55 Good Hill Road, Woodbury, Connecticut

$1,995,000

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4

Beds

5

Baths

3,324

Square feet

3.67

Acres

About 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 extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living

Features of 55 Good Hill Road

MLS® # 24136657
Price $1,995,000
Bedrooms 4
Bathrooms 5.00
Full Baths 4
Half Baths 1
Square Footage 3,324
Acres 3.67
Type Single Family For Sale
Style Colonial, Antique
Status Active

Community Information

Address 55 Good Hill Road
Area Good Hill
City Woodbury
County Litchfield
State Connecticut
Zip Code 06798

Amenities

Parking Spaces 6
Parking Barn, Detached Garage, Driveway
# of Garages 2
Is Waterfront Yes
Waterfront Brook
Has Pool Yes
Pool Gunite, In Ground Pool

Interior

Interior Features Open Floor Plan
Appliances Range Hood, Refrigerator, Dishwasher, Washer, Dryer
Heating Hydro Air, Propane
Cooling Central Air
Fireplace Yes
# of Fireplaces 4
Has Basement Yes
Basement Partial, Unfinished

Exterior

Exterior Clapboard
Exterior Features Terrace, Barn, Cabana, Deck, Garden Area, French Doors
Lot Description Level Lot, Cleared, Professionally Landscaped, Open Lot
Roof Wood Shingle
Foundation Concrete, Stone

School Information

Elementary Mitchell
Middle Per Board of Ed
High Nonnewaug

Additional Information

Date Listed October 30th, 2025
Zoning R40
RE / Bank Owned No

Listing Details

OfficeW. Raveis Lifestyles Realty

Listing Map

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Listing information last updated on October 30th, 2025 at 11:05am EDT.