Single Family For Sale
We'll notify you about price changes and updates to this listing.
Please fill in all fields.
No spam. Unsubscribe any time.
We'll notify you about any updates to this listing.
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, the home features 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & a 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 mahogany 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!
Listed by Stacey Matthews (203) 671-9067 with W. Raveis Lifestyles Realty (860) 868-0511
Estimate only. Contact a lender for accurate figures.
Stacey Matthews · (203) 671-9067
W. Raveis Lifestyles Realty · (860) 868-0511
MLS# 24167130 · Data provided by SmartMLS. Information deemed reliable but not guaranteed. Listing updated Apr 15, 2026 10:57 PM UTC
Interested in this property?
Get more information or schedule a showing.
$2,395,000
1030 Washington Woodbury Road, Roxbury
4 bd · 5 ba · 4,874 sf
77 Tophet Road, Roxbury
4 bd · 5 ba · 6,670 sf
$3,595,000
11 Ravenrock Road, Roxbury
4 bd · 6 ba · 7,063 sf
$2,045,000
88 Rucum Road, Roxbury
5 bd · 6 ba · 5,113 sf
$3,100,000
4 Sunrise Lane, Bridgewater
4 bd · 6 ba · 5,387 sf
Message sent!
We'll be in touch shortly.
Get more information about this property.
Please enter your first name and phone number.
By submitting, you consent to receive communications from RYZE Realty Group via phone, email, or text. You may opt out at any time.
Pick a tour type and suggest a date and time that works for you.
220 Painter Hill Road, Roxbury CT, 06783
$2,895,000 • Active
Tour requested!
We'll confirm your showing shortly.