Homes Under $500K in Middletown, NY

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24 Listings

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24 Listings

1Active

24 listings

Homes Under $500K in Middletown, NY

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24 Listings

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Homes Under $500K in Middletown, NY

24 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

1Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

$199,000

1 bd · 1 ba · 830 sqft

122 Sycamore Drive, Middletown, NY

Christina Wilger · RE/MAX Benchmark Realty Group

18Active

$394,900

2 bd · 3 ba · 1,337 sqft

19 Putters Way 9, Middletown, NY

Christina Wilger · RE/MAX Benchmark Realty Group

35Active

$299,000

2 bd · 2 ba · 1,291 sqft

143 Deer Ct Drive, Middletown, NY

Martha Randazzo · Howard Hanna Rand Realty

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

22Active

$488,000

3 bd · 3 ba · 1,715 sqft

5 Blanchard Street, Middletown, NY

JoAnn Maxwell · Howard Hanna Rand Realty

18Active

$284,900

2 bd · 2 ba · 1,342 sqft

132 Sycamore Drive, Middletown, NY

Stacy Brescia-Spreer · Curasi Realty, Inc.

Open house Sun, Oct 4 · 12:00 PM35Active

$259,000

2 bd · 2 ba · 1,133 sqft

91 Jimal Drive, Middletown, NY

Darlene Brennan · Howard Hanna Rand Realty

22Active

$285,000

2 bd · 2 ba · 1,133 sqft

65 Jimal Drive, Middletown, NY

Rebecca Kane · KW Hudson Valley United

25Active

$220,000

1 bd · 2 ba · 785 sqft

14 Brick Pond Road, Middletown, NY

Guy Cusumano · Howard Hanna Rand Realty

21Active

$484,900

3 bd · 3 ba · 1,723 sqft

22 Atwood Drive, Middletown, NY

Kelly L Roebuck · Curasi Realty, Inc.

Price Reduced42Active

$199,000

1 bd · 1 ba · 879 sqft

11 Brittany Drive, Middletown, NY

Amanda Ferrantello · Hudson Valley Griffith

35Active

$329,900

2 bd · 2 ba · 1,340 sqft

50 Sycamore Drive 50, Middletown, NY

Maliki Cottrell · Cottrell & Associates RE Corp.

Price Reduced26Active

$295,000

2 bd · 2 ba · 1,291 sqft

18 Deer Court Drive, Middletown, NY

David B Wilson · Hudson Premium Realty

Price Reduced14Active

$314,000

2 bd · 3 ba · 1,348 sqft

35 Lexington Way, Middletown, NY

Zhiheng Tang · KW Hudson Valley United

25Active

$289,000

2 bd · 2 ba · 1,110 sqft

63 Sycamore Drive 63, Middletown, NY

Kyle Pierce · Patricia Schiller Real Est Co.

Price Reduced22Active

$319,990

3 bd · 3 ba · 1,460 sqft

43 Brick Pond Road, Middletown, NY

Hai Li · KW Hudson Valley United

37Active

$289,900

2 bd · 2 ba · 1,049 sqft

141 Ruth Court, Middletown, NY

Dawn E. Gregg · Curasi Realty, Inc.

Price Reduced20Active

$139,000

1 bd · 1 ba · 735 sqft

394 Concord Lane, Middletown, NY

Carol Scully · Keller Williams Realty

Price Reduced35Active

$469,000

3 bd · 3 ba · 2,084 sqft

1 High Ridge Lane, Middletown, NY

Jason J. Madison · eXp Realty

Price Reduced41Active

$349,000

3 bd · 3 ba · 1,200 sqft

202 Concord Lane, Middletown, NY

Soleil Jackman · Howard Hanna Rand Realty

28Active

$399,000

2 bd · 3 ba · 1,337 sqft

19 Putters Way 6, Middletown, NY

Xiaohui Cui · KW Hudson Valley United

Price Reduced50Active

$500,000

3 bd · 3 ba · 2,567 sqft

29 Avoncroft Lane, Middletown, NY

Gail J Rachlin · KW Hudson Valley United

21Active

$299,900

3 bd · 2 ba · 1,884 sqft

2 S Aspen Road, Middletown, NY

Derek J. Greene · Greene Realty Group

Price Reduced43Active

$399,900

3 bd · 3 ba · 1,919 sqft

83 Deer Ct Drive, Middletown, NY

Dulce M Ferrera · KW Hudson Valley United

Price Reduced31Active

$278,000

2 bd · 2 ba · 1,146 sqft

66 Deer Ct Drive, Middletown, NY

Jie Liu · KW Hudson Valley United

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

Middletown housing market

August 2026 · This period is still settling

Selling at 100.7% of asking price

Buyers here are paying above asking. MLS · 49 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 28, 2026

Median sale price: $432,450$321,250–$547,500 typical range
Price per sq. ft.: $269
Sales: 50
Paid in cash: 34.0%

Homes on the market · MLS, as of Aug 24, 2026–Aug 31, 2026

Median list price: $450,000
Homes for sale: 146
Median days on market: 22 days

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

Year-over-year: 9.7%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 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

Explore Middletown homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

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

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

August 2026 · This period is still settling

Selling at 100.7% of asking price

Buyers here are paying above asking. MLS · 49 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 28, 2026

Median sale price: $432,450$321,250–$547,500 typical range
Price per sq. ft.: $269
Sales: 50
Paid in cash: 34.0%

Homes on the market · MLS, as of Aug 24, 2026–Aug 31, 2026

Median list price: $450,000
Homes for sale: 146
Median days on market: 22 days

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

Year-over-year: 9.7%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

Median home size: 1,694 sq. ft.

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Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Middletown housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 24, 2026–Aug 31, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

Middletown, NY community profile

Explore Middletown homes

Your local brokerage

Listing data & MLS disclosures

Middletown, NY community profile

Middletown housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 24, 2026–Aug 31, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026