View 86 Maples Road Middletown, NY MLS# 1001524
$515,000
4

Beds

3.0

Baths

2,484

Sq.Ft.

86 Maples Road

Middletown, NY

Courtesy of RE/MAX TOWN & COUNTRY
View 75 Brola Road Middletown, NY MLS# 990133
  • Recently Listed
1 of 17
$499,999
3

Beds

2.1

Baths

2,074

Sq.Ft.

75 Brola Road

Middletown, NY

Courtesy of EXP REALTY
View 153 Ridge Drive Middletown, NY MLS# 996792
  • Recently Listed
1 of 47
OPEN HOUSE: Sunday 5/24 12:00 PM - 2:00 PM
$575,000
3

Beds

3.0

Baths

2,133

Sq.Ft.

153 Ridge Drive

Middletown, NY

Courtesy of EXP REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 180 Mt Orange Road Middletown, NY MLS# 998755
  • Recently Listed
1 of 46
OPEN HOUSE: Saturday 5/23 12:00 PM - 2:00 PM
$599,900
5

Beds

2.0

Baths

2,432

Sq.Ft.

180 Mt Orange Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 215 Linden Avenue Middletown, NY MLS# 1001604
$599,900
6

Beds

2.0

Baths

3,190

Sq.Ft.

215 Linden Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 28 Cyprus Drive Middletown, NY MLS# 998266
  • Recently Listed
1 of 36
$499,900
2

Beds

2.0

Baths

1,473

Sq.Ft.

28 Cyprus Drive

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 20 Park Circle Drive Middletown, NY MLS# 998648
  • Recently Listed
1 of 50
$539,000
4

Beds

2.1

Baths

2,644

Sq.Ft.

20 Park Circle Drive

Middletown, NY

Courtesy of EREALTY ADVISORS, INC
View 153 Ridgewood Avenue Middletown, NY MLS# 992982
  • Recently Listed
1 of 35
$475,000
3

Beds

2.0

Baths

1,577

Sq.Ft.

153 Ridgewood Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 217-219 Highland Avenue Middletown, NY MLS# 977631
  • Recently Listed
1 of 41
$479,000
3

Beds

2.1

Baths

2,228

Sq.Ft.

217-219 Highland Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 55 Eisenhower Drive Middletown, NY MLS# 999918
  • Recently Listed
1 of 12
$539,900
4

Beds

3.0

Baths

2,560

Sq.Ft.

55 Eisenhower Drive

Middletown, NY

Courtesy of EREALTY ADVISORS, INC
View 126 Rolling Meadows Road Middletown, NY MLS# 998294
  • Recently Listed with Virtual Tour
1 of 48
$447,000
4

Beds

2.1

Baths

2,155

Sq.Ft.

126 Rolling Meadows Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 8 Roberts Street Middletown, NY MLS# 998312
  • Recently Listed
1 of 9
OPEN HOUSE: Sunday 5/24 2:00 PM - 4:00 PM
$460,000
5

Beds

2.0

Baths

2,132

Sq.Ft.

8 Roberts Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 47 Wickham Avenue 45 Middletown, NY MLS# 997491
  • Recently Listed
1 of 18
$450,000
3

Beds

1.0

Baths

1,478

Sq.Ft.

47 Wickham Avenue 45

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 13 Benton Avenue Middletown, NY MLS# 998257
  • Recently Listed
1 of 21
$450,000
1,450

Sq.Ft.

13 Benton Avenue

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 12 Weather Vane Way Middletown, NY MLS# 992510
    1 of 40
    OPEN HOUSE: Saturday 5/23 12:00 PM - 2:00 PM
    $474,999
    3

    Beds

    2.1

    Baths

    2,055

    Sq.Ft.

    12 Weather Vane Way

    Middletown, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 122 Rolling Meadows Road Middletown, NY MLS# 991496
    $465,000
    3

    Beds

    2.0

    Baths

    2,055

    Sq.Ft.

    122 Rolling Meadows Road

    Middletown, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 15 High Ridge Lane Middletown, NY MLS# 996214
    • Recently Listed
    1 of 26
    $479,900
    2

    Beds

    2.1

    Baths

    1,762

    Sq.Ft.

    15 High Ridge Lane

    Middletown, NY

    Courtesy of RE/MAX BENCHMARK REALTY GROUP
    View 13 Hermanette Avenue Middletown, NY MLS# 995759
    • Recently Listed
    1 of 29
    $460,000
    3

    Beds

    2.1

    Baths

    1,852

    Sq.Ft.

    13 Hermanette Avenue

    Middletown, NY

    Courtesy of Weichert Realtors - Monroe
    View 29 Murray Road Middletown, NY MLS# 994440
    • Recently Listed
    1 of 24
    $579,000
    5

    Beds

    3.0

    Baths

    2,202

    Sq.Ft.

    29 Murray Road

    Middletown, NY

    Courtesy of KELLER WILLIAMS HUDSON VALLEY
    View 12 Oak Ridge Road Middletown, NY MLS# 994308
    • Recently Listed with Virtual Tour
    1 of 48
    $574,990
    3

    Beds

    2.0

    Baths

    2,596

    Sq.Ft.

    12 Oak Ridge Road

    Middletown, NY

    Courtesy of JACKIE HENRY REALTY LLC

    About Middletown

    Surrounded by such communities as Goshen and Wallkill, Middletown offers the expanded educational opportunities of Orange County Community College to the regional amenities.  Tranquil and yet convenient, Middletown is home to retail and commercial activity.  For expansive shopping, regional malls are just minutes from home.  Although the city is home to a number of businesses and light industry, it is primarily a residential community with a pleasing variety of single-family homes.  Both newer construction and fine older homes combine with multi-family options.  Commuters can travel to New York City via Metro-North rail or catch buses into the Port Authority.  An abundance of county and local parks ensure outdoor enjoyment.  Attractions include picnic areas and miles of hiking and biking trails as well as tennis courts and golf courses.

    Listings in Middletown, NY

    272

    Estimated median home price

    $450,000
    Middletown NY Homes for Sale & Properties

    Weichert Realtors is one of the nation's leading providers of Middletown, New York real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Middletown, NY.

    Homes for Sale by Price in Middletown, NY

    PriceCount
    $0 - 100K11
    $100K - 200K20
    $200K - 300K28
    $300K - 400K56
    $400K - 500K67
    $500K - 600K31
    $600K - 700K18
    $700K - 800K6
    $800K - 900K7
    $900K - 1M7
    $1M - Max21

    Homes for Sale by Type in Middletown, NY

    Property TypeCount
    Single Family164
    Townhouse0
    Condo23
    Commercial36
    Rental113
    Lots and Land27
    Condo/Town/CoOp0
    CoOp0
    Multi Family15
    Mobile Home7
    Farms0

    (Data as of 5/20/2026)

    Information deemed reliable but not guaranteed.

    The data relating to real estate for sale on this web site comes in part from The Internet Data Exchange Program of ©2026 Global Multiple Listing Service, Inc. The data relating to real estate on this website comes in part from the Internet Data Exchange program of the GMLS. All information is deemed reliable but not guaranteed and should be independently verified. All properties subject to prior sale, change, or withdrawal. Neither listing broker(s), GMLS shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless from any damages arising from reliance upon these data. 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 they may be interested in purchasing.

    Data is updated as of 5/20/2026.

    All information provided is deemed reliable but is not guaranteed and should be independently verified.

    Copyright 2026 by the Multiple Listing service of Ulster County, Inc. All Rights Reserved.

    The data relating to real estate on this web site comes in part from the IDX of the Multiple Listing service of Ulster County, Inc. Real estate listings held by brokerage firms other that Weichert Realtors are marked with IDX logo and the detailed information about them includes the name of the listing broker.

    The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

    The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use.

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