Roxbury CT Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
1,782
Status:
NEW LISTING
MLS#:
24167690
Type:
Single Family
Subdivision:
Painter Hill
Lot size:
3 Acres
Year built:
1990
Courtesy: Klemm Real Estate Inc 860-868-7313
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ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,031
Status:
NEW LISTING
MLS#:
24173105
Type:
Single Family
Subdivision:
Moosehorn
Lot size:
3.21 Acres
Year built:
1955
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

Juniper Hill offers masterfully updated one level living in Roxbury, Connecticut. Dubbed a "Little Gem on the Hill" in Country Home, this unassuming ranch has been elevated with chic, yet family friendly styling. Modern comforts combine with country character in a home situated on compelling terrain. Kelly + Co Design awarded Best Interior Designer Small Home/Cottage, 2020, CT Cottage and Gardens for their work on this home. Primary bedroom en suite with stall shower and claw foot tub. Two guest bedrooms share full bath with wall to wall shower offering the choice of a traditional or rain shower head. Oversized living room windows face west and are opposite a grand wood burning fireplace. A bay window looking out to the pool lends charm to the dining area. Magnificent sunroom wrapped in windows that bring the outdoors in. Top of the range projection home theater. Chef's kitchen with fireplace has windows lined above the sink counter looking out to the large, level yard and play areas. Cooktop set in sizable island that has additional cabinet storage and breakfast bar. Whole house generator, Central air, brand new gas furnace heat and on-demand hot water. Two-bay, detached garage. Buried utility lines.

Open House:

Saturday, 5/9 12:00-2:00PM

More Open House Info >

Beds:
4
Baths:
4.00
Sq.Ft.:
4,310
Status:
NEW LISTING
MLS#:
24171982
Type:
Single Family
Subdivision:
N/A
Lot size:
17.31 Acres
Year built:
1986
Courtesy: Compass Connecticut, LLC 203-293-9715
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ADDITIONAL INFORMATION

Fantastic opportunity to own an estate in bucolic southern Litchfield County, complete with saltwater gunite pool, open rolling lawns, sunrise/sunset views, and equestrian facilities. Spanning over 17 private acres, this property is anchored by a handsome 4-bedroom colonial home loaded with charm and lots of room to entertain. The eat-in kitchen is the heart of the home with a DCS stove, Sub-Zero refrigerator and sliders that open onto the 58' deck with open views of the property and beyond. Oversized family room with vaulted, beamed ceiling and French doors leading to the deck with seating areas and an awning. Large wood-paneled dining room, living room with fireplace and custom built-ins, large home office or library, laundry and powder room all on the main floor. Upstairs there are four bedrooms, including a wonderful primary suite. Jumbo partially-finished lower level with office space, gym & multi-purpose room. Lots of open spaces, fencing, a pond, and of course the newly constructed in-ground pool. Whole house generator; 14-stall barn with wash stall, tack and feed rooms, large hay loft, and 930 sq ft caretaker's apartment. Additional outbuildings, including a machinery barn/garage, chicken coop, paddocks and numerous trails throughout this wonderful property. Roxbury is a charming town about 90 minutes to NYC, very convenient to shopping in Woodbury & Southbury, and just down the road from Washington Depot. Come home to Litchfield County.

Beds:
3
Baths:
4.00
Sq.Ft.:
3,696
Status:
Active
MLS#:
24157035
Type:
Single Family
Subdivision:
N/A
Lot size:
3.44 Acres
Year built:
1990
Courtesy: Compass Connecticut, LLC 203-245-1593
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ADDITIONAL INFORMATION

Discover modern serenity in this secluded contemporary retreat nestled on 3.44 private acres. 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.

Open House:

Saturday, 5/9 12:30-2:30PM

More Open House Info >

Beds:
4
Baths:
4.00
Sq.Ft.:
2,420
Status:
Active
MLS#:
24163465
Type:
Single Family
Subdivision:
N/A
Lot size:
8.56 Acres
Year built:
1966
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

Situated in Roxbury near the Washington border, this quintessential 1960's four bedroom Cape Cod with heated pool, serves as a private sanctuary, harmonizing classic New England architecture with modern refinements. The exterior is characterized by a handsome cedar wood shingle roof and landscape defined by mature trees, rock outcroppings, and vibrant perennial gardens. Outdoor living is central to the property's allure, featuring an inground pool, sprawling 19 x 22 raised deck and screened porch providing a serene, airy environment for three-season relaxation - a natural extension of the interior living space. The heart of the home is the kitchen, a chef's delight featuring high-end Sub-Zero refrigeration and finishes that overlook the lush grounds. The interior is defined by freshly painted walls and gleaming hardwood floors that lead to a coveted primary suite conveniently located on the main level. With a total of two full and two half baths, the home is thoughtfully configured for both privacy and guest convenience. Additional versatility is found in the finished lower level, which currently hosts a private gym and a spacious recreation room complete with its own half bath. This level provides the flexible space necessary for contemporary living, whether used for fitness, media, or a home office.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,556
Status:
Active
MLS#:
24169438
Type:
Single Family
Subdivision:
Roxbury Falls
Lot size:
4.33 Acres
Year built:
1989
Courtesy: Redfin Corporation 203-349-8711
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ADDITIONAL INFORMATION

Beautiful 4 bedroom, 2.5-bath Colonial set on a picturesque, park-like property in desirable southern Roxbury. A dramatic two-story foyer welcomes you into a thoughtfully designed layout featuring a formal dining room, a spacious living room with custom built-in bookshelves, and an impressive family room highlighted by a floor-to-ceiling fireplace and custom built-ins. The kitchen is well-appointed with granite countertops, a center island, and French doors that open seamlessly to an expansive deck and terrace-ideal for indoor-outdoor living and entertaining. Overlooking the beautifully landscaped grounds, the outdoor space features an in-ground pool, mature gardens, and lush plantings that create a private retreat-like setting. Additional highlights include ~300k in upgrades, beautiful hardwood floors throughout, a whole-house Generac generator, two-car garage underneath, an expanded driveway (30k), and a charming stone walkway that enhance the property's natural beauty. A rare opportunity to enjoy tranquility, space, and convenience, just 90 minutes from NYC.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,620
Status:
Active
MLS#:
24171072
Type:
Single Family
Subdivision:
Tophet
Lot size:
0.98 Acres
Year built:
2006
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

This cross gabled farmhouse was built in 2006 by its artisan craftsman owner, expanding upon the original foundation of a dwelling previously occupied by the caretaker of Arthur Miller's residence. The home was designed to leverage distant views east that stretch across thousands of acres of forested land to ridgelines in the towns of Woodbury and Bethlehem. The owner harvested and milled trees found locally to construct the flooring, stairs, cabinetry, interior doors and most of the finish moldings, creating exceptional detail and character rarely found at this price point. No less impressive is the handsome and considerable stonemasonry he crafted, surrounding the house and connecting its points of entry to exterior living spaces. All three bedrooms have windows facing the long views with both the primary suite and open kitchen/dining space featuring french doors to the outdoor stone terrace extending toward the panoramic scenery. Magnificent living room with granite framed wood burning fireplace and a flat screen TV cabinet above the mantle that is flanked by built-in bookshelves. Large main level den/office and dedicated pantry with sink, wine fridge and game freezer. Second floor office could also be used for overflow guests. Savor the secret lifestyle sauce located in Roxbury's coveted southeast hill country that has drawn luminaries past and present, including Miller, Monroe, Widmark, Matthau, Calder, McCourt, Hoffman, Rayburn, Reed, Bushnell, Leoni & Ecklund.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,570
Status:
Active
MLS#:
24167130
Type:
Single Family
Subdivision:
Painter Hill
Lot size:
4.68 Acres
Year built:
2007
Courtesy: W. Raveis Lifestyles Realty 860-868-0511
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,340
Status:
Active
MLS#:
24164547
Type:
Single Family
Subdivision:
N/A
Lot size:
3.01 Acres
Year built:
1987
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

Tucked away in one of Roxbury's most desirable neighborhoods, this 4-bedroom, 2.5-bath Colonial sits at the end of a quiet dead-end road, offering exceptional privacy and a peaceful setting, with the Natalie White Preserve just down the road. This beautifully updated Post & Beam home blends timeless craftsmanship with modern amenities, featuring warm architectural details, exposed white oak beams, and a dramatic living room with soaring 27-foot ceilings, along with thoughtfully designed living spaces. The flexible layout includes a private in-law or studio space, ideal for guests, extended family, or a home office. Set on a serene, wooded 3-acre lot with mature landscaping, the property provides a tranquil retreat perfect for relaxing or entertaining. Despite its secluded feel, it's a short 15 minutes drive from fine-dining, shopping, and easy access to I-84, and ideally located just over 90 minutes to NYC and approximately 2 hours 20 minutes to Boston, offering both convenience and comfort in a truly special location.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,008
Status:
Active
MLS#:
24162576
Type:
Single Family
Subdivision:
N/A
Lot size:
0.85 Acres
Year built:
1827
Courtesy: RE/MAX Right Choice 203-426-4004
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,716
Status:
Active
MLS#:
24163570
Type:
Single Family
Subdivision:
N/A
Lot size:
3.01 Acres
Year built:
2002
Courtesy: Klemm Real Estate Inc 860-868-7313
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ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,080
Status:
Active
MLS#:
24163273
Type:
Single Family
Subdivision:
Judd'S Bridge
Lot size:
3.1 Acres
Year built:
2000
Courtesy: Klemm Real Estate Inc 860-868-7313
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ADDITIONAL INFORMATION

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!

Beds:
4
Baths:
5.00
Sq.Ft.:
6,444
Status:
Active
MLS#:
976015
Type:
Single Family
Lot size:
6.87 Acres
Year built:
2003
A broker reciprocity listing Courtesy: BHHS Hudson Valley Properties 845-896-9000
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ADDITIONAL INFORMATION

Imagine turning onto a quiet country road in beautiful Roxbury, Connecticut, passing classic stone walls and mature trees before arriving at a private drive that gently curves you home. Set back on nearly seven acres of peaceful countryside, 380 Southbury Road offers a rare blend of privacy, elegance, and timeless New England charm. From the moment you step through the arched front entry, the home welcomes you with a dramatic two-story foyer and grand staircase, setting the stage for the exceptional craftsmanship found throughout. Natural light pours through floor-to-celing windows with transoms, highlighting rich hardwood floors and refined architectural details including crown molding, tray ceilings, chair rails, and decorative columns. At the heart of the home is a gourmet kitchen designed for both everyday living and entertaining, featuring custom cherry cabinetry, granite countertops, a butler's pantry, and top-of-the-line stainless steel appliances. The adjoining room creates a gathering space perfect for morning coffee or cozy evenings at home. Just beyond, the sunken room with double French doors opens to a seemlessly blending indoor comfort with outdoor living. The upper level features a luxurious primary suite along with three additional spacious bedrooms, providing comfort and privacy for guests. A large bonus room offers incredible flexibility and can easily serve as a den, playroom, office or additional lounge space tailored to your lifestyle. A half bath on the main level adds convenience for everyday living and entertaining. The impressive walk-out lower level adds approximately 1950 square feel of additional living space with 9-foot ceilings, featuring a full bar, recreation room, exercise room, spare bedroom, pre-wired for a home theater, and a full bathroom ideal for entertaining, relaxing or hosting overnight guests. Outside, the property feels like a private retreat. Nearly seven acres of scenic grounds include woodlands trails, a tranquil stream, a charming stone fire pit, outbuildings, and an private inground pool with a stunning two-story pool house. A chicken coop and electric house adds further functionality while preserving the property's country estate charm. Offering exceptional quality construction, remarkable privacy, and convenient access to nearby shopping and restaurants. 380 Southbury Road presents a lifestyle of elegance, comfort, and tranquility. A truly special property that must be experienced to be fully appreciated.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,772
Status:
Active
MLS#:
24159885
Type:
Single Family
Subdivision:
N/A
Lot size:
12.74 Acres
Year built:
1770
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,725
Status:
Active
MLS#:
24158237
Type:
Single Family
Subdivision:
Chalybes
Lot size:
2.97 Acres
Year built:
1973
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

Light-filled, modern living on a private nearly 3-acre corner lot - with room to grow. Set on a beautifully positioned corner parcel, this fully renovated home is defined by natural light and flexibility. Expansive windows and vaulted ceilings create a bright, open feel throughout the main living spaces, bringing in sunlight from multiple exposures and connecting the home to its surrounding landscape. Completely transformed with high-end finishes and energy-efficient upgrades, the home offers the ultimate floor plan, featuring two first-floor ensuite options and close proximity to Roxbury Market, town tennis courts and Hurlburt Park.Beyond what's already been thoughtfully updated, the property offers meaningful future potential. The grounds are well-suited for additional features creating an opportunity to further enhance the outdoor experience over time. Transition to outdoor living through the integrated open porch, featuring a dramatic black-vaulted ceiling and stone tile flooring-ideal for lounging or future screening. The finished lower level adds another layer of versatility, with walk-out access and the ability to evolve with your needs-whether as a pool house, gym, office, creative studio, or additional guest space. A rare combination of move-in-ready ease and long-term optionality, all set on a private and peaceful setting.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,800
Status:
Active
MLS#:
24154135
Type:
Single Family
Subdivision:
Chalybes
Lot size:
3.39 Acres
Year built:
2026
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

This is 'the best deal in Roxbury"! New construction on 3.39 acre lot. The style is a classic farmhouse design Cape with a covered front porch with metal roof. There will be 9' ceiling height on the main level and 8' on the upper level. Both levels will have wood floors. The primary suite is on the main level with a large bath including a shower a free standing tub and a walk in closet. The kitchen is open to the family room which has a bank of 3 sets of sliders to the back deck area and a fireplace on the end wall. The main level includes a formal dining room, formal living room and a main level laundry/mud room. The upper level includes 3 additional bedrooms and 2 full baths. There is a study area as well as a rec room over the garage. The large 2 car garage will have an electric car charger. Still time to help pick out cabinets, countertops, colors, etc. Roxbury is a lovely small town with bucolic farms and farmers markets. It is very sought after for weekend and summer homes. There are many land trust areas for hiking and exploring. The Shepard river is great for fishing and tubing. Litchfield County has many lakes for out door recreation. There are ski areas close by and lots of summer fairs. The area is known for art galleries, antique shops and great restaurants. Taxes TBD

Open House:

Saturday, 5/9 1:30-3:30PM

More Open House Info >

Beds:
4
Baths:
5.00
Sq.Ft.:
3,566
Status:
Active
MLS#:
24152786
Type:
Single Family
Subdivision:
N/A
Lot size:
4.24 Acres
Year built:
1972
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manicured acres with a resortlevel pool, just far enough from the city to exhale, yet close enough to make spontaneous weekend getaways a reality. From the moment you arrive, this summer ready property feels like a private club: stone walls, curated landscaping, quiet woods, and outdoor spaces designed for long summer days and latenight gatherings. The gunite pool is the centerpiece - sparkling, secluded, and ready the moment you are. Inside, sunlight pours through picture windows into an open layout built for effortless entertaining. Custom oak details, a dramatic fieldstone fireplace, and a chef's kitchen with highend appliances and stone counters set the stage for everything from cozy winter weekends to lively holiday hosting. With 4 ensuite bedrooms, the home adapts beautifully to guests and long family weekends. The firstfloor ensuite offers effortless hospitality, while the secondfloor luxury primary suite- complete with 11foot ceilings and a marble spa bath - provides a calm, spalevel retreat. A steelandglass office alcove and a bonus room above the garage with interior access, offering the perfect flex space for a studio, gym, or an additional guest suite. The finished lower level and walkout access adds even more room to unwind. Fully renovated since 2021 including new HVAC, generator, and more means no projects, no delays to start enjoying the Litchfield Lifestyle.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,028
Status:
Active
MLS#:
24153218
Type:
Single Family
Subdivision:
N/A
Lot size:
2.29 Acres
Year built:
2003
Courtesy: Drakeley Real Estate, Inc. 203-263-4336
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ADDITIONAL INFORMATION

This is a wonderful well cared for country home in the beautiful small town of Roxbury. Situated on this dead end road you are minutes to local amenities. Take advantage of nearby hiking trails, parks and open space with Southbury, Bridgewater, Washington and Woodbury town centers just a short drive away. Only 90 minutes from NYC. The first floor has two fireplaces and is open and spacious with French doors from two locations out onto private patios. There are three bedrooms on the second floor with lots of light and charm. Owned by the same owners since construction you can see the care. The first floor has beautiful hardwood floors, a well thought out country kitchen with double ovens plus gorgeous counters and cabinets. with a nearby den and a large living room-dining room with fireplace. Come and enjoy the view of the spacious hills beyond. Schools are part of Region 12 which includes Washington. The owner is a wonderful gardener and her grounds are so enjoyable!

Beds:
4
Baths:
5.00
Sq.Ft.:
4,874
Status:
Active
MLS#:
24146457
Type:
Single Family
Subdivision:
N/A
Lot size:
18.62 Acres
Year built:
1999
Courtesy: Klemm Real Estate Inc 860-868-7313
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ADDITIONAL INFORMATION

NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers scale, privacy, and the relaxed elegance that defines Litchfield County living. Designed for both comfortable daily living and effortless entertaining, the home opens to expansive grounds, a pool, and a setting defined by natural beauty and understated presence. With generously proportioned rooms and a strong indoor-outdoor flow, the property offers immediate enjoyment and the flexibility to personalize over time. Now offered at a compelling new price, this is an exceptional opportunity to acquire a significant Roxbury estate with outstanding value in today's market.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,862
Status:
Active
MLS#:
24147507
Type:
Single Family
Subdivision:
Tophet
Lot size:
6.07 Acres
Year built:
1976
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene landscapes. The idyllic surroundings include a tranquil stream which meanders down through the property, while established mature plantings burst with color and life, providing a private oasis for relaxation and enjoyment. Imagine alfresco dining on the inviting stone terrace, or pursuing your gardening passions in the dedicated garden shed. This home is ready for its next chapter, offering a foundation of classic Cape Cod charm awaiting modern touches. It's an exceptional chance to invest in a lifestyle of peace and natural beauty, surrounded by the distinguished homes that define this desirable corner of rural Connecticut. *Town tax records - 3 bedrooms, health file has 2.

Beds:
5
Baths:
6.00
Sq.Ft.:
5,447
Status:
Active
MLS#:
24146278
Type:
Single Family
Subdivision:
N/A
Lot size:
14.82 Acres
Year built:
1988
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
5.00
Sq.Ft.:
6,169
Status:
Active
MLS#:
24133274
Type:
Single Family
Subdivision:
N/A
Lot size:
8.84 Acres
Year built:
1977
Courtesy: W. Raveis Lifestyles Realty 860-868-0511
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ADDITIONAL INFORMATION

This special home is located in one of Roxbury's most desirable neighborhoods on a quiet dead end road. A long, winding & very private driveway leads up to the commanding double-story porticoed entrance. The traditional colonial layout includes a central chef's kitchen which rests between the formal living, media & dining rooms. The main floor is completed by an office, 2 half baths, and a 2-room bedroom suite - perfect for guests, in-laws, or live-in help. This wing could easily be converted to a main floor primary if desired. Upstairs hosts the current primary bedroom w/ frpl & updated bath, as well as 2 addl bedrooms w/ a shared hallway bath. The updated, eat-in kitchen walks out to an airy screened porch w/ ample space to accommodate both lounging & dining. It is lightly shaded by mature trees and overlooks fieldstone terraces, established gardens & fruit trees. This property offers a uniquely flat and expansive lawn in a truly 'park-like' setting. The previous owner was a master gardener who meticulously cultivated specimen Rhododendrons throughout the lightly wooded surrounds. The mature plantings combine w/ native Mountain Laurel to create a spectacular display in early Summer. The exterior is completed by a 22 x 45 salt water, Gunite pool w/ integrated 6 x 8 Jacuzzi. It is 10' deep & boasts a diving board, retractable cover, & automated chemistry system allowing for hassle free ownership.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,336
Status:
Active
MLS#:
24132367
Type:
Single Family
Subdivision:
Painter Hill
Lot size:
4.96 Acres
Year built:
2001
Courtesy: Klemm Real Estate Inc 860-868-7313
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
24117695
Type:
Single Family
Subdivision:
N/A
Lot size:
8.71 Acres
Year built:
1817
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 8.71 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house, and a separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. 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. Whether you envision building a bespoke estate or simply enjoying the charm and privacy of the existing homes, this rare offering blends history, potential, and natural beauty in one of Litchfield County's most coveted locations.

Beds:
4
Baths:
3.00
Sq.Ft.:
6,395
Status:
Active
MLS#:
24110013
Type:
Single Family
Subdivision:
N/A
Lot size:
3.79 Acres
Year built:
2005
Courtesy: Houlihan Lawrence 203-746-6565
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ADDITIONAL INFORMATION

Looking to escape the hectic pace of city life? Welcome to this peaceful, beautifully renovated 4-bedroom home, originally built in 2005, offering the perfect blend of comfort and tranquility. Featuring 2.5 baths and a spacious open-concept living and dining area, this home is ideal for hosting gatherings and entertaining with ease. The modern kitchen is a dream for any home chef, complete with state-of-the-art appliances, ample counter space, and generous storage. Enjoy stunning outdoor views from every angle and make the most of the inviting outdoor space. Perfect for alfresco dining or simply relaxing in nature. A 3-car garage provides plenty of room for parking, storage, and hobbies. This home offers a wonderful setting to grow and thrive, whether you're raising a family or settling into a peaceful lifestyle. Located in Roxbury, a quiet rural town rich in New England charm, you'll enjoy scenic countryside, historic sites, hiking at Mill Hill Preserve, and local artisanal goods at the Roxbury Market. A true retreat with timeless appeal.

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Davis E. Owen, Sr., License REB.0754414, Xome CT LLC, License REB.0790146 , [email protected], 844-400-XOME (9663), 2083 Main Street, Stratford, CT 06615


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026, OneKey MLS, Inc. All Rights Reserved.



Roxbury 06783 Real Estate

Roxbury is located in Connecticut. Roxbury, Connecticut 06783has a population of 2,104. Roxbury 06783 is more family-centric than the surrounding county with 31.71% of the households containing married families with children. The county average for households married with children is 26.17%.

The median household income in Roxbury, Connecticut 06783 is $107,328. The median household income for the surrounding county is $84,797 compared to the national median of $69,021. The median age of people living in Roxbury 06783 is 53.2 years.

Roxbury Weather

The average high temperature in July is 82.3 degrees, with an average low temperature in January of 14.5 degrees. The average rainfall is approximately 52 inches per year, with 46.4 inches of snow per year.

Roxbury Map

Roxbury Real Estate Market Conditions

  • Median sales price

    $781,250
    13.4%
    change since last quarter
  • # Active listings

    40
    30-day change

Roxbury Schools and Demographics

Education near Roxbury, CT

City County
High School Graduates 97.65 93.89
College Degree - 2 year 3.86 9.19
College Degree - 4 year 61.93 36.19
Graduate Degree 15.42 11.56
Expenditures per Student 26,218 26,218
Students per Teacher 11.5 11.5

Elementary Schools near Roxbury, CT

Grades Students P/T Ratio ZIP
Booth Free School KG - 05 78 7.5 06783
Gainfield Elementary School PK - 05 378 14.5 06488
Integrated Star Preschool Program PK - PK 51 17 06798
Mitchell Elementary School KG - 05 359 14.2 06798
Pomperaug School KG - 05 391 14.4 06488
The Burnham School KG - 05 55 6.6 06752
Washington Primary School PK - 05 153 10.2 06794

Middle Schools near Roxbury, CT

Grades Students P/T Ratio ZIP
Rochambeau Middle School 06 - 08 545 13.3 06488
Woodbury Middle School 06 - 08 364 11.3 06798

High Schools near Roxbury, CT

Grades Students P/T Ratio ZIP
Nonnewaug High School 09 - 12 751 11.2 06798
Pomperaug Regional High School 09 - 12 1,203 13.4 06488

Ungraded Schools near Roxbury, CT

Grades Students P/T Ratio ZIP
* Nonnewaug Chiefs Alternative Program 12 - 12 1 06798
Shepaug Valley School 06 - 12 461 9.1 06793

Demographics near Roxbury, CT 06783

Zip Code City
Neighborhood Type Small town
Population 2,104 185,175
Population Density 80 201
Median Age 53.2 47.6
People per Household 2.2 2.4
Median Household Income 107,328 84,797
Average Income per Capita 77,843 47,811

Real estate near Roxbury