N/A Homes with Booth Free Elementary school

Welcome to Roxbury, Connecticut – a hidden gem nestled within Litchfield County, where charming landscapes and a close-knit community come together to create an idyllic living environment. Known for its picturesque rolling hills and serene countryside, Roxbury offers a tranquil escape from the hustle and bustle of city life, making it an ideal place for families and individuals alike.

One of the standout features of this charming town is its strong commitment to education, highlighted by the presence of Booth Free Elementary School. This highly regarded institution is a cornerstone of the community, providing children with a nurturing and stimulating environment to grow and learn. Parents can take comfort in knowing that their children are receiving a quality education right in their own backyard, fostering a sense of community and connection among families.

The homes in Roxbury reflect the town's character, with a delightful mix of historic architecture and modern designs. Whether you’re drawn to a cozy cottage or a spacious family home, the real estate options here cater to a variety of tastes and lifestyles. The surrounding nature provides ample opportunities for outdoor activities, with hiking trails, parks, and scenic spots perfect for family outings or quiet retreats.

In Roxbury, you’re not just buying a home; you’re investing in a lifestyle rich with community spirit, educational excellence, and natural beauty. Discover the charm of Roxbury and find your perfect home today!

Newest N/A Homes with Booth Free Elementary school

$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

$1,300,000

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

$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

3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24175557 MLS

This handsome 1820's Colonial, set behind large shade trees on 1.33 acres just off the Green, is an easy walk to the Library, Booth School, Apple Lane Park, Churches, Tennis courts, and a morning cuppa at the Roxbury Market. Major renovation in 2018 included New HVAC, New wiring, Rebuilt Porch and more. New Well installed dedicated to this property replaced shared source. Interior makeover included fine Kitchen with gas range and quartz counters, formal Dining room or Library, Powder Room, and front-to-back Living Room leading to full-width covered porch overlooking the lawn, wonderful for entertaining. The Main floor shines with wide-board oak floors, thermal windows and traditional trim. Greet the morning sun in the second floor primary Bedroom with ensuite bath and walk-in closet. Two other bedrooms and hall bath also share this floor. Stairs lead up to the third floor and two more finished rooms. Level lawn behind the house extends back to a large barn with water, electric and a poured concrete floor for garage or many other creative uses. There's so much here in this inviting antique Roxbury home that lives like new!

20 Wellers Bridge Rd, Roxbury

$1,795,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24171982 MLS

Sprawling 4-bedroom colonial as part of a peaceful and private 17-acre estate in desirable Roxbury, CT. Sighted well on open rolling lawns with sweeping sunrise/sunset views, this property offers country living with exceptional versatility. The sun-filled eat-in kitchen features has sliders that open to a jumbo 58' deck with awning and open views. Generous main-level spaces include a dramatic family room with vaulted ceilings, wood-paneled dining room, living room with fireplace, large office/den/library, laundry room, and powder room. Upstairs are four bedrooms and two baths, including a spacious primary suite with walk-in closets and dressing area. The lower level has lots to offer with another half bath, gym/workout area, lots of storage and access to the 2-car garage. Outside, the spotlight is on the Pebbletec saltwater pool that is beautiful and low maintenance. The property has an abundance of open space and open sky in all directions. Multi-stall barn with hay loft and a 930 sq ft apartment, offering flexibility for equestrian pursuits, collector storage, creative studios, wellness uses, and income potential. Plus, detached 3-bay garage and a whole-property generator. Truly perfect for those seeking a country retreat or a gentleman's farm, and only 90 minutes from NYC - near Woodbury and part of the Washington-Roxbury corridor. Welcome home to Litchfield County!

25 Highmeadow Ln, Roxbury

$1,000,000

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24157035 MLS

Discover modern serenity in this private contemporary retreat nestled on 3.44 private acres. The ascending driveway assures a sense of quiet and seclusion, leading you to a home bathed in natural light from a soaring two-story wall of south-facing windows, this home perfectly blends architectural drama with a peaceful woodland backdrop. The exterior features an expansive, brand new composite deck with its sleek cable railing system--perfect for al fresco dining or quiet mornings. Inside, the light filled, open-concept main level is anchored by 5 1/4" hardwood oak flooring and a dramatic granite gas burning fireplace. A full wall of custom built in's create style and ample storage. The kitchen is designed for functionality with its central island, quartz countertops and new Fulgar Milano induction range and a new LG refrigerator. Retreat to the main-level primary on-suite, which offers its own private deck access via French patio doors. Upstairs, a glass railed loft provides additional flexible space. The fully tiled walk out lower level includes a full bath offering excellent potential for an in law apartment, guest suite or private home office with a 2nd laundry hook up area in the garage. Meticulously maintained and newly painted throughout, this sanctuary is equipped with radiant heat, central air, a main level laundry and a newer water softening system.

28 Garnet Rd, Roxbury

$679,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24162576 MLS

Step back in time with this historic 1800s Colonial that retains its original character and charm while offering modern amenities, including an updated kitchen and bathrooms. The home features four bedrooms upstairs with wood floors, including a primary bedroom with an attached room currently used as an office. The main level with a den, living room with fireplace, dining room, and a mahogany-floor kitchen. Plus a mudroom/laundry room leading to the back patio. A large barn provides ample storage, and the property includes a 1,250-gallon 4-bedroom septic tank installed in 2008, a fully fenced backyard, and a 24-foot-wide new asphalt driveway. Recent upgrades include a new barn roof and framing, new 200-amp electrical panel and some wiring in the main house, insulated exterior walls, remodeled shower and fireplace, new wainscoting in the upstairs hallway, new glass backsplash in the kitchen, and restored original wood floors upstairs. Enjoy relaxing on the front porch or rear stone patio and take advantage of nearby hiking trails, parks, and open space, with Southbury, Bridgewater, and Washington town centers just a short drive away. Confirmed appointment required for showings.

216 Baker Rd, Roxbury

$1,549,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24163570 MLS

Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room, spacious dining room and chef's kitchen with striking polished hardwood center island. Upstairs, Primary En Suite Bedroom with lovely clawfoot tub, double sinks, large separate shower and spacious dressing room. Two more bedrooms share a charming hall bath. Finished lower level currently outfitted as a family room with French doors to a serene patio leading out to the pool, another en suite bedroom and two more finished flexible spaces. (Makes the total finished sq feet: 3676!)The perfect peaceful location, minutes from the centers of Roxbury and Washington. Must see!

33 Sentry Hill Rd, Roxbury

$1,550,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24162311 MLS

Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray ceilings, and abundant natural light throughout. The gourmet kitchen features custom cherry cabinetry, granite countertops, stainless steel appliances, and a butler's pantry, opening to a warm hearth room with a fieldstone fireplace. A sunken family room with a brick fireplace and French doors leads to a stone patio, creating an ideal flow for indoor-outdoor living. The upper level offers a spacious primary suite, three additional bedrooms, three full baths, and a versatile rooms suitable for a home office, lounge, or playroom. The walk-out lower level with 9-foot ceilings provides approximately 1,950square feet of additional living space, including a recreation area, full bar, exercise room, bedroom, full bath, and flexible space for entertaining or extended living. The grounds offer a peaceful retreat with woodland trails, a stream, fire pit, outbuildings, and a two-story pool house. Additional features include a chicken coop and utility structure, enhancing the property's country lifestyle appeal. Conveniently located near local amenities while offering privacy and tranquility.

380 Southbury Rd, Roxbury

$985,000

ACTIVE Status ⋅ 24160249 MLS

Beautiful East Facing Views from this Piece of Roxbury History! Land ready to build with one of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as historic landmark, adds further character and value. The property abuts Land Trust land, ensuring privacy and natural beauty. Infrastructure is in place with a completed A-2 survey, installed driveway, and approved septic plans (3-bedroom for the antique home and 8-bedroom for a main residence). Electrical conduit is also installed to the proposed homesite. This land has subdivision potential and is ready for you to create a legacy of your own. **Note: Home is uninhabitable at this time. A full rebuild and renovation is required.

179 South St, Roxbury

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