153 Old Sherman Hill Road, Woodbury, Connecticut

$599,900

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3

Beds

2

Baths

1,658

Square feet

3.51

Acres

About 153 Old Sherman Hill Road

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.

Features of 153 Old Sherman Hill Road

MLS® # 24194640
Price $599,900
Bedrooms 3
Bathrooms 2.00
Full Baths 1
Half Baths 1
Square Footage 1,658
Acres 3.51
Type Single Family For Sale
Style Colonial, Victorian
Status Active

Community Information

Address 153 Old Sherman Hill Road
Area Sherman Hill
City Woodbury
County Litchfield
State Connecticut
Zip Code 06798

Amenities

Parking Barn, Detached Garage
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Appliances Oven/Range, Refrigerator, Dishwasher
Heating Hot Air, Oil
Cooling None
Fireplace No
Has Basement Yes
Basement Full, Unfinished

Exterior

Exterior Clapboard
Exterior Features Shed, Porch, Barn, Guest House
Lot Description Lightly Wooded, Level Lot, Open Lot
Roof Asphalt Shingle
Foundation Stone

School Information

Elementary Per Board of Ed
High Per Board of Ed

Additional Information

Date Listed August 10th, 2026
Days on Market 31
Zoning OS60
RE / Bank Owned No

Listing Details

OfficeColdwell Banker Realty

Listing Map

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Listing information last updated on September 11th, 2026 at 10:57am EDT.