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!

Interior

  • GeneralAuto Garage Door Opener, Cable - Available, Central Vacuum, Security System
  • AppliancesElectric Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • LaundryMain Level
  • BasementFull, Partially Finished
  • A/CCentral Air
  • HeatingHot Air, Oil
  • FireplaceFireplaces: 2
  • Half Baths1

Exterior

  • GeneralShed, Barn, Deck, Gutters, Stable, Stone Wall, Paddock, Patio
  • StyleContemporary
  • PoolGunite, Salt Water, In Ground Pool

Construction

  • RoofingAsphalt Shingle

Location

  • CountyLitchfield

Lot

  • ZoningOS80, 932924
  • RestrictionsEasements

Utilities

  • WaterPrivate Well
  • SewerSeptic

Listing History

  • 04/10/2025Off Market
  • 04/10/2025Off Market
  • 03/19/2025Active
  • 02/22/2025Backup
  • 02/06/2025$2,100,000 @ $465 per ft²
  • 02/06/2025Active
  • 08/15/2024$2,250,000 @ $498 per ft²
  • 08/15/2024Active
  • 08/08/2024$2,795,000 @ $619 per ft² 3.45%
  • 05/01/2024Active
  • 05/01/2024$2,895,000 @ $641 per ft²
  • 07/27/2017$2,250,000 @ $498 per ft²
  • 07/27/2017Sold

Property Features

  • 932924
  • Asphalt Shingle
  • Auto Garage Door Opener
  • Barn
  • Cable Available
  • Central Air
  • Central Vacuum
  • Contemporary
  • Deck
  • Easements
  • Fireplaces: 2
  • Full
  • Gunite
  • Gutters
  • Hot Air
  • In- Ground Pool
  • Litchfield
  • Main Level
  • Oil
  • OS80
  • Paddock
  • Partially Finished
  • Patio
  • Private Well
  • Salt Water
  • Security System
  • Septic
  • Shed
  • Stable
  • Stone Wall

    Property Info

    Property Details

    Address: 225 Old Sherman Hill Road, Woodbury, Connecticut 06798