99 Old Sherman Hill Road
Woodbury, Connecticut 06798
Reduced from $589,000
- Beds
- 2
- Baths
- 2 | 1
- SqFt
- 2,034
- Acres
- 3.00
- Year Built
- 1690
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
- 1244 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
Active Listings
34
16 under contract
Median List Price
$812,000
34 active listings
Median Closed Price
$590,000
95 sales
Median Days on Market
64
34 active listings
Median $ / Sq Ft
$318
34 active listings
Sale-to-List Ratio
100.0%
95 sales
How this home compares
List Price
$389,900
vs $812,000 median
52.0% below median
Price / Sq Ft
$192
vs $318 median
39.6% below median
Days on Market
1244 days
vs 64 days median
1180 days longer than median
Based on 34 active and 95 closed sales (trailing 12 mo) of single family in Woodbury. Source: SmartMLS · As of October 22, 2026.
Location
99 Old Sherman Hill Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: indicative defaultsper month
- Principal & Interest$2,002
- 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
- 1244
- MLS #
- 170572367
- MLS Status
- Under Contract
Similar Properties
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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 10/22/2026. 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 10/22/2026 at 12:30 AM UTC.