luxury houses for sale Roxbury, United States

Sited privately on 2.7 scenic acres in Woodbury's desirable Cardinal Hill neighborhood, this classic four-bedroom Colonial offers a perfect blend of quiet country living and everyday functionality. As part of a low-fee, self-managed neighborhood association, residents enjoy a wonderful sense of privacy and peace of mind. The main level features a traditional flow, including a formal living room and a separate dining room ideal for gatherings. Across the back of the home, a comfortable, open living space connects the eat-in kitchen-complete with a center island bar-to a cozy family room centered around a fireplace. This bright living area looks out to serene, elevated treetop views. A spacious pantry, dedicated laundry room, and a half bath complete the well-organized first floor. Upstairs, the primary bedroom suite features a private full bath and a spacious walk-in closet. Three additional bedrooms are nicely proportioned and share a full hallway bath. A traditional home in a peaceful, established setting just a short drive from the vibrant shops, eateries, and historic charm of downtown Woodbury.

Nestled in the picturesque Upper Grassy Hill community of Woodbury, CT, this stunning Colonial residence at 557 Upper Grassy Hill Road offers a harmonious blend of timeless elegance and modern comfort. Boasting 3784 square feet of thoughtfully designed living space, this home welcomes you with a grand two-story foyer adorned with gleaming marble floors. The main level features a formal living and dining room, a private home office, and a sun-drenched kitchen equipped with granite countertops, stainless steel appliances, and a skylight. Flowing seamlessly from the kitchen is the spacious family room with a vaulted ceiling and a cozy pellet stove, leading out to an expansive deck offering privacy and distant views, creating your own outdoor sanctuary. Upstairs, discover three generous bedrooms, including a luxurious primary suite with hardwood floors, trey ceiling, dual walk-in closets, and a beautifully remodeled spa bath. A dressing room/sitting room adds a touch of serenity to this retreat. The fully finished walk-out lower level is an exceptional in-law or au pair suite, featuring hardwood floors, a kitchen area with granite counters, a bedroom with built-ins and a Murphy bed, a spa-like marble bath with a steam shower, and a spacious great room with built-in seating. French doors open to a stunning bluestone patio with a plunge pool/spa, perfect for relaxation or entertainment. Additional highlights include surround sound, a Belgium block-lined driveway, stone walls, irrigation system, and a generator, ensuring convenience and luxury at every turn. Located just 90 minutes from NYC, this home is part of the self-managed Cardinal Hill HOA ($100/year) and backs up to designated open space for added privacy and tranquility. This property transcends beyond a mere residence; it offers a lifestyle of comfort, sophistication, and relaxation. Please note the interior and exterior security cameras for 24/7 monitoring. Welcome to Upper Grassy Hill Living

Lovely hilltop location in Heritage Village! This Sherman shows like a model home, offering a comfortable, functional layout with no stairs. Set in a wonderful private setting with beautifully maintained grounds, just minutes from the pool and pickleball courts. The open-concept living and dining areas feature a newer wood-burning fireplace, crown molding and wainscoting, and sliders to a private enlarged patio with a motorized awning and peaceful views. The eat-in kitchen includes quartz countertops, glass tile backsplash, stainless steel appliances, and breakfast bar plus dining area. Additional recent improvements include all new flooring in 2025, a new water heater in 2025, and updated custom light fixtures in the living room, dining area, kitchen, and primary bedroom. The primary suite offers a redesigned bath with double sinks, Carrera marble vanity top, walk-in closet, ceiling fan, and sliders to the patio. The guest bedroom provides added flexibility with a newly installed built-in Murphy bed, making it ideal as a bedroom, home office, or exercise room. Plenty of guest parking. Heritage Village offers an exceptional array of clubs and activities, along with convenient access to Southbury shopping, dining, medical providers, and major commuting routes. Nearby golf options include Silo Point Country Club, Gainfield Farms, and Pomperaug Golf Course.

Beautifully appointed and tastefully updated, this desirable 2-bedroom New Englander townhouse enjoys a prime Heritage Village location surrounded by lush landscaping and just a few flat steps from your garage bay. The inviting main level features new luxury vinyl plank flooring, an updated white kitchen with granite countertops, tiled backsplash, and ample cabinetry, along with a spacious living and dining room highlighted by a stylish yet cozy propane fireplace and a sliding glass door leading to a private deck overlooking beautifully landscaped grounds. The upper level offers two generously sized bedrooms with ceiling fans and newer carpeting, including a spacious primary bedroom with two closets and a private balcony. The recently renovated full bath showcases stylish finishes, while the second bedroom provides flexible space for guests, a home office, or den. A conveniently located full-size washer and dryer complete the second floor. Experience the exceptional lifestyle Heritage Village is known for. Set on 1,000 picturesque acres, this premier active adult community offers maintenance-free living with outstanding amenities, including four swimming pools, tennis and pickleball courts, fitness and recreational facilities, art studios, numerous clubs, and an extensive calendar of social activities.

Rarely available. 1880 antique gem on 10 acres, with a first level primary bedroom and bath, situated on one of Bridgewater's most prestigious and quiet roads, offering a private setting. This residence masterfully blends historic character with an airy, open floor plan where the kitchen flows seamlessly into a spacious great room and a formal living room anchored by a classic fireplace. The interior living space consists of a main floor primary bedroom and bath, second level with 2 bedrooms and shared bath and a third level bedroom with it's own bath. The spaces transition beautifully to a 24 x 18 screened porch with slate flooring, opening onto a bluestone terrace. Perfect for entertaining, the terrace overlooks the pool and captures western exposures. The property is further enhanced by a two-story barn, providing ample space for storage or workshop. This is a unique opportunity to own a quintessential New England retreat in a premier location.

Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep. While honoring its historic character, the home has also benefited from over $300,000 in thoughtful improvements that enhance comfort and preservation without compromising authenticity. Notable upgrades include the installation of central air conditioning for modern year-round comfort and elegant copper gutters that complement the home's historic architecture while providing lasting durability. These investments ensure the property is as functional as it is beautiful, blending 18th-century craftsmanship with the conveniences expected today. Beyond the historical significance, this home offers genuine livability with four full bathrooms, one half bath, and spacious rooms designed for both elegant entertaining and comfortable everyday living. The residential zoning ensures a peaceful setting that honors the home's timeless nature. The location is equally enchanting. Situated near Hollow Park in Woodbury - a town Reader's Digest once described as simply charming - you'll enjoy walkable access to local restaurants, unique shops, and the vibrant heart of this beloved New England community. Opportunities to own a property of this caliber, significance, and authenticity come along once in a lifetime. Don't let this extraordinary piece of American history pass you by. Schedule your private showing today.

Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request. The exterior is as enchanting as the interior, offering a large heritage red brick patio that provides the perfect vantage point to overlook the acreage, which gently slopes down to a babbling brook at the property's edge. The outbuilding includes a charming potter's shed equipped with electricity, ideal for gardening, while the barn with original hand-hewn beams, lower-level stalls, and running water is ready for equestrian use or a premier hobby space. Bacon Pond House isn't just a home; it's a piece of history, updated for the way you live today. A 90-minute drive from the bustle of NYC, this property is moments away from the quaint shops, parks, and eateries of historic Woodbury.

Welcome to this magnificent Custom Contemporary in a beautiful Brookfield location. A long, private circular drive leads to this stunningly landscaped 3/4 bedroom, 3.5-bath home with a 2-car garage. Welcome into the breathtaking open floor plan featuring vaulted ceilings, skylights, gleaming hardwood floors, and sun-drenched rooms. Perfect for entertaining, the living room boasts a cathedral ceiling and a double-sided fireplace with a marble hearth and mantle, opening to a formal dining room with elegant grasscloth wallpaper. The family room shares the double-sided fireplace with a brick face and French doors lead to a sprawling composite deck overlooking the private wooded backyard.The ultimate gourmet eat-in kitchen includes a center island with a wine rack, breakfast bar, stainless appliances, custom mirror finishes and a sophisticated casual dining area. The main level also hosts a quiet office with built-ins, a designer powder room with gold tone accents, a large laundry room, and a luxury primary suite complete with a walk-in closet, updated full bath enhanced with luxurious walls. Upstairs, a balcony overlooks the main level, leading to two generous guest bedrooms and an updated full bath. The finished, walk-out lower level offers excellent in-law potential, featuring a large living and dining area, a separate den (used as a 4th bedroom), a full bath, and sliders to a private patio. Central AC, efficient oil heat, full alarm system, and a Generac Generator.

Escape to the beauty of Bridgewater, Connecticut! This completely renovated home on 2+ acres will welcome you. A stunning home from one room to the next with open space and perfect updates. The kitchen is a true show stopper. The abundant soft close cabinetry, stainless steel appliances, the granite countertop, and island create a great entertaining space framed perfectly with rich dark beams. Move to the dining room -there are walls of windows, moldings, and hardwood floors. A center staircase wraps to the living room, where a fireplace with a striking mantle centers the room. Step out to a screened-in porch surrounded by nature- a quiet brook and privacy set the mood. 4 bedrooms on the upper level, bright and spacious, hardwood, and plenty of closet space. A fully updated bath with detailed tiling is just lovely. The spacious finished attic has natural light, hardwood floors, and can be used for play space, extra beds, or an office. This special property offers a new professionally landscaped yard with a 2-car detached garage easily reached from the covered deck. Large basement with utility sink and newer mechanicals, dual AC/ heat electric system, oil furnace was replaced in January 2026, and additional storage and walkout. A favored escape spot for many, Bridgewater is unique. This home will not disappoint. Just open the door and discover for yourself how great it is to be home. Located just minutes from both Bridgewater's village center and the town of New Milford.

For those who enjoy entertaining and privacy, this 4.3-acre waterfront estate on the shores of Lake Lillinonah is an idyllic retreat. The land directly across from the property is protected open space, ensuring no future development. A private dock and remote-controlled boat lift provide direct lake access, while a hot tub, sauna, fire pit, screened porch, and multi-tiered deck offer a variety of inviting outdoor settings. The 5,400-square-foot residence makes an immediate impression with a two-story foyer and a main level that balances openness with well-defined, functional spaces. The dining room, butler's pantry, and expansive family room connect seamlessly, while a formal living room, private office, and oversized kitchen complete the layout. Upstairs, four bedrooms include a standout primary suite with two walk-in closets, a sitting room, full bath, private deck, and oversized windows overlooking the lake. An additional great room offers flexibility as a fifth bedroom, media room, or playroom. The finished walk-out lower level is designed to serve as its own destination, featuring a spacious game room, large bar area with sink, full bath, flexible bedroom or office, and abundant storage. Direct access to the backyard creates an effortless indoor-outdoor lifestyle. Lake Lillinonah offers the best of both worlds: a relaxed, vacation-inspired lake lifestyle set against a backdrop of large, private parcels and peaceful natural views. *Property is served by a four-bedroom septic system; however, the home functions as a five-plus-bedroom residence.

Nestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a fluid layout designed for effortless living: a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with a fireplace, a private home office, and a convenient full bath. Upstairs, you'll find five sizable bedrooms, including a primary suite complete with two walk-in closets and a private full bath. The remaining four bedrooms share a large full bathroom equipped with a double vanity. The expansive walk-out lower level adds incredible value with over 1,000 square feet of finished, heated living space. Create a game room with the provided pool table and a den area with a second fireplace, or utilize it as a potential in-law suite as light streams through a large picture window with views of the backyard. Outside, a stately circular driveway frames the property amidst mature, private landscaping, while the back deck is primed for summer grilling. Complete with an oversized two-car garage featuring a dedicated work area and abundant storage closets, this home is ready for you to bring your design ideas and unlock its full potential! Walking distance to Trolley Bed Preserve and Whittemore Sanctuary is nearby as well as all the shops, cafe's and restaurants of Woodbury.

Nestled on a private, beautifully landscaped lot in the Barkwood Falls community, this charming four-bedroom, two full and one-half bath Colonial offers the perfect blend of comfort, style, and lake community living. The inviting main level features a spacious eat-in kitchen with granite countertops and tile flooring, a formal dining room, a cozy family room with a fireplace, and a sun-filled sunroom with pellet stove and vaulted ceilings that brings the outdoors in. Upstairs, you'll find a spacious primary suite along with three additional bedrooms, providing plenty of room for family and guests. Outside, the grounds have been lovingly cultivated using many native species, creating a spectacular perennial display of color and texture throughout the seasons. Just steps from your door, enjoy Barkwood Falls' private sandy beach, picnic area, playground, and boat launch. Dock slips are available by waitlist for just $25 per foot, while kayak or canoe storage is only $175 per space annually. The low annual association dues of just $200 makes it easy to enjoy all the amenities this wonderful lake community has to offer. Conveniently located close to shopping, downtown, and major highways, this exceptional home offers the perfect balance of privacy, convenience, and year-round recreation.

Set at the end of a shared private driveway on 2.9 wooded acres, this 5BR home presents a unique opportunity for those seeking privacy, space, and the chance to create something truly their own. Surrounded by natural beauty, the property offers room to explore, garden, entertain, or simply enjoy a peaceful setting while remaining close to everyday conveniences. A covered porch welcomes you inside where hardwood flooring runs through much of the home. The living room features built in bookshelves, a wood stove, and large windows that bring in natural light. A notable advantage of the home's layout is the presence of three bedrooms on the main level, offering flexibility for single level living, guests, home office space, or multigenerational needs. The main level also includes an eat in kitchen with a large pantry, dining room, full bath, and a four season room overlooking the wooded surroundings. Upstairs are two additional bedrooms and a half bath with space that may accommodate future expansion to a full bath or laundry area. Ample closet space is found throughout. The unfinished lower level provides additional flexibility with workshop space, laundry and mechanical areas, a storage room suitable for a wine or root cellar, and a two car tandem garage. Outside, you'll find an inground pool with a new liner (2024), multiple outbuildings and wood sheds (conveyed as is), and abundant parking. Recent improvements include a new roof (2023), furnace (2023), well equipment (2023), gutters (2024). For added peace of mind, the home is equipped with a whole house Generac generator. Offering a rare combination of privacy, character, and potential, this Southbury property is ready for its next owner to bring their vision and personal touches. Conveniently located just minutes from Exit 15, shopping, restaurants, Main Street, nearby lakes, and the movie theater.

Nestled on 2 peaceful acres in Newtown, CT, 23 Old Green Road presents a beautifully maintained 4-bedroom, 2.5-bath Colonial retreat that exudes privacy and sophistication. Step inside this inviting residence to discover a remodeled kitchen boasting stainless steel appliances, marble countertops, and a butcher block island. French doors lead you from the kitchen to the expansive rear deck with built-in seating, offering the perfect setting for outdoor gatherings. The main level also features a cozy family room with a wood fireplace, a dining room with a bay window, a versatile living room or den with custom built-ins, and a convenient laundry/powder room with designer finishes. Make your way upstairs to find the primary suite, complete with a wood-burning fireplace, barn doors, custom closets, and an updated bath featuring elegant marble finishes and a rain shower. Three additional bedrooms provide flexible space for guests, a home office, or daily living needs. The property also includes a walk-up attic and a full basement with interior and garage access, offering ample space for hobbies, a workshop, a home gym, or storage. This Colonial gem has undergone major upgrades, including Central A/C installation in 2026, a high-efficiency System 2000 boiler added in 2025, rebuilt chimney with new flue liners, additional attic and basement insulation, upgraded electrical system, and a professionally painted exterior with a warranty. Additional highlights of this residence include recessed lighting, dimmers, fresh paint, upgraded closets, an epoxy garage floor, a security system, rebuilt front steps, new porch columns, beautifully landscaped grounds, a paver walkway, gravel patio, and fenced garden - all contributing to a welcoming outdoor space for relaxation and entertainment.