Real Estate Investment Properties for Sale in Sherman, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5 Upland Pastures Road Sherman, CT A striking blend of modern design and timeless barn-inspired architecture, this exceptiona...	5 beds \| 5 baths \| 4,250 sq.ft.	$1,999,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 2.27% Airbnb Rental Income: $3213 Traditional Rental Income: $7758 Airbnb ROI: -0.57% Traditional ROI: 2.27%
8 Taber Lot 1 Road Sherman, CT Taber Acres 3 lot subdivision is offering the last lot available, and this is the building...	2 beds \| 2 baths \| 2,500 sq.ft.	$1,999,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 0.47% Airbnb Rental Income: $2334 Traditional Rental Income: $3123 Airbnb ROI: -0.27% Traditional ROI: 0.47%
Investment Properties for Sale in Other Cities of Connecticut
95 Audubon Street #339 New Haven , CT Rare find: a single level, 2 bedroom, 2 bathroom ~1400 sq.ft. unit located at a desirable ...	2 beds \| 2 baths \| 1,395 sq.ft.	$620,000	Airbnb cash on cash: -3.08% Traditional cash on cash: 0.13% Airbnb Rental Income: $1153 Traditional Rental Income: $2627 Airbnb ROI: -3.08% Traditional ROI: 0.13%
2 Elmwood Drive #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.	$2,200,000	Airbnb cash on cash: -2.01% Traditional cash on cash: 0.19% Airbnb Rental Income: $2023 Traditional Rental Income: $5995 Airbnb ROI: -2.01% Traditional ROI: 0.19%
88 Churchill Road Hamden , CT Graciously set on a quiet street in the heart of Spring Glen, this home seamlessly blends ...	4 beds \| 3 baths \| 2,496 sq.ft.	$675,000	Airbnb cash on cash: -2.24% Traditional cash on cash: 3.45% Airbnb Rental Income: $1195 Traditional Rental Income: $4390 Airbnb ROI: -2.24% Traditional ROI: 3.45%
835 Monroe Turnpike Monroe , CT 835 Monroe Turnpike Set on 4.8 acres of level, private land in Monroe's sought-after Histo...	4 beds \| 4 baths \| 3,826 sq.ft.	$795,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 5.55% Airbnb Rental Income: $1792 Traditional Rental Income: $6522 Airbnb ROI: -1.5% Traditional ROI: 5.55%
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.	$169,900	Airbnb cash on cash: 6.06% Traditional cash on cash: 11.43% Airbnb Rental Income: $1940 Traditional Rental Income: $2298 Airbnb ROI: 6.06% Traditional ROI: 11.43%
56 West Street Bolton , CT Beautifully renovated and move-in ready, 56 West Street offers the space, setting, and upd...	4 beds \| 2 baths \| 2,372 sq.ft.	$559,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 4.25% Airbnb Rental Income: $3417 Traditional Rental Income: $3600 Airbnb ROI: 2.45% Traditional ROI: 4.25%
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%
55 Waterford Lane #2 Stamford , CT Turnkey townhouse living with the space, storage, and private outdoor area rarely found in...	3 beds \| 3 baths \| 1,625 sq.ft.	$775,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 2.56% Airbnb Rental Income: $2528 Traditional Rental Income: $3448 Airbnb ROI: 0.45% Traditional ROI: 2.56%
53 Prospect Street Woodstock , CT Highest and Best Deadline, WEDNESDAY 4/29 at NOON East Woodstock Sweet Escape - Where...	3 beds \| 3 baths \| 1,736 sq.ft.	$425,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 6.23% Airbnb Rental Income: $2119 Traditional Rental Income: $3442 Airbnb ROI: 1.55% Traditional ROI: 6.23%
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: -0.63% Traditional cash on cash: 3.54% Airbnb Rental Income: $1188 Traditional Rental Income: $2560 Airbnb ROI: -0.63% Traditional ROI: 3.54%

Real Estate investment in Sherman, CT

There are 2 properties for sale in the city of Sherman . The median list price in Sherman is $315,000 and the average price per square foot is $142. In May 2026, the average monthly cash on cash return in Sherman is 4.00%. The average monthly rental income in Sherman is $4,438.

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

There are 2 investment properties available for sale in Sherman.

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

The ROI for Short-Term is higher than the Long-Term in Sherman with average rental income of $2,189.

Your search for investment property begins and ends here

Investment Property for Sale in Sherman, CT

5 Upland Pastures Road

Sherman, CT

5 beds | 5 baths | 4,250 sq.ft.

$1,999,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 2.27%

Airbnb Rental Income: $3213

Traditional Rental Income: $7758

Airbnb ROI: -0.57%

Traditional ROI: 2.27%

8 Taber Lot 1 Road

Sherman, CT

2 beds | 2 baths | 2,500 sq.ft.

$1,999,000

Airbnb cash on cash: -0.27%

Traditional cash on cash: 0.47%

Airbnb Rental Income: $2334

Traditional Rental Income: $3123

Airbnb ROI: -0.27%

Traditional ROI: 0.47%

Investment Properties for Sale in Other Cities of Connecticut

New Haven , CT

2 beds | 2 baths | 1,395 sq.ft.

$620,000

Airbnb cash on cash: -3.08%

Traditional cash on cash: 0.13%

Airbnb Rental Income: $1153

Traditional Rental Income: $2627

Airbnb ROI: -3.08%

Traditional ROI: 0.13%

Fairfield , CT

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

$2,200,000

Airbnb cash on cash: -2.01%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $2023

Traditional Rental Income: $5995

Airbnb ROI: -2.01%

Traditional ROI: 0.19%

Hamden , CT

4 beds | 3 baths | 2,496 sq.ft.

$675,000

Airbnb cash on cash: -2.24%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $1195

Traditional Rental Income: $4390

Airbnb ROI: -2.24%

Traditional ROI: 3.45%

Monroe , CT

4 beds | 4 baths | 3,826 sq.ft.

$795,000

Airbnb cash on cash: -1.5%

Traditional cash on cash: 5.55%

Airbnb Rental Income: $1792

Traditional Rental Income: $6522

Airbnb ROI: -1.5%

Traditional ROI: 5.55%

Ledyard , CT

4 beds | 1 baths | 1,260 sq.ft.

$169,900

Airbnb cash on cash: 6.06%

Traditional cash on cash: 11.43%

Airbnb Rental Income: $1940

Traditional Rental Income: $2298

Airbnb ROI: 6.06%

Traditional ROI: 11.43%

Bolton , CT

4 beds | 2 baths | 2,372 sq.ft.

$559,000

Airbnb cash on cash: 2.45%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $3417

Traditional Rental Income: $3600

Airbnb ROI: 2.45%

Traditional ROI: 4.25%

Stafford Springs , CT

3 beds | 2 baths | 1,047 sq.ft.

$349,900

Airbnb cash on cash: N/A