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. |
$895,000 |
Airbnb cash on cash: -2.05%
|
54 Mountain RoadWoodbury, CTWelcome to the Historic town of Woodbury! Don't miss the opportunity to own this beautiful... |
3 beds | 1 baths | 1,089 sq.ft. |
$325,000 |
Airbnb cash on cash: 1.63%
|
45 N 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: -1.7%
|
382 Weekeepeemee RoadWoodbury, CTThe Jesse Peck Lambert Homestead, built in 1805 & thoughtfully restored, provides a seamle... |
4 beds | 4 baths | 3,551 sq.ft. |
$2,195,000 |
Airbnb cash on cash: -1.35%
|
819 Main Street NWoodbury, CTOpen Meadow Farm, a beautifully maintained property offering a blend of rural charm and mo... |
3 beds | 3 baths | 2,992 sq.ft. |
$1,675,000 |
Airbnb cash on cash: -0.95%
|
360 Old Sherman Hill RoadWoodbury, CTCome view this charming 3 bedroom, 2 full bath, single family home in beautiful Woodbury! ... |
3 beds | 1 baths | 1,296 sq.ft. |
$399,000 |
Airbnb cash on cash: 0.94%
|
126 Sherman Hill Road #Apt B12Woodbury, CTThis second level unit offers a living and dining combo, kitchen, two bedrooms and one ful... |
2 beds | 1 baths | 1,150 sq.ft. |
$200,000 |
Airbnb cash on cash: -2.49%
|
13 Park LaneWoodbury, CTSet on a picturesque lot with mature landscaping and gorgeous outdoor spaces, this beautif... |
3 beds | 3 baths | 2,264 sq.ft. |
$649,900 |
Airbnb cash on cash: 0%
|
54 Clubhouse Drive #54Woodbury, CTWelcome to this light-filled and beautifully maintained townhome in the highly sought-afte... |
2 beds | 3 baths | 1,916 sq.ft. |
$299,000 |
Airbnb cash on cash: -0.9%
|
40 Church StreetWoodbury, CTHighest and Best by 04/07 at 5:00pm. Beautiful 3-bedroom, 2-bath home located in the heart... |
3 beds | 2 baths | 1,716 sq.ft. |
$419,000 |
Airbnb cash on cash: 0.67%
|
49 Scuppo RoadWoodbury, CTDiscover this beautifully updated ranch-style home ideally situated on over an acre of lev... |
3 beds | 2 baths | 2,292 sq.ft. |
$549,000 |
Airbnb cash on cash: 0.14%
|
30 Hollow RoadWoodbury, CTStep through the doors of history and into one of Connecticut's most treasured colonial re... |
5 beds | 5 baths | 4,884 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -1.17%
|
17 Carriage LaneWoodbury, CTCenter Hall Colonial with Full In-Law! This majestic brick facing home flaunts its locatio... |
5 beds | 4 baths | 3,607 sq.ft. |
$799,900 |
Airbnb cash on cash: -1.11%
|
Real Estate investment in Woodbury, CT
There are 17 properties for sale in the city of Woodbury . The median list price in Woodbury is $399,000 and the average price per square foot is $170. In May 2026, the average monthly cash on cash return in Woodbury is 4.00%. The average monthly rental income in Woodbury is $3,255.