#24049803, Timothy Drakeley, Listing office: Drakeley Real Estate, Inc.
#24072926·
Listing office: Klemm Real Estate Inc·
Listing agent: Maria Taylor·
Listing office phone: (860) 868-7313
$2,100,000 List price
225 Old Sherman Hill Rd Woodbury, CT 06798
4 beds
4 full, 1 partial
4,517 sqft
34.0 acres
$465 / sqft
House
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
Home typeOther
HeatingForced Air
StatusActive
CoolingCentral Air
Size4,517 sqft
BasementYes
Lot size33.98 Acres
Year built1969
ParkingAttached Garage
MLS #24072926
Attached garage4 spaces
ViewTrees/Woods
Private poolYes
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
Copyright © 2025 Smart MLS. The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 7/30/2025, 12:45:30 AM 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. Typical family type is single, no kids. Residents of this area typically have post secondary degree education.
How much money do the neighbors make?
24%
<35k
38%
35k-100k
25%
100k-200k
13%
200k+
What level of education do the neighbors have?
No High School
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
51%
Single, No Kids
5%
Single, with Kids
28%
Married, No Kids
16%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
10%
<11 yrs old
7%
12-17 yrs old
14%
18-34 yrs old
46%
35-64 yrs old
23%
65+ yrs old
What do the neighbors do for fun?
Skiing/snowboarding
PGA/LPGA
Figure Skating
Where do the neighbors shop?
BJs Wholesale Club
Stein Mart
Kmart
Where do the neighbors go to eat?
Panera
Cracker Barrel
Bob Evans
What do the neighbors drive?
Infiniti
Lexus
Lincoln
What do the neighbors listen to?
Adult Hits
Oldies
News/Talk/Information
All data provided by Home Junction and Claritas
Similar homes for sale
#24086901, Michael Vartolone, Listing office: William Raveis Real Estate
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. In June 2025 in Woodbury, CT there were 13.1% more homes for sale than in May.
From Rocket Homes Real Estate and based on county public records data.