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$1,235,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192986 MLS
Completely reimagined from top to bottom, 22 E. Woods Rd. is a home where elevated design meets everyday comfort. From the moment you step inside, gleaming hardwood floors, abundant natural light, and an inviting open floor plan create a warm and welcoming atmosphere that feels equally suited to quiet mornings and lively gatherings. At the heart of the home is a stunning custom kitchen featuring a beautiful blend of crisp white and natural-tone cabinetry, granite countertops, and high-end stainless steel appliances. The adjoining living spaces flow effortlessly together, anchored by a charming fireplace that adds warmth and character. The primary suite offers a private retreat, with a spa-like bathroom featuring a luxurious soaking tub and oversized tiled shower, a walk-in closet, and a separate flex space ideal for a nursery, dressing room, or home office. Three additional generously sized bedrooms share a brand-new, beautifully appointed full bathroom. Don't miss the bonuses room with separate staircase over the garage perfect for a home office, den or other uses. Outside, front and rear patios extend the living space and offer inviting spots to enjoy a morning coffee, gather with friends, or simply relax. Freshly painted inside and out, with a new roof and driveway, this exceptional home offers the rare opportunity to enjoy the a near completely new property while still feeling unmistakably like home.

22 E Woods Rd, Roxbury
$1,295,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193455 MLS
A custom-designed Judds Bridge Colonial in a coveted location, privately set amid mature trees and established plantings. A dramatic double-height marble foyer introduces the home's beautiful architectural millwork and rich cherry floors on the main level. The well-proportioned interiors include formal living and dining rooms, office or bonus room, an open and eat-in kitchen with solid cherry cabinetry, double oven, cook top, peninsula with seating, pantry, powder and laundry room, and a spacious den with vaulted ceilings, antique beams and centered around a soaring Rumford fireplace. The primary suite features a tray ceiling, en-suite bath with double sink, generous walk-in closet, while three additional bedrooms share a full bath. Out the French doors onto Ipe deck provides a refined setting for outdoor living and your private back yard. Additional highlights include a three-car garage, an unfinished bonus room over the garage that offers excellent expansion potential, new UV paned deck doors, updated mechanicals, architectural roof shingles, and a portable generator. Quintessential New England living at it's best!

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

47 South St, Roxbury
$1,795,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24171982 MLS
Sprawling 4-bedroom colonial as part of a peaceful and private 17-acre estate in desirable Roxbury, CT. Sighted well on open rolling lawns with sweeping sunrise/sunset views, this property offers country living with exceptional versatility. The sun-filled eat-in kitchen features has sliders that open to a jumbo 58' deck with awning and open views. Generous main-level spaces include a dramatic family room with vaulted ceilings, wood-paneled dining room, living room with fireplace, large office/den/library, laundry room, and powder room. Upstairs are four bedrooms and two baths, including a spacious primary suite with walk-in closets and dressing area. The lower level has lots to offer with another half bath, gym/workout area, lots of storage and access to the 2-car garage. Outside, the spotlight is on the Pebbletec saltwater pool that is beautiful and low maintenance. The property has an abundance of open space and open sky in all directions. Multi-stall barn with hay loft and a 930 sq ft apartment, offering flexibility for equestrian pursuits, collector storage, creative studios, wellness uses, and income potential. Plus, detached 3-bay garage and a whole-property generator. Truly perfect for those seeking a country retreat or a gentleman's farm, and only 90 minutes from NYC - near Woodbury and part of the Washington-Roxbury corridor. Welcome home to Litchfield County!

25 Highmeadow Ln, Roxbury
$1,895,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24170163 MLS
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!

18 Ranney Hill Rd, Roxbury
$998,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24169438 MLS
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.

336 South St, 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
$1,099,000
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
$679,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24162576 MLS
Step back in time with this historic 1800s Colonial that retains its original character and charm while offering modern amenities, including an updated kitchen and bathrooms. The home features four bedrooms upstairs with wood floors, including a primary bedroom with an attached room currently used as an office. The main level with a den, living room with fireplace, dining room, and a mahogany-floor kitchen. Plus a mudroom/laundry room leading to the back patio. A large barn provides ample storage, and the property includes a 1,250-gallon 4-bedroom septic tank installed in 2008, a fully fenced backyard, and a 24-foot-wide new asphalt driveway. Recent upgrades include a new barn roof and framing, new 200-amp electrical panel and some wiring in the main house, insulated exterior walls, remodeled shower and fireplace, new wainscoting in the upstairs hallway, new glass backsplash in the kitchen, and restored original wood floors upstairs. Enjoy relaxing on the front porch or rear stone patio and take advantage of nearby hiking trails, parks, and open space, with Southbury, Bridgewater, and Washington town centers just a short drive away. Confirmed appointment required for showings.

216 Baker Rd, Roxbury
$1,549,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24163570 MLS
Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room, spacious dining room and chef's kitchen with striking polished hardwood center island. Upstairs, Primary En Suite Bedroom with lovely clawfoot tub, double sinks, large separate shower and spacious dressing room. Two more bedrooms share a charming hall bath. Finished lower level currently outfitted as a family room with French doors to a serene patio leading out to the pool, another en suite bedroom and two more finished flexible spaces. (Makes the total finished sq feet: 3676!)The perfect peaceful location, minutes from the centers of Roxbury and Washington. Must see!

33 Sentry Hill Rd, Roxbury
$1,025,000
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
$1,550,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24162311 MLS
Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray ceilings, and abundant natural light throughout. The gourmet kitchen features custom cherry cabinetry, granite countertops, stainless steel appliances, and a butler's pantry, opening to a warm hearth room with a fieldstone fireplace. A sunken family room with a brick fireplace and French doors leads to a stone patio, creating an ideal flow for indoor-outdoor living. The upper level offers a spacious primary suite, three additional bedrooms, three full baths, and a versatile rooms suitable for a home office, lounge, or playroom. The walk-out lower level with 9-foot ceilings provides approximately 1,950square feet of additional living space, including a recreation area, full bar, exercise room, bedroom, full bath, and flexible space for entertaining or extended living. The grounds offer a peaceful retreat with woodland trails, a stream, fire pit, outbuildings, and a two-story pool house. Additional features include a chicken coop and utility structure, enhancing the property's country lifestyle appeal. Conveniently located near local amenities while offering privacy and tranquility.

380 Southbury Rd, Roxbury
$985,000
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
$1,949,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24146457 MLS
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.

1030 Washington Woodbury Rd, Roxbury
$760,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24132367 MLS
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.

38 W Mountain Ln, Roxbury
$1,495,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24110013 MLS
Welcome to 99 Carriage Lane, a private Roxbury estate offering over 6,000 square feet of refined living space, exceptional privacy on nearly four acres, and the opportunity to create a true resort-style outdoor retreat with approved pool plans. Set at the end of a quiet cul-de-sac, this beautifully renovated residence blends timeless architectural details with modern amenities and sophisticated country living. Designed for both comfortable everyday living and effortless entertaining, the home features a stunning chef's kitchen, dramatic family room with soaring ceilings, multiple fireplaces, spacious bedroom suites, and thoughtfully designed living spaces throughout. The expansive interiors provide flexibility for today's lifestyle, including dedicated areas for work, relaxation, and gathering with family and friends. The private grounds offer a peaceful backdrop with mature landscaping, stonework, and room to bring the outdoor vision to life. Approved plans for an inground pool provide the opportunity to further enhance this exceptional property and create a private backyard sanctuary. Located in one of Litchfield County's most desirable communities, 99 Carriage Lane offers the perfect balance of privacy, elegance, and convenience. With nearby villages, dining, recreation, and easy access to New York City.

99 Carriage Ln, Roxbury
$3,395,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24057876 MLS
A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in the beautiful Litchfield Hills with spectacular views that go on for miles. This property includes a four bedroom, five and a half bath main residence, in ground heated Gunite pool, tennis court, one-bedroom caretaker's apartment over a 3-bay garage, two bedroom guest apartment and greenhouse. This compound offers an intriguing mix of elegant sophistication and quiet country road living. Highlighted by judges paneling, the large two-story main foyer is breathtaking. An evening soiree for a large gathering of guests is easily achieved in the public rooms. Both rooms offer a touch of grandeur with extra tall ceilings, tall windows and exquisite detailed moldings. The formal dining room is generous in size with tall windows. The home also offers an array of comfortable spaces for intimate gatherings. The delightful and sunny great room includes the updated kitchen with dining, sitting area with fireplace bordered by floor to ceiling bookshelves and French door that leads to the deck overlooking the magnificent view. There is a family room with fireplace, rec room and full bath in the walk-out lower level. The main floor primary suite is extra special with a fireplace, French doors to brick terrace, and full bath with sauna. The three additional bedrooms, all with full baths, are nicely sized. Special in every way and just 90 minutes from NYC.

11 Ravenrock Rd, Roxbury

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