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Connecticut · Real Estate

Homes for Sale in
Middlebury, CT

As of November 10, 2026, per SmartMLS, there are 31 homes for sale in Middlebury, Connecticut with an average list price of $702,410.

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

31

active listings

Median Sale Price

$572K

$70K–$4.1M

Avg. Size Sold

2,295 sf

last 12 mo

vs. Ask Price

-0.7%

avg. paid vs. ask

Stats based on 122 closings in the last 12 months · SmartMLS, as of Nov 10, 2026

Showing 12 of 31 listings in Middlebury

203 North Farm Road, Middlebury, CT
Active
$870,000
4 bd · 6 ba · 4,321 sqft
203 North Farm Road
Middlebury, CT 06762
Coldwell Banker Realty SmartMLS
Lots 12,13, 14 Mirey Dam Road, Middlebury, CT
Active
$569,900
Residential Land
Lots 12,13, 14 Mirey Dam Road
Middlebury, CT 06762
BHGRE Gaetano Marra Homes SmartMLS
203 Sugar Maple Way #203, Middlebury, CT
Active
$589,900
2 bd · 3 ba · 2,442 sqft  ·  Condominium
203 Sugar Maple Way #203
Middlebury, CT 06762
Berkshire Hathaway NE Prop. SmartMLS
42 White Avenue, Middlebury, CT
Active
$439,900
3 bd · 3 ba · 2,112 sqft
42 White Avenue
Middlebury, CT 06762
West View Properties, LLC SmartMLS
106 Mirey Dam Road, Middlebury, CT
Active
$725,000
4 bd · 3 ba · 2,534 sqft
106 Mirey Dam Road
Middlebury, CT 06762
BHGRE Gaetano Marra Homes SmartMLS
783 Whittemore Road, Middlebury, CT
Active
$725,000
5 bd · 3 ba · 3,728 sqft
783 Whittemore Road
Middlebury, CT 06762
Keller Williams Realty SmartMLS
314 Porter Avenue, Middlebury, CT
Active
$485,000
3 bd · 2 ba · 1,740 sqft
314 Porter Avenue
Middlebury, CT 06762
Derek Greene SmartMLS
6 Deer Run Road, Middlebury, CT
Active
$849,900
3 bd · 3 ba · 2,190 sqft
6 Deer Run Road
Middlebury, CT 06762
Real Estate Two SmartMLS
802 Charcoal Avenue, Middlebury, CT
Active
$499,900
4 bd · 3 ba · 1,911 sqft
802 Charcoal Avenue
Middlebury, CT 06762
BHGRE Gaetano Marra Homes SmartMLS
25 Juniper Road, Middlebury, CT
Active
$825,000
3 bd · 4 ba · 3,024 sqft
25 Juniper 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 ba · 2,345 sqft  ·  4 Family
10 Old Waterbury Road
Middlebury, CT 06762
Advantage Realty Group, Inc. SmartMLS
Read our Living in Middlebury, CT guide
See All 31 Homes in Middlebury

Buying a Home in Middlebury, CT

Current Market Snapshot

Entry Price
$140K
lowest listed
Avg. Price
$702K
list price
Top of Market
$2.9M
highest listed
Listings by Bedroom Count
2 beds
2
3 beds
10
4 beds
10
5 beds
3
8 beds
1
Property Types Available
Single Family · 24 Land · 5 Condo / Co-Op · 1 Multi-Family For Sale · 1

As of November 10, 2026, the Middlebury real estate market has 31 active listings with an average list price of $702,410 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 3-bedroom homes. The average home size is 2,430 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 November 10, 2026, per SmartMLS, there are 31 active listings in Middlebury, CT. All listings are updated every 15 minutes directly from SmartMLS.
What is the average home price in Middlebury, CT?
As of November 10, 2026, per SmartMLS, the average list price in Middlebury is $702,410. 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 3-bedroom home (10 listings). Other common sizes include 4-bedroom (10) and 5-bedroom (3). The average home size is 2,430 sq ft.
What types of homes are available in Middlebury, CT?
Current listings in Middlebury include: Single Family (24), Land (5), Condo / Co-Op (1), 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 New Haven County and the greater Connecticut market, including Middlebury. Contact us for a free consultation.