Realty.com
Buy

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
Sell

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
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Registered offenders on the map

Save search

Registered offenders on the map

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Realty.com
Buy

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 searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

Registered offenders on the map

Sell

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
Home Loans
Find an Agent
Save search
3 bedsNew constructionWith a pool
5 Bedroom Homes in Middletown, NY
9 listings

5 Bedroom Homes in Middletown, NY

5 Bedroom Homes in Middletown, NY

Show Map
9 Listings
Map

5 Bedroom Homes in Middletown, NY

9 Listings

  1. 88 Grand Avenue — photo29Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

$425,000

5 bd · 2 ba · 1,736 sqft

88 Grand Avenue, Middletown, NY

Olivia Cappelli · Donna Ruffino Realty Corp

  • 580 Route 17M — photo40Active

    $350,000

    5 bd · 2 ba · 1,914 sqft

    580 Route 17M, Middletown, NY

    Matthew W. Gibbs · KW Hudson Valley United

  • 26 Winters Lane — photo21Active

    $829,999

    5 bd · — ba · 2,912 sqft

    26 Winters Lane, Middletown, NY

  • 20 3rd Street — photo40Active

    $670,000

    5 bd · 3 ba · 2,804 sqft

    20 3rd Street, Middletown, NY

    Feng Ching Chang SFR · Acer Realty Inc

  • 2096 Route 6 — photo21Active

    $899,999

    5 bd · 4 ba · 3,820 sqft

    2096 Route 6, Middletown, NY

    Silena R. Marchetti · S M Target Realty, LLC

  • 495 Guymard Turnpike — photo43Active

    $469,000

    5 bd · 3 ba · 2,448 sqft

    495 Guymard Turnpike, Middletown, NY

    Maureen E Cronin · Cronin & Company Real Estate

  • 35 Dogwood Drive — photoPrice Reduced13Active

    $530,000

    5 bd · 4 ba · 1,911 sqft

    35 Dogwood Drive, Middletown, NY

    Lenworth L. Brisco · Keller Williams Realty NYC Grp

  • 238 S Centerville Road — photoPrice Reduced30Active

    $834,000

    5 bd · 3 ba · 3,764 sqft

    238 S Centerville Road, Middletown, NY

    Linda VanDeWeert · BHG Real Estate Green Team

  • 20 Hidden Waters Drive — photo44Active

    $598,000

    5 bd · 4 ba · 2,352 sqft

    20 Hidden Waters Drive, Middletown, NY

    Christine O'Shaughnessy · Coldwell Banker Timberland Properties

  • Explore Middletown homes

    By price

    • Under $300K
    • Under $500K
    • Under $700K
    • Luxury

    By bedrooms

    • 2 beds
    • 3 beds
    • 4 beds
    • 5 beds

    By type

    • Single family
    • Townhomes
    • Condos
    • Manufactured homes
    • Multi-family homes
    • Co-ops

    By feature

    • New construction
    • With a pool
    Realty.com

    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

    Equal Housing OpportunityEqual Housing Lender

    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.

    © 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    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
    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, 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

    Middletown 12-month median sale price trend

    Selling at 100.4% of asking price

    Sales here are closing essentially at asking. MLS · 48 sales · as of Aug 31, 2026

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

    Median sale price
    $439,900$327,500–$595,000 typical range
    Price per sq. ft.
    $273
    Sales
    43
    Paid in cash
    32.6%

    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
    10.4%

    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.