About 277 Painter Hill Road
This beautifully renovated 1911 colonial blends timeless charm with modern comfort in one of Roxbury's most desirable locations. The main residence offers luxury living with 2-3 bedrooms, a media room, gourmet kitchen, formal dining room, and a screened porch. The newly built guest house includes 2 bedrooms and a spacious game room/cabana with fireplace. Enjoy Summer entertaining on the covered porch with outdoor fireplace overlooking the heated gunite saltwater pool, scenic views, and expansive level lawn. The property features a two-car garage and borders a major estates and conserved land, ensuring privacy and beauty in an exceptional setting. Just minutes to the Mayflower Inn/Spa and chic shopping/dining in Washington and Woodbury.
Features of 277 Painter Hill Road
| MLS® # | 24138574 |
|---|---|
| Price | $2,547,500 |
| Bedrooms | 3 |
| Bathrooms | 2/1 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 2,559 |
| Acres | 3.12 |
| Type | Single Family For Sale |
| Style | Colonial |
| Status | Closed |
Community Information
| Address | 277 Painter Hill Road |
|---|---|
| Area | N/A |
| City | Roxbury |
| County | Litchfield |
| State | Connecticut |
| Zip Code | 06783 |
Amenities
| Features | Generator |
|---|---|
| Parking Spaces | 10 |
| Parking | Detached Garage, Driveway |
| Garage Spaces | 2 |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | Yes |
| Pool | In Ground Pool |
Interior
| Interior Features | Cable - Available |
|---|---|
| Appliances | Cook Top, Dishwasher, Freezer, Microwave, Oven/Range, Refrigerator, Subzero |
| Heating | Hot Air, Oil, Propane |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 3 |
Exterior
| Exterior | Clapboard, Wood |
|---|---|
| Exterior Features | Cabana, Lighting, Guest House, Covered Deck |
| Lot Description | Borders Open Space, Level Lot, Cleared, Professionally Landscaped, Open Lot |
| Roof | Wood Shingle, Metal |
| Foundation | Concrete, Stone |
School Information
| Elementary | Booth |
|---|---|
| High | Shepaug |
Additional Information
| Date Listed | November 14th, 2025 |
|---|---|
| Days on Market | 19 |
| Zoning | C |
| RE / Bank Owned | No |
Listing Details
| Office | W. Raveis Lifestyles Realty |
|---|