Painter Hill Real Estate

Welcome to Painter Hill, a picturesque neighborhood nestled in the heart of Roxbury, Connecticut, within the scenic Litchfield County. Known for its enchanting landscapes and vibrant community spirit, Painter Hill is a hidden gem that perfectly blends rural charm with modern conveniences.

As you stroll through the tree-lined streets, you’ll be captivated by the stunning views of rolling hills and lush greenery that define this serene area. The neighborhood is characterized by its beautiful homes, many of which boast classic New England architecture, offering a sense of timeless elegance. Whether you're looking for a cozy cottage or a spacious family home, Painter Hill has something to suit every taste and lifestyle.

One of the highlights of living in Painter Hill is its close-knit community, where friendly neighbors greet you with a smile and local events bring everyone together. Enjoy the seasonal festivities, farmer’s markets, and art shows that celebrate the rich culture and creativity of the area. Outdoor enthusiasts will appreciate the nearby hiking trails, parks, and scenic spots perfect for picnics or leisurely walks.

Painter Hill is also conveniently located just a short drive from Roxbury’s charming town center, where you can find delightful shops, quaint cafes, and essential services. With its excellent schools and family-friendly atmosphere, Painter Hill is an ideal place for families looking to settle down in a peaceful yet vibrant community.

Experience the best of Connecticut living in Painter Hill, where every day feels like a retreat in nature, and community connection is at the heart of it all. Come and discover your dream home in this enchanting neighborhood!

Newest Listings in Painter Hill

$3,950,000

4 Beds ⋅ 7 Baths ⋅ 24192621 MLS

Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

297 Painter Hill Rd, Roxbury

$969,000

4 Beds ⋅ 3 Baths ⋅ 24167690 MLS

Mint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. New Anderson Luxe White Oak Windows. Wood-Burning Fireplace, Vaulted Primary Bedroom with Balcony and Private Bath. Dine or relax on the Flagstone Terrace. Must See!

23 Painter Hill Rd, Roxbury

$2,000,000

24170752 MLS

If You are looking for land with views to build your dream home, this is it. This is truly an "Estate Property". The 27 acres is cleared and open. There are several building sites at the top with 180 degree views. The land slopes gently down with a brook and 2 small ponds at the bottom. There is a fairly large barn and a smaller shop on the property in need of repairs. They are being sold AS IS! Bring your plans and build in a most beautiful part of the world in a sought after Connecticut town. Litchfield County is rural and beautiful. Enjoy farmers markets and country fairs. Visit any number of great restaurants in the area. There are many art shows, antique shops and boutiques to visit. As for outdoor activities, there are thousands of acres of land trust and hiking trails in Roxbury and surrounding towns. The Shepard River offers great fishing. There are ski areas close by as well as lakes for boating, fishing and swimming. Located under 2 hours from NYC! Taxes are based on 490 farming designation.

55 Ranney Hill Rd, Roxbury

$2,750,000

4 Beds ⋅ 5 Baths ⋅ 24167130 MLS

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.

220 Painter Hill Rd, Roxbury

$760,000

3 Beds ⋅ 3 Baths ⋅ 24132367 MLS

Tucked away on a long private road, this light and bright Roxbury retreat combines timeless character with modern comfort. The home features three spacious bedrooms and two and a half baths, thoughtfully designed for both everyday living and effortless entertaining. Soaring ceilings with exposed beams and abundant skylights fill the interior with natural light, highlighting the warmth of beautiful wood floors throughout. The open floor plan creates a sense of airiness and flow, while large windows bring the surrounding nature indoors. Whether you're relaxing in the peaceful primary bedroom or gathering in the inviting living area, every space feels serene and connected to the outdoors. The lower level offers 9'+ ceilings, windows and a walk-out. A rare opportunity to enjoy quiet country living just minutes from the heart of Roxbury - the perfect blend of rustic charm and contemporary style.

38 W Mountain Ln, Roxbury

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