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Connecticut · Real Estate

Homes for Sale in
Middlebury, CT

There are currently 23 homes for sale in Middlebury, Connecticut with an average list price of $781,895.

Middlebury is a small New Haven County town of about 7,600 situated between Waterbury and Southbury with easy I-84 access. Quassy Amusement Park, on Lake Quassapaug, is a beloved family destination. The town offers suburban-quality schools, well-maintained neighborhoods, and a more affordable price point than neighboring Southbury. A solid, practical choice in the I-84 corridor.

For Sale

23

active listings

Avg. Sale Price

$582K

$85K–$4.1M

Avg. Size Sold

2,228 sf

last 12 mo

vs. Ask Price

-0.8%

avg. paid vs. ask

Stats based on 113 closings in the last 12 months

Showing 12 of 23 listings in Middlebury

863 Whittemore Road, Middlebury, CT
Active
$399,900
3 bd · 2.00 ba · 1,456 sqft
863 Whittemore Road
Middlebury, CT 06762
West View Properties, LLC SmartMLS
397 White Deer Rock Road, Middlebury, CT
Active
$2,195,000
3 bd · 3.00 ba · 3,863 sqft
397 White Deer Rock Road
Middlebury, CT 06762
Klemm Real Estate Inc SmartMLS
700 Watertown Road, Middlebury, CT
Active
$649,000
5 bd · 3.00 ba · 2,528 sqft
700 Watertown Road
Middlebury, CT 06762
Regall Realty, LLC SmartMLS
283 Whittemore Road, Middlebury, CT
Active
$529,000
3 bd · 3.00 ba · 2,500 sqft
283 Whittemore Road
Middlebury, CT 06762
RE/MAX Heritage SmartMLS
301 Steinmann Avenue, Middlebury, CT
Active
$429,900
3 bd · 2.00 ba · 1,572 sqft
301 Steinmann Avenue
Middlebury, CT 06762
Coldwell Banker Realty SmartMLS
90 Fenn Road, Middlebury, CT
Active Open House 5/17 · 12pm–2pm
$699,900
4 bd · 4.00 ba · 3,162 sqft
90 Fenn Road
Middlebury, CT 06762
BHGRE Gaetano Marra Homes SmartMLS
1140 Southford Road, Middlebury, CT
Active
$399,000
Commercial Land
1140 Southford Road
Middlebury, CT 06762
Ghent Realty Advisors SmartMLS
20 Hunting Ridge Road, Middlebury, CT
Active
$774,900
3 bd · 2.00 ba · 1,877 sqft
20 Hunting Ridge Road
Middlebury, CT 06762
Real Estate Two SmartMLS
Lot 41 Somerset Drive, Middlebury, CT
Active
$939,000
3 bd · 3.00 ba · 2,878 sqft
Lot 41 Somerset Drive
Middlebury, CT 06762
BHGRE Gaetano Marra Homes SmartMLS
70 Pine Hollow Drive, Middlebury, CT
Active
$690,000
3 bd · 3.00 ba · 2,734 sqft
70 Pine Hollow Drive
Middlebury, CT 06762
Regency Real Estate, LLC SmartMLS
321 Artillery Road, Middlebury, CT
Active
$729,990
4 bd · 3.00 ba · 3,300 sqft
321 Artillery Road
Middlebury, CT 06762
William Raveis Real Estate SmartMLS
775 South Street, Middlebury, CT
Active
$2,850,000
8 bd · 8.00 ba · 9,619 sqft
775 South Street
Middlebury, CT 06762
Coldwell Banker Realty SmartMLS
See All 23 Homes in Middlebury

Buying a Home in Middlebury, CT

Current Market Snapshot

Entry Price
$225K
lowest listed
Avg. Price
$782K
list price
Top of Market
$2.9M
highest listed
Listings by Bedroom Count
2 beds
1
3 beds
10
4 beds
6
5 beds
2
8 beds
1
Property Types Available
Single Family · 18 Land · 3 Multi-Family For Sale · 1 Condo / Co-Op · 1

The Middlebury real estate market currently has 23 active listings with an average list price of $781,895 and a price range from $224,900 to $2,850,000. Single Family homes make up the largest share of available inventory. Most listings are 3-bedroom homes. The average home size is 2,553 sq ft. All listings are sourced directly from SmartMLS and updated every 15 minutes.

Frequently Asked Questions

How many homes are for sale in Middlebury, CT right now?
As of May 2026, there are 23 active listings in Middlebury, CT. All listings are updated every 15 minutes directly from SmartMLS.
What is the average home price in Middlebury, CT?
The average list price in Middlebury is $781,895. Homes currently range from $224,900 to $2,850,000.
What size homes are most common in Middlebury, CT?
The most common listing in Middlebury is a 3-bedroom home (10 listings). Other common sizes include 4-bedroom (6) and 5-bedroom (2). The average home size is 2,553 sq ft.
What types of homes are available in Middlebury, CT?
Current listings in Middlebury include: Single Family (18), Land (3), Multi-Family For Sale (1), Condo / Co-Op (1).
Is Middlebury, CT a good place to buy a home?
Middlebury is a small New Haven County town of about 7,600 situated between Waterbury and Southbury with easy I-84 access. Quassy Amusement Park, on Lake Quassapaug, is a beloved family destination. The town offers suburban-quality schools, well-maintained neighborhoods, and a more affordable price point than neighboring Southbury. A solid, practical choice in the I-84 corridor.
Does RYZE Realty Group serve Middlebury, CT?
Yes — RYZE Realty Group is a Connecticut real estate team serving buyers and sellers across Connecticut County and the greater Connecticut market, including Middlebury. Contact us for a free consultation.