Real Estate Investment Properties for Sale in Woodbury, CT
Looking for investment property in Woodbury, CT with high ROI ?
Explore a variety of short-term homes & houses in Woodbury, CT. Invest wisely with VRBO & Woodbury, 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 Woodbury, CT
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
225 Old Sherman Hill RoadWoodbury, CTDiscover refined country living in this remarkable Woodbury estate set on 33.98 private ac... |
4 beds | 5 baths | 4,517 sq.ft. |
$1,998,000 |
Airbnb cash on cash: N/A
|
54 Mountain RoadWoodbury, CTInvestors take note! 54 Mountain Road, Woodbury, CT This home is truly a diamond in the ... |
2 beds | 1 baths | 1,080 sq.ft. |
$339,000 |
Airbnb cash on cash: 4.83%
|
45 North Gate RoadWoodbury, CTWelcome to Woodbury, a quintessential New England town. This house is located in a very de... |
4 beds | 3 baths | 3,545 sq.ft. |
$1,100,000 |
Airbnb cash on cash: N/A
|
105 Minortown RoadWoodbury, CTNEW PRICE! Don't wait! This ranch-style home might be the perfect fit! Just minutes from t... |
3 beds | 3 baths | 2,227 sq.ft. |
$599,000 |
Airbnb cash on cash: -1.23%
|
25 Curtiss MeadowsWoodbury, CTLive your best life in Woodbury, CT, where charm, history, and natural beauty intertwine! ... |
4 beds | 4 baths | 3,113 sq.ft. |
$974,900 |
Airbnb cash on cash: N/A
|
2 Linden RoadWoodbury, CTCalling All Investors! Opportunity knocks with this spacious corner lot duplex offering gr... |
5 beds | 2 baths | 2,760 sq.ft. |
$365,000 |
Airbnb cash on cash: 2.65%
|
24 Roxbury RoadWoodbury, CTTucked away in the picturesque hills of Litchfield County, right on the desirable Woodbury... |
3 beds | 3 baths | 4,012 sq.ft. |
$1,149,000 |
Airbnb cash on cash: -2.14%
|
2 Judd Hill RoadWoodbury, CTCharm and modern comfort come together in this beautifully renovated 3BR, 2BA home set on ... |
3 beds | 2 baths | 1,470 sq.ft. |
$569,000 |
Airbnb cash on cash: -1.13%
|
819 Main Street NorthWoodbury, CTOpen Meadow Farm, a beautifully maintained property offering a blend of rural charm and mo... |
3 beds | 3 baths | 2,992 sq.ft. |
$1,925,000 |
Airbnb cash on cash: -2.54%
|
360 Old Sherman Hill RoadWoodbury, CTCome view this charming 3 bedroom, 2 full bath, single family home in beautiful Woodbury! ... |
3 beds | 2 baths | 1,296 sq.ft. |
$529,000 |
Airbnb cash on cash: -0.98%
|
4 Fox Run #4Woodbury, CTWelcome to this beautifully refreshed townhome in the highly desirable Woodlake Condominiu... |
2 beds | 2 baths | 1,182 sq.ft. |
$299,990 |
Airbnb cash on cash: 4.44%
|
Real Estate investment in Woodbury, CT
There are 14 properties for sale in the city of Woodbury . The median list price in Woodbury is $584,000 and the average price per square foot is $240. In December 2025, the average monthly cash on cash return in Woodbury is 3.00%. The average monthly rental income in Woodbury is $3,967.