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Connecticut · Real Estate

Homes for Sale in
Roxbury, CT

There are currently 31 homes for sale in Roxbury, Connecticut with an average list price of $1,419,806.

Roxbury is a small, affluent Litchfield County town of about 2,300 with a remarkable literary and artistic pedigree — Arthur Miller lived here for decades, and the town has long attracted painters, writers, and intellectuals from New York. The landscape is rolling hills, stone walls, and carefully preserved farmland. Minimal development, exceptional privacy, and a community that prizes its character above all else. Among the most exclusive rural addresses in Connecticut.

For Sale

31

active listings

Avg. Sale Price

$1.4M

$320K–$2.9M

Avg. Size Sold

3,135 sf

last 12 mo

vs. Ask Price

-4.1%

avg. paid vs. ask

Stats based on 46 closings in the last 12 months

Showing 12 of 31 listings in Roxbury

Lot 7 & Lot 8 Willow Brook Drive, Roxbury, CT
Active
$949,000
Residential Land
Lot 7 & Lot 8 Willow Brook Drive
Roxbury, CT 06783
William Pitt Sotheby's Int'l SmartMLS
220 Painter Hill Road, Roxbury, CT
Active
$2,895,000
4 bd · 5.00 ba · 4,570 sqft
220 Painter Hill Road
Roxbury, CT 06783
W. Raveis Lifestyles Realty SmartMLS
77 Tophet Road, Roxbury, CT
Active
$2,395,000
4 bd · 5.00 ba · 6,670 sqft
77 Tophet Road
Roxbury, CT 06783
Compass Connecticut, LLC SmartMLS
24 Hickory Lane, Roxbury, CT
Active
$1,155,000
4 bd · 3.00 ba · 3,340 sqft
24 Hickory Lane
Roxbury, CT 06783
William Pitt Sotheby's Int'l SmartMLS
216 Baker Road, Roxbury, CT
Active
$689,000
4 bd · 2.00 ba · 2,008 sqft
216 Baker Road
Roxbury, CT 06783
RE/MAX Right Choice SmartMLS
33 Sentry Hill Road, Roxbury, CT
Active
$1,649,000
4 bd · 4.00 ba · 2,716 sqft
33 Sentry Hill Road
Roxbury, CT 06783
Klemm Real Estate Inc SmartMLS
18 Tunnel Road, Roxbury, CT
Active
$1,099,000
3 bd · 3.00 ba · 2,080 sqft
18 Tunnel Road
Roxbury, CT 06783
Klemm Real Estate Inc SmartMLS
380 Southbury Road, Roxbury, CT
Active
$1,600,000
4 bd · 5.00 ba · 4,452 sqft
380 Southbury Road
Roxbury, CT 06783
Berkshire Hathaway NE Prop. SmartMLS
179 South Street, Roxbury, CT
Active
$985,000
Residential Land
179 South Street
Roxbury, CT 06783
William Pitt Sotheby's Int'l SmartMLS
179 South Street, Roxbury, CT
Active
$985,000
3 bd · 2.00 ba · 1,772 sqft
179 South Street
Roxbury, CT 06783
William Pitt Sotheby's Int'l SmartMLS
45 Chalybes Road, Roxbury, CT
Active
$995,000
3 bd · 4.00 ba · 2,725 sqft
45 Chalybes Road
Roxbury, CT 06783
William Pitt Sotheby's Int'l SmartMLS
11 Evergreen Drive, Roxbury, CT
Active
$1,200,000
4 bd · 4.00 ba · 3,800 sqft
11 Evergreen Drive
Roxbury, CT 06783
William Pitt Sotheby's Int'l SmartMLS
See All 31 Homes in Roxbury

Buying a Home in Roxbury, CT

Current Market Snapshot

Entry Price
$275K
lowest listed
Avg. Price
$1.4M
list price
Top of Market
$4M
highest listed
Listings by Bedroom Count
3 beds
7
4 beds
12
5 beds
5
Property Types Available
Single Family · 24 Land · 7

The Roxbury real estate market currently has 31 active listings with an average list price of $1,419,806 and a price range from $275,000 to $3,995,000. Single Family homes make up the largest share of available inventory. Most listings are 4-bedroom homes. The average home size is 2,973 sq ft. All listings are sourced directly from SmartMLS and updated every 15 minutes.

Frequently Asked Questions

How many homes are for sale in Roxbury, CT right now?
As of April 2026, there are 31 active listings in Roxbury, CT. All listings are updated every 15 minutes directly from SmartMLS.
What is the average home price in Roxbury, CT?
The average list price in Roxbury is $1,419,806. Homes currently range from $275,000 to $3,995,000.
What size homes are most common in Roxbury, CT?
The most common listing in Roxbury is a 4-bedroom home (12 listings). Other common sizes include 3-bedroom (7) and 5-bedroom (5). The average home size is 2,973 sq ft.
What types of homes are available in Roxbury, CT?
Current listings in Roxbury include: Single Family (24), Land (7).
Is Roxbury, CT a good place to buy a home?
Roxbury is a small, affluent Litchfield County town of about 2,300 with a remarkable literary and artistic pedigree — Arthur Miller lived here for decades, and the town has long attracted painters, writers, and intellectuals from New York. The landscape is rolling hills, stone walls, and carefully preserved farmland. Minimal development, exceptional privacy, and a community that prizes its character above all else. Among the most exclusive rural addresses in Connecticut.
Does RYZE Realty Group serve Roxbury, CT?
Yes — RYZE Realty Group is a Connecticut real estate team serving buyers and sellers across Litchfield County and the greater Connecticut market, including Roxbury. Contact us for a free consultation.

Nearby Towns

Torrington, CT 99 listings
Woodbury, CT 30 listings
Watertown, CT 29 listings
Washington, CT 29 listings
Salisbury, CT 24 listings
Plymouth, CT 23 listings

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