New30$395,000
3 bd · 1 ba · — sqft
25 Southview Avenue, Middlebury, CT
Val Joyce · William Raveis Real Estate
Homes for Sale in Middlebury, CT
Hide MapHomes for Sale in Middlebury, CT
24 of 27 Listings
New30$395,000
3 bd · 1 ba · — sqft
25 Southview Avenue, Middlebury, CT
Val Joyce · William Raveis Real Estate
40$589,900
2 bd · 3 ba · — sqft
203 Sugar Maple Way Unit 203, Middlebury, CT
Amy Wilson · Berkshire Hathaway NE Prop.
Price Reduced40$530,000
2 bd · 3 ba · — sqft
104 Periwinkle Drive Unit 104, Middlebury, CT
Heather Crabtree · RE/MAX RISE
Price Reduced40$530,000
2 bd · 3 ba · — sqft
104 Periwinkle Drive Unit 104, Middlebury, CT
Heather Crabtree · RE/MAX RISE
24$725,000
4 bd · 3 ba · — sqft
106 Mirey Dam Road, Middlebury, CT
Donna Bannon · BHGRE Gaetano Marra Homes
36$725,000
5 bd · 3 ba · — sqft
783 Whittemore Road, Middlebury, CT
Sean Jackson · Keller Williams Realty
21$485,000
3 bd · 2 ba · — sqft
314 Porter Avenue, Middlebury, CT
Derek Greene · Derek Greene
Price Reduced25$499,900
4 bd · 3 ba · — sqft
802 Charcoal Avenue, Middlebury, CT
Donna Bannon · BHGRE Gaetano Marra Homes
1$849,900
3 bd · 3 ba · — sqft
6 Deer Run Road, Middlebury, CT
Jodi Dawley · Real Estate Two
Price Reduced40$850,000
3 bd · 4 ba · 3,024 sqft
25 Juniper Road, Middlebury, CT
Tina Tanushi · Regency Real Estate, LLC
8$995,000
3 bd · 3 ba · 2,878 sqft
294 Christian Road, Middlebury, CT
Jonna Dibble · BHGRE Gaetano Marra Homes
Price Reduced39$699,900
4 bd · 3 ba · 3,038 sqft
182 Green Hill Road, Middlebury, CT
Chris Jahn · Showcase Realty, Inc.
40$979,900
4 bd · 5 ba · 4,261 sqft
9 Whitehall Court, Middlebury, CT
Tracy Wilson · Lamacchia Realty
Price Reduced25$280,000
2 bd · 1 ba · 676 sqft
327 Steinmann Avenue, Middlebury, CT
Harold Zinno · Regency Real Estate, LLC
23$350,000
3 bd · 2 ba · 1,466 sqft
138 Steinmann Avenue, Middlebury, CT
Sarita Conforti · West View Properties, LLC
Price Reduced40$789,900
4 bd · 3 ba · 2,700 sqft
18 Hunting Ridge Road, Middlebury, CT
Robert Disapio · Dave Jones Realty, LLC
4$999,000
4 bd · 4 ba · 3,485 sqft
135 Washington Drive, Middlebury, CT
Arben Demiraj · West View Properties, LLC
Price Reduced38$899,000
5 bd · 4 ba · 4,114 sqft
552 Breakneck Hill Road, Middlebury, CT
Rebecca Doh · W. Raveis Lifestyles Realty
Price Reduced38$699,900
4 bd · 4 ba · 2,674 sqft
77 Crest Road, Middlebury, CT
Michael Vartolone · William Raveis Real Estate
Price Reduced40$474,500
2 bd · 2 ba · 1,953 sqft
47 Middlebury Terrace, Middlebury, CT
Ruthanne Salvatore · Coldwell Banker Realty
30$520,000
3 bd · 2 ba · 1,568 sqft
326 Lake Shore Drive, Middlebury, CT
Lauren Cavallo · Lauren Ashley Homes LLC
Price Reduced32$650,000
4 bd · 3 ba · 2,484 sqft
10 Curtis Road, Middlebury, CT
Heather Dever · Showcase Realty, Inc.
Price Reduced23$619,900
3 bd · 3 ba · 3,174 sqft
70 Pine Hollow Drive, Middlebury, CT
Simonne Corriveau · KW Legacy Partners
Price Reduced40$590,000
4 bd · 3 ba · 2,528 sqft
700 Watertown Road, Middlebury, CT
Erin Giguiere · Regall Realty, LLC
SmartMLSSource: HJN community data
October 2026 · This period is still settling
Selling at 100.0% of asking price
Sales here are closing essentially at asking. MLS · 18 sales · as of Oct 29, 2026