225 Old Sherman Hill Road

Woodbury, CT 06798

  • $2,100,000
  • 4 Beds
  • 4/1 Baths
  • 4,517 Sqft
  • 33.98 Acres
  • 1969 Built

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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Property Highlights
  • STYLE : Contemporary
  • POOL : Yes
  • EXTERIOR FEATURES : Shed, Barn, Deck, Gutters, Stable, Stone Wall, Paddock, Patio
  • PRICE/SQFT : $465
  • DAYS ON MARKET : 15
  • MLS : 24072926

Additional Information

LOT DETAILS
  • ACRES: 33.98
  • ACRES SOURCE: Public Records
  • COUNTY: Litchfield
  • GAS DESCRIPTION: Oil
  • LOT DESCRIPTION: Lightly Wooded, Borders Open Space, Level Lot, Professionally Landscaped, Rolling, Open Lot
  • OCCUPANCY: Owner
  • WATER DESCRIPTION: Private Well
  • WATER FRONTAGE: Not Applicable
  • WATERFRONT DESCRIPTION: Not Applicable
EXTERIOR FEATURES
  • EXTERIOR FEATURES: Shed,Barn,Deck,Gutters,Stable,Stone Wall,Paddock,Patio
  • EXTERIOR SIDING: Vertical Siding, Wood
  • POOL DESCRIPTION: Gunite, Salt Water, In Ground Pool
  • ROOF: Asphalt Shingle
INTERIOR FEATURES
  • AIR CONDITIONING: Central Air
  • APPLIANCES INCLUDED: Electric Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • ATTIC: Yes
  • BEDS: 4
  • COOLING: Central Air
  • FIREPLACES: 2
  • FULL BATHS: 4
  • FURNACE TYPE: Oil
  • HALF BATHS: 1
  • HEAT: Oil
  • HEAT FUEL: Oil
  • HOT WATER: Electric, Domestic, 50 Gallon Tank
  • LAUNDRY ROOM: Main Level
  • LAUNDRY ROOM ACCESS: Off Kitchen
  • ROOMS: 11
  • TOTAL BATHS: 5
AMENITIES
  • Library
  • Park
  • Playground/Tot Lot
  • Private School(s)
  • Tennis Courts
  • Auto Garage Door Opener
  • Cable - Available
  • Central Vacuum
  • Security System
ADDITIONAL INFORMATION
  • ATTIC DESCRIPTION: Floored, Pull-Down Stairs
  • AVERAGE DAYS ON MARKET: 14
  • BASEMENT DESCRIPTION: Full, Partially Finished
  • DAYS ON MARKET: 15
  • ELEMENTARY SCHOOL: Per Board of Ed
  • ENCUMBRANCES: Easements
  • GARAGE: Attached Garage
  • HAS POOL?: Yes
  • HIGH SCHOOL: Nonnewaug
  • IS OCCUPIED?: Owner
  • JUNIOR HIGH SCHOOL: Woodbury
  • LIVING AREA SQFT: 4,517
  • PROPERTY TAX: $15,413
  • RESTRICTIONS: Easements
  • SEWER: Septic
  • STATUS: Active
  • STYLE: Contemporary
  • TYPE: Single Family For Sale
  • YEAR BUILT: 1969
  • YEAR BUILT DETAILS: Public Records
  • ZONING: OS80

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Location for 225 Old Sherman Hill Road, Woodbury, CT

Schools for 225 Old Sherman Hill Road, Woodbury, CT

Our community offers residents access to a number of fine private and public schools for all grade levels. Please read below for information on each of the schools in our area.

Private Schools
SCHOOL LOCATION GRADE
Creative Arts Studio 122 South Pomperaug Avenue, Woodbury, CT, 06798 PK-K
Brown Tufts Montessori 4 Church Street, Woodbury, CT, 06798 PK-K
Westover School 1237 Whittemore Road, Middlebury, CT, 06762 9-12
Reg 15 Bas Child Care Center-Pomperaug 129 Wheeler Road, Middlebury, CT, 06762 PK-K
First Step Pre-School 28 Heritage Crest Drive, Southbury, CT, 06488 PK-K
Great Expectations Dc-Learning Center 1235 Southford Rd, Southbury, CT, 06488 PK-K
First Steps Learning Center 1486 Seymour Road, Southbury, CT, 06488 PK-K
Generali School Child Care Center-Lit & Arts 1625 Straits Turnpike, Middlebury, CT, 06762 PK-K
Creative Arts Studio 122 South Pomperaug Avenue, Woodbury, CT, 06798 PK-K
Brown Tufts Montessori 4 Church Street, Woodbury, CT, 06798 PK-K
Westover School 1237 Whittemore Road, Middlebury, CT, 06762 9-12
Reg 15 Bas Child Care Center-Pomperaug 129 Wheeler Road, Middlebury, CT, 06762 PK-K
First Step Pre-School 28 Heritage Crest Drive, Southbury, CT, 06488 PK-K
Great Expectations Dc-Learning Center 1235 Southford Rd, Southbury, CT, 06488 PK-K
First Steps Learning Center 1486 Seymour Road, Southbury, CT, 06488 PK-K
Generali School Child Care Center-Lit & Arts 1625 Straits Turnpike, Middlebury, CT, 06762 PK-K
GreatSchools

*UG = ungraded.
Detailed school information provided by GreatSchools.org © 2025. All rights reserved.

Public and private school information is provided by sources including GreatSchools.org and various MLS services including the One Key, SMARTMLS, NCMLS, DARMLS and Greenwich MLS, and is subject to the terms of use on those sites. William Pitt and Julia B. Fee Sotheby’s International Realty believes the information provided by these sources to be accurate but will not be held responsible if any data as well as information such as school districts for listings is inaccurate.

Community

Woodbury>

Woodbury

Litchfield County, Connecticut

The Litchfield County town of Woodbury is known as a prime destination for antiques shoppers, having earned the title of “Antiques Capital of Connecticut.” Its quaint town center hosts numerous antiques...

Market Stats for Woodbury, Connecticut

An exclusive report that informs you of residential real estate sales activity and trends in Woodbury, Connecticut.

Request More Info for 225 Old Sherman Hill Road, Woodbury, CT

  • Kent Brokerage

    9 Maple Street , PO Box 82
    Kent, CT 06757
    O
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