Homes for Sale in Middlebury, CT | RYZE Realty Group
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Connecticut · Real Estate

Homes for Sale in
Middlebury, CT

There are currently 40 homes for sale in Middlebury, Connecticut with an average list price of $667,100.

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

40

active listings

Avg. Sale Price

$581K

$70K–$4.1M

Avg. Size Sold

2,264 sf

last 12 mo

vs. Ask Price

-0.9%

avg. paid vs. ask

Stats based on 116 closings in the last 12 months

Showing 12 of 40 listings in Middlebury

802 Charcoal Avenue, Middlebury, CT
Active
$550,000
4 bd · 3.00 ba · 1,911 sqft
802 Charcoal Avenue
Middlebury, CT 06762
BHGRE Gaetano Marra Homes SmartMLS
85 Ridgewood Drive #85, Middlebury, CT
Active
$650,000
3 bd · 3.00 ba · 2,643 sqft  ·  Condominium
85 Ridgewood Drive #85
Middlebury, CT 06762
Serhant Connecticut, LLC SmartMLS
6 Deer Run Road, Middlebury, CT
Active
$849,900
3 bd · 3.00 ba · 2,190 sqft
6 Deer Run Road
Middlebury, CT 06762
Real Estate Two SmartMLS
25 Juniper Road, Middlebury, CT
Active
$895,000
3 bd · 4.00 ba · 3,024 sqft
25 Juniper Road
Middlebury, CT 06762
Regency Real Estate, LLC SmartMLS
106 Country Club Road, Middlebury, CT
Active OH 9/27 · 11am–1pm
$450,000
4 bd · 3.00 ba · 2,664 sqft
106 Country Club Road
Middlebury, CT 06762
Regency Real Estate, LLC SmartMLS
271 Steinmann Avenue, Middlebury, CT
Active
$139,999
Residential Land
271 Steinmann Avenue
Middlebury, CT 06762
eRealty Advisors, Inc. SmartMLS
10 Old Waterbury Road, Middlebury, CT
Active
$699,900
5 bd · 4.00 ba · 2,345 sqft  ·  4 Family
10 Old Waterbury Road
Middlebury, CT 06762
Advantage Realty Group, Inc. SmartMLS
294 Christian Road, Middlebury, CT
Active
$995,000
3 bd · 3.00 ba · 2,878 sqft
294 Christian Road
Middlebury, CT 06762
BHGRE Gaetano Marra Homes SmartMLS
182 Green Hill Road, Middlebury, CT
Active
$779,900
4 bd · 3.00 ba · 3,038 sqft
182 Green Hill Road
Middlebury, CT 06762
Showcase Realty, Inc. SmartMLS
9 Whitehall Court, Middlebury, CT
Active
$979,900
4 bd · 5.00 ba · 4,261 sqft
9 Whitehall Court
Middlebury, CT 06762
Lamacchia Realty SmartMLS
327 Steinmann Avenue, Middlebury, CT
Active
$300,000
2 bd · 1.00 ba · 676 sqft
327 Steinmann Avenue
Middlebury, CT 06762
Regency Real Estate, LLC SmartMLS
138 Steinmann Avenue, Middlebury, CT
Active
$350,000
3 bd · 2.00 ba · 1,466 sqft
138 Steinmann Avenue
Middlebury, CT 06762
West View Properties, LLC SmartMLS
See All 40 Homes in Middlebury

Buying a Home in Middlebury, CT

Current Market Snapshot

Entry Price
$140K
lowest listed
Avg. Price
$667K
list price
Top of Market
$2.9M
highest listed
Listings by Bedroom Count
1 bed
1
2 beds
3
3 beds
14
4 beds
15
5 beds
2
8 beds
1
Property Types Available
Single Family · 31 Land · 4 Condo / Co-Op · 4 Multi-Family For Sale · 1

The Middlebury real estate market currently has 40 active listings with an average list price of $667,100 and a price range from $139,999 to $2,850,000. Single Family homes make up the largest share of available inventory. Most listings are 4-bedroom homes. The average home size is 2,334 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 September 2026, there are 40 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 $667,100. Homes currently range from $139,999 to $2,850,000.
What size homes are most common in Middlebury, CT?
The most common listing in Middlebury is a 4-bedroom home (15 listings). Other common sizes include 3-bedroom (14) and 2-bedroom (3). The average home size is 2,334 sq ft.
What types of homes are available in Middlebury, CT?
Current listings in Middlebury include: Single Family (31), Land (4), Condo / Co-Op (4), Multi-Family For Sale (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.