Refine Search
Map
Sort by
$3,295,000
7 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24163614 MLS
Major estate with the highest standards of construction located within the Sunny Ridge historic district. Situated on 10 private, park-like acres with an over-sized heated pool, fabulous stonewalls, giant dining terraces, pond and orchard. 7+ bedrooms, Billiard room, screening room, paneled library, sunroom, new country kitchen, 100-person party room boasts a restaurant size bar, sound system and commercial kitchen, maid's quarters, two guest rooms with en suite bathrooms, and 16-car garage. Tremendous Value! The Best Opportunity on the Market!

10 Sunny Ridge Rd, Washington
$1,549,000
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
$1,025,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24163273 MLS
MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round Spa Pool -- all on the best rural Roxbury scenic dirt road with walking area along the Shepaug River and nearby historic farmhouses and land preserve. All minutes to The Mayflower. Pristine renovated private country home with 3 bedrooms/2.5 baths and an ample home office. Open floorplan Living/Eat-in Kitchen/Family Room with wood burning fireplace and sliders to a year-round, heated pool and patio. Dine or relax on the granite terrace or covered front porch surrounded by mature woods and amazing rock outcroppings. Attached 2-car garage. Mint Condition! Move Right In!

18 Tunnel Rd, Roxbury
$785,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24163359 MLS
Goshen, CT. This well maintained Colonial offers 4 bedrooms 2.5 baths, Kitchen w/granite counters and stainless steel appliances, Family room with fireplace and new 9 foot sliders to deck and patio w/ pergola, Formal Dining Room, Living room, Laundry off of the kitchen, Newer Roof, Newer Boiler, Newer Pavement, Shed, 2 Car Garage w/ Newer garage Door openers, New well pump, full basement, well manicured landscaping w/ large shed. sitting on 1.6+ acres, incredible sunsets off the back deck.

230 Beach St, Goshen
$949,900
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24163005 MLS
Construction to begin summer 2026. Still time to make plan changes and selections.

Lot 3A William Way, Harwinton
$749,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24161489 MLS
Welcome to 55 Litchfield Turnpike-a charming farmhouse colonial set on 7.29 beautiful acres in Washington, CT. Loved by one family for many years, this inviting property is ready for new owners to bring their vision and create fresh memories. The home features a desirable first floor primary bedroom, three total bedrooms, two full baths, a spacious great room, and an open-concept kitchen, dining, and living area with a cozy fireplace. A full basement adds convenience and potential. Outside, the land offers endless possibilities with a 7stall barn and tack room-ideal for horses or any type of farming-plus a 3car garage with a versatile secondfloor loft. Enjoy peaceful country living just minutes from Lake Waramaug and Hidden Valley Preserve, along with the benefit of low Washington taxes. This special property is full of potential and ready to be brought back to life.

55 Litchfield Tpke, Washington
$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
$1,550,000
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
$1,850,000
9 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24159989 MLS
Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.

431 W Wakefield Blvd, Winchester
$875,000
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
$899,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24156376 MLS
Welcome home to this beautiful colonial, in the Merryall section of New Milford. Just 8 minutes from downtown and 15 minutes to metro north, for all the New York bound buyers. This elegant 4-bedroom, 4.5 bath Colonial offers nearly 4,848 Sq.ft of living space between the 2 main levels and finished basement. With a beautiful open concept kitchen and living room, for all your entertainment desires. Formal dining room for holiday parties or family fun. All season sunroom for year-round enjoyment. Cozy family room with fireplace for afternoon tea, or nightly wine-down. Large office for work from home owners. The main level offers so much, and that's just the beginning. As we enter the second level you will see that it hosts 2 primary bedroom suites, for possible in law or weekend company. Laundry room on main level and second level as well. Very convenient. Finished lower level is fully renovated and includes a studio room for whatever your heart desires, workout area and another living room for extra entertainment. As we enter the backyard Oasis you will see professionally designed landscaping with beautiful gardens, well maintained patio and pool. 2 car garage plus a detached extra garage/ workshop space. Newer furnace, well pump, water softener and a generator for added bonuses. Radiant floors in the primary bath and upper laundry. This home leaves no stone unturned. Everything you could ever need with class and style!!

427 Long Mountain Rd, New Milford
$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
$738,500
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24158987 MLS
Experience classic New England charm in this beautiful colonial nestled at the bottom of a hill, offering gorgeous lake views from nearly every room. Sunlight floods the interior through bright windows throughout, creating a warm and inviting atmosphere in each living space. Enjoy serene mornings and breathtaking sunsets from this ideally positioned home, perfectly blending privacy, scenic vistas, and timeless character. This property provides a unique escape with its airy interior, captivating outlooks, and proximity to New Milford's desirable lakeside community. Perfect for entertaining or quiet relaxation, this home is a rare opportunity to enjoy Lake Candlewood living at its finest. Benefit from deeded lake rights and the exclusive Candleset Cove community, with property initiation fee already paid-making lakeside living both effortless and accessible. List of upgrades available ask listing agent.

128 Carmen Hill Rd, New Milford
$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
$7,500,000
6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24155009 MLS
West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open meadow, and serene pond. Spacious rooms perfect for entertaining include a great room with a soaring peaked ceiling and a 20' stone fireplace, sun-filled formal dining room with three exposures, huge Chef's kitchen with a massive stone fireplace and adjoining catering kitchen. Beautiful reclaimed chestnut floors, exquisite detailing and banks of windows and French doors. The paneled library, office and primary bedroom suite are located on the first floor in a private wing of the house. Billiard room, complete with mini-kitchen, full bath and adjoining guest bedroom. Second-floor primary guest room with soaking tub and deck with views. Two bedroom suites with en-suite bathrooms, charming bedroom and an office complete this floor. Lower level with a media room, half-bath, wine tasting room and wine cellar with adjoining prep kitchen. Laundry room, craft room and gym. Beautiful stone steps lead to a stunning pool & pool house with full kitchen & tennis court. Two building maintenance court contains a pumping system for irrigating the lawns and gardens.

33 Nodine Pasture Rd, Kent
$795,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24151754 MLS
This 4-Acre home is nestled along scenic Kent Road in the heart of charming Warren, Connecticut. Located a short drive from many of Litchfield County's active downtowns and amenities. Whether you seek fine dining, boutique shopping, skiing, hiking, or lakeside leisure, this location is in the heart of it all. This exceptional property offers a rare blend of serene privacy, natural beauty, and limitless potential. The acreage connects to the Warren Land Trust, creating a breathtaking backdrop of classic New England nature. Envision a custom home site with sweeping views, inviting entertaining areas, expanded gardens, and classic stone walls all while maintaining the peaceful, wooded seclusion. Since its acquisition in 2021, the current homeowners have meticulously updated and enhanced every aspect of the home, bringing modern comfort and thoughtful improvements for seamless, worry-free living. Inside, the home exudes warmth and sophistication with thoughtfully placed windows and glass doors to create an airy indoor-outdoor flow. Each room has generous proportions, ideal for family, guests, or multi-generational living. With two distinct office spaces, there is flexibility for remote work and creative pursuits. Versatile and turnkey, this property suits a variety of needs: a private primary residence with room to grow, a luxurious seasonal retreat, or a substantial rental investment in one of Litchfield County's most sought-sought-after towns.

34 Kent Rd, Warren
$1,949,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24146457 MLS
NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers scale, privacy, and the relaxed elegance that defines Litchfield County living. Designed for both comfortable daily living and effortless entertaining, the home opens to expansive grounds, a pool, and a setting defined by natural beauty and understated presence. With generously proportioned rooms and a strong indoor-outdoor flow, the property offers immediate enjoyment and the flexibility to personalize over time. Now offered at a compelling new price, this is an exceptional opportunity to acquire a significant Roxbury estate with outstanding value in today's market.

1030 Washington Woodbury Rd, Roxbury
$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
$995,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24140219 MLS
A remarkable 139-acre property located up on Skiff Mountain surrounded by 7,000 acres of protected lands. Most of the property is conserved under the Forest Legacy Program, with building envelopes to include the existing home, barns and detached garage. The value is simply the location and the home can either be renovated or torn down to prepare for building new. The home site overlooks a beautiful pond, with a dock and a large open field that leads one into a mature hardwood forest. Sale is subject to Probate Court approval and being sold "As Is". See uploaded "Conservation Easement and Restriction Agreement", survey and the transfer document for the registered dam with CTDEEP.

308 Skiff Mountain Rd, Kent
$1,495,000
6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24137365 MLS
Historic home with untapped potential in Washington. Set on 3.8 serene acres in the Sunny Ridge Historic District, this 1846 Colonial contains elements of the original house which was built in 1768 on the same location. With approximately 4,200 square feet of living space, the home's six bedrooms and three full, two half baths provide a flexible layout ready for a thoughtful renovation. The proportions of the rooms reflect the era - cozy in scale yet filled with authentic detail: original wood floors, period moldings and working fireplaces that speak to nearly two centuries of character. A large eat- in kitchen and extended screened porch add to its charm. Outside, the 3.8 acre parcel balances privacy and manageability. Surrounded by mature trees and open lawn, there is ample space for gardens, patios, or potentially a pool. Four outbuildings can be used as garages, sheds or possibly a pool house. The location on Sunny Ridge Road, with its historical significance and easy proximity to the Depot's shops, dining and cultural amenities, makes the setting especially desirable. This is an opportunity to write the next chapter of a Washington landmark. Exact property acreage is subject to completion of new survey and lot line revision.

28 Sunny Ridge Rd, Washington
$1,100,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24136619 MLS
An exceptional property with a rare convergence of historic provenance and modern excellence. This magical setting comprises a c.1777 home (once a Tollhouse), that blends 18th c. character, masterfully rebuilt in 2023. Step inside to a main floor that includes, a Kitchen, Dining Room, Parlor, Living Room & Primary BR suite including 3 FP's and a 3-season Solarium/Mudroom, Laundry room (ne' Buttery) and 1/2 BA. The Upper level has 2BR's and full bath. There are warm pine wood floors throughout. The enchanting park like setting includes, 3 parcels= 4.5ac.+-, with a pond, babbling stream, a 2-car barn-style garage with a ~400sf upper level studio incl. a sitting and sleeping area, a heated in-ground pool, well-established perennial gardens and pathways, stone walls and a gently rolling hill that borders the Land Trust. It is Connecticut pastoral perfection at its finest. WAIT!!! There's more...An opportunity to start a new, on-site business, currently, a 400 sf Antique Shop. For the collector, artisan or entrepreneur, seeking a life-work retreat or just pure tranquility. This is a one-of-a-kind property with incredible flexibility, delivering, history, beauty & endless possibilities, it is an extremely RARE opportunity. Are you ready to live your next chapter! Set between the storied villages of Litchfield, Bantam, New Preston & Washington for shopping, dining, hiking, skiing, boating or just relaxing. Conveniently located near top-tier area independent schools

38 Old Turnpike Rd, Litchfield
$1,995,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24136657 MLS
Step into History with Modern Comfort 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
$1,095,000
6 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24128830 MLS
Don't miss this newly listed one of a kind home nestled on 8.44 private acres with views so outstanding they could take your breath away. This 5700 plus sq. ft. home w/6 generous sized Brs, 5.5 baths is only the start. Its primary Br. 25X18 w/Fp, Lg. tiled bath w/jacuzzi & those mountain top views again then to a spacious walk/in closet. There are an additional 4 more bedrooms all with oak floors on this level. ( 2nd Floor ) The main level all with oak floors. (exception tile foyer) features a lg. country equipped kitchen w/all appliances, center island, granite counters, dinning area and more abutting 23' a family room a w/10 ft' ceiling & gas Fp.

5 Lyric Ln, New Milford
$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
$760,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24132367 MLS
Tucked away on a long private road, this light and bright Roxbury retreat combines timeless character with modern comfort. The home features three spacious bedrooms and two and a half baths, thoughtfully designed for both everyday living and effortless entertaining. Soaring ceilings with exposed beams and abundant skylights fill the interior with natural light, highlighting the warmth of beautiful wood floors throughout. The open floor plan creates a sense of airiness and flow, while large windows bring the surrounding nature indoors. Whether you're relaxing in the peaceful primary bedroom or gathering in the inviting living area, every space feels serene and connected to the outdoors. The lower level offers 9'+ ceilings, windows and a walk-out. A rare opportunity to enjoy quiet country living just minutes from the heart of Roxbury - the perfect blend of rustic charm and contemporary style.

38 W Mountain Ln, Roxbury
$1,495,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24110013 MLS
Welcome to 99 Carriage Lane, a private Roxbury estate offering over 6,000 square feet of refined living space, exceptional privacy on nearly four acres, and the opportunity to create a true resort-style outdoor retreat with approved pool plans. Set at the end of a quiet cul-de-sac, this beautifully renovated residence blends timeless architectural details with modern amenities and sophisticated country living. Designed for both comfortable everyday living and effortless entertaining, the home features a stunning chef's kitchen, dramatic family room with soaring ceilings, multiple fireplaces, spacious bedroom suites, and thoughtfully designed living spaces throughout. The expansive interiors provide flexibility for today's lifestyle, including dedicated areas for work, relaxation, and gathering with family and friends. The private grounds offer a peaceful backdrop with mature landscaping, stonework, and room to bring the outdoor vision to life. Approved plans for an inground pool provide the opportunity to further enhance this exceptional property and create a private backyard sanctuary. Located in one of Litchfield County's most desirable communities, 99 Carriage Lane offers the perfect balance of privacy, elegance, and convenience. With nearby villages, dining, recreation, and easy access to New York City.

99 Carriage Ln, Roxbury
$3,395,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24057876 MLS
A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in the beautiful Litchfield Hills with spectacular views that go on for miles. This property includes a four bedroom, five and a half bath main residence, in ground heated Gunite pool, tennis court, one-bedroom caretaker's apartment over a 3-bay garage, two bedroom guest apartment and greenhouse. This compound offers an intriguing mix of elegant sophistication and quiet country road living. Highlighted by judges paneling, the large two-story main foyer is breathtaking. An evening soiree for a large gathering of guests is easily achieved in the public rooms. Both rooms offer a touch of grandeur with extra tall ceilings, tall windows and exquisite detailed moldings. The formal dining room is generous in size with tall windows. The home also offers an array of comfortable spaces for intimate gatherings. The delightful and sunny great room includes the updated kitchen with dining, sitting area with fireplace bordered by floor to ceiling bookshelves and French door that leads to the deck overlooking the magnificent view. There is a family room with fireplace, rec room and full bath in the walk-out lower level. The main floor primary suite is extra special with a fireplace, French doors to brick terrace, and full bath with sauna. The three additional bedrooms, all with full baths, are nicely sized. Special in every way and just 90 minutes from NYC.

11 Ravenrock Rd, Roxbury

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.