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Rentals Under $5,000/mo in Middletown, NY

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

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Show registered offenders

Selling Options

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

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What's worth fixing first
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Save search

3 beds Houses With a pool

48 listings

Rentals Under $5,000/mo for Rent in Middletown, NY

Rentals Under $5,000/mo for Rent in Middletown, NY

24 of 48 Listings

Rentals Under $5,000/mo for Rent in Middletown, NY

24 of 48 Listings

New14Active

$2,150/mo

2 bd · 2 ba · 900 sqft

256 Ruth Court, Middletown, NY

Allan M. Leeds · ON SITE Sales & Marketing, LLC

$2,300/mo

2 bd · 2 ba · 995 sqft

248 Concord Lane 248, Middletown, NY

Brenda D Watington · W Manor LLC

$1,700/mo

2 bd · 1 ba · 840 sqft

180 W Main Street 6, Middletown, NY

Theresa M Powers · Keller Williams Realty

$2,400/mo

2 bd · 2 ba · 1,142 sqft

206 Golf Links Road 331, Middletown, NY

John Chirico · Curasi Realty, Inc.

$2,500/mo

3 bd · 2 ba · 1,035 sqft

29 Genung Street, Middletown, NY

Dominick J Tufano · RE/MAX Benchmark Realty Group

$3,000/mo

3 bd · 2 ba · 2,070 sqft

208 White Bridge Road, Middletown, NY

Isaiah Lopez · KW Hudson Valley United

Price Reduced20Active

$1,900/mo

2 bd · 2 ba · 924 sqft

384 Concord Lane, Middletown, NY

Hazel D. Cello · KW Hudson Valley United

$2,200/mo

2 bd · 2 ba · 995 sqft

248 Concord Lane, Middletown, NY

Susan C Giordano · Hudson Premium Realty

$2,100/mo

3 bd · 1 ba · 1,127 sqft

1 Dewitt Street, Middletown, NY

Frances Levin · KW Hudson Valley United

$2,300/mo

2 bd · 2 ba · 1,133 sqft

49 Jimal Drive, Middletown, NY

Anita S. Cristiano · HomeSmart Homes & Estates

$3,000/mo

3 bd · 2 ba · 1,344 sqft

4 Westminster Drive, Middletown, NY

Elena James · Keller Williams Realty

Price Reduced14Active

$1,950/mo

2 bd · 1 ba · 994 sqft

47 Ruth Court, Middletown, NY

Jesse Lara · KW Hudson Valley United

$2,500/mo

2 bd · 2 ba · 995 sqft

248 Concord Lane, Middletown, NY

Annastasia N. Schondra · KW Hudson Valley United

$1,600/mo

0 bd · 1 ba · 600 sqft

255 North Street 3, Middletown, NY

Alan G. House JR · HomeSmart Homes & Estates

$2,900/mo

2 bd · 3 ba · 1,795 sqft

54 Fairways Drive, Middletown, NY

Richard Guerrero · KW Hudson Valley United

$3,600/mo

3 bd · 4 ba · 2,211 sqft

3 Cedar Hill Drive, Middletown, NY

Viticha DeLeon · KW Hudson Valley United

$2,700/mo

3 bd · 2 ba · 1,508 sqft

32 Deer Ct Drive, Middletown, NY

Jessica Welsh · KW Hudson Valley United

Price Reduced34Active

$2,800/mo

2 bd · 3 ba · 1,345 sqft

25 Fairways Drive 5, Middletown, NY

Hazel D. Cello · KW Hudson Valley United

Price Reduced13Active

$2,900/mo

3 bd · 2 ba · 1,504 sqft

20 Benton Avenue, Middletown, NY

Farzana Mian · Century 21 Full Service Realty

Price Reduced10Active

$2,545/mo

1 bd · 1 ba · 811 sqft

48 North Street 308, Middletown, NY

Tehillah Deslandes · Howard Hanna Rand Realty

Price Reduced10Active

$2,795/mo

2 bd · 1 ba · 861 sqft

48 North Street 301, Middletown, NY

Tehillah Deslandes · Howard Hanna Rand Realty

Price Reduced13Active

$2,795/mo

2 bd · 1 ba · 861 sqft

48 North Street 401, Middletown, NY

Tehillah Deslandes · Howard Hanna Rand Realty

Price Reduced12Active

$2,325/mo

1 bd · 1 ba · 758 sqft

48 North Street 406, Middletown, NY

Tehillah Deslandes · Howard Hanna Rand Realty

Price Reduced10Active

$2,495/mo

1 bd · 1 ba · 825 sqft

48 North Street 208, Middletown, NY

Tehillah Deslandes · Howard Hanna Rand Realty

1 2

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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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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