Roxbury, CT homes for sale & real estate

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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

$1,275,000

3 beds2.5 baths4,012 sq ft

24 Roxbury Rd, Woodbury, CT 06793

9.97 acre lot • 2 garage spots • Pool

ABOUT THIS HOME
Roxbury, CT Homes for Sale
Welcome to your quintessential Roxbury retreat, a classic 3-bedroom Colonial nestled on over 4.5 picturesque park-like acres. This property offers the perfect blend of tranquil country living with the convenience of a great commuting location, just 90 minutes to NYC. Step inside to discover a home that has been freshly painted both inside and out, exuding a crisp, clean feel. The heart of the home, the kitchen, has been thoughtfully updated with new cabinetry and modern appliances, making it a chef's delight. Just off the kitchen and great room, you'll find a dedicated kitchen garden area, perfect for cultivating your own fresh herbs and vegetables. Outside, the expansive, level grounds pro

$995,000

3 beds2.5 baths2,556 sq ft

336 South St, Roxbury, CT 06783

Generac generator • Storage shed • Inground pool

ABOUT THIS HOME
Roxbury, CT Homes for Sale
If privacy in the Litchfield Hills is your aspiration, this is the house for you. Country Cape with covered front porch set back off the road. Custom built home that is being offered for the first time on the market. SOLID QUALTIY CONSTRUCTION. New owner needs to do cosmetic updates and flooring to make it their own. Expansive kitchen with angled island leads to the open 2 story great room with floor to ceiling fieldstone fireplace. Detached garage with upper level workshop that has electricity & can accommodate a coal/wood stove. Come explore all the possibilities this property has to offer. Roxbury is a blend of historic charm, environmental stewardship, & community warmth that

$779,000

4 beds3 baths2,682 sq ft

55 Mallory Rd, Roxbury, CT 06783

Covered front porch • Expansive kitchen • Open great room

ABOUT THIS HOME
Roxbury, CT Homes for Sale
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 to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as histori

$1,275,000

3 beds2 baths1,772 sq ft

179 South St, Roxbury, CT 06783

Renovated barn • Antique home • Historic landmark

OPEN SEP 28, 12PM TO 2PM

ABOUT THIS HOME
Roxbury, CT Homes for Sale
Welcome to 2 Old Turnpike Road, a classic 3-bedroom, 2-bath ranch nestled on 2.52 acres in the picturesque town of Roxbury, CT. Offering 1,372 sq. ft. of comfortable living space plus a full unfinished basement with garage access, this home provides both charm and potential. Step inside to find a bright and inviting layout with spacious living areas, ideal for both everyday living and entertaining. The ranch-style floor plan makes for easy one-level living, while the basement offers abundant storage. Enjoy your morning coffee on the 4-season sun porch. It also features new castle windows with a transferrable lifetime warranty, a new water softener, a newer stone lined indirect hot water hea

$599,900

3 beds2 baths1,372 sq ft

2 Old Turnpike Rd, Roxbury, CT 06783

4 season sun porch • New water softener • New castle windows

Property at 30 Hickory Ln, Roxbury, CT 06783, 4 beds, 5.5 baths

$1,495,000

4 beds5.5 baths4,721 sq ft

30 Hickory Ln, 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 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 67 Transylvania Rd, Roxbury, CT 06783, 4 beds, 3 baths

$959,000

4 beds3 baths3,624 sq ft

67 Transylvania 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 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 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 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 242 Tophet Rd, Roxbury, CT 06783, 3 beds, 2 baths

$895,000

3 beds2 baths1,862 sq ft

242 Tophet Rd, Roxbury, CT 06783

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

$1,625,000

3 beds4 baths2,396 sq ft

247 Painter Hill Rd, 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 33 Sentry Hill Rd, Roxbury, CT 06783, 4 beds, 3.5 baths

$1,525,000

4 beds3.5 baths2,716 sq ft

33 Sentry 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 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 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 23 Painter Hill Rd, Roxbury, CT 06783, 4 beds, 3 baths

$1,049,000

4 beds3 baths1,782 sq ft

23 Painter Hill Rd, Roxbury, CT 06783

Property at 253 Tophet Rd, Roxbury, CT 06783, 4 beds, 3.5 baths

$1,575,000

4 beds3.5 baths2,437 sq ft

253 Tophet Rd, Roxbury, CT 06783

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

$1,975,000

4 beds3.5 baths4,517 sq ft

45 Moosehorn 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 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 18 Tunnel Rd, Roxbury, CT 06783, 3 beds, 2.5 baths

$1,075,000

3 beds2.5 baths2,080 sq ft

18 Tunnel Rd, 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 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 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 11 Ravenrock Rd, Roxbury, CT 06783, 4 beds, 5.5 baths

$4,450,000

4 beds5.5 baths7,063 sq ft

11 Ravenrock Rd, 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 Lot 1 Chalybes Rd W, Roxbury, CT 06783

$399,000

— beds— baths— sq ft

Lot 1 Chalybes Rd W, Roxbury, CT 06783

$275,000

— beds— baths— sq ft

Booth Rd, Roxbury, CT 06783

Property at 200 North St, Roxbury, CT 06783

$479,000

— beds— baths— sq ft

200 North St, Roxbury, CT 06783

Property at 307 North St, Roxbury, CT 06783

$234,900

— beds— baths— sq ft

307 North St, Roxbury, CT 06783

Property at 238 North St, Roxbury, CT 06783

$449,000

— beds— baths— sq ft

238 North St, Roxbury, CT 06783

Property at Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783

$999,000

— beds— baths— sq ft

Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783

Property at Lot 00 Chalybes Rd W, Roxbury, CT 06783

$1,895,000

— beds— baths— sq ft

Lot 00 Chalybes Rd W, Roxbury, CT 06783

Property at 0 Wellers Bridge Rd, Roxbury, CT 06783

$429,000

— beds— baths— sq ft

0 Wellers Bridge Rd, Roxbury, CT 06783

Property at Lot 4 Chalybes Rd W, Roxbury, CT 06783

$599,000

— beds— baths— sq ft

Lot 4 Chalybes Rd W, Roxbury, CT 06783

Property at Lot 3 Chalybes Rd, Roxbury, CT 06783

$499,000

— beds— baths— sq ft

Lot 3 Chalybes Rd, Roxbury, CT 06783

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Average home prices near Roxbury, CT

Cities

Zip Codes
Minor Civil Divisions

Roxbury, CT real estate trends

$1.47M

Sale price

+211.7%
since last year

$484

Sale $/sq ft

+89.1%
since last year

Under list price

5.3%

Days on market

108

Down payment

—

Total homes sold

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