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55 Good Hill Road, 
Woodbury, CT 06798

$1,995,000


4

Beds


5

Baths


3,324

Sq Ft


Single Family

Active

Listed by

Stacey Matthews

Pels Matthews

W. Raveis Lifestyles Realty

Last updated:

November 10, 2025, 12:43 PM

MLS#

24136657

Source:

CT

About This Home

55 Good Hill Road

Step into History with Modern Comfort 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.

Home Facts

Single Family

5 Baths

4 Bedrooms

Built in 1685

Price Summary

1,995,000

$600 per Sq. Ft.

MLS #:

24136657

Last Updated:

November 10, 2025, 12:43 PM

Added:

12 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

4

Interior

Living Area:

3,324 Sq. Ft.


Structure

Structure

Architectural Style:

Antique, Colonial

Building Area:

3,324 Sq. Ft.

Year Built:

1685


Lot

Lot Size (Sq. Ft):

159,865


Finances & Disclosures

Finances

Price:

$1,995,000

Price per Sq. Ft:

$600 per Sq. Ft.

Source:CT
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