Claudia Dixon

55 Good Hill Road

Woodbury, CT
$ 1,790,000 Beds 4 Baths 4.5 Sq 3,324
Monthly Estimate* How much can I afford?

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 Live. Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

Single Family

  • Price
  • $ 1,790,000
  • City
  • Woodbury
  • Bedrooms
  • 4
  • Full Bathrooms
  • 4
  • County
  • Litchfield
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 3.67 Acres
  • Zip
  • 06798
  • Sqr Footage
  • 3,324
  • Year Built
  • 1685
  • Taxes
  • $ 14681
  • Style
  • MLS#
  • 24136657
Listed By: Stacey Matthews 203-671-9067 with W. Raveis Lifestyles Realty. - (860) 868-0511
Data Source: Smart MLS

Features

General

Zoning R40
Neighborhood Good Hill
County Litchfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 3.67
Directions rte 317
High School Nonnewaug
City Woodbury
Elementary School Mitchell
Sq Ft Total 3324
DOM 206
Year Built 1685
Exclusions pwdr rm mirror, dining & upstairs hall chandeliers, fridge/bsmt, sconces/entry, picture lights/living room. ceiling lights/2 upstairs bdrms, microwave
Style Colonial,Antique
Year Built Source Approximate
Pool Description Gunite,In Ground Pool

Interior Features

Cooling System Central Air
Total Rooms 11
Basement Description Partial,Unfinished

Exterior Features

Water Source Private Well
Lot Description Level Lot,Cleared,Professionally Landscaped,Open Lot
Color White

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
Agent Photo

Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Mitchell Elementary School
Middle School Unknown Middle School
High School Nonnewaug High School

Price History

3/2/2026 Listed $1,995,000
5/8/2026 7% - $1,850,000
5/31/2026 8% - $1,995,000
8/24/2026 10% - $1,790,000

Property vs Zip Code Average in 06798

Price
AVG $870K
$1.79M
Taxes
AVG $8,928
$14,681
Year Built
AVG 1929
1685

In The Neighborhood

Areas That We Cover

55 Good Hill Road Woodbury, CT is a Single Family Home for sale at $1790000 with 3324 sqft and a lot size of 3.67 Acres Acre(s). 55 Good Hill Road Woodbury has 4 bedrooms, 4 baths and was built in 1685. The property's zip code is 06798 which is in Woodbury, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Claudia Dixon

Claudia Dixon

Sales Associate

860-881-7725

By pressing Contact Me, you agree that Weichert® may contact you via phone about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our Privacy Policy