$1,197,731Average Value$488Average Price per Sq Ft30Homes For Sale
A rural lifestyle with nearby urban amenities
Just a few miles east of Bridgeport, in western Connecticut's Litchfield Hills, sits the town of Roxbury, a rural area spread over 27 square miles with a population just over 2,000. That low population density means that residents here can appear somewhat isolated from the creature comforts associated with urban living, but that’s exactly how they like it. “People move to Roxbury because it’s quiet,” says local Realtor Stephanie Blake of Realty ONE Group Connect. “The rural nature of the town is its real appeal. At the same time, though, it’s close to Woodbury and Bridgewater and other places that have a lot more going on.”
The great outdoors
The vast majority of land in Roxbury is undeveloped, so residents here don’t have to travel far to experience natural beauty. When they’re looking for a park, residents can head to Hurlburt Park, with a playground, covered picnic pavilion and plenty of open space. Hurlburt Park is also the site of the annual Roxbury Pickin’ and Fiddlin’ Contest, where musicians of all ages compete for cash prizes in different categories. Another favorite spot for outdoor activities is the River Road Preserve, a 57-acre parcel of hemlock forest bordering the Shepaug River. Visitors to the preserve can hike the 1.5-mile trail, stop for a picnic at one of the designated areas in the area or fly-fish the scenic river.
Locals can use exercise equipment at Hurlburt Park in Roxbury.
River Road Preserve is a beautiful place for a hike in Roxbury.
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History, culture and a few spirits, too
With a history dating back to Colonial times, Roxbury also offers plenty of opportunities for history buffs to learn more about the region, with historic sites that Realtor Vinnie Diana from William Raveis Real Estate describes as “really cool places to check out.” Mine Hill Preserve is the site of a 19th-century iron-making complex, and includes the remnants of the original roasting ovens and blast furnace used in the processing of iron ore. A self-guided tour includes signs detailing the iron processing procedure and the story of granite quarrying at the site, including the stone used in the construction of the Brooklyn Bridge and Grand Central Station in New York City. Visitors to the preserve can also take advantage of the extensive network of hiking trails that cover 6 miles through the preserve’s 360 acres.
Adjacent to Mine Hill Preserve is the Kelsey Museum and Sculpture Garden, featuring 165 original works by renowned sculptor Sterett-Gittings Kelsey, who was declared “the new master of movement” by Yale University Professor of Sculpture Erwin Hauer. Next door to the museum is the Mine Hill Distillery, with operations housed in various historic 19th-century buildings. Visitors can sample a variety of spirits distilled on the premises and tour the grounds to learn more about how spirits are made.
You will find old furnace equipment and great history at Mine Hill Preserve in Roxbury.
The Mine Hill Distillery in Roxbury produces its own bourbon, gin, and vodka.
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Homes from the 18th century to today
“Because most of the price points in Roxbury are a little higher, paired with the fact that it is a quiet town, the average buyer in the area tends to be older and more established,” says Blake. The median price of real estate in Roxbury is $1.15 million, and buyers should expect to pay an average of $490 per square foot. A three-bedroom/two-bathroom raised ranch-style home can sell for $500,000, and prices can go up to $3.25 million for a three-bedroom/four-bathroom Colonial home built in 1792 and formerly owned by legendary Broadway composer Stephen Sondheim. Regardless of price, buyers can expect to find homes situated on typically larger lots with abundant mature trees.
You will find beautiful 18th century Colonial homes in Roxbury.
You will also find homes tucked away from the road on relaxing settings in Roxbury.
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School is in session
Roxbury is districted to Regional School District Number 12, which earns an overall rating of A from Niche. Students here can attend Booth Free School through fifth grade, then Shepaug Valley School for grades 6-12. Booth earns an A from Niche and Shepaug Valley earns an A-minus. High schoolers at Shapaug Valley School can participate in over 35 different school-sponsored clubs, and they have the opportunity to play more than 20 varsity-level sports. There are also several excellent private schools in the area, including nearby Kent School, which earns an A-plus rating from Niche.
Roxbury students can attend Booth Free School, rated A by Niche, through the fifth grade.
Students from Roxbury then go to Shepaug Valley School for sixth through twelfth grade.
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Eat here, shop there
Because of its rural setting, Roxbury does not lay claim to being a hub of commercial activity. As a result, residents do need to have to travel a little in order to do most of their shopping. That said, the Roxbury Market & Deli is located in town, providing a gathering spot for area residents to buy groceries and sit down for a meal. Serving breakfast, lunch and dinner – as well as ice cream from the Ferris Acres Creamery in Newtown, Connecticut – the Roxbury Market & Deli has hosted such luminaries as Marilyn Monroe, Dustin Hoffman and Daniel Day-Lewis.
More in-depth shopping requires residents to make the 20-mile trip to Waterbury, where multiple shopping centers provide access to a range of national retailers. Those seeking a more intimate shopping experience are in luck, too. Tucked into a small enclave off Highway 47 in Woodbury is The Hidden Acorn, an antique store selling vintage home goods, accessories and furniture, where shoppers can find unexpected treasures for bargain prices. And if the shopping bug hits extra hard, the glitz and glamour of New York City are two hours away by train from the Danbury station, less than 20 miles south of Roxbury.
Roxbury Market & Deli in Roxbury is the most popular option in town for lunch.
Bridgewater Market is a few minutes from Roxbury but always worth the trip.
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Written By
Andrew Spencer
Photography Contributed By
Jerome Strauss
Video By
Edward Pokoj
Interested in learning more about homes in this area?
Reach out to
Robert Leonard,
an experienced agent in this area.
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On average, homes in Roxbury, CT sell after 133 days on the market compared to the national average of 56 days. The median sale price for homes in Roxbury, CT over the last 12 months is $1,400,000, up 14% from the median home sale price over the previous 12 months.
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
Completely reimagined from top to bottom, 22 E. Woods Rd. is a home where elevated design meets everyday comfort. From the moment you step inside, gleaming hardwood floors, abundant natural light, and an inviting open floor plan create a warm and welcoming atmosphere that feels equally suited to quiet mornings and lively gatherings. At the heart of the home is a stunning custom kitchen featuring
Well maintained and updated Raised Ranch 3 bedroom 1.5 bathrooms home ready to move in! Open concept living room/dining room and kitchen that opens on to a gorgeous 12'x30' deck overlooking a beautiful fenced in backyard in the woods make for a very private setting. This home has all new windows, a newly updated kitchen with stainless steel appliances and granite countertops, finished lower-level
Step back in time and own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic
Presenting a truly rare opportunity for BRAND NEW CONSTRUCTION in Roxbury, CT, this luxury residence offers approximately 3,300+ SF of meticulously designed living space, including a spacious finished basement & attached double garage. Enjoy exquisite finishes throughout, highlighted by 6" white oak hardwood flooring, custom architectural millwork and decorative shiplap details. The gourmet
Exceptional equestrian estate featuring a fully equipped horse facility and charming Cape-style home. Ideal for equestrians, trainers, or boarding professionals, the property offers 16 rubber-matted stalls, a large well-lit indoor arena, and a second-floor viewing lounge with kitchen amenities-perfect for lessons, clinics, and entertaining. The barn includes a wash stall, feed room, hay storage,
Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece,
Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and
INCREDIBLE OPPORTUNITY TO OWN IN THE PAINTER HILL RD AREA OF ROXBURY! This 1,600 sq ft, 3-bedroom, 2-bathroom Ranch home with a 2-car garage sits on a sun-filled, gently sloping lot with tremendous potential for the new Homeowner. The home will be a Complete REMODEL with Separate Driveway. . The septic was last pumped September 2025, and annual taxes are just $3,851. Renovation by Design Builders
ENGINEERING and DRIVEWAY APPROVED! THERE ARE LOTS AND THEN THERE ARE MAGICAL, SPECIAL, UNPARALLELED LOTS, STEEPED IN HISTORY WHERE YOU CAN ACTUALLY FEEL AND HEAR THE TERRAIN SINGING TO YOU. THE WOODS ROXBURY IS SUCH A PLACE AS EVIDENCED BY OUR RECENT SALES. THIS IS THE LAST AVAILABLE LOT FROM PHASE II, (LOT #1) AND IT MUST BE SEEN AND HEARD TO UNDERSTAND HOW YOUR FUTURE HEIRLOOM HOME WILL BE
Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite
Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room.
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
Private, Rural setting within a short walk to Roxbury Tennis courts, library and the Roxbury Market.This 4.01 acre approved building lot offers the perfect blend of tranquility and convenience, making it an exceptional opportunity to create your custom dream home. Tucked away on a quiet road, this property features beautiful, light woods that provide a serene and private setting. Enjoy the best
Juniper Hill offers masterfully upgraded one level living in Roxbury, Connecticut. Called a "Little Gem on the Hill" in Country Home, this unassuming ranch has been elevated with chic, yet family friendly styling. Modern comforts combine with country character in a home situated on compelling terrain. Large, level yard and play area that is difficult to find at this price point in the Litchfield
NEW PRICE Summer 2026: July and/or August at $16,500 per month. Quintessential Litchfield County Retreat with Fabulous Gunite Pool in the Heart of the Town of Roxbury on 4 +/- pastoral acres. 4 bedroom and 2 and 1/2 bath charming Colonial with Great Room/Family Room with vaulted ceilings, Eat-in Country Kitchen, Formal Living Room with wood-burning fireplace, Formal Dining Room and a Wonderful
Melinda DubowKlemm Real Estate Inc
$24,900 per month
3 Beds
2.5 Baths
2,080 Sq Ft
Meander down the most scenic of Roxbury dirt roads to reach "Tunnel Road 4-BR" tucked between the Shepaug River, historic wood Judd's Bridge and Farm and 1000 acres of Steep Rock land trust with endless hiking trails. Pristine renovated private country home with year round 8'x 16' spa pool, wood burning fireplace and open floor plan. Dine or relax on the granite terrace or covered front porch.
Peter KlemmKlemm Real Estate Inc
$8,500 per month
3 Beds
3.5 Baths
3,389 Sq Ft
Oct-May Rental. Newly Renovated & Exquisitely Appointed Barn House. Set Along a Very Low Traveled Unpaved Town Road, This is a Very Chic & Sophisticated 3Bedroom, 3.5 Bath Retreat Including: A Main Level Primary Bedroom with Fireplace & New Full Bath. Wonderful Public Rooms Include: Large Living Room with Vaulted Ceiling, Fireplace & Antique Beams; Formal Dining Room & A Timeless Eat-in Kitchen
Upper 3-bedroom, 2-bath now available from 8/1/26 @ $4,500 for August, 9/'26 Academic/Annual @ $3,500. Featured in CTC & G January 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 3-bedroom, 2 bath home rests on five acres with a gentle stream running through it.
Available Oct 1, 2026 @ $15,000/mo. Perched high on a scenic Roxbury hillside, this new 3-bedroom home represents true luxury living. The architecture seamlessly integrates nature and light with huge walls of windows with retractable screens. The 2 embedded James Turrell light sculptures transform the living experience into an ever-changing meditation on color and space. The open floor plan
Perfect 6BR 3.5 Bath home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT. Home to actors, writers, artists and the owners of luxury estate vacation homes. Many world class restaurants, inns
Pristine hilltop art filled home with views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. Wood burning fireplace, vaulted master bedroom with balcony and private bath. Dine or relax on the flagstone terrace. Ping pong, trampoline, croquet, badminton, gas BBQ, fire pit, bikes and board games. SUMMER June - August $18,900/month; OFF-SEASON September -
Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.
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