153 Old Sherman Hill Road
Woodbury, CT 06798
$499,900 - Sherman Hill
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.
| Mls Number: | 24194640 |
|---|---|
| List Price: | $499,900 |
| Property Type: | Single Family |
| Beds Total: | 3 |
| Baths Full: | 1 |
| Baths Half: | 1 |
| Sq Ft Total: | 1,658 |
| Property Tax: | $7,896 |
| Acres: | 3.51 |
| Style: | Colonial,Victorian |
| City: | Woodbury |
| Neighborhood: | Sherman Hill |
| County Or Parish: | Litchfield |
| Postal Code: | 06798 |
| Year Built: | 1903 |
| Basement Description: | Yes |
| Directions: | Corner of Sage and Old Sherman Hill. |
| Exterior Features: | Shed, Porch, Barn, Guest House |
| Garages Number: | 2 |
| High School: | Per Board of Ed |
| Original List Price: | $750,000 |
| Parking Total Spaces: | 2 |
| Sewage System: | Septic |
| Tax Year: | July 2026-June 2027 |
| Waterfront Description: | Not Applicable |
| Water Source: | Private Well |
| Zoning: | OS60 |
| Acres Source: | Public Records |
| Agent Owner Yn: | No |
| Status: | Active |
| Appliances Included: | Oven/Range, Refrigerator, Dishwasher |
| Assessed Value: | $315,350 |
| Attic Description: | Walk-up |
| Attic Yn: | Yes |
| Basement Description: | Full,Unfinished |
| Baths Total: | 2 |
| Comp Only Manual Yn: | No |
| Cooling System: | None |
| Current Price: | $499,900.00 |
| Display Fair Market Value Yn: | No |
| Elementary School: | Per Board of Ed |
| Exterior Siding: | Clapboard |
| Foundation Type: | Stone |
| Fuel Tank Location: | In Basement |
| Garage & Parking: | Barn, Detached Garage |
| Heat Fuel Type: | Oil |
| Heat Type: | Hot Air |
| Home Owner's Assocation: | No |
| Home Warranty Offered Yn: | No |
| Hot Water Description: | Tank Size Unknown |
| In Law Access: | Detached |
| In Law Apartment: | Possible |
| Listing Contract Date: | 2026-08-10 |
| Lot Description: | Lightly Wooded, Level Lot, Open Lot |
| Mil Rate Total: | $25.04 |
| Status: | Active |
| New Construction Type: | No/Resale |
| Occupied By: | Vacant |
| Parcel Number: | 932823 |
| Possession Availability: | Negotiable |
| Potential Short Sale: | No |
| Preferred Phone: | (203) 232-5483 |
| Price: | $499,900 |
| Roof Information: | Asphalt Shingle |
| Sign Yn: | Yes |
| Sq Ft Description: | Sq Ft is for Main House only. |
| Sq Ft Est Heated Above Grade: | 1,658 |
| Sq Ft Total: | 1,658 |
| Swimming Pool Yn: | No |
| Total Rooms: | 7 |
| Under Agreement Yn: | No |
| Year Built Source: | Public Records |
Listing Courtesy of: Coldwell Banker Realty
Listing Agent: Heather Weber
(203) 232-5483
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Smart MLS Inc. data last updated on October 08, 2026 05:24 PM - ET
Property Last Updated: October 08, 2026 05:24 PM - ET
