About 55 Good Hill Road
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.
Features of 55 Good Hill Road
| MLS® # | 24136657 |
|---|---|
| Price | $1,790,000 |
| 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 |
|---|---|
| Days on Market | 221 |
| Zoning | R40 |
| RE / Bank Owned | No |
Listing Details
| Office | W. Raveis Lifestyles Realty |
|---|