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Roxbury CT Real Estate

Incorporated in 1796, Roxbury is located in the beautiful northwest corner known as the Litchfield Hills. Spread over 26-square miles, our rural town of 2,320 offers historic sites and architecture as well as rural ambiance. In the western part of town, the Shepaug River flows in a southerly direction, cutting a narrow valley through hills on either side. The Town Green holds the town’s smallest cemetery and granite memorial to Revolutionary War hero and Roxbury native, Seth Warner. Warner was Captain of the local regiment of the Green Mountain Boys, formed to resist New York authority over Vermont. He was a hero often overshadowed by his more flamboyant Roxbury-born cousins and Green Mountain comrades-in-arms, Ethan Allen and Remember Baker.

Roxbury is proud of its farming and mining heritage, its architecture and barns, its Historic District and its friendly, community-spirited residents.

Dave Jones, your Roxbury CT Real Estate Broker.

CT MAgazine 5 Star Award winner 7 consecutive years!

 

roxbury award winning realtor

Roxbury CT Real Estate

$1,235,000
4 Beds ⋅ 3 Baths ⋅ 24192986 MLS
Completely reimagined from top to bottom, 22 E. Woods Rd. is a home where elevated design meets everyday comfort. From the moment you step inside, gleaming hardwood floors, abundant natural light, and an inviting open floor plan create a warm and welcoming atmosphere that feels equally suited to quiet mornings and lively gatherings. At the heart of the home is a stunning custom kitchen featuring a beautiful blend of crisp white and natural-tone cabinetry, granite countertops, and high-end stainless steel appliances. The adjoining living spaces flow effortlessly together, anchored by a charming fireplace that adds warmth and character. The primary suite offers a private retreat, with a spa-like bathroom featuring a luxurious soaking tub and oversized tiled shower, a walk-in closet, and a separate flex space ideal for a nursery, dressing room, or home office. Three additional generously sized bedrooms share a brand-new, beautifully appointed full bathroom. Don't miss the bonuses room with separate staircase over the garage perfect for a home office, den or other uses. Outside, front and rear patios extend the living space and offer inviting spots to enjoy a morning coffee, gather with friends, or simply relax. Freshly painted inside and out, with a new roof and driveway, this exceptional home offers the rare opportunity to enjoy the a near completely new property while still feeling unmistakably like home.

22 E Woods Rd, Roxbury
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 24193455 MLS
A custom-designed Judds Bridge Colonial in a coveted location, privately set amid mature trees and established plantings. A dramatic double-height marble foyer introduces the home's beautiful architectural millwork and rich cherry floors on the main level. The well-proportioned interiors include formal living and dining rooms, office or bonus room, an open and eat-in kitchen with solid cherry cabinetry, double oven, cook top, peninsula with seating, pantry, powder and laundry room, and a spacious den with vaulted ceilings, antique beams and centered around a soaring Rumford fireplace. The primary suite features a tray ceiling, en-suite bath with double sink, generous walk-in closet, while three additional bedrooms share a full bath. Out the French doors onto Ipe deck provides a refined setting for outdoor living and your private back yard. Additional highlights include a three-car garage, an unfinished bonus room over the garage that offers excellent expansion potential, new UV paned deck doors, updated mechanicals, architectural roof shingles, and a portable generator. Quintessential New England living at it's best!

77 Judds Bridge Rd, Roxbury
$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 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
$1,300,000
3 Beds ⋅ 3 Baths ⋅ 24192683 MLS
Completely remodeled 3 bedroom, 2.5 bath open concept home, with two fireplaces (one with wood burning insert), kitchen with stainless appliances, granite counters and large island. Property is private - boarders 18 acre land trust and farm land. Gunite pool (propane heater) with pavilion and fire pit for entertaining. Hot tub off main bedroom patio. Property features stone walls, steps and patios. Generac whole home generator. Detached oversized garage with game room (potential in-law set up). Great home for entertaining.

85 Good Hill Rd, Roxbury
$1,795,000
5 Beds ⋅ 6 Baths ⋅ 24189301 MLS
Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand circular driveway introduces the residence, where sweeping lawns and striking architecture create a powerful sense of arrival, privacy, and seclusion. Inside, light-filled interiors showcase soaring ceilings and oversized windows that capture serene vistas from nearly every room, blending contemporary sophistication with warmth and comfort. The remodeled kitchen serves as the heart of the home, seamlessly combining modern design with functional luxury as it flows into the main living areas. With five generously proportioned bedrooms and six bathrooms, the thoughtfully scaled floor plan accommodates both grand entertaining and intimate everyday living. The lower level features a versatile in-law suite complete with a full kitchen, private bedroom, bathroom, living room, separate entrance, and direct access to the grounds, along with an additional great room or family room that opens to the expansive lawn, offering a seamless indoor-outdoor connection ideal for guests or multigenerational living.

233 Southbury Rd, Roxbury
$499,000
24189150 MLS
ENGINEERING and DRIVEWAY APPROVED! THERE ARE LOTS AND THEN THERE ARE MAGICAL, SPECIAL, UNPARALLELED LOTS, STEEPED IN HISTORY WHERE YOU CAN ACTUALLY FEEL AND HEAR THE TERRAIN SINGING TO YOU. THE WOODS ROXBURY IS SUCH A PLACE AS EVIDENCED BY OUR RECENT SALES. THIS IS THE LAST AVAILABLE LOT FROM PHASE II, (LOT #1) AND IT MUST BE SEEN AND HEARD TO UNDERSTAND HOW YOUR FUTURE HEIRLOOM HOME WILL BE CHERISHED. This 8.64 acre lot features un-touched historic stone walls, a beautiful stream flowing, gently sloping tree-covered hills and an abundance of ferns, pine trees, oaks and maples as your canvas. The home site is absolutely flat and perfect! This masterpiece lot is ideal to build your dream home and to connect with what is important in life. Whether a weekender or full-time resident, the Woods will offer you ultimate privacy with endless possibilities for a simpler place and way of life. Our wonderful architectural team is available to design your one of a kind home or you can bring your own. Shown by Owner/Agent.

200 North St, Roxbury
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