#24049803, Timothy Drakeley, Listing office: Drakeley Real Estate, Inc.

225 Old Sherman Hill Rd Woodbury, CT 06798
Property details
About 225 Old Sherman Hill Rd
A long winding drive leads you to Four Winds Farm. Perched on the hill, this remarkable 33.98-acre property includes a 4,500 sq ft, 11 room, 4 bedrooms, 4.1 bath residence as well as a home for your horses. The contemporary house has many updates throughout, cathedral ceilings, tall windows, multiple sliders to exterior entertainment areas and spacious deck. There is central air, a security system, central vac, generator, and 4-bay heated garage. The spectacular grounds include the inground gunite saltwater pool, spacious composite deck, mature professional landscaping, and amazing views of distant hills. For the horses there is a two-story 8 stall stable, 14 paddocks with aisle ways, 120' x 200' riding ring with Atwood Equestrian Surface (re-surfaced 4 years ago), 7 run-in sheds, 20' x 20' tractor barn and trail. Woodbury designated as Connecticut's "Most charming small town," by Reader's Digest offers tree-lined Main St, parks, playgrounds, hiking trails and streams to dip your toes in on those hot summer days. Also known as the "Antiques Capital of CT," there's no shortage of shops, boutiques and antiques homes lining the historic district. Woodbury is home to a half dozen fun and diverse restaurants and a brewery with music. Just twenty minutes to the historic Palace Theater for concerts, comedy and much more. Forty minutes to Mohawk Mountain for winter fun. 35 minutes to Brewster Train Station and 90 minutes to NYC. Come see what Litchfield Hills has to offer!
Highlights
Summary
- Partial Bathrooms: 1
- Full Bathrooms: 4
- Appliances: Electric Cooktop, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
- Basement: Yes
- Interior: Auto Garage Door Opener, Cable - Available, Central Vacuum, Security System
- Total Bedroom Count: 4
- Garage Space: 4 spaces
- Attached Garage: Yes
- Private Pool: Yes
- Parking: Attached Garage
- View: Trees/Woods
- Exterior: Shed, Barn, Deck, Gutters, Stable, Stone Wall, Paddock, Patio
- Architectural Style: Contemporary
- Heating: Forced Air
- Cooling: Central Air
- List Price: $2,100,000
- Price/SqFt: $464
- Annual Tax Amount: $15,413
- Tax Year: 2024
- Lot: Wooded, Level, Landscaped, Rolling/Hilly, Open Lot
- Directions: Rte 6 to Rte 64 towards Middlebury. Take right on Old Sherman Hill. Property on the left.
- Year Built: 1969
- Living Area: 4,517 SqFt
- Lot Size: 33.98 Acres
- MLS Number: 24072926
- Office Name: Klemm Real Estate Inc
- Office Phone: (860) 868-7313
- Office Email: mtaylor1800@aol.com
- Listing Agent: Maria Taylor
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Last updated on: 7/8/2025, 4:45:31 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
Date | Event | Price |
---|---|---|
Aug 08, 2006 | Home Sold | $2,525,000 |
Sep 25, 2000 | Home Sold | $2,225,000 |
Tax history
Year | Assessment | Property Tax |
---|---|---|
2024 | $665,210 | $15,413 |
2023 | $526,020 | $15,286 |
2022 | $526,020 | $15,344 |
2021 | $526,020 | $15,344 |
2020 | $526,020 | $15,344 |
2019 | $526,020 | $15,344 |
History based on county public records data.
Nearby schools
7
Mitchell Elementary School
Public District PK-5
1.9 mi
•14 School St
8
Long Meadow Elementary School
Public District PK-5
2.3 mi
•65 N Benson Rd
7
Gainfield Elementary School
Public District KG-5
3.8 mi
•307 Old Field Rd
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $74,643. The majority of Woodbury, CT residents have income between $35k-100k annually. Most families are single, no kids. Residents of this area typically have post secondary degree education.
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Frequently asked questions
About 225 Old Sherman Hill Rd
The listing price of 225 Old Sherman Hill Rd property is $2,100,000.
The property 225 Old Sherman Hill Rd is a house located in Woodbury, Connecticut, 06798.
Active Listing: 225 Old Sherman Hill Rd is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 225 Old Sherman Hill Rd are: Mitchell Elementary School (GreatSchools Rating 7/10), Long Meadow Elementary School (GreatSchools Rating 8/10), Gainfield Elementary School (GreatSchools Rating 7/10), Woodbury Middle School (GreatSchools Rating 8/10), Rochambeau Middle School (GreatSchools Rating 5/10), Memorial Middle School (GreatSchools Rating 5/10), Nonnewaug High School (GreatSchools Rating 7/10), Pomperaug Regional High School (GreatSchools Rating 8/10), Watertown High School (GreatSchools Rating 4/10).
According to the records, the last property tax for 2024 is $15,413 (source: MLS/based on county public records data).
The last sale was on August 8, 2006 for $2,525,000 (source: MLS/tax record).
The property at 225 Old Sherman Hill Rd has 4 bedrooms and 4 full and 1 half bathrooms.
The property 225 Old Sherman Hill Rd is 4,517 SqFt (source: MLS/tax record).
The year of construction for 225 Old Sherman Hill Rd is 1969.
This home is located at 225 Old Sherman Hill Rd in Woodbury, CT and zip code 06798. This 4,517 square foot home, which was built in 1969, sits on a 33.98 acre lot. Features: 4 bedrooms, 5 bathrooms. It has been listed on Rocket Homes since February 6, 2025 and is currently priced at $2,100,000.
In June 2025 more than 3 listings in Woodbury, CT were sold above the asking price. During the same period more than 1 listings were sold at asking price, while more than 1 were sold below. The inventory of homes for sale in Woodbury, CT between May and June 2025 increased by 13.1%.