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 |
|---|---|---|---|
34 Quail Run RoadWoodbury, CTSet in a peaceful Woodbury neighborhood, 34 Quail Run blends extensive renovations with co... |
5 beds | 4 baths | 3,657 sq.ft. |
$849,900 |
Airbnb cash on cash: 0.89%
|
253 Bacon Pond RoadWoodbury, CTWelcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury... |
4 beds | 3 baths | 2,283 sq.ft. |
$895,000 |
Airbnb cash on cash: -2.13%
|
67 Flanders RoadWoodbury, CTWelcome to this stunning, fully remodeled Colonial in Woodbury, located in beautiful Litch... |
4 beds | 4 baths | 3,528 sq.ft. |
$634,900 |
Airbnb cash on cash: -2.48%
|
16 Gate Post LaneWoodbury, CTSpacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of li... |
4 beds | 4 baths | 4,491 sq.ft. |
$1,100,000 |
Airbnb cash on cash: -2.39%
|
24 Roxbury RoadWoodbury, CTPrivate Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of... |
3 beds | 3 baths | 4,012 sq.ft. |
$1,149,000 |
Airbnb cash on cash: -0.6%
|
92 Minortown RoadWoodbury, CTLive Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country li... |
3 beds | 2 baths | 2,448 sq.ft. |
$775,000 |
Airbnb cash on cash: -0.03%
|
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. |
$1,395,000 |
Airbnb cash on cash: -0.16%
|
28 School StreetWoodbury, CTThe Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's li... |
4 beds | 4 baths | 2,708 sq.ft. |
$749,900 |
Airbnb cash on cash: -2.66%
|
920 Main Street SWoodbury, CTWarren's Landing on the Pomperaug is an extraordinary estate where historic character is c... |
4 beds | 6 baths | 5,316 sq.ft. |
$2,995,000 |
Airbnb cash on cash: -1.9%
|
33 Hurds Hill RoadWoodbury, CTBACK ON THE MARKET with a NEW SEPTIC being installed, NEW WELL, and MORE. This generous 5-... |
5 beds | 3 baths | 4,130 sq.ft. |
$555,000 |
Airbnb cash on cash: 1.9%
|
509 Weekeepeemee RoadWoodbury, CTSteeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic i... |
3 beds | 3 baths | 2,346 sq.ft. |
$1,278,000 |
Airbnb cash on cash: -0.56%
|
35 Woodbury Hill #35Woodbury, CTWelcome to beautiful Woodbury, CT! Beautiful 2 BR, 2 1/2 bath condo in sought after Woodbu... |
2 beds | 3 baths | 1,796 sq.ft. |
$510,000 |
Airbnb cash on cash: -2.21%
|
90 Sage RoadWoodbury, CTFrom the moment you pull up to this House on the Hill, you will feel right at home. Built ... |
4 beds | 5 baths | 3,968 sq.ft. |
$1,100,000 |
Airbnb cash on cash: -2.06%
|
69 Nonnewaug RoadWoodbury, CTA Place Where Home Feels Like A Getaway Welcome to 69 Nonnewaug Road, where peaceful count... |
4 beds | 3 baths | 2,568 sq.ft. |
$800,000 |
Airbnb cash on cash: -2.23%
|
63 Main Street NWoodbury, CTReader's Digest named Woodbury the "Most Charming Small Town in Connecticut" in 2024 and r... |
4 beds | 2 baths | 2,662 sq.ft. |
$849,900 |
Airbnb cash on cash: -2.19%
|
36 Atwood RoadWoodbury, CTLooking for the ease of one level living, a beautiful backyard, and the peace of mind that... |
3 beds | 1 baths | 1,008 sq.ft. |
$375,000 |
Airbnb cash on cash: 2.33%
|
36 Main Street SWoodbury, CTStep into timeless charm with this classic 1800 New England Colonial in historic Woodbury.... |
3 beds | 3 baths | 1,909 sq.ft. |
$595,000 |
Airbnb cash on cash: 0.51%
|
15 Woods WayWoodbury, CTEnjoy privacy and a peaceful natural setting in this inviting 3-bedroom, 2.5-bath condo at... |
3 beds | 3 baths | 1,467 sq.ft. |
$299,999 |
Airbnb cash on cash: 3.14%
|
Real Estate investment in Woodbury, CT
There are 20 properties for sale in the city of Woodbury . The median list price in Woodbury is $435,000 and the average price per square foot is $181. In November 2026, the average monthly cash on cash return in Woodbury is 4.00%. The average monthly rental income in Woodbury is $4,037.