Browse All Woodbury CT 4 Bedroom Properties for Sale

Welcome to 34 Pilgrim Trail, a home thoughtfully cared for and enjoyed for 25.5 years. This peaceful Woodbury property features granite kitchen countertops, a tiled backs...

4 Beds
2 Baths
24203216 MLS

385 Middle Road Tpke, Woodbury $875,000

Set on 3.29 picturesque acres bordering conservation land, this beautifully maintained and thoughtfully remodeled country Cape is filled with character, custom craftsmans...

4 Beds
3 Baths
24202477 MLS

90 Sage Rd, Woodbury $1,200,000

Fabulous Center Hall Colonial......Don't be one of those people who drive by and sum it up. This home was built in "The Era". The era I'm speaking of is truly the way hom...

4 Beds
5 Baths
24202077 MLS

138 Minortown Rd, Woodbury $1,600,000

Turnkey Equestrian Facility on 21 Acres. A rare opportunity to own a fully operational equestrian property offering the perfect blend of functionality, comfort, and incom...

4 Beds
3 Baths
24199540 MLS

126 Main St N, Woodbury $699,000

Classic 1930s Colonial set along Main Street in Woodbury, offering the timeless character and craftsmanship of the era. Thoughtfully set back from the road on an expansiv...

4 Beds
2 Baths
24194243 MLS

11 Pleasant St, Woodbury $959,000

Timeless Elegance & Immaculate Detail. Welcome to The Naramore House, a piece of living history. Lovingly preserved since 1898, this pristine colonial home seamlessly ble...

4 Beds
3 Baths
24188039 MLS

16 Gate Post Ln, Woodbury $1,100,000

Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law s...

4 Beds
4 Baths
24192457 MLS

348 Hoop Pole Hill Rd, Woodbury $599,900 ▼

Exceptional opportunity to renovate and create your dream country estate on 12.69 private acres in the heart of Woodbury. Privately sited along a quiet country road with ...

4 Beds
3 Baths
24192145 MLS

96 Quail Run Rd, Woodbury $895,000

QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 a...

4 Beds
3 Baths
24172964 MLS

62 Heritage Dr, Woodbury $769,900 ▼

Beautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woodbury's most desirable locations. Just two streets from Woodbury's nationally re...

4 Beds
3 Baths
24185801 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

1917 Main St N, Woodbury $850,000 ▼

Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an appr...

4 Beds
2 Baths
24183601 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

28 School St, Woodbury $775,000

The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two ...

4 Beds
4 Baths
24138386 MLS

253 Bacon Pond Rd, Woodbury $895,000

Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived ...

4 Beds
3 Baths
24172742 MLS

8 Curtiss Mdws, Woodbury $874,900 ▼

Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back fro...

4 Beds
5 Baths
24172449 MLS

339 Main St S, Woodbury $699,900 ▼

Watch the parade from your front yard, walk to school, walk to the excellent restaurants in town, walk to the library and to the local park and market! Fabulous location!...

4 Beds
3 Baths
24165323 MLS

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.

4 Bedroom Woodbury Real Estate

Our website features the best real estate search for 4 bedroom properties available in Woodbury and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!