220 Painter Hill Road, Roxbury, CT 06783

• 4 beds |
• 5 baths |
• 4,570 sqft

Property Description

Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece, appointed with premium appliances, a walk-in pantry, oversized island, and stylish bar. It opens seamlessly to a spacious screened porch with inviting dining and lounge areas. Outdoor living is elevated by an expansive ipe deck that functions as a true open-air great room-ideal for al fresco gatherings. The dining room extends to a charming sunset porch adorned with a pergola and irrigated herb garden. The grounds are equally impressive, with professionally designed landscaping that includes an apple orchard, restored stone walls, and a picturesque pond with cascading waterfall. A striking custom pool features a lap lane, lounging platform, and firepit with integrated stone seating, creating a private resort-like setting. Addl highlights include a 3,000-bottle wine cellar, heated garage, pergola-covered carport, and a newly finished oil-and-stone driveway. Ideally located just minutes from the chic shops & fine dining of Washington and Woodbury. Nearby land trust trails offer plentiful hiking. This turnkey property offers easy access to the very best of Litchfield County! Agent Owner.

Listing Status:

Active

Date Added:

April 15, 2026

Data Last Updated:

May 12, 2026 at 12:52AM

Listing Office:

W. Raveis Lifestyles Realty : (860) 868-0511

Listing Agent:

Stacey Matthews : (203) 671-9067

MLS ID:

24167130

Interior

• General: Auto Garage Door OpenerElevatorOpen Floor PlanSecurity System
• Rooms: FoyerLaundry RoomMud RoomSitting RoomWine Cellar
• Appliances: Gas RangeMicrowaveRange HoodSubzeroDishwasherWasherDryerWine Chiller
• Laundry: Main Level
• Basement: FullPartially Finished
• A/C: Central Air
• Heating: Heat PumpHot AirZonedElectricOilPropane
• Fireplace: Fireplaces: 1

Exterior

• General: Porch-ScreenedUnderground UtilitiesPorchDeckGarden AreaStone WallFrench DoorsUnderground SprinklerPatio
• Style: Colonial
• Pool: GuniteHeatedSalt WaterLap PoolIn Ground Pool

Construction

• Roofing: Asphalt ShingleMetal

Location

• County: Litchfield

Lot

• Zoning: C867195

Utilities

• Water: Private Well
• Sewer: Septic