Roxbury CT Real Estate & Homes for Sale

Welcome to this one-of-a-kind, 3-bedroom, 2-bathroom chalet, nestled on a picturesque 4-acre property in the serene countryside of Roxbury. This unique home, adorned with the artistic touches of its previous owner-an accomplished artist- has blend of rustic charm and creative flair. As you approach the house, you'll be captivated by its distinctive chalet-style architecture, surrounded by lightly wooded areas and beautifully landscaped gardens. A tranquil pond adds to the natural beauty of the setting, making it a perfect retreat for nature lovers. Inside, the home is impeccably maintained, having been cherished by the same family for over 55 years. While it has a comfortable living space, it awaits your personal touch for updates. Recent improvements include a brand-new roof installed in the spring of 2024, ensuring peace of mind for years to come. The property features two outbuildings: one for equipment storage and property maintenance, and another equipped for woodworking and artistic pursuits. Please note the outbuildings are locked for safety reasons, but serious buyers will be allowed access. Located in a rural area favored by celebrities and New York residents, this home is surrounded by farms, horses, and the tranquility of country living. This estate is sold as-is, presenting a wonderful opportunity to create your dream home in a stunning location. Don't miss the chance to own a piece of Roxbury

Pristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by Roxbury's best historic estate neighborhood, farms and homes of artists, actors and writers. Magnificent open floor plan with 2-3 bedrooms, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch. Dine or relax on the flagstone terrace next to the heated gunite pool. Mature gardens with climbing roses, lavender and blue hydrangea.

FoxCroft exudes simple elegance. She stands proudly mid block on South Street, the center of town where children bounce house to house trick or treating. Tucked on this quiet street lined with giant gracious old Maples, Oaks and stone walls. It appears time has stood still in Roxbury, in the very best way. The property is rare in that it seemingly has space for everything. A heated pool, studio, large three car garage, guest house and pond. Also giving clues to its past: an ice and well house. This house is short on nothing. Most of all, charm. This 1792 Colonial Farmhouse has certainly stood the test of time, and oh, the stories it would tell. Enter into the living room flanked by two massive fireplaces, lit up by a grand window. It's easy to imagine spending holidays with the fireplaces blazing. The dining room provides a moody space to enjoy dinner in front of yet another intimate fireplace, hewn beams accent the ceiling. The sunroom provides a space to read a book on a Fall afternoon surrounded by windows filled with the changing colors of the season. Built in bookshelves stand at the edge of the space for decor and beloved trinkets. The chic and updated kitchen provides modern amenities including a six burner Viking stove and a SubZero refrigerator. Connected to the kitchen is a pantry with ample storage and a place to tuck away kitchen goods. A front and back staircase connect you to the second level. Upstairs has three ensuite bedrooms.

Meander over a small bridge and through tall pines to reach this distinctive 4 bedroom home on 6 very private acres. A gracious wood paneled central foyer directs you into the living room, dining room, or through to a thoughtfully designed great room. The kitchen features a wrap-around island with bar stools, high-end appliances walk-in pantry/laundry. It also opens to the breakfast nook and sitting areas with stunning stone fireplace and large windows. French doors open to a blue stone terrace with newly installed outdoor kitchen and pizza oven. The new Gunite heated pool has automatic cover and plentiful blue stone terracing for relaxing. Enjoy the built-in Jacuzzi which seats 6 comfortably. The main floor is completed by the spacious primary bedroom, huge walk in closet, office nook and luxury bath. Upstairs are 2 ensuite bedrooms. The large finished lower level is walk out. It has been expanded to include; media/game room, bedroom/bath, gym, and storage rooms. Impressive high ceilings, the finest stone and woodwork, and exacting attention to detail. There is a full staircase in the garage which leads to an unfinished space which might make an excellent in-law apt or studio.

Quintessential CT Mini- Estate. Top restoration of 3-Bedroom/2.5 bath Victorian Cottage with Large Pool/Guest House, stunning pool, 2nd small spa pool and wonderful stone terraces and open lawns. Historic Pool House Rental Income: $50,000-$100,000 per year. Perfect for generational living as both the Main House and the Pool House have their own pools, driveways and garages. Main house with large wood burning fireplace and original antique wood floors throughout. Newly Expanded Vaulted, Open and Airy Pool House with chef's kitchen, bedroom, full bath, finished lower level offering a second full bath and more living space. Charming, covered BBQ Deck overlooking pool and 2-car garage below. Best scenic road for walking or bike riding by historic farms and homes owned by numerous artists, authors, actors and other private luminaries. Mature plantings include beautiful hedges, blue hydrangea, specimen trees -- enough flowers to keep vases full. Barn. Special. Must see!

White Tail Farm, located in Roxbury, CT, just 90 miles from Manhattan, is an 86-acre estate offering the best of New England living. Centered around a restored c.1790s farmhouse, the property was substantially renovated and expanded in 2003, resulting in a spacious residence that artfully combines historical elements with modern amenities--ideal for discerning individuals seeking a private sanctuary or a multi-generational compound. The 5,600 sqft main residence features oak flooring, beamed ceilings, and six fireplaces. The open-concept kitchen and family room are equipped with high-end appliances from SubZero, Wolf, Miele, and Viking. The upper level has two primary suites with en-suite baths and walk-in closets, plus two additional bedrooms and a guest room. The lower level comprises a Great Room for recreation. Outdoor amenities include a heated gunite pool, tennis court, sports court, and a 4-acre meadow with surrounding woods which are perfect for hiking and snowshoeing. The 1,890 sq. ft. guest house provides a spacious flexible living space with two fireplaces, a recreation room, bedroom, full bath, and a kitchenette. The estate's 86 acres include a spring-fed pond, Battle Swamp Brook, curated landscaping by Robin Key, and walking trails. Additional features include a 3-car garage, a 4-stall barn, solar panels, and recent upgrades like a new well pump, cedar roof, garage doors, and smart home technology.

Quintessential Roxbury Cape with detached studio space on a quiet road across from 300+ acres of Roxbury Land Trust and hiking. Enjoy modern amenities and unparalleled privacy in this serene setting with abundant windows and French doors that fill the space with natural light. Step inside to an open floor plan through an entry featuring custom built-ins and stone flooring, leading to a living room and dining area with intricate paneling. The updated kitchen, with breakfast bar, offers stunning views of the preserve, stone walls, and access to a large deck perfect for outdoor entertaining. The main floor primary suite includes a marble bath with dual vanity and opens to a flexible space-ideal as an office, den, dressing room, or additional guest space. Upstairs, find two bedrooms and a spacious bath with a window overlooking the grounds. The larger bedroom features vaulted ceilings and a large walk-in closet, offering potential for an alternative primary suite. The walk-out lower level adds living space and storage, while the heated and cooled studio above the garage is perfect for a home office, artist's studio, or potential guest retreat. Outside, manicured grounds boast local granite hardscaping, including a stone patio and sculptural steps leading to the studio. Ideally located with hiking trails out your door and proximity to Washington Depot, Woodbury, and New Milford! Agent/owner.

Modern Farmhouse Oasis on 4 Acres in Peaceful Roxbury. A winding drive leads you to the home, where elegant stone steps guide you to a covered porch, surrounded by a lush perennial garden. Inside, the sophisticated living room features French doors, grasscloth wall-covering, and crown molding. This seamlessly connects to a formal dining room with tray ceiling and a bay window. The heart of the home is the recently refreshed eat-in kitchen, equipped with modern appliances, bar seating for four, a large pantry, access to a large deck and a custom-built office nook ideal for multitasking. The great room offers comfort and style, centered around a large wood-burning fireplace with an ornate mantle that complements the home's beautiful millwork. Custom built-in cabinetry with inset lighting and a recessed ceiling enhance the charm of this space. Upstairs, the primary suite is a private retreat, complete with a walk-in closet and an oversized bath featuring a jetted tub and walk-in shower. The upper level also includes a linen closet, shared bath with dual vanities + bathtub, and 3 generous guest bedrooms, each with its own closet. The lower level provides access to a 3-bay garage and a large workshop with exterior access and ample natural light-perfect for a workshop or potential additional living space. Meticulously maintained; new roof, exterior paint, AC + Furnace in past 3 yrs. Ideally located, you are mins to Woodbury, Southbury and all Litchfield County has to offer!

Discover this recently renovated single-family home nestled on 3.2 wooded acres in picturesque Roxbury, CT. Featuring 4 bedrooms, and 2 complete bathrooms. Primary bedroom provides a spacious walk in closet recently renovated bathroom with modern finishes and an electric fire place. Enjoy serene views from the private balcony making this suite the perfect blend of comfort and sophistication. Potential in-law with 2 additional bedrooms. This home blends modern amenities with rustic charm. Enjoy the tranquility of the expansive, wooded yard. Schedule a viewing today!

WELCOME TO YOUR DREAM HOME! This stunning new construction colonial farmhouse boasts modern elegance and top-of-the-line finishes throughout. Featuring 5 spacious bedrooms and 3.5 luxurious bathrooms, this home offers ample space for comfortable living. The open concept living area is perfect for entertaining, with a gourmet kitchen that includes high-end stainless-steel appliances, custom kitchen cabinets, marble countertops, and a large island. Enjoy the natural light that floods through the large windows, highlighting the beautiful hardwood floors. The Owner's suite is a true retreat, complete with a spa-like ensuite bathroom and walk-in-closet. Step outside to a beautifully landscaped yard, perfect for outdoor gatherings. Don't miss the opportunity to make this exquisite home yours!Additional Features:- Black Windows (Exterior)- 5" Wide Hardwood Flooring- Decorative Wood Beams- Mahogany Front Door- 5 Panel Interoir Doors- Modern Door Hardware- 5-1/2" Modern Baseboard- 3-1/2" Modern Casing- Shiplap Trim- Waterfall Kitchen Island- Marble Slab Backsplash- Farmhouse Kitchen Sink- Matte Black Plumbing Fixtures- Modern Electrical Fixtures- Smart Home Automation- Beadboard Porch Ceiling- Historic Stone Walls- Nearly Level Back Yard- Modern Gas Fireplace- Architectural Roof Shingles- Fiber Cement Plank Lap Siding- Fiber Cement Panel Siding (B&B)- PVC Trim & SoffitsOptional Features:- Inground Swimming Pool- Barn- Shed- Metal Roofing Above Porch

A beautiful stone house in Roxbury. The large vaulted living room is spectacular. Its multiple windows make it very sunny, the coffered ceiling and the custom design fireplace create major drama. It continues in the octogonal library with its built-in bookshelves. The formal dining room and the den continues to enhance the feeling of space. The open gourmet kitchen has radiant heat and granite countertops. Its French doors open into the landscaped backyard. The house has four bedrooms and three and half baths.The primary has a large walk-in closet and en suite bathroom, with a lovely view. A guest room is incredibly romantic located in the tower. There is Central a/c and a 2 car garage. Conveniently a separate entrance is for either an office or a potential in-law apartment with its own full bath. The grounds are beautiful, professionally lansdcaped with specimen trees and a large pool. It extend on 3 acres. Come and see it!

A long driveway winds you into this idyllic retreat with western views and sunsets, nestled minutes from town. This stunning Cape Cod Farmhouse is in process two additional bedrooms being added in the Main House, along with a 2 bedroom guest house was thoughtfully constructed in 2020. Owner is in process of completing two additional bedrooms and a full bath on the upper level. It is a harmonious blend of modern comfort and classic charm. The open floor plan invites effortless flow, while French doors beckon you to the expansive deck where western sunsets paint the sky. Inside, discover the allure of a gourmet kitchen with central island, perfect for culinary adventures and casual gatherings. The home allows the for more expansion. The walk-out lower level, boasting high ceilings, gives further opportunity to customize living space. Beyond the main house, a charming two-bedroom guest house adds versatility and privacy. Immerse yourself in nature's beauty as you explore nearby Hurlbut Park and hiking trails, all just minutes away. The oversized two-car garage completes this exceptional property, providing ample space for your vehicles and storage. Enjoy open-concept living that seamlessly flows to a grand deck, where you can unwind while taking in breathtaking western sunsets over the neighboring horse paddock.

Step into a world of charm and timeless elegance in Roxbury, CT. This bucolic estate spans 5.18 acres and offers a blend of historic charm and rustic sophistication. Explore the six-bedroom main house, complete with five bathrooms and five fireplaces, wood beams and stunning wide plank flooring bring warmth and style. This tranquil home embodies classic Connecticut living with its antique patina and captivating features. The estate also includes a charming two-bedroom guest cottage, perfect for hosting guests or extended family in a romantic setting. Invest in a lifestyle that blends history, luxury, and country living. Your dream home awaits.

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.

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".

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.

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.

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!