Charming antique two-family property in the heart of Woodbury featuring a main residence plus a separate legal apartment over the detached 2-car garage-ideal for rental income, in-law setup, or owner-occupant flexibility. The main home offers 3 bedrooms, 1 bath, wide board antique flooring, original built-ins, and three fireplaces, including one in the cozy eat-in kitchen. The apartment provides approximately 700 sq ft of additional living space with a full bath and private setting. Set on a beautiful 1.46-acre treed lot with gardens, irrigation, and open space. Convenient in-town location close to shopping, dining, and commuter routes.
Accepting backups
$475,000
242 Bacon Pond Road, Woodbury, CT 06798
4beds
1,836sqft
Est.:
Multi Family
Built in 1782
-- sqft lot
$-- Zestimate®
$259/sqft
$-- HOA
What's special
- 17 days |
- 3,080 |
- 176 |
Zillow last checked:
Listing updated:
Listed by:
Timothy Drakeley (203)510-9184,
Drakeley Real Estate, Inc. 203-263-4336
Source: Smart MLS,MLS#: 24162107
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Water Heater
Features
- Basement: Crawl Space,Partial
- Attic: Pull Down Stairs
- Number of fireplaces: 3
Interior area
- Total structure area: 1,836
- Total interior livable area: 1,836 sqft
- Finished area above ground: 1,836
Property
Parking
- Total spaces: 2
- Parking features: Detached
- Garage spaces: 2
Features
- Patio & porch: Porch, Patio
- Exterior features: Garden
Lot
- Size: 1.46 Acres
- Features: Level
Details
- Parcel number: 935411
- Zoning: OS60
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Units on different Floors
- Property subtype: Multi Family
Materials
- Shake Siding
- Foundation: Concrete Perimeter, Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1782
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
HOA
- Has HOA: No
Location
- Region: Woodbury
Financial & listing details
- Price per square foot: $259/sqft
- Tax assessed value: $278,180
- Annual tax amount: $6,571
- Date on market: 3/28/2026
Estimated market value
Not available
Estimated sales range
Not available
$2,581/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 4/1/2026 | Listed for sale | $475,000+46.2%$259/sqft |
Source: | ||
| 1/31/2020 | Sold | $325,000-4.4%$177/sqft |
Source: | ||
| 11/11/2019 | Price change | $339,900-2.9%$185/sqft |
Source: William Raveis Real Estate #170240237 Report a problem | ||
| 9/30/2019 | Listed for sale | $349,900+9.3%$191/sqft |
Source: William Raveis Real Estate #170240237 Report a problem | ||
| 11/4/2004 | Sold | $320,000$174/sqft |
Source: | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,571 +2% | $278,180 |
| 2024 | $6,445 +5% | $278,180 +31.7% |
| 2023 | $6,138 -0.4% | $211,230 |
| 2022 | $6,162 | $211,230 |
| 2021 | $6,162 | $211,230 |
| 2020 | $6,162 | $211,230 |
| 2019 | $6,162 +0.6% | $211,230 -8.3% |
| 2018 | $6,125 -2.1% | $230,430 |
| 2017 | $6,258 +3.3% | $230,430 |
| 2016 | $6,058 +0.8% | $230,430 |
| 2015 | $6,007 +1.5% | $230,430 |
| 2014 | $5,920 -8.5% | $230,430 -16.6% |
| 2013 | $6,468 -3.4% | $276,400 |
| 2012 | $6,697 +7.9% | $276,400 |
| 2011 | $6,208 +4.7% | $276,400 |
| 2010 | $5,929 +1.5% | $276,400 |
| 2009 | $5,840 -3.5% | $276,400 +11.2% |
| 2008 | $6,052 +1.6% | $248,560 |
| 2007 | $5,955 +5.1% | $248,560 |
| 2006 | $5,665 +6.4% | $248,560 |
| 2005 | $5,324 | $248,560 |
| 2004 | $5,324 +63.1% | $248,560 +107.4% |
| 2003 | $3,265 +1.7% | $119,830 -27.4% |
| 1997 | $3,212 | $165,140 |
Find assessor info on the county website
Monthly payment
Est. payment
$3,028/mo
Principal & interest
$2323
Property taxes
$705
More affordability tools
Climate risks
Neighborhood: Woodbury Center
Nearby schools
GreatSchools rating
- 5/10Mitchell Elementary SchoolGrades: PK-5Distance: 1.2 mi
- 6/10Woodbury Middle SchoolGrades: 6-8Distance: 1.4 mi
- 9/10Nonnewaug High SchoolGrades: 9-12Distance: 1.7 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.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Litchfield County
- Woodbury
- 06798
- Woodbury Center
- 242 Bacon Pond Road






