18

Colonial Homes for Sale in Roxbury, CT

Section Image Section Image
  • /38

    $850,000

    • 3 Beds
    • 2 Baths
    • 2,489 Sq Ft

    47 South St, Roxbury, CT 06783

    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

    Agent Photo

    Michelle Alvord

    Berkshire Hathaway NE Prop.

    47 South St, Roxbury, CT 06783
  • /40

    $1,025,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,556 Sq Ft

    336 South St, Roxbury, CT 06783

    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 an impressive family room highlighted by a floor-to-ceiling fireplace and custom built-ins. The kitchen is

    Karen Gilmore Redfin Corporation

    336 South St, Roxbury, CT 06783
  • /40

    $2,895,000

    • 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
  • /26

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,336 Sq Ft

    38 W Mountain Ln, Roxbury, CT 06783

    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

    Maria Taylor Klemm Real Estate Inc

    38 W Mountain Ln, Roxbury, CT 06783
  • /33

    $950,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,028 Sq Ft

    16 Jonathan Dr, Roxbury, CT 06783

    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

    Joyce Drakeley Drakeley Real Estate, Inc.

    16 Jonathan Dr, Roxbury, CT 06783
  • /40

    $1,995,000

    $480K 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

    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 ideal for hosting gatherings and entertaining with ease. The modern kitchen is a dream for any home chef, complete with

    Debra Tricarico Houlihan Lawrence

    99 Carriage Ln, Roxbury, CT 06783
  • /36

    $995,000

    $200K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 2,804 Sq Ft

    286 South St, Roxbury, CT 06783

    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 residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen.

    Kathryn Clair William Pitt Sotheby's Int'l

    286 South St, Roxbury, CT 06783
  • /40

    $1,550,000

    $50K 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

    $1,049,000

    $50K 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

    $1,595,000

    $54K 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
  • /40

    $1,795,000

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

    25 Highmeadow Ln, Roxbury, CT 06783

    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 has sliders that open to a jumbo 58' deck with awning and open views. Generous main-level spaces include a dramatic

    William Bolls Compass Connecticut, LLC

    25 Highmeadow Ln, Roxbury, CT 06783
  • /34

    $2,000,000

    • 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
  • /34

    $3,395,000

    $1M PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 7,063 Sq Ft

    11 Ravenrock, Roxbury, CT 06783

    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 court, one-bedroom caretaker's apartment over a 3-bay garage, two bedroom guest apartment and greenhouse. This compound

    Maria Taylor Klemm Real Estate Inc

    11 Ravenrock, 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

Home Price Trends

Median Sale Price
$1,400,000
Median Single Family Sale Price
$1,289,000
Median Townhouse Sale Price
$1,360,000
Median 2 Bedroom Sale Price
$796,783
Median 1 Bedroom Sale Price
$808,000
Average Price Per Sq Ft
$490
Number of Homes for Sale
33
Last 12 months Home Sales
30
Months of Supply
13.20
Median List Price
$1,336,500
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
15%
How to Buy a Home How to Finance a Home How to Sell a Home