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 |
|---|---|---|---|
557 Upper Grassy Hill RoadWoodbury, CTWelcome to Upper Grassy Hill Living! |
4 beds | 4 baths | 3,784 sq.ft. |
$915,000 |
Airbnb cash on cash: N/A
|
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, CTMuch of the interior of this home is complete. There is still work to be done on the exter... |
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%
|
229 Bacon Pond Road #APT 113Woodbury, CTWelcome to 229 Bacon Pond Road, Unit 113, a spacious end-unit 2-bedroom, 1-bath condo in o... |
2 beds | 1 baths | 913 sq.ft. |
$165,000 |
Airbnb cash on cash: 9.45%
|
393 Middle Road TurnpikeWoodbury, CTThe Tomlinson House, built in 1786, offers a rare chance to own a piece of Woodbury's hist... |
4 beds | 4 baths | 3,280 sq.ft. |
$895,000 |
Airbnb cash on cash: N/A
|
437 Middle Road TurnpikeWoodbury, CTWelcome to this well-positioned hidden gem, perfectly situated in one of the area's most d... |
3 beds | 2 baths | 1,144 sq.ft. |
$375,000 |
Airbnb cash on cash: -0.1%
|
14 Mountain RoadWoodbury, CTWonderful Ca 1840's Colonial on 3 acres with wrap around porch. In the heart of Woodbury, ... |
4 beds | 2 baths | 2,187 sq.ft. |
$649,000 |
Airbnb cash on cash: N/A
|
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. |
$1,275,000 |
Airbnb cash on cash: -2.23%
|
Real Estate investment in Woodbury, CT
There are 14 properties for sale in the city of Woodbury . The median list price in Woodbury is $772,000 and the average price per square foot is $283. In October 2025, the average monthly cash on cash return in Woodbury is 3.00%. The average monthly rental income in Woodbury is $3,967.