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Recently Sold Homes in Middlebury, CT

126 homes

SOLD
JUN 23, 2026
$554,000
3 Beds
3 Baths
2,403 sqft
24 Ridgewood Dr,
Middlebury, CT 06762
SOLD
JUN 22, 2026
$560,000
2 Beds
3 Baths
1,802 sqft
24 Highridge Rd,
Middlebury, CT 06762
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SOLD
JUN 22, 2026
$554,000
3 Beds
3.5 Baths
2,879 sqft
24 Ridgewood Drive #24,
Middlebury, CT 06762
Real Estate Two
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SOLD
JUN 19, 2026
$560,000
3 Beds
2.5 Baths
1,802 sqft
24 Highridge Road #24,
Middlebury, CT 06762
Serhant Connecticut, LLC
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SOLD
JUN 18, 2026
$500,000
3 Beds
2.5 Baths
2,500 sqft
283 Whittemore Road,
Middlebury, CT 06762
RE/MAX Heritage
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SOLD
JUN 17, 2026
$465,000
3 Beds
3 Baths
1,600 sqft
541 Benson Road,
Middlebury, CT 06762
Joseph Martino Real Estate
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SOLD
JUN 15, 2026
$500,000
2 Beds
2 Baths
1,068 sqft
Address Not Disclosed,
Middlebury, CT 06762
SOLD
JUN 15, 2026
$875,000
3 Beds
2.5 Baths
2,990 sqft
245 Upper Whittemore Road,
Middlebury, CT 06762
BHGRE Gaetano Marra Homes
SOLD
JUN 12, 2026
$569,500
3 Beds
2.5 Baths
2,295 sqft
1 Arrowwood Court #1,
Middlebury, CT 06762
BHGRE Gaetano Marra Homes
SOLD
JUN 8, 2026
$675,000
4 Beds
4 Baths
3,254 sqft
84 Munson Road,
Middlebury, CT 06762
Dorrance Realty
SOLD
JUN 5, 2026
$207,500
1 Bed
1 Bath
889 sqft
35 Nutmeg Rd #A4,
Middlebury, CT 06762
SOLD
JUN 5, 2026
$398,000
3 Beds
2 Baths
1,296 sqft
107 Joy Rd,
Middlebury, CT 06762
SOLD
MAY 29, 2026
$300,000
3 Beds
2 Baths
1,440 sqft
314 Porter Avenue,
Middlebury, CT 06762
Coldwell Banker Realty
SOLD
MAY 29, 2026
$444,000
3 Beds
1.5 Baths
1,456 sqft
863 Whittemore Road,
Middlebury, CT 06762
West View Properties, LLC
SOLD
MAY 28, 2026
$620,000
3 Beds
2.5 Baths
2,658 sqft
193 Ridgewood Drive #193,
Middlebury, CT 06762
Drakeley Real Estate, Inc.
SOLD
MAY 27, 2026
$750,000
4 Beds
2.5 Baths
3,198 sqft
366 Charcoal Avenue,
Middlebury, CT 06762
Lamacchia Realty
SOLD
MAY 22, 2026
$510,000
3 Beds
2 Baths
1,780 sqft
38 East Ridge Drive,
Middlebury, CT 06762
Evjen Agency
SOLD
MAY 22, 2026
$315,000
3 Beds
3 Baths
1,752 sqft
305 Washington Dr,
Middlebury, CT 06762
SOLD
MAY 21, 2026
$435,000
4 Beds
2 Baths
1,422 sqft
192 Breakneck Hill Road,
Middlebury, CT 06762
RE/MAX RISE
SOLD
MAY 21, 2026
$375,000
3 Beds
2 Baths
1,302 sqft
243 Porter Ave,
Middlebury, CT 06762
SOLD
MAY 20, 2026
$435,000
3 Beds
1.5 Baths
1,288 sqft
271 Shadduck Road,
Middlebury, CT 06762
Houlihan Lawrence
SOLD
MAY 18, 2026
$495,650
3 Beds
1.5 Baths
1,492 sqft
18 Freedom Road,
Middlebury, CT 06762
Showcase Realty, Inc.
SOLD
MAY 8, 2026
$810,000
3 Beds
2.5 Baths
2,190 sqft
18 Deer Run Road,
Middlebury, CT 06762
Real Estate Two
SOLD
MAY 8, 2026
$728,000
4 Beds
3 Baths
3,360 sqft
200 North Farm Road,
Middlebury, CT 06762
Showcase Realty, Inc.
SOLD
MAY 4, 2026
$574,900
5 Beds
2 Baths
1,924 sqft
292 Park Rd Extension,
Middlebury, CT 06762
Eagle Eye Realty PLLC
SOLD
MAY 1, 2026
$599,900
2 Beds
1.5 Baths
1,749 sqft
428 Breakneck Hill Road,
Middlebury, CT 06762
BHGRE Gaetano Marra Homes
SOLD
APR 29, 2026
$222,500
1 Bed
1 Bath
889 sqft
35 Nutmeg Road Apt D1,
Middlebury, CT 06762
Showcase Realty, Inc.
SOLD
APR 27, 2026
$475,000
3 Beds
3.5 Baths
1,918 sqft
637 Watertown Road,
Middlebury, CT 06762
BHGRE Gaetano Marra Homes
SOLD
APR 22, 2026
$403,875
3 Beds
3 Baths
2,710 sqft
86 Fairhaven Dr,
Middlebury, CT 06762
SOLD
APR 22, 2026
$190,000
3 Beds
2 Baths
2,375 sqft
288 Watertown Rd,
Middlebury, CT 06762
SOLD
APR 21, 2026
$600,000
4 Beds
3 Baths
2,878 sqft
72 Carriage Drive,
Middlebury, CT 06762
Century 21 Bette Real Estate
SOLD
APR 21, 2026
$190,000
2,376 sqft
288 Watertown Road Lot 5,
Middlebury, CT 06762
Showcase Realty, Inc.
SOLD
APR 16, 2026
$201,927
3 Beds
2 Baths
1,822 sqft
156 Yale Ave,
Middlebury, CT 06762
SOLD
APR 14, 2026
$375,000
2 Beds
1 Bath
1,400 sqft
1292 Straits Tpke,
Middlebury, CT 06762
SOLD
APR 13, 2026
$625,000
3 Beds
2.5 Baths
2,646 sqft
16 Winding Trl,
Middlebury, CT 06762
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 30, 2026
$620,000
3 Beds
2.5 Baths
1,722 sqft
3 Hunting Ridge Road,
Middlebury, CT 06762
Real Estate Two
SOLD
MAR 26, 2026
$430,874
2 Beds
2 Baths
2,011 sqft
13 Caveson Ct,
Middlebury, CT 06762
SOLD
MAR 24, 2026
$530,000
2 Beds
2 Baths
2,011 sqft
13 Caveson Court #13,
Middlebury, CT 06762
Gina Jacobs Real Estate
SOLD
MAR 12, 2026
$66,261
5 Beds
4 Baths
3,106 sqft
428 Benson Road,
Middlebury, CT 06762
Regency Real Estate, LLC

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