14

Roxbury, CT Homes for Sale with Pool

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  • /40

    $1,075,000

    • 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
  • /24

    $1,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,566 Sq Ft

    176 Apple Ln, Roxbury, CT 06783

    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 property feels like a private club: stone walls, curated landscaping, quiet woods, and outdoor spaces designed for long

    Kathryn Bassett William Pitt Sotheby's Int'l

    176 Apple Ln, 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
  • /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
  • /35

    $2,045,000

    $150K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 5,113 Sq Ft

    88 Rucum Rd, Roxbury, CT 06783

    Located in picturesque Roxbury, CT-nestled in southern Litchfield County and under two hours from New York City-this exquisite barn-style residence offers the perfect blend of rustic charm and modern luxury. Set on 8 sprawling acres, the property features an expansive lawn, beautifully curated specimen plantings, and a sparkling pool with integrated spa-ideal for both relaxation and entertaining.

    Pels Matthews W. Raveis Lifestyles Realty

    88 Rucum Rd, Roxbury, CT 06783
  • /40

    $1,795,000

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

    25 Highmeadow Ln, Roxbury, CT 06783

    Stunning 4-bedroom colonial estate on 17+ private acres in desirable Roxbury, CT. Set on open rolling lawns with sweeping sunrise/sunset views, this property offers country living with exceptional versatility. The sun-filled eat-in kitchen features high-end appliances and sliders to a large 58' deck with open views and a retractable awning. Generous main-level spaces include a dramatic vaulted

    William Bolls Compass Connecticut, LLC

    25 Highmeadow Ln, Roxbury, CT 06783
  • /33

    $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
  • /22

    $1,195,000

    • 3 Beds
    • 2 Baths
    • 2,031 Sq Ft

    246 North St, Roxbury, CT 06783

    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 compelling terrain. Kelly + Co Design awarded Best Interior Designer Small Home/Cottage, 2020, CT Cottage and Gardens

    Fred Bond William Pitt Sotheby's Int'l

    246 North St, Roxbury, CT 06783
  • /27

    $3,995,000

    • 5 Beds
    • 5.5 Baths
    • 7,121 Sq Ft

    47 Squire Rd, Roxbury, CT 06783

    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 Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms

    Maria Taylor Klemm Real Estate Inc

    47 Squire Rd, 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
  • /33

    $1,630,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,440 Sq Ft

    85 Good Hill Rd, Roxbury, CT 06783

    At the end of a long, winding private driveway, this exceptional Roxbury estate offers total seclusion & tranquility-surrounded entirely by protected land trust. Just 2 miles from Roxbury Center and a scenic 2-hr drive from NYC, this rare property is the perfect country escape or full-time residence. The main home is in impeccable, move-in condition, featuring dramatic vaulted ceilings in both

    Pat Lahoud Lahoud William Pitt Sotheby's Int'l

    85 Good Hill Rd, Roxbury, CT 06783
  • /27

    $1,649,000

    • 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
  • /35

    $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

Home Trends in Roxbury, CT

Housing Trends

Median Sale Price
$1,400,000
Median Single Family Sale Price
$1,378,000
Median Townhouse Sale Price
$1,472,500
Average Price Per Sq Ft
$475
Number of Homes for Sale
30
Last 12 months Home Sales
31
Months of Supply
11.60
Median List Price
$1,499,000
Median Change From 1st List Price
11%
Median Home Sale Price YoY Change
33%
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