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Connecticut · Real Estate

Homes for Sale in
Middlebury, CT

There are currently 20 homes for sale in Middlebury, Connecticut with an average list price of $842,045.

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

20

active listings

Avg. Sale Price

$581K

$85K–$4.1M

Avg. Size Sold

2,211 sf

last 12 mo

vs. Ask Price

-1.0%

avg. paid vs. ask

Stats based on 109 closings in the last 12 months

Showing 12 of 20 listings in Middlebury

413 Watertown Road, Middlebury, CT
Active OH 6/27 · 11am–1pm
$485,000
4 bd · 3.00 ba · 2,251 sqft
413 Watertown Road
Middlebury, CT 06762
William Raveis Real Estate SmartMLS
70 Pine Hollow Drive, Middlebury, CT
Active OH 6/26 · 6pm–7:30pm
$669,000
3 bd · 3.00 ba · 2,734 sqft
70 Pine Hollow Drive
Middlebury, CT 06762
KW Legacy Partners SmartMLS
36 Independence Circle, Middlebury, CT
Active
$650,000
4 bd · 4.00 ba · 3,512 sqft  ·  Condominium
36 Independence Circle
Middlebury, CT 06762
Century 21 AllPoints Realty SmartMLS
25 Avalon Drive, Middlebury, CT
Active OH 6/27 · 12pm–2pm
$879,900
3 bd · 4.00 ba · 3,494 sqft
25 Avalon Drive
Middlebury, CT 06762
William Raveis Real Estate SmartMLS
700 Watertown Road, Middlebury, CT
Active OH 6/28 · 1pm–3pm
$615,000
5 bd · 3.00 ba · 2,528 sqft
700 Watertown Road
Middlebury, CT 06762
Regall Realty, LLC SmartMLS
61 Sandy Hill Road, Middlebury, CT
Active
$529,900
3 bd · 2.00 ba · 1,811 sqft
61 Sandy Hill Road
Middlebury, CT 06762
William Raveis Real Estate SmartMLS
1252 Straits Turnpike, Middlebury, CT
Active
$299,900
4 bd · 1.00 ba · 1,848 sqft
1252 Straits Turnpike
Middlebury, CT 06762
ALBERTI REALTY ASSOCIATES, LLC SmartMLS
168 North Farm Road, Middlebury, CT
Active
$729,900
4 bd · 4.00 ba · 3,302 sqft
168 North Farm Road
Middlebury, CT 06762
Showcase Realty, Inc. 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
90 Fenn Road, Middlebury, CT
Active
$679,900
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
See All 20 Homes in Middlebury

Buying a Home in Middlebury, CT

Current Market Snapshot

Entry Price
$250K
lowest listed
Avg. Price
$842K
list price
Top of Market
$2.9M
highest listed
Listings by Bedroom Count
3 beds
8
4 beds
7
5 beds
1
8 beds
1
Property Types Available
Single Family · 16 Land · 3 Condo / Co-Op · 1

The Middlebury real estate market currently has 20 active listings with an average list price of $842,045 and a price range from $249,900 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 June 2026, there are 20 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 $842,045. Homes currently range from $249,900 to $2,850,000.
What size homes are most common in Middlebury, CT?
The most common listing in Middlebury is a 3-bedroom home (8 listings). Other common sizes include 4-bedroom (7) and 5-bedroom (1). 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 (16), Land (3), 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.