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.
21 Carriage Lane
Roxbury, Connecticut 06783
$589,990 | Active
3 Beds | 3 Baths | 1248 Sqft | 3.2 Acres | 0 Days on Market
Property Type: Single Family For Sale
Coming Soon! A former artist retreat is waiting for you! This Ranch/Rambler style home boasts an open concept with vaulted ceilings. Enjoy all the privacy that Roxbury and the Litchfield Hills offers, yet have convenient access to major highways. The home offers 3 bedrooms and 3 ...
188 Bacon Road
Roxbury, Connecticut 06783
$575,000 | Active
2 Beds | 2 Baths | 1192 Sqft | 4.87 Acres | 62 Days on Market
Property Type: Single Family For Sale
Best Litchfield County Opportunity! Escape to your own peaceful country retreat with the perfect blend of comfort, character, and privacy on nearly 5 acres of wooded wonderland. Less than 2 hours from NYC, this home has lots of character and a flexible layout with 2 bedrooms, 2 f...
28 Garnet Road
Roxbury, Connecticut 06783
$950,000 | Active
3 Beds | 4 Baths | 3696 Sqft | 3.44 Acres | 100 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...
90 Mallory Road
Roxbury, Connecticut 06783
$575,000 | Active
3 Beds | 3 Baths | 2282 Sqft | 3.56 Acres | 6 Days on Market
Property Type: Single Family For Sale
Diamond in the rough! This solid and expansive home is waiting for its new life, with you as the steward. It has 3 good sized bedrooms, a bonus room off the primary (which is ensuite), a large partially finished lower level, perfect for a game room, gym, man or woman cave, an ope...
33 Sentry Hill Road
Roxbury, Connecticut 06783
$1,499,000 | Active
4 Beds | 4 Baths | 2716 Sqft | 3.01 Acres | 140 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...
23 Painter Hill Road
Roxbury, Connecticut 06783
$999,000 | Active
4 Beds | 3 Baths | 1782 Sqft | 3 Acres | 105 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...
21 Hemlock Road
Roxbury, Connecticut 06783
$1,525,000 | Active
4 Beds | 3 Baths | 2200 Sqft | 3.65 Acres | 13 Days on Market
Property Type: Single Family For Sale
This 4 bedroom main house with 2 bedroom guest house provides a peaceful retreat just minutes from town and 1.5 hours from NYC. The cape style main house is privately sited to capture breathtaking western views and sunsets. It features a light-filled open floor plan designed for ...
1030 Washington Woodbury Road
Roxbury, Connecticut 06783
$1,920,000 | Active
4 Beds | 5 Baths | 4874 Sqft | 18.62 Acres | 226 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
$1,795,000 | Active
4 Beds | 4 Baths | 3198 Sqft | 5.42 Acres | 97 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...
85 Good Hill Road
Roxbury, Connecticut 06783
$1,269,000 | Active
3 Beds | 3 Baths | 2440 Sqft | 2 Acres | 32 Days on Market
Property Type: Single Family For Sale
Completely remodeled 3 bedroom, 2.5 bath open concept home, with two fireplaces (one with wood burning insert), kitchen with stainless appliances, granite counters and large island. Property is private - boarders 18 acre land trust and farm land. Gunite pool (propane heater) with...
20 Wellers Bridge Road
Roxbury, Connecticut 06783
$725,000 | Active
3 Beds | 3 Baths | 2059 Sqft | 1.33 Acres | 90 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, ...
18 Tunnel Road
Roxbury, Connecticut 06783
$995,000 | Active
3 Beds | 3 Baths | 2080 Sqft | 3.1 Acres | 141 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...
380 Southbury Road
Roxbury, Connecticut 06783
$1,495,000 | Active
4 Beds | 5 Baths | 4452 Sqft | 6.87 Acres | 146 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...
220 Painter Hill Road
Roxbury, Connecticut 06783
$2,750,000 | Active
4 Beds | 5 Baths | 4570 Sqft | 4.68 Acres | 126 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 ...
22 Woods Road
Roxbury, Connecticut 06783
$1,235,000 | Active
4 Beds | 3 Baths | 3476 Sqft | 6.89 Acres | 21 Days on Market
Property Type: Single Family For Sale
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 e...
20 Wellers Bridge Road
Roxbury, Connecticut 06783
$725,000 | Under Contract - Continue
3 Beds | 3 Baths | 2059 Sqft | 1.33 Acres | 71 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, ...
77 Judds Bridge Road
Roxbury, Connecticut 06783
$1,295,000 | Active
4 Beds | 3 Baths | 2901 Sqft | 3.65 Acres | 27 Days on Market
Property Type: Single Family For Sale
A custom-designed Judds Bridge Colonial in a coveted location, privately set amid mature trees and established plantings. A dramatic double-height marble foyer introduces the homes beautiful architectural millwork and rich cherry floors on the main level. The well-proportioned in...
286 South Street
Roxbury, Connecticut 06783
$995,000 | Under Contract
5 Beds | 5 Baths | 2804 Sqft | 8.4 Acres | 429 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...
94 Judds Bridge Road
Roxbury, Connecticut 06783
$649,719 | Under Contract - Continue
2 Beds | 2 Baths | 1990 Sqft | 8.7 Acres | 69 Days on Market
Property Type: Single Family For Sale
Compelling opportunity nestled in the heart of Roxburys coveted Battleswamp and Mine Hill Preserve area. This remarkable 8.9 acre property features approximately four acres of open meadows, dramatic stone outcroppings, sweeping lawns, woodland privacy and natural beauty. Extensiv...
45 Chalybes Road
Roxbury, Connecticut 06783
$995,000 | Under Contract
3 Beds | 4 Baths | 2725 Sqft | 2.97 Acres | 124 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...
297 Painter Hill Road
Roxbury, Connecticut 06783
$4,495,000 | Active
4 Beds | 7 Baths | 6139 Sqft | 14.81 Acres | 30 Days on Market
Property Type: Single Family For Sale
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 coffere...
137 Davenport Road
Roxbury, Connecticut 06783
$950,000 | Active
3 Beds | 2 Baths | 1614 Sqft | 2.27 Acres | 102 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 | 44 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 | 49 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...
8 Bayberry Hill
Roxbury, Connecticut 06783
$3,650,000 | Under Contract - Continue
5 Beds | 6 Baths | 5940 Sqft | 31.77 Acres | 452 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 | 56 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...
24 Hickory Lane
Roxbury, Connecticut 06783
$1,099,000 | Active
4 Beds | 4 Baths | 3340 Sqft | 3.01 Acres | 140 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 | 140 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...
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 | 65 Days on Market
Property Type: Single Family For Sale
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 s...
50 Southbury Road
Roxbury, Connecticut 06783
$725,000 | Active
5 Beds | 3 Baths | 1365 Sqft | 2 Acres | 85 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 | 88 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 | 97 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...
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 ...
25 Highmeadow Lane
Roxbury, Connecticut 06783
$1,795,000 | Active
4 Beds | 4 Baths | 4310 Sqft | 17.31 Acres | 104 Days on Market
Property Type: Single Family For Sale
Imagine yourself at this private Litchfield County estate where open land, views, and timeless New England charm come together. Set on over 17 acres, this exceptional property offers the rare combination of privacy, recreation, and versatility, featuring a beautifully appointed C...
99 Carriage Lane
Roxbury, Connecticut 06783
$1,495,000 | Active
4 Beds | 3 Baths | 6395 Sqft | 3.79 Acres | 361 Days on Market
Property Type: Single Family For Sale
Welcome to 99 Carriage Lane, a private Roxbury estate offering over 6,000 square feet of refined living space, exceptional privacy on nearly four acres, and the opportunity to create a true resort-style outdoor retreat with approved pool plans. Set at the end of a quiet cul-de-sa...
179 South Street
Roxbury, Connecticut 06783
$985,000 | Active
3 Beds | 2 Baths | 1772 Sqft | 12.74 Acres | 158 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 | 188 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 ...