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99 Old Sherman Hill Road

Woodbury, Connecticut 06798

PENDING$389,900

Reduced from $589,000

Beds
2
Baths
2 | 1
SqFt
2,034
Acres
3.00
Year Built
1690
Matt Caiola

Matt Caiola

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About This Home

Built circa 1690 as one of the oldest homes in Woodbury. Beautifully sited it is a typical saltbox with plank walls, stone chimney, wide board floors, three large fireplaces with ovens at the back of two and much original wainscot. A new septic system is presently being installed. It seems to have been changed relatively little inside. The joiner's shop is still standing on the property with a one car garage underneath easily accessible. Adjacent to the large field sits an oversized barn with 3 stalls in the lower level and plenty of space on the first and second floors of this barn. In the back is a large wood shed with an attached outhouse plus a spacious dog house and run. Located minutes and within walking distance to the town center and coffee shops, gourmet restaurants, shopping, gardens and sidewalks. The New York Times in the Living In page referred to Woodbury as Peace, Quaint Beauty and a Sense of History and the Reader's Digest called it the best small town in Connecticut. Located only 1 1/2 hrs by car to NYC and 1/2 hr to the train station. Nearby is the community theater, LeRoy Anderson museum, historic Glebe House, concerts in the churches and parks, library, gyms, medical facilities and so much more.

Key Facts

City/Town
Woodbury
Property / Style
Single Family · Saltbox
Year Built
1690
Days on Market
1160 days
Beds
2
Baths
2 full · 1 half
Living Area
2,034 sq ft
Lot Size
3.00 acres
Property Taxes
Not on file from MLS

Market Snapshot

The Woodbury Market

Single Family · trailing 12 months

Median Days on Market

53

24 active listings

Median $ / Sq Ft

$296

24 active listings

Sale-to-List Ratio

99.0%

88 sales

How this home compares

List Price

$389,900

vs $857,000 median

54.5% below median

Price / Sq Ft

$192

vs $296 median

35.1% below median

Days on Market

1160 days

vs 53 days median

1107 days longer than median

Based on 24 active and 88 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of July 29, 2026.

Location

99 Old Sherman Hill Road, Woodbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,118

per month

  • Principal & Interest$1,988
  • Property Taxes$0
  • Insurance$130
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Woodbury
County
Litchfield

Residence

Property Type
Single Family
Style
Saltbox
Year Built
1690
Living Area
2,034 sq ft

Schools

Elementary
Mitchell
High
Nonnewaug

Interior

Heating
Hot Air
Cooling
None
Fireplaces
3
Laundry
Lower Level
Additional Rooms
Foyer

Exterior & Lot

Lot Size
3.00 acres
Garage / Parking
Detached GarageBarnCovered Garage
Waterfront Details
Not Applicable
Construction
Clapboard
Roof
Wood Shingle
Foundation
Stone
Exterior Features
BarnPaddockShedStable
Lot Description
Open LotSecludedLightly WoodedSloping LotFence - Partial

Listing & Financials

Days on Market
1160
MLS #
170572367
MLS Status
Under Contract

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Joyce Drakeley

(203) 4493568

Drakeley Real Estate, Inc.

Buyer's Agent

Joyce Drakeley

Drakeley Real Estate, Inc.

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/29/2026 at 10:10 AM UTC.