253 Bacon Pond Road
Woodbury, Connecticut 06798
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,283
- Acres
- 3.19
- Year Built
- 1850
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1850
- Days on Market
- 82 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,283 sq ft
- Lot Size
- 3.19 acres
- Garage / Parking
- 2 garage · 5 total
- Property Taxes
- $8,308 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
26
26 under contract
Median List Price
$834,450
26 active listings
Median Closed Price
$587,500
88 sales
Median Days on Market
45
26 active listings
Median $ / Sq Ft
$302
26 active listings
Sale-to-List Ratio
99.0%
88 sales
How this home compares
List Price
$895,000
vs $834,450 median
7.3% above median
Price / Sq Ft
$392
vs $302 median
29.8% above median
Days on Market
82 days
vs 45 days median
37 days longer than median
Based on 26 active and 88 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of July 28, 2026.
Location
253 Bacon Pond Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,563
- Property Taxes$692
- Insurance$298
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Antique
- Year Built
- 1850
- New Construction
- No/Resale
- Living Area
- 2,283 sq ft
Schools
- Elementary
- Mitchell
- High
- Nonnewaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- Half Bath Laundry Combo off Kitchen
- Appliances
- Gas Range
- Basement
- Crawl SpacePartialInterior AccessPartial With Hatchway
- Interior Features
- Cable - AvailableSecurity System
Exterior & Lot
- Lot Size
- 3.19 acres
- Zoning
- OS60
- Garage / Parking
- 2 garage spaces5 total parking spacesBarnDrivewayGravel
- Waterfront
- Direct waterfront
- Waterfront Details
- Brook
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- Barn Red
- Roof
- Asphalt Shingle
- Foundation
- BlockStone
- Exterior Features
- BarnGuttersGarden AreaLightingStablePatio
- Lot Description
- Sloping LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $8,308 / Annually
- Days on Market
- 82
- MLS #
- 24172742
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:10 AM UTC.