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Middlebury, CT
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1 - 50 of 50 listings (50 total matches)
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775 South Street Middlebury CT 06762
New Listing - 2 weeks on site
1 / 40
$2,850,000
Single Family Residence For Sale
Active
8
BEDS
8
TOTAL BATHS
9,619
SQFT
775 South Street
Middlebury, CT 06762
 
Listing courtesy of Kary Apanovitch of Coldwell Banker Realty Office Phone: (203) 264-1400 Broker Contact: (203) 982-2303
0 White Birch Lane Middlebury CT 06762
1 / 5
$1,600,000
Land For Sale
Active
29
ACRES
NEW HAVEN
COUNTY
0 White Birch Lane
Middlebury, CT 06762
Sycamore Place Subdivision
Listing courtesy of Donna Kennedy of Compass Connecticut, LLC Office Phone: (203) 290-2477 Broker Contact: (917) 669-2642
6 Deer Run Road Middlebury CT 06762
1 / 1
$810,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
1,722
SQFT
6 Deer Run Road
Middlebury, CT 06762
Hunting Ridge Estates Subdivision
Listing courtesy of Jodi Dawley of Real Estate Two Office Phone: (203) 926-1122 Broker Contact: (203) 521-2233
18 Deer Run Road Middlebury CT 06762
1 / 1
$799,900
Single Family Residence For Sale
Pending
3
BEDS
3
TOTAL BATHS
1,722
SQFT
18 Deer Run Road
Middlebury, CT 06762
Hunting Ridge Estates Subdivision
Listing courtesy of Jodi Dawley of Real Estate Two Office Phone: (203) 926-1122 Broker Contact: (203) 521-2233
15 Hunting Ridge Road Middlebury CT 06762
1 / 1
$794,900
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
1,722
SQFT
15 Hunting Ridge Road
Middlebury, CT 06762
Hunting Ridge Estates Subdivision
Listing courtesy of Jodi Dawley of Real Estate Two Office Phone: (203) 926-1122 Broker Contact: (203) 521-2233
117 Crest Road Middlebury CT 06762
Open House Sun, Mar 8, 11 AM
Please verify times due to COVID-19
1 / 37
$759,000
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,543
SQFT
117 Crest Road
Middlebury, CT 06762
 
Listing courtesy of Lori Geraci of BHGRE Gaetano Marra Homes Office Phone: (203) 758-1300 Broker Contact: (203) 910-0997
200 North Farm Road Middlebury CT 06762
Price Change - 3 weeks ago
1 / 40
$750,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
3,360
SQFT
200 North Farm Road
Middlebury, CT 06762
 
Listing courtesy of Jackie Desmarais of Showcase Realty, Inc. Office Phone: (860) 274-7000 Broker Contact: (203) 509-6502
28 Hunting Ridge Road Middlebury CT 06762
1 / 1
$739,900
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,704
SQFT
28 Hunting Ridge Road
Middlebury, CT 06762
Hunting Ridge Estates Subdivision
Listing courtesy of Jodi Dawley of Real Estate Two Office Phone: (203) 926-1122 Broker Contact: (203) 521-2233
321 Artillery Road Middlebury CT 06762
Open House Sun, Mar 15, 11 AM
Please verify times due to COVID-19
1 / 1
$729,990
Single Family Residence For Sale
Coming Soon
4
BEDS
3
TOTAL BATHS
3,300
SQFT
321 Artillery Road
Middlebury, CT 06762
 
Listing courtesy of Frank Durante of William Raveis Real Estate Office Phone: (203) 426-3429 Broker Contact: (203) 241-5821
3 Pine Ridge 23 Middlebury CT 06762
1 / 28
$721,000
Condominium For Sale
Pending
2
BEDS
3
TOTAL BATHS
2,290
SQFT
Granite Woods
3 Pine Ridge 23
Middlebury, CT 06762
Listing courtesy of Robert Michaud of Michaud Real Estate Office Phone: (203) 225-0229 Broker Contact: (203) 668-5981
Lots 12,13, 14 Mirey Dam Road Middlebury CT 06762
New Listing - 3 weeks on site
1 / 2
$699,900
Land For Sale
Active
2.31
ACRES
NEW HAVEN
COUNTY
Lots 12,13, 14 Mirey Dam Road
Middlebury, CT 06762
Woodland Estates Subdivision
Listing courtesy of Mary Ann Hebert of BHGRE Gaetano Marra Homes Office Phone: (203) 758-1300 Broker Contact: (203) 592-0186
84 Munson Road Middlebury CT 06762
1 / 40
$689,000
Single Family Residence For Sale
Pending
4
BEDS
5
TOTAL BATHS
3,254
SQFT
84 Munson Road
Middlebury, CT 06762
 
Listing courtesy of Thomas Mele of Dorrance Realty Office Phone: (203) 718-3305 Broker Contact: (203) 718-3305
3 Brookside Drive 3 Middlebury CT 06762
1 / 38
$659,900
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
2,950
SQFT
3 Brookside Drive 3
Middlebury, CT 06762
 
Listing courtesy of Shagufta Zahid of S Factor Realty Group LLC Office Phone: (203) 302-0672 Broker Contact: (203) 558-9101
3 Brookside Drive 3 Middlebury CT 06762
1 / 38
$659,900
Condominium For Sale
Active
4
BEDS
4
TOTAL BATHS
2,950
SQFT
Brookside of Middlebury
3 Brookside Drive 3
Middlebury, CT 06762
Listing courtesy of Shagufta Zahid of S Factor Realty Group LLC Office Phone: (203) 302-0672 Broker Contact: (203) 558-9101
72 Carriage Drive Middlebury CT 06762
1 / 15
$649,900
Single Family Residence For Sale
Active Under Contract
4
BEDS
3
TOTAL BATHS
2,878
SQFT
72 Carriage Drive
Middlebury, CT 06762
 
Listing courtesy of Justin Bette of Century 21 Bette Real Estate Office Phone: (203) 264-2500 Broker Contact: (203) 217-5768
3 Hunting Ridge Road Middlebury CT 06762
New Listing - 2 weeks on site
1 / 38
$629,900
Single Family Residence For Sale
Active Under Contract
3
BEDS
3
TOTAL BATHS
1,722
SQFT
3 Hunting Ridge Road
Middlebury, CT 06762
Hunting Ridge Estates Subdivision
Listing courtesy of Jodi Dawley of Real Estate Two Office Phone: (203) 926-1122 Broker Contact: (203) 521-2233
North Benson Road 48 Middlebury CT 06762
1 / 9
$603,780
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,706
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 48
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
428 Breakneck Hill Road Middlebury CT 06762
New Listing - a week on site
1 / 39
$599,900
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,749
SQFT
428 Breakneck Hill Road
Middlebury, CT 06762
 
Listing courtesy of Mary Ann Hebert of BHGRE Gaetano Marra Homes Office Phone: (203) 758-1300 Broker Contact: (203) 592-0186
10 Old Waterbury Road Middlebury CT 06762
Price Change - 2 weeks ago
1 / 12
$599,900
Quadruplex For Sale
Active
5
BEDS
4
TOTAL BATHS
2,345
SQFT
10 Old Waterbury Road
Middlebury, CT 06762
 
Listing courtesy of Judith Caputo of Advantage Realty Group, Inc. Office Phone: (203) 755-4015 Broker Contact: (203) 755-4015
292 Park Rd Extension Middlebury CT 06762
Price Change - 2 weeks ago
1 / 40
$574,900
Single Family Residence For Sale
Active
5
BEDS
2
TOTAL BATHS
1,924
SQFT
292 Park Rd Extension
Middlebury, CT 06762
 
Listing courtesy of Tammy Ferrauola of Eagle Eye Realty PLLC Office Phone: (860) 263-9102 Broker Contact: (860) 205-5995
24 Ridgewood Drive 24 Middlebury CT 06762
1 / 39
$574,000
Condominium For Sale
Active
3
BEDS
4
TOTAL BATHS
2,403
SQFT
Ridgewood at Middlebury
24 Ridgewood Drive 24
Middlebury, CT 06762
Listing courtesy of Jodi Dawley of Real Estate Two Office Phone: (203) 926-1122 Broker Contact: (203) 521-2233
North Benson Road 60 Middlebury CT 06762
1 / 9
$573,584
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,206
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 60
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
1 Arrowwood Court 1 Middlebury CT 06762
1 / 13
$569,500
Condominium For Sale
Coming Soon
3
BEDS
3
TOTAL BATHS
1,814
SQFT
Ridgewood at Middlebury
1 Arrowwood Court 1
Middlebury, CT 06762
Listing courtesy of Christina Zainc of BHGRE Gaetano Marra Homes Office Phone: (203) 758-1300 Broker Contact: (860) 637-0620
North Benson Road 59 Middlebury CT 06762
1 / 9
$568,564
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,206
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 59
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 57 Middlebury CT 06762
1 / 9
$561,271
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,206
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 57
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 52 Middlebury CT 06762
1 / 9
$560,753
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,206
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 52
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 44 Middlebury CT 06762
1 / 9
$555,888
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,252
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 44
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 55 Middlebury CT 06762
1 / 9
$548,828
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,462
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 55
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 62 Middlebury CT 06762
New Listing - 4 weeks on site
1 / 9
$545,400
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,206
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 62
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 64 Middlebury CT 06762
1 / 9
$545,400
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,206
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 64
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 49 Middlebury CT 06762
1 / 9
$533,416
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
1,950
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 49
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
61 Sandy Hill Road Middlebury CT 06762
1 / 1
$529,900
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,811
SQFT
61 Sandy Hill Road
Middlebury, CT 06762
 
Listing courtesy of Arben Belica of William Raveis Real Estate Office Phone: (203) 264-8180 Broker Contact: (203) 509-4395
North Benson Road 45 Middlebury CT 06762
1 / 9
$525,438
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
1,950
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 45
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 51 Middlebury CT 06762
1 / 9
$523,920
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
1,950
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 51
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 46 Middlebury CT 06762
1 / 9
$522,128
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
1,950
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 46
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 66 Middlebury CT 06762
1 / 9
$522,128
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
1,950
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 66
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 53 Middlebury CT 06762
1 / 9
$519,900
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
1,950
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 53
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 50 Middlebury CT 06762
1 / 9
$509,900
Condominium For Sale
Pending
3
BEDS
3
TOTAL BATHS
1,950
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 50
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
North Benson Road 47 Middlebury CT 06762
1 / 9
$509,900
Condominium For Sale
Active Under Contract
3
BEDS
3
TOTAL BATHS
2,206
SQFT
Aberdeen Estates at Benson Woods
North Benson Road 47
Middlebury, CT 06762
Listing courtesy of Renee Meuse Lovley of Century 21 AllPoints Realty Office Phone: (860) 621-8378 Broker Contact: (860) 227-8320
637 Watertown Road Middlebury CT 06762
Price Change - 2 weeks ago
1 / 40
$450,000
Single Family Residence For Sale
Active Under Contract
3
BEDS
4
TOTAL BATHS
1,918
SQFT
637 Watertown Road
Middlebury, CT 06762
 
Listing courtesy of Jonna Dibble of BHGRE Gaetano Marra Homes Office Phone: (203) 758-1300 Broker Contact: (203) 491-7803
19 Deer Run Road Middlebury CT 06762
1 / 1
$274,900
Land For Sale
Active
3.33
ACRES
NEW HAVEN
COUNTY
19 Deer Run Road
Middlebury, CT 06762
 
Listing courtesy of Jodi Dawley of Real Estate Two Office Phone: (203) 926-1122 Broker Contact: (203) 521-2233
152 Glenwood Avenue Middlebury CT 06762
Real Estate Owned
1 / 19
$259,900
Single Family Residence For Sale
Active
2
BEDS
1
TOTAL BATH
1,085
SQFT
152 Glenwood Avenue
Middlebury, CT 06762
 
Listing courtesy of Donato Orsini of West View Properties, LLC Office Phone: (860) 274-7838 Broker Contact: (203) 808-2791
75 Gleneagle Road Middlebury CT 06762
New Listing - 4 weeks on site
1 / 24
$229,900
Land For Sale
Active
4.67
ACRES
NEW HAVEN
COUNTY
75 Gleneagle Road
Middlebury, CT 06762
Three Mile Hill Estates Subdivision
Listing courtesy of Scott Tedesco of Tedesco Real Estate Office Phone: (203) 509-1215 Broker Contact: (203) 509-1215
35 Nutmeg Road Apt D1 Middlebury CT 06762
1 / 19
$229,000
Condominium For Sale
Active
1
BED
1
TOTAL BATH
889
SQFT
Middlebury Commons
35 Nutmeg Road Apt D1
Middlebury, CT 06762
Listing courtesy of Karen Stanco of Showcase Realty, Inc. Office Phone: (860) 274-7000 Broker Contact: (203) 206-4464
288 Watertown Road Lot 5 Middlebury CT 06762
1 / 6
$200,000
Land For Sale
Pending
2,376
SQFT
288 Watertown Road Lot 5
Middlebury, CT 06762
 
Listing courtesy of John Donato Jr of Showcase Realty, Inc. Office Phone: (860) 274-7000 Broker Contact: (203) 695-4097
Ferndale Avenue Middlebury CT 06762
1 / 4
$75,000
Land For Sale
Pending
1.64
ACRES
NEW HAVEN
COUNTY
Ferndale Avenue
Middlebury, CT 06762
 
Listing courtesy of Ken Demirs of Regency Real Estate, LLC Office Phone: (860) 945-9868 Broker Contact: (860) 483-1107
372 Tucker Hill Road Middlebury CT 06762
1 / 33
$17,000
Single Family Residence For Rent
Active
5
BEDS
7
TOTAL BATHS
6,600
SQFT
372 Tucker Hill Road
Middlebury, CT 06762
 
Listing courtesy of Naima Mazouzi of Eagle Eye Realty PLLC Office Phone: (860) 263-9102 Broker Contact: (860) 754-7651
149 Ridgewood Drive Middlebury CT 06762
1 / 30
$3,950
Condominium For Rent
Pending
3
BEDS
3
TOTAL BATHS
1,814
SQFT
149 Ridgewood Drive
Middlebury, CT 06762
 
Listing courtesy of Nancy Langrock of William Raveis Real Estate Office Phone: (203) 264-8180 Broker Contact: (203) 597-7923
346 Middlebury Road Middlebury CT 06762
1 / 22
$3,000
Single Family Residence For Rent
Pending
3
BEDS
2
TOTAL BATHS
1,286
SQFT
346 Middlebury Road
Middlebury, CT 06762
 
Listing courtesy of Tanya Uhelsky of RE/MAX RISE Office Phone: (203) 806-1435 Broker Contact: (203) 317-9698
1129 Southford Road Middlebury CT 06762
1 / 7
$1,800
Multi Family For Rent
Active
1
BED
1
TOTAL BATH
1,604
SQFT
1129 Southford Road
Middlebury, CT 06762
 
Listing courtesy of Douglas Rose of Scalzo Real Estate Office Phone: (203) 790-7077 Broker Contact: (203) 470-3799
1 - 50 of 50 listings (50 total matches)


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.
Last checked: 2026-03-04 02:42 AM UTC.


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