Single Family For Sale
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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.
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 Aug 8, 2026 5:54 AM UTC
Peter & Konrad
Co-Founders, RYZE Realty Group
You'll work directly with Peter and Konrad on this home — never an assistant.
$3,495,000
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4 bd · 5 ba · 4,456 sf
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65 STOCKYARD Court, New Milford
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119 Judge Lane, Bethlehem
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220 Painter Hill Road, Roxbury CT, 06783
$2,750,000 • Active
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