Roxbury CT Real Estate & Homes for Sale

Many new renovations in this stunning antique home on a quiet country road. All flat usable land with gorgeous bank barn, gunite pool, Spectacular mature trees, and pond. Town has house listed as 5 bedrooms. The primary bedroom with walk in closet is on the main level. Upstairs is more efficiently used as 2 suites each with walk in closets or offices. Alternately, one of the larger bedrooms could be used as a shared play room with 3 bedrooms circulating it. Antique floors and hand hewn beams throughout. The large cooking fireplace has been revived to its former glory and the 2 smaller fireplaces have had propane inserts added. Recent upgrades include: Generator, all new HVAC, interior and exterior paint, wood shingle roof, built ins, curtains etc. Tennis court was partially removed, foundation still in place. Buyers can rebuild it or scrape concrete and create additional lawn or gardens.

Ultimate Charm in this lovingly updated antique on one of the best streets in Roxbury. 3 bedrooms with main level primary that walks out to garden. Surprisingly open floor plan with new mudroom/laundry/powder room addition. Brand new wood shingle roof. Local Engineer has provided maps proving a code compliant pool site and the possibility to finish above the garage into a guest apartment. Walk to land trust trails along Jack's brook. Stone wall, terraces, glorious gardens, mature trees.

Absolute peaceful, quiet and private Paradise with views and endless Possibilities. Immerse yourself in tranquility with this custom-built 5 bedroom Cape Cod estate boasting 900 feet of private frontage and captivating seasonal vistas. This expansive property offers the ultimate in privacy and flexibility, perfect for multigenerational living, entertaining, or simply enjoying the peace and quiet. Unwind in the grand entry foyer, leading to a dramatic great room with a soaring ceiling and a wall of windows showcasing the property's breathtaking beauty. The open concept floor plan seamlessly connects the great room to a chef's kitchen featuring a granite island, breakfast nook, and abundant cabinetry. Step out onto the expansive new 55-foot deck, ideal for al fresco gatherings with stunning seasonal views as your backdrop. The main floor master suite provides a haven of relaxation with a luxurious bath and an oversized walk-in closet, accompanied by a convenient home office. Upstairs, two generously sized bedrooms share a full bath, while one boasts an additional bonus space ideal as a playroom or extra office. This exceptional property caters to extended family or guests with a dedicated in-law suite accessible both from the main house and through its own private entrance. This self-contained haven features a four-room layout, including two bedrooms, a cozy living room with a fireplace, and a spacious kitchen with a dedicated dining area. The possibilities are endless..

Seclusion in Rural Roxbury. Tucked back on dirt road, 10 acres surrounded by nature, trees, birds, and wildlife..... Custom home has a mix of palladium windows, skylights, vaulted ceilings, interior balconies, three fireplaces, eclectic chandeliers and open spaces all add a Contemporary Flair to this colonial home. Primary suite with sitting area and fireplace. First floor ensuite bedroom, French doors exit to back decking - au pair? live in help? multigenerational living? CHECK, CHECK AND CHECK! Be sure to look at the attached floor plan to see the extra study, second floor reading space and very flexible floor plan. Have fun updating it and making it your own peaceful respite. Subject to lot line revision - in the process, application submitted. Taxes will be adjusted accordingly upon approval. Fresh paint in and out, new oil tank, all hardwood just refinished on both floors.

Welcome to Hollywood Hills meets Roxbury! This exceptional 4-bedroom, 3-bath home sits on 2.1 acres and features a vast studio perfect for artists, Pilates, yoga, or entertaining! The light-filled home boasts a gourmet eat-in kitchen with custom cabinetry, imported Spanish floor tiles, and top-of-the-line appliances, including a Subzero refrigerator, Wolf range/grill, Wolf wall oven, and Bosch dishwasher. French doors open to a sprawling deck offering breathtaking views. The living room features two sets of French doors leading to the deck, a fireplace designed by Connecticut artist, Elizabeth McDonald, and custom bookcases. The main level includes a primary bedroom with an ensuite bath featuring a soaking tub, a second bedroom, an office, and a guest bath. The lower level offers two more bedrooms, a windowed bath with a rain shower, a sauna, a laundry room, and a large rec room with easy access to a gunite infinity pool and beautifully landscaped gardens featuring local fieldstone and quarry-mined slabs comingled with perennials. Additional highlights include a detached 2-car garage, new HVAC installed in 2020, a Generac generator, laundry shoot and a DuraSlate roof. Located in the center of Roxbury, walking distance to the Roxbury Market, bank, post office, tennis courts, library, hiking trails and town park. This home seamlessly blends modern amenities with classic charm, offering both privacy and convenience.

Privately set and just a little out of the way sits this well built ranch on 11.4 wooded acres with stone walls and a gentle stream. Property borders 119 acre Roxbury Land Trust. Simple as it seems, it's a perfect place to get out of dodge. Having relatives in the construction business, this home was constructed with Quality, Quality, Quality with energy efficiency in mind. A 3 acre parcel encompasses the driveway you share with two other homes along with the maintenance too. One level with a wonderful floor plan for easy living and a walk up to the storage above if you ever want to put on a second story that it's built for. Windows and doors are Andersons and the furnace is only 2 years old. New AC in 2021. New water heater in 2024. Generator hook up and plywood subsiding for clean living. Beautiful brick fireplace, hardwood floors. They have built the canvas, now you can add the color and decor. Come enjoy the peace and quiet this property has to offer.

Welcome to 66 and 68 Bacon Rd, where a new owner's vision and the opportunity to make a property their own intersect; self-sufficient, income producing, family compound, horse farm with access Roxbury's bountiful trail-riding, organic farm, weekender's retreat, workshops for equipment, motorcycles, mountain bikes, an authentic, exciting moment to create your own country home. Originally, the Daniel Burritt Homestead, a property on 6 bucolic acres, features 2 antique homes, circa 1800, a mammoth barn listed in Historic Barns of CT, with 9 horse stalls. The main house, #66, a triple-barrel colonial still retains many of its period architectural details, includes 3-beds, 1.5 baths and two large fireplaces. A front porch overlooks a large meadow, turnout for horses. The second, #68, a single-family home with updates, originally a carriage house, has 3 beds, 1.5 baths and 3-car garage; it is currently a tenant-occupied, income-producing rental; a turnkey Airbnb opportunity. All three structures have new architectural shingle roofs, the 2 houses have newer furnaces, houses have separate septic systems. Both houses and barn share a well. Nestled in the foothills of Litchfield County, the best of both worlds awaits, far from the hustle and bustle of the outside world, yet close to shopping, dining, I-84, and under 2 hours to NYC. A rare find with TLC to create your dream home. Property is sold "AS-IS".

This Roxbury Colonial is ready for the next owner to sit back and relax on the inviting front porch or invite the friends over to celebrate in any of the multitude of entertaining areas! The open floor plan creates a warm place for family and friends to gather. With a primary en suite, 2 bedrooms that share a full bath and the bonus room over the garage, upstairs, this home is the definition of family. Why not head to the dry lower level with high ceilings to spend some time doing what ever is is you love most. Make it a home gym, game room, or simply added space for entertaining or storage. The options are endless. What more can you ask for outside? How about a game of basketball on the approximately 24x30 foot court? Potential pool site on the right side of the home or keep it simple and relax by a fire on your private bluestone patio, all while enjoying the sounds nature. When designing the home for his family the Seller created a potential site for another garage, if one were to make the garage a first floor primary. Also a 4 bedroom Septic system! The layout is perfect! Make your appointment today to discuss!

**Foreclosure Sale Alert! ** Are you looking for an amazing investment opportunity in Roxbury, Connecticut? Look no further than 24 Baker Rd.! This charming property is now available as a foreclosure sale, offering a chance to make it your own at a fantastic price. **Bedrooms:** 4 **Bathrooms:** 2F, 1H **Square Footage:** 2,431 sqft **Lot Size:** 4.28 acre This property has so much potential - whether you're looking to renovate and flip for profit or create your dream home, 24 Baker Rd. is the perfect canvas for your vision. Located in the picturesque town of Roxbury, known for its scenic beauty and tranquil surroundings, this property offers a peaceful retreat away from the hustle and bustle of city life. Don't miss out on this incredible opportunity to own a piece of Roxbury at a great price! While there maybe 5 potential bedrooms the septic is only for a 4 bedroom home. So make one room a den or study. Water is not on so lender will have to acknowledge that they will lend with no working water.

Enchanted Garden. New to the market after 25 years is this charming 4-5 bedroom home on two magnificent park-like acres with a seasonal view. The first-floor layout includes a living room with fireplace, dining room, kitchen, great room with vaulted ceiling, wood burning stove and sliders out to the deck and pergola covered with hanging hydrangea, powder room, laundry room and a comfortable size primary bedroom suite. Upstairs there are four additional bedrooms, one currently used as an office, and the other currently used as a large closet but it could easily be a baby's nursery. These rooms share a full hall bath. While the house needs the discerning eye of a new owner to bring it to its true potential there is much to boast about. A brand new five-bedroom septic, a dry and spacious basement for additional space, an attached two-car garage and yes those stunning gardens and mature shrubs. The property offers several possible locations for a pool.

Set on 14 private and fully fenced acres, this truly spectacular property, once owned by Walter Matthau and his wife Carol Grace, is surrounded by the Matthau Land Trust. The newly built main house was conceived by Geoff Fairbairn, a well-known Litchfield builder, with the current owners adding more features and square footage to the compound, with an eye for detail and enchanting style. The two original cottages have been updated, keeping the historic touches, and are currently used as a guest house and an extensive gym and office area. Among the many things that make this property so special are an attached five-car garage, a pool with spa and sun deck, radiant heat floors, a magnificent 18-foot stone chimney designed by Jorge Criollo and a three-season screened-in porch complete with a Malm fireplace. Roxbury is a renown artists community, home to such former and current notables as Richard Widmark, Walter Matthau, Marilyn Monroe, Arthur Miller, the illustrator Barry Blitt, the authors Frank & Ellen McCourt, Daniel Day Lewis, James Taylor and the stunning Alexander Calder Estate with its many sculptures. Roxbury's proximity to the city has made it possible for the current owners to easily film in the city and return in just over an hour and a half!

Stylish Private Modern with Infinity Edge Heated Pool. This Hip Modern Home Has an Open Floor-plan & Airy Feel. 3 Bedrooms, 3 Updated Baths. Inviting Eat-in Kitchen Speaks to Large Family Room with Fireplace & Vaulted Ceiling. Wonderful Formal Living Room with Modern Fireplace & Vaulted Ceiling. Generous Primary Bedroom Commands the Upper Level Features Dressing Room & Updated Bath. Main Level Bedroom & Bath + Separate Lower Level Bedroom & Bath. Screened-in Porch. Hot Tub. Separate Detached 2-Car Garage with Studio Above.

Newly renovated home in quiet, desirable Roxbury location. New kitchen and baths, wood beams, central air conditioning, roof, paint etc....turn key. Large eat-in kitchen with fireplace, formal dining area, living room with fireplace, den, full bath, mud and laundry rooms all on main level. 3 bedrooms on second floor including large primary suite. 3 full baths in all. Wooden deck off rear of house and former pool shed on upper terrace. Attached 2 car garage with possible expansion space above. Just charming.

Revolutionary war General, Ephraim Hinman, built this lovely house in 1784. Listed on the NR of Historic Places, this two-story home, 3,666 square foot home with 9-foot ceilings throughout, three bedrooms, two full baths and one-half bath. There is a library with built-ins, living and dining rooms, sitting area, sunroom, study (or 4th bedroom) and all contain original or restored (1930s) dentil & moldings. There are four working fireplaces, and the center hall is covered in early 20th century hand-painted chinoiserie wallpaper. The kitchen is vast, with a custom soapstone sink, Liebherr refrigerator, and a CornuFe stove, and includes a light-filled sitting area & mudroom. Recent improvements include restored scullery kitchen with under-floor radiant heat, cedar shake roof w/40 yr. warranty, new furnace, water filtration and softener system, French drains outside house perimeter and in basement, and a (local) granite patio. The exterior has recently been painted. The garage has room for two cars and more, with loft space. The yard has dry stone walls, wildflowers, a meadow, a large, fenced vegetable garden area, and a bocci court, which is surrounded by heirloom apple trees. Mature plantings and trees provide the necessary shade and greenery for keeping the house cool all summer. Litchfield County has an abundance of outdoor activities, lovely boutiques, antique shops, and dine in farm to table restaurants. Welcome to Litchfield Hills!

In the late 18th century Phineas Smith built the house and office where he laid out plans for the Oxford Turnpike now Southbury Road. This finely preserved home has four working fireplaces and beautiful historic details. Barn has been sensitively converted into modern studio and is currently a successful Architecture office and Antique Shop. Barn/office/studio is 3436 s.f. with heat and a/c, has 2 half baths and Pantry. Both house and barn with featured in Architectural Digest. Super visibility combined with exquisite grounds and lovely pond. Live the genteel country life and stroll to your office, surrounded by nature. Enjoy the benefits of easy living, ideal location - an exquisite property at the crossroads- convenient to all points in the heart of Roxbury! Litchfield County has a bounty of wonderful outdoor activities including hiking trails, boating, fishing, swimming, wineries, and skiing. A natural food market is less than 15 minutes away and many local farm markets and farm stands. Relax and enjoy the lovely boutiques, antique shops, and dine in farm to table restaurants. Welcome to Litchfield Hills!

Privacy, views and refined elegance merge to create a truly exceptional offering. Set behind a private, gated lane with only one other residence, 11 Raven Rock is one of those Litchfield County estates of which dreams are made. The stately 4BR/5.5BA main home features the highest level of detail. The public rooms boast high ceilings, extensive millwork, expansive windows offering postcard views, and the ability to entertain on the largest of scales while retaining the comfort and intimacy of the glorious country estates found throughout the Litchfield Hills. The spacious bedroom suites - including a main floor primary - feature high ceilings and ensuite baths. Four fireplaces are found throughout the home, including one in the furnished walk-out lower level. A proper country kitchen is adjacent to informal dining and a family room, with a spacious deck overlooking the Steep Rock valley beyond. Connected via a covered walkway, the 3-car garage has a 1BR/1BA caretaker's apartment above. A separate, 2BR/2BA guest cottage expands the ability to create a true family compound. The grounds rival the finest Relais & Chateaux properties: the mature gardens - extensive and beautiful - extend all the way to the glorious and sparkling gunite pool which resides in discreet privacy behind a formal boxwood hedge. Tennis court for enthusiasts. An incomparable setting hidden in Roxbury and only 90 minutes from the city. Note: Main house 5,563SF and Guest house/apt total 1,494SF.

Just 90 minutes to NYC in a great southern Roxbury location, this stylish colonial is privately sited with pool in a beautiful park-like setting. The two story foyer opens to living room and den and then into the great room with floor to ceiling fireplace, kitchen with granite counters, center island and french doors which lead out to the deck and terrace. The expansive deck overlooks pool and mature gardens and plantings throughout the property. Additional amenities such as a Generac generator, fenced vegetable garden, storage shed, stone walkways and long driveway make this the perfect retreat! *Additional Land Available for Sale.

Family compound on 30+/- high acres with long driveway to 7-bedroom, 4 1/2 bathroom contemporary main house with easy indoor/outdoor living. Vaulted living/dining with fireplace & sliders to deck. Eat-in Kitchen. First floor primary bedroom suite with fireplace & sliders to deck. Den with fireplace & sliders. Vaulted family room with fireplace. Game room. 3-car attached garage. Separate 2-bedroom, 1-bathroom guest house, swimming pool, tennis court & pond offering total privacy and long western views. Level lawns. 3 parcels. Must See!

One of early Roxbury's fabulous beauties! This well-preserved, late nineteenth-century Victorian Farmhouse has been lovingly maintained over the years, featuring modern renovations with appreciation and sensitivity to original detail. Huge, bright country kitchen, made for easy entertaining, is the central gathering place. Marble center island open to four directional views of the gardens, stone patio & walls, large blue stone screened porch and in-ground gunite pool. Adjoining, relaxed, yet formal, dining room has original Italianate bay windows and doors. Welcoming front and back parlor rooms feature wrap-around veranda and screened bluestone porch. Three period fireplaces. Three generous sized bedrooms on the second floor; main suite has a large closet room and a two room bath. Three story Country Carpenters Bank Barn with 4+ parking places. Also included, #8 Painter Hill. a four-room cottage, at a distance, planted out and private to main house with its own driveway. An income producing property since 1986. Stunning and private setting. The six acre protected property is adjacent, on two sides, to Roxbury's historic farms. Other two sides border major estates. Features a brook, land dotted with stately old growth Sugar Maples, conifers and open land. Walk to Maple Bank farm stand, Roxbury Market and houses of worship. A very special country estate 90 minutes from NYC. Q

Utterly Private Country Estate. Expansive 4+ bedroom meticulously maintained, classically-designed house set high up a long tree-lined driveway w/distant southern & western/sunset views on 24+ secluded acres of verdant lawn, beautiful perennial gardens, ancient trees and a serene pond. Grand room dimensions, high ceilings, solid wide-board pine floors & windows designed to maximize the stunning views throughout. Formal center hall. Elegant living room w/wood-burning fireplace. Stately dining room. Fabulous great room/kitchen w/vaulted ceiling, large stone fireplace, over-sized windows & access to a mahogany deck & lovely stone patio overlooking the property. NEFF-designed kitchen with top-of-the-line appliances & beautiful custom cabinetry. Heated sunroom w/vaulted ceilings. Den/office w/fireplace & handsome wood accents. 1st floor ensuite bedroom. Upstairs: primary bedroom w/fireplace, timeless-designed marble bathroom w/soaking tub & large shower, 3 walk-in closets & a sweet terrace. 2 more bedrooms share a hall bath. Walk-out lower level currently configured as family room, gym, full bath & laundry but has potential as self-sufficient apartment. Wood-paneled elevator services all floors including the heated 3-car garage. 2-bedroom pool/guest house w/great room w/fireplace, kitchen & lower-level apartment w/fireplace. Heated gunite pool. Poolside fireplace. Custom elevated vegetable gardens. Solely one-family-owned.Offers multi-generational living in a tranquil oasis. Rare.

Mint / Move-in Condition! Pristine hilltop home with views on 3 +/- acres. Gorgeous, chic, mint renovation. Open floor plan kitchen/family room with wood-burning fireplace and french doors to a private flagstone patio. Bright and airy living room and dining room. Primary bedroom with vaulted ceilings, balcony and large ensuite renovated bath. Three more bedrooms, 1 full and 1 half bath. Only a short distance to Maple Bank Farm Stand, Toplands Farm, and historic Roxbury Center. Hot tub possible on rear terrace.

Taking to heart the famous quote "Simplicity is the ultimate sophistication" by Leonardo de Vinci, the current owners designed this brick saltbox to perfection. Much thought went into the high quality new and reclaimed materials used. The exterior is historically correct handmade Waterstruck brick with Lifespan Solid Select pressure treated trim from New Zealand, a 5/8" pressure treated cedar shingle roof and handmade copper lighting. The thick granite rectangular blocks that make up the rear patio came from the exterior of a 19th century prison. Other handmade details include the front entry with antique bullseye glass transom and custom staircase including the balusters. The detached two garages/barns were built by Country Carpenters Post and Beam Buildings and both have split systems. The interior is elegant and charming. The kitchen is highlighted by the handmade Cherry and Butternut wood cabinetry, custom handmade brick wood-fired pizza oven and Bertazonni appliances. The formal living room w/fireplace has gorgeous crown molding which is also found in the comfortable study. The primary bedroom upstairs has a full bath and two walk-in closets. The additional two upper-level bedrooms share a hall bath and the laundry is hidden behind a pocket door. Exactly where needed, the windows in the lower level make the space light and bright. On this floor is the fourth bedroom, full bath, family room and storage rooms. Adjacent to land trust on quiet country road.

This 4-bedroom, 2.5-bath house nestled in a serene location is not just a dream home; it's a lifestyle. Its beautiful views, modern amenities, and comfortable spaces make it the perfect place to create unforgettable memories.

Magically enchanting, nestled, literally, into a private Roxbury hillside, this unique "bermed earth shelter home" of stone, stucco and slate overlooks nearly 8 acres of professionally landscaped grounds, a gunite pool, stone patios, seasonal views and an active year round stream. The approach over the bridge, along a gentle sloping winding driveway opens to a lush, intimate setting of mature grounds graced with an extraordinary, architectural creation that blends the building into the landscape more harmoniously than a conventional home, with the earth providing soundproofing. The architect, Louis O. Roberts, designed a structure less susceptible to the impact of extreme outdoor air temperatures with energy efficient passive solar. Earth-sheltered houses also require less outside maintenance. Additional features include a newer septic system, central air and two stone fireplaces, a lower level, walkout studio space with conversion opportunities for more bedrooms and a bath. This is a rare opportunity to own a property of special provenance in a highly coveted estate area of Roxbury. The price reflects need for skylight replacement.

Mint/Move-in Condition! Meander down the most scenic of Roxbury dirt roads to reach this private colonial with all year heated spa swimming pool on 3.1 +/-acres tucked between the Shepaug River, historic woods, Judd's Bridge and Judd's Bridge Farm and 1000 acres of Steep Rock Land Trust with endless hiking trails. 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 8'x 16' spa 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. Cherished location. Must see!