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
112 Cedar Swamp Road Deep River, CT Welcome to your dream home at 112 Cedar Swamp Road, Deep River, CT! This charming Cape Cod...	4 beds \| 3 baths \| 2,969 sq.ft.	$649,900	Airbnb cash on cash: 0.83% Traditional cash on cash: 4.58% Airbnb Rental Income: $3219 Traditional Rental Income: $4764 Airbnb ROI: 0.83% Traditional ROI: 4.58%
92 West Bridge Street Deep River, CT Investors please take note! This property sits on nearly an acre of land.....A beautiful p...	4 beds \| 2 baths \| 3,316 sq.ft.	$399,900	Airbnb cash on cash: 3.29% Traditional cash on cash: 6.62% Airbnb Rental Income: $3219 Traditional Rental Income: $3745 Airbnb ROI: 3.29% Traditional ROI: 6.62%
32 Pinewood Trail Deep River, CT Set on 3.54 private acres in Winthrop, 32 Pinewood Trail offers a farm-to-table lifestyle ...	4 beds \| 4 baths \| 3,697 sq.ft.	$824,900	Airbnb cash on cash: 0% Traditional cash on cash: 5.87% Airbnb Rental Income: $3219 Traditional Rental Income: $7005 Airbnb ROI: 0% Traditional ROI: 5.87%
46 Hemlock Drive Deep River, CT Charming home located just out of town. Nicely laid out for entertaining in and out. Large...	4 beds \| 2 baths \| 1,688 sq.ft.	$419,900	Airbnb cash on cash: 2.98% Traditional cash on cash: 5.09% Airbnb Rental Income: $3219 Traditional Rental Income: $3321 Airbnb ROI: 2.98% Traditional ROI: 5.09%
168 Main Street Deep River, CT High Income Producing properties. The tenants are responsible for Propane, Electric and Ca...	24 beds \| 3 baths \| 4,180 sq.ft.	$1,700,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.42% Airbnb Rental Income: $null Traditional Rental Income: $4369 Airbnb ROI: N/A Traditional ROI: -0.42%
170 Main Street Deep River, CT The tenants are responsible for Propane, Electric and Cable. Each apartment has its own el...	7 beds \| 5 baths \| 3,461 sq.ft.	$1,700,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.75% Airbnb Rental Income: $null Traditional Rental Income: $7805 Airbnb ROI: N/A Traditional ROI: 1.75%
129 Falls Landing Road Deep River, CT Waterfront Colonial on a cul-de-sac near town and schools. Open floor plan Family room wit...	4 beds \| 3 baths \| 2,550 sq.ft.	$675,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.35% Airbnb Rental Income: $3219 Traditional Rental Income: $4167 Airbnb ROI: 0.69% Traditional ROI: 3.35%
62 RIVER Street Deep River, CT A RARE GEM, WELCOME TO THIS RESTORED VICTORIAN TWO FAMILY HOME DESIGNED FOR EASY LIVING. C...	4 beds \| 2 baths \| 1,970 sq.ft.	$799,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 1.3% Airbnb Rental Income: $3219 Traditional Rental Income: $3388 Airbnb ROI: 0.1% Traditional ROI: 1.3%
347 Main Street Deep River, CT Discover this inviting ranch-style home, perfectly positioned just minutes from the histor...	3 beds \| 2 baths \| 1,248 sq.ft.	$316,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 5.52% Airbnb Rental Income: $2465 Traditional Rental Income: $2660 Airbnb ROI: 2.85% Traditional ROI: 5.52%

Real Estate investment in Deep-river, CT

There are 10 properties for sale in the city of Deep River . The median list price in Deep River is $662,450 and the average price per square foot is $251. In October 2025, the average monthly cash on cash return in Deep River is 4.00%. The average monthly rental income in Deep River is $3,956.

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

There are 10 investment properties available for sale in Deep-river.

In 2025, 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 $3,956.

Your search for investment property begins and ends here

Investment Property for Sale in Deep River, CT

112 Cedar Swamp Road

Deep River, CT

4 beds | 3 baths | 2,969 sq.ft.

$649,900

Airbnb cash on cash: 0.83%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $3219

Traditional Rental Income: $4764

Airbnb ROI: 0.83%

Traditional ROI: 4.58%

92 West Bridge Street

Deep River, CT

4 beds | 2 baths | 3,316 sq.ft.

$399,900

Airbnb cash on cash: 3.29%

Traditional cash on cash: 6.62%

Airbnb Rental Income: $3219

Traditional Rental Income: $3745

Airbnb ROI: 3.29%

Traditional ROI: 6.62%

32 Pinewood Trail

Deep River, CT

4 beds | 4 baths | 3,697 sq.ft.

$824,900

Airbnb cash on cash: 0%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $3219

Traditional Rental Income: $7005

Airbnb ROI: 0%

Traditional ROI: 5.87%

46 Hemlock Drive

Deep River, CT

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

$419,900

Airbnb cash on cash: 2.98%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $3219

Traditional Rental Income: $3321

Airbnb ROI: 2.98%

Traditional ROI: 5.09%

168 Main Street

Deep River, CT

24 beds | 3 baths | 4,180 sq.ft.

$1,700,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.42%

Airbnb Rental Income: $null

Traditional Rental Income: $4369

Airbnb ROI: N/A

Traditional ROI: -0.42%

170 Main Street

Deep River, CT

7 beds | 5 baths | 3,461 sq.ft.

$1,700,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.75%

Airbnb Rental Income: $null

Traditional Rental Income: $7805

Airbnb ROI: N/A

Traditional ROI: 1.75%

129 Falls Landing Road

Deep River, CT

4 beds | 3 baths | 2,550 sq.ft.

$675,000

Airbnb cash on cash: 0.69%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $3219

Traditional Rental Income: $4167

Airbnb ROI: 0.69%

Traditional ROI: 3.35%

62 RIVER Street

Deep River, CT

4 beds | 2 baths | 1,970 sq.ft.

$799,000

Airbnb cash on cash: 0.1%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $3219

Traditional Rental Income: $3388

Airbnb ROI: 0.1%