb Rental Income: $1908

Traditional Rental Income: $6165

Airbnb ROI: -1.03%

Traditional ROI: 0.05%

393 Training Field Road

Chatham, MA

3 beds | 3 baths | 3,645 sq.ft.

$1,615,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 1.32%

Airbnb Rental Income: $1486

Traditional Rental Income: $3894

Airbnb ROI: -0.57%

Traditional ROI: 1.32%

157 Bridge Street

Chatham, MA

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

$12,999,900

Airbnb cash on cash: -1.05%

Traditional cash on cash: -0.4%

Airbnb Rental Income: $1908

Traditional Rental Income: $9232

Airbnb ROI: -1.05%

Traditional ROI: -0.4%

1340 Main Street #9

Chatham, MA

2 beds | 1 baths | 496 sq.ft.

$490,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $888

Traditional Rental Income: $1890

Airbnb ROI: -0.32%

Traditional ROI: 2.6%

39 Jedidiah Way

Chatham, MA

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

$1,650,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $888

Traditional Rental Income: $3017

Airbnb ROI: -0.9%

Traditional ROI: 0.71%

99 Uncle Alberts Drive Ext

Chatham, MA

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

$5,495,000

Airbnb cash on cash: -2.13%

Traditional cash on cash: -1.53%

Airbnb Rental Income: $888

Traditional Rental Income: $3622

Airbnb ROI: -2.13%