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Roxbury, CT
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1 - 57 of 57 listings (57 total matches)
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8 Bayberry Hill Roxbury CT 06783
1 / 35
$3,995,000
Single Family Residence For Sale
Active
5
BEDS
6
TOTAL BATHS
5,940
SQFT
8 Bayberry Hill
Roxbury, CT 06783
 
Listing courtesy of Graham Klemm of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (860) 488-6635
11 Ravenrock Road Roxbury CT 06783
1 / 35
$3,595,000
Single Family Residence For Sale
Active
4
BEDS
6
TOTAL BATHS
7,063
SQFT
11 Ravenrock Road
Roxbury, CT 06783
 
Listing courtesy of Maria Taylor of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (203) 578-0397
220 Painter Hill Road Roxbury CT 06783
New Listing - 4 weeks on site
1 / 40
$2,895,000
Single Family Residence For Sale
Active
4
BEDS
5
TOTAL BATHS
3,870
SQFT
220 Painter Hill Road
Roxbury, CT 06783
 
Listing courtesy of Stacey Matthews of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (203) 671-9067
77 Tophet Road Roxbury CT 06783
New Listing - 4 weeks on site
1 / 37
$2,395,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
5
TOTAL BATHS
6,670
SQFT
77 Tophet Road
Roxbury, CT 06783
 
Listing courtesy of Rick Distel of Compass Connecticut, LLC Office Phone: (203) 293-9715 Broker Contact: (646) 417-2720
88 Rucum Road Roxbury CT 06783
1 / 35
$2,045,000
Single Family Residence For Sale
Active
5
BEDS
6
TOTAL BATHS
5,113
SQFT
88 Rucum Road
Roxbury, CT 06783
 
Listing courtesy of Pels Matthews of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (203) 671-5432
18 Ranney Hill Road Roxbury CT 06783
1 / 4
$2,000,000
Single Family Residence For Sale
Coming Soon
4
BEDS
4
TOTAL BATHS
3,198
SQFT
18 Ranney Hill Road
Roxbury, CT 06783
 
Listing courtesy of Sharon Wyant McGuire of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 417-2925
55 Ranney Hill Road Roxbury CT 06783
New Listing - 2 weeks on site
1 / 12
$2,000,000
Land For Sale
Active
26.48
ACRES
LITCHFIELD
COUNTY
55 Ranney Hill Road
Roxbury, CT 06783
 
Listing courtesy of Sharon Wyant McGuire of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 417-2925
1030 Washington Woodbury Road Roxbury CT 06783
Price Change - 3 days ago
1 / 40
$1,995,000
Single Family Residence For Sale
Active
4
BEDS
5
TOTAL BATHS
4,874
SQFT
1030 Washington Woodbury Road
Roxbury, CT 06783
 
Listing courtesy of Judith Auchincloss of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (203) 770-3300
176 Apple Lane Roxbury CT 06783
1 / 31
$1,995,000
Single Family Residence For Sale
Active
4
BEDS
5
TOTAL BATHS
3,566
SQFT
176 Apple Lane
Roxbury, CT 06783
 
Listing courtesy of Kathryn Bassett of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 841-8161
25 Highmeadow Lane Roxbury CT 06783
New Listing - a week on site
1 / 40
$1,795,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
4,310
SQFT
25 Highmeadow Lane
Roxbury, CT 06783
 
Listing courtesy of William Bolls of Compass Connecticut, LLC Office Phone: (203) 293-9715 Broker Contact: (646) 285-8197
233 Southbury Road Roxbury CT 06783
Open House Sun, May 17, 12 PM
Please verify times due to COVID-19
1 / 38
$1,795,000
Single Family Residence For Sale
Active
5
BEDS
6
TOTAL BATHS
5,447
SQFT
233 Southbury Road
Roxbury, CT 06783
 
Listing courtesy of Kathryn Clair of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 948-5255
31 Hickory Lane Roxbury CT 06783
Price Change - 2 weeks ago
1 / 37
$1,685,000
Single Family Residence For Sale
Active
4
BEDS
5
TOTAL BATHS
4,169
SQFT
31 Hickory Lane
Roxbury, CT 06783
 
Listing courtesy of Philippa Malkin of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (203) 671-5432
33 Sentry Hill Road Roxbury CT 06783
1 / 27
$1,649,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
2,716
SQFT
33 Sentry Hill Road
Roxbury, CT 06783
 
Listing courtesy of Peter Klemm of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 864-4940
85 Good Hill Road Roxbury CT 06783
1 / 33
$1,630,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,440
SQFT
85 Good Hill Road
Roxbury, CT 06783
 
Listing courtesy of Pat Lahoud Lahoud of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (860) 868-6925
380 Southbury Road Roxbury CT 06783
Price Change - a week ago
1 / 40
$1,550,000
Single Family Residence For Sale
Active
4
BEDS
5
TOTAL BATHS
4,452
SQFT
380 Southbury Road
Roxbury, CT 06783
 
Listing courtesy of Beatrice Dorlean-Cornet of Berkshire Hathaway NE Prop. Office Phone: (845) 855-8500 Broker Contact: (845) 206-8006
99 Carriage Lane Roxbury CT 06783
Price Change - 4 weeks ago
1 / 38
$1,495,000
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
6,395
SQFT
99 Carriage Lane
Roxbury, CT 06783
 
Listing courtesy of Debra Tricarico of Houlihan Lawrence Office Phone: (203) 746-6565 Broker Contact: (914) 592-3444
56 Goldmine Road Roxbury CT 06783
New Listing - 2 weeks on site
1 / 40
$1,375,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,620
SQFT
56 Goldmine Road
Roxbury, CT 06783
 
Listing courtesy of Fred Bond of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (917) 209-2253
315 North Street Roxbury CT 06783
New Listing - 2 weeks on site
1 / 40
$1,295,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
2,420
SQFT
315 North Street
Roxbury, CT 06783
 
Listing courtesy of Kathryn Clair of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 948-5255
11 Evergreen Drive Roxbury CT 06783
1 / 3
$1,200,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
3,800
SQFT
11 Evergreen Drive
Roxbury, CT 06783
 
Listing courtesy of Sharon Wyant McGuire of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 417-2925
246 North Street Roxbury CT 06783
New Listing - 6 days on site
1 / 22
$1,195,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,031
SQFT
246 North Street
Roxbury, CT 06783
 
Listing courtesy of Fred Bond of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (917) 209-2253
24 Hickory Lane Roxbury CT 06783
1 / 38
$1,155,000
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
3,340
SQFT
24 Hickory Lane
Roxbury, CT 06783
 
Listing courtesy of Pat Lahoud Lahoud of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (860) 866-7756
18 Tunnel Road Roxbury CT 06783
1 / 29
$1,099,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,080
SQFT
18 Tunnel Road
Roxbury, CT 06783
 
Listing courtesy of Peter Klemm of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 864-4940
23 Painter Hill Road Roxbury CT 06783
New Listing - 5 days on site
1 / 25
$1,095,000
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
1,782
SQFT
23 Painter Hill Road
Roxbury, CT 06783
 
Listing courtesy of Peter Klemm of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 864-4940
336 South Street Roxbury CT 06783
New Listing - 2 weeks on site
1 / 40
$1,075,000
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,556
SQFT
336 South Street
Roxbury, CT 06783
 
Listing courtesy of Karen Gilmore of Redfin Corporation Office Phone: (203) 349-8711 Broker Contact: (203) 482-9144
28 Garnet Road Roxbury CT 06783
New Listing - a week on site
1 / 35
$1,050,000
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
2,301
SQFT
28 Garnet Road
Roxbury, CT 06783
 
Listing courtesy of Lisa Rollins of Compass Connecticut, LLC Office Phone: (203) 245-1593 Broker Contact: (203) 671-0295
286 South Street Roxbury CT 06783
Price Change - 2 weeks ago
1 / 36
$1,049,000
Single Family Residence For Sale
Active
5
BEDS
5
TOTAL BATHS
2,804
SQFT
286 South Street
Roxbury, CT 06783
 
Listing courtesy of Kathryn Clair of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 948-5255
45 Chalybes Road Roxbury CT 06783
1 / 32
$995,000
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
1,545
SQFT
45 Chalybes Road
Roxbury, CT 06783
 
Listing courtesy of Kathryn Bassett of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 841-8161
179 South Street Roxbury CT 06783
1 / 13
$985,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,772
SQFT
179 South Street
Roxbury, CT 06783
 
Listing courtesy of Kathryn Clair of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 948-5255
179 South Street Roxbury CT 06783
1 / 14
$985,000
Land For Sale
Active
12.74
ACRES
LITCHFIELD
COUNTY
179 South Street
Roxbury, CT 06783
 
Listing courtesy of Kathryn Clair of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 948-5255
16 Jonathan Drive Roxbury CT 06783
Price Change - 3 weeks ago
1 / 33
$950,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,028
SQFT
16 Jonathan Drive
Roxbury, CT 06783
 
Listing courtesy of Joyce Drakeley of Drakeley Real Estate, Inc. Office Phone: (203) 263-4336 Broker Contact: (203) 449-3568
137 Davenport Road Roxbury CT 06783
New Listing - yesterday
1 / 5
$950,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,614
SQFT
137 Davenport Road
Roxbury, CT 06783
 
Listing courtesy of Lisa Provino of The Provino Group LLC Office Phone: (203) 241-4550 Broker Contact: (203) 241-4550
50 Southbury Road Roxbury CT 06783
1 / 31
$950,000
Single Family Residence For Sale
Active
5
BEDS
3
TOTAL BATHS
2,000
SQFT
50 Southbury Road
Roxbury, CT 06783
 
Listing courtesy of Jeffrey Phillips of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (917) 284-8276
Lot 7 & Lot 8 Willow Brook Drive Roxbury CT 06783
New Listing - 3 weeks on site
1 / 12
$949,000
Land For Sale
Active
20.13
ACRES
LITCHFIELD
COUNTY
Lot 7 & Lot 8 Willow Brook Drive
Roxbury, CT 06783
 
Listing courtesy of Ryan Bollard of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 942-4161
242 Tophet Road Roxbury CT 06783
1 / 25
$799,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,862
SQFT
242 Tophet Road
Roxbury, CT 06783
 
Listing courtesy of Kathryn Clair of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 948-5255
38 West Mountain Lane Roxbury CT 06783
1 / 26
$795,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,336
SQFT
38 West Mountain Lane
Roxbury, CT 06783
 
Listing courtesy of Maria Taylor of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (203) 578-0397
204 North Street Lot 3 Roxbury CT 06783
1 / 16
$775,000
Land For Sale
Active
26.68
ACRES
LITCHFIELD
COUNTY
204 North Street Lot 3
Roxbury, CT 06783
 
Listing courtesy of Jill Sloane of Brown Harris Stevens Office Phone: (203) 655-1418 Broker Contact: (917) 509-7205
216 Baker Road Roxbury CT 06783
1 / 33
$689,000
Single Family Residence For Sale
Active
4
BEDS
2
TOTAL BATHS
2,008
SQFT
216 Baker Road
Roxbury, CT 06783
 
Listing courtesy of David Landau of RE/MAX Right Choice Office Phone: (203) 426-4004 Broker Contact: (203) 948-2703
200 North Street Roxbury CT 06783
1 / 20
$499,000
Land For Sale
Active
8.64
ACRES
LITCHFIELD
COUNTY
200 North Street
Roxbury, CT 06783
 
Listing courtesy of Jill Sloane of Brown Harris Stevens Office Phone: (203) 655-1418 Broker Contact: (917) 509-7205
69 Moosehorn Road Roxbury CT 06783
Price Change - 4 weeks ago
1 / 13
$490,000
Land For Sale
Active
24.84
ACRES
LITCHFIELD
COUNTY
69 Moosehorn Road
Roxbury, CT 06783
 
Listing courtesy of Stacey Matthews of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (203) 671-9067
137 Davenport Road Roxbury CT 06783
New Listing - yesterday
1 / 30
$475,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,614
SQFT
137 Davenport Road
Roxbury, CT 06783
 
Listing courtesy of Lisa Provino of The Provino Group LLC Office Phone: (203) 241-4550 Broker Contact: (203) 241-4550
31 Holmes Road Roxbury CT 06783
1 / 10
$450,000
Land For Sale
Active
8.21
ACRES
LITCHFIELD
COUNTY
31 Holmes Road
Roxbury, CT 06783
 
Listing courtesy of Kathryn Bassett of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 841-8161
Lot 1 West Chalybes Road Roxbury CT 06783
New Listing - 3 weeks on site
1 / 5
$399,000
Land For Sale
Active
4.01
ACRES
LITCHFIELD
COUNTY
Lot 1 West Chalybes Road
Roxbury, CT 06783
 
Listing courtesy of Kathryn Clair of William Pitt Sotheby's Int'l Office Phone: (860) 868-6600 Broker Contact: (203) 948-5255
Booth Road Roxbury CT 06783
Price Change - 2 weeks ago
1 / 7
$274,500
Land For Sale
Active
3.02
ACRES
LITCHFIELD
COUNTY
Booth Road
Roxbury, CT 06783
 
Listing courtesy of Sindy Butkus of Klemm Real Estate Inc Office Phone: (203) 263-4040 Broker Contact: (203) 232-3723
307 North Street Roxbury CT 06783
New Listing - 2 weeks on site
1 / 8
$250,000
Land For Sale
Active
3
ACRES
LITCHFIELD
COUNTY
307 North Street
Roxbury, CT 06783
 
Listing courtesy of Sindy Butkus of Klemm Real Estate Inc Office Phone: (203) 263-4040 Broker Contact: (203) 232-3723
34 Old Roxbury Road Roxbury CT 06783
1 / 29
$35,000
Single Family Residence For Rent
Active
4
BEDS
6
TOTAL BATHS
3,996
SQFT
34 Old Roxbury Road
Roxbury, CT 06783
 
Listing courtesy of Stacey Matthews of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (203) 671-9067
33 Sentry Hill Road Roxbury CT 06783
1 / 29
$30,900
Single Family Residence For Rent
Active
6
BEDS
4
TOTAL BATHS
2,716
SQFT
33 Sentry Hill Road
Roxbury, CT 06783
 
Listing courtesy of Peter Klemm of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 864-4940
45 Moosehorn Road Roxbury CT 06783
1 / 22
$30,900
Single Family Residence For Rent
Active
3
BEDS
4
TOTAL BATHS
4,517
SQFT
45 Moosehorn Road
Roxbury, CT 06783
 
Listing courtesy of Peter Klemm of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 864-4940
23 Painter Hill Road Roxbury CT 06783
1 / 25
$26,900
Single Family Residence For Rent
Active
4
BEDS
3
TOTAL BATHS
1,782
SQFT
23 Painter Hill Road
Roxbury, CT 06783
 
Listing courtesy of Peter Klemm of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 864-4940
 Roxbury CT 06783
1 / 33
$24,900
Single Family Residence For Rent
Active
3
BEDS
3
TOTAL BATHS
2,080
SQFT

Roxbury, CT 06783
 
Listing courtesy of Peter Klemm of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 864-4940
5 North Street Roxbury CT 06783
Price Change - 4 weeks ago
1 / 28
$16,500
Single Family Residence For Rent
Active
4
BEDS
3
TOTAL BATHS
3,089
SQFT
5 North Street
Roxbury, CT 06783
 
Listing courtesy of Melinda Dubow of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 445-4806
34 Old Roxbury Road Roxbury CT 06783
1 / 27
$15,000
Single Family Residence For Rent
Active
4
BEDS
6
TOTAL BATHS
3,996
SQFT
34 Old Roxbury Road
Roxbury, CT 06783
 
Listing courtesy of Stacey Matthews of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (203) 671-9067
24 Old Roxbury Road Roxbury CT 06783
1 / 38
$15,000
Single Family Residence For Rent
Active
3
BEDS
4
TOTAL BATHS
2,562
SQFT
24 Old Roxbury Road
Roxbury, CT 06783
 
Listing courtesy of Stacey Matthews of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (203) 671-9067
18 Bear Burrow Road Roxbury CT 06783
1 / 17
$7,500
Single Family Residence For Rent
Active
4
BEDS
3
TOTAL BATHS
3,026
SQFT
18 Bear Burrow Road
Roxbury, CT 06783
 
Listing courtesy of Maria Taylor of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (203) 578-0397
7 Lower County Road Roxbury CT 06783
Price Change - 4 days ago
1 / 40
$7,500
Single Family Residence For Rent
Active
3
BEDS
2
TOTAL BATHS
2,568
SQFT
7 Lower County Road
Roxbury, CT 06783
 
Listing courtesy of Christopher Haggerty of Compass Connecticut, LLC Office Phone: (203) 200-0851 Broker Contact: (203) 948-8011
10 Sentry Hill Road Roxbury CT 06783
1 / 28
$6,000
Single Family Residence For Rent
Active
4
BEDS
3
TOTAL BATHS
1,260
SQFT
10 Sentry Hill Road
Roxbury, CT 06783
 
Listing courtesy of Melinda Dubow of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 445-4806
160A North Street Roxbury CT 06783
1 / 14
$2,500
Apartment For Rent
Active
1
BED
1
TOTAL BATH
875
SQFT
160A North Street
Roxbury, CT 06783
 
Listing courtesy of Rebecca Doh of W. Raveis Lifestyles Realty Office Phone: (860) 868-0511 Broker Contact: (860) 601-4406
10 (LOWER) Sentry Hill Road Roxbury CT 06783
1 / 8
$2,200
Single Family Residence For Rent
Active
1
BED
1
TOTAL BATH
1,260
SQFT
10 (LOWER) Sentry Hill Road
Roxbury, CT 06783
 
Listing courtesy of Melinda Dubow of Klemm Real Estate Inc Office Phone: (860) 868-7313 Broker Contact: (917) 445-4806
1 - 57 of 57 listings (57 total matches)


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.
Last checked: 2026-05-11 01:47 PM UTC.


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