153 Old Sherman Hill Road
Woodbury, Connecticut 06798
Reduced from $750,000
- Beds
- 3
- Baths
- 1 | 1
- SqFt
- 1,658
- Acres
- 3.51
- Year Built
- 1903
- Neighborhood
- Sherman Hill
- 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
Exceptional value and opportunity on 3.5 gorgeous acres! Bring this home back to its original charm. Features hardwood floors throughout and a cozy front porch. The upper level includes 3 bedrooms, a full bath, and access to a walk-up attic from the primary bedroom. The main level offers a half bath and a functional, open layout. Additional property highlights include a separate 962 sq. ft., 2-bedroom guest house-offering incredible potential for an in-law suite or rental income once renovated (appears to be separately metered). The property also features two massive, 2-story barns that appear to have electricity. Tremendous upside potential for an end-user, investor, or multi-generational living. Subject to probate approval. Property sold as-is; no disclosures.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- Sherman Hill
- Property / Style
- Single Family · Colonial,Victorian
- Year Built
- 1903
- Days on Market
- 49 days
- Beds
- 3
- Baths
- 1 full · 1 half
- Living Area
- 1,658 sq ft
- Lot Size
- 3.51 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,896 / Annually
Market Snapshot
The Woodbury Market
Single Family · trailing 12 months
Active Listings
35
14 under contract
Median List Price
$825,000
35 active listings
Median Closed Price
$580,000
95 sales
Median Days on Market
56
35 active listings
Median $ / Sq Ft
$335
35 active listings
Sale-to-List Ratio
99.5%
95 sales
How this home compares
List Price
$599,900
vs $825,000 median
27.3% below median
Price / Sq Ft
$362
vs $335 median
8.1% above median
Days on Market
49 days
vs 56 days median
7 days fresher than median
Based on 35 active and 95 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of September 28, 2026.
Location
153 Old Sherman Hill Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$3,203
- Property Taxes$658
- Insurance$200
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- Sherman Hill
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Victorian
- Year Built
- 1903
- New Construction
- No/Resale
- Living Area
- 1,658 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- None
- Appliances
- Oven/RangeRefrigeratorDishwasher
- Basement
- FullUnfinished
- In-Law Apartment
- PossibleDetached
Exterior & Lot
- Lot Size
- 3.51 acres
- Zoning
- OS60
- Garage / Parking
- 2 garage spacesBarnDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- ShedPorchBarnGuest House
- Lot Description
- Lightly WoodedLevel LotOpen Lot
Listing & Financials
- Property Taxes
- $7,896 / Annually
- Days on Market
- 49
- MLS #
- 24194640
- 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 9/28/2026. 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 9/28/2026 at 6:45 PM UTC.