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253 Bacon Pond Road

Woodbury, Connecticut 06798

ACTIVE$895,000
Beds
4
Baths
2 | 1
SqFt
2,283
Acres
3.19
Year Built
1850
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Waterfront2-Car Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,553

per 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

Similar Properties

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Listed By

Christian Jensen

(212) 604-9432

William Pitt Sotheby's Int'l

(860) 868-6600

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.