About 220 Painter Hill Road
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.
Features of 220 Painter Hill Road
| MLS® # | 24167130 |
|---|---|
| Price | $2,750,000 |
| Bedrooms | 4 |
| Bathrooms | 5.00 |
| Full Baths | 4 |
| Half Baths | 1 |
| Square Footage | 4,570 |
| Acres | 4.68 |
| Type | Single Family For Sale |
| Style | Colonial |
| Status | Active |
Community Information
| Address | 220 Painter Hill Road |
|---|---|
| Area | Painter Hill |
| City | Roxbury |
| County | Litchfield |
| State | Connecticut |
| Zip Code | 06783 |
Amenities
| Features | Generator, Humidistat, Programmable Thermostat, Ridge Vents, Thermopane Windows |
|---|---|
| Parking | Carport, Attached Garage |
| # of Garages | 3 |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | Yes |
| Pool | Gunite, Heated, Salt Water, Lap Pool, In Ground Pool |
Interior
| Interior Features | Auto Garage Door Opener, Elevator, Open Floor Plan, Security System |
|---|---|
| Appliances | Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller |
| Heating | Heat Pump, Hot Air, Zoned, Electric, Oil, Propane |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Has Basement | Yes |
| Basement | Full, Partially Finished |
Exterior
| Exterior | Clapboard, Hardie Board |
|---|---|
| Exterior Features | Porch-Screened, Underground Utilities, Porch, Deck, Garden Area, Stone Wall, French Doors, Underground Sprinkler, Patio |
| Lot Description | Fence - Stone, Lightly Wooded, Cleared, Professionally Landscaped, Open Lot |
| Roof | Asphalt Shingle, Metal |
| Foundation | Concrete |
School Information
| Elementary | Booth Free |
|---|---|
| High | Regional District 12 |
Additional Information
| Date Listed | April 15th, 2026 |
|---|---|
| Days on Market | 147 |
| Zoning | C |
| RE / Bank Owned | No |
Listing Details
| Office | W. Raveis Lifestyles Realty |
|---|