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Recently Sold Condos in Middlebury, CT

39 homes

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SOLD
APR 29, 2026
$222,500
1 Bed
1 Bath
889 sqft
35 Nutmeg Road Apt D1,
Middlebury, CT 06762
Showcase Realty, Inc.
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SOLD
APR 10, 2026
$625,000
3 Beds
2.5 Baths
2,646 sqft
16 Winding Trail #16,
Middlebury, CT 06762
Home Selling Team
SOLD
MAR 26, 2026
$430,874
2 Beds
2 Baths
2,011 sqft
13 Caveson Ct,
Middlebury, CT 06762
SOLD
FEB 26, 2026
$545,000
3 Beds
3.5 Baths
3,103 sqft
2 Dogwood Court #2,
Middlebury, CT 06762
Serhant Connecticut, LLC
SOLD
FEB 11, 2026
$799,200
Studio
12 Pine Rdg,
Middlebury, CT 06762
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SOLD
JAN 14, 2026
$565,000
3 Beds
2.5 Baths
2,680 sqft
27 Winding Trail #27,
Middlebury, CT 06762
Serhant Connecticut, LLC
SOLD
JAN 5, 2026
$565,000
3 Beds
2.5 Baths
2,547 sqft
23 Caveson Ct,
Middlebury, CT 06762
SOLD
JAN 2, 2026
$565,000
3 Beds
2.5 Baths
2,547 sqft
23 Caveson Court #23,
Middlebury, CT 06762
William Raveis Real Estate
SOLD
DEC 16, 2025
$837,591
Studio
14 Pine Rdg,
Middlebury, CT 06762
SOLD
NOV 26, 2025
$766,526
Studio
13 Pine Rdg,
Middlebury, CT 06762
SOLD
NOV 24, 2025
$695,000
3 Beds
3.5 Baths
2,688 sqft
18 Winding Trl,
Middlebury, CT 06762
SOLD
NOV 21, 2025
$695,000
3 Beds
4 Baths
4,051 sqft
18 Winding Trail #18,
Middlebury, CT 06762
Serhant Connecticut, LLC
SOLD
NOV 17, 2025
$238,700
2 Beds
2 Baths
1,136 sqft
3 Pommel Lane #3,
Middlebury, CT 06762
Showcase Realty, Inc.
SOLD
NOV 14, 2025
$600,000
4 Beds
3 Baths
3,382 sqft
39 Independence Circle #39,
Middlebury, CT 06762
William Raveis Real Estate
SOLD
NOV 12, 2025
$669,900
3 Beds
3 Baths
3,488 sqft
117 Periwinkle Drive #117,
Middlebury, CT 06762
BHGRE Gaetano Marra Homes
SOLD
NOV 12, 2025
$669,900
3 Beds
3 Baths
2,476 sqft
117 Periwinkle Dr,
Middlebury, CT 06762
SOLD
NOV 12, 2025
$805,975
Studio
10 Pine Rdg,
Middlebury, CT 06762
SOLD
NOV 10, 2025
$575,000
3 Beds
3.5 Baths
3,115 sqft
1 Dogwood Ct,
Middlebury, CT 06762
SOLD
NOV 6, 2025
$614,000
Studio
8 Pine Rdg,
Middlebury, CT 06762
SOLD
NOV 6, 2025
$575,000
3 Beds
3.5 Baths
3,477 sqft
1 Dogwood Court #1,
Middlebury, CT 06762
Drakeley Real Estate, Inc.
SOLD
NOV 3, 2025
$530,328
Studio
36 N Benson Rd,
Middlebury, CT 06762
SOLD
OCT 30, 2025
$530,328
3 Beds
2.5 Baths
1,950 sqft
North Benson Road #36,
Middlebury, CT 06762
Century 21 AllPoints Realty
SOLD
OCT 30, 2025
$549,936
3 Beds
2.5 Baths
2,252 sqft
North Benson Road #43,
Middlebury, CT 06762
Century 21 AllPoints Realty
SOLD
OCT 30, 2025
$615,000
4 Beds
2.5 Baths
3,224 sqft
1 Independence Circle #1,
Middlebury, CT 06762
Regency Real Estate, LLC
SOLD
OCT 27, 2025
$520,000
3 Beds
3 Baths
2,147 sqft
8 Kimberwick Ct,
Middlebury, CT 06762
SOLD
OCT 22, 2025
$425,000
2 Beds
1.5 Baths
2,025 sqft
112 Periwinkle Dr,
Middlebury, CT 06762
SOLD
OCT 22, 2025
$520,000
3 Beds
2.5 Baths
2,147 sqft
8 Kimberwick Court #8,
Middlebury, CT 06762
Gina Jacobs Real Estate
SOLD
OCT 22, 2025
$510,000
2 Beds
2.5 Baths
2,593 sqft
112 Periwinkle Drive #112,
Middlebury, CT 06762
BHGRE Gaetano Marra Homes
SOLD
OCT 17, 2025
$699,102
Studio
9 Pine Rdg,
Middlebury, CT 06762
SOLD
OCT 17, 2025
$505,834
3 Beds
2.5 Baths
1,950 sqft
North Benson Road #39,
Middlebury, CT 06762
Century 21 AllPoints Realty
SOLD
OCT 14, 2025
$593,360
Studio
40 N Benson Rd,
Middlebury, CT 06762
SOLD
OCT 10, 2025
$593,360
3 Beds
2.5 Baths
1,950 sqft
North Benson Road #40,
Middlebury, CT 06762
Century 21 AllPoints Realty
SOLD
OCT 7, 2025
$541,566
Studio
41 N Benson Rd,
Middlebury, CT 06762
SOLD
OCT 6, 2025
$541,566
3 Beds
2.5 Baths
2,206 sqft
North Benson Road #41,
Middlebury, CT 06762
Century 21 AllPoints Realty
SOLD
OCT 2, 2025
$511,000
Studio
38 N Benson Rd,
Middlebury, CT 06762
SOLD
OCT 1, 2025
$511,000
3 Beds
2.5 Baths
1,950 sqft
North Benson Road #38,
Middlebury, CT 06762
Century 21 AllPoints Realty
SOLD
SEP 30, 2025
$535,807
Studio
42 N Benson Rd,
Middlebury, CT 06762
SOLD
SEP 30, 2025
$499,900
3 Beds
2.5 Baths
1,950 sqft
North Benson Road #42,
Middlebury, CT 06762
Century 21 AllPoints Realty
SOLD
SEP 25, 2025
$565,000
3 Beds
2.5 Baths
2,614 sqft
181 Ridgewood Drive #181,
Middlebury, CT 06762
Coldwell Banker Realty
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Recently Sold Homes Near Middlebury, CT

We found 30 more homes matching your filters just outside Middlebury

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SOLD
MAY 14, 2026
$210,000
2 Beds
1.5 Baths
1,360 sqft
461 Spring Street #9G,
Naugatuck, CT 06770
Coldwell Banker Realty 2000
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SOLD
MAY 14, 2026
$190,000
2 Beds
1 Bath
800 sqft
18 Bridge Street APT 2C,
Naugatuck, CT 06770
Coldwell Banker Realty 2000
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SOLD
MAY 11, 2026
$210,000
3 Beds
1.5 Baths
1,092 sqft
146 Coach Circle #3,
Naugatuck, CT 06770
Century 21 Scala Group
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SOLD
MAY 8, 2026
$610,000
2 Beds
2 Baths
1,546 sqft
712 Championship Drive #712,
Oxford, CT 06478
Coldwell Banker Realty
SOLD
APR 23, 2026
$145,000
2 Beds
1 Bath
1,088 sqft
55 Porter Ave #6E,
Naugatuck, CT 06770
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SOLD
APR 22, 2026
$145,000
2 Beds
1 Bath
1,088 sqft
55 Porter Avenue #6E,
Naugatuck, CT 06770
Carey & Guarrera Real Estate
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SOLD
APR 22, 2026
$220,000
2 Beds
1.5 Baths
1,330 sqft
925 Oronoke Road #36C,
Waterbury, CT 06708
Showcase Realty, Inc.
SOLD
APR 13, 2026
$175,000
2 Beds
2.5 Baths
1,008 sqft
461 Spring Street APT 3B,
Naugatuck, CT 06770
mygoodagent
SOLD
APR 13, 2026
$175,000
2 Beds
3 Baths
1,008 sqft
461 Spring St #3B,
Naugatuck, CT 06770
SOLD
APR 8, 2026
$235,000
2 Beds
1.5 Baths
1,330 sqft
925 Oronoke Road #11D,
Waterbury, CT 06708
THE CONNECTICUT AGENCY LLC
SOLD
APR 8, 2026
$190,000
2 Beds
1.5 Baths
1,125 sqft
1385 Highland Avenue #13B,
Waterbury, CT 06708
William Raveis Real Estate
SOLD
APR 2, 2026
$230,000
2 Beds
1.5 Baths
1,088 sqft
240 Wesley Street APT 4,
Waterbury, CT 06708
Rockoff Realty
SOLD
APR 1, 2026
$600,000
2 Beds
2 Baths
1,532 sqft
709 Championship Dr,
Oxford, CT 06478
SOLD
MAR 31, 2026
$80,000
1 Bed
1 Bath
620 sqft
215 Waterville St #4,
Waterbury, CT 06710
SOLD
MAR 31, 2026
$180,000
2 Beds
1.5 Baths
960 sqft
585 Park Road #5-7,
Waterbury, CT 06708
Fercodini Properties, Inc.
SOLD
MAR 31, 2026
$230,000
2 Beds
1.5 Baths
1,200 sqft
827 Oronoke Road APT 8-2,
Waterbury, CT 06708
KW Legacy Partners
SOLD
MAR 31, 2026
$600,000
2 Beds
2 Baths
1,532 sqft
709 Championship Drive #709,
Oxford, CT 06478
Berkshire Hathaway NE Prop.
SOLD
MAR 26, 2026
$205,222
3 Beds
2.5 Baths
1,732 sqft
30 Coach Circle #1,
Naugatuck, CT 06770
Pepe Realty, Inc
SOLD
MAR 25, 2026
$100,000
1 Bed
1 Bath
620 sqft
215 Waterville St #2,
Waterbury, CT 06710
SOLD
MAR 20, 2026
$239,000
2 Beds
1.5 Baths
1,426 sqft
925 Oronoke Road #38A,
Waterbury, CT 06708
William Raveis Real Estate
SOLD
MAR 20, 2026
$150,000
2 Beds
1 Bath
840 sqft
40 Ridge Rd #3,
Naugatuck, CT 06770
SOLD
MAR 19, 2026
$165,000
2 Beds
1.5 Baths
1,054 sqft
218 Oakville Avenue APT C,
Waterbury, CT 06708
Coldwell Banker Realty
SOLD
MAR 19, 2026
$175,000
2 Beds
1.5 Baths
998 sqft
38 Shirley Street APT 5,
Waterbury, CT 06708
Great Estates, CT
SOLD
MAR 17, 2026
$150,000
2 Beds
1 Bath
840 sqft
40 Ridge Road #3,
Naugatuck, CT 06770
Showcase Realty, Inc.
SOLD
MAR 16, 2026
$250,000
2 Beds
1.5 Baths
1,822 sqft
41 Millville Avenue #201,
Naugatuck, CT 06770
Coldwell Banker Realty 2000
SOLD
MAR 13, 2026
$225,000
2 Beds
1.5 Baths
1,288 sqft
827 Oronoke Road APT 5-1,
Waterbury, CT 06708
William Raveis Real Estate
SOLD
MAR 11, 2026
$200,000
3 Beds
2 Baths
1,092 sqft
50 Round Tree Dr #6,
Naugatuck, CT 06770
SOLD
MAR 2, 2026
$239,000
2 Beds
1.5 Baths
1,426 sqft
925 Oronoke Road #21A,
Waterbury, CT 06708
Coldwell Banker Realty
SOLD
FEB 27, 2026
$208,000
2 Beds
1.5 Baths
1,530 sqft
925 Oronoke Road #17F,
Waterbury, CT 06708
Vitale Realty
SOLD
FEB 26, 2026
$217,500
2 Beds
1.5 Baths
1,125 sqft
1385 Highland Avenue #20A,
Waterbury, CT 06708
Vitale Realty

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