$1,219,010Average Value$500Average Price per Sq Ft18Homes 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
Marian Van Egas,
an experienced agent in this area.
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On average, homes in Roxbury, CT sell after 142 days on the market compared to the national average of 54 days. The median sale price for homes in Roxbury, CT over the last 12 months is $1,400,000, up 15% from the median home sale price over the previous 12 months.
A colonial antique home on a level scenic lot in sought-after Litchfield County. As you enter through the front door, you're welcomed by an original staircase & hickory wood floors. The living room features an exposed wood beam, a fireplace & hickory flooring. A formal dining room with classic pine floors & french doors that lead to a 4 season room. The 4 season room features a wood-burning
Modern Sophistication in Roxbury. Superbly re-imagined and meticulously renovated in 2024, this turn-key home sits on nearly 3 private acres. Completely transformed with high-end finishes and energy-efficient upgrades, the home offers the ultimate floor plan with two first-floor ensuite options and close proximity to Roxbury Market, town tennis courts and Hurlburt Park. Inside, a dramatic great
A colonial antique home on a level scenic lot in sought-after Litchfield County. As you enter through the front door, you're welcomed by an original staircase & hickory wood floors. The living room features an exposed wood beam, a fireplace & hickory flooring. A formal dining room with classic pine floors & french doors that lead to a 4 season room. The 4 season room features a wood-burning
Prime Roxbury Location. Nestled off a picturesque classic country lane, flanked by distinguished residences and just minutes from the vibrant heart of Roxbury Center, awaits an exceptional opportunity. This approved building parcel is primed for complete development, offering a level to gently sloping terrain within a private and serene setting. Imagine crafting your ideal retreat amidst the
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 of Roxbury's natural beauty and recreational amenities, with the lot located just minutes from the
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
Modern Sophistication in Roxbury. Superbly re-imagined and meticulously renovated in 2024, this turn-key home sits on nearly 3 private acres. Completely transformed with high-end finishes and energy-efficient upgrades, the home offers the ultimate floor plan with two first-floor ensuite options and close proximity to Roxbury Market, town tennis courts and Hurlburt Park. Inside, a dramatic great
This is a wonderful well cared for country home in the beautiful small town of Roxbury. Situated on this dead end road you are minutes to local amenities. Take advantage of nearby hiking trails, parks and open space with Southbury, Bridgewater, Washington and Woodbury town centers just a short drive away. Only 90 minutes from NYC. The first floor has two fireplaces and is open and spacious with
Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene
Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand
This is 'the best deal in Roxbury"! New construction on 3.39 acre lot. The style is a classic farmhouse design Cape with a covered front porch with metal roof. There will be 9' ceiling height on the main level and 8' on the upper level. Both levels will have wood floors. The primary suite is on the main level with a large bath including a shower a free standing tub and a walk in closet. The
Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft Colonial Offers Panoramic Sunset Views and Exceptional Privacy. Graciously Proportioned Rooms Populate the Main Level & Include: a Vaulted-Ceiling Living Room with Fireplace, Paneled Library, Inviting Family Room, and a Spacious Eat-in Kitchen with Top-tier Appliances. The Refined Primary Suite Features a
Build your dream on this designated "Scenic Road" abutting spectacular land trust trails. The lot consists of 24.8+/- acres, with a 9+/- acre building envelop. The building site is to be accessed from a future driveway running at the South border, along the Land Trust access point. The lightly wooded property rises to an 820-foot elevation and is resplendent with mature trees, ferns, moss and
Good Hope Estate. Transport yourself to this stunning European-style home with all the bells and whistles! The well thought out 4 bedroom, 4.5 bath home with seasonal views sits on 18 acres of privacy and nature! The eat-in kitchen is a chef's dream complete with Sub-Zero, Dacor range, granite countertops and double farm sink. Plus a separate pantry to go with it. Adjacent is a cozy area with
FURNISHED RENTAL AVAILABLE SEPT 2, 2025- MAY 2026 @ $2,500/MONTH. Spacious one bedroom apartment above garage on large, private estate. Clean, updated and comfortable. Bright living room with built ins and mini bar. Dining room and kitchen. Stackable washer/dryer in unit. Excellent credit, references and application required. Electricity included. Oil heat paid for by tenant.
Recently renovated single-family home on the Woodbury/Roxbury town line. Completely rebuilt from the studs up, this three-bedroom ranch features brand-new electrical, HVAC, spray-foam insulation, trim, drywall, hardwood floors, plus a new kitchen and three new baths. Rare opportunity to rent a truly "like-new" home available immediately. Enjoy a spacious main level with three bedrooms, a living
Available Month of August through Labor Day at $25k. Spend a perfect summer month in this Gorgeous Connecticut Antique "Edson Bradley Estate," beautifully updated 3 bedroom antique home, with an additional 1 bedroom guest suite in the nearby renovated barn, a gunite pool with views west, apple orchard and a lovely park-like setting. The 3 bedroom home main house offers open kitchen to
Available @ $35K for August 6-Sept 7, 2026. Also avail $15,000/mo for school year 2026/2027. Gunite Heated Pool being installed in April 2026 and will be ready for August tenant. Enjoy Modern Luxury in Connecticut's Countryside. The meticulously renovated 4-bedroom residence seamlessly blends the original mid-century architecture with contemporary sophistication. Enter on the main level with 2
Escape to the country and spend your Spring & Summer in Connecticut's spectacular Litchfield County! Spend your mornings sipping coffee and viewing the sunrise from the front porch, and evenings with sunsets on the back deck. This centrally located, hilltop, 3 bedroom, 2 & 1/2 bath home is bright & open - soaring ceilings and open floor-plan brings everyone together. Main level primary suite has
Available May 2026: $2,200 plus utilities per month. 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 1 bedroom/1 bath apartment, is located beneath the main house and may be rented with the main house(Upstairs 3-bedroom) or completely
Whole House Now available from May 2026 at $6,000. 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 4-bedroom, 3 bath home rests on five acres with a gentle stream running through it. State of the art chef's kitchen with all new appliances
Summer 2026: July and/or August at $20,000 per month. Inquire for alternate dates. 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
Mid-Century single-level in a convenient Roxbury location. Cool mad-men vibe with floor to ceiling windows, exposed beams, vaulted ceilings, stone and wood floors, and wood paneling. Throughout the house the many windows pour natural light in and give fabulous views over the private and manicured grounds. The home has multiple versatile rooms giving a choice of layout to fit your needs. The
Available Sept 2026 - May 2027 @ $15,000/mo and $35,000 for August 2026. Enjoy Modern Luxury in Connecticut's Countryside. New Gunite heated pool being installed April 2026. This meticulously renovated 4-bedroom residence seamlessly blends the original mid century architecture with contemporary sophistication. Enter on the main level with 2 bedrooms and 2 full baths, sauna, foyer, powder room and
Available March 2-May 31, 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
Charming barn-style home on 15.27 acres off quiet country road. Four bedrooms and two and one half baths. Open floor plan. Exposed timber. Double sided stone fireplace. French doors to rear patio. In ground pool and barrel sauna. The perfect summer retreat in the beautiful town of Roxbury. Available short term between September to May for $7,500 per month. Contact agent for availability. Just 90
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