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
24 Hunting Ridge Drive Simsbury, CT This stunning brick Colonial sits atop Hunting Ridge Drive on a sprawling two-acre level l...	4 beds \| 6 baths \| 9,166 sq.ft.	$1,699,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.61% Airbnb Rental Income: $null Traditional Rental Income: $7351 Airbnb ROI: N/A Traditional ROI: 1.61%
308 Hopmeadow Street Simsbury, CT Welcome home to this amazing property! 3+Br, 3.5Bath, on 8.52 acres ( manicured, landscape...	3 beds \| 4 baths \| 2,346 sq.ft.	$764,900	Airbnb cash on cash: -2.67% Traditional cash on cash: 5% Airbnb Rental Income: $731 Traditional Rental Income: $5888 Airbnb ROI: -2.67% Traditional ROI: 5%
14 Brettonwood Drive Simsbury, CT Sunlit spaces and fantastic flexible floor plan! EASY LIVING in this PRISTINE, updated 2/3...	2 beds \| 4 baths \| 1,736 sq.ft.	$540,000	Airbnb cash on cash: -1.94% Traditional cash on cash: 4.31% Airbnb Rental Income: $1818 Traditional Rental Income: $4482 Airbnb ROI: -1.94% Traditional ROI: 4.31%
324 Firetown Road Simsbury, CT Unique Opportunity in the Heart of Simsbury - 4 Bedroom, 2.5 Bath Colonial on 8.5 Acres. N...	4 beds \| 3 baths \| 2,024 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.04% Airbnb Rental Income: $null Traditional Rental Income: $3904 Airbnb ROI: N/A Traditional ROI: 5.04%
Investment Properties for Sale in Other Cities of Connecticut
23 Heaton Street Waterbury , CT Welcome to this inviting 3-bedroom, 3-bathroom home offering 1,716 sq ft of living space i...	3 beds \| 3 baths \| 1,716 sq.ft.	$374,995	Airbnb cash on cash: 0.17% Traditional cash on cash: 4.46% Airbnb Rental Income: $1673 Traditional Rental Income: $2715 Airbnb ROI: 0.17% Traditional ROI: 4.46%
2 Elmwood Drive #2 Fairfield , CT Rare offering in the coveted Southport Green complex, just steps from Southport Village an...	3 beds \| 4 baths \| 3,328 sq.ft.	$2,495,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.29% Airbnb Rental Income: $2373 Traditional Rental Income: $5995 Airbnb ROI: -1.53% Traditional ROI: 0.29%
360 North 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: 8.76% Airbnb Rental Income: $null Traditional Rental Income: $3171 Airbnb ROI: N/A Traditional ROI: 8.76%
147 Holly Hill Lane Greenwich , CT Prime opportunity to acquire a turn-key investment property featuring 9 duplex-style townh...	2 beds \| 2 baths \| 1,611 sq.ft.	$9,999,999	Airbnb cash on cash: -3.02% Traditional cash on cash: -2.78% Airbnb Rental Income: $1642 Traditional Rental Income: $3419 Airbnb ROI: -3.02% Traditional ROI: -2.78%
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%
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%
38 Aspinall Drive Andover , CT Charming & Quaint New England 3 BR Cape Cod at end of Cul-de-Sac is steps away from Hop Ri...	3 beds \| 1 baths \| 1,008 sq.ft.	$285,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 5.26% Airbnb Rental Income: $1880 Traditional Rental Income: $2075 Airbnb ROI: 2.66% Traditional ROI: 5.26%
114 Terrill Road Stratford , CT Welcome to this charming Paradise Green Ranch, perfectly situated within walking distance ...	3 beds \| 2 baths \| 1,922 sq.ft.	$424,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 5.92% Airbnb Rental Income: $2065 Traditional Rental Income: $3394 Airbnb ROI: 1.24% Traditional ROI: 5.92%
28 Hillside Drive Easton , CT Don't miss this incredible home set on an expansive one-plus-acre property in Lower Easton...	4 beds \| 5 baths \| 4,780 sq.ft.	$1,200,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 6.12% Airbnb Rental Income: $4891 Traditional Rental Income: $9165 Airbnb ROI: 1.39% Traditional ROI: 6.12%
109 Timber Trail Tolland , CT Welcome to 109 Timber Trail in Tolland! This beautiful 4-bedroom, 3-bath home combines tho...	4 beds \| 3 baths \| 2,884 sq.ft.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.89% Airbnb Rental Income: $null Traditional Rental Income: $4437 Airbnb ROI: N/A Traditional ROI: 8.89%
8 Bobcat Lane Warren , CT Perfectly positioned to capture breathtaking sunset views, this beautifully updated four-b...	4 beds \| 5 baths \| 5,537 sq.ft.	$1,985,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.35% Airbnb Rental Income: $3651 Traditional Rental Income: $8633 Airbnb ROI: 0.21% Traditional ROI: 3.35%

Real Estate investment in Simsbury, CT

There are 4 properties for sale in the city of Simsbury . The median list price in Simsbury is $540,000 and the average price per square foot is $152. In December 2025, the average monthly cash on cash return in Simsbury is 5.00%. The average monthly rental income in Simsbury is $4,691.

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

There are 4 investment properties available for sale in Simsbury.

In 2025, 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 $4,691.

Your search for investment property begins and ends here

Investment Property for Sale in Simsbury, CT

24 Hunting Ridge Drive

Simsbury, CT

4 beds | 6 baths | 9,166 sq.ft.

$1,699,999

Airbnb cash on cash: N/A

Traditional cash on cash: 1.61%

Airbnb Rental Income: $null

Traditional Rental Income: $7351

Airbnb ROI: N/A

Traditional ROI: 1.61%

308 Hopmeadow Street

Simsbury, CT

3 beds | 4 baths | 2,346 sq.ft.

$764,900

Airbnb cash on cash: -2.67%

Traditional cash on cash: 5%

Airbnb Rental Income: $731

Traditional Rental Income: $5888

Airbnb ROI: -2.67%

Traditional ROI: 5%

14 Brettonwood Drive

Simsbury, CT

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

$540,000

Airbnb cash on cash: -1.94%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $1818

Traditional Rental Income: $4482

Airbnb ROI: -1.94%

Traditional ROI: 4.31%

324 Firetown Road

Simsbury, CT

4 beds | 3 baths | 2,024 sq.ft.

$499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.04%

Airbnb Rental Income: $null

Traditional Rental Income: $3904

Airbnb ROI: N/A

Traditional ROI: 5.04%

Investment Properties for Sale in Other Cities of Connecticut

Waterbury , CT

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

$374,995

Airbnb cash on cash: 0.17%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $1673

Traditional Rental Income: $2715

Airbnb ROI: 0.17%

Traditional ROI: 4.46%

Fairfield , CT

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

$2,495,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $2373

Traditional Rental Income: $5995

Airbnb ROI: -1.53%

Traditional ROI: 0.29%

Canterbury , CT

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

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.76%

Airbnb Rental Income: $null

Traditional Rental Income: $3171

Airbnb ROI: N/A

Traditional ROI: 8.76%

Greenwich , CT

2 beds | 2 baths | 1,611 sq.ft.

$9,999,999

Airbnb cash on cash: -3.02%

Traditional cash on cash: -2.78%

Airbnb Rental Income: $1642

Traditional Rental Income: $3419

Airbnb ROI: -3.02%

Traditional ROI: -2.78%

Stafford Springs , CT

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