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Street View
$1,790,000
Monthly Est:$8,909
4 Beds
- 5 Baths
4 full baths + 1 half bath
3,324sqft
55 Good Hl Rd, Woodbury, CT 06798
$1,790,000
$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

Property Details
Status
Active Under Contract
Type
Single Family Residence
No. of Stories
-
County
City
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
| Date | Event | Price |
|---|---|---|
08/24/2026 Source: | Contingent (Active Under Contract) | $1,790,000 -10.28% $539/sqft |
05/31/2026 Source: | Price Increased | $1,995,000 +7.84% $600/sqft |
05/08/2026 Source: | Price Decreased | $1,850,000 -7.27% $557/sqft |
03/02/2026 Source: | Listed for Sale | $1,995,000 +29.55% $600/sqft |
07/17/2024 Source: #24005954 | Price Increased | $1,540,000 +75.00% $463/sqft |
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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.
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