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Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Commercial

Registered offenders on the map

Show registered offenders (Florida and Texas)

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

New construction

3 listings

Luxury Homes in Middlebury, IN

Luxury Homes in Middlebury, IN

3 Listings

Luxury Homes in Middlebury, IN

3 Listings

50Active
$1,200,000

6 bd · — ba · 6,412 sqft

205 Greenfield Drive, Middlebury, IN

Julie Thatcher · Coldwell Banker Real Estate Group

$1,390,000

5 bd · — ba · 6,370 sqft

54725 County Road 33, Middlebury, IN

Chantel Boone · RE/MAX Results

$4,999,900

6 bd · — ba · 12,367 sqft

54420 County Road 33 Road, Middlebury, IN

Stephen Smith · Irish Realty

Explore Middlebury homes

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Steve Merritt

Realty.com

Lic. #RB21000412

Listing data & MLS disclosures

Indiana Regional MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the Indiana Regional MLS LLC®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by brokerage firms other than Realty.com, are indicated by detailed information about them such as the name of the listing firms. Information deemed reliable but not guaranteed. Copyright © 2026 Indiana Regional MLS LLC®. All Rights Reserved.

Middlebury, IN community profile

Population: 3,443
Median income: $89,000
Housing units: 1,252
People per sq. mi.: 54.9
Area: 62.7 sq. mi.

Source: HJN community data

Middlebury housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 11 sales · as of Aug 25, 2026

Homes on the market · MLS, as of Aug 25, 2026–Aug 31, 2026

Median list price: $422,500
Homes for sale: 28
Median days on market: 8 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 11.8%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 2,249 sq. ft.

Luxury Homes in Middlebury, IN