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55 Good Hill Road

Woodbury, Connecticut 06798

ACTIVE$1,995,000
Beds
4
Baths
4 | 1
SqFt
3,324
Acres
3.67
Year Built
1685
Matt Caiola

Matt Caiola

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WaterfrontPool2-Car Garage4 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$11,977

per 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.

Listed By

Stacey Matthews

(203) 671-9067

W. Raveis Lifestyles Realty

(860) 868-0511

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.