Buy
- Middlebury
- Homes for Sale
- Open Houses
- New Homes
- Recently Sold
Rent
- Middlebury
- Apartments for Rent
- Houses for Rent
- Townhomes for Rent
- Post A Rental Listing
Mortgage

Recently Sold Homes in Middlebury, CT

108 homes

Use arrow keys to navigate
SOLD
MAY 8, 2026
$810,000
3 Beds
2.5 Baths
2,190 sqft
18 Deer Run Road,
Middlebury, CT 06762
Real Estate Two
Use arrow keys to navigate
SOLD
MAY 8, 2026
$728,000
4 Beds
3 Baths
3,360 sqft
200 North Farm Road,
Middlebury, CT 06762
Showcase Realty, Inc.
Use arrow keys to navigate
SOLD
MAY 4, 2026
$574,900
5 Beds
2 Baths
1,924 sqft
292 Park Rd Extension,
Middlebury, CT 06762
Eagle Eye Realty PLLC
Use arrow keys to navigate
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
Use arrow keys to navigate
SOLD
APR 29, 2026
$222,500
1 Bed
1 Bath
889 sqft
35 Nutmeg Road Apt D1,
Middlebury, CT 06762
Showcase Realty, Inc.
Use arrow keys to navigate
SOLD
APR 27, 2026
$475,000
3 Beds
3.5 Baths
1,918 sqft
637 Watertown Road,
Middlebury, CT 06762
BHGRE Gaetano Marra Homes
Use arrow keys to navigate
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
SOLD
MAR 11, 2026
$170,000
2 Beds
1 Bath
676 sqft
327 Steinmann Ave,
Middlebury, CT 06762
SOLD
MAR 3, 2026
$699,900
3 Beds
2 Baths
1,877 sqft
14 Deer Run Road,
Middlebury, CT 06762
Real Estate Two
SOLD
MAR 2, 2026
$545,000
3 Beds
3.5 Baths
2,403 sqft
2 Dogwood Ct,
Middlebury, CT 06762
SOLD
FEB 27, 2026
$709,900
3 Beds
2.5 Baths
2,190 sqft
2 Deer Run Road,
Middlebury, CT 06762
Real Estate Two
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 23, 2026
$310,000
2 Beds
1 Bath
1,157 sqft
587 Shadduck Road,
Middlebury, CT 06762
Dave Jones Realty, LLC
SOLD
FEB 11, 2026
$461,000
3 Beds
1 Bath
1,120 sqft
11 Upper Whittemore Road,
Middlebury, CT 06762
Real Broker CT, LLC
SOLD
FEB 11, 2026
$895,000
4 Beds
4.5 Baths
3,220 sqft
383 Leonard Road,
Middlebury, CT 06762
William Raveis Real Estate
SOLD
FEB 11, 2026
$799,200
Studio
12 Pine Rdg,
Middlebury, CT 06762
SOLD
FEB 4, 2026
$135,000
15 Deer Run Rd,
Middlebury, CT 06762
SOLD
JAN 30, 2026
$360,000
2 Beds
1 Bath
768 sqft
348 Kelly Road,
Middlebury, CT 06762
Dave Jones Realty, LLC
SOLD
JAN 29, 2026
$585,000
3 Beds
1.5 Baths
2,531 sqft
126 Colonial Avenue,
Middlebury, CT 06762
BHGRE Gaetano Marra Homes
SOLD
JAN 27, 2026
$645,000
4 Beds
3.5 Baths
3,244 sqft
51 Cross Road,
Middlebury, CT 06762
BHGRE Gaetano Marra Homes
SOLD
JAN 22, 2026
$435,000
4 Beds
2 Baths
1,904 sqft
62 Nick Rd,
Middlebury, CT 06762
SOLD
JAN 20, 2026
$100,000
381 Lake Shore Dr,
Middlebury, CT 06762
SOLD
JAN 16, 2026
$300,000
2 Beds
2 Baths
1,099 sqft
73 Yale Avenue,
Middlebury, CT 06762
Manzi Real Estate
SOLD
JAN 15, 2026
$4,050,000
6 Beds
4 Baths
5,816 sqft
7 Sandy Beach Road,
Middlebury, CT 06762
William Pitt Sotheby's Int'l
SOLD
JAN 15, 2026
$565,000
3 Beds
2.5 Baths
2,130 sqft
27 Winding Trl,
Middlebury, CT 06762
SOLD
JAN 14, 2026
$390,000
3 Beds
2 Baths
1,861 sqft
32 Yale Avenue,
Middlebury, CT 06762
Coldwell Banker Realty
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 7, 2026
$85,000
440 Lake Shore Drive,
Middlebury, CT 06762
W. Raveis Lifestyles Realty
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 22, 2025
$400,000
5 Beds
2 Baths
2,023 sqft
140 Yale Ave,
Middlebury, CT 06762

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.