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Middletown, NY Homes for Sale — Page 5 | Realty.com

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Homes for Sale in Middletown, NY

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19 of 208 Listings

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19 of 208 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

49Active
$765,000
4 bd · 3 ba · 3,064 sqft
118 Ridge Drive, Middletown, NY
Patricia M Sassi · RE/MAX Benchmark Realty Group
7Active
$849,999
4 bd · 3 ba · 2,862 sqft
241 Midland Lake Road, Middletown, NY
Hilary R. Goldman · Howard Hanna Rand Realty
Price Reduced43Active
$295,000
3 bd · 1 ba · 992 sqft
148 Church Street, Middletown, NY
Sean O'Shaughnessy · Coldwell Banker Timberland Properties

Price Reduced29Active
$389,000
3 bd · 2 ba · 1,316 sqft
30 Chestnut Avenue, Middletown, NY
Lauren Iacono · Corcoran Baer & McIntosh
Price Reduced26Active
$210,000
2 bd · 2 ba · 600 sqft
43396 State Highway 28, Middletown, NY
Sean O'Shaughnessy · Coldwell Banker Timberland Properties
50Active
$549,999
4 bd · 4 ba · 2,298 sqft
19 Davidge Road, Middletown, NY
Kevin Grier · KW Hudson Valley United
49Active
$499,999
3 bd · 3 ba · 1,660 sqft
81 Silver Lake Sctn Road, Middletown, NY
Antoinette M Gundersen · HomeSmart Homes & Estates
Price Reduced32Active
$714,000
4 bd · 3 ba · 2,733 sqft
210 Howells Turnpike, Middletown, NY
Cecilia Lewis · Century 21 Elite Realty
20Active
$420,000
3 bd · 3 ba · 2,097 sqft
4 Kless Court, Middletown, NY
Bryant Moran · YourHomeSold Guaranteed Realty
Price Reduced49Active
$455,000
3 bd · 2 ba · 1,545 sqft
168 Shawangunk Road, Middletown, NY
Jason Kerwar · William Raveis Real Estate
30Active
$300,000
6 bd · 2 ba · 1,992 sqft
135 Eisele Road, Middletown, NY
Billie Kunzang · Kunzang Realty Group LLC
19Active
$333,000
3 bd · 1 ba · 1,152 sqft
23 Harrison Street, Middletown, NY
Pedro Garcia · Curasi Realty, Inc.
Price Reduced38Active
$399,900
4 bd · 1 ba · 1,204 sqft
39 California Avenue, Middletown, NY
Guoqing Ouyang · Dalton Wade Inc.
34Active
$539,900
4 bd · 3 ba · 2,176 sqft
31 Denman Road, Middletown, NY
Kenyatta A Jones-Arietta · R2M Realty Inc
37Active
$389,000
2 bd · 2 ba · 1,588 sqft
407 Winter Hollow Road, Middletown, NY
Esther de Jong · Coldwell Banker Timberland Properties
Price Reduced49Active
$489,999
3 bd · 3 ba · 2,500 sqft
58 Cobblestone Lane, Middletown, NY
Doreen Crowther · Howard Hanna Rand Realty
40Active
$745,000
3 bd · 2 ba · 1,579 sqft
1794 Winter Hollow Road, Middletown, NY
Hillary Kolos · COMPASS Greater NY LLC
Price Reduced36Active
$365,000
3 bd · 2 ba · 1,200 sqft
31 Lakota Drive, Middletown, NY
Pamela Jean Orr · Keller Williams Upstate NY Properties
33Active
$599,000
3 bd · 3 ba · 2,086 sqft
189 School House Road, Middletown, NY
Joseph Paoli · Howard Hanna Rand Realty

1…4 5 6…9

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

August 2026 · This period is still settling

Selling at 101.4% 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 25, 2026

Median sale price: $448,500$367,500–$595,000 typical range
Price per sq. ft.: $263
Sales: 35
Paid in cash: 28.6%

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: 23 days

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

Year-over-year: 15.6%

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

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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

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.

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

By feature

New construction
With a pool

Nearby areas

ZIP codes

10950 (194)
10940 (143)
12550 (108)
12701 (80)
12553 (75)
10918 (70)
10990 (67)
12790 (62)

Cities

Monroe (182)
Newburgh (106)
Monticello (76)
New Windsor (75)
Chester (70)
Warwick (68)
Spring Valley (60)
Wurtsboro (59)

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

August 2026 · This period is still settling

Selling at 101.4% 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 25, 2026

Median sale price: $448,500$367,500–$595,000 typical range
Price per sq. ft.: $263
Sales: 35
Paid in cash: 28.6%

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: 23 days

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

Year-over-year: 15.6%

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.

Nearby areas

ZIP codes

10950 (194)
10940 (143)
12550 (108)
12701 (80)
12553 (75)
10918 (70)
10990 (67)
12790 (62)

Cities

Monroe (182)
Newburgh (106)
Monticello (76)
New Windsor (75)
Chester (70)
Warwick (68)
Spring Valley (60)
Wurtsboro (59)