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Roxbury, CT Homes for Sale with Pool

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  • /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
  • /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
  • /38

    $4,495,000

    • 4 Beds
    • 7 Baths
    • 6,139 Sq Ft

    297 Painter Hill Rd, Roxbury, CT 06783

    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 coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room.

    Peter Klemm Klemm Real Estate Inc

    297 Painter Hill Rd, Roxbury, CT 06783
  • /22

    $1,095,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,031 Sq Ft

    246 North St, Roxbury, CT 06783

    Juniper Hill offers masterfully upgraded one level living in Roxbury, Connecticut. Called 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. Large, level yard and play area that is difficult to find at this price point in the Litchfield

    Fred Bond William Pitt Sotheby's Int'l

    246 North St, 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
  • /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
  • /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
  • /20

    $1,269,000

    $31K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,440 Sq Ft

    85 Good Hill Rd, Roxbury, CT 06783

    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 pavilion and fire pit for entertaining. Hot tub off main bedroom patio. Property features stone walls, steps and

    Jason Saphire www.HomeZu.com

    85 Good Hill Rd, 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

Home Price Trends

Median Sale Price
$1,400,000
Median Single Family Sale Price
$1,400,000
Median Townhouse Sale Price
$1,322,500
Median 2 Bedroom Sale Price
$1,009,000
Median 1 Bedroom Sale Price
$808,000
Average Price Per Sq Ft
$489
Number of Homes for Sale
31
Last 12 months Home Sales
31
Months of Supply
12.00
Median List Price
$1,495,000
Median Change From 1st List Price
12%
Median Home Sale Price YoY Change
13%
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