55 Good Hill Road
Woodbury, Connecticut 06798
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 3,324
- Acres
- 3.67
- Year Built
- 1685
- Neighborhood
- Good Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
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.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- Good Hill
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1685
- Days on Market
- 272 days
- Beds
- 4
- Baths
- 4 full · 1 half
- Living Area
- 3,324 sq ft
- Lot Size
- 3.67 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $13,677 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
24
27 under contract
Median List Price
$857,000
24 active listings
Median Closed Price
$582,500
88 sales
Median Days on Market
53
24 active listings
Median $ / Sq Ft
$296
24 active listings
Sale-to-List Ratio
99.0%
88 sales
How this home compares
List Price
$2.00M
vs $857,000 median
2.3× the median
Price / Sq Ft
$600
vs $296 median
2.0× the median
Days on Market
272 days
vs 53 days median
219 days longer than median
Based on 24 active and 88 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of July 29, 2026.
Location
55 Good Hill Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$10,172
- Property Taxes$1,140
- Insurance$665
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- Good Hill
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Antique
- Year Built
- 1685
- New Construction
- No/Resale
- Living Area
- 3,324 sq ft
Schools
- Elementary
- Mitchell
- High
- Nonnewaug
Interior
- Heating
- Hydro Air
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 4
- Laundry
- Upper Level
- Appliances
- Range HoodRefrigeratorDishwasherWasherDryer
- Basement
- PartialUnfinished
- In-Law Apartment
- PossibleOver Garage
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 3.67 acres
- Zoning
- R40
- Garage / Parking
- 2 garage spaces6 total parking spacesBarnDetached GarageDrivewayPrivate
- Waterfront
- Direct waterfront
- Waterfront Details
- Brook
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteIn Ground Pool
- Construction
- Clapboard
- Color
- White
- Roof
- Wood Shingle
- Foundation
- ConcreteStone
- Exterior Features
- TerraceBarnCabanaDeckGarden AreaFrench Doors
- Lot Description
- Level LotClearedProfessionally LandscapedOpen Lot
Listing & Financials
- Property Taxes
- $13,677 / Annually
- Days on Market
- 272
- MLS #
- 24136657
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Pels Matthews
W. Raveis Lifestyles Realty
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/29/2026 at 11:45 AM UTC.