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.
Sold for $401,597
$401,597
99 Old Sherman Hill Road, Woodbury, CT 06798
2beds
2,034sqft
Single Family Residence
Built in 1690
3 Acres Lot
$494,400 Zestimate®
$197/sqft
$3,142 Estimated rent
Home value
$494,400
$465,000 - $529,000
$3,142/mo
Zestimate® history
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List your homeWhat's special
Historic glebe houseCoffee shopsCommunity theaterWide board floorsGourmet restaurantsPlank wallsLeroy anderson museum
Zillow last checked:
Listing updated:
Listed by:
Joyce Drakeley 203-449-3568,
Drakeley Real Estate, Inc. 203-263-4336
Bought with:
Joyce Drakeley, REB.0193575
Drakeley Real Estate, Inc.
Source: Smart MLS,MLS#: 170572367
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Bedroom
- Features: Beamed Ceilings, Full Bath, Wide Board Floor
- Level: Upper
- Area: 144 Square Feet
- Dimensions: 12 x 12
Bedroom
- Features: Beamed Ceilings, Wide Board Floor
- Level: Upper
- Area: 234 Square Feet
- Dimensions: 13 x 18
Dining room
- Features: Fireplace, Wide Board Floor
- Level: Main
- Area: 221 Square Feet
- Dimensions: 13 x 17
Family room
- Features: Beamed Ceilings, Bookcases, Fireplace, Wide Board Floor
- Level: Main
- Area: 297 Square Feet
- Dimensions: 11 x 27
Kitchen
- Features: Beamed Ceilings
- Level: Main
- Area: 88 Square Feet
- Dimensions: 8 x 11
Living room
- Features: Beamed Ceilings, Bookcases, Fireplace, Wide Board Floor
- Level: Main
- Area: 234 Square Feet
- Dimensions: 13 x 18
Other
- Features: Wide Board Floor
- Level: Third,Other
Other
- Features: Wide Board Floor
- Level: Third,Upper
Heating
- Forced Air, Oil
Cooling
- None
Appliances
- Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater
- Laundry: Lower Level
Features
- Entrance Foyer
- Windows: Storm Window(s)
- Basement: Unfinished,Interior Entry,Hatchway Access
- Attic: Walk-up,Finished,Floored
- Number of fireplaces: 3
Interior area
- Total structure area: 2,034
- Total interior livable area: 2,034 sqft
- Finished area above ground: 2,034
Property
Parking
- Total spaces: 1
- Parking features: Detached, Barn, Covered, Private, Driveway
- Garage spaces: 1
- Has uncovered spaces: Yes
Features
- Fencing: Partial
Lot
- Size: 3 Acres
- Features: Open Lot, Secluded, Few Trees, Sloped
Details
- Additional structures: Barn(s), Shed(s), Stable(s)
- Parcel number: 935409
- Zoning: OS60
- Horse amenities: Paddocks
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Saltbox
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Stone
- Roof: Wood
Condition
- New construction: No
- Year built: 1690
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Green energy
- Energy efficient items: Windows
Community & neighborhood
Community
- Community features: Golf, Health Club, Library, Medical Facilities, Playground, Private School(s), Stables/Riding, Tennis Court(s)
Location
- Region: Woodbury
- Subdivision: Sherman Hill
Price history
| Date | Event | Price |
|---|---|---|
| 10/27/2023 | Sold | $401,597+3%$197/sqft |
Source:  Smart MLS #170572367 Report a problem | ||
| 10/18/2023 | Pending sale | $389,900$192/sqft |
Source: Smart MLS #170572367 Report a problem | ||
| 9/23/2023 | Price change | $389,900-13.2%$192/sqft |
Source: Smart MLS #170572367 Report a problem | ||
| 6/27/2023 | Price change | $449,000-9.8%$221/sqft |
Source: Smart MLS #170572367 Report a problem | ||
| 6/11/2023 | Price change | $498,000-15.4%$245/sqft |
Source: Smart MLS #170572367 Report a problem | ||
| 5/26/2023 | Listed for sale | $589,000$290/sqft |
Source: Smart MLS #170572367 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,116 -0.8% | $258,930 -2.7% |
| 2024 | $6,165 -10.8% | $266,070 +11.9% |
| 2023 | $6,913 -0.4% | $237,880 |
| 2022 | $6,939 | $237,880 |
| 2021 | $6,939 | $237,880 |
| 2020 | $6,939 | $237,880 |
| 2019 | $6,939 -1.3% | $237,880 -10.1% |
| 2018 | $7,031 -2.1% | $264,540 |
| 2017 | $7,185 +3.3% | $264,540 |
| 2016 | $6,955 | $264,540 |
Find assessor info on the county website
Neighborhood: 06798
Nearby schools
GreatSchools rating
- 5/10Mitchell Elementary SchoolGrades: PK-5Distance: 1.4 mi
- 6/10Woodbury Middle SchoolGrades: 6-8Distance: 1.6 mi
- 9/10Nonnewaug High SchoolGrades: 9-12Distance: 2.1 mi
Schools provided by the listing agent
- Elementary: Mitchell
- Middle: Woodbury
- High: Nonnewaug
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Litchfield County
- Woodbury
- 06798
- 99 Old Sherman Hill Road
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