Homes Under $500K in Middletown, NY

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3 beds New construction With a pool

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21 of 128 Listings

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Homes Under $500K in Middletown, NY

21 of 128 Listings

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Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

36Active
$475,000
3 bd · 3 ba · 2,257 sqft
4 Woodrose Court, Middletown, NY
Alyssa Scancarello · Howard Hanna Rand Realty
New42Active
$215,000
1 bd · 1 ba · 879 sqft
11 Brittany Drive, Middletown, NY
Amanda Ferrantello · Hudson Valley Griffith
9Active
$299,000
2 bd · 1 ba · 560 sqft
220 Upper Kennedy, Middletown, NY
Debra Smith · Coldwell Banker Timberland Properties

Listing data & MLS disclosures

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
New York State Alliance of MLSs: 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.

Middletown housing market

July 2026 · This period is still settling

Selling at 101.7% of asking price

Buyers here are paying above asking. MLS · 43 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 31, 2026

Median sale price: $400,000$250,750–$513,500 typical range
Price per sq. ft.: $229
Sales: 39
Paid in cash: 59.0%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $444,500
Homes for sale: 132
Median days on market: 27 days

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

Year-over-year: -5.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 1,692 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

Explore Middletown homes

Listing data & MLS disclosures

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
New York State Alliance of MLSs: 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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

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

Middletown housing market

July 2026 · This period is still settling

Selling at 101.7% of asking price

Buyers here are paying above asking. MLS · 43 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 31, 2026

Median sale price: $400,000$250,750–$513,500 typical range
Price per sq. ft.: $229
Sales: 39
Paid in cash: 59.0%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $444,500
Homes for sale: 132
Median days on market: 27 days

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

Year-over-year: -5.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 1,692 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Listing data & MLS disclosures

Middletown housing market

Homes that sold · County records, as of Jul 31, 2026

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 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 Jul 31, 2026

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026