16

Colonial Homes for Sale in Roxbury, CT

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  • /38

    $850,000

    Open Sun 12:30PM - 2:30PM
    • 3 Beds
    • 2 Baths
    • 2,489 Sq Ft

    47 South St, Roxbury, CT 06783

    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 property and make it your

    Agent Photo

    Michelle Alvord

    Berkshire Hathaway NE Prop.

    47 South St, Roxbury, CT 06783
  • /40

    $2,750,000

    $145K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,570 Sq Ft

    220 Painter Hill Rd, Roxbury, CT 06783

    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,

    Stacey Matthews W. Raveis Lifestyles Realty

    220 Painter Hill Rd, Roxbury, CT 06783
  • /38

    $1,099,000

    $56K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,340 Sq Ft

    24 Hickory Ln, Roxbury, CT 06783

    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

    Pat Lahoud Lahoud William Pitt Sotheby's Int'l

    24 Hickory Ln, Roxbury, CT 06783
  • /39

    $3,600,000

    • 5 Beds
    • 4.5 Baths
    • 6,190 Sq Ft

    268 South St, Roxbury, CT 06783

    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

    Peter Klemm Klemm Real Estate Inc

    268 South St, Roxbury, CT 06783
  • /39

    $1,295,000

    • 4 Beds
    • 2.5 Baths
    • 2,901 Sq Ft

    77 Judds Bridge Rd, Roxbury, CT 06783

    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 home's beautiful architectural millwork and rich cherry floors on the main level. The well-proportioned interiors include formal living and dining rooms, office or bonus room, an open and eat-in kitchen with solid cherry

    Joseph Lorino Klemm Real Estate Inc

    77 Judds Bridge Rd, Roxbury, CT 06783
  • /40

    $1,235,000

    • 4 Beds
    • 2.5 Baths
    • 3,476 Sq Ft

    22 E Woods Rd, Roxbury, CT 06783

    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

    Andy Sachs Compass Connecticut, LLC

    22 E Woods Rd, Roxbury, CT 06783
  • /40

    $1,920,000

    $555K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,874 Sq Ft

    1030 Washington Woodbury Rd, Roxbury, CT 06783

    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 pool, and a setting defined by natural beauty and understated presence. With generously proportioned rooms and a strong

    Judith Auchincloss Klemm Real Estate Inc

    1030 Washington Woodbury Rd, Roxbury, CT 06783
  • /38

    $1,495,000

    $240K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 6,395 Sq Ft

    99 Carriage Ln, Roxbury, CT 06783

    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-sac, this beautifully renovated residence blends timeless architectural details with modern amenities and sophisticated

    Debra Tricarico Houlihan Lawrence

    99 Carriage Ln, Roxbury, CT 06783
  • /40

    $1,495,000

    $105K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,452 Sq Ft

    380 Southbury Rd, Roxbury, CT 06783

    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 dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray

    ROSEANN BLANTON Berkshire Hathaway NE Prop.

    380 Southbury Rd, Roxbury, CT 06783
  • /13

    $985,000

    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft

    179 South St, Roxbury, CT 06783

    Own a Piece of Roxbury History! One of Roxbury's 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 tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity

    Kathryn Clair William Pitt Sotheby's Int'l

    179 South St, Roxbury, CT 06783
  • /29

    $995,000

    $104K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    18 Tunnel Rd, Roxbury, CT 06783

    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 minutes to The Mayflower. Pristine renovated private country home with 3 bedrooms/2.5 baths and an ample home office. Open

    Peter Klemm Klemm Real Estate Inc

    18 Tunnel Rd, Roxbury, CT 06783
  • /27

    $1,499,000

    $150K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,716 Sq Ft

    33 Sentry Hill Rd, Roxbury, CT 06783

    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 Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room,

    Peter Klemm Klemm Real Estate Inc

    33 Sentry Hill Rd, Roxbury, CT 06783
  • /38

    $1,795,000

    • 4 Beds
    • 4 Baths
    • 4,310 Sq Ft

    25 Highmeadow Ln, Roxbury, CT 06783

    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 Colonial, classic barn with apartment, heated gunite saltwater pool, and expansive grounds just 90 minutes from

    William Bolls Compass Connecticut, LLC

    25 Highmeadow Ln, Roxbury, CT 06783
  • /35

    $1,795,000

    $205K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,198 Sq Ft

    18 Ranney Hill Rd, Roxbury, CT 06783

    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 planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble

    Sharon McGuire William Pitt Sotheby's Int'l

    18 Ranney Hill Rd, Roxbury, CT 06783
  • /20

    $725,000

    • 3 Beds
    • 2.5 Baths
    • 2,059 Sq Ft

    20 Wellers Bridge Rd, Roxbury, CT 06783

    This handsome 1820's 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, Rebuilt Porch and more. New Well installed dedicated to this property replaced shared source. Interior makeover

    WAYNE PISKURA Klemm Real Estate Inc

    20 Wellers Bridge Rd, Roxbury, CT 06783
  • /33

    $679,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,008 Sq Ft

    216 Baker Rd, Roxbury, CT 06783

    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 room currently used as an office. The main level with a den, living room with fireplace, dining room, and a

    David Landau RE/MAX Right Choice

    216 Baker Rd, Roxbury, CT 06783
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