About this home

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. Owner is Agent

Facts and features

Schools

• Shepaug Valley School

  middle · 6-12 · 1.3 mi

  8

• Booth Free School

  elementary · K-5 · 2.3 mi

• The Gunnery

  high · 9-12 · 3.0 mi

• The Frederick Gunn School

  high · 9-12 · 3.1 mi

• Horace Mann School John Dorr Nature Laboratory

  elementary · 2-12 · 3.1 mi

• Washington Primary School

  elementary · K-5 · 3.8 mi

  9

Price history

• Jul 29, 2026 · Price Changed$2,750,000
• Apr 15, 2026 · Listed$2,895,000
• Jun 16, 2023 · Listing Removed—
• May 28, 2023 · Price Changed$2,695,000
• Apr 26, 2023 · Listed$2,795,000
• May 20, 2021 · Sold$700,000
• Sep 1, 2020 · Sold$650,000
• Jul 2, 2020 · Listing Removed—

Tax history

• 2026$10,164 tax · $781,830 assessed
• 2025$10,164 tax · $781,830 assessed
• 2023$9,872 tax · $783,510 assessed
• 2022$8,597 tax · $563,750 assessed
• 2021$8,530 tax · $553,880 assessed
• 2020$12,450 tax · $787,960 assessed
• 2019$12,489 tax · $787,960 assessed
• 2018$12,489 tax · $787,960 assessed

Home value

$2,722,000

• Collateral Analytics$2,722,000
• Cotality$2,739,600
• Quantarium$2,664,816

Where it is