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Connecticut · Real Estate

Homes for Sale in
Middlebury, CT

There are currently 27 homes for sale in Middlebury, Connecticut with an average list price of $725,948.

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

27

active listings

Avg. Sale Price

$581K

$85K–$4.1M

Avg. Size Sold

2,249 sf

last 12 mo

vs. Ask Price

-0.7%

avg. paid vs. ask

Stats based on 113 closings in the last 12 months

Showing 12 of 27 listings in Middlebury

420 Charcoal Avenue, Middlebury, CT
Coming Soon Open House 4/25 · 11am–1pm
$485,000
3 bd · 2.00 ba · 1,575 sqft
420 Charcoal Avenue
Middlebury, CT 06762
Stone Crest Realty LLC SmartMLS
122 Crest Road, Middlebury, CT
Active
$825,000
3 bd · 3.00 ba · 3,253 sqft
122 Crest Road
Middlebury, CT 06762
Showcase Realty, Inc. SmartMLS
851 South Street, Middlebury, CT
Active
$950,000
5 bd · 3.00 ba · 3,301 sqft
851 South Street
Middlebury, CT 06762
Showcase Realty, Inc. SmartMLS
66 Artillery Road, Middlebury, CT
Active
$585,000
4 bd · 4.00 ba · 2,691 sqft
66 Artillery Road
Middlebury, CT 06762
Klemm Real Estate Inc SmartMLS
2 Arrowwood Court #2, Middlebury, CT
Active Open House 4/26 · 12pm–2pm
$599,900
3 bd · 3.00 ba · 2,256 sqft  ·  Condominium
2 Arrowwood Court #2
Middlebury, CT 06762
BHGRE Gaetano Marra Homes SmartMLS
64 Watertown Road, Middlebury, CT
Active
$759,900
3 bd · 4.00 ba · 4,094 sqft
64 Watertown Road
Middlebury, CT 06762
William Raveis Real Estate SmartMLS
193 Ridgewood Drive #193, Middlebury, CT
Active
$649,900
3 bd · 3.00 ba · 2,658 sqft  ·  Condominium
193 Ridgewood Drive #193
Middlebury, CT 06762
Drakeley Real Estate, Inc. SmartMLS
36 Highridge Road #36, Middlebury, CT
Active
$585,000
3 bd · 3.00 ba · 1,997 sqft  ·  Condominium
36 Highridge Road #36
Middlebury, CT 06762
RE/MAX RISE SmartMLS
1140 Southford Road, Middlebury, CT
Active
$399,000
Commercial Land
1140 Southford Road
Middlebury, CT 06762
Ghent Realty Advisors SmartMLS
223 Carriage Drive, Middlebury, CT
Active
$674,900
4 bd · 4.00 ba · 2,484 sqft
223 Carriage Drive
Middlebury, CT 06762
BHGRE Gaetano Marra Homes SmartMLS
20 Hunting Ridge Road, Middlebury, CT
Active
$735,900
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
See All 27 Homes in Middlebury

Buying a Home in Middlebury, CT

Current Market Snapshot

Entry Price
$225K
lowest listed
Avg. Price
$726K
list price
Top of Market
$2.9M
highest listed
Listings by Bedroom Count
2 beds
1
3 beds
13
4 beds
7
5 beds
2
8 beds
1
Property Types Available
Single Family · 18 Condo / Co-Op · 5 Land · 3 Multi-Family For Sale · 1

The Middlebury real estate market currently has 27 active listings with an average list price of $725,948 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 2,624 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 April 2026, there are 27 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 $725,948. 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 (13 listings). Other common sizes include 4-bedroom (7) and 5-bedroom (2). The average home size is 2,624 sq ft.
What types of homes are available in Middlebury, CT?
Current listings in Middlebury include: Single Family (18), Condo / Co-Op (5), Land (3), 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.