View 116 Chestnut Drive New Windsor, NY MLS# 1001314
  • Recently Listed
1 of 48
$575,000
3

Beds

2.1

Baths

1,900

Sq.Ft.

116 Chestnut Drive

New Windsor, NY

Courtesy of HOWARD HANNA RAND REALTY
View 3510 John Paul Jones Lane New Windsor, NY MLS# 1003884
  • Recently Listed with Virtual Tour
1 of 46
$699,000
4

Beds

2.1

Baths

2,276

Sq.Ft.

3510 John Paul Jones Lane

New Windsor, NY

Courtesy of BHHS HUDSON VALLEY PROPERTIES
View 351 Jackson Avenue New Windsor, NY MLS# 1002827
  • Recently Listed
1 of 49
$699,900
3

Beds

3.1

Baths

2,898

Sq.Ft.

351 Jackson Avenue

New Windsor, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 37 Guernsey Drive New Windsor, NY MLS# 1003311
  • Recently Listed
1 of 38
$625,000
4

Beds

2.1

Baths

2,910

Sq.Ft.

37 Guernsey Drive

New Windsor, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 12 Buttermilk Drive New Windsor, NY MLS# 999187
  • Recently Listed with Virtual Tour
1 of 38
$620,000
4

Beds

2.1

Baths

2,879

Sq.Ft.

12 Buttermilk Drive

New Windsor, NY

Courtesy of HOWARD HANNA RAND REALTY
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 739 Hewitt Lane New Windsor, NY MLS# 989150
$599,000
2

Beds

2.1

Baths

1,768

Sq.Ft.

739 Hewitt Lane

New Windsor, NY

Courtesy of TACTICAL REALTY LLC
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 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 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
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 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 5 Sunrise Terrace New Windsor, NY MLS# 972319
$549,000
4

Beds

2.1

Baths

1,968

Sq.Ft.

5 Sunrise Terrace

New Windsor, NY

Courtesy of TYLER'S ESTATES LLC
View 3105 Betsy Ross Ridge New Windsor, NY MLS# 967103
$649,000
3

Beds

2.1

Baths

1,817

Sq.Ft.

3105 Betsy Ross Ridge

New Windsor, NY

Courtesy of CHRISTIE'S INT. REAL ESTATE
View 3 Windsor Garden Drive New Windsor, NY MLS# 966217
$629,900
4

Beds

2.1

Baths

3,679

Sq.Ft.

3 Windsor Garden Drive

New Windsor, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 69 Old Temple Hill Road New Windsor, NY MLS# 958165
$599,900
2,031

Sq.Ft.

69 Old Temple Hill Road

New Windsor, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 16 Sloop Hill Road New Windsor, NY MLS# 951534
$599,000
2,535

Sq.Ft.

16 Sloop Hill Road

New Windsor, NY

Courtesy of TACTICAL REALTY LLC
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 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

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

132

Estimated median home price

$467,000
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 10
$100K - 200K 6
$200K - 300K 17
$300K - 400K 17
$400K - 500K 25
$500K - 600K 19
$600K - 700K 6
$700K - 800K 8
$800K - 900K 11
$900K - 1M 2
$1M - Max 11

Homes for Sale by Type in New Windsor, NY

Property Type Count
Single Family 82
Townhouse 0
Condo 16
Commercial 15
Rental 39
Lots and Land 9
Condo/Town/CoOp 0
CoOp 6
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/2/2026)

Information deemed reliable but not guaranteed.

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.