View 1 San Giacomo Drive New Windsor, NY MLS# 985453
$565,000
5

Beds

2.1

Baths

1,967

Sq.Ft.

1 San Giacomo Drive

New Windsor, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 209 Summit Drive New Windsor, NY MLS# 971287
  • Virtual Tour
1 of 35
$550,000
3

Beds

2.1

Baths

1,883

Sq.Ft.

209 Summit Drive

New Windsor, NY

Courtesy of HUDSON VALLEY HOME CONNECTION
View 17 Shaker Court New Windsor, NY MLS# 984079
$550,000
5

Beds

2.1

Baths

2,431

Sq.Ft.

17 Shaker Court

New Windsor, NY

Courtesy of DONNA RUFFINO REALTY CORP
The time to sell is now! THE TIME TO SELL IS NOW!
View 721 Hewitt Lane New Windsor, NY MLS# 994561
$549,900
2

Beds

2.1

Baths

1,768

Sq.Ft.

721 Hewitt Lane

New Windsor, NY

Courtesy of Weichert Realtors - Monroe
View 150 Mount Airy Road New Windsor, NY MLS# 1010275
  • Recently Listed
1 of 48
$549,900
5

Beds

4.0

Baths

2,790

Sq.Ft.

150 Mount Airy Road

New Windsor, NY

Courtesy of HOWARD HANNA RAND REALTY
View 4 Shaker Court New Windsor, NY MLS# 1013401
$549,900
4

Beds

3.1

Baths

2,452

Sq.Ft.

4 Shaker Court

New Windsor, NY

Courtesy of HOWARD HANNA RAND REALTY
View 313 Chestnut Avenue New Windsor, NY MLS# 973058
$549,000
4

Beds

3.0

Baths

2,821

Sq.Ft.

313 Chestnut Avenue

New Windsor, NY

Courtesy of KELLER WILLIAMS REALTY
View 84 Guernsey Drive New Windsor, NY MLS# 978712
  • Virtual Tour
1 of 38
$549,000
3

Beds

3.0

Baths

1,736

Sq.Ft.

84 Guernsey Drive

New Windsor, NY

Courtesy of KELLER WILLIAMS REALTY
View 584 Shore Drive New Windsor, NY MLS# 1009591
  • Recently Listed
1 of 35
$547,500
4

Beds

2.1

Baths

1,512

Sq.Ft.

584 Shore Drive

New Windsor, NY

Courtesy of UNITED RE HUDSON VALLEY EDGE
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 1110 -1114 route 94 New Windsor, NY MLS# 829593
$525,000
3

Beds

2.0

Baths

1110 -1114 route 94

New Windsor, NY

Courtesy of REAL ESTATE CONNECTION CORP
View 512 Riley Road New Windsor, NY MLS# 1001952
  • Virtual Tour
1 of 46
$525,000
3

Beds

1.0

Baths

960

Sq.Ft.

512 Riley Road

New Windsor, NY

Courtesy of BHG REAL ESTATE GREEN TEAM
View 15 Guernsey Drive New Windsor, NY MLS# 1014088
  • Recently Listed
1 of 34
$525,000
4

Beds

2.1

Baths

2,052

Sq.Ft.

15 Guernsey Drive

New Windsor, NY

Courtesy of KELLER WILLIAMS VILLAGE SQ RLT
View 8 Shaker Court New Windsor, NY MLS# 1009500
  • Recently Listed
1 of 32
$524,999
5

Beds

2.1

Baths

2,821

Sq.Ft.

8 Shaker Court

New Windsor, NY

Courtesy of KELLER WILLIAMS RLTY INTEGRITY
View 263 Riley Road New Windsor, NY MLS# 000031
$519,900
4

Beds

2.0

Baths

2,432

Sq.Ft.

263 Riley Road

New Windsor, NY

Courtesy of CURASI REALTY, INC.
View 505 Iron Forge Lane New Windsor, NY MLS# 977237
$515,000
3

Beds

2.2

Baths

2,550

Sq.Ft.

505 Iron Forge Lane

New Windsor, NY

Courtesy of EREALTY ADVISORS, INC
View 14 Creamery Drive New Windsor, NY MLS# 993436
$499,900
3

Beds

2.1

Baths

2,020

Sq.Ft.

14 Creamery Drive

New Windsor, NY

Courtesy of KELLER WILLIAMS PRESTIGE PROP
View 28 Park Hill Drive New Windsor, NY MLS# 1003023
  • Recently Listed with Virtual Tour
1 of 50
$499,900
3

Beds

2.1

Baths

1,513

Sq.Ft.

28 Park Hill Drive

New Windsor, NY

Courtesy of RE-MAX EXPERIENCE
View 0 Rt-94 New Windsor, NY MLS# 927873
$499,000

0 Rt-94

New Windsor, NY

Courtesy of KELLER WILLIAMS REALTY
View 45 Quassaick Avenue New Windsor, NY MLS# 959992
$499,000
2,592

Sq.Ft.

45 Quassaick Avenue

New Windsor, NY

Courtesy of JOHN J LEASE REALTORS 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

152

Estimated median home price

$460,827
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

PriceCount
$0 - 100K12
$100K - 200K7
$200K - 300K17
$300K - 400K24
$400K - 500K30
$500K - 600K22
$600K - 700K3
$700K - 800K11
$800K - 900K13
$900K - 1M2
$1M - Max11

Homes for Sale by Type in New Windsor, NY

Property TypeCount
Single Family95
Townhouse0
Condo18
Commercial16
Rental43
Lots and Land9
Condo/Town/CoOp0
CoOp7
Multi Family6
Mobile Home1
Farms0

(Data as of 6/23/2026)

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.

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