Middlebury, CT Real Estate Market Report: Price Trends and Data Analysis

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Address Beds Baths Living ft2 List Price Cost per ft2 DOM
775 South St 8 8 9,619 $2,850,000 $296 206 days
397 White Deer Rock Rd 3 3 3,863 $2,195,000 $568 134 days
67 Abbott Farms Rd 4 4 5,237 $1,399,900 $267 22 days
135 Washington Dr 4 4 3,485 $999,000 $286 13 days
9 Whitehall Ct 4 5 4,261 $979,900 $229 1 day
552 Breakneck Hill Rd 5 4 4,114 $950,000 $230 31 days
25 Avalon Dr 3 4 3,494 $879,900 $251 87 days
6 Deer Run Rd 3 3 2,190 $849,900 $388 354 days
29 Cambridge Ct 3 3 2,796 $829,900 $296 18 days
18 Hunting Ridge Rd 4 3 2,700 $819,000 $303 10 days
182 Green Hill Rd 4 3 3,038 $779,900 $256 0 days
20 Hunting Ridge Rd 3 2 1,877 $774,900 $412 179 days
117 Crest Rd 4 3 2,753 $750,000 $272 250 days
77 Crest Rd 4 4 2,674 $749,900 $280 33 days
80 Pine Hollow Dr 4 4 2,806 $724,900 $258 171 days
46 Washington Dr 4 4 1,940 $675,000 $347 15 days
10 Curtis Rd 4 3 2,484 $670,000 $269 61 days
90 Fenn Rd 4 4 3,162 $660,000 $208 142 days
70 Pine Hollow Dr 3 3 3,174 $649,900 $204 85 days
168 N Farm Rd 4 4 3,302 $649,900 $196 98 days
16 Caveson Court, Unit 16 3 3 1,957 $600,000 $306 16 days
16 Caveson Court, Unit 16 3 3 1,957 $600,000 $306 16 days
58 Shadduck Rd 3 3 2,360 $599,900 $254 10 days
3 Brookside Dr Unit 3 4 4 4,200 $599,900 $142 259 days
3 Brookside Dr Unit 3 4 4 4,200 $599,900 $142 259 days
700 Watertown Rd 4 3 2,528 $590,000 $233 88 days
66 Artillery Rd 4 4 2,691 $585,000 $217 152 days
2 Northwood Dr 3 3 1,700 $575,000 $338 61 days
123 Northwood Dr 3 3 1,552 $539,000 $347 43 days
323 Watertown Rd 4 3 2,067 $539,000 $260 46 days
4 Kimberwick Ct Unit 4 3 3 2,181 $534,900 $245 66 days
4 Kimberwick Ct Unit 4 3 3 2,181 $534,900 $245 66 days
10 Ridgewood Dr Unit 10 3 3 2,403 $529,900 $220 75 days
326 Lake Shore Dr 3 2 1,568 $520,000 $331 60 days
89 Sandy Beach Road Unit 89 2 1 798 $499,900 $626 11 days
112 Joy Rd 3 2 1,900 $499,900 $263 44 days
251 Lake Shore Dr 3 2 2,568 $499,000 $194 36 days
213 Acme Dr 4 3 1,833 $499,000 $272 68 days
133 Algin Dr 3 3 1,837 $474,900 $258 16 days
47 Middlebury Ter 2 2 1,953 $474,500 $242 45 days
106 Steinmann Ave 4 2 1,630 $469,900 $288 23 days
42 White Ave 3 3 2,112 $449,900 $213 57 days
1140 Southford Rd N/A N/A N/A $399,000 Unknown 168 days
138 Steinmann Ave 3 2 1,466 $350,000 $238 8 days
24 Yale Ave 3 2 1,469 $349,900 $238 42 days
12 Yale Ave 2 1 836 $339,900 $406 52 days
125 Shadduck Rd 2 2 1,008 $324,900 $322 51 days
327 Steinmann Ave 2 1 676 $300,000 $443 4 days
75 Gleneagle Rd N/A N/A N/A $249,900 Unknown 220 days
500 Watertown Rd N/A N/A N/A $229,000 Unknown 32 days
Average: 3.4 3.0 2,572 $674,878 $285 79 days
Viewing 1 - 50 of 51
Viewing 1 - 50 of 51
Address Beds Baths Living ft2 List Price Cost per ft2 DOM
625 Charcoal Ave 3 3 4,236 $945,000 $223 25 days
Lot 41 Somerset 3 3 2,878 $939,000 $326 183 days
19 Deer Run Rd 4 3 3,100 $900,000 $290 165 days
8 Deer Run Rd 3 3 2,450 $839,900 $342 96 days
15 Hunting Ridge Rd 3 3 1,877 $779,900 $415 549 days
3 Pine Ridge, Unit 23 2 3 2,290 $721,000 $314 537 days
179 Burr Hall Rd 4 3 3,938 $675,000 $171 43 days
285 Southford Rd 3 2 2,007 $650,000 $323 15 days
130 Fairhaven Dr 3 3 2,654 $649,900 $244 52 days
North Benson Rd Unit 63 3 3 2,251 $612,553 $272 8 days
North Benson Rd Unit 61 3 3 1,950 $608,700 $312 8 days
North Benson Rd Unit 58 3 3 2,582 $608,000 $235 38 days
North Benson Rd Unit 48 3 3 2,706 $603,780 $223 353 days
North Benson Rd Unit 60 3 3 2,206 $573,584 $260 312 days
North Benson Rd Unit 65 3 3 2,206 $573,572 $260 115 days
North Benson Rd Unit 56 3 3 2,206 $572,000 $259 82 days
North Benson Rd Unit 54 3 3 2,349 $570,600 $242 54 days
North Benson Rd Unit 59 3 3 2,206 $568,564 $257 404 days
North Benson Rd Unit 66 3 3 1,950 $562,350 $288 73 days
North Benson Rd Unit 57 3 3 2,206 $561,271 $254 271 days
North Benson Rd Unit 52 3 3 2,206 $560,753 $254 469 days
North Benson Rd Unit 44 3 3 1,950 $559,250 $286 59 days
North Benson Rd Unit 44 3 3 2,252 $555,888 $246 431 days
85 Blueberry Knls 3 2 2,156 $550,000 $255 30 days
North Benson Rd Unit 55 3 3 2,462 $548,828 $222 523 days
North Benson Rd Unit 62 3 3 2,206 $545,400 $247 219 days
North Benson Rd Unit 64 3 3 2,206 $545,400 $247 562 days
North Benson Rd Unit 49 3 3 1,950 $533,416 $273 486 days
North Benson Rd Unit 45 3 3 1,950 $525,438 $269 513 days
North Benson Rd Unit 51 3 3 1,950 $523,920 $268 402 days
North Benson Rd Unit 46 3 3 1,950 $522,128 $267 481 days
North Benson Rd Unit 53 3 3 1,950 $519,900 $266 523 days
North Benson Rd Unit 47 3 3 2,206 $509,900 $231 471 days
North Benson Rd Unit 50 3 3 1,950 $509,900 $261 396 days
555 Whittemore Rd 4 3 1,855 $449,000 $242 100 days
1252 Straits Tpke 4 1 1,848 $299,900 $162 94 days
Average: 3.1 2.9 2,313 $604,824 $264 255 days
Viewing 1 - 36 of 36
Viewing 1 - 36 of 36
Address Beds Baths Living ft2 List Price Sold Price Cost per ft2 DOM Sold Date
7-11 Sandy Beach Rd 6 4 5,816 $4,100,000 $4,050,000 $696 101 days 1/15/26
82 Mirey Dam Rd 4 3 3,471 $970,000 $975,000 $280 45 days 11/17/25
851 South St 5 3 3,301 $950,000 $937,500 $284 76 days 6/30/26
286 Mirey Dam Rd 4 3 4,451 $975,000 $900,000 $202 41 days 7/9/26
383 Leonard Rd 4 5 3,220 $889,900 $895,000 $277 82 days 2/11/26
171 Judd Hill Rd 5 4 3,700 $899,950 $882,500 $238 98 days 9/25/25
245 Upper Whittemore 3 3 2,990 $815,000 $875,000 $292 60 days 6/15/26
122 Crest Rd 3 3 3,253 $825,000 $850,000 $261 79 days 7/7/26
11 Hunting Ridge Rd 4 3 2,700 $799,900 $820,000 $303 423 days 12/18/25
38 Avalon Dr 3 3 3,217 $779,000 $815,000 $253 51 days 7/29/26
18 Deer Run Rd 3 3 2,190 $799,900 $810,000 $369 346 days 5/8/26
1 Hampshire Ct 4 4 3,711 $829,000 $800,000 $215 99 days 12/16/25
64 Watertown Rd 3 4 4,094 $759,900 $759,900 $185 78 days 6/30/26
366 Charcoal Ave 4 3 3,198 $750,000 $750,000 $234 73 days 5/27/26
28 Hunting Ridge Rd 4 3 2,466 $729,900 $740,000 $300 548 days 9/9/26
200 N Farm Rd 4 4 3,360 $750,000 $728,000 $216 39 days 5/8/26
111 Dwyer Rd 3 3 3,212 $717,000 $710,000 $221 171 days 12/18/25
2 Deer Run Rd 3 3 2,190 $709,900 $709,900 $324 232 days 2/27/26
15 Central Rd 3 3 2,870 $694,900 $706,000 $245 63 days 6/30/26
14 Deer Run Rd 3 2 1,877 $699,000 $699,900 $372 323 days 3/3/26
18 Winding Trail, Unit 18 3 5 4,051 $700,000 $695,000 $171 96 days 11/21/25
84 Munson Rd 4 5 3,254 $689,000 $675,000 $207 161 days 6/8/26
55 Westwood Dr 4 3 2,570 $695,000 $675,000 $262 198 days 9/24/25
36 Independence Cir 4 4 3,512 $650,000 $670,000 $190 74 days 8/31/26
223 Carriage Dr 4 4 2,484 $674,900 $670,000 $269 103 days 6/30/26
117 Periwinkle Dr Unit 117 3 4 3,488 $669,900 $669,900 $192 61 days 11/12/25
200 Northridge Dr 3 3 2,360 $650,000 $650,000 $275 44 days 8/28/26
51 Cross Rd 4 4 3,244 $629,900 $645,000 $198 63 days 1/27/26
1 Independence Cir Unit 1 4 3 3,224 $609,000 $630,000 $195 47 days 7/7/26
10 Pelham Way Unit 10 3 3 2,251 $650,000 $625,000 $277 60 days 6/30/26
16 Winding Trail, Unit 16 3 3 2,646 $625,000 $625,000 $236 37 days 4/10/26
193 Ridgewood Dr Unit 193 3 3 2,658 $649,900 $620,000 $233 51 days 5/28/26
3 Hunting Ridge Rd 3 3 1,722 $629,900 $620,000 $360 39 days 3/30/26
408 Breakneck Hill Rd 2 3 1,848 $625,000 $615,000 $332 77 days 6/29/26
1 Independence Cir Unit 1 4 3 3,224 $620,000 $615,000 $190 153 days 10/30/25
178 Ridgewood Dr Unit 178 3 3 2,414 $639,900 $607,000 $251 45 days 7/7/26
321 Artillery Rd 4 3 3,300 $699,990 $602,500 $182 159 days 8/3/26
72 Carriage Dr 4 3 2,878 $649,900 $600,000 $208 197 days 4/21/26
39 Independence Cir Unit 39 4 4 3,382 $619,900 $600,000 $177 146 days 11/14/25
428 Breakneck Hill Rd 2 2 1,749 $599,900 $599,900 $342 68 days 5/1/26
North Benson Rd Unit 40 3 3 1,950 $509,300 $593,360 $304 278 days 10/10/25
126 Colonial Ave 3 2 2,531 $599,000 $585,000 $231 152 days 1/29/26
36 Highridge Road Unit 36 3 3 1,997 $585,000 $580,000 $290 164 days 9/10/26
2 Arrowwood Ct Unit 2 3 3 2,256 $599,900 $575,000 $254 88 days 7/10/26
1 Dogwood Ct Unit 1 3 4 3,477 $610,000 $575,000 $165 216 days 11/6/25
292 Park Rd Extension 5 2 1,924 $574,900 $574,900 $298 142 days 5/4/26
72 Ridgewood Dr Unit 72 3 3 2,428 $569,900 $569,900 $234 59 days 7/29/26
1 Arrowwood Ct Unit 1 3 3 2,295 $569,500 $569,500 $248 105 days 6/12/26
23 Caveson Court, Unit 23 3 3 2,547 $565,000 $565,000 $221 73 days 1/2/26
27 Winding Trail, Unit 27 3 3 2,680 $565,000 $565,000 $210 89 days 1/14/26
Average: 3.2 2.8 2,347 $592,284 $587,651 $260 127 days
Viewing 1 - 50 of 106
Viewing 1 - 50 of 106

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