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153 Old Sherman Hill Road, Woodbury, CT 06798

Single Family For Sale

$599,900
$362/sqft
153 Old Sherman Hill Road, Woodbury, CT
Active
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3
Bedrooms
2
Bathrooms
1,658
Sq Ft
3.51
Acres
1903
Year Built

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.

Listed by Heather Weber (203) 232-5483 with Coldwell Banker Realty (203) 888-1845

Listing Snapshot

Price $599,900 Days on Our Site 36 days
Property Tax $7,896/yr Style Colonial,Victorian
Year Built 1903 Total Sq Ft 1,658
Lot Size 3.51 acres HOA Fees N/A
Bedrooms 3 Full Bathrooms 1
Total Rooms 7 Half Baths 1

Key Features

Appliances
  • Oven/Range
  • Refrigerator
  • Dishwasher
Outdoor
  • Shed
  • Porch
  • Barn
  • Guest House

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Barn, Detached Garage

Systems & Utilities

Heat Hot Air
Fuel Oil
Cooling None
Hot Water Tank Size Unknown
Water Private Well
Sewer Septic

Schools

Elem Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $658/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Sep 4, 2026 Price Reduced $599,900
Aug 10, 2026 Listed $750,000

Frequently Asked Questions

How much does 153 Old Sherman Hill Road in Woodbury, CT cost?
This property is listed at $599,900, which works out to $362 per square foot.
How many bedrooms does 153 Old Sherman Hill Road have?
This home has 3 bedrooms and 2 bathrooms.
What is the square footage of 153 Old Sherman Hill Road?
The home is 1,658 square feet, situated on 3.51 acres.
When was 153 Old Sherman Hill Road in Woodbury built?
This property was built in 1903.
Is 153 Old Sherman Hill Road, Woodbury, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 153 Old Sherman Hill Road, Woodbury in?
This home is served by the Woodbury public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 153 Old Sherman Hill Road, Woodbury, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Heather Weber · (203) 232-5483

Coldwell Banker Realty · (203) 888-1845

MLS# 24194640 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Sep 4, 2026 5:14 PM UTC