Browse All Woodbury CT Historical Properties for Sale

Great Ranch well sited on level almost half acre yard, large living room with fireplace, kitchen and dining room overlooking back yard and deck, 2 bedrooms and 1 full bat...

2 Beds
1 Baths
24218073 MLS

36 Main St S, Woodbury $595,000

Step into timeless charm with this classic 1800 New England Colonial in historic Woodbury. Thoughtfully curated wallcoverings weave subtle, boutique elegance and modern p...

3 Beds
3 Baths
24217173 MLS

36 Atwood Rd, Woodbury $375,000

Looking for the ease of one level living, a beautiful backyard, and the peace of mind that comes with major updates already completed? This Woodbury ranch checks all the ...

3 Beds
1 Baths
24215409 MLS

22 Pilgrim Trl Unit G1, Woodbury — Quassuk Heights Gardens $124,900

Welcome to this delightful and exceptionally well cared for condo in the charming town of Woodbury! Just minutes from Main Street, this desirable first floor end unit off...

1 Beds
1 Baths
24212678 MLS
Quassuk Heights Gardens Bldg.

11 Judson Ave, Woodbury $529,000

Looking for a convenient in town location? Built in 1940, this delightful vintage colonial is loaded with the charm of the 1940's. The front to back living room offers a ...

3 Beds
2 Baths
24210084 MLS

1217 Main St N, Woodbury $699,900

Completely renovated and move-in ready, this three-bedroom ranch in North Woodbury has been gutted to the studs and beautifully rebuilt throughout. The open-concept layou...

3 Beds
2 Baths
24211238 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

63 Main St N, Woodbury $849,900

Reader's Digest named Woodbury the "Most Charming Small Town in Connecticut" in 2024 and received the same recognition in 2020 and 2018.That fits this home perfectly. 63 ...

4 Beds
2 Baths
24208978 MLS

578 Old Sherman Hill Rd, Woodbury $550,000

Charming Brick Ranch on 2+ Acres Nestled on more than two acres in a peaceful setting, this well-built brick ranch offers the perfect blend of privacy, comfort, and conve...

3 Beds
2 Baths
24206868 MLS

10 Weekeepeemee Rd, Woodbury $599,900 ▼

The John Cramer House at 10 Weekeepeemee Road is listed on the National Register of Historic Places and is a wonderful example of Greek Revival architecture. Rich in peri...

3 Beds
2 Baths
24207451 MLS

50 Washington Rd, Woodbury $519,000

CHARM, CHARACTER & CLASSIC NEW ENGLAND APPEAL IN HISTORIC WOODBURY! Welcome to this distinctive 1895 Colonial farmhouse, where timeless architectural character blends bea...

3 Beds
2 Baths
24203287 MLS

34 Pilgrim Trl, Woodbury $420,000

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 $1,100,000 ▼

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

126 Main St N, Woodbury $649,900 ▼

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

24 Scuppo Rd, Woodbury $749,900 ▼

Impressive and spacious 5,815 sq. ft. well maintained residence with BRAND NEW ROOF and all new skylight windows(installed 8/15/26) offering exceptional one-level living ...

6 Beds
4 Baths
24187148 MLS

153 Old Sherman Hill Rd, Woodbury $499,900 ▼

Exceptional value and opportunity on 3.5 gorgeous acres! Bring this home back to its original charm. Features hardwood floors throughout and a cozy front porch. The upper...

3 Beds
2 Baths
24194640 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

509 Weekeepeemee Rd, Woodbury $1,278,000 ▼

Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main ho...

3 Beds
3 Baths
24192284 MLS

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

1917 Main St N, Woodbury $780,000 ▼

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 $749,900 ▼

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

30 Hollow Rd, Woodbury $1,395,000 ▼

Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic ...

5 Beds
5 Baths
24168618 MLS

524 Main St S, Woodbury $1,350,000

Prime commercial opportunity on Main Street South in Woodbury, adjacent to the well-known 1754 House restaurant. Formerly the longtime home of Agway/Green Acres, this ver...

1 Baths
24161266 MLS

27 Middle Quarter Rd, Woodbury $999,900 ▼

Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current o...

3 Beds
3 Baths
24146826 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

439 Washington Rd, Woodbury $289,000 ▼

Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can...

2 Beds
2 Baths
24078648 MLS

439 Washington Rd, Woodbury $289,000 ▼

Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can...

2 Baths
24078389 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.

Woodbury Historical Real Estate

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