View 53 Pleasantville Road Ossining, NY MLS# 1014067
$507,000
2

Beds

1.0

Baths

768

Sq.Ft.

53 Pleasantville Road

Ossining, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 126 Croton Avenue Ossining, NY MLS# 1013780
  • Recently Listed
1 of 10
$299,000
2

Beds

1.0

Baths

849

Sq.Ft.

126 Croton Avenue

Ossining, NY

Courtesy of EREALTY ADVISORS, INC
View Chappaqua Road Ossining, NY MLS# 1013829
  • Recently Listed
1 of 4
$180,000
Studio

Beds

0.0

Baths

34,624

Sq.Ft.

Chappaqua Road

Ossining, NY

Courtesy of YOURHOMESOLD GUARANTEED REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 122 Woods Brooke Circle Ossining, NY MLS# 1010405
  • Recently Listed
1 of 30
$575,000
2

Beds

2.1

Baths

1,390

Sq.Ft.

122 Woods Brooke Circle

Ossining, NY

Courtesy of CORCORAN LEGENDS REALTY
View 16 Sherwood Avenue Ossining, NY MLS# 1010005
  • Recently Listed with Virtual Tour
1 of 36
$599,000
3

Beds

1.0

Baths

1,288

Sq.Ft.

16 Sherwood Avenue

Ossining, NY

Courtesy of COMPASS GREATER NY, LLC
View 237 Spring Street Ossining, NY MLS# 1005194
  • Recently Listed
1 of 16
$500,000
3

Beds

3.0

Baths

1,992

Sq.Ft.

237 Spring Street

Ossining, NY

Courtesy of DOUGLAS ELLIMAN REAL ESTATE
View 16 Rockledge Avenue 2D-1 Ossining, NY MLS# 1007742
  • Recently Listed
1 of 24
$350,000
1

Beds

1.0

Baths

1,250

Sq.Ft.

16 Rockledge Avenue 2D-1

Ossining, NY

Courtesy of COLDWELL BANKER REALTY
View 121 South Highland Avenue 2K Ossining, NY MLS# 1005486
$214,999
2

Beds

1.0

Baths

900

Sq.Ft.

121 South Highland Avenue 2K

Ossining, NY

Courtesy of CONCIERGE REALTY
View 33 Maurice Avenue Ossining, NY MLS# 1001582
  • Recently Listed
1 of 29
$555,000
3

Beds

1.1

Baths

1,280

Sq.Ft.

33 Maurice Avenue

Ossining, NY

Courtesy of KELLER WILLIAMS REALTY GROUP
View 281 Croton Dam Road A Ossining, NY MLS# 1006310
  • Recently Listed
1 of 25
$450,000
3

Beds

2.0

Baths

882

Sq.Ft.

281 Croton Dam Road A

Ossining, NY

Courtesy of KELLER WILLIAMS REALTY PARTNER
View 5 Meadowbrook Drive Ossining, NY MLS# 1004276
$599,000
3

Beds

1.1

Baths

1,560

Sq.Ft.

5 Meadowbrook Drive

Ossining, NY

Courtesy of RE/MAX PRESTIGE PROPERTIES
View 125-3 S. Highland Avenue C5 Ossining, NY MLS# 1005870
  • Recently Listed
1 of 16
OPEN HOUSE: Saturday 6/20 12:00 PM - 2:00 PM
$159,000
1

Beds

1.0

Baths

750

Sq.Ft.

125-3 S. Highland Avenue C5

Ossining, NY

Courtesy of COLDWELL BANKER REALTY
View 5 Maria Lane Ossining, NY MLS# 1004901
$299,000
4

Beds

2.1

Baths

2,374

Sq.Ft.

5 Maria Lane

Ossining, NY

Courtesy of JULIA B FEE SOTHEBYS INT. RLTY
View 3 Hudson View Hill Ossining, NY MLS# 1004947
  • Virtual Tour
1 of 23
$475,000
2

Beds

1.1

Baths

1,311

Sq.Ft.

3 Hudson View Hill

Ossining, NY

Courtesy of KELLER WILLIAMS VILLAGE SQ RLT
View 20 Samstag Avenue Ossining, NY MLS# 995689
$450,000
3

Beds

1.0

Baths

930

Sq.Ft.

20 Samstag Avenue

Ossining, NY

Courtesy of KELLER WILLIAMS REALTY PARTNER
View 42 Lee Avenue Ossining, NY MLS# 993189
$579,000
4

Beds

1.0

Baths

1,296

Sq.Ft.

42 Lee Avenue

Ossining, NY

Courtesy of WILLIAM RAVEIS REAL ESTATE
View 133-3 S Highland Avenue 5B Ossining, NY MLS# 991549
$215,000
2

Beds

1.0

Baths

950

Sq.Ft.

133-3 S Highland Avenue 5B

Ossining, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 19 Samstag Avenue Ossining, NY MLS# 993706
$425,000
2

Beds

1.0

Baths

740

Sq.Ft.

19 Samstag Avenue

Ossining, NY

Courtesy of CENTURY 21 ALLIANCE RLTY GROUP
View 41 Clinton Avenue Ossining, NY MLS# 989545
  • Virtual Tour
1 of 44
$599,000
3

Beds

3.0

Baths

1,668

Sq.Ft.

41 Clinton Avenue

Ossining, NY

Courtesy of COMPASS GREATER NY, LLC
View 18 2nd Avenue Ossining, NY MLS# 991096
  • Virtual Tour
1 of 31
$529,000
2

Beds

1.0

Baths

912

Sq.Ft.

18 2nd Avenue

Ossining, NY

Courtesy of RE/MAX TOWN & COUNTRY

About Ossining

The town of Ossining provides a tranquil residential escape from bustling city life.  Located in close proximity to the picturesque Hudson River, this area is rich in local history and small-town charm.  Offering an ideal location for commuters, this residential community is also home to a variety of businesses that are clustered along the North State Road corridor.  Ossining has many types of housing available, from modest homes to luxurious estates, and a diversified population.  Ossining boasts shopping centers; mini-malls, individual stores, and a historic downtown shopping area, which includes a variety of restaurants.  The efficient transportation facilities in this area include commuter rail to New York City via Metro-North, Routes 9 and 9A, the Taconic State Parkway, and Saw Mill River Parkway. 

Listings in Ossining, NY

107

Estimated median home price

$650,000
Ossining NY Homes for Sale & Properties

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

Homes for Sale by Price in Ossining, NY

PriceCount
$0 - 100K1
$100K - 200K4
$200K - 300K10
$300K - 400K5
$400K - 500K11
$500K - 600K13
$600K - 700K19
$700K - 800K16
$800K - 900K9
$900K - 1M2
$1M - Max17

Homes for Sale by Type in Ossining, NY

Property TypeCount
Single Family58
Townhouse0
Condo12
Commercial5
Rental36
Lots and Land4
Condo/Town/CoOp0
CoOp14
Multi Family14
Mobile Home0
Farms0

(Data as of 6/17/2026)

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.