Real Estate Investments for Sale in Cheshire, CT With High ROI
Are you looking for a vacation rental in Cheshire, CT? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.
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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
34 Alyssa DriveCheshire, CTThis absolutely spectacular home in the multi-award-winning, active adult community âCas... |
3 beds | 4 baths | 3,327 sq.ft. |
$789,900 |
Airbnb cash on cash: 2.2%
|
539 Wiese RoadCheshire, CTWelcome to your charming new home located at 539 Wiese Road. This delightful three bedroom... |
3 beds | 2 baths | 1,456 sq.ft. |
$425,000 |
Airbnb cash on cash: 7.9%
|
20 Judson CourtCheshire, CTWelcome to your new home! This ranch style home has 4 bedrooms, 2.5 baths, and a combined ... |
4 beds | 3 baths | 4,340 sq.ft. |
$670,000 |
Airbnb cash on cash: N/A
|
Lot 2 South Brooksvale RoadCheshire, CTLocated in Cheshire's desirable South end , this new construction home is now being offere... |
4 beds | 3 baths | 2,578 sq.ft. |
$720,800 |
Airbnb cash on cash: N/A
|
654 Mountain RoadCheshire, CTThis Custom built 2876 SF 4 bed 4 bath Colonial with impressive brick front offers an open... |
4 beds | 3 baths | 2,701 sq.ft. |
$689,000 |
Airbnb cash on cash: N/A
|
18 Sierra CourtCheshire, CTLast lot available at West Farms Terrace subdivision.... Sierra Court. This huge 7+ acre l... |
4 beds | 3 baths | 2,720 sq.ft. |
$849,753 |
Airbnb cash on cash: N/A
|
351-363 South Meriden RoadCheshire, CTWelcome 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: N/A
|
0 Whispering Oaks, Lot 4Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
3 beds | 2 baths | 2,234 sq.ft. |
$728,600 |
Airbnb cash on cash: 2.72%
|
0 Whispering Oaks, Lot 17Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
4 beds | 3 baths | 2,649 sq.ft. |
$822,284 |
Airbnb cash on cash: N/A
|
991 South Meriden RoadCheshire, CTYour Lovely New Home is situated on a secluded 1.5 acre lot. Enjoy tranquility and relaxat... |
4 beds | 2 baths | 1,426 sq.ft. |
$449,900 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 13Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
4 beds | 3 baths | 2,915 sq.ft. |
$923,758 |
Airbnb cash on cash: N/A
|
75 Lanyon DriveCheshire, CT***HIGHEST AND BEST DUE AT 2:00PM ON 4/18/24*** The finishing touches have been completed ... |
5 beds | 3 baths | 3,388 sq.ft. |
$609,900 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 20Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
5 beds | 5 baths | 5,155 sq.ft. |
$1,133,475 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 2Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
4 beds | 3 baths | 2,602 sq.ft. |
$771,325 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 15Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
4 beds | 3 baths | 2,932 sq.ft. |
$928,000 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 3Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
4 beds | 4 baths | 2,881 sq.ft. |
$835,900 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 7Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
4 beds | 3 baths | 2,724 sq.ft. |
$852,776 |
Airbnb cash on cash: N/A
|
367 Wallingford RoadCheshire, CTEASY LIVING in this expanded cape offering 2,587 SF of living space! Feel welcomed the mom... |
4 beds | 3 baths | 2,587 sq.ft. |
$599,900 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 12Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
4 beds | 3 baths | 3,596 sq.ft. |
$1,008,000 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 5 CourtCheshire, CTUnder 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: N/A
|
1161 Sperry RoadCheshire, CTThe Edward Tufte House, elegant, gracious, modern, and a home for 47 years of creative wor... |
3 beds | 5 baths | 8,558 sq.ft. |
$2,000,000 |
Airbnb cash on cash: -0.98%
|
272 Academy RoadCheshire, CTSituated in a highly sought-after location, this home enjoys the prestigious backdrop of C... |
5 beds | 1 baths | 1,954 sq.ft. |
$385,000 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 19Cheshire, CTThis TO-BE-BUILT home is located at WHISPERING OAKS, Cheshire's newest exceptional communi... |
4 beds | 3 baths | 3,321 sq.ft. |
$970,249 |
Airbnb cash on cash: N/A
|
0 Whispering Oaks, Lot 16Cheshire, CTThis 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
|
67 Fernwood LaneCheshire, CTRemodeled Three-bedroom Cozy Ranch with finished walkout basement, house was gutted to stu... |
3 beds | 2 baths | 1,960 sq.ft. |
$394,900 |
Airbnb cash on cash: 7.68%
|
0 Whispering Oaks, Lot 10Cheshire, CTThis 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: N/A
|
140 Chipman DriveCheshire, CTThis home is a WOW!!! Immediately take in the open floor upon entering this ranch style su... |
4 beds | 2 baths | 2,088 sq.ft. |
$499,900 |
Airbnb cash on cash: N/A
|
275 Fenn RoadCheshire, CTGenerate monthly rental income! Discover your private oasis on this expansive 1.84 oasis, ... |
4 beds | 4 baths | 2,327 sq.ft. |
$649,900 |
Airbnb cash on cash: N/A
|
272 Oak AvenueCheshire, CTNestled in the heart of Cheshire, this property offers a tranquil retreat with unmatched c... |
3 beds | 2 baths | 1,621 sq.ft. |
$440,000 |
Airbnb cash on cash: 6.58%
|
689 South Meriden RoadCheshire, CTStep back in time...This beautifully maintained 4 bedroom colonial, set on 3/4 of an acre ... |
4 beds | 2 baths | 2,548 sq.ft. |
$399,900 |
Airbnb cash on cash: N/A
|
367 Spruce StreetCheshire, CTThis fabulous colonial in a friendly neighborhood w/sidewalks greets you with its beautifu... |
4 beds | 3 baths | 2,376 sq.ft. |
$685,000 |
Airbnb cash on cash: N/A
|
65 Royalwood CourtCheshire, CTStep into your dream home, where you are greeted by the inviting front porch of this stunn... |
4 beds | 3 baths | 2,520 sq.ft. |
$519,900 |
Airbnb cash on cash: N/A
|
370 Taylor AvenueCheshire, CTMove into your updated home today! Don't delay, inquire immediately through your agent to ... |
3 beds | 1 baths | 1,538 sq.ft. |
$359,000 |
Airbnb cash on cash: 8.75%
|
39 Green Hill LaneCheshire, CTThis meticulously maintained ranch-style home offers comfortable one-floor living in the h... |
3 beds | 2 baths | 1,656 sq.ft. |
$359,900 |
Airbnb cash on cash: 8.72%
|
18 Blueberry PlaceCheshire, CTWelcome to 18 Blueberry Place, nestled on a peaceful quiet cul-de-sac, this charming one-l... |
3 beds | 1 baths | 1,502 sq.ft. |
$395,000 |
Airbnb cash on cash: 7.68%
|
144 Fairway Drive #144Cheshire, CTWonderfully cared for 2 bedroom, 1 1/2 bath unit available in rarely available Country Vil... |
2 beds | 2 baths | 1,052 sq.ft. |
$257,900 |
Airbnb cash on cash: -4.25%
|
1110 Notch RoadCheshire, CTWelcome to this well cared for ranch in West Cheshire. This home has 3 bedrooms option for... |
3 beds | 2 baths | 1,305 sq.ft. |
$399,900 |
Airbnb cash on cash: 7.55%
|
26 Westmore RoadCheshire, CTMust See- adorable, updated Ranch in Cheshire. This home has it all. Fantastic features in... |
2 beds | 1 baths | 1,272 sq.ft. |
$314,900 |
Airbnb cash on cash: -2.7%
|
Real Estate investment in Cheshire, CT
There are 38 properties for sale in the city of Cheshire . The median list price in Cheshire is $685,000 and the average price per square foot is $249. In April 2024, the average monthly cash on cash return in Cheshire is 3.00%. The average monthly rental income in Cheshire is $3,564.