Roxbury Homes with Colonial Style

Welcome to Roxbury, Connecticut – a charming town nestled in the heart of Litchfield County, known for its picturesque landscapes and rich history. With its rolling hills, lush greenery, and serene atmosphere, Roxbury offers a perfect escape from the hustle and bustle of city life. This quaint community is characterized by its tight-knit neighborhoods, friendly residents, and a strong sense of pride in local heritage.

Roxbury is not only a haven for nature lovers but also a treasure trove of architectural beauty, particularly when it comes to its stunning Colonial-style homes. These timeless residences reflect the town’s historical roots and are a testament to the craftsmanship of bygone eras. With their symmetrical facades, gabled roofs, and classic brick or wood siding, Colonial homes in Roxbury exude an air of elegance and charm. Many of these properties are set on spacious lots, allowing for expansive gardens and outdoor living spaces that perfectly complement the natural beauty of the surroundings.

Living in Roxbury means embracing a lifestyle that values community, history, and the great outdoors. Residents enjoy access to numerous hiking trails, parks, and recreational activities, making it an ideal spot for families and nature enthusiasts alike. The town also hosts various cultural events and farmers’ markets, fostering a sense of community and connection among its residents.

Whether you’re searching for your dream home or seeking a peaceful retreat, Roxbury’s Colonial-style properties offer a unique blend of history, charm, and modern amenities. Discover the beauty of Roxbury and let its enchanting homes welcome you home.

Newest Roxbury Homes with Colonial Style

$998,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204225 MLS

Tucked away on a highly sought-after country road, this charming Colonial has been lovingly maintained by its original owners and offers privacy, lovely grounds, and exceptionally low taxes. Distinctive character begins with its graceful rounded-front porch and continues throughout this exceptionally well-built home, where timeless craftsmanship meets enduring charm. A welcoming foyer features a distinctive staircase to the upper level and opens to the living and dining rooms on the left, while a cozy den flows into the bright eat-in kitchen on the right. The laundry and half bath are conveniently located just off the kitchen. Beautiful hardwood floors, two fireplaces, and French doors leading to private patios create inviting spaces for everyday living and entertaining. Upstairs, the spacious primary suite offers walk-in closets and a well-appointed bath with Jacuzzi and large separate shower. Two additional bedrooms feature generous closets, complemented by a large linen closet. This well loved home is on a beautiful lot, at an approx. 1000 ft elevation, has mature landscaped grounds, private patios and a cute garden shed creating a peaceful country retreat. There is an approx 1,100 sq ft basement with tall ceilings offering a great expansion opportunity, or excellent for storage. Roxbury is a quintessential New England community with very low taxes and home to well-regarded schools. It is also known for its natural beauty, historic character, and strong sense of community.

16 Jonathan Dr, Roxbury

$1,195,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192986 MLS

*Completely reimagined from top to bottom, 22 E. Woods Rd. offers the rare combination of virtually new, low-maintenance living, nearly 7 acres of beautiful privacy and exceptional value. WITH JUST $7,395 in annual property taxes, the monthly cost to own and operate this home can be a fraction of what you'll find in many surrounding towns. Inside, gleaming hardwood floors, abundant natural light and an inviting open floor plan create a warm, comfortable atmosphere. The stunning custom kitchen features crisp white and natural-tone cabinetry, granite countertops and high-end stainless-steel appliances, flowing seamlessly into the living spaces anchored by a charming fireplace. The spacious primary suite offers a spa-like bath with soaking tub and oversized tiled shower, walk-in closet and separate flex space perfect for an office, nursery or dressing room. Three additional bedrooms share a brand-new full bath, while a bonus room over the garage-with its own staircase-offers even more flexibility. Outside, front and rear patios provide wonderful spaces for relaxing or entertaining while nearly 7 acres offer privacy and room to enjoy the outdoors. Freshly painted inside and out, with a new roof and driveway, this home is truly move-in ready and designed for worry-free living. Nearly a complete renovation, incredibly private, low taxes and a remarkably low cost of ownership-this is a rare opportunity to enjoy a nearly new home with the space and privacy you've been looking for!

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

$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

$850,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24180161 MLS

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

$725,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE 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

$2,750,000

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

$995,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24164547 MLS

Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and convenience. An active solar energy system helps offset utility costs and enhances long-term efficiency. Set on 3+ private acres, the property enjoys an exceptional natural backdrop with extensive undeveloped acreage beyond the rear property line, creating privacy and peaceful woodland views. Mature landscaping, a spacious deck, and a serene setting make the outdoor spaces ideal for entertaining or quiet enjoyment. The flexible floor plan includes a private in-law, studio, or home office space, ideal for today's evolving lifestyle needs. Beyond the 3,340 sq. ft. of above-grade living space, the home offers an expansive full lower level providing approximately 1,700 sq. ft. of dry bonus space ideal for storage, recreation, workshop, fitness, or future customization. An enormous walkable attic spanning nearly the entire 2nd floor footprint provides exceptional add'l storage rarely found in homes of this era.

24 Hickory Ln, Roxbury

$1,469,000

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

$969,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24163273 MLS

MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round Spa Pool -- all on the best rural Roxbury scenic dirt road with walking area along the Shepaug River and nearby historic farmhouses and land preserve. All minutes to The Mayflower. Pristine renovated private country home with 3 bedrooms/2.5 baths and an ample home office. Open floorplan Living/Eat-in Kitchen/Family Room with wood burning fireplace and sliders to a year-round, heated pool and patio. Dine or relax on the granite terrace or covered front porch surrounded by mature woods and amazing rock outcroppings. Attached 2-car garage. Mint Condition! Move Right In!

18 Tunnel Rd, Roxbury

$1,495,000

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

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24159885 MLS

Own a Piece of Roxbury History! 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 for hiking, 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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