Real Estate Investment Properties for Sale in Deep River, CT

Looking for investment property in Deep River, CT with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
38 Main Street Deep River, CT Nestled in the charming town of Deep River, between the villages of Essex and Chester, thi...	4 beds \| 4 baths \| 2,560 sq.ft.	$650,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 7.68% Airbnb Rental Income: $1386 Traditional Rental Income: $6058 Airbnb ROI: -0.71% Traditional ROI: 7.68%
92 Main Street #107 Deep River, CT Step into a loft-style townhouse in the historic Piano Works building that blends vintage ...	1 beds \| 1 baths \| 727 sq.ft.	$212,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 5.3% Airbnb Rental Income: $997 Traditional Rental Income: $1546 Airbnb ROI: 0.8% Traditional ROI: 5.3%
16 Glen Grove Road Deep River, CT 16 Glen Grove Road....a stunning custom built 2023 Colonial privately set on 4.53 acres in...	4 beds \| 3 baths \| 2,782 sq.ft.	$899,900	Airbnb cash on cash: -1.16% Traditional cash on cash: 3.01% Airbnb Rental Income: $1386 Traditional Rental Income: $4455 Airbnb ROI: -1.16% Traditional ROI: 3.01%
177 Union Street Deep River, CT Charm, character, original features and details and the amazing farm porch. This classic a...	3 beds \| 2 baths \| 1,392 sq.ft.	$495,900	Airbnb cash on cash: 1.43% Traditional cash on cash: 3.93% Airbnb Rental Income: $2378 Traditional Rental Income: $2953 Airbnb ROI: 1.43% Traditional ROI: 3.93%
97 Bushy Hill Road Deep River, CT Investors take notice. Ranch-style home located in Deep River with lots of potential. Grea...	3 beds \| 2 baths \| 1,314 sq.ft.	$281,200	Airbnb cash on cash: 3.85% Traditional cash on cash: 7.22% Airbnb Rental Income: $2378 Traditional Rental Income: $2686 Airbnb ROI: 3.85% Traditional ROI: 7.22%
51 Witch Hazel Drive Deep River, CT Welcome to your next chapter at 51 Witch Hazel Drive, a beautifully maintained Cape tucked...	3 beds \| 3 baths \| 2,231 sq.ft.	$650,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 3.54% Airbnb Rental Income: $2378 Traditional Rental Income: $3672 Airbnb ROI: 0.44% Traditional ROI: 3.54%
391 Main Street #308 Deep River, CT Welcome to Unit 308 at Georgetown Woods. This 2 bedroom unit has many upgrades. The first ...	2 beds \| 2 baths \| 1,080 sq.ft.	$250,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 6.73% Airbnb Rental Income: $1859 Traditional Rental Income: $2226 Airbnb ROI: 3.06% Traditional ROI: 6.73%

Real Estate investment in Deep-river, CT

There are 8 properties for sale in the city of Deep River . The median list price in Deep River is $567,450 and the average price per square foot is $322. In June 2026, the average monthly cash on cash return in Deep River is 5.00%. The average monthly rental income in Deep River is $3,236.

Deep-river, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 8 investment properties available for sale in Deep-river.

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

The ROI for Long-Term is higher than the Short-Term in Deep-river with average rental income of $3,236.

Your search for investment property begins and ends here

Investment Property for Sale in Deep River, CT

38 Main Street

Deep River, CT

4 beds | 4 baths | 2,560 sq.ft.

$650,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 7.68%

Airbnb Rental Income: $1386

Traditional Rental Income: $6058

Airbnb ROI: -0.71%

Traditional ROI: 7.68%

92 Main Street #107

Deep River, CT

1 beds | 1 baths | 727 sq.ft.

$212,000

Airbnb cash on cash: 0.8%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $997

Traditional Rental Income: $1546

Airbnb ROI: 0.8%

Traditional ROI: 5.3%

16 Glen Grove Road

Deep River, CT

4 beds | 3 baths | 2,782 sq.ft.

$899,900

Airbnb cash on cash: -1.16%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $1386

Traditional Rental Income: $4455

Airbnb ROI: -1.16%

Traditional ROI: 3.01%

177 Union Street

Deep River, CT

3 beds | 2 baths | 1,392 sq.ft.

$495,900

Airbnb cash on cash: 1.43%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $2378

Traditional Rental Income: $2953

Airbnb ROI: 1.43%

Traditional ROI: 3.93%

97 Bushy Hill Road

Deep River, CT

3 beds | 2 baths | 1,314 sq.ft.

$281,200

Airbnb cash on cash: 3.85%

Traditional cash on cash: 7.22%

Airbnb Rental Income: $2378

Traditional Rental Income: $2686

Airbnb ROI: 3.85%

Traditional ROI: 7.22%

51 Witch Hazel Drive

Deep River, CT

3 beds | 3 baths | 2,231 sq.ft.

$650,000

Airbnb cash on cash: 0.44%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $2378

Traditional Rental Income: $3672

Airbnb ROI: 0.44%

Traditional ROI: 3.54%

391 Main Street #308

Deep River, CT

2 beds | 2 baths | 1,080 sq.ft.

$250,000

Airbnb cash on cash: 3.06%

Traditional cash on cash: 6.73%

Airbnb Rental Income: $1859

Traditional Rental Income: $2226

Airbnb ROI: 3.06%

Traditional ROI: 6.73%

Real Estate investment in Deep-river, CT

Deep-river, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

How many investment properties are available for sale in Deep-river?

Which neighborhoods in Deep-river to invest in 2026?

Long-Term vs. Short-Term Rentals in Deep-river, Connecticut: Which will earn the best returns?

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