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 Dr Simsbury, CT This stunning brick Colonial sits atop Hunting Ridge Drive on a sprawling two-acre level l...	4 beds \| 4 baths \| 9,166 sq.ft.	$1,650,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.5% Airbnb Rental Income: $null Traditional Rental Income: $7351 Airbnb ROI: N/A Traditional ROI: 1.5%
14 Billingsgate Dr #14 Simsbury, CT Welcome to Billingsgate, Simsbury's distinguished 55+ community where tranquility and turn...	2 beds \| 2 baths \| 2,729 sq.ft.	$750,000	Airbnb cash on cash: -2.2% Traditional cash on cash: 1.21% Airbnb Rental Income: $1588 Traditional Rental Income: $3522 Airbnb ROI: -2.2% Traditional ROI: 1.21%
15 Sand Hill Rd Simsbury, CT 15 Sand Hill Rd, Simsbury, CT 06089 \| Single Family Residential	8 beds \| 7 baths \| 4,883 sq.ft.	$951,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 5.25% Airbnb Rental Income: $3654 Traditional Rental Income: $7510 Airbnb ROI: -0.01% Traditional ROI: 5.25%
69 Cambridge Ct Simsbury, CT 69 Cambridge Ct, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 2 baths \| 1,740 sq.ft.	$599,900	Airbnb cash on cash: -1.92% Traditional cash on cash: 1.55% Airbnb Rental Income: $1611 Traditional Rental Income: $3100 Airbnb ROI: -1.92% Traditional ROI: 1.55%
2 Quarry Rd Simsbury, CT 2 Quarry Rd, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 2 baths \| 2,432 sq.ft.	$1,195,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.77% Airbnb Rental Income: $null Traditional Rental Income: $3157 Airbnb ROI: N/A Traditional ROI: -0.77%
37 Old Mill Court #37 Simsbury, CT Sun-drenched perfection in this end unit condo and offers the perfect blend of comfort and...	2 beds \| 3 baths \| 1,560 sq.ft.	$319,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 4.34% Airbnb Rental Income: $1588 Traditional Rental Income: $2701 Airbnb ROI: -0.88% Traditional ROI: 4.34%
207 Great Pond Rd Simsbury, CT 207 Great Pond Rd, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 2 baths \| 5,192 sq.ft.	$1,125,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.91% Airbnb Rental Income: $null Traditional Rental Income: $4314 Airbnb ROI: N/A Traditional ROI: 0.91%
1 Partridge Ct #1 Simsbury, CT 1 Partridge Ct #1, Simsbury, CT 06070 \| Condo/Coop	2 beds \| 2 baths \| 1,257 sq.ft.	$299,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 2.01% Airbnb Rental Income: $1588 Traditional Rental Income: $2156 Airbnb ROI: -1.62% Traditional ROI: 2.01%
37 Deer Park Road Simsbury, CT Enjoy the summer in this charming 3-bedroom, 2-bath ranch with inground pool! The main lev...	3 beds \| 2 baths \| 1,862 sq.ft.	$439,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 5.43% Airbnb Rental Income: $1611 Traditional Rental Income: $3348 Airbnb ROI: 0.09% Traditional ROI: 5.43%
19 Westwood Drive Simsbury, CT If Location is what you're after, check out this spacious 1,895 sq ft Cape with 4 bedrooms...	4 beds \| 2 baths \| 1,895 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.62% Airbnb Rental Income: $null Traditional Rental Income: $3530 Airbnb ROI: N/A Traditional ROI: 5.62%
15 Bantry Rd #15 Simsbury, CT 15 Bantry Rd #15, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 3 baths \| 2,528 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.91% Airbnb Rental Income: $null Traditional Rental Income: $4194 Airbnb ROI: N/A Traditional ROI: 0.91%
290 Old Farms Rd Simsbury, CT 290 Old Farms Rd, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 2 baths \| 2,829 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.58% Airbnb Rental Income: $null Traditional Rental Income: $3288 Airbnb ROI: N/A Traditional ROI: 2.58%
23 Berkshire Way Simsbury, CT 23 Berkshire Way, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 2 baths \| 2,212 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $3171 Airbnb ROI: N/A Traditional ROI: 2.15%
276 Stratton Brook Rd Simsbury, CT Step into a time of charm and grace with your own private bed and bath retreat! This one o...	5 beds \| 3 baths \| 3,757 sq.ft.	$799,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 5.7% Airbnb Rental Income: $3654 Traditional Rental Income: $6437 Airbnb ROI: 0.89% Traditional ROI: 5.7%
38 Woodland St Simsbury, CT 38 Woodland St, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 1 baths \| 936 sq.ft.	$259,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 3.15% Airbnb Rental Income: $1611 Traditional Rental Income: $1624 Airbnb ROI: 1.23% Traditional ROI: 3.15%
47 Hayes Road Simsbury, CT Welcome home to this beautifully maintained ranch in one of Simsbury's most sought-after n...	3 beds \| 2 baths \| 1,222 sq.ft.	$368,900	Airbnb cash on cash: 0.45% Traditional cash on cash: 4.73% Airbnb Rental Income: $1611 Traditional Rental Income: $2636 Airbnb ROI: 0.45% Traditional ROI: 4.73%
29 Barry Ln Simsbury, CT 29 Barry Ln, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 1 baths \| 1,077 sq.ft.	$385,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.65% Airbnb Rental Income: $1611 Traditional Rental Income: $1814 Airbnb ROI: -0.18% Traditional ROI: 1.65%
7 Middle Ln Simsbury, CT 7 Middle Ln, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 1 baths \| 1,248 sq.ft.	$350,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.74% Airbnb Rental Income: $1611 Traditional Rental Income: $1866 Airbnb ROI: -0.42% Traditional ROI: 1.74%
36 Woodside Cir Simsbury, CT 36 Woodside Cir, Simsbury, CT 06070 \| Single Family Residential	7 beds \| 3 baths \| 3,232 sq.ft.	$699,900	Airbnb cash on cash: 1.05% Traditional cash on cash: 3.66% Airbnb Rental Income: $3654 Traditional Rental Income: $4583 Airbnb ROI: 1.05% Traditional ROI: 3.66%
7 Nod Brook Dr Simsbury, CT 7 Nod Brook Dr, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 3 baths \| 5,532 sq.ft.	$859,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.06% Airbnb Rental Income: $null Traditional Rental Income: $4316 Airbnb ROI: N/A Traditional ROI: 2.06%
17 Carver Cir Simsbury, CT 17 Carver Cir, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 1 baths \| 1,565 sq.ft.	$450,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 0.67% Airbnb Rental Income: $1611 Traditional Rental Income: $1689 Airbnb ROI: -0.6% Traditional ROI: 0.67%
1 Meadow Ct #1 Simsbury, CT 1 Meadow Ct #1, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 1 baths \| 1,299 sq.ft.	$299,900	Airbnb cash on cash: -0.34% Traditional cash on cash: 11.73% Airbnb Rental Income: $1611 Traditional Rental Income: $4560 Airbnb ROI: -0.34% Traditional ROI: 11.73%
28 Crestwood Rd Simsbury, CT 28 Crestwood Rd, Simsbury, CT 06070 \| Single Family Residential	4 beds \| 2 baths \| 2,165 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.64% Airbnb Rental Income: $null Traditional Rental Income: $3178 Airbnb ROI: N/A Traditional ROI: 1.64%
267 Firetown Rd Simsbury, CT 267 Firetown Rd, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 3 baths \| 1,724 sq.ft.	$424,900	Airbnb cash on cash: -0.46% Traditional cash on cash: 4.54% Airbnb Rental Income: $1611 Traditional Rental Income: $3143 Airbnb ROI: -0.46% Traditional ROI: 4.54%
6 Knoll Ln #6 Simsbury, CT 6 Knoll Ln #6, Simsbury, CT 06089 \| Condo/Coop	1 beds \| 1 baths \| 726 sq.ft.	$170,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.07% Airbnb Rental Income: $1350 Traditional Rental Income: $1330 Airbnb ROI: -0.36% Traditional ROI: 2.07%
8 Valley View Dr Simsbury, CT 8 Valley View Dr, Simsbury, CT 06089 \| Single Family Residential	4 beds \| 2 baths \| 1,792 sq.ft.	$389,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.24% Airbnb Rental Income: $null Traditional Rental Income: $3143 Airbnb ROI: N/A Traditional ROI: 5.24%
21 Watson Dr Simsbury, CT 21 Watson Dr, Simsbury, CT 06092 \| Single Family Residential	4 beds \| 2 baths \| 2,939 sq.ft.	$679,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.53% Airbnb Rental Income: $null Traditional Rental Income: $3040 Airbnb ROI: N/A Traditional ROI: 1.53%
26 Village Rd Simsbury, CT 26 Village Rd, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 2 baths \| 1,922 sq.ft.	$499,900	Airbnb cash on cash: -0.85% Traditional cash on cash: 2.62% Airbnb Rental Income: $1611 Traditional Rental Income: $2775 Airbnb ROI: -0.85% Traditional ROI: 2.62%
86 Simsbury Manor Dr Simsbury, CT 86 Simsbury Manor Dr, Simsbury, CT 06089 \| Single Family Residential	4 beds \| 2 baths \| 2,023 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.58% Airbnb Rental Income: $null Traditional Rental Income: $3040 Airbnb ROI: N/A Traditional ROI: 3.58%
16 Carson Way Simsbury, CT 16 Carson Way, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 2 baths \| 2,035 sq.ft.	$675,000	Airbnb cash on cash: -2.16% Traditional cash on cash: 3.25% Airbnb Rental Income: $1611 Traditional Rental Income: $4560 Airbnb ROI: -2.16% Traditional ROI: 3.25%
30 N Canton Rd Simsbury, CT 30 N Canton Rd, Simsbury, CT 06092 \| Single Family Residential	4 beds \| 2 baths \| 3,366 sq.ft.	$769,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.38% Airbnb Rental Income: $null Traditional Rental Income: $3328 Airbnb ROI: N/A Traditional ROI: 1.38%
Lot 30 Cambridge Ct Simsbury, CT Lot 30 Cambridge Ct, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 2 baths \| 1,450 sq.ft.	$575,000	Airbnb cash on cash: -1.87% Traditional cash on cash: 4.47% Airbnb Rental Income: $1611 Traditional Rental Income: $4560 Airbnb ROI: -1.87% Traditional ROI: 4.47%
Lot 18 Cambridge Ct Simsbury, CT Lot 18 Cambridge Ct, Simsbury, CT 06070 \| Single Family Residential	3 beds \| 2 baths \| 1,759 sq.ft.	$599,999	Airbnb cash on cash: -1.9% Traditional cash on cash: 1.74% Airbnb Rental Income: $1611 Traditional Rental Income: $3160 Airbnb ROI: -1.9% Traditional ROI: 1.74%

Real Estate investment in Simsbury, CT

There are 45 properties for sale in the city of Simsbury . The median list price in Simsbury is $567,500 and the average price per square foot is $243. In August 2026, the average monthly cash on cash return in Simsbury is 3.00%. The average monthly rental income in Simsbury is $3,171.

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

There are 45 investment properties available for sale in Simsbury.

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

The ROI for Short-Term is higher than the Long-Term in Simsbury with average rental income of $1,611.

Your search for investment property begins and ends here

Investment Property for Sale in Simsbury, CT

24 Hunting Ridge Dr

Simsbury, CT

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

$1,650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.5%

Airbnb Rental Income: $null

Traditional Rental Income: $7351

Airbnb ROI: N/A

Traditional ROI: 1.5%

14 Billingsgate Dr #14

Simsbury, CT

2 beds | 2 baths | 2,729 sq.ft.

$750,000

Airbnb cash on cash: -2.2%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $1588

Traditional Rental Income: $3522

Airbnb ROI: -2.2%

Traditional ROI: 1.21%

15 Sand Hill Rd

Simsbury, CT

8 beds | 7 baths | 4,883 sq.ft.

$951,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $3654

Traditional Rental Income: $7510

Airbnb ROI: -0.01%

Traditional ROI: 5.25%

69 Cambridge Ct

Simsbury, CT

3 beds | 2 baths | 1,740 sq.ft.

$599,900

Airbnb cash on cash: -1.92%

Traditional cash on cash: 1.55%

Airbnb Rental Income: $1611

Traditional Rental Income: $3100

Airbnb ROI: -1.92%

Traditional ROI: 1.55%

2 Quarry Rd

Simsbury, CT

4 beds | 2 baths | 2,432 sq.ft.

$1,195,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.77%

Airbnb Rental Income: $null

Traditional Rental Income: $3157

Airbnb ROI: N/A

Traditional ROI: -0.77%

37 Old Mill Court #37

Simsbury, CT

2 beds | 3 baths | 1,560 sq.ft.

$319,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $1588

Traditional Rental Income: $2701

Airbnb ROI: -0.88%

Traditional ROI: 4.34%

207 Great Pond Rd

Simsbury, CT

4 beds | 2 baths | 5,192 sq.ft.

$1,125,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.91%

Airbnb Rental Income: $null

Traditional Rental Income: $4314

Airbnb ROI: N/A

Traditional ROI: 0.91%

1 Partridge Ct #1

Simsbury, CT

2 beds | 2 baths | 1,257 sq.ft.

$299,000

Airbnb cash on cash: -1.62%

Traditional cash on cash: 2.01%

Airbnb Rental Income: $1588

Traditional Rental Income: $2156

Airbnb ROI: -1.62%