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$3,995,000
5 Beds ⋅ 6 Baths ⋅ 24177581 MLS
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!

47 Squire Rd, Roxbury
$3,950,000
4 Beds ⋅ 7 Baths ⋅ 24192621 MLS
Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

297 Painter Hill Rd, Roxbury
$3,600,000
5 Beds ⋅ 5 Baths ⋅ 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
$3,495,000
4 Beds ⋅ 5 Baths ⋅ 24201025 MLS
Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room w/floor-to-ceiling glass & fireplace anchors the living spaces, opening directly to large deck for effortless outdoor entertaining & picturesque views of the grounds. There are 4 ensuite bdrms, incl a stunning 1st-flr primary suite w/sitting room, gas fireplace, 2 fully built-out walk-in closets, & French doors leading to a private terrace with outdoor fireplace. Cozy library/den with built-ins and a versatile lower-level bonus space are ideal for an art studio or private home office. Add'l highlights incl a steam shower, smart-home features, radiant heat w/hydro-air backup, 2 washers & dryers. Dramatic post-and-beam guest house w/ vaulted ceiling, balcony, & full kitchen sits above a 2 car garage and prep kitchen, offering a private retreat complete w/its own washer/dryer. The grounds are exceptional-mature trees, stone walls, a pond, sweeping lawns, and lush gardens surrounding a heated gunite pool. Expansive porches and terraces provide seamless indoor-outdoor living, ensuring total privacy. Minutes from The Mayflower Inn, town center and close to acres of Roxbury Land Trust. 90 min to NYC.

35 Schoolhouse Rd, Roxbury
$3,200,000
3 Beds ⋅ 2 Baths ⋅ 24186522 MLS
Exceptional equestrian estate featuring a fully equipped horse facility and charming Cape-style home. Ideal for equestrians, trainers, or boarding professionals, the property offers 16 rubber-matted stalls, a large well-lit indoor arena, and a second-floor viewing lounge with kitchen amenities-perfect for lessons, clinics, and entertaining. The barn includes a wash stall, feed room, hay storage, boarder tack lockers, laundry area, and full bath. Safety is enhanced by a commercial sprinkler system. Owned pole-mounted solar panels are installed but are not currently operational. Outside, expansive grass paddocks and a large sand/stone dust outdoor arena provide ample space for training and turnout. Bordering Land Trust property with a river and miles of trails, you can horseback ride or hike directly from your back door. "The Shepaug is one of those rivers that looks like it was painted by someone who had too much talent and not enough canvas." written by Charles Hayes. The Cape-style home features 3 bedrooms and 2 full baths, blending classic New England character with modern comfort. A 2-car attached garage is complemented by a detached 4-car garage, plus an additional detached 3-car garage with a second-floor apartment-ideal for guests, staff, rental income, or a home office.

124 Botsford Hill Rd, Roxbury
$2,750,000
4 Beds ⋅ 5 Baths ⋅ 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
$1,920,000
4 Beds ⋅ 5 Baths ⋅ 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
$1,799,000
5 Beds ⋅ 5 Baths ⋅ 24159852 MLS
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.

2 Pickett Rd, Roxbury
$1,795,000
5 Beds ⋅ 6 Baths ⋅ 24189301 MLS
Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand circular driveway introduces the residence, where sweeping lawns and striking architecture create a powerful sense of arrival, privacy, and seclusion. Inside, light-filled interiors showcase soaring ceilings and oversized windows that capture serene vistas from nearly every room, blending contemporary sophistication with warmth and comfort. The remodeled kitchen serves as the heart of the home, seamlessly combining modern design with functional luxury as it flows into the main living areas. With five generously proportioned bedrooms and six bathrooms, the thoughtfully scaled floor plan accommodates both grand entertaining and intimate everyday living. The lower level features a versatile in-law suite complete with a full kitchen, private bedroom, bathroom, living room, separate entrance, and direct access to the grounds, along with an additional great room or family room that opens to the expansive lawn, offering a seamless indoor-outdoor connection ideal for guests or multigenerational living.

233 Southbury Rd, Roxbury
$1,525,000
4 Beds ⋅ 3 Baths ⋅ 24194995 MLS
This 4 bedroom main house with 2 bedroom guest house provides a peaceful retreat just minutes from town and 1.5 hours from NYC. The cape style main house is privately sited to capture breathtaking western views and sunsets. It features a light-filled open floor plan designed for effortless everyday living and entertaining. French doors open to an expansive deck where sweeping western vistas create the perfect backdrop for relaxing or hosting while overlooking the frolicking horses at the neighboring property. At the heart of the home is a stylish kitchen with a generous center island, ideal for both casual gatherings and inspired culinary creations. The great room incorporates a dining area and seating area with fireplace. The main floor is completed by the primary bedroom with ensuite bath and the 2nd bedroom which is conveniently located adjacent to the primary and could be used as additional closet or office space. Upstairs, 2 bedrooms share a hall bath. An additional 800+/- square feet of walk-out lower-level space has high ceilings and is plumbed for a full bath. It offers potential to create a play room, home gym, media room, or in law suite. The under-house two-car garage offers space for vehicles and/or storage. Complementing the main residence is a 1,400-square-foot ranch style guest house featuring two bedrooms and two full baths on one level, perfect for guests, income, or in-laws.

21 Hemlock Rd, Roxbury
$1,495,000
4 Beds ⋅ 5 Baths ⋅ 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
$1,469,000
4 Beds ⋅ 4 Baths ⋅ 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
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 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
$1,269,000
3 Beds ⋅ 3 Baths ⋅ 24192683 MLS
Completely remodeled 3 bedroom, 2.5 bath open concept home, with two fireplaces (one with wood burning insert), kitchen with stainless appliances, granite counters and large island. Property is private - boarders 18 acre land trust and farm land. Gunite pool (propane heater) with pavilion and fire pit for entertaining. Hot tub off main bedroom patio. Property features stone walls, steps and patios. Generac whole home generator. Detached oversized garage with game room (potential in-law set up). Great home for entertaining.

85 Good Hill Rd, Roxbury
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 24154135 MLS
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

11 Evergreen Dr, Roxbury
$1,195,000
4 Beds ⋅ 3 Baths ⋅ 24192986 MLS
*Completely reimagined from top to bottom, 22 E. Woods Rd. offers the rare combination of virtually new, low-maintenance living, nearly 7 acres of beautiful privacy and exceptional value. WITH JUST $7,395 in annual property taxes, the monthly cost to own and operate this home can be a fraction of what you'll find in many surrounding towns. Inside, gleaming hardwood floors, abundant natural light and an inviting open floor plan create a warm, comfortable atmosphere. The stunning custom kitchen features crisp white and natural-tone cabinetry, granite countertops and high-end stainless-steel appliances, flowing seamlessly into the living spaces anchored by a charming fireplace. The spacious primary suite offers a spa-like bath with soaking tub and oversized tiled shower, walk-in closet and separate flex space perfect for an office, nursery or dressing room. Three additional bedrooms share a brand-new full bath, while a bonus room over the garage-with its own staircase-offers even more flexibility. Outside, front and rear patios provide wonderful spaces for relaxing or entertaining while nearly 7 acres offer privacy and room to enjoy the outdoors. Freshly painted inside and out, with a new roof and driveway, this home is truly move-in ready and designed for worry-free living. Nearly a complete renovation, incredibly private, low taxes and a remarkably low cost of ownership-this is a rare opportunity to enjoy a nearly new home with the space and privacy you've been looking for!

22 E Woods Rd, Roxbury
$998,000
3 Beds ⋅ 3 Baths ⋅ 24204225 MLS
Tucked away on a highly sought-after country road, this charming Colonial has been lovingly maintained by its original owners and offers privacy, lovely grounds, and exceptionally low taxes. Distinctive character begins with its graceful rounded-front porch and continues throughout this exceptionally well-built home, where timeless craftsmanship meets enduring charm. A welcoming foyer features a distinctive staircase to the upper level and opens to the living and dining rooms on the left, while a cozy den flows into the bright eat-in kitchen on the right. The laundry and half bath are conveniently located just off the kitchen. Beautiful hardwood floors, two fireplaces, and French doors leading to private patios create inviting spaces for everyday living and entertaining. Upstairs, the spacious primary suite offers walk-in closets and a well-appointed bath with Jacuzzi and large separate shower. Two additional bedrooms feature generous closets, complemented by a large linen closet. This well loved home is on a beautiful lot, at an approx. 1000 ft elevation, has mature landscaped grounds, private patios and a cute garden shed creating a peaceful country retreat. There is an approx 1,100 sq ft basement with tall ceilings offering a great expansion opportunity, or excellent for storage. Roxbury is a quintessential New England community with very low taxes and home to well-regarded schools. It is also known for its natural beauty, historic character, and strong sense of community.

16 Jonathan Dr, Roxbury
$995,000
4 Beds ⋅ 4 Baths ⋅ 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
$985,000
3 Beds ⋅ 2 Baths ⋅ 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
$969,000
4 Beds ⋅ 3 Baths ⋅ 24167690 MLS
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!

23 Painter Hill Rd, Roxbury
$969,000
3 Beds ⋅ 3 Baths ⋅ 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
$950,000
3 Beds ⋅ 4 Baths ⋅ 24157035 MLS
Discover modern serenity in this private contemporary retreat nestled on 3.44 private acres. The ascending driveway assures a sense of quiet and seclusion, leading you to a home bathed in natural light from a soaring two-story wall of south-facing windows, this home perfectly blends architectural drama with a peaceful woodland backdrop. The exterior features an expansive, brand new composite deck with its sleek cable railing system--perfect for al fresco dining or quiet mornings. Inside, the light filled, open-concept main level is anchored by 5 1/4" hardwood oak flooring and a dramatic granite gas burning fireplace. A full wall of custom built in's create style and ample storage. The kitchen is designed for functionality with its central island, quartz countertops and new Fulgar Milano induction range and a new LG refrigerator. Retreat to the main-level primary on-suite, which offers its own private deck access via French patio doors. Upstairs, a glass railed loft provides additional flexible space. The fully tiled walk out lower level includes a full bath offering excellent potential for an in law apartment, guest suite or private home office with a 2nd laundry hook up area in the garage. Meticulously maintained and newly painted throughout, this sanctuary is equipped with radiant heat, central air, a main level laundry and a newer water softening system.

28 Garnet Rd, Roxbury
$850,000
3 Beds ⋅ 2 Baths ⋅ 24180161 MLS
Own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic property and make it your own. A welcoming foyer greets you upon entry and leads to a spacious formal living room featuring a classic fireplace. The sunroom is complete with a wood-burning stove. Upstairs, you'll find three bedrooms, including one pass-through bedroom that offers flexibility for a nursery, office, sitting room, or guest space. A full bath serves the second floor. The home's unique feature may be the finished walk-up attic, complete with a working sink and endless possibilities as an artist's studio, creative workspace, hobby room, or private retreat. Recent improvements include a professionally installed Connecticut Basement Systems waterproofing system, featuring a new sump pump and dehumidifiers to help maintain a clean, dry basement year-round. Filled with memories, history, and timeless architectural details, the Philo N. Hodge House is ready for its next chapter. Buyers are encouraged to conduct their own due diligence with the Town of Roxbury regarding any regulations, permits, approvals, historic preservation considerations, or future improvements to the property.

47 South St, Roxbury
$760,000
3 Beds ⋅ 3 Baths ⋅ 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
$725,000
5 Beds ⋅ 3 Baths ⋅ 24178189 MLS
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.

50 Southbury Rd, Roxbury
$725,000
3 Beds ⋅ 3 Baths ⋅ 24175557 MLS
This handsome 1820's Colonial, set behind large shade trees on 1.33 acres just off the Green, is an easy walk to the Library, Booth School, Apple Lane Park, Churches, Tennis courts, and a morning cuppa at the Roxbury Market. Major renovation in 2018 included New HVAC, New wiring, Rebuilt Porch and more. New Well installed dedicated to this property replaced shared source. Interior makeover included fine Kitchen with gas range and quartz counters, formal Dining room or Library, Powder Room, and front-to-back Living Room leading to full-width covered porch overlooking the lawn, wonderful for entertaining. The Main floor shines with wide-board oak floors, thermal windows and traditional trim. Greet the morning sun in the second floor primary Bedroom with ensuite bath and walk-in closet. Two other bedrooms and hall bath also share this floor. Stairs lead up to the third floor and two more finished rooms. Level lawn behind the house extends back to a large barn with water, electric and a poured concrete floor for garage or many other creative uses. There's so much here in this inviting antique Roxbury home that lives like new!

20 Wellers Bridge Rd, Roxbury
$589,990
3 Beds ⋅ 3 Baths ⋅ 24197040 MLS
A former artist retreat is waiting for you! This Ranch/Rambler style home boasts an open concept with vaulted ceilings. Enjoy all the privacy that Roxbury and the Litchfield Hills offers, yet have convenient access to major highways. The home offers 3 bedrooms and 3 full baths. There is opportunity to convert the lower level into a in-law space should you desire. The outdoor space is primed for your entertaining desires or if you prefer, curl up to a book or a cocktail on the patio, deck or porch. Opportunity is knocking...call for an appointment.

21 Carriage Ln, Roxbury
$575,000
3 Beds ⋅ 3 Baths ⋅ 24197990 MLS
Diamond in the rough! This solid and expansive home is waiting for its new life, with you as the steward. It has 3 good sized bedrooms, a bonus room off the primary (which is ensuite), a large partially finished lower level, perfect for a game room, gym, man or woman cave, an open floor plan from the kitchen to the family room, a multi-level deck, an oversized 2 car garage and a large, beautiful yard lined by beautiful stone walls with perennial beds, all located in the highly desirable town of Roxbury, where the average sale price is well north of $1M. 90 minutes to Manhattan, this is southern Litchfield County, so you get the beauty and cultural life found locally, with proximity to Westchester, Fairfield and NYC. Great hiking, restaurants and art abounds within minutes. This is an as-is sale, with the price reflecting the condition of the property. There will be no seller concessions for inspection issues.

90 Mallory Rd, Roxbury
$575,000
2 Beds ⋅ 2 Baths ⋅ 24182244 MLS
Best Litchfield County Opportunity! Escape to your own peaceful country retreat with the perfect blend of comfort, character, and privacy on nearly 5 acres of wooded wonderland. Less than 2 hours from NYC, this home has lots of character and a flexible layout with 2 bedrooms, 2 full bathrooms plus an upper level guest room/office/rec room. Main floor layout with separate spaces set up well for relaxing or entertaining, and a kitchen with plenty of prep and storage space. Expansive wrap-around deck outside - the perfect spot for morning coffee, al fresco dining, or simply unwinding and unplugging while enjoying the sights and sounds of your private pond and surrounding woods. Nature lovers will appreciate the serene setting that offers privacy and tranquility. Hikers and bikers will gravitate to nearby trails on the Roxbury Land Trust. The town of Roxbury has long been sought-after as a convenient country getaway providing small-town Connecticut living but so close to Westchester and the city. Very convenient to shopping in nearby towns of Woodbury and Southbury.

188 Bacon Rd, Roxbury

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