Real Estate Investment Properties for Sale in Cheshire, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
122 Thorn Hollow Road Cheshire, CT Desirable Cheshire Crossing 55+ Community built in 2008. Pristine condition, spacious 2032...	2 beds \| 2 baths \| 2,032 sq.ft.	$519,900	Airbnb cash on cash: 1.17% Traditional cash on cash: 2.77% Airbnb Rental Income: $2934 Traditional Rental Income: $3036 Airbnb ROI: 1.17% Traditional ROI: 2.77%
1135 Waterbury Road #1135 Cheshire, CT Cheshire Townhouse in Move-In condition. New Laminate flooring. Small, quiet, and friendly...	2 beds \| 2 baths \| 1,140 sq.ft.	$249,900	Airbnb cash on cash: 5.78% Traditional cash on cash: 5.5% Airbnb Rental Income: $2934 Traditional Rental Income: $2190 Airbnb ROI: 5.78% Traditional ROI: 5.5%
351-363 South Meriden Road Cheshire, CT Welcome to Hickory Hill Orchards, a stunning New England property in Cheshire, CT, featuri...	4 beds \| 3 baths \| 4,143 sq.ft.	$3,500,000	Airbnb cash on cash: -2.32% Traditional cash on cash: -1.92% Airbnb Rental Income: $3512 Traditional Rental Income: $4014 Airbnb ROI: -2.32% Traditional ROI: -1.92%
60 West Ridge Court Cheshire, CT Welcome to your "New Construction" home - almost complete and ready for you! This stunning...	4 beds \| 4 baths \| 3,315 sq.ft.	$889,900	Airbnb cash on cash: 0.06% Traditional cash on cash: 3.89% Airbnb Rental Income: $3512 Traditional Rental Income: $5906 Airbnb ROI: 0.06% Traditional ROI: 3.89%
0 Whispering Oaks, Lot 5 Court Cheshire, CT Under construction 3,388 SF colonial located at WHISPERING OAKS, Cheshire's newest excepti...	4 beds \| 3 baths \| 3,388 sq.ft.	$989,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 0.74% Airbnb Rental Income: $3512 Traditional Rental Income: $3683 Airbnb ROI: -0.29% Traditional ROI: 0.74%
0 Whispering Oaks, Lot 16 Cheshire, CT This TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi...	5 beds \| 5 baths \| 4,766 sq.ft.	$1,532,822	Airbnb cash on cash: N/A Traditional cash on cash: 0.35% Airbnb Rental Income: $null Traditional Rental Income: $5071 Airbnb ROI: N/A Traditional ROI: 0.35%
0 Whispering Oaks, Lot 10 Cheshire, CT This TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi...	4 beds \| 4 baths \| 3,528 sq.ft.	$1,038,380	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.32% Airbnb Rental Income: $3512 Traditional Rental Income: $4423 Airbnb ROI: -0.42% Traditional ROI: 1.32%
0 Whispering Oaks, Lot 18 Court Cheshire, CT This to-be-built home is located at WHISPERING OAKS, Cheshire's newest exceptional communi...	4 beds \| 3 baths \| 3,430 sq.ft.	$1,002,388	Airbnb cash on cash: -0.32% Traditional cash on cash: 0.66% Airbnb Rental Income: $3512 Traditional Rental Income: $3656 Airbnb ROI: -0.32% Traditional ROI: 0.66%
Lot 5 Bethany Mtn Road Cheshire, CT Stately colonial home to be built in this affluent area of Cheshire. This NEW colonial is ...	4 beds \| 3 baths \| 3,280 sq.ft.	$989,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 0.75% Airbnb Rental Income: $3512 Traditional Rental Income: $3664 Airbnb ROI: -0.25% Traditional ROI: 0.75%
151 Cornwall Avenue Cheshire, CT Historic bungalow cape attributed to the late architect Alice Washburn. Known as the Charl...	3 beds \| 3 baths \| 1,589 sq.ft.	$319,500	Airbnb cash on cash: 5.84% Traditional cash on cash: 6.44% Airbnb Rental Income: $3568 Traditional Rental Income: $2965 Airbnb ROI: 5.84% Traditional ROI: 6.44%
95 Jinny Hill Road Cheshire, CT Stunning custom built 5 bedroom 5 bathroom home where no detail has been overlooked. This ...	5 beds \| 5 baths \| 5,845 sq.ft.	$1,070,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $6169 Airbnb ROI: N/A Traditional ROI: 2.98%
0 Whispering Oaks, Lot 6 Court Cheshire, CT To-be-built home located in Whispering Oaks - Cheshire's newest exceptional community of b...	4 beds \| 3 baths \| 2,745 sq.ft.	$826,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 1.52% Airbnb Rental Income: $3512 Traditional Rental Income: $3694 Airbnb ROI: 0.27% Traditional ROI: 1.52%
205 Jinny Hill Road Cheshire, CT Discover a home where timeless elegance meets innovative design. This stunning residence, ...	5 beds \| 4 baths \| 2,392 sq.ft.	$589,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.45% Airbnb Rental Income: $null Traditional Rental Income: $4815 Airbnb ROI: N/A Traditional ROI: 5.45%
1944 Plank Road Cheshire, CT The most beautiful country setting is home to this 4 bedroom, 1.5 bath Early Traditional c...	4 beds \| 2 baths \| 2,084 sq.ft.	$409,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 5.81% Airbnb Rental Income: $3512 Traditional Rental Income: $3029 Airbnb ROI: 5.05% Traditional ROI: 5.81%
945 Knollwood Circle Cheshire, CT Discover contemporary elegance in this stunning colonial home, perfectly situated on a ser...	3 beds \| 3 baths \| 2,683 sq.ft.	$599,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 3.58% Airbnb Rental Income: $3568 Traditional Rental Income: $3839 Airbnb ROI: 1.69% Traditional ROI: 3.58%
63 Trout Brook Road Cheshire, CT If you are looking for that "special" home to be your family's choice for the holidays, 63...	4 beds \| 3 baths \| 4,178 sq.ft.	$729,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 2.75% Airbnb Rental Income: $3512 Traditional Rental Income: $4122 Airbnb ROI: 0.71% Traditional ROI: 2.75%
8 Currier Way #8 Cheshire, CT Welcome to Currier Woods, a charming family and pet-friendly condominium complex! This del...	2 beds \| 2 baths \| 1,362 sq.ft.	$249,000	Airbnb cash on cash: 5.34% Traditional cash on cash: 6.98% Airbnb Rental Income: $2934 Traditional Rental Income: $2643 Airbnb ROI: 5.34% Traditional ROI: 6.98%
752 Ives Row Cheshire, CT Come home to your private retreat! This spacious property boasts a second-floor in-law sui...	5 beds \| 4 baths \| 3,265 sq.ft.	$730,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.75% Airbnb Rental Income: $null Traditional Rental Income: $6136 Airbnb ROI: N/A Traditional ROI: 5.75%
195 Strathmore Drive Cheshire, CT Beautiful 4 bedroom, 4.5 bath home with contemporary flair will impress with warmth, abund...	4 beds \| 5 baths \| 2,525 sq.ft.	$675,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 5.89% Airbnb Rental Income: $3512 Traditional Rental Income: $5771 Airbnb ROI: 1.08% Traditional ROI: 5.89%
916 Moss Farms Road Cheshire, CT Must See Updated Ready to move in Raised Ranch was fully remodeled in 2016 which included ...	4 beds \| 3 baths \| 2,000 sq.ft.	$499,988	Airbnb cash on cash: 2.53% Traditional cash on cash: 4.59% Airbnb Rental Income: $3512 Traditional Rental Income: $3698 Airbnb ROI: 2.53% Traditional ROI: 4.59%
377 Lincoln Drive Cheshire, CT Beautiful 3 bedroom ranch home in Cheshire. Features stainless kitchen, refinished hardwoo...	3 beds \| 1 baths \| 1,824 sq.ft.	$400,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 3.75% Airbnb Rental Income: $3568 Traditional Rental Income: $2668 Airbnb ROI: 4.06% Traditional ROI: 3.75%
1739 Old Waterbury Road Cheshire, CT Don't miss out on this ranch style home in the desireable community of Cheshire! Three bed...	3 beds \| 1 baths \| 1,200 sq.ft.	$319,900	Airbnb cash on cash: 5.83% Traditional cash on cash: 4.63% Airbnb Rental Income: $3568 Traditional Rental Income: $2422 Airbnb ROI: 5.83% Traditional ROI: 4.63%
40 Strollo Court Cheshire, CT Located in a quiet cul-de-sac neighborhood, this charming 4-bedroom colonial is just 7 yea...	4 beds \| 3 baths \| 2,148 sq.ft.	$649,900	Airbnb cash on cash: 1.21% Traditional cash on cash: 2.64% Airbnb Rental Income: $3512 Traditional Rental Income: $3604 Airbnb ROI: 1.21% Traditional ROI: 2.64%
130 Victoria Drive Cheshire, CT This spectacular home in the multi-award-winning, active adult community 'Castle Heights',...	3 beds \| 3 baths \| 2,605 sq.ft.	$759,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 1.65% Airbnb Rental Income: $3568 Traditional Rental Income: $3857 Airbnb ROI: 0.13% Traditional ROI: 1.65%
29 Pleasant Drive Cheshire, CT Welcome to 29 Pleasant Dr! This beautiful colonial home features a fully remodeled kitchen...	3 beds \| 3 baths \| 1,876 sq.ft.	$539,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 3.59% Airbnb Rental Income: $3568 Traditional Rental Income: $3472 Airbnb ROI: 2.22% Traditional ROI: 3.59%
158 Willow Street Cheshire, CT Discover versatile, modern living at 158 Willow St in Cheshire. This unique property inclu...	6 beds \| 5 baths \| 2,850 sq.ft.	$589,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.73% Airbnb Rental Income: $null Traditional Rental Income: $7726 Airbnb ROI: N/A Traditional ROI: 10.73%
1211 Summit Road Cheshire, CT Welcome to 1211 Summit Rd. This expansive L-shaped ranch is ready to welcome its new owner...	3 beds \| 2 baths \| 1,602 sq.ft.	$419,900	Airbnb cash on cash: 3.72% Traditional cash on cash: 4.43% Airbnb Rental Income: $3568 Traditional Rental Income: $3063 Airbnb ROI: 3.72% Traditional ROI: 4.43%
194 Robin Lane Cheshire, CT This totally remodeled 4 bedroom ranch has so much to give! a very versatile floor plan. T...	4 beds \| 2 baths \| 1,664 sq.ft.	$519,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 3.77% Airbnb Rental Income: $3512 Traditional Rental Income: $3437 Airbnb ROI: 2.33% Traditional ROI: 3.77%

Real Estate investment in Cheshire, CT

There are 28 properties for sale in the city of Cheshire . The median list price in Cheshire is $624,450 and the average price per square foot is $232. In December 2024, the average monthly cash on cash return in Cheshire is 4.00%. The average monthly rental income in Cheshire is $3,689.

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

There are 28 investment properties available for sale in Cheshire.

In 2024, the best neighborhood to buy investment property is Cheshire.

The ROI for Long-Term is higher than the Short-Term in Cheshire with average rental income of $3,689.

Your search for investment property begins and ends here

Investment Property for Sale in Cheshire, CT

122 Thorn Hollow Road

Cheshire, CT

2 beds | 2 baths | 2,032 sq.ft.

$519,900

Airbnb cash on cash: 1.17%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $2934

Traditional Rental Income: $3036

Airbnb ROI: 1.17%

Traditional ROI: 2.77%

1135 Waterbury Road #1135

Cheshire, CT

2 beds | 2 baths | 1,140 sq.ft.

$249,900

Airbnb cash on cash: 5.78%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $2934

Traditional Rental Income: $2190

Airbnb ROI: 5.78%

Traditional ROI: 5.5%

351-363 South Meriden Road

Cheshire, CT

4 beds | 3 baths | 4,143 sq.ft.

$3,500,000

Airbnb cash on cash: -2.32%

Traditional cash on cash: -1.92%

Airbnb Rental Income: $3512

Traditional Rental Income: $4014

Airbnb ROI: -2.32%

Traditional ROI: -1.92%

60 West Ridge Court

Cheshire, CT

4 beds | 4 baths | 3,315 sq.ft.

$889,900

Airbnb cash on cash: 0.06%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $3512

Traditional Rental Income: $5906

Airbnb ROI: 0.06%

Traditional ROI: 3.89%

0 Whispering Oaks, Lot 5 Court

Cheshire, CT

4 beds | 3 baths | 3,388 sq.ft.

$989,900

Airbnb cash on cash: -0.29%

Traditional cash on cash: 0.74%

Airbnb Rental Income: $3512

Traditional Rental Income: $3683

Airbnb ROI: -0.29%

Traditional ROI: 0.74%

0 Whispering Oaks, Lot 16

Cheshire, CT

5 beds | 5 baths | 4,766 sq.ft.

$1,532,822

Airbnb cash on cash: N/A

Traditional cash on cash: 0.35%

Airbnb Rental Income: $null

Traditional Rental Income: $5071

Airbnb ROI: N/A

Traditional ROI: 0.35%

0 Whispering Oaks, Lot 10

Cheshire, CT

4 beds | 4 baths | 3,528 sq.ft.

$1,038,380

Airbnb cash on cash: -0.42%

Traditional cash on cash: 1.32%

Airbnb Rental Income: $3512

Traditional Rental Income: $4423

Airbnb ROI: -0.42%

Traditional ROI: 1.32%

0 Whispering Oaks, Lot 18 Court

Cheshire, CT

4 beds | 3 baths | 3,430 sq.ft.

$1,002,388

Airbnb cash on cash: -0.32%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $3512

Traditional Rental Income: $3656

Airbnb ROI: -0.32%