$792,027Average Value$441Average Price per Sq Ft20Homes For Sale
Woods, mountains and rolling hills in Kent
Kent is a rural community in the woods, mountains and rolling hills of Litchfield County. The community on the far west side of Connecticut often serves as a second home for city dwellers. “I’d say our market is 95% weekenders from the New York metro area,” says Karen Casey, a broker with William Pitt Sotheby’s Realty who has lived in the area since 1975. “We have thousands of acres that are either registered as land trust open space or state parks, so it’s really nice being in a community with so much beautiful scenery.” Kent’s identity is molded in part by three boarding schools in the area, and much of the local activity revolves around the village center, home to several local businesses and community events.
With its cozy cafés, local boutiques, and outdoor beauty, Kent makes everyday life feel like a gentle escape.
Iron Mountain Reservation brings sweeping views and quiet wooded trails to the heart of Kent.
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Historic and modern houses in low supply and high demand
Kent offers a range of houses built between the 1700s and 2000s. Availability is scarce, however. “We have more buyers than sellers, so when something comes on the market for $500,000 to $1 million, they tend to go quickly,” Casey says. Small homes on one or two acres can sell for $500,000 to $650,000, while larger houses on five or more acres range from $700,000 to over $1 million.
Alongside its modern retreats, Kent is dotted with charming colonial homes that highlight the town’s historic New England roots.
Kent’s housing mix includes a handful of sleek, contemporary builds that bring modern design to its classic New England landscape.
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Fly-fishing, hiking the Appalachian Trail and exploring Kent Falls
With the Housatonic River running right through town, Kent is flush with state parks and mountainous nature reserves. “Cornwall, which is just north of here, is known for world-class fly fishing on the Housatonic River,” says Casey. “There are people who move here just for that.” Kent Falls State Park is a popular destination for locals and tourists looking to hike up or relax under the 250-foot cascading waterfall. Macedonia Brook State Park and Pond Mountain Natural Area are other common hiking spots with nature trails. Kent also has an entry point to the Appalachian Trail, which runs more than 2,100 miles from Maine to Georgia. Nearby Lake Waramaug has two state parks and opportunities for fishing, boating and country club golfing.
Lake Waramaug State Park gives Kent a serene winter escape where visitors can enjoy peaceful ice fishing on the frozen shoreline.
The Appalachian Trail runs straight through Kent, offering forested climbs, river views, and one of its most scenic stretches in Connecticut.
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Local shops, restaurants and art galleries in the village center
Local businesses line Main Street in the village center, where century-old Colonial and Victorian-style homes have been converted into local boutiques, restaurants and art galleries. When dining out, locals can grab some pub grub on the patio at Kingsley Tavern, enjoy a blend of Mexican and American food at Villager Restaurant or head to Fife ‘n Drum for fine dining in a rustic atmosphere with rotating live piano music. 45 On Main serves coffee and homemade chocolate. For groceries, Davis IGA sells organic produce, which Casey says is in high demand for the community. “During the summer, you can travel the back roads and find lots of farm stands,” she says.
Fife ’n Drum is a beloved Kent landmark known for its fine dining, warm atmosphere, and nightly live piano music.
45 on Main brings Kent’s small‑town charm to life with handcrafted chocolates, great coffee, and a welcoming community vibe.
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Highly rated public schools and three college prep boarding schools
Kindergarten through eighth-grade students attend Kent Center School, which receives an A grade from Niche and is ranked the best public middle school and fifth-best public elementary school in Litchfield County. Housatonic Valley Regional High School, rated B-plus, is a top high school for the arts. Kent’s three boarding schools include Kent School, South Kent School and Marvelwood School. Kent (all boys) and South Kent (coed) both receive an A-plus. Marvelwood receives an A and offers a co-ed education with about 80% boarding students and 20% locals. “It’s a very sophisticated community, and that’s the culture that comes from the preparatory schools," says Casey. "They play a nice role here and want to be part of the community, not an elitist that stays across the bridge. They invite the town to different events, whether it be music, lectures or sports.”
Kent Center School is a public PK–8 school in Kent, Connecticut, serving about 191 students on its Judd Avenue campus.
South Kent School is an all‑boys boarding school set on a sprawling 650‑acre hillside campus in Kent.
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Kent Sidewalk Sale Days and holiday celebrations in the village center
Kent Sidewalk Sale Days is one of the biggest events, held the first day of August in the village center. “It’s like a festival of shoppers,” says Casey. “Everything is basically half off, and all the merchandise is put outside. It’s been a huge draw for over 30 years.” In October, people race in the scenic 5-mile Kent Pumpkin Run, some wearing costumes. Come December, the town embraces the holiday season. “The village center is gorgeous during Christmastime," says Casey. "All the businesses are lit up, mostly in white lights, and they decorate their shop windows and doors. You feel like you’re in a fairytale.”
Two hours to New York by car or train
Main Street is part of U.S. Route 7, which runs north and south through Connecticut and serves as the starting point to most destinations, including New York City, about two hours away. Commuters can also take Metro-North for a two-hour train ride into Manhattan. Other nearby cities include New Haven and Hartford, about 90 minutes away.
Written By
Nicolas Stuart
Photography Contributed By
Samantha Houtchens
Video By
Samantha Houtchens
Interested in learning more about homes in this area?
Reach out to
Gina Cavallo,
an experienced agent in this area.
GreatSchools:
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On average, homes in Kent, CT sell after 82 days on the market compared to the national average of 55 days. The median sale price for homes in Kent, CT over the last 12 months is $530,000, up 18% from the median home sale price over the previous 12 months.
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,
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
8.22 acre parcel in private and exclusive St. John's Peak subdivision of Kent! Take the winding road through this peaceful and secluded area to find your future home site! With road frontage of 75 feet, the topography of this lot is mostly level, and it gently slopes down from the approved home site to the Mauwee Brook. 2004 Perc/Soil tests on file with the health district, was previously
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
Alan O'DohertyWilliam Pitt Sotheby's Int'l
$335,000
2 Beds
2.5 Baths
1,622 Sq Ft
Close to Kent's village shops and restaurants, this well-appointed townhouse offers the ease of in-town living with the feel of a private retreat. The main level centers on a light-filled living room with fireplace that opens to a spacious deck - a natural gathering spot with long sunset views. The formal dining room connects to a separate back deck, quiet and shaded, ideal for morning coffee.
The rarest luxury is seldom the land itself. It is the time already devoted to revealing its full potential. Set amidst protected land along the coveted Kent-Sharon border, RockOak offers the uncommon advantage of beginning years ahead on the construction of a legacy estate. The completed retreat allows the property to be enjoyed immediately, while the future estate evolves. Overlooking the
138 +/- acres of open pasture, mature forest, and rare privacy in South Kent. The land offers multiple potential building sites for a country getaway, along a scenic road with sweeping, seemingly infinite views. A shared driveway crosses the lower portion of the property, providing access to Hatch Pond, great for fishing or kayaking. The upper section features an open 8-acre pasture, with an
"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
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
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
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
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
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,
FURNISHED RENTAL AVAILABLE for October 2026 @ $6,500k/month. Modern Country home filled with stylish designer furniture and art. Fabulous AAA South Kent location with expansive lawn and western exposures. 4-5 bedrooms, fabulous outdoor entertainment areas, pond and brook. Close to Lake Waramaug, Appalachian Trail, Mohawk Mtn skiing, Kent and New Preston. Not far from NYC metro north train. 90 min
This 1-bedroom, 1-bathroom apartment at 81 N Main St offers 630 square feet of living space. It is nicely renovated with new kitchen, bathroom, windows and appliances.The living room provides ample room for relaxation, while the bedroom is designed for comfort and privacy. The bathroom includes a shower tub combo and is conveniently located near the living area. The kitchen is
Available now for yearly rental. Enjoy country living in this stunning location with spectacular views and total privacy. Only 90 minutes from NYC. Do you enjoy hiking or cross country skiing? Explore the homes 142 acres. Fall foliage is right around the corner followed by ski season. Mohawk Mountain a short distance away, or ski The Berkshires in a hour. Plenty of room for family and friends who
Welcome to Your Historic Haven Awaits in Kent, CT! This charming apartment features 2 bedrooms and 1 bathroom, perfect for those seeking a cozy living space. The basement provides extra storage space, while the laundry area makes chores a breeze. Step outside to enjoy the spacious yard and relax on the patio. Located in the heart of Kent, CT, this apartment offers a peaceful retreat with easy
Immerse yourself in the charm and history of New England with this unique 2 bedroom, 1 bath apartment in Kent, Connecticut. For $1,895 per month, this duplex apartment offers a blend of historical elegance and modern amenities, making it an ideal home for those who appreciate the finer aspects of village living. Elegant Living with a Modern Twist: * Historical Charm: Celebrated as a classic
Welcome to Your Historic Haven Awaits in Kent, CT! This charming apartment features 2 bedrooms and 1 bathroom, perfect for those seeking a cozy living space. The basement provides extra storage space, while the laundry area makes chores a breeze. Step outside to enjoy the spacious yard and relax on the patio. Located in the heart of Kent, CT, this apartment offers a peaceful retreat with easy
Experience the ultimate August retreat at 16 Anderson Acres Road, a contemporary masterpiece perched in the heart of Kent. This architectural gem is designed to blur the lines between luxury and nature, offering unrivaled panoramic views that stretch for miles from nearly every room in the house. Whether you are sipping your morning coffee in the open-concept living space or unwinding by the
Situated in an idyllic location this single family rental was renovated this summer. The house has many new features including a new kitchen, bathrooms, thermostats, lighting, windows, doors, siding, roof, and garage doors. There is even an auto-on generator, full basement and attached 2 car garage. The 3 bedroom, 1 1/2 bathroom one level home is privately sited and close to beautiful Lake
Discover the perfect balance of peaceful country living and modern comfort at this renovated, partially furnished 3-bedroom, 2-bathroom home, offering approximately 1,550+ square feet of thoughtfully designed living space. Nestled along one of Kent's most scenic country roads on sought-after Skiff Mountain, this inviting residence provides a private retreat surrounded by nature while remaining
Available 9/10/26 - 5/31/27 at $8,500 per month. Inquire about custom terms, more time, summer 2027 or annual terms. Inquire for details about use of Luxury pontoon boat for cruising and waterskiing. Enjoy this chic and renovated home on glamorous Lake Waramaug. Walk across the street to the fabulous dock with spacious lake side lawn. Canoe is available for use. 6 bedrooms (3 en-suite) with
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