luxury real estate for sale Southbury, United States

Welcome to this beautifully updated Country House model offering two bedrooms, two full bathrooms, and a convenient, level walk from the one-car garage. Inside, you will find newer windows, updated flooring, and an oversized living room anchored by a classic wood-burning fireplace. The fully renovated kitchen boasts elegant granite countertops and stainless steel appliances, while the primary suite provides a relaxing retreat with a walk-in shower. Step outside to enjoy a spacious patio complete with a top-of-the-line retractable awning. Ideally situated near the historic Winship Barn and River Gardens, this home offers incredible access to community workshops, club spaces, and expansive garden plots. The HOA fee conveniently includes internet and cable service. Please note that all buyers pay a one-time $5,000 equity fee at closing.

BACK ON THE MARKET with a NEW SEPTIC being installed, NEW WELL, and MORE. This generous 5-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with fireplace, a private home office, and a full bathroom. Upstairs, you'll find five sizable bedrooms, including a primary suite complete with a walk-in closet and en-suite 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. It includes a den with fireplace, a possible game room or in-law suite as light streams through a large picture window with views of the backyard. This finished area includes an additional guest room and half-bath. Outside, a 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. Bring your design ideas and unlock this gem's 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.

Timeless Elegance & Immaculate Detail. Welcome to The Naramore House, a piece of living history. Lovingly preserved since 1898, this pristine colonial home seamlessly blends grand historic character with immaculate, turnkey maintenance. A classic wraparound front porch invites you through a charming dutch door into a formal, stately foyer featuring high ceilings and original pocket doors. The massive living room serves as the heart of the home, offering incredible square footage for multiple seating arrangements, media setups, and a cozy fireplace. Host effortlessly in the grand formal dining room and eat-in kitchen, complete with a generous pantry, a charming secondary rear staircase, and screened in sun porch. A luxurious primary retreat featuring a fireplace, private en-suite bath and massive 10x7 foot closet/dressing room. Three additional bright and spacious bedrooms include a versatile room-ideal for a dedicated home office, nursery, or library. The home has a huge attic with potential for expansion. A private patio, stunning formal garden with pagoda and mature trees offer the perfect setting for outdoor enjoyment. A recently renovated barn includes new structural beans and flooring. This lovely home offers in town conveniences like walking to restaurants, shops and local parades while set off of Main Street. Enjoy the beautiful historic architecture with the peace of mind that comes from a property that has been meticulously cared for inside and out.

Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and convenience. An active solar energy system helps offset utility costs and enhances long-term efficiency. Set on 3+ private acres, the property enjoys an exceptional natural backdrop with extensive undeveloped acreage beyond the rear property line, creating privacy and peaceful woodland views. Mature landscaping, a spacious deck, and a serene setting make the outdoor spaces ideal for entertaining or quiet enjoyment. The flexible floor plan includes a private in-law, studio, or home office space, ideal for today's evolving lifestyle needs. Beyond the 3,340 sq. ft. of above-grade living space, the home offers an expansive full lower level providing approximately 1,700 sq. ft. of dry bonus space ideal for storage, recreation, workshop, fitness, or future customization. An enormous walkable attic spanning nearly the entire 2nd floor footprint provides exceptional add'l storage rarely found in homes of this era.

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

Diamond in the rough! This solid and expansive home is waiting for its new life, with you as the steward. It has 3 good sized bedrooms, a bonus room off the primary (which is ensuite), a large partially finished lower level, perfect for a game room, gym, man or woman cave, an open floor plan from the kitchen to the family room, a multi-level deck, an oversized 2 car garage and a large, beautiful yard lined by beautiful stone walls with perennial beds, all located in the highly desirable town of Roxbury, where the average sale price is well north of $1M. 90 minutes to Manhattan, this is southern Litchfield County, so you get the beauty and cultural life found locally, with proximity to Westchester, Fairfield and NYC. Great hiking, restaurants and art abounds within minutes. This is an as-is sale, with the price reflecting the condition of the property. There will be no seller concessions for inspection issues. Will not qualify for FHA financing. Seller will not remove the pool table in lower level. USE CAUTION ON THE DECKS, There are loose boards.

Situated on a stretch of Putting Green Lane, this stand-alone Laurel model offers a refined approach to living within the 55+ community of Oxford Greens. Carefully maintained by its original owners, the three-bedroom, two-and-a-half-bath residence features nine-foot ceilings and rich hardwood flooring throughout the primary gathering spaces. The kitchen is appointed with granite countertops, stainless steel appliances, and a bright breakfast nook. Flowing seamlessly from the kitchen, the family room is anchored by a gas fireplace beneath a vaulted ceiling, creating an understated elegance for daily living or entertaining. The architecture thoughtfully embraces its natural surroundings. Two separate decks provide generous outdoor living space, offering tranquil views of the private, wooded setting directly behind the house. Additionally, a large, unfinished walk-out lower level presents expansive potential for future customization, tailored storage, or a dedicated studio space. The Oxford Greens lifestyle is defined by its golf course ambiance and comprehensive resort-style amenities, all maintained with notably low common charges. Situated adjacent to the acclaimed 18-hole golf course, the neighborhood offers a sophisticated country club atmosphere. A 17,000-square-foot clubhouse serves as the focal point of the community, featuring a fully equipped fitness center, indoor and outdoor swimming pools, and a relaxing hot tub. The grounds also include meticulously maintained courts for tennis, paddle tennis, pickleball, and bocce. This property presents a rare balance of private, wooded serenity and premier recreational facilities.

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.

Welcome to Lot 8 Willow Brook Drive! If your dream has been to build your custom home on a picturesque canvas of classic New England countryside, this property is ready to bring your vision to life. Offering 10 sprawling acres of peaceful, former cattle pasture, Lot 8 provides a gentle, easy-to-build landscape framed by open meadows and surrounding natural woodland. The lot benefits from lovely western exposure, capturing warm afternoon light and golden evening sunsets across the fields. Tucked on the land is the existing foundation of an old barn, offering a solid base with potential to be reutilized in your future building plans. This approved building lot is ready to develop with easy, clear meadows for your architectural vision. Underground power and utilities run right along Willow Brook Drive, and a survey/feasibility map with original percolation and soil data is available upon request. Bring your builder and let your imagination run wild on this magical Roxbury acreage!

Charming cottage on a private setting near Lake Zoar, with near by park and hiking trails. Ideal condo alternate or tranquil retreat. The main level has a living room with cathedral ceilings, an updated eat in kitchen, the primary bedroom and a full bath. A spiral staircase leads to the finished walkout lower level with two bonus rooms, a storage area and a half bathroom and laundry. Central air conditioning, an automatic whole house generator, vinyl siding and propane heat complete home. Improvement sheet available. Charming and tucked away, Mature gardens that bloom seasonally. A special home with lovely accents, flower box and outdoor lighting on the deck. Come visit today!

Rare opportunity to own one of Oxford's finest two-family homes! Custom built by the original owners, this unique property was thoughtfully designed to give each residence its own private entrance, full basement, & attached garage while providing comfortable, independent living. The main home features a welcoming sitting room, private office, guest powder room, formal dining room with pocket and french doors, along with a spacious kitchen centered around an impressive 3' x 9' island. The kitchen opens to a great room with a fireplace, French doors leading to a beautiful outdoor entertaining area. Upstairs, you'll find a convenient laundry room with a utility sink, built-in ironing board, & access to a walk-in attic. The spacious primary suite includes a walk-in closet & a beautifully appointed bath. Three additional bedrooms & a full bathroom complete the second floor. The attached second residence offers an open-concept layout with two bedrooms, a full bathroom, in-unit washer & dryer, a private basement, & its own attached garage-ideal for extended family, guests, or rental income. Set on a beautifully landscaped property, the outdoor living spaces are perfect for entertaining & everyday enjoyment. The main level features an oversized deck overlooking an 18' x 36' in-ground pool and a pergola with a ceiling fan, creating the perfect place to relax on warm summer days. The expansive lower yard offers plenty of room for soccer, football, & other outdoor sports.

Fresh paint, new photos, and the pool is open for summer. This beautifully updated Colonial is situated on a private, lightly wooded lot in Sandy Hook, offering the space, comfort, and lifestyle today's buyers seek. A private driveway leads to this inviting home, which features spacious living areas, a formal dining room, a cozy fireplace, and an updated kitchen complete with quartz countertops, modern cabinetry, and newer stainless-steel appliances. Freshly painted throughout, the home feels bright, clean, and move-in ready. The upper level offers four comfortable bedrooms, including a primary suite with a full bathroom and walk-in closet. The fully finished, heated walk-out lower level provides exceptional flexibility—ideal for guests, an in-law setup, a home office, gym, playroom, media room, or recreation space. It also includes a convenient mini-kitchen. Step outside to a backyard designed for summer entertainment. The heated in-ground pool, complete with a slide, is open and ready for relaxing weekends at home. Additional highlights include a two-car attached garage, updated finishes, and a peaceful setting just minutes from Sandy Hook's restaurants, shopping, parks, hiking trails, and wineries, with easy access to major commuter routes.

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 and it has a brand new steel standing seam roof. 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.

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.

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

If You are looking for land with views to build your dream home, this is it. This is truly an "Estate Property". The 27 acres is cleared and open. There are several building sites at the top with 180 degree views. The land slopes gently down with a brook and 2 small ponds at the bottom. There is a fairly large barn and a smaller shop on the property in need of repairs. They are being sold AS IS! Bring your plans and build in a most beautiful part of the world in a sought after Connecticut town. Litchfield County is rural and beautiful. Enjoy farmers markets and country fairs. Visit any number of great restaurants in the area. There are many art shows, antique shops and boutiques to visit. As for outdoor activities, there are thousands of acres of land trust and hiking trails in Roxbury and surrounding towns. The Shepard River offers great fishing. There are ski areas close by as well as lakes for boating, fishing and swimming. Located under 2 hours from NYC! Taxes are based on 490 farming designation.

Spacious and Welcoming Cape on a Cul-de-Sac! Nestled perfectly in a private cul-de-sac and located in close proximity to the scenic Ledges Nature Preserve, this well maintained sprawling 4-bedroom Cape offers a wonderful blend of timeless charm, modern updates, and fantastic spaces for everyday living. The layout features a sought-after first-level primary bedroom. You will find beautiful hardwood floors spanning the living areas and tile in the foyer, mudroom kitchen and bathrooms. The kitchen space allow for hosting, featuring classic Corian countertops, and island, plenty of cabinet storage, and direct access from the garage for easy grocery unloading. Transition seamlessly from indoor to outdoor living with a heated sunroom for year-round enjoyment and a lovely screened-in porch perfect for bug-free relaxation. Major peace-of-mind upgrades are already done, featuring updated bathrooms and a new roof. The layout includes four bedrooms two and half bathrooms and a finished walk-out basement. This lower level provides plenty of storage space alongside a large, workroom for projects and hobbies. Outside, enjoy your private backyard retreat centered around a sparkling pool, complete with a solar cover to keep the water warm. Practical features round out this property, including tilt windows for easy cleaning, a dedicated generator plug for power backup and a large storage shed fully equipped with electricity. Bring your personal touches to make this house yours!

Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble tech finish was installed with fencing in the rear yard for the pool and pets. The house was originally built by a Master Craftsman with the finest materials.The gourmet kitchen is where everyone lives. There is a center island and field stone fireplace. Thermador appliances include a 6 burner cook top as well as wall oven, built in microwave, a warming drawer, dishwasher and refrigerator. The open floor plan allows you to set up the living room/dining room in a variety of ways. There is a lovely sunroom with a vaulted ceiling off the kitchen. There is a mudroom coming in from the garage with a half bath. The ceilings are 9' on the first floor. The upper level includes a lovely Primary Suite with walk in closets, a luxurious primary bath with 2 sinks, a walk in shower and a soaking tub. There are 3 additional bedrooms on the upper level with one en-suite and the other two sharing a hall bath. The house sits up high with mountain views. The land is gently sloping with a level area with plenty of room to play. Only 90 minutes to NYC!

Presenting a rare opportunity to acquire a 23-acre parcel that has been held within a family for generations. This expansive property, fronting on a tranquil county road, offers a serene and private setting for your future endeavors. The property is a picturesque combination of woodlands, offering an idyllic setting for those seeking privacy and connection to nature. With approximately 800 feet of road frontage, the property provides ample access and visibility, ideal for a potential for a private residence or nature-inspired retreat. Enriching the value of this land, the Flanders Nature Center/ Land Trust encompasses the northern boundary with about 200 acres and the southern edge with about 28 acres, ensuring the preservation of the natural surroundings and offering a legacy of conservation. This adjacency to protected lands promises enduring tranquility and a haven for local flora and fauna. Conveniently located just minutes from the vibrant Woodbury Center, future owners will enjoy the blend of seclusion with the convenience of nearby amenities, including boutique shopping, fine dining, and cultural experiences. Create something truly special in the heart of Litchfield County.

Single-level living in a beautiful Taunton cul-de-sac, right in the heart of Newtown Borough and minutes from the historic center. Offering city water and sewer, this custom-built, four-bedroom ranch sits on a flat, private yard bordered by mature trees and equipped with an Invisible Fence. The sprawling layout positions the primary suite on the east wing, separated by a dramatic family room with vaulted ceilings and expansive windows that flood the home with natural light. Three additional flexible bedrooms occupy the opposite side of the residence. Designed for entertaining, the heart of the home features a serious chef's kitchen and dining area with a wall of sliding glass that seamlessly transitions to the patio and peaceful, flowering backyard oasis. A formal living room with a wood-burning fireplace anchors the home's refined feel, complemented by hardwood floors, granite countertops, a pantry, mudroom, central air, and an attached two-car garage. The massive unfinished basement includes dedicated garage door access—ideal for a car collector, boat storage, or heavy equipment. Enjoy easy access to Main Street's boutique shopping, exceptional dining, local bakeries, schools, and major commuter routes including I-84, Route 25, and Route 34.

Private, Rural setting within a short walk to Roxbury Tennis courts, library and the Roxbury Market.This 4.01 acre approved building lot offers the perfect blend of tranquility and convenience, making it an exceptional opportunity to create your custom dream home. Tucked away on a quiet road, this property features beautiful, light woods that provide a serene and private setting. Enjoy the best of Roxbury's natural beauty and recreational amenities, with the lot located just minutes from a variety of hiking trails. For those who love the outdoors, Apple Lane is just around the corner, offering direct access to the scenic Hurlburt Park. This special parcel offers a rare chance for a quiet escape while keeping you connected to the heart of this charming Litchfield County community. Build the home you've always envisioned and start living the Roxbury lifestyle.Private,

Charming Ranch Living in the Heart of Newtown. This inviting 1,408 square-foot ranch sits on a sunny, level corner lot and offers the relaxed lifestyle so many are searching for. Step inside to cathedral ceilings that create an open, airy feel throughout the living space. A warm fireplace anchors the home, perfect for cozy evenings or quiet mornings with coffee. The single-story layout means no stairs to climb, just comfortable, practical living designed for everyday ease. Outside, the level lot gives you plenty of space to garden, play, or simply enjoy the outdoors. Dickinson Park is just a short stroll away, ideal for morning walks, weekend picnics, or letting off some energy close to home. Newtown living with neighborhood amenities right at your doorstep.