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$2,100,000
35 Days On Site

225 Old Sherman Hill Road
Woodbury, CT 06798

For Sale|Single Family Residence|Active Under Contract
4
Beds
4
Full Baths
1
Partial Bath
4,057
SqFt
$518
/SqFt
1969
Built
County:
Litchfield
Listing courtesy of Maria Taylor of Klemm Real Estate Inc
Call Now: 860.406.4060
Is this the home for you? We can help make it yours.
860.406.4060
225 Old Sherman Hill Road225 Old Sherman Hill Road225 Old Sherman Hill Road225 Old Sherman Hill Road
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Monthly Payment (Est.)

$9,581
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2025 Information is deemed reliable but not guaranteed.

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!

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Listing Snapshot
Price 
$2,100,000
Days On Site 
35 Days
Bedrooms 
4
Inside Area (SqFt) 
4,057 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
33.98 Acres
Year Built 
1969
MLS® Number 
24072926
Status 
Active Under Contract
Property Tax 
$15,413
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
3 weeks agoListing updated with changes from the MLS®
3 weeks agoStatus changed to Active Under Contract
a month agoListing first seen on site
General Features
Acres 
33.98
Attached Garage 
Yes
Foundation 
Concrete Perimeter
Garage 
Yes
Garage Spaces 
4
Parking 
Garage Door OpenerAttached
Property Sub Type 
Single Family Residence
Security 
Security System
Sewer 
Septic Tank
SqFt Total 
4517
Style 
Contemporary
Water Source 
Well
Zoning 
OS80
Interior Features
Appliances 
DishwasherDryerElectric CooktopMicrowaveRefrigeratorOvenWasherElectric Water Heater
Basement 
FullPartially Finished
Cooling 
Central Air
Fireplace 
Yes
Fireplaces 
2
Heating 
OilForced Air
Interior 
Central Vacuum
Laundry Features 
Main Level
Rec/Play Room 
Dimensions - 23 x 20Level - Lower
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Exterior Features
Construction Details 
Wood SidingFrameVertical Siding
Lot Features 
LevelRolling Slope
Other Structures 
Barn(s)Shed(s)
Patio And Porch 
DeckPatio
Pool Features 
GuniteOutdoor PoolSalt WaterIn Ground
Roof 
Asphalt
Community Features
Community Features 
Tennis Court(s)
Horse Allowed 
Yes
Horse Property 
Stable(s)
Schools
School District
Unknown
Elementary School
Per Board of Ed
Middle School
Woodbury
High School
Nonnewaug
Listing courtesy of Maria Taylor of Klemm Real Estate Inc



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. Copyright 2025 SmartMLS, Inc.

Neighborhood & Commute
Source: Walkscore
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