Roxbury, CT homes for sale & real estate

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ABOUT THIS HOME
Roxbury, CT Homes for Sale
Stunning Post & Beam Home with Extensive Upgrades. This beautifully updated Post & Beam residence offers exceptional craftsmanship and modern amenities throughout. Over the past five years, the home has received numerous enhancements, including a new roof, remodeled kitchen with tile flooring, all-new Pella windows and doors, asphalt driveway, 5-zone LP boiler, central A/C unit, and more. The inviting interior centers around a dramatic two-story stair hall and an expansive Great Room with a cathedral ceiling and wood-burning fireplace-ideal for entertaining or relaxing evenings. Adjacent is a fully renovated eat-in kitchen featuring a large center island with honed granite count

$1,155,000

4 beds2.5 baths3,340 sq ft

24 Hickory Ln, Roxbury, CT 06783

3.01 acre lot • 2 garage spots • Built 1987

ABOUT THIS HOME
Roxbury, CT Homes for Sale
67 Squire Road blends striking modern architecture with timeless New England character on nearly 11 private acres in Roxbury. Thoughtfully designed and beautifully executed, this contemporary retreat offers 4,371 sq ft of light-filled living space with 5 bedrooms and 3 spa-quality baths. Radiant-heated white oak floors and walls of glass frame the surrounding landscape, bringing nature into the heart of the home and creating an effortless sense of openness. The chef's kitchen - crafted in collaboration with iconic designer Paolo Boffi - combines minimalist elegance with exceptional functionality. Sleek lines, high-performance appliances, and effortless flow make it a true centerpiece for bo

$3,975,000

5 beds4 baths4,371 sq ft

67 Squire Rd, Roxbury, CT 06783

Private acres • Finnish sauna • Chef's kitchen

ABOUT THIS HOME
Roxbury, CT Homes for Sale
Tucked away in the picturesque hills of Litchfield County, right on the desirable Woodbury/Roxbury line, this stunning Colonial-Contemporary residence offers an unparalleled blend of privacy, natural beauty, and modern comfort on nearly 10 acres of pristine land. Surrounded by mature trees, vibrant plantings, and lush greenery, the property is enhanced by the gentle sounds of Transylvania Brook flowing just beyond the backyard, creating a truly tranquil and secluded setting. A long, paved, and beautifully lighted driveway welcomes you to this distinctive home, where a grand double-door entry opens to a spacious foyer complete with a unique indoor water feature. Inside, the home features thr

$1,195,000

3 beds2.5 baths4,012 sq ft

24 Roxbury Rd, Woodbury, CT 06798

Indoor water feature • Four-season sunroom • Fenced-in yard

ABOUT THIS HOME
Roxbury, CT Homes for Sale
A distinguished equestrian estate of rare beauty, this property unites timeless New England architecture with the serenity of country living. Approached by a gated, tree-lined drive, the residence evokes an air of grace and permanence, set amidst sweeping pastures and centuries-old trees. The main residence exudes historic character and refinement, where wide-plank floors, hand-hewn beams, and wood-burning hearths harmonize with modern appointments. The vaulted primary suite, crowned with exposed beams and a private fireplace, offers a sanctuary of repose, while the luminous screened veranda invites alfresco dining and quiet contemplation. Beyond the main home, the grounds unfold into an id

$1,399,000

4 beds3.5 baths3,077 sq ft

96 Squire Rd, Roxbury, CT 06783

Gated drive • Wood burning hearths • Equestrian estate

ABOUT THIS HOME
Roxbury, CT Homes for Sale
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 beautiful wood floors throughout. The open floor plan creates a sense of airiness and flow, while large windows bring the surrounding nature indoors. Whether you're relaxing in the peaceful primary bedroom or gathering in the inviting living area, every space feels serene and connected to the outdoors. The

$795,000

3 beds2.5 baths2,336 sq ft

38 W Mountain Ln, Roxbury, CT 06783

Private road • Open floor plan • Wood floors

Property at 31 Hickory Ln, Roxbury, CT 06783, 4 beds, 4 baths

$1,795,000

4 beds4 baths6,169 sq ft

31 Hickory Ln, Roxbury, CT 06783

Property at 47 South St, Roxbury, CT 06783, 3 beds, 2 baths

$875,000

3 beds2 baths2,489 sq ft

47 South St, Roxbury, CT 06783

Property at 336 South St, Roxbury, CT 06783, 3 beds, 2.5 baths

$995,000

3 beds2.5 baths2,556 sq ft

336 South St, Roxbury, CT 06783

Property at 55 Mallory Rd, Roxbury, CT 06783, 4 beds, 3 baths

$739,000

4 beds3 baths2,682 sq ft

55 Mallory Rd, Roxbury, CT 06783

Property at 50 Southbury Rd, Roxbury, CT 06783, 5 beds, 3 baths

$950,000

5 beds3 baths2,000 sq ft

50 Southbury Rd, Roxbury, CT 06783

Property at 35 Schoolhouse Rd, Roxbury, CT 06783, 4 beds, 4.5 baths

$3,650,000

4 beds4.5 baths5,072 sq ft

35 Schoolhouse Rd, Roxbury, CT 06783

Property at 242 Tophet Rd, Roxbury, CT 06783, 3 beds, 2 baths

$849,000

3 beds2 baths1,862 sq ft

242 Tophet Rd, Roxbury, CT 06783

Property at 67 Transylvania Rd, Roxbury, CT 06783, 4 beds, 3 baths

$919,000

4 beds3 baths3,624 sq ft

67 Transylvania Rd, Roxbury, CT 06783

Property at 4 Judge Rd, Roxbury, CT 06783, 3 beds, 2 baths

$3,200,000

3 beds2 baths1,974 sq ft

4 Judge Rd, Roxbury, CT 06783

Property at 22 E Woods Rd, Roxbury, CT 06783, 4 beds, 2.5 baths

$735,000

4 beds2.5 baths3,476 sq ft

22 E Woods Rd, Roxbury, CT 06783

Property at 23 Painter Hill Rd, Roxbury, CT 06783, 4 beds, 3 baths

$999,000

4 beds3 baths1,782 sq ft

23 Painter Hill Rd, Roxbury, CT 06783

Property at 286 South St, Roxbury, CT 06783, 5 beds, 4 baths

$1,195,000

5 beds4 baths2,804 sq ft

286 South St, Roxbury, CT 06783

Property at 179 South St, Roxbury, CT 06783, 3 beds, 2 baths

$1,275,000

3 beds2 baths1,772 sq ft

179 South St, Roxbury, CT 06783

Property at 18 Tunnel Rd, Roxbury, CT 06783, 3 beds, 2.5 baths

$1,025,000

3 beds2.5 baths2,080 sq ft

18 Tunnel Rd, Roxbury, CT 06783

Property at 85 Good Hill Rd, Roxbury, CT 06783, 3 beds, 2.5 baths

$1,630,000

3 beds2.5 baths2,440 sq ft

85 Good Hill Rd, Roxbury, CT 06783

Property at 8 Bayberry Hl, Roxbury, CT 06783, 5 beds, 5 baths

$3,995,000

5 beds5 baths5,940 sq ft

8 Bayberry Hl, Roxbury, CT 06783

Property at 143 Tophet Rd, Roxbury, CT 06783, 4 beds, 5.5 baths

$2,295,000

4 beds5.5 baths5,848 sq ft

143 Tophet Rd, Roxbury, CT 06783

Property at 11 Ravenrock Rd, Roxbury, CT 06783, 4 beds, 5.5 baths

$3,998,000

4 beds5.5 baths7,063 sq ft

11 Ravenrock Rd, Roxbury, CT 06783

Property at 88 Rucum Rd, Roxbury, CT 06783, 5 beds, 5 baths

$2,195,000

5 beds5 baths5,113 sq ft

88 Rucum Rd, Roxbury, CT 06783

Property at 81 Chalybes Rd W, Roxbury, CT 06783, 4 beds, 4.5 baths

$2,200,000

4 beds4.5 baths3,677 sq ft

81 Chalybes Rd W, Roxbury, CT 06783

Property at 103B Chalybes Rd W, Roxbury, CT 06783, 4 beds, 2.5 baths

$3,050,000

4 beds2.5 baths4,071 sq ft

103B Chalybes Rd W, Roxbury, CT 06783

Property at L7&L8 Willow Brook Dr, Roxbury, CT 06783, 5 beds, 3.5 baths

$5,499,000

5 beds3.5 baths6,729 sq ft

L7&L8 Willow Brook Dr, Roxbury, CT 06783

Property at 247 Painter Hill Rd, Roxbury, CT 06783, 3 beds, 4 baths

$1,595,000

3 beds4 baths2,396 sq ft

247 Painter Hill Rd, Roxbury, CT 06783

Property at 99 Carriage Ln, Roxbury, CT 06783, 4 beds, 2.5 baths

$1,675,000

4 beds2.5 baths6,395 sq ft

99 Carriage Ln, Roxbury, CT 06783

Property at 239 Good Hill Rd, Roxbury, CT 06783, 5 beds, 4.5 baths

$2,150,000

5 beds4.5 baths4,000 sq ft

239 Good Hill Rd, Roxbury, CT 06783

Property at 32 Grassy Hill Rd, Roxbury, CT 06783, 4 beds, 4 baths

$2,150,000

4 beds4 baths4,728 sq ft

32 Grassy Hill Rd, Roxbury, CT 06783

Property at 33 Sentry Hill Rd, Roxbury, CT 06783, 4 beds, 3.5 baths

$1,495,000

4 beds3.5 baths2,716 sq ft

33 Sentry Hill Rd, Roxbury, CT 06783

Property at 2 Pickett Rd, Roxbury, CT 06783, 5 beds, 3.5 baths

$1,784,000

5 beds3.5 baths3,096 sq ft

2 Pickett Rd, Roxbury, CT 06783

Property at 97 Chalybes Rd W, Roxbury, CT 06783, 4 beds, 4 baths

$2,480,000

4 beds4 baths4,266 sq ft

97 Chalybes Rd W, Roxbury, CT 06783

Property at 45 Moosehorn Rd, Roxbury, CT 06783, 4 beds, 3.5 baths

$1,949,000

4 beds3.5 baths4,517 sq ft

45 Moosehorn Rd, Roxbury, CT 06783

Property at 69 Moosehorn Rd, Roxbury, CT 06783

$549,000

— beds— baths— sq ft

69 Moosehorn Rd, Roxbury, CT 06783

Property at Lot 1 Chalybes Rd W, Roxbury, CT 06783

$399,000

— beds— baths— sq ft

Lot 1 Chalybes Rd W, Roxbury, CT 06783

Property at 31 Holmes Rd, Roxbury, CT 06783

$450,000

— beds— baths— sq ft

31 Holmes Rd, Roxbury, CT 06783

Property at 200 North St, Roxbury, CT 06783

$479,000

— beds— baths— sq ft

200 North St, Roxbury, CT 06783

$275,000

— beds— baths— sq ft

Booth Rd, Roxbury, CT 06783

Property at 307 North St, Roxbury, CT 06783

$234,900

— beds— baths— sq ft

307 North St, Roxbury, CT 06783

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Average home prices near Roxbury, CT

Cities

Zip Codes
Minor Civil Divisions

Roxbury, CT real estate trends

$1.2M

Sale price

-2.0%
since last year

$499

Sale $/sq ft

-5.0%
since last year

Under list price

5.8%

Days on market

120

Down payment

—

Total homes sold

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