Homes Under $500K in Middletown, NY

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24 of 149 Listings

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Thomas O'Leary

Realty.com

Lic. #10311208632

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NewOpen house Sun, Oct 25 · 1:00 PM32Active
$339,000
2 bd · 3 ba · 1,473 sqft
197 Deer Ct Drive, Middletown, NY
David L. White · Owner Entry.com
New21Active
$399,000
4 bd · 2 ba · 1,932 sqft
61 Maureen Drive, Middletown, NY
Yara Roussos · Homes By Yara Realty Group LLC
New43Active
$448,000
3 bd · 4 ba · 2,360 sqft
405 County Route 22, Middletown, NY
Stephanie Dolan · HomeSmart Homes & Estates

Listing data & MLS disclosures

NY State MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the New York State Alliance MLS. 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. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither the listing broker(s) nor Realty.com shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless. Copyright © 2026 New York State Alliance and participating MLS's - CNYIS, UNYREIS and WNYREIS. All Rights Reserved.
OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. 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. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

About Homes Under $500K in Middletown, NY

Homes Under $500K in Middletown, NY: 149 active listings as of October 18, 2026, 22:42 UTC.

Property types among these 149 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property type	Listings	Share
Single Family Residence	112	75.2%
Condominium	24	16.1%
Mixed Use	6	4.0%

Middletown housing market

September 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 42 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 24, 2026

Median sale price: $425,000$315,000–$489,000 typical range
Price per sq. ft.: $221
Sales: 21
Paid in cash: 38.1%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $469,000
Homes for sale: 161
Median days on market: 26 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 4.9%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 9, 2026

Median home size: 1,694 sq. ft.

Middletown, NY community profile

Population: 31,152
Median income: $70,005
Housing units: 12,399
People per sq. mi.: 318.9
Area: 97.7 sq. mi.

Source: HJN community data

Homes Under $500K in Middletown, NY

Your local brokerage

Listing data & MLS disclosures

About Homes Under $500K in Middletown, NY

Middletown housing market

Homes that sold · County records, as of Sep 24, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 9, 2026

Middletown, NY community profile

Explore Middletown homes

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

Middletown, NY community profile

Middletown housing market

Homes that sold · County records, as of Sep 24, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 9, 2026