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$599,900

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 1,658 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 153 Old Sherman Hill Rd

General

  • Price: $599,900
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24194640
  • Updated: 9/4/2026
  • Added to Site: 46 day(s) ago

Interior

  • Number of Rooms: 7
  • Appliances: Oven/Range, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Built-Ins, Hardwood Floor, Main
  • Kitchen: Kitchen, Main
  • Dining Room: Dining Room, Main
  • Other Room 1: Other, Main

Exterior

  • Exterior Features: Shed, Porch, Barn, Guest House

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Barn, Detached Garage

Location

  • County: Litchfield
  • Neighborhood: Sherman Hill
  • Driving Directions: Corner of Sage and Old Sherman Hill.

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Community

  • Community Name: Sherman Hill

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Tank Size Unknown

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial, Victorian
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Unfinished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,658
  • Above Ground: 1,658 Sq. Ft.
  • Year Built: 1903

Lot Features

  • Lot Size (Acres): 3.51
  • Zoning: OS60
  • Lot Description: Lightly Wooded, Level Lot, Open Lot

Financial Considerations

  • Assessment Amount: $315,350
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 932823
Buyer's Brokerage Compensation: 2.5%
Not binding unless confirmed by separate agreement among applicable parties.

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— 153 Old Sherman Hill Rd —

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 153 Old Sherman Hill Rd

School District:Regional School District 14
NameGradesDistance
Mitchell Elementary School
14 School Street, Woodbury, CT 06798
PK-51.6 mi
Woodbury Middle School
67 Washington Avenue, Woodbury, CT 06798
6-81.8 mi
Nonnewaug High School
5 Minortown Road, Woodbury, CT 06798
9-122 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 153 Old Sherman Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/04/2026
Price Reduced
$599,900
-14.29%
MLS
8/17/2026
Price Reduced
$699,900
-6.68%
MLS
8/10/2026
Listed
$750,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 153 Old Sherman Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,449
2%
$315,350
—
2023
$7,307
3%
$315,350
29%
2023
$7,102
—
$244,380
—
2022
$7,129
—
$244,380
—
2021
$7,129
—
$244,380
—
2020
$7,129
—
$244,380
—
2019
$7,129
3%
$244,380
-6%
2018
$6,937
-2%
$260,980
—
2017
$7,088
3%
$260,980
—
2016
$6,861
1%
$260,980
—
2015
$6,804
1%
$260,980
—
2014
$6,705
3%
$260,980
-6%
2011
$6,494
—
$277,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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153 Old Sherman Hill Road, Woodbury, CT 06798 (MLS# 24194640) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 153 Old Sherman Hill Road is currently listed for $599,900 and was received on August 10, 2026. This property is listed by Heather Weber from our Oxford Office.Want to learn more about 153 Old Sherman Hill Road? Do you have questions about finding other Single Family real estate for sale in Woodbury? You can browse all Woodbury real estate or contact a Coldwell Banker agent to request more information.

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