Painter Hill Real Estate

Welcome to Painter Hill, a hidden gem nestled in the picturesque town of Roxbury, Connecticut. This charming neighborhood, located in Litchfield County, is a perfect blend of serene countryside living and vibrant community spirit. With its rolling hills, lush landscapes, and stunning views, Painter Hill offers a tranquil retreat from the hustle and bustle of city life.

One of the standout features of Painter Hill is its rich history and strong sense of community. The area is dotted with beautifully preserved colonial homes and quaint farmhouses, each telling a story of the past. Residents take pride in their neighborhood, fostering a welcoming atmosphere where neighbors become friends. The local community often comes together for seasonal events, farmers' markets, and festive gatherings, creating a close-knit environment that makes everyone feel at home.

For nature enthusiasts, Painter Hill is a paradise. The neighborhood is surrounded by scenic hiking trails, serene lakes, and expansive parks, perfect for outdoor activities like biking, fishing, and picnicking. The nearby Roxbury Land Trust ensures that the natural beauty of the area is preserved, providing ample opportunities for exploration and adventure.

Families will appreciate the excellent educational opportunities available in Roxbury, with top-rated schools that prioritize academic excellence and personal growth. Additionally, the neighborhood's convenient access to nearby towns and cities means that residents can enjoy both the tranquility of rural life and the amenities of urban living.

Whether you’re seeking a peaceful retreat or a vibrant community, Painter Hill offers the best of both worlds. Come discover the charm and beauty of this delightful neighborhood today!

Newest Listings in Painter Hill

$4,495,000

4 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$2,000,000

ACTIVE Status ⋅ 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

$2,895,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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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