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Homes Recently Sold in Middlebury, CT | Page 2

243 Homes
 
587 Shadduck Rd, Middlebury, CT 06762
  • $310,000
  • 2Bd
  • 1Ba
  • 1,157 Sq Ft
SOLD
383 Leonard Rd, Middlebury, CT 06762
  • $895,000
  • 4Bd
  • 5Ba
  • 3,220 Sq Ft
SOLD
348 Kelly Rd, Middlebury, CT 06762
  • $360,000
  • 2Bd
  • 1Ba
  • 768 Sq Ft
SOLD
51 Cross Rd, Middlebury, CT 06762
  • $645,000
  • 4Bd
  • 4Ba
  • 3,244 Sq Ft
SOLD
73 Yale Ave, Middlebury, CT 06762
  • $300,000
  • 2Bd
  • 2Ba
  • 1,099 Sq Ft
SOLD
440 Lake Shore Dr, Middlebury, CT 06762
  • $85,000
  • 0.45 Acre
SOLD
23 Caveson Ct #23, Middlebury, CT 06762
  • $565,000
  • 3Bd
  • 3Ba
  • 2,547 Sq Ft
SOLD
182 Bayberry Ter, Middlebury, CT 06762
  • $495,000
  • 4Bd
  • 2Ba
  • 2,302 Sq Ft
SOLD
111 Dwyer Rd, Middlebury, CT 06762
  • $710,000
  • 3Bd
  • 3Ba
  • 3,212 Sq Ft
SOLD
11 Hunting Ridge Rd, Middlebury, CT 06762
  • $820,000
  • 4Bd
  • 3Ba
  • 2,700 Sq Ft
SOLD
1 Hampshire Ct, Middlebury, CT 06762
  • $800,000
  • 4Bd
  • 4Ba
  • 3,711 Sq Ft
SOLD
116 Yale Ave, Middlebury, CT 06762
  • $495,000
  • 3Bd
  • 3Ba
  • 2,311 Sq Ft
SOLD
18 Winding Trl #18, Middlebury, CT 06762
  • $695,000
  • 3Bd
  • 5Ba
  • 4,051 Sq Ft
SOLD
190 Allerton Farms Rd, Middlebury, CT 06762
  • $449,900
  • 2Bd
  • 3Ba
  • 1,744 Sq Ft
SOLD
18 E Ridge Dr, Middlebury, CT 06762
  • $456,000
  • 3Bd
  • 3Ba
  • 1,340 Sq Ft
SOLD
3 Pommel Ln #3, Middlebury, CT 06762
  • $238,700
  • 2Bd
  • 2Ba
  • 1,136 Sq Ft
SOLD
30 Nick Rd, Middlebury, CT 06762
  • $480,000
  • 3Bd
  • 3Ba
  • 2,496 Sq Ft
SOLD
north benson road, Middlebury, CT 06762
  • $549,936
  • 3Bd
  • 3Ba
  • 2,252 Sq Ft
SOLD
north benson road, Middlebury, CT 06762
  • $530,328
  • 3Bd
  • 3Ba
  • 1,950 Sq Ft
SOLD
82 Tucker Hill Rd, Middlebury, CT 06762
  • $304,150
  • 3Bd
  • 2Ba
  • 941 Sq Ft
SOLD
8 Kimberwick Ct #8, Middlebury, CT 06762
  • $520,000
  • 3Bd
  • 3Ba
  • 2,147 Sq Ft
SOLD
north benson road, Middlebury, CT 06762
  • $505,834
  • 3Bd
  • 3Ba
  • 1,950 Sq Ft
SOLD
288 Watertown Rd #LOT 2, Middlebury, CT 06762
  • $240,000
  • 4 Acre
SOLD
north benson road, Middlebury, CT 06762
  • $593,360
  • 3Bd
  • 3Ba
  • 1,950 Sq Ft
SOLD
north benson road, Middlebury, CT 06762
  • $541,566
  • 3Bd
  • 3Ba
  • 2,206 Sq Ft
SOLD
north benson road, Middlebury, CT 06762
  • $511,000
  • 3Bd
  • 3Ba
  • 1,950 Sq Ft
SOLD
north benson road, Middlebury, CT 06762
  • $499,900
  • 3Bd
  • 3Ba
  • 1,950 Sq Ft
SOLD
181 Ridgewood Dr #181, Middlebury, CT 06762
  • $565,000
  • 3Bd
  • 3Ba
  • 2,614 Sq Ft
SOLD
171 Judd Hill Rd, Middlebury, CT 06762
  • $882,500
  • 5Bd
  • 4Ba
  • 3,700 Sq Ft
SOLD
288 Watertown Rd #LOT 4, Middlebury, CT 06762
  • $225,000
  • 3.32 Acre
SOLD
55 Westwood Dr, Middlebury, CT 06762
  • $675,000
  • 4Bd
  • 3Ba
  • 2,570 Sq Ft
SOLD
288 Watertown Rd #LOT 3, Middlebury, CT 06762
  • $225,000
  • 3.07 Acre
SOLD
76 Three Mile Hill Rd, Middlebury, CT 06762
  • $536,000
  • 4Bd
  • 3Ba
  • 2,088 Sq Ft
SOLD
101 Shadduck Rd, Middlebury, CT 06762
  • $485,000
  • 3Bd
  • 2Ba
  • 2,534 Sq Ft
SOLD
north benson road, Middlebury, CT 06762
  • $547,460
  • 3Bd
  • 3Ba
  • 1,950 Sq Ft
SOLD
north benson road, Middlebury, CT 06762
  • $591,251
  • 3Bd
  • 3Ba
  • 2,923 Sq Ft
SOLD
1 Stevens Rd, Middlebury, CT 06762
  • $520,000
  • 3Bd
  • 3Ba
  • 2,248 Sq Ft
SOLD
17 Deer Run Rd, Middlebury, CT 06762
  • $740,000
  • 4Bd
  • 3Ba
  • 2,466 Sq Ft
SOLD
190 Bronson Dr, Middlebury, CT 06762
  • $690,000
  • 4Bd
  • 3Ba
  • 2,850 Sq Ft
SOLD
222 Crest Rd, Middlebury, CT 06762
  • $730,000
  • 5Bd
  • 3Ba
  • 2,442 Sq Ft
SOLD
1440 Straits Tpke, Middlebury, CT 06762
  • $505,000
  • 3Bd
  • 3Ba
  • 2,046 Sq Ft
SOLD
1 Chatham Ct #1, Middlebury, CT 06762
  • $620,000
  • 4Bd
  • 3Ba
  • 2,950 Sq Ft
SOLD
405 Chestnut Cir #77, Middlebury, CT 06762
  • $649,500
  • 2Bd
  • 3Ba
  • 2,292 Sq Ft
SOLD
17 Highridge Rd #17, Middlebury, CT 06762
  • $515,000
  • 3Bd
  • 3Ba
  • 1,882 Sq Ft
SOLD
34 Avalon Dr, Middlebury, CT 06762
  • $750,000
  • 3Bd
  • 4Ba
  • 3,374 Sq Ft
SOLD
39 Ridgewood Dr #39, Middlebury, CT 06762
  • $540,000
  • 3Bd
  • 3Ba
  • 2,122 Sq Ft
SOLD
593 Park Road Ext, Middlebury, CT 06762
  • $950,000
  • 4Bd
  • 4Ba
  • 4,496 Sq Ft
SOLD
116 Bronson Dr, Middlebury, CT 06762
  • $610,000
  • 3Bd
  • 3Ba
  • 2,262 Sq Ft
SOLD
94 Upper Whittemore Rd, Middlebury, CT 06762
  • $555,000
  • 3Bd
  • 2Ba
  • 2,024 Sq Ft
SOLD
69 Nick Rd, Middlebury, CT 06762
  • $440,000
  • 3Bd
  • 3Ba
  • 1,414 Sq Ft
SOLD
51 - 100 of 243 Homes in Middlebury, CT
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Middlebury, CT real estate market trends

Statistics as of October 2026
$574K
Avg. list price
$260/Sqft
Avg. price/sqft
86
Homes for sale
2,206 Sqft
Avg. home size
39 Days
Avg. days on market
Movoto makes it easy to track market trends in Middlebury, CT. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Middlebury, CT?
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