View 57 Union Avenue New Windsor, NY MLS# H6204046
$585,000
4

Beds

3.0

Baths

2,500

Sq.Ft.

57 Union Avenue

New Windsor, NY

Courtesy of REAL ESTATE EXCHANGE LTD
View 17 Old Hemlock Drive New Windsor, NY MLS# 1041638
$572,000
3

Beds

2.0

Baths

1,807

Sq.Ft.

17 Old Hemlock Drive

New Windsor, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 263 Riley Road New Windsor, NY MLS# 000031
1 of 28
OPEN HOUSE: Sunday 11/15 11:00 AM - 1:00 PM
$569,900
4

Beds

2.0

Baths

2,432

Sq.Ft.

263 Riley Road

New Windsor, NY

Courtesy of CURASI REALTY, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 39 Clintonwood Drive New Windsor, NY MLS# 1055234
$569,900
5

Beds

3.0

Baths

2,291

Sq.Ft.

39 Clintonwood Drive

New Windsor, NY

Courtesy of HOMESMART HOMES & ESTATES
View 15 Guernsey Drive New Windsor, NY MLS# 1053022
$559,888
4

Beds

2.1

Baths

2,052

Sq.Ft.

15 Guernsey Drive

New Windsor, NY

Courtesy of KELLER WILLIAMS VILLAGE SQ RLT
View 2 Lilac Hill Road New Windsor, NY MLS# 1044757
  • Virtual Tour
1 of 44
$550,000
3

Beds

2.1

Baths

1,947

Sq.Ft.

2 Lilac Hill Road

New Windsor, NY

Courtesy of Weichert Realtors - Monroe
View 150 Mount Airy Road New Windsor, NY MLS# 1010275
$549,900
3

Beds

4.0

Baths

2,790

Sq.Ft.

150 Mount Airy Road

New Windsor, NY

Courtesy of HOWARD HANNA RAND REALTY
View 5 Jennifer Court New Windsor, NY MLS# 1063900
  • Recently Listed
1 of 20
$549,000
4

Beds

2.1

Baths

2,028

Sq.Ft.

5 Jennifer Court

New Windsor, NY

Courtesy of EXP REALTY
View 83 Harth Drive New Windsor, NY MLS# 1050802
  • Virtual Tour
1 of 20
$545,000
4

Beds

2.1

Baths

1,616

Sq.Ft.

83 Harth Drive

New Windsor, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 409 Carlton Circle New Windsor, NY MLS# 20266523
  • Recently Listed
1 of 27
$539,000
4

Beds

2.1

Baths

2,500

Sq.Ft.

409 Carlton Circle

New Windsor, NY

UlsterCountyNY
Courtesy of FOUR SEASONS SOTHEBY'S INT'L R
View 409 Carlton Circle New Windsor, NY MLS# 1069979
  • Recently Listed
1 of 27
$539,000
4

Beds

2.1

Baths

2,500

Sq.Ft.

409 Carlton Circle

New Windsor, NY

Courtesy of FOUR SEASONS SOTHEBYS INTL
View 105 Shaker Court N New Windsor, NY MLS# 934043
  • Virtual Tour
1 of 38
$537,999
3

Beds

2.1

Baths

1,764

Sq.Ft.

105 Shaker Court N

New Windsor, NY

Courtesy of HOWARD HANNA RAND REALTY
View 51 Keats Drive New Windsor, NY MLS# 1039107
$529,500
3

Beds

2.1

Baths

2,207

Sq.Ft.

51 Keats Drive

New Windsor, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 584 Shore Drive New Windsor, NY MLS# 1009591
$527,500
4

Beds

2.1

Baths

2,518

Sq.Ft.

584 Shore Drive

New Windsor, NY

Courtesy of UNITED RE HUDSON VALLEY EDGE
View 210 Dairy Lane New Windsor, NY MLS# 1040427
  • Virtual Tour
1 of 36
$525,000
4

Beds

3.0

Baths

2,092

Sq.Ft.

210 Dairy Lane

New Windsor, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 20 Mecca Drive New Windsor, NY MLS# 1066752
  • Recently Listed
1 of 41
$525,000
4

Beds

2.1

Baths

1,864

Sq.Ft.

20 Mecca Drive

New Windsor, NY

Courtesy of HOWARD HANNA RAND REALTY
View 2173 Little Britain Road New Windsor, NY MLS# 1071337
$524,999
3

Beds

2.0

Baths

1,908

Sq.Ft.

2173 Little Britain Road

New Windsor, NY

Courtesy of KELLER WILLIAMS REALTY
View 45 Quassaick Avenue New Windsor, NY MLS# 1027715
$519,900
2,592

Sq.Ft.

45 Quassaick Avenue

New Windsor, NY

Courtesy of KELLER WILLIAMS REALTY
View 70 Silver Spring Road New Windsor, NY MLS# 1072161
  • Recently Listed with Virtual Tour
1 of 50
$499,999
5

Beds

2.0

Baths

1,800

Sq.Ft.

70 Silver Spring Road

New Windsor, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 6 Lannis Avenue New Windsor, NY MLS# 1058600
  • Virtual Tour
1 of 26
$499,900
3

Beds

2.1

Baths

2,148

Sq.Ft.

6 Lannis Avenue

New Windsor, NY

Courtesy of EREALTY ADVISORS, INC

About New Windsor

Located just 15 miles north of the United States Military Academy at West Point New Windsor benefits from a significant degree of tourist trade.  The community boasts a rich historic legacy that includes cultural attractions like the Knox Headquarters, the New Windsor Cantonment, Patton House,  Last Encampment, and Edmonston House.  Serving as a bedroom community as well as a center for limited business activity, this reason is home to commuters and those who are employed locally.  Among the recreational amenities are Crestview Lake, sports leagues, ball fields, playgrounds, tennis courts, a skating rink, a senior center, and supervised programs. Metro-North commuter rail service and buses are available to New York City, and several routes link to major thoroughfares: Routes 94, 32, 207, and 300. LaGuardia, Stewart, and Kennedy international airports are all accessible.

Listings in New Windsor, NY

168

Estimated median home price

$487,000
New Windsor NY Homes for Sale & Properties

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

Homes for Sale by Price in New Windsor, NY

Price Count
$0 - 100K 8
$100K - 200K 11
$200K - 300K 13
$300K - 400K 20
$400K - 500K 42
$500K - 600K 22
$600K - 700K 6
$700K - 800K 10
$800K - 900K 18
$900K - 1M 1
$1M - Max 17

Homes for Sale by Type in New Windsor, NY

Property Type Count
Single Family 97
Townhouse 0
Condo 24
Commercial 23
Rental 42
Lots and Land 9
Condo/Town/CoOp 0
CoOp 5
Multi Family 8
Mobile Home 2
Farms 0

(Data as of 11/14/2026)

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.