Real Estate Investment Properties for Sale in Chaplin, CT

Looking for investment property in Chaplin, CT with high ROI ?

Explore a variety of short-term homes & houses in Chaplin, CT. Invest wisely with VRBO & Chaplin, CT 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 Chaplin, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
287 S Bear Hill Road Chaplin, CT If you are looking for everything this is the home for you. Home sits on 3.39 acres of bea...	4 beds \| 3 baths \| 2,900 sq.ft.	$789,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.1% Airbnb Rental Income: $null Traditional Rental Income: $4788 Airbnb ROI: N/A Traditional ROI: 4.1%
60 Chaplin Street Chaplin, CT Welcome to the original parsonage of the Chaplin Congregational Church in the historic dis...	3 beds \| 2 baths \| 2,438 sq.ft.	$425,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 5.3% Airbnb Rental Income: $2113 Traditional Rental Income: $3138 Airbnb ROI: 1.36% Traditional ROI: 5.3%
Investment Properties for Sale in Other Cities of Connecticut
150 Kaynor Drive Waterbury , CT Bunker Hill Ranch, one level living, refirnished hardwood flooring. Home freshly painted, ...	3 beds \| 2 baths \| 1,300 sq.ft.	$339,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 5.24% Airbnb Rental Income: $1394 Traditional Rental Income: $2686 Airbnb ROI: -0.12% Traditional ROI: 5.24%
23 Heaton Street Waterbury , CT Beautiful 3-Bedroom Home Built in 2009 - Move-In Ready! Welcome to 23 Heaton Street, a wel...	3 beds \| 3 baths \| 1,716 sq.ft.	$374,995	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.94% Airbnb Rental Income: $1673 Traditional Rental Income: $2715 Airbnb ROI: -0.35% Traditional ROI: 3.94%
2 Elmwood Drive unit: 2 #2 Fairfield , CT Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro...	3 beds \| 4 baths \| 3,328 sq.ft.	$2,399,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 0.1% Airbnb Rental Income: $2373 Traditional Rental Income: $5995 Airbnb ROI: -1.79% Traditional ROI: 0.1%
360 N Society Road Canterbury , CT INSTANT EQUITY when you finish this SPRAWLING Cape it COMPS out $525,000 to $550,000! OVER...	3 beds \| 2 baths \| 2,236 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.03% Airbnb Rental Income: $null Traditional Rental Income: $3171 Airbnb ROI: N/A Traditional ROI: 9.03%
19 Clover Court New London , CT Investor Alert - Well maintained 3 bedroom colonial on a dead end street with paved drivew...	3 beds \| 1 baths \| 1,311 sq.ft.	$209,900	Airbnb cash on cash: 4.83% Traditional cash on cash: 7.84% Airbnb Rental Income: $2087 Traditional Rental Income: $2148 Airbnb ROI: 4.83% Traditional ROI: 7.84%
1 Broad Street #PHD2 Stamford , CT Luxury living at its finest. Park Tower 35th floor Penthouse Duplex boasting living room w...	3 beds \| 4 baths \| 3,341 sq.ft.	$2,000,000	Airbnb cash on cash: -3.84% Traditional cash on cash: -1.35% Airbnb Rental Income: $2038 Traditional Rental Income: $6132 Airbnb ROI: -3.84% Traditional ROI: -1.35%
286 Moose Hill Road Monroe , CT Welcome to this well maintained ranch style home nestled away from nearby amenities, but c...	2 beds \| 3 baths \| 1,012 sq.ft.	$549,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 2.7% Airbnb Rental Income: $2198 Traditional Rental Income: $2727 Airbnb ROI: 0.59% Traditional ROI: 2.7%
16 Marlene Drive Ledyard , CT RARE FIND! A 4-bedroom mobile home on its own land. You heard me right. Vinyl sided, newer...	4 beds \| 1 baths \| 1,260 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.16% Airbnb Rental Income: $null Traditional Rental Income: $2298 Airbnb ROI: N/A Traditional ROI: 10.16%
32 WILLINGTON AVENUE Stafford Springs , CT Completely renovated old-style Colonial that sits on1.72 private acres. Nestled in the woo...	3 beds \| 2 baths \| 1,047 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2593 Airbnb ROI: N/A Traditional ROI: 5.4%
619 Queen Street Bridgeport , CT Here's your chance to own a highly sought-after rental property in Bridgeport's North End,...	3 beds \| 1 baths \| 864 sq.ft.	$359,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.88% Airbnb Rental Income: $1671 Traditional Rental Income: $2273 Airbnb ROI: 0.71% Traditional ROI: 3.88%
254 Seaside Avenue unit: A #A Stamford , CT Welcome to effortless coastal living in the heart of Stamford's coveted Cove Beach neighbo...	2 beds \| 2 baths \| 1,253 sq.ft.	$440,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 4.44% Airbnb Rental Income: $1500 Traditional Rental Income: $3203 Airbnb ROI: -0.76% Traditional ROI: 4.44%
1462 South Avenue Stratford , CT This absolutely charming, bright, and tastefully updated condo alternative checks every bo...	3 beds \| 2 baths \| 1,152 sq.ft.	$299,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 7.73% Airbnb Rental Income: $2065 Traditional Rental Income: $3013 Airbnb ROI: 2.47% Traditional ROI: 7.73%
153 THOMPSON HILL RD Portland , CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,704 sq.ft.	$451,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.54% Airbnb Rental Income: $1388 Traditional Rental Income: $2560 Airbnb ROI: -0.23% Traditional ROI: 3.54%
180 E Rocks Road Norwalk , CT Welcome to 180 East Rocks Road in the desirable Cranbury neighborhood. Experience comfort ...	4 beds \| 3 baths \| 3,332 sq.ft.	$1,050,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 3.27% Airbnb Rental Income: $4407 Traditional Rental Income: $5637 Airbnb ROI: 1.07% Traditional ROI: 3.27%

Real Estate investment in Chaplin, CT

There are 2 properties for sale in the city of Chaplin . The median list price in Chaplin is $607,000 and the average price per square foot is $227. In January 2026, the average monthly cash on cash return in Chaplin is 5.00%. The average monthly rental income in Chaplin is $3,963.

Chaplin, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in Chaplin.

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

The ROI for Long-Term is higher than the Short-Term in Chaplin with average rental income of $3,963.

Your search for investment property begins and ends here

Investment Property for Sale in Chaplin, CT

287 S Bear Hill Road

Chaplin, CT

4 beds | 3 baths | 2,900 sq.ft.

$789,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.1%

Airbnb Rental Income: $null

Traditional Rental Income: $4788

Airbnb ROI: N/A

Traditional ROI: 4.1%

60 Chaplin Street

Chaplin, CT

3 beds | 2 baths | 2,438 sq.ft.

$425,000

Airbnb cash on cash: 1.36%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $2113

Traditional Rental Income: $3138

Airbnb ROI: 1.36%

Traditional ROI: 5.3%

Investment Properties for Sale in Other Cities of Connecticut

Waterbury , CT

3 beds | 2 baths | 1,300 sq.ft.

$339,900

Airbnb cash on cash: -0.12%

Traditional cash on cash: 5.24%

Airbnb Rental Income: $1394

Traditional Rental Income: $2686

Airbnb ROI: -0.12%

Traditional ROI: 5.24%

Waterbury , CT

3 beds | 3 baths | 1,716 sq.ft.

$374,995

Airbnb cash on cash: -0.35%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $1673

Traditional Rental Income: $2715

Airbnb ROI: -0.35%

Traditional ROI: 3.94%

Fairfield , CT

3 beds | 4 baths | 3,328 sq.ft.

$2,399,000

Airbnb cash on cash: -1.79%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $2373

Traditional Rental Income: $5995

Airbnb ROI: -1.79%

Traditional ROI: 0.1%

Canterbury , CT

3 beds | 2 baths | 2,236 sq.ft.

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.03%

Airbnb Rental Income: $null

Traditional Rental Income: $3171

Airbnb ROI: N/A

Traditional ROI: 9.03%

New London , CT

3 beds | 1 baths | 1,311 sq.ft.

$209,900

Airbnb cash on cash: 4.83%

Traditional cash on cash: 7.84%

Airbnb Rental Income: $2087

Traditional Rental Income: $2148

Airbnb ROI: 4.83%

Traditional ROI: 7.84%

Stamford , CT

3 beds | 4 baths | 3,341 sq.ft.

$2,000,000

Airbnb cash on cash: -3.84%

Traditional cash on cash: -1.35%

Airbnb Rental Income: $2038

Traditional Rental Income: $6132

Airbnb ROI: -3.84%

Traditional ROI: -1.35%

Monroe , CT

2 beds | 3 baths | 1,012 sq.ft.

$549,000

Airbnb cash on cash: 0.59%