$775,939Average Value$394Average Price per Sq Ft4Homes 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
Rudy Pierre,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Kent, CT sell after 87 days on the market compared to the national average of 53 days. The median sale price for homes in Kent, CT over the last 12 months is $515,000, up 12% from the median home sale price over the previous 12 months.
A charming brook tumbles through this easy and slightly elevated wooded parcel with considerable road frontage in the quiet Westwoods Neighborhood. Located across from a large beaver pond to which the property's brook flows and where wildlife abounds, the setting is perfect to build one's dream house and enjoy all of what nature has in store in the North West Corner of Connecticut. This parcel
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
Private 7.14 acres of beautiful scenic land, located on quiet country rd in the South Kent area, this magnificent lot offers a level site set among a mature forest and stonewalls. Located minutes from Kent Center, New Preston, and Lake Waramoug.
"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
Exceptional opportunity in desirable South Kent. This four-bedroom Colonial offers beautiful views and a spacious, light-filled layout. The main level features an inviting kitchen with an island, seamlessly connected to the living and dining room anchored by a cozy fireplace. Two sets of French doors lead to a sunroom addition, perfect for relaxing or entertaining. The main level also includes a
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
Approximately 5.5 acres in south Kent. This is a top location abutting major estates and just minutes to the state beach at Lake Waramaug and the Lake Waramaug County Club (beach, tennis, golf, clubhouse dining). This property is equi-distant between the charming villages of Kent, New Preston and Washington. Bring your architect and build your dream. 1 hour 45 minutes to NYC. Offer is subject to
Gorham Mountain property ready for your dream home! Over 6 acres in a Private setting with mature trees and an amazing location. We have different plans available and can price out a build of your choice.
Private Estate with Panoramic Views in Coveted Kent Hollow. Tucked at the end of a quiet country lane, this rare 15+ acre estate offers stunning views, complete privacy, and timeless New England charm. Perfectly perched to overlook the beauty of Kent Hollow, the property blends refined living with the tranquility of nature. The 4-bedroom, 4 bath (2 Full, 2 Half) main residence is designed for
Beautiful mountain top lot overlooking the Berkshires! This almost 7 acre lot in a private setting on the mountain top cul-de-sac is ready for your dream home. No wetlands and endless views. We have several architectural plans as well as other ideas for a build. We can also price out a full build of your choice.
Overlooking neighboring pastureland and set on 5+ private acres with a small pond, this three-bedroom cottage is rich in charm and character. A gracious foyer welcomes you into a sitting room with fireplace and built-ins, and an adjacent formal dining room framed by handsome casement windows. The spacious kitchen offers a center island and sunny breakfast area, opening seamlessly to an outdoor
FURNISHED RENTAL AVAILABLE for academic term or annual @ $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
Discover the ultimate summer retreat in the heart of the Litchfield Hills. Escape this Summer to a stunning modern home offering breathtaking mountain views, a sparkling pool, and complete privacy. The main level boasts an open-concept living, dining, and kitchen area, highlighted by a dramatic two-story wall of glass that frames the spectacular scenery. The spacious primary suite features a cozy
This recently remodeled 3 bedroom, 1.5 bath ranch is set in the rolling hills of Kent and offers sweeping mountain views. Enter through the spacious mudroom equipped with a washer/dryer and half bath. Sitting adjacent is a beautiful room with brick floors and vaulted ceilings, providing a perfect space for a family room, home office, or creative studio. The kitchen has been completely refreshed
Charming craftsman-style cottage set on 4.5 acres in the beautiful Kent Hollow area, featuring mountain views and a nearby brook, along a quiet country road. The home offers a cozy living area, an eat-in kitchen, a first-floor bedroom, full bath, and a dedicated laundry space with washer and dryer. Recently updated with fresh paint , the cottage connects to the main residence through a shared
TIME TO PLAN YOUR SUMMER VACATION! Enjoy country living in this stunning location with spectacular views and total privacy. Only 90 minutes from NYC. Swim in the heated gunfire pool. Explore the homes 142 acres. Plenty of room for family and friends who want to experience the beauty of Litchfield County. There is a 6 Bedroom main house with a 2 bedroom plus loft guest house. Total 8 Bedrooms and
Experience the ultimate country retreat with this charming, fully furnished 3-bedroom, 3-bathroom cottage set on 13+ private acres. Available for the Academic year or Winter rental, this inviting property features a heated saltwater gunite pool, a separate guest cottage, beautifully maintained grounds, and perennial gardens. The main residence boasts a sun-filled kitchen with an eat-in area, a
Experience the ultimate country retreat with this charming, fully furnished 3-bedroom, 3-bathroom cottage set on 13+ private acres. Available for the Academic year or Winter rental, this inviting property features a heated saltwater gunite pool, a separate guest cottage, beautifully maintained grounds, and perennial gardens. The main residence boasts a sun-filled kitchen with an eat-in area, a
Available May 15 - Sept 15, 2026 at $19,500 a month. Inquire about custom terms, more time 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 plenty of room
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