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!
For sale
$2,100,000
225 Old Sherman Hill Road, Woodbury, CT 06798
4beds
4,517sqft
Est.:
Single Family Residence
Built in 1969
33.98 Acres Lot
$-- Zestimate®
$465/sqft
$-- HOA
What's special
Central airTall windowsSpacious deckSpacious composite deckCentral vacSecurity systemInground gunite saltwater pool
- 134 days
- on Zillow |
- 717 |
- 32 |
Zillow last checked: 7 hours ago
Listing updated: April 10, 2025 at 02:56pm
Listed by:
Maria Taylor,
Klemm Real Estate Inc,
Claudine McHugh,
Klemm Real Estate Inc
Source: Smart MLS,MLS#: 24072926

Travel times
Tour with a buyer’s agent
Tour with a buyer’s agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 208 Square Feet
- Dimensions: 13 x 16
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 108 Square Feet
- Dimensions: 9 x 12
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
- Area: 209 Square Feet
- Dimensions: 11 x 19
Bedroom
- Features: Built-in Features, Hardwood Floor
- Level: Upper
- Area: 242 Square Feet
- Dimensions: 11 x 22
Dining room
- Features: Beamed Ceilings, Sliders, Wide Board Floor
- Level: Main
- Area: 210 Square Feet
- Dimensions: 14 x 15
Family room
- Features: 2 Story Window(s), Cathedral Ceiling(s), Ceiling Fan(s)
- Level: Main
- Area: 625 Square Feet
- Dimensions: 25 x 25
Kitchen
- Features: Balcony/Deck, Breakfast Bar, Breakfast Nook, Kitchen Island
- Level: Main
- Area: 725 Square Feet
- Dimensions: 25 x 29
Living room
- Features: Cathedral Ceiling(s), Beamed Ceilings, Ceiling Fan(s), Gas Log Fireplace, Hardwood Floor
- Level: Main
- Area: 483 Square Feet
- Dimensions: 21 x 23
Office
- Features: Hardwood Floor
- Level: Main
- Area: 99 Square Feet
- Dimensions: 9 x 11
Other
- Features: Built-in Features
- Level: Main
- Area: 128 Square Feet
- Dimensions: 8 x 16
Rec play room
- Features: Fireplace
- Level: Lower
- Area: 460 Square Feet
- Dimensions: 20 x 23
Study
- Features: Balcony/Deck, Beamed Ceilings, Bookcases, Built-in Features, Gas Log Fireplace, Sliders
- Level: Main
- Area: 273 Square Feet
- Dimensions: 13 x 21
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Electric Cooktop, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater, Water Heater
- Laundry: Main Level
Features
- Central Vacuum
- Basement: Full,Partially Finished
- Attic: Floored,Pull Down Stairs
- Number of fireplaces: 2
Interior area
- Total structure area: 4,517
- Total interior livable area: 4,517 sqft
- Finished area above ground: 4,057
- Finished area below ground: 460
Property
Parking
- Total spaces: 4
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 4
Features
- Patio & porch: Deck, Patio
- Exterior features: Rain Gutters, Stone Wall
- Has private pool: Yes
- Pool features: Gunite, Salt Water, In Ground
Lot
- Size: 33.98 Acres
- Features: Few Trees, Borders Open Space, Level, Landscaped, Rolling Slope, Open Lot
Details
- Additional structures: Shed(s), Barn(s), Stable(s)
- Parcel number: 932924
- Zoning: OS80
- Other equipment: Generator
- Horses can be raised: Yes
- Horse amenities: Paddocks
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Vertical Siding, Wood Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1969
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Available
Green energy
- Energy efficient items: Thermostat
Community & HOA
Community
- Features: Basketball Court, Library, Park, Playground, Private School(s), Tennis Court(s)
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Woodbury
Financial & listing details
- Price per square foot: $465/sqft
- Tax assessed value: $665,210
- Annual tax amount: $15,413
- Date on market: 2/6/2025
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