Roxbury Homes for Sale

Welcome to Roxbury, Connecticut—a hidden gem nestled in the scenic Litchfield County. Known for its charming rural landscape and rich history, Roxbury offers a unique blend of tranquility and vibrancy that appeals to nature lovers and city dwellers alike. With its rolling hills, lush forests, and picturesque countryside, this quaint town provides the perfect backdrop for a peaceful lifestyle while still being conveniently located near larger urban centers.

Roxbury is characterized by its tight-knit community, where local events and gatherings foster a warm, welcoming atmosphere. The town is home to several parks and recreational areas, offering ample opportunities for hiking, biking, and enjoying the great outdoors. With its historic homes and beautiful landscapes, Roxbury is a haven for those seeking a slower pace of life without sacrificing modern conveniences.

For those considering a move to this idyllic locale, the real estate market in Roxbury is thriving. Homes for sale in this area range from charming historic properties to modern builds, catering to a variety of tastes and budgets. Whether you're looking for a cozy cottage surrounded by nature or a spacious family home with plenty of room to grow, Roxbury has something for everyone.

Explore the diverse selection of homes available and discover the perfect sanctuary that meets your needs. With its stunning scenery, strong community spirit, and a wealth of outdoor activities, Roxbury is not just a place to live—it's a place to thrive. Come and experience all that this enchanting town has to offer!

Newest Roxbury Homes for Sale

$1,235,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ 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

$1,300,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$3,600,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24183686 MLS

Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite pool, pool house, 4-stall horse barn, tennis court. Riding ring, fenced pastures, wooded trails for hiking etc. Perennial gardens. Property abuts conservation land. Complete privacy. Rare opportunity. Property has only been on the market twice before in past 100 years.

268 South St, Roxbury

$3,200,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24186522 MLS

Exceptional equestrian estate featuring a fully equipped horse facility and charming Cape-style home. Ideal for equestrians, trainers, or boarding professionals, the property offers 16 rubber-matted stalls, a large well-lit indoor arena, and a second-floor viewing lounge with kitchen amenities-perfect for lessons, clinics, and entertaining. The barn includes a wash stall, feed room, hay storage, boarder tack lockers, laundry area, and full bath. Safety is enhanced by a commercial sprinkler system. Owned pole-mounted solar panels are installed but are not currently operational. Outside, expansive grass paddocks and a large sand/stone dust outdoor arena provide ample space for training and turnout. Bordering Land Trust property with a river and miles of trails, you can horseback ride or hike directly from your back door. "The Shepaug is one of those rivers that looks like it was painted by someone who had too much talent and not enough canvas." written by Charles Hayes. The Cape-style home features 3 bedrooms and 2 full baths, blending classic New England character with modern comfort. A 2-car attached garage is complemented by a detached 4-car garage, plus an additional detached 3-car garage with a second-floor apartment-ideal for guests, staff, rental income, or a home office.

4 Judge Rd, Roxbury

$850,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24180161 MLS

Step back in time and own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic property and make it your own. A welcoming foyer greets you upon entry and leads to a spacious formal living room featuring a classic fireplace. The sunroom is complete with a wood-burning stove. Upstairs, you'll find three bedrooms, including one pass-through bedroom that offers flexibility for a nursery, office, sitting room, or guest space. A full bath serves the second floor. The home's unique feature may be the finished walk-up attic, complete with a working sink and endless possibilities as an artist's studio, creative workspace, hobby room, or private retreat. Recent improvements include a professionally installed Connecticut Basement Systems waterproofing system, featuring a new sump pump and dehumidifiers to help maintain a clean, dry basement year-round. Filled with memories, history, and timeless architectural details, the Philo N. Hodge House is ready for its next chapter. Buyers are encouraged to conduct their own due diligence with the Town of Roxbury regarding any regulations, permits, approvals, historic preservation considerations, or future improvements to the property.

47 South St, Roxbury

$618,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24182244 MLS

Chic Country Cabin in Bucolic Litchfield County. Escape to your own peaceful retreat offering the perfect blend of comfort, character, and privacy on nearly 5 acres of wooded wonderland. This home has lots of character and a flexible layout with 2 bedrooms, 2 full bathrooms plus an upper level guest room/office/rec room. The living areas are ideal for relaxing or entertaining, and the kitchen has plenty of prep and storage space. Step outside onto the expansive wrap-around deck - the perfect spot for morning coffee, al fresco dining, or simply unwinding and unplugging while enjoying the sights and sounds of your private pond and surrounding woods. Nature lovers will appreciate the serene setting that offers privacy and tranquility. Hikers and bikers will love nearby trails and land trust. Roxbury, CT, has long been sought-after as a convenient country getaway providing small-town Connecticut living and yet less than 2 hours from NYC. Very convenient to shopping in nearby Woodbury and Southbury. You've got to see this one!

188 Bacon Rd, Roxbury

$725,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24178189 MLS

Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. At its heart is a spacious eat-in kitchen, flanked by a formal dining room and library on one side, and a sunlit living room wrapped in windows on the other. The 658 square-foot guest house overlooks the spring-fed pond and includes a generous living room, two bedrooms, and a full bath-serviced by its own septic. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and gently rolling lawn. This charming home blends history, potential, and natural beauty in one of Litchfield County's most coveted locations., Additional acreage available- separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. Total square footage is combined main house and guest house.

50 Southbury Rd, Roxbury

$3,995,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24177581 MLS

A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms and five full bathrooms and one powder room. A grand living room, complete with a two-story fireplace and windows on three sides, opens to two decks overlooking the rear yard. The spacious formal dining room, equipped with a gas fireplace and soft indirect lighting, is ideal for hosting formal gatherings. The chef's-eat-in kitchen, generously furnished with ample cabinetry, marble countertops, connects to a large deck and a granite patio, facilitating seamless outdoor dining. The primary level's main suite features French doors to the gardens, a luxurious bath, two walk-in closets, and a private sitting room. Three additional ensuite bedrooms complete the main level. The lower level offers a media room, a game room, a bunk room with built-in beds, a spa bath, and a laundry facility. A separate guest cottage provides a cozy retreat with two bedrooms, two bathrooms, a vaulted great room, a kitchenette, a fireplace, and a wrap-around deck. A must see!

47 Squire 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

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