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4 Beds
5 Baths
3,324 sqft

$1,790,000

55 Good Hill Road, Woodbury CT, 06798

Price per sqft$538.51
Built in1685
Property size3,324 sqft
Property typeResidential

Overview

Under contract

Under Contract - Continue To Show

Listed Oct 30, 2025

Updated 6 days ago

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.

$11,909/mo

Est. mortgage payment based on a $1,790,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
24136657

Interior Features

Bedrooms
4
Bathrooms
5
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
3.67 Acres

Other Property Details

Taxes
$14,681
Tax Frequency
Annually
Garage
Yes
Pool
Yes
Waterfront
Yes
MLS provider logo

Listed by Stacey Matthews with W. Raveis Lifestyles Realty (203) 671-9067

The IDX display contains information sourced from SmartMLS, Inc. as of 9/30/2026. This information is for personal, non-commercial use only and may not be used for any purpose other than identifying properties the viewer may be interested in purchasing. MLS data is generally considered reliable but is not guaranteed accurate by the MLS. Buyers are responsible for verifying all information and should conduct their own investigation or consult a professional. Some MLS data may have been provided by sources other than the listing agent. Unless stated in writing, the Broker/Agent has not verified information obtained from outside sources. The Broker/Agent may or may not have been the listing and/or selling agent, and cannot guarantee the accuracy of any property location shown on a map. Any offer of compensation is made only to participants of the MLS where the listing is filed.

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Data last updated on 9/30/2026 at 3:08 AM UTC.

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