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 RdWoodbury, CTWelcome to Upper Grassy Hill Living! |
4 beds | 3 baths | 3,784 sq.ft. |
$895,000 |
Airbnb cash on cash: -1.93%
|
62 Heritage DrWoodbury, CTBeautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woo... |
4 beds | 2 baths | 3,223 sq.ft. |
$799,900 |
Airbnb cash on cash: -1.68%
|
9 Spring StWoodbury, CTCharming Colonial just steps to town center. Living room with beautiful wood floor and bui... |
3 beds | 1 baths | 1,332 sq.ft. |
$398,000 |
Airbnb cash on cash: 1.1%
|
22 Woodbury Pl #22Woodbury, CTIncredible opportunity to move right into this Stunning Updated Turn-Key, 3 Bedroom 2 full... |
3 beds | 2 baths | 1,210 sq.ft. |
$329,900 |
Airbnb cash on cash: -0.06%
|
253 Bacon Pond RdWoodbury, CTWelcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury... |
4 beds | 2 baths | 2,283 sq.ft. |
$895,000 |
Airbnb cash on cash: -1.4%
|
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: -1.39%
|
16 Gate Post LnWoodbury, 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: -1.77%
|
819 Main St NWoodbury, CTOpen Meadow Farm, a beautifully maintained property offering a blend of rural charm and mo... |
3 beds | 3 baths | 2,992 sq.ft. |
$1,575,000 |
Airbnb cash on cash: -0.92%
|
92 Minortown RdWoodbury, 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: -0.45%
|
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: 0.16%
|
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: -1.57%
|
229 Bacon Pond Rd #312Woodbury, CT229 Bacon Pond Rd #312, Woodbury, CT 06798 | Condo/Coop |
2 beds | 1 baths | 913 sq.ft. |
$219,900 |
Airbnb cash on cash: -1.5%
|
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: -1.53%
|
54 Clubhouse Dr #54Woodbury, CTWelcome to this light-filled and beautifully maintained townhome in the highly sought-afte... |
2 beds | 2 baths | 1,916 sq.ft. |
$288,990 |
Airbnb cash on cash: -0.51%
|
49 Scuppo RdWoodbury, CTDiscover this beautifully updated ranch-style home ideally situated on over an acre of lev... |
3 beds | 1 baths | 2,292 sq.ft. |
$540,000 |
Airbnb cash on cash: 0.24%
|
339 Main St SWoodbury, CT339 Main St S, Woodbury, CT 06798 | Single Family Residential |
4 beds | 2 baths | 3,700 sq.ft. |
$849,500 |
Airbnb cash on cash: -2.59%
|
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: -0.52%
|
380 Southbury RdWoodbury, CT380 Southbury Rd, Roxbury, CT 06783 | Single Family Residential |
4 beds | 4 baths | 6,444 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -2.83%
|
30 Hollow RdWoodbury, CTStep through the doors of history and into one of Connecticut's most treasured colonial re... |
5 beds | 4 baths | 4,884 sq.ft. |
$1,395,000 |
Airbnb cash on cash: -0.99%
|
86 Quail Run RdWoodbury, CT86 Quail Run Rd, Woodbury, CT 06798 | Single Family Residential |
3 beds | 2 baths | 2,060 sq.ft. |
$765,000 |
Airbnb cash on cash: -1.46%
|
8 Curtiss MdwsWoodbury, CT8 Curtiss Mdws, Woodbury, CT 06798 | Single Family Residential |
4 beds | 3 baths | 3,865 sq.ft. |
$874,900 |
Airbnb cash on cash: -2.59%
|
19 Clubhouse Dr #19Woodbury, CTAt Woodlake, you're not just buying a home, you're buying a lifestyle. From being FHA Appr... |
3 beds | 2 baths | 1,708 sq.ft. |
$286,000 |
Airbnb cash on cash: 0.64%
|
Flanders RdWoodbury, CTFlanders Rd, Woodbury, CT 06798 | Other |
N/A beds | N/A baths | N/A |
$1,150,000 |
Airbnb cash on cash: -2.57%
|
28 School StWoodbury, CTThe Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's li... |
4 beds | 3 baths | 2,708 sq.ft. |
$775,000 |
Airbnb cash on cash: -1.75%
|
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: -2.61%
|
48 Woods WayWoodbury, CT48 Woods Way, Woodbury, CT 06798 | Condo/Coop |
2 beds | 2 baths | 1,182 sq.ft. |
$259,900 |
Airbnb cash on cash: -0.94%
|
6 Easy StWoodbury, CT6 Easy St, Woodbury, CT 06798 | Single Family Residential |
3 beds | 1 baths | 1,562 sq.ft. |
$259,000 |
Airbnb cash on cash: 1.87%
|
920 Main St SWoodbury, CTWarren's Landing on the Pomperaug is an extraordinary estate where historic character is c... |
4 beds | 4 baths | 5,316 sq.ft. |
$2,995,000 |
Airbnb cash on cash: -1.65%
|
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: -2.59%
|
112 W Lake Rd #112Woodbury, CT112 W Lake Rd #112, Woodbury, CT 06798 | Condo/Coop |
2 beds | 2 baths | 1,197 sq.ft. |
$1,795,000 |
Airbnb cash on cash: -2.68%
|
40 Ruffin RdWoodbury, CT40 Ruffin Rd, Woodbury, CT 06798 | Single Family Residential |
4 beds | 2 baths | 2,732 sq.ft. |
$1,790,000 |
Airbnb cash on cash: -2.87%
|
229 Bacon Pond Rd #354Woodbury, CT229 Bacon Pond Rd #354, Woodbury, CT 06798 | Condo/Coop |
2 beds | 1 baths | 913 sq.ft. |
$185,000 |
Airbnb cash on cash: -1.2%
|
96 Quail Run RdWoodbury, CT96 Quail Run Rd, Woodbury, CT 06798 | Single Family Residential |
4 beds | 2 baths | 2,400 sq.ft. |
$895,000 |
Airbnb cash on cash: -2.64%
|
16 Fox Run #16Woodbury, CT16 Fox Run #16, Woodbury, CT 06798 | Condo/Coop |
2 beds | 2 baths | 1,813 sq.ft. |
$229,000 |
Airbnb cash on cash: -0.65%
|
11 Lower Cmns #11Woodbury, CT11 Lower Cmns #11, Woodbury, CT 06798 | Condo/Coop |
2 beds | 2 baths | 1,432 sq.ft. |
$310,000 |
Airbnb cash on cash: -1.26%
|
Real Estate investment in Woodbury, CT
There are 53 properties for sale in the city of Woodbury . The median list price in Woodbury is $432,950 and the average price per square foot is $183. In August 2026, the average monthly cash on cash return in Woodbury is 3.00%. The average monthly rental income in Woodbury is $3,217.