Moving to Roxbury CT | real estate for sale in Roxbury Connecticut | Property Statistics of living in Roxbury
Roxbury is one of Connecticut's most exclusive residential communities, known for luxury estates, large parcels, and exceptional privacy. The town has long attracted prominent business leaders, artists, and high-net-worth individuals. Real estate values are among the highest in the county due to limited inventory and sustained demand for premium properties. Strict zoning and preservation efforts help protect long-term market desirability.
286 South Street
Roxbury, Connecticut 06783
$995,000 | Under Contract - Continue
5 Beds | 5 Baths | 2804 Sqft | 8.4 Acres | 419 Days on Market
Property Type: Single Family For Sale
Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main...
38 Mountain Lane
Roxbury, Connecticut 06783
$760,000 | Active
3 Beds | 3 Baths | 2336 Sqft | 4.96 Acres | 276 Days on Market
Property Type: Single Family For Sale
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 ceili...
23 Painter Hill Road
Roxbury, Connecticut 06783
$1,049,000 | Active
4 Beds | 3 Baths | 1782 Sqft | 3 Acres | 68 Days on Market
Property Type: Single Family For Sale
Mint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. New Anderson Luxe White Oak Windows. Wood-Burning Fireplace, Vaulted Primary Bedroom with Balcony and Private Bath. Dine or relax on the Flagstone Terrace. Must...
33 Sentry Hill Road
Roxbury, Connecticut 06783
$1,549,000 | Active
4 Beds | 4 Baths | 2716 Sqft | 3.01 Acres | 103 Days on Market
Property Type: Single Family For Sale
Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Mooseho...
18 Tunnel Road
Roxbury, Connecticut 06783
$1,025,000 | Active
3 Beds | 3 Baths | 2080 Sqft | 3.1 Acres | 104 Days on Market
Property Type: Single Family For Sale
MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round Spa Pool -- all on the best rural Roxbury scenic dirt road with walking area along the Shepaug River and nearby historic farmhouses and land preserve. All minut...
137 Davenport Road
Roxbury, Connecticut 06783
$950,000 | Active
3 Beds | 2 Baths | 1614 Sqft | 2.27 Acres | 65 Days on Market
Property Type: Single Family For Sale
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...
233 Southbury Road
Roxbury, Connecticut 06783
$1,795,000 | Active
5 Beds | 6 Baths | 5447 Sqft | 10.05 Acres | 7 Days on Market
Property Type: Single Family For Sale
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 ...
268 South Street
Roxbury, Connecticut 06783
$3,600,000 | Active
5 Beds | 5 Baths | 6190 Sqft | 41 Acres | 12 Days on Market
Property Type: Single Family For Sale
Quintessential Litchfield County Estate on 41+/- acres. Restored 1850s 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...
1030 Washington Woodbury Road
Roxbury, Connecticut 06783
$1,949,000 | Active
4 Beds | 5 Baths | 4874 Sqft | 18.62 Acres | 189 Days on Market
Property Type: Single Family For Sale
NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers scale, privacy, and the relaxed elegance that defines Litchfield County living. Designed for both comfortable daily living and effortless entertaining, the home opens to expansive grounds, a ...
18 Ranney Hill Road
Roxbury, Connecticut 06783
$1,895,000 | Active
4 Beds | 4 Baths | 3198 Sqft | 5.42 Acres | 60 Days on Market
Property Type: Single Family For Sale
Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard plant...
336 South Street
Roxbury, Connecticut 06783
$1,025,000 | Active
4 Beds | 3 Baths | 2556 Sqft | 4.33 Acres | 76 Days on Market
Property Type: Single Family For Sale
Beautiful 4 bedroom, 2.5-bath Colonial set on a picturesque, park-like property in desirable southern Roxbury. A dramatic two-story foyer welcomes you into a thoughtfully designed layout featuring a formal dining room, a spacious living room with custom built-in bookshelves, and ...
8 Bayberry Hill
Roxbury, Connecticut 06783
$3,650,000 | Under Contract - Continue
5 Beds | 6 Baths | 5940 Sqft | 31.77 Acres | 434 Days on Market
Property Type: Single Family For Sale
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 Librar...
4 Judge Road
Roxbury, Connecticut 06783
$3,200,000 | Active
3 Beds | 2 Baths | 1974 Sqft | 23 Acres | 19 Days on Market
Property Type: Single Family For Sale
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 kit...
31 Hickory Lane
Roxbury, Connecticut 06783
$1,685,000 | Under Contract
4 Beds | 5 Baths | 6169 Sqft | 8.84 Acres | 213 Days on Market
Property Type: Single Family For Sale
This special home is located in one of Roxburys most desirable neighborhoods on a quiet dead end road. A long, winding & very private driveway leads up to the commanding double-story porticoed entrance. The traditional colonial layout includes a central chefs kitchen which rests ...
24 Hickory Lane
Roxbury, Connecticut 06783
$1,099,000 | Active
4 Beds | 4 Baths | 3340 Sqft | 3.01 Acres | 103 Days on Market
Property Type: Single Family For Sale
Tucked away at the end of a quiet cul-de-sac in one of Roxburys 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 firepla...
216 Baker Road
Roxbury, Connecticut 06783
$679,000 | Active
4 Beds | 2 Baths | 2008 Sqft | 0.85 Acres | 103 Days on Market
Property Type: Single Family For Sale
Step back in time with this historic 1800s Colonial that retains its original character and charm while offering modern amenities, including an updated kitchen and bathrooms. The home features four bedrooms upstairs with wood floors, including a primary bedroom with an attached r...
188 Bacon Road
Roxbury, Connecticut 06783
$618,000 | Active
2 Beds | 2 Baths | 1192 Sqft | 4.87 Acres | 25 Days on Market
Property Type: Single Family For Sale
Chic Country Cabin in Bucolic Litchfield County. Escape to your own peaceful retreat offering the perfect blend of comfort, character, and privacy on nearly 5 acres of wooded wonderland. This home has lots of character and a flexible layout with 2 bedrooms, 2 full bathrooms plus ...
176 Apple Lane
Roxbury, Connecticut 06783
$1,995,000 | Under Contract
4 Beds | 5 Baths | 3566 Sqft | 4.24 Acres | 32 Days on Market
Property Type: Single Family For Sale
Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manicured acres with a resortlevel pool, just far enough from the city to exhale, yet close enough to make spontaneous weekend getaways a reality. From the moment you arrive, this summer ready pr...
137 Davenport Road
Roxbury, Connecticut 06783
$475,000 | Under Contract
3 Beds | 2 Baths | 1614 Sqft | 2.27 Acres | 31 Days on Market
Property Type: Single Family For Sale
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 features a new roof, furnace, water heat...
47 South Street
Roxbury, Connecticut 06783
$850,000 | Active
3 Beds | 2 Baths | 2489 Sqft | 4.47 Acres | 28 Days on Market
Property Type: Single Family For Sale
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 opportunit...
28 Garnet Road
Roxbury, Connecticut 06783
$1,000,000 | Active
3 Beds | 4 Baths | 3696 Sqft | 3.44 Acres | 67 Days on Market
Property Type: Single Family For Sale
Discover modern serenity in this private contemporary retreat nestled on 3.44 private acres. The ascending driveway assures a sense of quiet and seclusion, leading you to a home bathed in natural light from a soaring two-story wall of south-facing windows, this home perfectly ble...
246 North Street
Roxbury, Connecticut 06783
$1,095,000 | Active
3 Beds | 2 Baths | 2031 Sqft | 3.21 Acres | 65 Days on Market
Property Type: Single Family For Sale
Juniper Hill offers masterfully updated one level living in Roxbury, Connecticut. Dubbed 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 ...
242 Tophet Road
Roxbury, Connecticut 06783
$799,000 | Under Contract
3 Beds | 2 Baths | 1862 Sqft | 6.07 Acres | 150 Days on Market
Property Type: Single Family For Sale
Nestled within one of Roxbury, Connecticuts 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 pe...
94 Judds Bridge Road
Roxbury, Connecticut 06783
$796,783 | Active
2 Beds | 2 Baths | 1990 Sqft | 8.7 Acres | 51 Days on Market
Property Type: Single Family For Sale
Once in a blue moon, an opportunity arises on one of Roxburys most iconic and sought-after country roads. Nestled in the heart of the exquisite, serene Mine Hill Preserve area, this remarkable property offers nearly nine acres of mature woods, rolling lawns, rock outcroppings, an...
45 Chalybes Road
Roxbury, Connecticut 06783
$995,000 | Active
3 Beds | 4 Baths | 2725 Sqft | 2.97 Acres | 117 Days on Market
Property Type: Single Family For Sale
Light-filled, modern living on a private nearly 3-acre corner lot - with room to grow. Set on a beautifully positioned corner parcel, this fully renovated home is defined by natural light and flexibility. Expansive windows and vaulted ceilings create a bright, open feel throughou...
50 Southbury Road
Roxbury, Connecticut 06783
$725,000 | Active
5 Beds | 3 Baths | 1365 Sqft | 2 Acres | 48 Days on Market
Property Type: Single Family For Sale
Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character...
47 Squire Road
Roxbury, Connecticut 06783
$3,995,000 | Active
5 Beds | 6 Baths | 7121 Sqft | 8.03 Acres | 51 Days on Market
Property Type: Single Family For Sale
A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jacks Brook and a land trust on two sides, providing a serene and secluded environmen...
2 Pickett Road
Roxbury, Connecticut 06783
$1,799,000 | Active
5 Beds | 5 Baths | 3326 Sqft | 8.35 Acres | 60 Days on Market
Property Type: Single Family For Sale
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, highl...
20 Wellers Bridge Road
Roxbury, Connecticut 06783
$725,000 | Active
3 Beds | 3 Baths | 2059 Sqft | 1.33 Acres | 53 Days on Market
Property Type: Single Family For Sale
This handsome 1820s Colonial, set behind large shade trees on 1.33 acres just off the Green, is an easy walk to the Library, Booth School, Apple Lane Park, Churches, Tennis courts, and a morning cuppa at the Roxbury Market. Major renovation in 2018 included New HVAC, New wiring, ...
56 Goldmine Road
Roxbury, Connecticut 06783
$1,375,000 | Under Contract
3 Beds | 3 Baths | 2620 Sqft | 0.98 Acres | 17 Days on Market
Property Type: Single Family For Sale
This cross gabled farmhouse was built in 2006 by its artisan craftsman owner, expanding upon the original foundation of a dwelling previously occupied by the caretaker of Arthur Millers residence. The home was designed to leverage distant views east that stretch across thousands ...
11 Ravenrock Road
Roxbury, Connecticut 06783
$3,395,000 | Active
4 Beds | 6 Baths | 7063 Sqft | 20.11 Acres | 610 Days on Market
Property Type: Single Family For Sale
A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in the beautiful Litchfield Hills with spectacular views that go on for miles. This property includes a four bedroom, five and a half bath main residence, in ground heated Gunite pool, tennis co...
25 Highmeadow Lane
Roxbury, Connecticut 06783
$1,795,000 | Active
4 Beds | 4 Baths | 4310 Sqft | 17.31 Acres | 67 Days on Market
Property Type: Single Family For Sale
Sprawling 4-bedroom colonial as part of a peaceful and private 17-acre estate in desirable Roxbury, CT. Sighted well on open rolling lawns with sweeping sunrise/sunset views, this property offers country living with exceptional versatility. The sun-filled eat-in kitchen features ...
380 Southbury Road
Roxbury, Connecticut 06783
$1,550,000 | Active
4 Beds | 5 Baths | 4452 Sqft | 6.87 Acres | 109 Days on Market
Property Type: Single Family For Sale
Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramat...
16 Jonathan Drive
Roxbury, Connecticut 06783
$950,000 | Active
3 Beds | 3 Baths | 2028 Sqft | 2.29 Acres | 154 Days on Market
Property Type: Single Family For Sale
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 center...
220 Painter Hill Road
Roxbury, Connecticut 06783
$2,895,000 | Active
4 Beds | 5 Baths | 4570 Sqft | 4.68 Acres | 89 Days on Market
Property Type: Single Family For Sale
Perched atop Painter Hill-Roxburys 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 ...
99 Carriage Lane
Roxbury, Connecticut 06783
$1,495,000 | Active
4 Beds | 3 Baths | 6395 Sqft | 3.79 Acres | 324 Days on Market
Property Type: Single Family For Sale
Looking to escape the hectic pace of city life? Welcome to this peaceful, beautifully renovated 4-bedroom home, originally built in 2005, offering the perfect blend of comfort and tranquility. Featuring 2.5 baths and a spacious open-concept living and dining area, this home is id...
179 South Street
Roxbury, Connecticut 06783
$985,000 | Active
3 Beds | 2 Baths | 1772 Sqft | 12.74 Acres | 121 Days on Market
Property Type: Single Family For Sale
Own a Piece of Roxbury History! One of Roxburys three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangi...
11 Evergreen Drive
Roxbury, Connecticut 06783
$1,200,000 | Active
4 Beds | 4 Baths | 3800 Sqft | 3.39 Acres | 151 Days on Market
Property Type: Single Family For Sale
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 ...