luxury houses for sale Southbury, United States

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

Nestled in Bear Run Estates of Woodbury, CT, lies a stunning 4-bedroom, 2.5-bath Colonial home at 54 Bear Run. Proudly maintained by its original owners, this residence exudes charm and elegance. A high-efficiency propane furnace, central A/C, and whole-house Generac generator ensure modern comfort and convenience. Step inside to a welcoming 2-story foyer leading to a gourmet eat-in kitchen with granite countertops, stainless steel appliances, and a breakfast bar. The open floor plan seamlessly flows into the cozy family room with a propane fireplace, perfect for relaxing evenings. A private office, formal dining room, living room, and powder room with laundry complete the main level, all adorned with beautiful hardwood floors. Upstairs, the primary bedroom suite boasts exposed beams, a walk-in closet, and a luxurious bath with a soaking tub, tiled shower, and heated floors. Three additional spacious bedrooms share a full bath. The walk-out lower level offers flexible finished space for recreation or relaxation, with potential for expansion. Outside, the professionally landscaped grounds feature a storage shed and a maintenance-free Trex deck, ideal for outdoor entertaining.

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.

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.

Timeless Elegance in the Heart of the Historic District . Step back in time without sacrificing modern convenience in this enchanting 1750s colonial, perfectly situated on a premier corner lot within the town's coveted Historic District. This home isn't just a place to live; it's a piece of local history loaded with old world character. From the moment you step inside, the rich wide plank hardwood floors and period details whisper stories of the past. The layout seamlessly blends cozy historic proportions with functional spaces designed for today's lifestyle. The kitchen features new cabinetry and appliances with adjoining stone floored sun room. Bright and airy rooms featuring original architectural charm. 2 well-appointed bedrooms offer peaceful retreats with a 3rd suitable as a nursery or office space. 1.5 baths include a convenient main-floor powder room. An expansive utility and mudroom provides ample storage and organizational space-a rare find in a home of this vintage. A lovely level corner lot is the perfect setting for this in town charmer. New 1250 gallon septic tank 2025. 24 hour notice for all showings please.

Tucked away in one of Roxbury's most desirable neighborhoods, this 4-bedroom, 2.5-bath Colonial sits at the end of a quiet dead-end road, offering exceptional privacy and a peaceful setting, with the Natalie White Preserve just down the road. This beautifully updated Post & Beam home blends timeless craftsmanship with modern amenities, featuring warm architectural details, exposed white oak beams, and a dramatic living room with soaring 27-foot ceilings, along with thoughtfully designed living spaces. The flexible layout includes a private in-law or studio space, ideal for guests, extended family, or a home office. Set on a serene, wooded 3-acre lot with mature landscaping, the property provides a tranquil retreat perfect for relaxing or entertaining. Despite its secluded feel, it's a short 15 minutes drive from fine-dining, shopping, and easy access to I-84, and ideally located just over 90 minutes to NYC and approximately 2 hours 20 minutes to Boston, offering both convenience and comfort in a truly special location.

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.

Broadview Estate - A masterpiece in colonial revival design -Perched gracefully on the gentle hilltops of Middlebury! The Cameron Clark design is well preserved and displays a high quality of workmanship and materials, as well as the gracious proportions and classically inspired details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the house and related garden cottages, grounds and surrounding landscapes of fields and woodlands, drape across the gentle hilltops of Middlebury with magnificent vistas east, west and north. It constitutes one of the most beautiful and historically significant properties in the area. The estate encompasses the seventeen room main house and three guest cottages: converted stables with unique industrial accents, classic cape, and pool side studio. The main home features magnificently scaled formal and informal settings, exquisite millwork, hardwood floors. Chefs' quality kitchen with sensational marble, large butler's pantry, breakfast nook, informal dining room, 800 bottle temperature controlled wine room complete this area. This opens to the library and raised paneled great room with vaulted ceilings and stone fireplace. Pass by the sweeping free-standing staircase which leads to the second level and enter the formal dining room and living room both with fireplaces adjacent to a mahogany paneled office. The wonderful conservatory overlooking the beautiful gardens, sauna room, two half baths

Looking to escape the hectic pace of city life? Welcome to this peaceful, beautifully renovated 4-bedroom home, originally built in 2005, offering the perfect blend of comfort and tranquility. Featuring 2.5 baths and a spacious open-concept living and dining area, this home is ideal for hosting gatherings and entertaining with ease. The modern kitchen is a dream for any home chef, complete with state-of-the-art appliances, ample counter space, and generous storage. Enjoy stunning outdoor views from every angle and make the most of the inviting outdoor space. Perfect for alfresco dining or simply relaxing in nature. A 3-car garage provides plenty of room for parking, storage, and hobbies. This home offers a wonderful setting to grow and thrive, whether you're raising a family or settling into a peaceful lifestyle. Located in Roxbury, a quiet rural town rich in New England charm, you'll enjoy scenic countryside, historic sites, hiking at Mill Hill Preserve, and local artisanal goods at the Roxbury Market. A true retreat with timeless appeal.

Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen. Upstairs, you'll find four spacious bedrooms and two full bathrooms. A bright slate floored sunroom overlooks the inviting heated salt pool, perfect for relaxation and entertaining. Adding to its unique appeal is an attached 1-bedroom in law/guest house with propane heating and cooling, providing flexible space for visitors or extended family. The property boasts level land and lush grounds, including a expansive pasture area, all set against the picturesque backdrop of Pierce Brook. This Roxbury gem combines tranquility with convenience, making it an ideal retreat.

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.

Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manicured acres with a resortlevel pool, just far enough from the city to exhale, yet close enough to make spontaneous weekend getaways a reality. From the moment you arrive, this summer ready property feels like a private club: stone walls, curated landscaping, quiet woods, and outdoor spaces designed for long summer days and late night gatherings. The gunite pool is the centerpiece - sparkling, secluded, and ready the moment you are. Inside, sunlight pours through picture windows into an open layout built for effortless entertaining. Custom oak details, a dramatic fieldstone fireplace, and a chef's kitchen with high-end appliances and stone counters set the stage for everything from cozy winter weekends to lively holiday hosting. With 4 ensuite bedrooms, the home adapts beautifully to guests and long family weekends. The first floor ensuite offers effortless hospitality, while the second floor luxury primary suite- complete with 11 foot ceilings and a marble spa bath - provides a calm, spa-level retreat. A steel-and-glass office alcove and a bonus room above the garage with interior access, offer the perfect flex space for a studio, gym, or potential guest suite. The finished lower level and walkout access adds even more room to unwind. Fully renovated since 2021 including new HVAC, generator, and more - means no projects, no delays to start enjoying the Litchfield Lifestyle.

Escape to the tranquility of this authentic four-bedroom, one-and-a-half-bath log home nestled in the peaceful surroundings of Oxford, Connecticut. Brimming with rustic charm and timeless character, this inviting home offers the perfect blend of comfort and nature. Warm wood interiors and a cozy wood stove create an atmosphere that is both relaxing and welcoming. Enjoy peaceful mornings on the covered front porch complete with a charming swing, or unwind in total privacy on the covered back porch surrounded by serene natural beauty. Every detail of this rustic retreat offers comfort, peace, and the feeling of true country living. Just minutes from Lake Zoar Town Park, offering access to a boat launch, beach, and scenic hiking trails. Whether you're searching for a full-time residence or a private getaway, this log home provides a rare opportunity to enjoy a peaceful and serene lifestyle. Conveniently located near Interstate 84 and Route 8 and approximately 90 minutes from New York City.

Privately set within an enclave of newer luxury homes on a serene cul-de-sac, this exceptional residence offers a refined blend of architectural elegance and modern comfort. A striking contemporary entry welcomes you into a grand two-story foyer, where designer lighting and natural light create an unforgettable first impression. Wide-plank white oak flooring flows seamlessly throughout the main living spaces, enhancing the home's open and sophisticated layout. The chef's kitchen is a true centerpiece, featuring a statement quartz waterfall island, custom lighting, and a curated selection of premium appliances, including a Viking 8-burner double oven range, Bosch suite, coffee station, and Sub-Zero refrigerator. A walk-in pantry with wine storage adds both style and functionality. Walls of glass invite abundant light while framing the home's beautifully designed outdoor living spaces, including an expansive Trex deck and a private patio surrounded by mature landscaping. The primary suite offers a tranquil retreat with dual walk-in closets and a spa-inspired bath designed for relaxation, complete with a soaking tub, walk-in shower, and illuminated mirrors with defogging features. Additional highlights include a private guest suite, Jack and and Jill bedrooms, smart home integration, and a sprinkler system-every detail thoughtfully curated through a bespoke collaboration between the seller and builder. The pool shown is a virtual concept to illustrate potential.

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.

This home is sold WITH the adjacent Building Lot #65 Parmalee Hill Road. TOTAL of 4.09 ACRES. #65 Parmalee Hill Rd is a R-2 Zoned lot (2.04) with shed/barn on property. Beautifully appointed Colonial Style home, built in 2006, with breathtaking views of the surrounding valley. Located in a residential, semi-rural section of Newtown, with easy access to major routes. Throughout the home, you will find hardwood floors, high ceilings, high-end finishes, and tons of windows with an abundance of natural light. Three levels of living, offering 8,530 Square Feet. Majestic in its presentation, this Home features a two-story foyer, a formal living room with fireplace and sconces. The Formal Dining Room offers French Doors, tray ceiling, and mahogany inlay on floor. The large and spacious Eat-In-Kitchen features a gourmet Viking Gas Stove/Range, 2 sinks, large center island/breakfast bar, walk-in pantry. The Two-Story Family Room features a stone fireplace, floor-to-ceiling windows, and hardwood flooring. The Main Floor Bedroom/Home Office, with a Full Bath adjacent. The Upper Level features the Primary Bedroom Suite, plus 3 additional bedrooms and dedicated Laundry Room (hookups only). The Primary Bedroom Suite features a tray ceiling, a large walk-in closet/dressing room, along with a secondary walk-in closet. The Primary Bath features two vanities, a jacuzzi tub, and spacious stall shower. Additional Bedroom w/Full Bath. The two other Bedrooms share a Jack and Jill bathroom

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.

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.

At the end of a long, winding private driveway, this exceptional Roxbury estate offers total seclusion & tranquility-surrounded entirely by protected land trust. Just 2 miles from Roxbury Center and a scenic 2-hr drive from NYC, this rare property is the perfect country escape or full-time residence. The main home is in impeccable, move-in condition, featuring dramatic vaulted ceilings in both the living room and kitchen. A striking floor-to-ceiling flagstone fireplace with a wood stove insert anchors the living room, while a cozy wood-burning fireplace warms the kitchen, creating a welcoming and timeless atmosphere. The chef's kitchen is outfitted w/ granite countertops & top-of-the-line stainless steel Viking appliances, opening seamlessly to a spacious stone patio ideal for entertaining. Luxury continues outdoors with a stunning in-ground pool surrounded by custom stonework, a charming gazebo, and a separate hot tub nestled in nature. A nearby fire pit invites cozy evenings under the stars. Just off the living room, a wet bar adds ease & sophistication to indoor gatherings. Add'l features include a large separate loft apt perfect for guests or remote work, a two-car garage, a second shed/1-car garage w/ electricity, and a full-house generator for year-round comfort. A driveway annunciator ensures privacy and peace of mind. Enjoy nearby shopping and dining in Washington & Woodbury while returning home to your private, resort-like sanctuary in the heart of Litchfield County.

A lifetime of memories have been made in this 4 bedroom/1 bathroom home picturesquely set on 1.45 professionally landscaped acres with an inground pool ready for swimming. The entire property has been well taken care of, and is ready for the next owner to make it their own. The living room is open to the dining room, with glass doors to the deck with an awning for summer days. There's a kitchen and 3 bedrooms to complete the main floor, and 1 bedroom and a family room in the lower level. Perennial gardens adorn the front and back yards, while mature trees compliment the rest of it. Watertown lies in Southern Litchfield County, home of Taft School, Hawk Ridge Winery, 2 golf course, and more! Property being sold in as is condition.

Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene landscapes. The idyllic surroundings include a tranquil stream which meanders down through the property, while established mature plantings burst with color and life, providing a private oasis for relaxation and enjoyment. Imagine alfresco dining on the inviting stone terrace, or pursuing your gardening passions in the dedicated garden shed. This home is ready for its next chapter, offering a foundation of classic Cape Cod charm awaiting modern touches. It's an exceptional chance to invest in a lifestyle of peace and natural beauty, surrounded by the distinguished homes that define this desirable corner of rural Connecticut. *Town tax records - 3 bedrooms, health file has 2.