Real Estate Investment Properties for Sale in Windsor, CT
Looking for investment property in Windsor, CT with high ROI ?
Explore a variety of short-term homes & houses in Windsor, CT. Invest wisely with VRBO & Windsor, 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 Windsor, CT
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
56 Windbrook DrWindsor, CTThis generous well maintained Colonial home has location, location, location! A welcoming... |
4 beds | 3 baths | 3,118 sq.ft. |
$529,900 |
Airbnb cash on cash: N/A
|
121 E Barber StWindsor, CTClose to many amenities as shops and other places. New flooring, new baths, new cabinets. ... |
2 beds | 1 baths | 924 sq.ft. |
$269,900 |
Airbnb cash on cash: -1.94%
|
63 Pond RoadWindsor, CTTucked away on a quiet, convenient street in Windsor, this updated 3bedroom, 1.5bath raise... |
3 beds | 2 baths | 1,914 sq.ft. |
$374,900 |
Airbnb cash on cash: 0.18%
|
708 Park AvenueWindsor, CTWelcome to 708 Park Ave! This beautifully updated 1,736 sq ft single-family home offers 3 ... |
3 beds | 2 baths | 1,736 sq.ft. |
$375,000 |
Airbnb cash on cash: 0.68%
|
58 Amanda CircleWindsor, CTPRICED TO SELL: MAJOR DISCOUNT & FLEXIBLE PRICING! Seller is relocating out of state and w... |
3 beds | 3 baths | 1,952 sq.ft. |
$449,000 |
Airbnb cash on cash: -0.22%
|
39 Loren CircleWindsor, CTWelcome to this spacious 4-bedroom, 2-bathroom Contemporary home on a cul-de-sac. The open... |
4 beds | 2 baths | 2,402 sq.ft. |
$339,000 |
Airbnb cash on cash: N/A
|
1060 Poquonock AveWindsor, CT1060 Poquonock Ave, Windsor, CT 06095 | Single Family Residential |
4 beds | N/A baths | 1,873 sq.ft. |
$399,000 |
Airbnb cash on cash: N/A
|
318 Capen StWindsor, CT318 Capen St, Windsor, CT 06095 | Single Family Residential |
3 beds | 2 baths | 2,160 sq.ft. |
$599,900 |
Airbnb cash on cash: -1.35%
|
25 Matthew LnWindsor, CT25 Matthew Ln, Windsor, CT 06095 | Other |
N/A beds | N/A baths | N/A |
$289,000 |
Airbnb cash on cash: -3.44%
|
490 Old Day Hill RdWindsor, CT490 Old Day Hill Rd, Windsor, CT 06095 | Other |
N/A beds | N/A baths | N/A |
$325,000 |
Airbnb cash on cash: -3.41%
|
1333 Palisado AveWindsor, CT1333 Palisado Ave, Windsor, CT 06095 | Other |
N/A beds | N/A baths | N/A |
$99,000 |
Airbnb cash on cash: -4.02%
|
0 Walnut and Larch DrWindsor, CT0 Walnut and Larch Dr, Windsor, CT 06095 | Other |
N/A beds | N/A baths | N/A |
$295,000 |
Airbnb cash on cash: -3.44%
|
943 High Path Road #943Windsor, CTRenovated in 2022. Combo LR/DR. Kitchen appliances new in 2022. Primary bedroom with walk-... |
2 beds | 2 baths | 972 sq.ft. |
$199,999 |
Airbnb cash on cash: -4.68%
|
823a Stone RdWindsor, CT823a Stone Rd, Windsor, CT 06095 | Single Family Residential |
4 beds | 2 baths | 2,300 sq.ft. |
$729,000 |
Airbnb cash on cash: N/A
|
28 Skitchewaug StWindsor, CT28 Skitchewaug St, Windsor, CT 06095 | Single Family Residential |
3 beds | 1 baths | 1,472 sq.ft. |
$290,000 |
Airbnb cash on cash: 0.52%
|
30 Parkwood DrWindsor, CT30 Parkwood Dr, Windsor, CT 06095 | Single Family Residential |
5 beds | 2 baths | 2,984 sq.ft. |
$524,900 |
Airbnb cash on cash: -0.03%
|
33 Mechanic Street #210Windsor, CTWelcome to this stunning 2-bedroom, 2-bath expansive ranch-style condo, where dramatic mil... |
2 beds | 2 baths | 1,550 sq.ft. |
$343,500 |
Airbnb cash on cash: -2.59%
|
857 Stone RdWindsor, CT857 Stone Rd, Windsor, CT 06095 | Single Family Residential |
3 beds | 2 baths | 2,100 sq.ft. |
$650,000 |
Airbnb cash on cash: -1.49%
|
158 Colton Street StWindsor, CT158 Colton Street St, Windsor, CT 06095 | Single Family Residential |
2 beds | 1 baths | 1,518 sq.ft. |
$325,000 |
Airbnb cash on cash: -3%
|
24 Valley View DrWindsor, CT24 Valley View Dr, Windsor, CT 06095 | Single Family Residential |
4 beds | 3 baths | 2,280 sq.ft. |
$475,000 |
Airbnb cash on cash: N/A
|
371 Dunfey Lane #371Windsor, CTWelcome to 371 Dunfey Lane in Windsor, CT - a beautifully newly renovated condo that blend... |
3 beds | 3 baths | 2,236 sq.ft. |
$399,900 |
Airbnb cash on cash: 0.05%
|
158 High Path Rd #158Windsor, CT158 High Path Rd #158, Windsor, CT 06095 | Condo/Coop |
2 beds | 2 baths | 1,020 sq.ft. |
$229,900 |
Airbnb cash on cash: -5.59%
|
120 Basswood RdWindsor, CT120 Basswood Rd, Windsor, CT 06095 | Single Family Residential |
4 beds | 2 baths | 2,441 sq.ft. |
$279,000 |
Airbnb cash on cash: N/A
|
18 Chelsea LaneWindsor, CTOpportunity knocks! This spacious colonial sits at the end of the cul-de-sac on a private ... |
3 beds | 3 baths | 1,828 sq.ft. |
$350,000 |
Airbnb cash on cash: 0.08%
|
740 Rainbow RdWindsor, CT740 Rainbow Rd, Windsor, CT 06095 | Single Family Residential |
2 beds | 2 baths | 1,444 sq.ft. |
$289,900 |
Airbnb cash on cash: -2.99%
|
83 Faneuil StWindsor, CT83 Faneuil St, Windsor, CT 06095 | Single Family Residential |
2 beds | 2 baths | 1,165 sq.ft. |
$375,000 |
Airbnb cash on cash: -3.02%
|
914 High Path Rd #914Windsor, CT914 High Path Rd #914, Windsor, CT 06095 | Condo/Coop |
2 beds | 1 baths | 972 sq.ft. |
$215,000 |
Airbnb cash on cash: -5.51%
|
675 Palisado AveWindsor, CT675 Palisado Ave, Windsor, CT 06095 | Single Family Residential |
4 beds | 2 baths | 1,716 sq.ft. |
$425,000 |
Airbnb cash on cash: N/A
|
32 Rhodora Ter #32Windsor, CT32 Rhodora Ter #32, Windsor, CT 06095 | Condo/Coop |
2 beds | 2 baths | 1,536 sq.ft. |
$345,000 |
Airbnb cash on cash: -4.7%
|
141 Rood AveWindsor, CT141 Rood Ave, Windsor, CT 06095 | Single Family Residential |
3 beds | 2 baths | 1,306 sq.ft. |
$369,900 |
Airbnb cash on cash: -0.26%
|
40 Prospect StWindsor, CT40 Prospect St, Windsor, CT 06095 | Multi Family |
6 beds | 2 baths | 2,287 sq.ft. |
$440,000 |
Airbnb cash on cash: -0.71%
|
Real Estate investment in Windsor, CT
There are 38 properties for sale in the city of Windsor . The median list price in Windsor is $600,000 and the average price per square foot is $194. In May 2026, the average monthly cash on cash return in Windsor is 4.00%. The average monthly rental income in Windsor is $2,596.