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 |
|---|---|---|---|
3 Tamarack Ln #3Woodbury, CTUnique, newly renovated 2 bedrm, 3 full bath townhouse with legal studio on LL for extra l... |
2 beds | 3 baths | 1,059 sq.ft. |
$289,000 |
Airbnb cash on cash: -0.01%
|
48 Coach Light DriveWoodbury, CTGloriously Peaceful, Private, Magnificent views...This exceptional residence among similar... |
4 beds | 5 baths | 5,216 sq.ft. |
$1,599,000 |
Airbnb cash on cash: N/A
|
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: N/A
|
16 Cross Brook RdWoodbury, CTPeace and quiet can be found at this address! Come home to spacious rooms, wood floors, fi... |
3 beds | 2 baths | 1,750 sq.ft. |
$649,900 |
Airbnb cash on cash: 0.36%
|
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: N/A
|
55 Good Hill RdWoodbury, CTUnwind and create lasting memories in your private sanctuary at 55 Good Hill Road, nestled... |
4 beds | 4 baths | 3,324 sq.ft. |
$1,995,000 |
Airbnb cash on cash: N/A
|
38 Mountain RdWoodbury, CTWelcome to this 3 bedroom, 2.5 bath Colonial in Woodbury! This home features a private dri... |
3 beds | 2 baths | 1,704 sq.ft. |
$494,000 |
Airbnb cash on cash: 1.08%
|
27 Middle Quarter RdWoodbury, CT4 Bedroom 1.5 Bath Colonial Built in 1825 on 1.32 Acres with 2 Large Barns on the property... |
3 beds | 2 baths | 2,042 sq.ft. |
$999,900 |
Airbnb cash on cash: -1.59%
|
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: -0.79%
|
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: 1.6%
|
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. |
$849,000 |
Airbnb cash on cash: -0.19%
|
439 Washington RdWoodbury, CT439 Washington Rd, Woodbury, CT 06798 | Single Family Residential |
2 beds | 1 baths | 1,920 sq.ft. |
$289,000 |
Airbnb cash on cash: 0.44%
|
8 Tamarack Ln #8Woodbury, CT8 Tamarack Ln #8, Woodbury, CT 06798 | Condo/Coop |
2 beds | 2 baths | 2,118 sq.ft. |
$325,000 |
Airbnb cash on cash: -1.32%
|
1545 Main St NWoodbury, CT1545 Main St N, Woodbury, CT 06798 | Other |
N/A beds | N/A baths | N/A |
$400,000 |
Airbnb cash on cash: N/A
|
2 South Mdws #2Woodbury, CT2 S Meadows Mdws #2, Woodbury, CT 06798 | Condo/Coop |
3 beds | 2 baths | 2,069 sq.ft. |
$347,500 |
Airbnb cash on cash: -0.11%
|
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. |
$288,990 |
Airbnb cash on cash: -0.22%
|
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. |
$540,000 |
Airbnb cash on cash: 0.65%
|
339 Main St SWoodbury, CT339 Main St S, Woodbury, CT 06798 | Single Family Residential |
4 beds | 2 baths | 3,700 sq.ft. |
$874,900 |
Airbnb cash on cash: N/A
|
110 Brushy Hill RdWoodbury, CT110 Brushy Hill Rd, Woodbury, CT 06798 | Single Family Residential |
3 beds | 2 baths | 2,100 sq.ft. |
$499,999 |
Airbnb cash on cash: -0.07%
|
380 Southbury RdWoodbury, CT380 Southbury Rd, Roxbury, CT 06783 | Single Family Residential |
4 beds | 4 baths | 6,444 sq.ft. |
$1,550,000 |
Airbnb cash on cash: N/A
|
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: 0.16%
|
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. |
$774,900 |
Airbnb cash on cash: 1.43%
|
94 Quail Run RdWoodbury, CT94 Quail Run Rd, Woodbury, CT 06798 | Single Family Residential |
3 beds | 2 baths | 2,081 sq.ft. |
$645,000 |
Airbnb cash on cash: -0.8%
|
86 Quail Run RdWoodbury, CT86 Quail Run Rd, Woodbury, CT 06798 | Single Family Residential |
3 beds | 2 baths | 2,060 sq.ft. |
$745,000 |
Airbnb cash on cash: -1.11%
|
8 Curtiss MdwsWoodbury, CT8 Curtiss Mdws, Woodbury, CT 06798 | Single Family Residential |
4 beds | 3 baths | 3,865 sq.ft. |
$899,000 |
Airbnb cash on cash: N/A
|
437 Middle Road TpkeWoodbury, CT437 Middle Road Tpke, Woodbury, CT 06798 | Single Family Residential |
3 beds | 1 baths | 1,144 sq.ft. |
$545,000 |
Airbnb cash on cash: -0.32%
|
19 Clubhouse Drive #19Woodbury, CTAt Woodlake, you're not just buying a home, you're buying a lifestyle. From being FHA Appr... |
3 beds | 3 baths | 1,708 sq.ft. |
$286,000 |
Airbnb cash on cash: 1.41%
|
Flanders RdWoodbury, CTFlanders Rd, Woodbury, CT 06798 | Other |
N/A beds | N/A baths | N/A |
$1,150,000 |
Airbnb cash on cash: N/A
|
4 Woods Way #4Woodbury, CT4 Woods Way #4, Woodbury, CT 06798 | Condo/Coop |
2 beds | 2 baths | 1,182 sq.ft. |
$260,000 |
Airbnb cash on cash: -0.8%
|
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. |
$775,000 |
Airbnb cash on cash: N/A
|
17 Woodbury Hl #17Woodbury, CT17 Woodbury Hl #17, Woodbury, CT 06798 | Condo/Coop |
2 beds | 2 baths | 1,673 sq.ft. |
$545,000 |
Airbnb cash on cash: -2.46%
|
48 Woods WayWoodbury, CT48 Woods Way, Woodbury, CT 06798 | Condo/Coop |
2 beds | 2 baths | 1,182 sq.ft. |
$279,500 |
Airbnb cash on cash: -0.8%
|
54 School StreetWoodbury, CTTimeless Elegance in the Heart of the Historic District . Step back in time without sacrif... |
3 beds | 2 baths | 2,148 sq.ft. |
$589,000 |
Airbnb cash on cash: 0.25%
|
77 Hesseky Meadow RdWoodbury, CT77 Hesseky Meadow Rd, Woodbury, CT 06798 | Single Family Residential |
4 beds | 5 baths | 4,790 sq.ft. |
$829,900 |
Airbnb cash on cash: N/A
|
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: N/A
|
33 Hurds Hill RoadWoodbury, CTNestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a... |
5 beds | 3 baths | 4,130 sq.ft. |
$565,000 |
Airbnb cash on cash: 2.8%
|
20 Stagecoach RdWoodbury, CT20 Stagecoach Rd, Woodbury, CT 06798 | Single Family Residential |
4 beds | 2 baths | 2,157 sq.ft. |
$629,000 |
Airbnb cash on cash: N/A
|
1917 Main St NWoodbury, CT1917 Main St N, Woodbury, CT 06798 | Single Family Residential |
4 beds | 2 baths | 4,819 sq.ft. |
$865,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Woodbury, CT
There are 47 properties for sale in the city of Woodbury . The median list price in Woodbury is $450,000 and the average price per square foot is $188. In June 2026, the average monthly cash on cash return in Woodbury is 2.00%. The average monthly rental income in Woodbury is $3,129.