For sale

Price cut: $100K (10/1)

$499,900

153 Old Sherman Hill Road, Woodbury, CT 06798

3beds

1,658sqft

$3,650/mo

Get pre-qualified

Single Family Residence

Built in 1903

3.51 Acres Lot

$-- Zestimate^®

$302/sqft

$-- HOA

What's special

Cozy front porchHardwood floors throughout

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.

58 days
1,096
96

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 2
Full bathrooms: 1
1/2 bathrooms: 1

Primary bedroom

Features: Hardwood Floor
Level: Upper

Bedroom

Features: Hardwood Floor
Level: Upper

Bedroom

Features: Hardwood Floor
Level: Upper

Dining room

Level: Main

Kitchen

Level: Main

Living room

Features: Built-in Features, Hardwood Floor
Level: Main

Other

Level: Main

Heating

Forced Air, Oil

Cooling

None

Appliances

Included: Oven/Range, Refrigerator, Dishwasher

Features

Basement: Full,Unfinished
Attic: Walk-up
Has fireplace: No

Interior area

Total structure area: 1,658
Total interior livable area: 1,658 sqft
Finished area above ground: 1,658

Property

Parking

Total spaces: 2
Parking features: Barn, Detached
Garage spaces: 2

Features

Patio & porch: Porch

Lot

Size: 3.51 Acres
Features: Few Trees, Level, Open Lot

Details

Additional structures: Shed(s), Barn(s), Guest House
Parcel number: 932823
Zoning: OS60

Construction

Type & style

Home type: SingleFamily
Architectural style: Colonial,Victorian
Property subtype: Single Family Residence

Materials

Clapboard
Foundation: Stone
Roof: Asphalt

Condition

New construction: No
Year built: 1903

Utilities & green energy

Sewer: Septic Tank
Water: Well

Community & HOA

Community

Subdivision: Sherman Hill

HOA

Has HOA: No

Location

Region: Woodbury

Financial & listing details

Price per square foot: $302/sqft
Tax assessed value: $315,350
Annual tax amount: $7,896
Date on market: 8/10/2026

Estimated market value

Not available

Estimated sales range

Not available

Price history

Date	Event	Price
10/1/2026	Price change	$499,900-16.7%$302/sqft
Source: Smart MLS #24194640 Report a problem
9/4/2026	Price change	$599,900-14.3%$362/sqft
Source: Smart MLS #24194640 Report a problem
8/17/2026	Price change	$699,900-6.7%$422/sqft
Source: Smart MLS #24194640 Report a problem
8/10/2026	Listed for sale	$750,000+333.5%$452/sqft
Source: Smart MLS #24194640 Report a problem
6/17/1985	Sold	$173,000$104/sqft
Source: Agent Provided Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$7,449 +1.9%	$315,350
2024	$7,307 +2.9%	$315,350 +29%
2023	$7,102 -0.4%	$244,380
2022	$7,129	$244,380
2021	$7,129	$244,380
2020	$7,129	$244,380
2019	$7,129 +2.8%	$244,380 -6.4%
2018	$6,937 -2.1%	$260,980
2017	$7,088 +3.3%	$260,980
2016	$6,861 +0.8%	$260,980
2015	$6,804 +1.5%	$260,980
2014	$6,705 +3.2%	$260,980 -6%
2013	$6,494 -3.4%	$277,500
2012	$6,724 +7.9%	$277,500
2011	$6,233 +4.7%	$277,500
2010	$5,952 +1.5%	$277,500
2009	$5,864 +14.4%	$277,500 +31.8%
2008	$5,126 +1.6%	$210,530
2007	$5,044	$210,530