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.
For sale
$1,995,000
55 Good Hill Road, Woodbury, CT 06798
4beds
3,324sqft
Est.:
Single Family Residence
Built in 1685
3.67 Acres Lot
$-- Zestimate®
$600/sqft
$-- HOA
What's special
Sparkling poolHistoric cooking fireplaceNew mahogany deckPicturesque bridgeImpressive central hearthLarge center islandBreakfast bar
- 28 days |
- 4,392 |
- 240 |
Zillow last checked: 7 hours ago
Listing updated: March 02, 2026 at 08:49am
Listed by:
Stacey Matthews (203)671-9067,
W. Raveis Lifestyles Realty 860-868-0511,
Pels Matthews 203-671-5432,
W. Raveis Lifestyles Realty
Source: Smart MLS,MLS#: 24136657
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Heating
- Hydro Air, Propane
Cooling
- Central Air
Appliances
- Included: Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Upper Level
Features
- Open Floorplan
- Doors: French Doors
- Basement: Partial,Unfinished
- Attic: Walk-up
- Number of fireplaces: 4
Interior area
- Total structure area: 3,324
- Total interior livable area: 3,324 sqft
- Finished area above ground: 3,324
- Finished area below ground: 0
Property
Parking
- Total spaces: 6
- Parking features: Barn, Detached, Driveway, Private
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Terrace, Deck
- Exterior features: Garden
- Has private pool: Yes
- Pool features: Gunite, In Ground
- On waterfront: Yes
- Waterfront features: Waterfront, Brook
Lot
- Size: 3.67 Acres
- Features: Level, Cleared, Landscaped, Open Lot
Details
- Additional structures: Barn(s), Cabana
- Parcel number: 933432
- Zoning: R40
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Antique
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter, Stone
- Roof: Wood
Condition
- New construction: No
- Year built: 1685
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
Community
- Features: Basketball Court, Health Club, Library, Medical Facilities, Park, Private School(s), Stables/Riding
- Subdivision: Good Hill
HOA
- Has HOA: No
Location
- Region: Woodbury
Financial & listing details
- Price per square foot: $600/sqft
- Tax assessed value: $579,040
- Annual tax amount: $13,677
- Date on market: 3/2/2026
- Exclusions: pwdr rm mirror, dining & upstairs hall chandeliers, fridge/bsmt, sconces/entry, picture lights/living room. ceiling lights/2 upstairs bdrms, microwave
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 3/2/2026 | Listed for sale | $1,995,000$600/sqft |
Source:  Smart MLS #24136657 Report a problem | ||
| 11/28/2025 | Listing removed | $1,995,000$600/sqft |
Source: Smart MLS #24136657 Report a problem | ||
| 10/30/2025 | Listed for sale | $1,995,000+29.5%$600/sqft |
Source: Smart MLS #24136657 Report a problem | ||
| 7/16/2024 | Sold | $1,540,000-0.6%$463/sqft |
Source: Smart MLS #24005954 Report a problem | ||
| 4/16/2024 | Pending sale | $1,550,000$466/sqft |
Source: Smart MLS #24005954 Report a problem | ||
| 4/1/2024 | Listed for sale | $1,550,000+76.1%$466/sqft |
Source: Smart MLS #24005954 Report a problem | ||
| 12/27/2023 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 11/21/2023 | Listed for rent | $8,750$3/sqft |
Source: Zillow Rentals Report a problem | ||
| 11/8/2023 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 9/29/2023 | Listed for rent | $8,750$3/sqft |
Source: Zillow Rentals Report a problem | ||
| 6/30/2022 | Sold | $880,000-1.7%$265/sqft |
Source: Smart MLS #170488537 Report a problem | ||
| 5/11/2022 | Contingent | $895,000$269/sqft |
Source: Smart MLS #170488537 Report a problem | ||
| 5/7/2022 | Listed for sale | $895,000+25.2%$269/sqft |
Source: Smart MLS #170488537 Report a problem | ||
| 6/6/2013 | Sold | $715,000-3.1%$215/sqft |
Source: Public Record Report a problem | ||
| 2/22/2013 | Listing removed | $738,000$222/sqft |
Source: Klemm Real Estate #L143011 Report a problem | ||
| 1/19/2013 | Pending sale | $738,000$222/sqft |
Source: Klemm Real Estate #L143011 Report a problem | ||
| 12/4/2012 | Price change | $738,000-17.5%$222/sqft |
Source: Klemm Real Estate #L143011 Report a problem | ||
| 6/21/2012 | Listed for sale | $895,000+25.2%$269/sqft |
Source: Klemm Real Estate #L143011 Report a problem | ||
| 6/12/2012 | Sold | $715,000-26.7%$215/sqft |
Source: Agent Provided Report a problem | ||
| 5/12/2011 | Price change | $975,000-24.4%$293/sqft |
Source: Alliance Realty NE, LLC #G591738 Report a problem | ||
| 9/8/2010 | Listed for sale | $1,290,000$388/sqft |
Source: Klemm Real Estate Report a problem | ||
| 8/7/2010 | Listing removed | $1,290,000$388/sqft |
Source: Klemm Real Estate Report a problem | ||
| 6/11/2010 | Listed for sale | $1,290,000-7.9%$388/sqft |
Source: Klemm Real Estate Report a problem | ||
| 1/18/2010 | Listing removed | $1,400,000$421/sqft |
Source: KLEMM REAL ESTATE #L129104 Report a problem | ||
| 12/18/2008 | Listed for sale | $1,400,000-11.9%$421/sqft |
Source: Listhub #L128793 Report a problem | ||
| 3/11/2008 | Listing removed | $1,590,000$478/sqft |
Source: NCI Report a problem | ||
| 2/1/2008 | Listed for sale | $1,590,000$478/sqft |
Source: NCI Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $13,677 +2.4% | $579,040 +0.5% |
| 2024 | $13,350 +6.2% | $576,170 +33.2% |
| 2023 | $12,570 -0.4% | $432,550 |
| 2022 | $12,617 | $432,550 |
| 2021 | $12,617 | $432,550 |
| 2020 | $12,617 | $432,550 |
| 2019 | $12,617 -0.4% | $432,550 -9.2% |
| 2018 | $12,667 -2.1% | $476,580 |
| 2017 | $12,944 +3.3% | $476,580 |
| 2016 | $12,529 +0.8% | $476,580 |
| 2015 | $12,424 +1.5% | $476,580 |
| 2014 | $12,243 +1.9% | $476,580 -7.2% |
| 2013 | $12,019 +1.6% | $513,630 +5.2% |
| 2012 | $11,828 +7.9% | $488,150 |
| 2011 | $10,964 +4.7% | $488,150 |
| 2010 | $10,471 +1.5% | $488,150 |
| 2009 | $10,315 -16.6% | $488,150 -3.9% |
| 2008 | $12,372 +1.6% | $508,070 |
| 2007 | $12,173 +5.1% | $508,070 |
| 2006 | $11,579 +6.4% | $508,070 |
| 2005 | $10,883 | $508,070 |
| 2004 | $10,883 +84% | $508,070 +134.1% |
| 2003 | $5,915 -9.8% | $217,050 -35.6% |
| 1997 | $6,558 | $337,180 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$13,247/mo
Principal & interest
$10288
Property taxes
$2959
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Climate risks
Neighborhood: 06798
Nearby schools
GreatSchools rating
- 5/10Mitchell Elementary SchoolGrades: PK-5Distance: 1.1 mi
- 6/10Woodbury Middle SchoolGrades: 6-8Distance: 1 mi
- 9/10Nonnewaug High SchoolGrades: 9-12Distance: 2.2 mi
Schools provided by the listing agent
- Elementary: Mitchell
- High: Nonnewaug
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Local experts in 06798
- Connecticut
- Litchfield County
- Woodbury
- 06798
- 55 Good Hill Road
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