Roxbury CT Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
2,489
Status:
NEW LISTING
MLS#:
24180161
Type:
Single Family
Subdivision:
N/A
Lot size:
4.47 Acres
Year built:
1833
Courtesy: Berkshire Hathaway NE Prop. 203-264-2880
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
3.00
Sq.Ft.:
1,365
Status:
Active
MLS#:
24178189
Type:
Single Family
Subdivision:
N/A
Lot size:
2 Acres
Year built:
1817
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
6.00
Sq.Ft.:
7,121
Status:
Active
MLS#:
24177581
Type:
Single Family
Subdivision:
N/A
Lot size:
8.03 Acres
Year built:
1984
Courtesy: Klemm Real Estate Inc 860-868-7313
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ADDITIONAL INFORMATION

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!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,990
Status:
Active
MLS#:
24177292
Type:
Single Family
Subdivision:
Judd'S Bridge
Lot size:
8.7 Acres
Year built:
1956
Courtesy: W. Raveis Lifestyles Realty 860-868-0511
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ADDITIONAL INFORMATION

Location! Once in a blue moon, a piece of property becomes available in one of the most desirable Roxbury locations. On a quiet dirt road, nearly 9 acres of privacy and tranquility. One level cottage and two substantial barns. Enter through a field gate with an easy paved driveway, to this rural compound, tucked in, with pretty rolling land and woods. This comfortably laid-out home has slate floors, most of the rooms have radiant heat flooring. The vaulted living room has a central wood-burning fieldstone fireplace. There are two additional propane fireplaces - one in the sunroom, the other in a den. There are 7 mini-splits throughout for heat and ac. The land is private, with some clearings. An approximate 25' x 40' carriage barn, and the other barn is a six-stall horse barn complete with tack room, run-in shed, and electric service. There is significant road frontage buffered by trees. Peaceful and nestled in, this property can be made into your dreamscape. Do not go to property without an appointment. Video cameras. NOTE: Items such as matts, rugs and storage boxes have been removed from photos. Photos otherwise have not been altered.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,059
Status:
Active
MLS#:
24175557
Type:
Single Family
Subdivision:
N/A
Lot size:
1.33 Acres
Year built:
1820
Courtesy: Klemm Real Estate Inc 860-868-7313
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ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,614
Status:
Active
MLS#:
24174231
Type:
Single Family
Subdivision:
Painter Hill
Lot size:
2.27 Acres
Year built:
1983
Courtesy: The Provino Group LLC 203-241-4550
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,782
Status:
Active
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:
Active
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, 6/20 2:00-3:00PM

More Open House Info >

Beds:
4
Baths:
4.00
Sq.Ft.:
4,310
Status:
Active
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

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!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,198
Status:
Active
MLS#:
24170163
Type:
Single Family
Subdivision:
Painter Hill
Lot size:
5.42 Acres
Year built:
2018
Courtesy: William Pitt Sotheby's Int'l 860-868-6600
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ADDITIONAL INFORMATION

Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble tech finish was installed with fencing in the rear yard for the pool and pets. The house was originally built by a Master Craftsman with the finest materials.The gourmet kitchen is where everyone lives. There is a center island and field stone fireplace. Thermador appliances include a 6 burner cook top as well as wall oven, built in microwave, a warming drawer, dishwasher and refrigerator. The open floor plan allows you to set up the living room/dining room in a variety of ways. There is a lovely sunroom with a vaulted ceiling off the kitchen. There is a mudroom coming in from the garage with a half bath. The ceilings are 9' on the first floor. The upper level includes a lovely Primary Suite with walk in closets, a luxurious primary bath with 2 sinks, a walk in shower and a soaking tub. There are 3 additional bedrooms on the upper level with one en-suite and the other two sharing a hall bath. The house sits up high with mountain views. The land is gently sloping with a level area with plenty of room to play. Only 90 minutes to NYC!

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 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.

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, a Sub-Zero refrigerator 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, partially furnished with new furniture included, two-car garage underneath, an expanded driveway (30k), and a charming stone walkway that enhance the property's natural beauty. For those seeking a touch of homestead living, the property also features a professionally built chicken coop - perfect for raising chickens and enjoying fresh eggs at home. A rare opportunity to enjoy tranquility, space, and convenience, just 90 minutes from NYC.

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:
5
Baths:
5.00
Sq.Ft.:
3,326
Status:
Active
MLS#:
24159852
Type:
Single Family
Subdivision:
N/A
Lot size:
8.35 Acres
Year built:
2026
Courtesy: William Pitt Sotheby's Int'l 860-927-1141
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ADDITIONAL INFORMATION

Presenting a truly rare opportunity for BRAND NEW CONSTRUCTION in Roxbury, CT, this luxury residence offers approximately 3,300+ SF of meticulously designed living space, including a spacious finished basement & attached double garage. Enjoy exquisite finishes throughout, highlighted by 6" white oak hardwood flooring, custom architectural millwork and decorative shiplap details. The gourmet Kitchen is designed with a farmer sink, pot filler, stone countertops and high-end stainless steel appliances including double wall ovens, LP gas cooktop & microwave drawer. The open plan Living Room centers on a remote-controlled LP gas fireplace with stone surround and features a dramatic 16' wide x 8' high Andersen sliding glass door leading directly to the outdoor entertaining space. Two additional rooms could serve as a study/den and a formal dining room. A main-level Primary Bedroom offers a generous walk-in closet and en-suite bath featuring a spa-like experience with double shower systems, zero-clearance shower floor with a linear drain and wall-to-wall glass. The powder room and Mud room (with laundry) complete the main level. Upstairs there are two bedrooms which share a full bath, a large bedroom with an en-suite bath, and a large walk-in attic (approx 800 sq ft) ready for optional future finishing. Further living flexibility is provided by an expansive 41' long finished lower level and a full bath.

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
View additional info

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

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
View additional info

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
View additional info

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:
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
View additional info

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.

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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 Real Estate

Roxbury is located in Connecticut. Roxbury, Connecticut has a population of 2,104. Roxbury is more family-centric than the surrounding county with 31.41% 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 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 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

    $1,005,000
    13.4%
    change since last quarter
  • # Active listings

    41
    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

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

City County
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