Browse All Woodbury CT Properties with Pool for Sale

Private Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of Litchfield County, along the desirable Woodbury/Roxbury line, this distinctive...

3 Beds
3 Baths
24209744 MLS

348 Weekeepeemee Rd, Woodbury $2,149,900

Set well back from Weekeepeemee Road in one of Woodbury's finest locations, this exceptionally well-built Colonial offers approximately 5,900 square feet of thoughtfully ...

5 Beds
5 Baths
24209591 MLS

2 Pomperaug Rd, Woodbury $875,000

Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private ...

3 Beds
3 Baths
24209527 MLS

229 Bacon Pond Rd Unit 312, Woodbury image

229 Bacon Pond Rd Unit 312, Woodbury — Town In Country $195,000 ▼

Welcome to 229 Bacon Pond Rd Unit 312 - located in the Town In Country complex, this 2 bed/1 bath unit has been remodeled from top to bottom featuring a brand new kitchen...

2 Beds
1 Baths
24209657 MLS
Town In Country Bldg.

69 Nonnewaug Rd, Woodbury $800,000 ▼

A Place Where Home Feels Like A Getaway Welcome to 69 Nonnewaug Road, where peaceful country living meets the charm of Woodbury! Set on approximately 9.47 acres, this 3-...

4 Beds
3 Baths
24208716 MLS

126 Sherman Hill Rd Unit C15, Woodbury image

126 Sherman Hill Rd Unit C15, Woodbury — Heritage Hills $199,900

Nestled in the scenic hills of Woodbury, Connecticut, this open and airy upper level 2-bedroom condo offers the perfect blend of comfort, charm, and convenience. Soaring ...

2 Beds
2 Baths
24207339 MLS
Heritage Hills Bldg.

229 Bacon Pond Rd Unit 313, Woodbury image

229 Bacon Pond Rd Unit 313, Woodbury — Town In Country $209,900

Move right into this beautifully renovated upper end unit in Woodbury's desirable in-town Town & Country condominium complex. Tastefully updated throughout, this light-fi...

2 Beds
1 Baths
24206004 MLS
Town In Country Bldg.

90 Sage Rd, Woodbury $1,100,000 ▼

From the moment you pull up to this House on the Hill, you will feel right at home. Built when homes were designed for gracious, comfortable living, it feels elegant yet ...

4 Beds
5 Baths
24202077 MLS

8 Woods Way Unit 8, Woodbury — Condos At Woodlake $299,000 ▼

PRETTY AND SO PRIVATE!! Enjoy nature right from your back door in this spacious, freshly painted 3-bedroom home! Imagine relaxing with a cup of coffee on your private dec...

3 Beds
3 Baths
24200604 MLS
Condos At Woodlake Bldg.

35 Woodbury Hill, Unit 35, Woodbury image

35 Woodbury Hill, Unit 35, Woodbury — Woodbury Hill $510,000 ▼

Welcome to beautiful Woodbury, CT! Beautiful 2 BR, 2 1/2 bath condo in sought after Woodbury Hill Condos. Park like grounds with only 78 condos, featuring a saltwater poo...

2 Beds
3 Baths
24188214 MLS
Woodbury Hill Bldg.

241 Hoop Pole Hill Rd, Woodbury $384,900 ▼

INVESTORS TAKE NOTICE!! A rare opportunity to bring your vision to life in beautiful Woodbury. 3BR, 2.5 bath Cape just over 2,000 square feet of comfortable living space ...

3 Beds
3 Baths
24099709 MLS

40 Ruffin Rd, Woodbury $1,590,000 ▼

It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, ma...

4 Beds
3 Baths
24184948 MLS

92 Minortown Rd, Woodbury $775,000 ▼

Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate...

3 Beds
2 Baths
24182784 MLS

920 Main St S, Woodbury $2,995,000

Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home of...

4 Beds
6 Baths
24163576 MLS

17 Woodbury Hill, Unit 17, Woodbury image

17 Woodbury Hill, Unit 17, Woodbury — Woodbury Hill $527,900 ▼

The finest condo complex in one of Litchfield Counties most charming towns! Woodbury Hill is a lovely community of townhouse style homes in a very attractive setting and ...

2 Beds
3 Baths
24179262 MLS
Woodbury Hill Bldg.

55 Good Hill Rd, Woodbury $1,790,000 ▼

Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Liv...

4 Beds
5 Baths
24136657 MLS

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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