Real Estate Investment Properties for Sale in Simsbury, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
14 Brettonwood Drive Simsbury, CT FEELING CRAMPED WITH HOLIDAY VISITORS? TAKE A LOOK AT THIS 2/3 BEDROOM 3.5 BATH HOME! Sunl...	2 beds \| 4 baths \| 1,736 sq.ft.	$540,000	Airbnb cash on cash: -2.86% Traditional cash on cash: 4.78% Airbnb Rental Income: $980 Traditional Rental Income: $4482 Airbnb ROI: -2.86% Traditional ROI: 4.78%
10 Woodcliff Dr Simsbury, CT Welcome to 10 Woodcliff! This charming Cape Cod-style home offers a flexible floor plan wi...	4 beds \| 2 baths \| 1,505 sq.ft.	$485,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $3251 Airbnb ROI: N/A Traditional ROI: 4.42%
51 Hendricks Ln Simsbury, CT 51 Hendricks Ln, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 3 baths \| 2,253 sq.ft.	$698,600	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $3952 Airbnb ROI: N/A Traditional ROI: 2.8%
3 Stebbins Brook Ln Simsbury, CT 3 Stebbins Brook Ln, Simsbury, CT 06070 \| Single Family Residential	2 beds \| 1 baths \| 1,056 sq.ft.	$269,900	Airbnb cash on cash: -1.63% Traditional cash on cash: 1.37% Airbnb Rental Income: $980 Traditional Rental Income: $1391 Airbnb ROI: -1.63% Traditional ROI: 1.37%
59 Cambridge Ct Simsbury, CT 59 Cambridge Ct, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 2 baths \| 1,900 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.68% Airbnb Rental Income: $null Traditional Rental Income: $3395 Airbnb ROI: N/A Traditional ROI: 1.68%
Lot 62 Cambridge Ct Simsbury, CT Lot 62 Cambridge Ct, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 2 baths \| 1,500 sq.ft.	$599,000	Airbnb cash on cash: -2.64% Traditional cash on cash: 1.24% Airbnb Rental Income: $1132 Traditional Rental Income: $2922 Airbnb ROI: -2.64% Traditional ROI: 1.24%
Lot 68 Cambridge Ct Simsbury, CT Lot 68 Cambridge Ct, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 3 baths \| 2,800 sq.ft.	$875,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.51% Airbnb Rental Income: $null Traditional Rental Income: $4263 Airbnb ROI: N/A Traditional ROI: 1.51%
9-1/2 E Tomstead Road Simsbury, CT Take a look at this unique ranch style home with open floor plan. Step thru the front door...	2 beds \| 1 baths \| 1,184 sq.ft.	$354,900	Airbnb cash on cash: -1.14% Traditional cash on cash: 2.7% Airbnb Rental Income: $980 Traditional Rental Income: $1907 Airbnb ROI: -1.14% Traditional ROI: 2.7%
60 Barry Ln Simsbury, CT 60 Barry Ln, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 2 baths \| 1,540 sq.ft.	$425,000	Airbnb cash on cash: -1.46% Traditional cash on cash: 3.28% Airbnb Rental Income: $1132 Traditional Rental Income: $2639 Airbnb ROI: -1.46% Traditional ROI: 3.28%
27 Fernwood Dr Simsbury, CT 27 Fernwood Dr, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 2 baths \| 1,821 sq.ft.	$450,000	Airbnb cash on cash: -1.55% Traditional cash on cash: 3.15% Airbnb Rental Income: $1132 Traditional Rental Income: $2736 Airbnb ROI: -1.55% Traditional ROI: 3.15%

Real Estate investment in Simsbury, CT

There are 18 properties for sale in the city of Simsbury . The median list price in Simsbury is $589,000 and the average price per square foot is $237. In February 2026, the average monthly cash on cash return in Simsbury is 3.00%. The average monthly rental income in Simsbury is $3,395.

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

There are 18 investment properties available for sale in Simsbury.

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

The ROI for Long-Term is higher than the Short-Term in Simsbury with average rental income of $3,395.

Your search for investment property begins and ends here

Investment Property for Sale in Simsbury, CT

14 Brettonwood Drive

Simsbury, CT

2 beds | 4 baths | 1,736 sq.ft.

$540,000

Airbnb cash on cash: -2.86%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $980

Traditional Rental Income: $4482

Airbnb ROI: -2.86%

Traditional ROI: 4.78%

10 Woodcliff Dr

Simsbury, CT

4 beds | 2 baths | 1,505 sq.ft.

$485,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.42%

Airbnb Rental Income: $null

Traditional Rental Income: $3251

Airbnb ROI: N/A

Traditional ROI: 4.42%

51 Hendricks Ln

Simsbury, CT

4 beds | 3 baths | 2,253 sq.ft.

$698,600

Airbnb cash on cash: N/A

Traditional cash on cash: 2.8%

Airbnb Rental Income: $null

Traditional Rental Income: $3952

Airbnb ROI: N/A

Traditional ROI: 2.8%

3 Stebbins Brook Ln

Simsbury, CT

2 beds | 1 baths | 1,056 sq.ft.

$269,900

Airbnb cash on cash: -1.63%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $980

Traditional Rental Income: $1391

Airbnb ROI: -1.63%

Traditional ROI: 1.37%

59 Cambridge Ct

Simsbury, CT

4 beds | 2 baths | 1,900 sq.ft.

$650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.68%

Airbnb Rental Income: $null

Traditional Rental Income: $3395

Airbnb ROI: N/A

Traditional ROI: 1.68%

Lot 62 Cambridge Ct

Simsbury, CT

3 beds | 2 baths | 1,500 sq.ft.

$599,000

Airbnb cash on cash: -2.64%

Traditional cash on cash: 1.24%

Airbnb Rental Income: $1132

Traditional Rental Income: $2922

Airbnb ROI: -2.64%

Traditional ROI: 1.24%

Lot 68 Cambridge Ct

Simsbury, CT

4 beds | 3 baths | 2,800 sq.ft.

$875,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.51%

Airbnb Rental Income: $null

Traditional Rental Income: $4263

Airbnb ROI: N/A

Traditional ROI: 1.51%

9-1/2 E Tomstead Road

Simsbury, CT

2 beds | 1 baths | 1,184 sq.ft.

$354,900

Airbnb cash on cash: -1.14%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $980

Traditional Rental Income: $1907

Airbnb ROI: -1.14%