Real Estate Investment Properties for Sale in Winsted, CT
Looking for investment property in Winsted, CT with high ROI ?
Explore a variety of short-term homes & houses in Winsted, CT. Invest wisely with VRBO & Winsted, 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 Winsted, CT
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
118 South RdWinsted, CTWell cared for Colonial 4 bedroom 3 bath Home.Nice 2.76 acre lot , lightly wooded with a s... |
4 beds | 3 baths | 2,240 sq.ft. |
$419,000 |
Airbnb cash on cash: 2.99%
|
878 W Wakefield BlvdWinsted, CTFantastic waterfront home. 4 bedrooms and a huge family room with wet bar and sliders that... |
4 beds | 3 baths | 3,330 sq.ft. |
$998,000 |
Airbnb cash on cash: 0.18%
|
160 Williams AveWinsted, CTCome see this large 2 family with so much to offer! Zoned for small business. Or make it a... |
6 beds | 3 baths | 3,302 sq.ft. |
$385,000 |
Airbnb cash on cash: 2.15%
|
94 Holabird AveWinsted, CTAdorable 3-4 bedroom Cape. This home has been tastefully updated and will make a cozy home... |
3 beds | 1 baths | 1,422 sq.ft. |
$249,900 |
Airbnb cash on cash: 2.56%
|
132 E Lake StWinsted, CTWelcome to East Lake Street at Highland Lake, where privacy, comfort, and year-round recre... |
3 beds | 2 baths | 1,820 sq.ft. |
$365,000 |
Airbnb cash on cash: 1.11%
|
119 W Wakefield BlvdWinsted, CTThis home and property provide a unique opportunity to own a multi family at Highland Lake... |
4 beds | 2 baths | 1,781 sq.ft. |
$849,900 |
Airbnb cash on cash: 0.74%
|
68 Wetmore AveWinsted, CTExtremely well cared for two family located on a desirable street in Winsted! Plenty of o... |
6 beds | 2 baths | 2,555 sq.ft. |
$349,999 |
Airbnb cash on cash: 4.36%
|
71-73 Wheeler StWinsted, CTA positive income even if you live in one of the units. Two 2 family homes(4 units total) ... |
8 beds | 4 baths | 2,000 sq.ft. |
$450,000 |
Airbnb cash on cash: 3.01%
|
63 Meadow StWinsted, CTBeautiful 3 family home just minutes from Highland Lake. Features new roof, windows, vinyl... |
5 beds | 3 baths | 2,602 sq.ft. |
$345,000 |
Airbnb cash on cash: 4.56%
|
104 Maloney CtWinsted, CTINTERIOR FRESHLY PAINTED, HARDWOOD FLOORS REFINISHED , AND READY FOR NEW FAMILY. THIS THRE... |
3 beds | 1 baths | 1,008 sq.ft. |
$284,000 |
Airbnb cash on cash: 2.18%
|
258 Perch Rock TrlWinsted, CTHighland Lake Direct Waterfront Gem located on a quiet side street on the east side of the... |
4 beds | 2 baths | 1,373 sq.ft. |
$795,000 |
Airbnb cash on cash: 0.7%
|
149 E Mountain AveWinsted, CTAdorable and move in ready single level Cape style home. The first floor features a recent... |
2 beds | 1 baths | 993 sq.ft. |
$274,900 |
Airbnb cash on cash: 1.16%
|
26 Elm StWinsted, CTInvestors take notice? This is your deal. Located in the downtown disctrict next to the ne... |
5 beds | 3 baths | 2,496 sq.ft. |
$398,000 |
Airbnb cash on cash: 0.26%
|
118 Meadow StWinsted, CTThis charming historic home, built in 1860, blends timeless character with thoughtful upda... |
3 beds | 2 baths | 1,652 sq.ft. |
$260,000 |
Airbnb cash on cash: 2.32%
|
77 Hubbard StWinsted, CTDiscover this versatile two-family residence offering a blend of modern updates and timele... |
4 beds | 2 baths | 2,699 sq.ft. |
$359,900 |
Airbnb cash on cash: N/A
|
55 Walnut StWinsted, CTTimeless Victorian with Endless Possibilities.Step into a piece of history with this stunn... |
5 beds | 1 baths | 5,016 sq.ft. |
$410,000 |
Airbnb cash on cash: N/A
|
9 John StWinsted, CTPerfect property for a tiny home enthusiasts looking for easy maintenance-free living. Sma... |
2 beds | 1 baths | 1,172 sq.ft. |
$230,000 |
Airbnb cash on cash: 0.67%
|
441 Platt Hill RdWinsted, CTWelcome to 441 Platt Hill Road - a home that offers warmth, charm, and plenty of space to ... |
5 beds | 3 baths | 3,404 sq.ft. |
$474,900 |
Airbnb cash on cash: N/A
|
720 Main StWinsted, CTPrime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building locate... |
3 beds | 2 baths | 1,909 sq.ft. |
$395,000 |
Airbnb cash on cash: N/A
|
95 Nalette DrWinsted, CTStunning Contemporary Home on a Quiet Corner Lot. This unique home offers a beautifully u... |
3 beds | 2 baths | 2,356 sq.ft. |
$365,000 |
Airbnb cash on cash: 0.15%
|
187 Torringford StWinsted, CT187 Torringford St, Winsted, CT 06098 | Single Family Residential |
4 beds | 1 baths | 2,365 sq.ft. |
$399,000 |
Airbnb cash on cash: 2.46%
|
115 Old Robertsville RdWinsted, CT115 Old Robertsville Rd, Winsted, CT 06098 | Single Family Residential |
5 beds | 1 baths | 2,304 sq.ft. |
$649,900 |
Airbnb cash on cash: N/A
|
469 Platt Hill RdWinsted, CT469 Platt Hill Rd, Winsted, CT 06098 | Single Family Residential |
4 beds | 2 baths | 3,088 sq.ft. |
$895,000 |
Airbnb cash on cash: -0.62%
|
32 Norfolk RdWinsted, CT32 Norfolk Rd, Winsted, CT 06098 | Other |
N/A beds | N/A baths | N/A |
$299,900 |
Airbnb cash on cash: 1.41%
|
7 Stadler HtsWinsted, CT7 Stadler Hts, Winsted, CT 06098 | Other |
N/A beds | N/A baths | N/A |
$389,000 |
Airbnb cash on cash: 0.39%
|
000000 Norfolk RdWinsted, CT000000 Norfolk Rd, Winsted, CT 06098 | Other |
N/A beds | N/A baths | N/A |
$879,990 |
Airbnb cash on cash: -1.57%
|
843-845 (lots - 10A,10 &1 E wakefield BlvdWinsted, CT843-845 (lots - 10A,10 &1 E wakefield Blvd, Winsted, CT 06098 | Other |
N/A beds | N/A baths | N/A |
$158,000 |
Airbnb cash on cash: 5.37%
|
21 Riveredge Dr #21Winsted, CTUpdated 2-bedroom, 1.5-bath condo featuring a renovated kitchen with new appliances (2022)... |
2 beds | 1 baths | 992 sq.ft. |
$170,000 |
Airbnb cash on cash: -0.34%
|
155 Rockwell StWinsted, CT155 Rockwell St, Winsted, CT 06098 | Single Family Residential |
3 beds | 1 baths | 1,317 sq.ft. |
$159,000 |
Airbnb cash on cash: 4.28%
|
230 E Wakefield BlvdWinsted, CT230 E Wakefield Blvd, Winsted, CT 06098 | Single Family Residential |
3 beds | 2 baths | 1,536 sq.ft. |
$314,000 |
Airbnb cash on cash: 0.68%
|
343 E Wakefield BlvdWinsted, CT343 E Wakefield Blvd, Winsted, CT 06098 | Single Family Residential |
2 beds | 1 baths | 1,218 sq.ft. |
$199,000 |
Airbnb cash on cash: 1.25%
|
107 Birdsall StWinsted, CTSpacious colonial with 4 bedrooms, 2 full baths, generous size living room, dining room, s... |
4 beds | 2 baths | 1,874 sq.ft. |
$240,000 |
Airbnb cash on cash: 6.65%
|
95 Colony DrWinsted, CT95 Colony Dr, Winsted, CT 06098 | Single Family Residential |
3 beds | 1 baths | 1,008 sq.ft. |
$285,000 |
Airbnb cash on cash: 1.06%
|
171 Wallens StWinsted, CT171 Wallens St, Winsted, CT 06098 | Single Family Residential |
2 beds | 2 baths | 1,274 sq.ft. |
$359,900 |
Airbnb cash on cash: -0.69%
|
174 Wallens St Apt A5Winsted, CT174 Wallens St Apt A5, Winsted, CT 06098 | Condo/Coop |
2 beds | 2 baths | 1,946 sq.ft. |
$289,000 |
Airbnb cash on cash: -2.09%
|
9 Central AveWinsted, CT9 Central Ave, Winsted, CT 06098 | Single Family Residential |
3 beds | 1 baths | 1,267 sq.ft. |
$274,900 |
Airbnb cash on cash: 1.21%
|
351 Platt Hill RdWinsted, CT351 Platt Hill Rd, Winsted, CT 06098 | Single Family Residential |
3 beds | 2 baths | 1,715 sq.ft. |
$370,000 |
Airbnb cash on cash: 0.11%
|
257-259 Torringford StWinsted, CT257 Torringford St, Winsted, CT 06098 | Other |
N/A beds | N/A baths | N/A |
$799,000 |
Airbnb cash on cash: -1.41%
|
121 W Wakefield BlvdWinsted, CT121 W Wakefield Blvd, Winsted, CT 06098 | Single Family Residential |
4 beds | 3 baths | 2,265 sq.ft. |
$679,000 |
Airbnb cash on cash: 0.17%
|
Real Estate investment in Winsted, CT
There are 73 properties for sale in the city of Winsted . The median list price in Winsted is $319,826 and the average price per square foot is $162. In September 2026, the average monthly cash on cash return in Winsted is 5.00%. The average monthly rental income in Winsted is $2,074.