Active Under Contract
Price CutPrice Drop: $205K (11/07)
Single family home for sale at 55 Good Hl Rd, Woodbury, CT 06798 | MLS# 24136657 | Listing updated on 2026-11-07
Photo 1 of Single family home for sale at 55 Good Hl Rd, Woodbury, CT 06798 | MLS# 24136657 | Listing updated on 2026-11-07
Photo 2 of Single family home for sale at 55 Good Hl Rd, Woodbury, CT 06798 | MLS# 24136657 | Listing updated on 2026-11-07
Photo 3 of Single family home for sale at 55 Good Hl Rd, Woodbury, CT 06798 | MLS# 24136657 | Listing updated on 2026-11-07
Photo 4 of Single family home for sale at 55 Good Hl Rd, Woodbury, CT 06798 | MLS# 24136657 | Listing updated on 2026-11-07
36+
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Street View

$1,790,000

Monthly Est:$8,909

  • Beds Icon4 Beds
  • Beds Icon
    5 Baths
  • Beds Icon3,324sqft

55 Good Hl Rd, Woodbury, CT 06798

$8,909/moEst:

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  • Single Family Residence

  • Built in 1685

  • $-- HOA

  • 3.67 acres lot

  • $539/sq.ft

Description

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.

  • Houzeo last checked: 2 minutes ago
  • Listing updated: November 7, 2026 at 4:48 pm
  • Listing Provided by: Stacey Matthews | W. Raveis Lifestyles Realty
  • Source: SMART MLS-CT | MLS#: 24136657 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Litchfield County

  • City

    Woodbury

  • Neighborhood

    --

  • Year Built

    1685

  • HOA Fees

    -

  • Finished Area

    3,324 sqft

  • Lot Size

    3.67 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24136657

  • MLS Status

    Under Contract

  • Days on Market

    378

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 5

Interior

  • Cooling

    Central Air

  • Appliances

    Range Hood, Refrigerator, Dishwasher, Washer, Dryer

  • Exterior Features

    Terrace, Barn, Cabana, Deck, Garden Area, French Doors

  • Sewer

    Septic

  • Heating

    Propane

  • Interior Features

    Open Floor Plan

Construction

  • Year Built

    Year Built: 1685

  • Home type

    Single Family Residence

  • Architectural Style

    Colonial, Antique

  • Foundation Details

    Concrete, Stone

  • Roof

    Wood Shingle

Utilities & Energy

  • Basement

    Partial, Unfinished

  • Pool Features

    Gunite, In Ground Pool

  • Laundry Features

    Upper Level

  • Water Source

    Private Well

  • Parking Features

    Barn, Detached Garage, Driveway

Other Features

  • Subdivision Name

    Good Hill

  • Lot Features

    Level Lot, Cleared, Professionally Landscaped, Open Lot

Price History

DateEventPrice

08/24/2026

Source: mls_logoSMART MLS-CT #24136657

Contingent (Active Under Contract)

$1,790,000 -10.28%

$539/sqft

05/31/2026

Source: mls_logoSMART MLS-CT #24136657

Price Increased

$1,995,000 +7.84%

$600/sqft

05/08/2026

Source: mls_logoSMART MLS-CT #24136657

Price Decreased

$1,850,000 -7.27%

$557/sqft

03/02/2026

Source: mls_logoSMART MLS-CT #24136657

Listed for Sale

$1,995,000 +29.55%

$600/sqft

07/17/2024

Source: #24005954

Price Increased

$1,540,000 +75.00%

$463/sqft

Show more

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Nov 12, 2026, 09:50AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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