View 10 Frederick Middletown, NY MLS# 939937
$539,900
4

Beds

2.1

Baths

2,144

Sq.Ft.

10 Frederick

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 5 Sayer Lane Middletown, NY MLS# 937803
$129,999
3

Beds

2.0

Baths

1,080

Sq.Ft.

5 Sayer Lane

Middletown, NY

Courtesy of HUDSON VALLEY HOME CONNECTION
View 57 Overhill Road Middletown, NY MLS# 935730
$350,000
5

Beds

2.1

Baths

3,581

Sq.Ft.

57 Overhill Road

Middletown, NY

Courtesy of EXP REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 16 Woodland Road Middletown, NY MLS# 939166
$268,000
3

Beds

1.0

Baths

1,250

Sq.Ft.

16 Woodland Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 78 Deer Ct Drive 78 Middletown, NY MLS# 939410
$279,000
2

Beds

2.0

Baths

1,291

Sq.Ft.

78 Deer Ct Drive 78

Middletown, NY

Courtesy of EXP REALTY
View 193 Schutt Road Middletown, NY MLS# 938818
  • Virtual Tour
1 of 20
$249,900
3

Beds

1.0

Baths

900

Sq.Ft.

193 Schutt Road

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 21 Cyprus Drive Middletown, NY MLS# 938656
  • Adult Community
1 of 43
$549,900
2

Beds

2.0

Baths

1,868

Sq.Ft.

21 Cyprus Drive

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 440 Mt Orange Road Middletown, NY MLS# 935459
$131,250
1

Beds

1.0

Baths

654

Sq.Ft.

440 Mt Orange Road

Middletown, NY

Courtesy of PRIME PARTNER REALTY
View 47 Wickham Avenue 45 Middletown, NY MLS# 937384
$499,900
1,478

Sq.Ft.

47 Wickham Avenue 45

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 100 Hillside Drive F5 Middletown, NY MLS# 937885
$278,000
2

Beds

2.0

Baths

1,012

Sq.Ft.

100 Hillside Drive F5

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 529 5th Ave Middletown, NY MLS# 938236
$153,000
3

Beds

2.0

Baths

1,152

Sq.Ft.

529 5th Ave

Middletown, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
View 17 N Aspen Road Middletown, NY MLS# 938270
$258,000
2

Beds

1.1

Baths

1,144

Sq.Ft.

17 N Aspen Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 10 Royce Ave Middletown, NY MLS# 937950
  • Virtual Tour
1 of 32
$330,000
3

Beds

1.1

Baths

1,470

Sq.Ft.

10 Royce Ave

Middletown, NY

Courtesy of EXP REALTY
View 71 Commonwealth Avenue Middletown, NY MLS# 936595
$360,000
3

Beds

1.0

Baths

1,344

Sq.Ft.

71 Commonwealth Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 270 Crystal Run Road Middletown, NY MLS# 933272
$399,900
3

Beds

2.0

Baths

1,450

Sq.Ft.

270 Crystal Run Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 36 Bert Crawford Road Middletown, NY MLS# 932531
$309,900
2

Beds

1.0

Baths

836

Sq.Ft.

36 Bert Crawford Road

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 27-29 W Conkling Avenue Middletown, NY MLS# 933968
$409,999
3

Beds

1.1

Baths

1,560

Sq.Ft.

27-29 W Conkling Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 4 Kless Court Middletown, NY MLS# 936597
$475,000
3

Beds

2.1

Baths

2,097

Sq.Ft.

4 Kless Court

Middletown, NY

Courtesy of YOURHOMESOLD GUARANTEED REALTY
View 356 Sands Road Middletown, NY MLS# 936090
$279,999
3

Beds

1.0

Baths

1,340

Sq.Ft.

356 Sands Road

Middletown, NY

Courtesy of EXIT REALTY CONNECTIONS
View 146 Deer Ct Drive Middletown, NY MLS# 936284
$310,000
2

Beds

2.1

Baths

1,473

Sq.Ft.

146 Deer Ct Drive

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY

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

243

Estimated median home price

$419,900
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 - 100K6
$100K - 200K18
$200K - 300K40
$300K - 400K51
$400K - 500K45
$500K - 600K23
$600K - 700K13
$700K - 800K11
$800K - 900K5
$900K - 1M4
$1M - Max27

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family146
Townhouse0
Condo26
Commercial34
Rental111
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home3
Farms0

(Data as of 1/14/2026)

Information deemed reliable but not guaranteed.

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.

Information Copyright 2021, OneKey® MLS. All Rights Reserved.