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$7,400,000
6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24205691 MLS
Set on a plateau with panoramic, protected views, West Wind Hill is a masterfully crafted estate spanning 391 acres that straddles the Connecticut and New York border. Reached by a private, gated drive that winds past old stonewalls, open meadow, and a serene pond, the property offers a level of privacy rarely found within two hours of New York City. The stone-and-shingle residence was built with singular attention to craft: the architect camped on site before construction began to orient the home for the finest light and views in every season, and the estate's stonework, including a 20-foot great room fireplace, was quarried directly from the hilltop on which the house sits. Reclaimed chestnut floors, hand-detailed millwork, and banks of French doors and windows run throughout the roughly 8,919-square-foot residence, which includes six bedrooms, a paneled library, a chef's kitchen with its own massive stone hearth, a billiard room, a media room, and a wine cellar with tasting room. The primary suite occupies a private wing of the main level. A stone-and-gunite pool and pool house with full kitchen, plus two stone barns, complete the grounds, which also include hiking trails, open meadows, and a pond.

33 Nodine Pasture Rd, Kent
$795,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24202166 MLS
This house is really stunning on so many levels. 8.54 totally private acres at the end of a private road in Kent. Soaring ceilings in every main-floor room, and a first-floor primary with a full bath. There is a see-through, large wood-burning fireplace connecting the living room and kitchen. Spacious sun room with 3 walls of windows just off the kitchen, and a skylight in the kitchen, living, and sun room. There is a formal dining room, and plenty of space for a table in the kitchen as well. A large deck runs the length of the back of the house, with access from the kitchen, living room, and primary bedroom. The basement is unfinished, but it has 14 foot ceilings throughout with a fireplace and plumbing in place for a full bathroom. This house has two garages, and plenty of storage. Tucked in one of the most beautiful towns in Litchfield County, it is a real find.

12 Woodin Rd, Kent
$2,795,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24204321 MLS
Tucked on a hilltop in sought-after South Kent, this handsome Colonial offers the kind of privacy and view that rarely comes to market - 14+ acres of quiet woodland framing breathtaking sunset vistas over the Litchfield Hills. Inside, chic interiors balance classic New England character with a modern sensibility. The heart of the home is a true chef's kitchen with soapstone counters, an oversized island with seating, and a butler's pantry for effortless entertaining. It flows naturally into a glass-walled dining room, which in turn opens onto a bluestone patio and outdoor grill station, where the long mountain views take center stage. Both a cozy den and a living room anchored by a fireplace spill out to a screened porch, blurring the line between indoors and out. Upstairs, a serene primary suite is joined by two additional ensuite bedrooms, while the finished lower level adds a fourth ensuite bedroom, laundry room creating flexible space for family and friends, plus a two car garage. Rounding out the property is a handsome detached barn with four stalls, ready to become a party barn, studio, or return to its equestrian roots. A rare offering of privacy, view, and turnkey living in one of Litchfield County's most desirable areas.

81-B Geer Mountain Rd, Kent
$1,375,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201595 MLS
Welcome to Hawksview, an extraordinary private sanctuary nestled amongst the trees with a warm and woodsy feel. Located on a private country road in the prestigious estate section of Kent, this stunning retreat offers low taxes with 26.7 acres of land in forestry (Forestry 490). Prepare to be captivated by amazing views from almost every angle of this home, which features soaring ceilings throughout. The interior boasts a chef's kitchen with granite countertops and gorgeous skylights with an adjacent dining area that feels like a greenhouse. The cozy, yet versatile layout, includes a primary suite with vaulted ceilings, a dressing room, deck access, and an ensuite bathroom with a steam shower and Jacuzzi tub. The living room beckons for gatherings around the wood burning stove and generous windows lend all season distant views of The Appalachian Trail, Macedonia State Park, and St. John's Rock Ledges. Outside, the wraparound deck invites you to entertain and follow the sun. With a lower level workshop and 2 car garage, one can enjoy fun projects right at home. An outdoor enthusiast's paradise, the property features private trails that lead directly to Cobble Brook Vista conservancy trails. Enjoy the ultimate private mountain retreat just 4 minutes to the center of Kent and 6 minutes to Kent Falls. This exceptional location is also just 20 minutes to Mohawk Ski Area (and a short drive to other nearby ski areas) and 20 minutes to Wassaic Station for easy train service to NYC

91 Muller Rd, Kent
$545,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24194978 MLS
A welcoming front porch is the perfect 'rocking chair' spot...to take a breath of fresh air and gaze out over the serene, protected pasture stretching across the road. With freshly painted spaces, this classic farmhouse seamlessly blends New England charm with modern comfort, offering incredible value in the heart of Kent. Inside, newly refinished hardwood floors gleam under natural light, welcoming you into an expansive open-concept living space where kitchen, dining, and cozy moments flow naturally together around a magnificent fieldstone fireplace. The adjacent formal dining room and living room offer additional entertaining spaces. The story of relaxation continues upstairs in the impressive primary suite, defined by a vaulted ceiling which creates a bright, airy sanctuary. Here, you'll find a spacious walk-in closet and an en-suite bath designed for unwinding, complete with a soothing Jacuzzi tub and separate stall shower. Two guest bedrooms and a full bath complete this level. Down below, a finished lower level with glowing light and elegant French doors offers flexible space for a home office, media room or guest lounge that leads right out to the yard. Equipped with a high-ceilinged, attached two-car garage offering plenty of extra storage or workshop potential, the property's true magic extends far beyond its walls. With thirty acres of open space directly abutting the rear of the property, you'll enjoy total privacy and endless natural views

33 Stone Fences Ln, Kent
$750,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24076721 MLS
Architect designed renovation, this wonderful house, situated back from the road on 10 private acres, is special. Wrap- around deck, floor -to -ceiling windows, and an active, babbling brook below the house that you can hear when the weather permits. Large primary suite with private balcony overlooking the brook, an ensuite bath , and private office. Modern, wood- burning stove in the bedroom corner, and wood -burning fireplace in the living room. Granite counters and stainless steel appliances make this compact kitchen classy and a delight to work in, also adorned with beautiful windows looking out on the brook. Two cozy, light-filled bedrooms on the bottom floor, both with sliders onto a private crushed stone patio by the brook. The property also boasts a wonderful wood and garden shed, and a new generator. This is honestly a lovely, private getaway.

60 Muller Rd, Kent
$475,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24189536 MLS
Charming Country Cottage in the Heart of Kent Tucked away on a peaceful private road just a short walk from the vibrant village of Kent. This charming country cottage offers the perfect blend of privacy, convenience, and classic New England character. Surrounded by picturesque meadows and mountain views and located near the scenic Housatonic River, this home provides a tranquil setting while remaining close to everything Kent has to offer. A spacious deck welcomes you into a bright, open-concept main level featuring generous living and dining areas, ideal for entertaining or relaxing. Upstairs you'll find a large primary bedroom and two additional bedrooms, all served by a full bathroom. Whether you're searching for a full-time residence, a weekend getaway, or an investment property, this home offers endless possibilities to make it your own. Major improvements provide peace of mind, including a year old roof, new windows, well, and septic system. Enjoy the convenience of walking to Kent's charming shops, restaurants, Kent Center School, and the renowned Kent School. Metro-North train service to New York City is just minutes away making this an ideal country retreat with easy access to the city. Don't miss this opportunity to own a home in one of Litchfield County's most sought-after communities.

39 Johnson Rd, Kent
$1,195,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24179647 MLS
Steeped in history and radiating timeless elegance, this 1870 Victorian masterpiece stands as one of Kent's most grand and storied residences. Boasting a striking architectural facade, this magnificent home welcomes you into its grand entrance, featuring soaring ceilings and beautiful woodwork that flows throughout the entire property. Throughout its rich past, this versatile estate has been cherished both as a luxurious private residence and as a welcoming bed and breakfast. Today, it stands ready for its next chapter, offering multiple rooms across the premises and an incredible canvas for the next owner to bring their own vision and elevate it to its next level of brilliance. Location is everything. Situated right in the heart of the vibrant Kent Village center, this property offers unmatched walkability. Step outside your door and immerse yourself in the town's renowned culture-just a short stroll to world-class art galleries, gourmet restaurants, boutique shopping, local museums, and premier antiquing. Whether you envision a spectacular, expansive private compound, a boutique hospitality venture, or an elegant live-work space, the possibilities here are as vast as the home's rich history. Don't miss the rare opportunity to own a true piece of Kent heritage and define its next great era. Schedule your private showing today.

67 N Main St, Kent
$1,395,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24184750 MLS
First time ever on the market: this custom Contemporary abuts hundreds of acres of conserved land owned by the State of Connecticut, offering sweeping pastoral views and exceptional privacy less than five minutes from Kent Village Center. Inside the ~2,800 sq ft main house, an open floor plan blends with sophisticated country character. The main level kitchen is light-filled with breakfast bar seating, opening to a sitting area that flows into a sunroom and out to a bluestone patio framing the view. A formal dining room with vaulted ceiling opens to the living room, anchored by a fireplace. A main level bedroom with private bath completes this floor. Upstairs, the primary suite features a vaulted ceiling opening onto a sleeping porch, with a private bath of its own. Two more bedrooms share a full bath on this level. The home was also expanded to include an ~800 sq ft separate guest apartment, currently used as an expansive home office. This area would make a wonderful guest space, with the two existing offices easily converted into two additional bedrooms. The space already includes a living room, dining area, kitchenette, and full bath. The lower level of the main house has been finished to include a media room and laundry, and the original two-car garage is now finished storage space, easily converted back if needed. A rare find in a sought-after location, just two hours from NYC.

14 Flanders Ln, Kent
$1,250,000
1 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24183167 MLS
Western-facing views from this homestead spanning over 50 acres in Kent. Immerse yourself in nature, where you can hike, mountain bike, cross-country ski, fish, or hunt on your own land! A delightful 1-Bedroom residence boasts an open-concept living and kitchen area that seamlessly transitions to an elevated deck, ideal for enjoying sunset mountain views. Enjoy the home just the way it is, expand it, or retain it as a guest house while constructing your dream home. A detached barn that includes a wood shop and three garage bays offers remarkable versatility. The Barn/Garage shares the same distant views as the main house and features a spacious layout that invites finishing touches. Envision this area overlooking the stunning sunset! Perhaps part of it could serve as a Home Office, a Gym, or your Recreation Barn. All these functions could be combined to still accommodate some Vehicle Storage bays! The potential is huge! This 50-acre property features diverse landscapes, including the slopes of a mountain that descend into a charming valley with a scenic brook. A former logging trail winds through open fields and established woodlands, ultimately reaching a brook that signifies the beginning of the famous Kent Falls. Located under two hours from NYC and just minutes from the villages of Kent, Cornwall, New Preston, and Lake Waramaug.

178 Carter Rd, Kent
$1,139,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24182669 MLS
This exquisitely appointed Colonial estate has the WOW factor! At its heart lies an opulant living room, where soaring cathedral ceilings meet a wall of grand windows, inviting the outdoors in, while a bespoke fireplace serves as a luminous anchor of comfort. The expansive, double height windows provide dramatic light to the open plan living/ dining/ kitchen. Miele and Bosch appliances are featured in the Chef's kitchen with a breakfast nook and a formal dining room adjoining. Transition effortlessly to the private, elevated deck; a serene sanctuary designed for seamless indoor-outdoor entertaining amidst tranquil vistas. Exceptional versatility defines the residence, featuring a main level Bedroom-ideal as a guest suite or private study; complete with an adjacent full bath. Retreat to the primary suite, a masterwork of design boasting vaulted ceilings, a statement chandelier and a cozy fireplace. This private haven further indulges with a dedicated seating area, an intimate balcony for morning coffee, full bath with double vanities, soaking tub, large stall shower AND an enormous dressing room. The two additional bedrooms are generously appointed with the convenience of walk-in closets and a Jack-n-Jill full Bath. The sun-drenched walk-out lower level is reimagined as the ultimate wellness retreat, featuring picture windows that frame the landscape. This multifaceted space offers a dedicated gym, spacious sauna and full Bath with rainfall shower for a true spa experience.

11 Stone Fences Ln, Kent
$1,095,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24179592 MLS
Built in 1830 and set on 3.5 private acres abutting hundreds of acres of Connecticut State land, this five-bedroom Colonial is a rare find, a property where history, privacy, and natural beauty converge. Jaw-dropping sunset views set the tone from the moment you arrive. Inside, a recently updated kitchen anchors the main level, opening to a well-proportioned dining room made for long dinners with friends. The spacious living room, centered on a fireplace, is the kind of place you'll want to spend a winter evening. A main-level primary suite offers a private deck, a generous walk-in closet, and a spa-style bath, a true retreat within the home. Upstairs, four additional bedrooms share a full bath, with room for family, guests, or a dedicated workspace. The finished lower level adds a media room, home office, and laundry, keeping daily life organized and out of the way. Outside, the property comes alive. A side deck off the living room is perfect for morning coffee. The pool area, anchored by an impressive millstone table, is ready for summer entertaining. The perfect country retreat only two hours from NYC.

321 Kent Cornwall Rd, Kent
$1,100,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24170157 MLS
Set on 14+ private acres abutting Connecticut State land, this chic three-bedroom farmhouse offers the kind of quiet that's increasingly hard to find - and interiors that make you want to stay. The main floor is built around an open, light-filled plan that flows naturally from a chef's kitchen, featuring shaker-style cabinetry, butcher block counters, a farmhouse sink, and a professional range, through a generous dining area and into a living room anchored by a fieldstone fireplace. Step outside and relax or entertain on a back deck overlooking the lawn and surrounding forest. A powder room and laundry complete the level. Upstairs, a comfortable sitting area with a second fireplace connects two well-proportioned bedrooms sharing a full bath. The primary suite is a proper retreat: a handsome built-out office, a spa bath with soaking tub, and a walk-in closet done right. Outside, a classic red barn with metal roof adds character and utility. The Litchfield Hills at their best: two hours from Manhattan, with Kent's village life, Appalachian Trail, the Housatonic River, and Mohawk Ski Mountain all within easy reach.

9 Old Paddock Ln, Kent
$915,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24160643 MLS
Beautifully renovated antique colonial on 4.5 private acres with a tumbling brook. Hardwood floors and original beams throughout, two wood- burning fireplaces, custom lighting, original wide-plank floors in some rooms, and a gorgeous, country kitchen with built-in appliances, including a warming drawer. The formal dining room anchors the heart of the home, with a small private study for multiple uses on one side, and a large living room on the other side. Every room shows loving attention to detail and comfort. Added onto throughout the years, the house flows comfortably. The original cottage, connected by a light-filled inner hallway with hardwood floors, offers a lovely family room or second living room, with a wood fireplace, a full bath that includes an imported English claw-foot soaking tub, and a cozy upstairs bedroom for guests. There are two large barns: one is a combination garage, tool shed, and wood shed. The other, built using the chestnut beams from the original barn on the property, is capacious, with a cement floor and truly endless possibilities. Gorgeous antique stone walls and perennial gardens abound, and the property is private and protected in the back by its natural landscape. Split air conditioning and a generator assist with comfort without sacrificing authenticity. Close to town and 20 minutes to the Ten Mile River Train Station. This home has been beautifully maintained, and will be standing long after any of our new houses are long gone. Turn Key!

221 Segar Mountain Rd, Kent
$1,995,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24166682 MLS
Two Homes. 15.66 Private Acres. Long Views Over Kent Hollow. A rare Litchfield County compound in South Kent's exclusive Kent Estate area - two distinct architectural statements from two eras, set on 15.66 secluded acres with a brook running through the property and views over Kent Hollow. The Main House (1993 contemporary, 3,400 sqft): Built for light and landscape. Walls of glass frame long views; an open floor plan flows from the chef's kitchen to expansive decks and two screened porches. Four bedrooms (first-floor den/office could be used as bedroom), 2.5 baths, four fireplaces. Viking double oven and 6-burner cooktop, two Miele dishwashers, Sub-Zero, wine fridge, Carrara marble. 5 minutes to Lake Waramaug, 7 to New Preston. The Guest House (1955 midcentury, 1,065 sqft): 2BR/2.5BA with original character intact - fireplace, expansive deck, independent living quarters. Comparable Kent STRs command $300-$750/night, projecting $35,000-$65,000/year gross. Ideal as guest house, income suite, multi-generational residence, or studio. Together: ~4,500 sqft, six bedrooms, five baths, five fireplaces, two screened porches. 15.66 acres of woods, water, and quiet.5 minutes to Lake Waramaug, 7 minutes to New Preston.

14 Straight Rd, Kent
$950,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24163631 MLS
An exquisite three-bedroom Cape-style residence, this property is poised upon four pristine acres on Studio Hill. Constructed in 1990 and meticulously enhanced by an expansive great room addition in 1993, this move-in ready home offers a sophisticated blend of classic design and modern amenity. The sun-drenched, open concept floor plan commences with a welcoming living room, anchored by a handsome wood-burning fireplace. The kitchen features elegant granite countertops with stainless steel appliances, with sliding glass doors providing seamless ingress to the deck for al fresco dining. The adjacent dining area flows effortlessly into the main living space, providing an ideal layout for both intimate dinners and larger holiday gatherings. The architectural centerpiece of the home is the impressive post and beam great room. The main level is further distinguished by a primary bedroom suite complete with a private walk-in closet, which facilitates convenient single-level living. The first floor also hosts the laundry facility and provides access to the attached two-car garage. The upper level is thoughtfully configured with two guest bedrooms and a full bath. Refinished hardwood flooring graces the entire residence. The property's beautifully manicured grounds are framed by natural woodlands, creating a picturesque sanctuary and an exceptional setting for observing local wildlife and birdwatching.

15 Studio Hill Cir, Kent
$5,500,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24148400 MLS
"The Falls." Prominent Modernist Architect, Charles Gwathmey of Guggenheim Museum renovation fame, designed this masterpiece in one of the most beautiful locations, offering dramatic views, cascading waterfall, nestled on 40+ acres of beautifully landscaped grounds with serene stream and extensive stonework. The property boasts a breathtaking western view of the Litchfield Hills. Just minutes to Kent Center with Swyft, Wilson's and great shopping, this exceptional offering provides tranquil escape while remaining close to vibrant shops and renowned award winning restaurants and just 90 minutes from NYC. Step inside and discover a light filled haven with soaring ceilings and curved walls and a stunning view of the waterfall from the Living room, which opens on to a picturesque stone terrace overlooking the babbling brook. A Michael Arad-designed addition of a full bedroom suite complete with office and captivating vistas. A tennis court, gorgeously designed pool and spa, acres of meadows and rolling landscape make this the perfect estate. A natural planted roof, and Deborah Nevins-designed park, gardens, perennial paths. The Stephen Sills designed interior spaces complement the curved walls, glass-covered corridor,

23 Mauwee Brook Rd, Kent
$699,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24131797 MLS
Set well back from the road across Bull Mountain Brook is this incredibly private brookside home on South Kent's lauded Geer Mountain Rd. Perched over the brook the house offers 1750 sq. ft. of wood floors, three fireplaces, open floorplan and plenty of windows for views and sunlight. There are three bedrooms with the primary on the main level for ease and comfort. The screened porch offers a blissful retreat set above the babbling brook. The brook meanders through the lightly wooded 2.13 acres that features mature professionally landscaped grounds and a canvas of native trees and shrubs. Easy to maintain and even easier to enjoy.

103 Geer Mountain Rd, Kent
$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

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