Homes Under $500K in Ossining, NY

Save search

3 beds New construction With a pool

Hide Map

10 Listings

Map

Homes Under $500K in Ossining, NY

10 Listings

35Active

10 listings

Homes Under $500K in Ossining, NY

Hide Map

10 Listings

Map

Homes Under $500K in Ossining, NY

10 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

35Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

$489,000

2 bd · 2 ba · 1,248 sqft

1203 Eagle Bay Drive, Ossining, NY

Roman Vladimirsky · Keller Williams NY Realty

27Active

$228,000

2 bd · 1 ba · 950 sqft

127-1 S Highland Avenue B5, Ossining, NY

Christopher Felice · Howard Hanna Rand Realty

37Active

$399,000

1 bd · 1 ba · 832 sqft

58 Hudson View Hill, Ossining, NY

Cristina Gameiro · Howard Hanna Rand Realty

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

12Active

$350,000

1 bd · 1 ba · 815 sqft

4 Briarcliff Drive S 9, Ossining, NY

Deanna Hansen · Howard Hanna Rand Realty

30Active

$349,900

1 bd · 1 ba · 700 sqft

1 Briarcliff Drive S 4, Ossining, NY

Jean-Charles DeOliveira Scappaticc · ERA Insite Realty Services

33Active

$375,000

1 bd · 2 ba · 1,158 sqft

3 Davids Lane, Ossining, NY

Karen Stroub · Corcoran Legends Realty

22Active

$425,000

1 bd · 2 ba · 948 sqft

17 Davids Lane, Ossining, NY

Gregory Kane · Kane & Associates

23Active

$229,222

2 bd · 1 ba · 900 sqft

119 S Highland Avenue 5E, Ossining, NY

Mark J. Seiden · Mark Seiden Real Estate Team

Price Reduced12Active

$150,000

1 bd · 1 ba · 750 sqft

129-3 S Highland Avenue a2, Ossining, NY

Jose Cruz · Douglas Elliman Real Estate

Price Reduced42Active

$230,000

2 bd · 1 ba · 950 sqft

127-1 South Highland Avenue B3, Ossining, NY

Jane Rodman · Howard Hanna Rand Realty

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

Ossining housing market

August 2026

Selling at 103.5% of asking price

Buyers here are paying above asking. MLS · 27 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $667,500$535,750–$863,750 typical range
Price per sq. ft.: $401
Sales: 30
Paid in cash: 40.0%

Homes on the market · MLS, as of Aug 24, 2026–Aug 31, 2026

Median list price: $839,000
Homes for sale: 37
Median days on market: 15 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 1.2%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 20, 2026

Median home size: 1,669 sq. ft.

Ossining, NY community profile

Population: 27,903
Median income: $89,811
Housing units: 10,293
People per sq. mi.: 1,924.3
Area: 14.5 sq. mi.

Source: HJN community data

Explore Ossining homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

Ossining, NY community profile

Population: 27,903
Median income: $89,811
Housing units: 10,293
People per sq. mi.: 1,924.3
Area: 14.5 sq. mi.

Source: HJN community data

Ossining housing market

August 2026

Selling at 103.5% of asking price

Buyers here are paying above asking. MLS · 27 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $667,500$535,750–$863,750 typical range
Price per sq. ft.: $401
Sales: 30
Paid in cash: 40.0%

Homes on the market · MLS, as of Aug 24, 2026–Aug 31, 2026

Median list price: $839,000
Homes for sale: 37
Median days on market: 15 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 1.2%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 20, 2026

Median home size: 1,669 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Ossining housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of Aug 24, 2026–Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 20, 2026

Ossining, NY community profile

Explore Ossining homes

Your local brokerage

Listing data & MLS disclosures

Ossining, NY community profile

Ossining housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of Aug 24, 2026–Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 20, 2026