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$2,750,000
4 Beds 5 Baths ACTIVE Status 24167130 MLS
Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece, appointed with premium appliances, a walk-in pantry, oversized island, and stylish bar. It opens seamlessly to a spacious screened porch with inviting dining and lounge areas. Outdoor living is elevated by an expansive ipe deck that functions as a true open-air great room-ideal for al fresco gatherings. The dining room extends to a charming sunset porch adorned with a pergola and irrigated herb garden. The grounds are equally impressive, with professionally designed landscaping that includes an apple orchard, restored stone walls, and a picturesque pond with cascading waterfall. A striking custom pool features a lap lane, lounging platform, and firepit with integrated stone seating, creating a private resort-like setting. Addl highlights include a 3,000-bottle wine cellar, heated garage, pergola-covered carport, and a newly finished oil-and-stone driveway. Ideally located just minutes from the chic shops & fine dining of Washington and Woodbury. Nearby land trust trails offer plentiful hiking. This turnkey property offers easy access to the very best of Litchfield County! Agent Owner.

220 Painter Hill Rd, Roxbury

$7,950,000
6 Beds 8 Baths ACTIVE Status 24166431 MLS
New Construction BY Ritzzo Development a premier builder! Situated on a country road among luxury estates, this 8,050 sq. ft., to be built new construction strikes the perfect balance of secluded privacy and commanding views. The 8.18 acre lot is bordered by state forest on 3 sides. The welcoming front porch sets a sophisticated tone, leading into an interior defined by 5" white oak flooring, Pella windows and doors with exquisite craftsmanship throughout. The heart of the home is a chef's kitchen with custom white oak cabinetry paired with professional Sub-Zero/Wolf appliances, an inviting island, and a sun-drenched breakfast room. Dramatic architecture defines the family room, where exposed beams complement a soaring vaulted ceiling and a striking wood-burning hearth. The residence offers six en-suite bedrooms. The expansive primary retreat is a true standout, boasting dual bathroom suites and matching, dual walk-in closets. Functional luxury continues with a main-level guest suite, a dedicated home office, and two powder rooms on the main level. Personal gym in the lower level. Outdoor highlights include a premium granite patio with built in barbeque overlooking a stunning 18x36 in-ground gunite pool. For peace of mind the electric service is buried with 400-amp service, with a dedicated EV charger, plus a fully equipped Generac 26KW auto transfer generator. This is a rare opportunity to start the year in a home designed for ultimate style, comfort and sophistication

197 A Tinker Hill Rd, Washington

$899,000
5 Beds 4 Baths ACTIVE Status 24163806 MLS
Rare opportunity to own in one of Connecticut's most sought-after private lake communities-welcome to 3 Weldon Court at Woodridge Lake. Perfect for year-round living or a second-home retreat, this beautifully maintained Colonial offers quality 2x6 construction and a whole-house generator. Enjoy lake access, clubhouse amenities, and seasonal lake views, with beach just across the street-swim, fish, or kayak without the price of direct waterfront. This sun-filled home features a flexible layout, including a first-floor guest suite with private entrance and full bath. The spacious kitchen with cherry cabinets and granite counters opens to a bright family room with fireplace and built-ins. Formal living and dining rooms provide inviting spaces to gather. Upstairs, the expansive primary suite includes a sitting/office area, lake-facing window, private deck, walk-in closet, and full bath with double vanity. Three additional bedrooms, a full bath, and laundry complete the second floor. An unfinished lower level offers endless potential for recreation or fitness space. Relax on the deck after a day at the lake or entertain with ease. Community amenities include a lakefront clubhouse, pool, marina, tennis, pickleball, basketball, fitness center, cafe, playground, and year-round events. Conveniently located near Litchfield Green, Mohawk Mountain, Goshen Fairgrounds, shopping, dining, the Appalachian Trail, and Housatonic River. A must-see home offering comfort, recreation and beauty.

3 Weldon Ct, Goshen

$995,000
4 Beds 4 Baths ACTIVE Status 24164547 MLS
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.

24 Hickory Ln, Roxbury

$1,469,000
4 Beds 4 Baths ACTIVE Status 24163570 MLS
Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room, spacious dining room and chef's kitchen with striking polished hardwood center island. Upstairs, Primary En Suite Bedroom with lovely clawfoot tub, double sinks, large separate shower and spacious dressing room. Two more bedrooms share a charming hall bath. Finished lower level currently outfitted as a family room with French doors to a serene patio leading out to the pool, another en suite bedroom and two more finished flexible spaces. (Makes the total finished sq feet: 3676!)The perfect peaceful location, minutes from the centers of Roxbury and Washington. Must see!

33 Sentry Hill Rd, Roxbury

$7,900,000
7 Beds 8 Baths ACTIVE Status 24155364 MLS
Introducing Butternut Brook House; a Majestic, Luxurious Country Estate commanding stunning 360-degree views of the Litchfield Hills. Representing a masterful fusion of absolute privacy, consummate sophistication and breathtaking natural beauty, this legacy property spans over 36 pristine acres of rolling countryside. The palatial main residence encompasses an impressive 13,056 square feet, including a recently appointed lower level. Accommodations are lavish, with seven principal bedrooms, each distinguished by its own fireplace and six & a half sumptuous baths. Inside, discover character-filled living spaces designed for grand entertaining and intimate repose. A spacious open plan kitchen / dining / family room flows into the formal Dining Room with custom millwork adjoining the elegant Living Room and screened porch. Luxury amenities abound, including an elevator to all 4 levels, a serene spa, dedicated billiards room and a timeless wood-paneled library/study. The second floor hosts dual primary suites and four supplementary bedrooms, while the third floor is home to a dedicated bunk room and a state-of-the-art home theater. The finished lower level is an entertainer's dream, offering a spacious recreation room, climate-controlled wine cellar, wet bar, two additional fireplaces, gym area and a half bath. The estate's auxiliary structures elevate the property to a luxurious, multifaceted estate and gathering complex.

19 Seherr Thoss Dr, Litchfield

$1,495,000
4 Beds 5 Baths ACTIVE Status 24162311 MLS
Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray ceilings, and abundant natural light throughout. The gourmet kitchen features custom cherry cabinetry, granite countertops, stainless steel appliances, and a butler's pantry, opening to a warm hearth room with a fieldstone fireplace. A sunken family room with a brick fireplace and French doors leads to a stone patio, creating an ideal flow for indoor-outdoor living. The upper level offers a spacious primary suite, three additional bedrooms, three full baths, and a versatile rooms suitable for a home office, lounge, or playroom. The walk-out lower level with 9-foot ceilings provides approximately 1,950square feet of additional living space, including a recreation area, full bar, exercise room, bedroom, full bath, and flexible space for entertaining or extended living. The grounds offer a peaceful retreat with woodland trails, a stream, fire pit, outbuildings, and a two-story pool house. Additional features include a chicken coop and utility structure, enhancing the property's country lifestyle appeal. Conveniently located near local amenities while offering privacy and tranquility.

380 Southbury Rd, Roxbury

$845,000
4 Beds 3 Baths ACTIVE Status 24161651 MLS
Privately set at the end of a long drive and surrounded by protected and conservation land, this well-cared-for home offers 16.61 acres, 4 bedrooms, 2.5 baths-a rare combination of privacy, scale, and move-in-ready ease in the heart of Cornwall. The home features a comfortable, classic layout designed for both full-time living and weekend retreat. Light-filled interiors and thoughtful proportions create an inviting atmosphere throughout, while the fireplace anchors the main living space with warmth and character. The setting is what truly sets this property apart. Sweeping mountain views extend across the pristine Coltsfoot Valley. With surrounding land protected, these views remain preserved, offering a level of permanence that is increasingly hard to find. A compelling opportunity to own meaningful acreage with enduring views, privacy, and immediate livability-just minutes from the village centers of Cornwall and the broader Litchfield County amenities.

82 Valley Rd, Cornwall

$985,000
3 Beds 2 Baths ACTIVE Status 24159885 MLS
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.

179 South St, Roxbury

$1,885,000
4 Beds 4 Baths ACTIVE Status 24158388 MLS
Effortless elegance on seven acres directly across from protected conservation land. A dappled willow hedge and a classic pea stone driveway lead to this fully reimagined four-bedroom, three-and-a-half-bath retreat. Interiors are by Ellsworth Home, the New York and New England design studio behind the 2024 renovation - featured recently in Litchfield Magazine. Classic mouldings, high ceilings, and oversized windows carry through the first floor. The 13-foot kitchen island, AGA gas range, custom hood, and Bosch dishwasher make it a kitchen built for families who cook and entertain. It opens directly to a den with a soapstone gas fireplace and, beyond it, an east-facing screened porch. At the front of the house, a cozy living room - anchored by a brick wood-burning fireplace - sets an entirely different mood, while the dining room offers more traditional, sit-down entertaining. The main-level primary suite allows for the ease of one-floor living; upstairs, three more bedrooms include a second en-suite plus a third full bath. An approved pool site, attached two-car garage, and full unfinished basement leave room to grow into the property on your own timeline. Privacy reigns at the back of the property, where an old stone wall fades into the tree line and the woods take over.

200 Sharon Mountain Rd, Sharon

$259,000
3 Beds 2 Baths ACTIVE Status 24140514 MLS
This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample amounts of storage. The home sits on a flat, level yard with a huge storage shed, perfect for outdoor gatherings, storage, gardening, and play. Multiple decks off the home create inviting spaces to relax and take in the surroundings. Located just moments from a local boat launch, this property is ideal for those who love recreational water access. You're also close to the town green, shops, and everyday conveniences, making this home the perfect blend of historic charm and modern lifestyle. Schedule to view today!!

118 Meadow St, Winchester

$699,900
3 Beds 2 Baths ACTIVE Status 24139265 MLS
This authentic antique home is ideally located on one of Bethlehem's most desirable country roads, surrounded by other elegant historic properties. Meticulously maintained, it showcases true period charm with spacious rooms, high ceilings, original wide-board floors throughout, and a grand central chimney serving three fireplaces. The main level is perfect for both daily living and entertaining, featuring a large eat-in kitchen, a cozy wood-paneled study with built-in bookcases and fireplace, an inviting living room with fireplace, and a gracious formal dining room-all generously proportioned for comfortable gatherings. Upstairs you'll find three well-sized bedrooms, a full bathroom, a large walk-in attic over the kitchen that's already framed and ready to become a luxurious primary suite, plus a separate walk-up attic with plenty of headroom for additional finished space. The beautifully landscaped grounds include a sweeping level lawn, a fully approved extra building lot with its own private driveway, and a handsome post-and-beam barn offering ample room for vehicles, workshop space, and storage. Move right in and enjoy this classic beauty as-is, or take advantage of the rare opportunity to expand, add a guest house, or create a family compound.

114 Carmel Hill Rd N, Bethlehem

$1,790,000
4 Beds 5 Baths ACTIVE Status 24136657 MLS
Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury

$1,100,000
4 Beds 4 Baths ACTIVE Status 24135269 MLS
Custom-Built Home on 1.45 Acres with Luxury Finishes & Outdoor Oasis in Watertown, CT!! Welcome to this stunning custom-built home offering over 4,600 square feet of beautifully crafted living space on 1.45 private acres. Designed with comfort and entertaining in mind, this home features 4 spacious bedrooms with the possibility of a 5th, along with 4 full bathrooms and 1 half bath, including a potential in-law suite setup. Step inside to find hardwood floors throughout, an open-concept layout, and custom stonework that adds timeless character across the property. The expansive kitchen, living, and dining areas flow seamlessly to create an inviting and functional living environment. Outside, enjoy the ultimate entertaining space with a custom patio, pizza oven, and firepit, perfect for gatherings year-round. 12X22 Shed with garage for extra storage. Additional highlights include 3 car attached garage, forced hot air heating, generous storage and closet space, flexible layout ideal for multigenerational living or home office needs. This one-of-a-kind property combines luxury, functionality, and craftsmanship in a picturesque setting. A true must-see!

114 Wheeler Farm Rd, Watertown

$1,080,000
5 Beds 3 Baths ACTIVE Status 24044161 MLS
Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at your fingertips. The property's outdoor allure is undeniable. Multiple walking or riding trails invite adventure, and the gardens, barn, carriage house and stone outbuilding offer endless possibilities for outdoor enjoyment. Step inside and be greeted by the warm embrace of rich hardwood floors, two fireplaces, French doors, and meticulously crafted woodwork that tell tales of yesteryear. The updated kitchen, equipped with a premium Wolf gas stove and a convenient butler's pantry, offers a perfect stage for culinary exploration. The living room, anchored by a cozy fireplace, formal dining room, and library, are infused with great natural light that dances across the spaces. The primary bedroom suite, a sanctuary of comfort, boasts its own fireplace, ensuring a restful retreat at day's end. Accommodate guests in style with four additional bedrooms, including a secluded guest room with a private stairway. Located in the heart of nature's playground in Litchfield county. Close to skiing, hiking, restaurants, and parks in Norfolk and Barkhamsted, and near the Farmington River.

77 Deer Hill Rd, Colebrook

$1,650,000
4 Beds 5 Baths ACTIVE Status 24130930 MLS
Escape to this mountaintop retreat with sweeping, unobstructed views located off one of the most desirable scenic roads in the Litchfield Hills. Set in complete privacy, this four-bedroom home offers a perfect blend of comfort and sophistication with an open-concept layout designed for both relaxation and entertaining. The chef's kitchen, featuring a central island, flows seamlessly into a cozy reading nook with fireplace, a screened porch, and a dining area that opens to an expansive deck overlooking the breathtaking vistas. The spacious living room, anchored by a striking fieldstone fireplace, also connects to the deck and includes a charming home office. Upstairs, the primary suite offers a private balcony, spa-like bath with soaking tub, and walk-in closet. An additional ensuite bedroom, two more bedrooms with a shared full bath, and convenient laundry complete the upper level. The walkout lower level provides versatile living space, currently used as a media room and gym, and includes a full bath. Located just minutes from the shops and restaurants of Kent's vibrant village center-and only two hours from New York City-this property is the ultimate country retreat.

168 Cobble Rd, Kent

$3,950,000
8 Beds 10 Baths ACTIVE Status 24100203 MLS
Come see this remarkably private property a stone's throw from the center of Litchfield. This stately home was built in 1992 and boasts over 10,000 s/f of finished space. The grounds are professionally landscaped and have a beautiful patio, pool and greenhouse. There are 8 bedrooms and 13 bathrooms along with a powder room . The sunny , modern, large eat-in kitchen open onto a patio, which then leads to the saltwater pool. A main floor guest bedroom suite with its own bathroom is an added convenience and can be a ground floor primary. There are lots of space for grand entertaining in the formal dining room, living room and great room. Plenty of cabinetry and shelves to display your treasures. You can warm yourself by the fireplaces. The master bedroom suite on the upper level has it all, walking closet, fireplace , sunroom and a large bathroom with steam shower and jet tub. 3 additional bedrooms round up the second floor, all with en-suite bathrooms. A separate laundry room is conveniently located on the bedroom level. The 3 floor has a loft and 2 additional bedrooms also with en-suite bathrooms.The lower level is fully finished and is a walk-out to the grounds. It also includes a wine cellar, a gym and a kitchenette. A separate apartement with a patio is located above one of the garage, which house 3 cars. Another garage for 6 cars is an additional outbuilding. Acreage is consisting of 3 separate parcels which are included w/sale.

184 Fern Ave, Litchfield

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