Painter Hill Homes for Sale

Welcome to Painter Hill, a hidden gem nestled in the picturesque town of Roxbury, Connecticut. This charming neighborhood is characterized by its rolling hills, lush greenery, and a serene atmosphere that invites you to unwind and enjoy the beauty of nature. With its rich history and close-knit community, Painter Hill offers a unique blend of rural charm and modern convenience, making it an ideal place for families, retirees, and everyone in between.

As you stroll through the tree-lined streets, you’ll discover a variety of beautiful homes that reflect the area’s distinctive character. From cozy cottages to sprawling estates, the homes for sale in Painter Hill cater to diverse tastes and lifestyles. Each property boasts unique architectural features, spacious yards, and stunning views of the surrounding landscape. Whether you’re seeking a peaceful retreat or a place to raise a family, you’ll find the perfect home that suits your needs.

Living in Painter Hill means embracing a lifestyle that values community and connection. Residents enjoy access to local parks, hiking trails, and recreational activities, all while being just a short drive away from Roxbury’s charming shops, restaurants, and cultural attractions. The nearby Litchfield County offers even more opportunities for exploration, with its scenic vistas and vibrant arts scene.

If you’re ready to find your dream home in a neighborhood that feels like a warm embrace, Painter Hill is waiting for you. Explore the available homes for sale today and discover the enchanting lifestyle that awaits you in this idyllic corner of Connecticut!

Newest Painter Hill Homes for Sale

$4,495,000

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. 3rd floor loft. Recreation Room/Guest Apartment over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, additional bedroom, 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

$950,000

3 Beds ⋅ 2 Baths ⋅ 24174231 MLS

INCREDIBLE OPPORTUNITY TO OWN IN THE PAINTER HILL RD AREA OF ROXBURY! This 1,600 sq ft, 3-bedroom, 2-bathroom Ranch home with a 2-car garage sits on a sun-filled, gently sloping lot with tremendous potential for the new Homeowner. The home will be a Complete REMODEL with Separate Driveway. . The septic was last pumped September 2025, and annual taxes are just $3,851. Renovation by Design Builders & Remodeling Inc. AS IS option under MLS # 24166843 for details. Either way, you'll be planting roots in Roxbury, one of the most sought-after towns in the Litchfield Hills - known for its low taxes, natural beauty, and year-round outdoor activities.

137 Davenport Rd, Roxbury

$1,049,000

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

$1,895,000

4 Beds ⋅ 4 Baths ⋅ 24170163 MLS

Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble tech finish was installed with fencing in the rear yard for the pool and pets. The house was originally built by a Master Craftsman with the finest materials.The gourmet kitchen is where everyone lives. There is a center island and field stone fireplace. Thermador appliances include a 6 burner cook top as well as wall oven, built in microwave, a warming drawer, dishwasher and refrigerator. The open floor plan allows you to set up the living room/dining room in a variety of ways. There is a lovely sunroom with a vaulted ceiling off the kitchen. There is a mudroom coming in from the garage with a half bath. The ceilings are 9' on the first floor. The upper level includes a lovely Primary Suite with walk in closets, a luxurious primary bath with 2 sinks, a walk in shower and a soaking tub. There are 3 additional bedrooms on the upper level with one en-suite and the other two sharing a hall bath. The house sits up high with mountain views. The land is gently sloping with a level area with plenty of room to play. Only 90 minutes to NYC!

18 Ranney Hill Rd, Roxbury

$2,895,000

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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