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
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 125-3 S. Highland Avenue C5 Ossining, NY MLS# 1005870
$159,000
1

Beds

1.0

Baths

750

Sq.Ft.

125-3 S. Highland Avenue C5

Ossining, NY

Courtesy of COLDWELL BANKER REALTY
View 3 Hudson View Hill Ossining, NY MLS# 1004947
  • Recently Listed with 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 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 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
View 41 Ellis Place Ossining, NY MLS# 991931
$550,000
6

Beds

3.0

Baths

2,276

Sq.Ft.

41 Ellis Place

Ossining, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
View 127-1 South Highland Avenue B3 Ossining, NY MLS# 987888
$235,000
2

Beds

1.0

Baths

950

Sq.Ft.

127-1 South Highland Avenue B3

Ossining, NY

Courtesy of HOWARD HANNA RAND REALTY
View 3 Briarcliff Drive S 9 Ossining, NY MLS# 985319
$499,900
3

Beds

2.0

Baths

1,431

Sq.Ft.

3 Briarcliff Drive S 9

Ossining, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 37 Secor Road Ossining, NY MLS# 973600
  • Virtual Tour
1 of 40
$85,000
2

Beds

1.0

Baths

1,380

Sq.Ft.

37 Secor Road

Ossining, NY

Courtesy of THD HOMES LLC
View 9 Nicole Circle 8 Ossining, NY MLS# 968945
$499,900
2

Beds

2.0

Baths

1,400

Sq.Ft.

9 Nicole Circle 8

Ossining, NY

Courtesy of WILLIAM RAVEIS REAL ESTATE
View 19 Samstag Avenue Ossining, NY MLS# 20261587
  • Virtual Tour
1 of 42
$410,000
2

Beds

1.0

Baths

829

Sq.Ft.

19 Samstag Avenue

Ossining, NY

UlsterCountyNY
Courtesy of CENTURY 21 ALLIANCE-NP
View 14 Bridle Path Road Ossining, NY MLS# 981035
$525,000
1

Beds

1.1

Baths

1,152

Sq.Ft.

14 Bridle Path Road

Ossining, NY

Courtesy of KELLER WILLIAMS NY REALTY
View 123-6 S Highland Avenue B6 Ossining, NY MLS# 977288
$235,000
2

Beds

1.0

Baths

950

Sq.Ft.

123-6 S Highland Avenue B6

Ossining, NY

Courtesy of COLDWELL BANKER REALTY

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

106

Estimated median home price

$662,500
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 - 500K12
$500K - 600K13
$600K - 700K17
$700K - 800K16
$800K - 900K9
$900K - 1M2
$1M - Max17

Homes for Sale by Type in Ossining, NY

Property TypeCount
Single Family59
Townhouse0
Condo10
Commercial5
Rental35
Lots and Land4
Condo/Town/CoOp0
CoOp14
Multi Family14
Mobile Home0
Farms0

(Data as of 6/16/2026)

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.