Ossining, NY Homes

• 

  

  

  /38

  $2,900,000

  $600K PRICE DROP

  • 7 Beds
  • 7 Baths
  • 5,502 Sq Ft

  83 Somerstown Rd, Ossining, NY 10562

  Steeped in local history and once owned by the Gilded Age Van Cortlandt family, gracious Rose Lodge is an inviting and beautifully restored historic estate—not landmarked—offering modern living and exceptional privacy on 17.9 acres. The property enjoys sweeping views across a perfectly sited in-ground pool, terraced gardens, expansive flat croquet lawn, and private lake, creating a serene country

  Dalia Valdes Julia B Fee Sothebys Int. Rlty

  83 Somerstown Rd, Ossining, NY 10562
• 

  $540,000

  Sold Mar 23, 2026

  39 Hamilton Ave, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 2,198 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Above List Price
  • $246/SF
  • 45 Days On Market

  Current Estimated Value $536,049

  Last Listing Agent Greg Kane Kane & Associates

  39 Hamilton Ave, Ossining, NY 10562
• 

  Est $159,000

  Not Listed For Sale

  121 S Highland Ave Unit 3F, Ossining, NY 10562

  • Studio
  • 1 Bath
  • 650 Sq Ft
  • Built 1964

  121 S Highland Ave Unit 3F, Ossining, NY 10562

  Last Sold Summary

  • 45% Above List Price
  • $169/SF
  • 42 Days On Market

  • Last Sold Price $110,000
  • Jan 16, 2025

  Last Listing Agent Nancy Keller Keller Williams Realty Partner
• 

  

  

  /30

  $425,000

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft

  19 Samstag Ave, Ossining, NY 10562

  This two bedroom one bath bungalow set high above the Hudson with sweeping river views, this property offers a rare opportunity to enjoy the charm, convenience, and lifestyle that define Ossining living. Welcome to 19 Samstag Ave, a home perfectly positioned for those seeking both tranquility and connectivity. Enjoy gorgeous Hudson River vistas and the natural beauty that surrounds this historic

  Angelina Cozza Century 21 Alliance Rlty Group

  19 Samstag Ave, Ossining, NY 10562
• 

  $850,000

  Sold May 15, 2025

  19 High Ridge Rd, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 2,715 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Below List Price
  • $313/SF
  • 15 Days On Market

  Current Estimated Value $889,228

  Last Listing Agent Gay Marglin Houlihan Lawrence Inc.

  19 High Ridge Rd, Ossining, NY 10562
• 

  Not Listed For Sale

  106 Kemeys Ave Unit 6, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,298 Sq Ft
  • Built 1975

  106 Kemeys Ave Unit 6, Briarcliff Manor, NY 10510

  Last Sold Summary

  • $396/SF
  • 13 Days On Market

  • Last Sold Price $514,000
  • May 05, 2025

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team
• 

  

  /36

  $799,000

  Pending

  • 2 Beds
  • 3.5 Baths
  • 2,229 Sq Ft

  78 Hudson Watch Dr, Ossining, NY 10562

  Welcome to 78 Hudson Watch Drive, a stunning 2-bedroom, 3.5-bath tri-level townhouse offering an unparalleled luxury lifestyle. Experience breathtaking Hudson River views spanning all three floors of this meticulously maintained home. Step inside to a truly inviting space featuring a spacious sunken living room anchored by a cozy gas fireplace. The layout is wonderful for entertaining, leading

  Bradley Fischer Julia B Fee Sothebys Int. Rlty

  78 Hudson Watch Dr, Ossining, NY 10562
• 

  $925,000

  Sold Oct 06, 2025

  35 Mystic Dr, Ossining, NY 10562

  • 2 Beds
  • 3.5 Baths
  • 2,700 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Above List Price
  • $343/SF
  • 20 Days On Market

  Current Estimated Value $936,199

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  35 Mystic Dr, Ossining, NY 10562
• 

  Est $714,862

  Not Listed For Sale

  55 Briarbrook Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 2,099 Sq Ft
  • Built 2001

  55 Briarbrook Dr, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 4% Above List Price
  • $326/SF
  • 34 Days On Market

  • Last Sold Price $685,000
  • May 07, 2025

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.
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  /33

  $340,000

  Pending

  • 1 Bed
  • 1 Bath
  • 894 Sq Ft

  9 Nicole Cir Unit 3, Ossining, NY 10562

  Pet-friendly Hudson View condo with serene wooded surroundings. This bright and spacious home features a cozy fireplace in the living room with access to a private deck. The home includes generously sized bedroom with ample storage. Additional highlights include assigned parking and ample guest parking. Community amenities include a pool, clubhouse, fitness center, tennis and basketball courts,

  Sandra Genaro Keller Williams Realty Partner

  9 Nicole Cir Unit 3, Ossining, NY 10562
• 

  $653,000

  Sold Oct 22, 2025

  407 Glenwood Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,837 Sq Ft
  • Built 2001

  Last Sold Summary

  • 9% Above List Price
  • $355/SF
  • 19 Days On Market

  Current Estimated Value $669,809

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.

  407 Glenwood Dr, Briarcliff Manor, NY 10510
• 

  Est $707,698

  Not Listed For Sale

  9 River Pkwy, Briarcliff Manor, NY 10510

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1976

  9 River Pkwy, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 20% Above List Price
  • $348/SF
  • 270 Days On Market

  • Last Sold Price $591,000
  • May 06, 2024

  Last Listing Agent Joe Hasselt Joe Hasselt Real Estate
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  /39

  $2,389,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 5,516 Sq Ft

  178 Hirst Rd, Briarcliff Manor, NY 10510

  Welcome to Briarcliff Manor! Perched gracefully atop a hill on a quiet cul-de-sac, beautifully maintained, this exceptional sprawling 5-bedroom, 4.5-bath custom Colonial offers privacy, elegance, and refined living in one of the area’s most sought-after neighborhoods.Meticulously maintained and thoughtfully designed, this sun-drenched residence showcases generous proportions throughout. The

  Bonnie Paolucci Elk Homes Realty LLC

  178 Hirst Rd, Briarcliff Manor, NY 10510
• 

  $320,000

  Sold Dec 29, 2025

  20 Maple Place, Ossining, NY 10562

  • 5 Beds
  • 1.5 Baths
  • 2,880 Sq Ft
  • Built 1870

  Last Sold Summary

  • 12% Below List Price
  • $111/SF
  • 284 Days On Market

  Current Estimated Value $528,891

  Last Listing Agent Gary Leogrande Keller Williams NY Realty

  20 Maple Place, Ossining, NY 10562
• 

  Not Listed For Sale

  17 Steven Dr Unit 3, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,710 Sq Ft
  • Built 1995

  17 Steven Dr Unit 3, Ossining, NY 10562

  Last Sold Summary

  • $254/SF
  • 21 Days On Market

  • Last Sold Price $435,000
  • Feb 20, 2025

  Last Listing Agent Pamela Rotando Coldwell Banker Realty
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  /43

  $675,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,959 Sq Ft

  24 Highview Rd, Ossining, NY 10562

  Welcome to 24 Highview Road, a classic Split-Level home offering the perfect blend of privacy and potential on a rare 1.32-acre lot in the Town of New Castle. This 3-bedroom, 2.1-bathroom residence features 1,959 square feet of living space with several recent high-value mechanical and interior upgrades. The main level boasts a spacious living room with a cozy fireplace and a seamless flow into

  Elizabeth Koski Coldwell Banker Realty

  24 Highview Rd, Ossining, NY 10562
• 

  $150,000

  Sold Jan 13, 2026

  117 S Highland Ave Unit 6J, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1969

  Last Sold Summary

  • $200/SF
  • 9 Days On Market

  Current Estimated Value $159,000

  Last Listing Agent Peter Raider Real Broker NY LLC

  117 S Highland Ave Unit 6J, Ossining, NY 10562
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  Not Listed For Sale

  79 Main St, Ossining, NY 10562

  • 8 Beds
  • 4 Baths
  • 3,888 Sq Ft
  • Built 1880

  79 Main St, Ossining, NY 10562

  Last Sold Summary

  • $240/SF
  • 10 Days On Market

  • Last Sold Price $934,500
  • Feb 26, 2025

  Last Listing Agent Arafat Ibrahim AI Realty Brokerage LLC
• 

  

  /50

  $2,995,000

  • 5 Beds
  • 7 Baths
  • 7,931 Sq Ft

  36 Revolutionary Rd, Briarcliff Manor, NY 10510

  There are homes... and then there are places that feel quietly set apart from the world around them.Tucked behind a gentle approach, on nearly four private acres in the heart of Briarcliff Manor, 36 Revolutionary Road reveals itself slowly, intentionally... like a secret meant only for those who understand what true luxury feels like.This is not just a home. This is a legacy

  Elaine Wasserman Houlihan Lawrence Inc.

  36 Revolutionary Rd, Briarcliff Manor, NY 10510
• 

  $1,650,000

  Sold Apr 24, 2026

  2 Lodge Rd, Briarcliff Manor, NY 10510

  • 6 Beds
  • 5.5 Baths
  • 5,700 Sq Ft
  • Built 1996

  Last Sold Summary

  • $289/SF
  • 12 Days On Market

  Current Estimated Value $1,867,676

  Last Listing Agent Arya Rabinovits eRealty Advisors, Inc

  2 Lodge Rd, Briarcliff Manor, NY 10510
• 

  Est $664,038

  Not Listed For Sale

  8 Robert Rinaldi Ln, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,566 Sq Ft
  • Built 2015

  8 Robert Rinaldi Ln, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 15% Above List Price
  • $367/SF
  • 39 Days On Market

  • Last Sold Price $575,000
  • Dec 10, 2024

  Last Listing Agent Mary Ann Tighe Houlihan Lawrence Inc.
• 

  

  /25

  $609,000

  • 2 Beds
  • 2.5 Baths
  • 1,547 Sq Ft

  63 Deerfield Ln Unit 63, Ossining, NY 10562

  Welcome to Deerfield Condominium Complex....A middle unit recently updated. This unit features attached garage, 2 private decks, updated eat-in kitchen, freshly painted and new carpeting. This unit is a tri level home. Perfect for today's buyer. Deerfield Community is close to 9A, Croton on Hudson railroad station, and all that Ossining offers.

  Thomas Burns Coldwell Banker Realty

  63 Deerfield Ln Unit 63, Ossining, NY 10562
• 

  $445,000

  Sold Oct 07, 2025

  705 Briarcliff Dr S, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1977

  Last Sold Summary

  • 2% Above List Price
  • $345/SF
  • 46 Days On Market

  Last Listing Agent Cindy Cassuto Corcoran Legends Realty

  705 Briarcliff Dr S, Ossining, NY 10562
• 

  Not Listed For Sale

  506 Kemeys Cove Unit 506, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,298 Sq Ft
  • Built 1975

  506 Kemeys Cove Unit 506, Ossining, NY 10562

  Last Sold Summary

  • $347/SF
  • 26 Days On Market

  • Last Sold Price $450,500
  • Aug 19, 2024

  Last Listing Agent Madelyn Ricciardi Houlihan Lawrence Inc.
• 

  

  /50

  $1,300,000

  • 5 Beds
  • 3.5 Baths
  • 2,780 Sq Ft

  75 Chappaqua Rd, Briarcliff Manor, NY 10510

  THIS HOME CAN BE SOLD AS A PACKAGE DEAL WITH TWO ADDITION LOTS Welcome to 75 Chappaqua Road, a total spacious 4,200 sq ft single-family home in Briarcliff Manor, offering generous living space, abundant natural light, and timeless character. The home features a traditional layout with a formal living room, family room, formal dining room, and a convenient main-level bath. The kitchen and

  Bryant Moran YourHomeSold Guaranteed Realty

  75 Chappaqua Rd, Briarcliff Manor, NY 10510
• 

  $490,000

  Sold Jul 31, 2025

  49 Pine Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,026 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Above List Price
  • $478/SF
  • 36 Days On Market

  Current Estimated Value $515,859

  Last Listing Agent Kelly Castiglione Coldwell Banker Realty

  49 Pine Ave, Ossining, NY 10562
• 

  Not Listed For Sale

  123 S Highland Ave Unit B5, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1962

  123 S Highland Ave Unit B5, Ossining, NY 10562

  Last Sold Summary

  • $211/SF
  • 22 Days On Market

  • Last Sold Price $190,000
  • Jul 01, 2024

  Last Listing Agent Jamie Jamieson Compass Greater NY, LLC
• 

  

  /32

  $710,000

  $10K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,860 Sq Ft

  1 Edward St, Ossining, NY 10562

  Well-maintained two-unit property in the heart of Ossining, fully renovated in 2020 and offering a strong combination of space, convenience, and versatility. The building features a spacious three-bedroom unit over a two-bedroom walk-up, providing an ideal opportunity for owner-occupants or investors. Both units benefit from updated finishes completed during the 2020 renovation, offering modern

  Tana McGuire eXp Realty

  1 Edward St, Ossining, NY 10562
• 

  $699,000

  Sold Dec 19, 2025

  5 Cedar Place, Ossining, NY 10562

  • 3 Beds
  • 3 Baths
  • 2,272 Sq Ft
  • Built 1931

  Last Sold Summary

  • 4% Below List Price
  • $308/SF
  • 73 Days On Market

  Current Estimated Value $693,818

  Last Listing Agent Brian Perez Century 21 Hire Realty

  5 Cedar Place, Ossining, NY 10562
• 

  Est $944,503

  Not Listed For Sale

  45 Mystic Dr, Ossining, NY 10562

  • 2 Beds
  • 3.5 Baths
  • 2,715 Sq Ft
  • Built 1996

  45 Mystic Dr, Ossining, NY 10562

  Last Sold Summary

  • $348/SF
  • 79 Days On Market

  • Last Sold Price $945,000
  • Sep 12, 2023

  Last Listing Agent Gay Marglin Houlihan Lawrence Inc.
• 

  

  /37

  $800,000

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft

  16 Rockledge Ave Unit 6D-2, Ossining, NY 10562

  THIS IS THE VIEW YOU’VE BEEN DREAMING OF! HUDSON RIVER VIEWS FROM EACH ROOM of this sunny-corner unit, 3-bedroom, 2 Full Bath co-op apartment with a Private Terrace, in the sought-after riverfront community of Scarborough Manor. This unit features a kitchen with quarry tiled floor, formal dining room, oversized living room with panoramic views and a door to your private terrace. The primary

  Sue Hartwell Corcoran Legends Realty

  16 Rockledge Ave Unit 6D-2, Ossining, NY 10562
• 

  $1,264,064

  Sold Jun 24, 2025

  35 Candlewood Ct, Briarcliff Manor, NY 10510

  • 4 Beds
  • 3.5 Baths
  • 2,715 Sq Ft
  • Built 1998

  Last Sold Summary

  • 29% Above List Price
  • $466/SF
  • 6 Days On Market

  Current Estimated Value $1,279,385

  Last Listing Agent Kathleen Griffin Houlihan Lawrence Inc.

  35 Candlewood Ct, Briarcliff Manor, NY 10510
• 

  Est $159,000

  Not Listed For Sale

  117 S Highland Ave Unit 5J, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1962

  117 S Highland Ave Unit 5J, Ossining, NY 10562

  Last Sold Summary

  • 1% Below List Price
  • $213/SF
  • 114 Days On Market

  • Last Sold Price $159,900
  • Feb 13, 2025

  Last Listing Agent Lisa Emanuele ERA Insite Realty Services
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  /34

  $899,000

  $50K PRICE DROP Pending

  • 7 Beds
  • 3 Baths
  • 2,224 Sq Ft

  25 William St, Ossining, NY 10562

  This spacious three-family home in Ossining offers three full stories plus a finished basement, perfect for multi-generational living or rental income. Each unit features its own living areas, kitchen, and bedrooms, providing privacy and flexibility for family members or tenants. The first floor includes a living room, central kitchen and dining area, three bedrooms, and a full bath. The second

  Etan Hakimi Mitra Hakimi Realty Group LLC

  25 William St, Ossining, NY 10562
• 

  $635,000

  Sold Dec 16, 2025

  7 Birchbrook Rd, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 2,049 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Below List Price
  • $310/SF
  • 55 Days On Market

  Current Estimated Value $652,156

  Last Listing Agent John Buoninfante Real Broker NY LLC

  7 Birchbrook Rd, Ossining, NY 10562
• 

  Est $522,767

  Not Listed For Sale

  1210 Eagle Bay Dr, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1982

  1210 Eagle Bay Dr, Ossining, NY 10562

  Last Sold Summary

  • 13% Above List Price
  • $372/SF
  • 26 Days On Market

  • Last Sold Price $464,000
  • Aug 18, 2023

  Last Listing Agent Kristen da Costa Coldwell Banker Realty
• 

  

  /48

  $2,699,000

  $296K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,282 Sq Ft

  132 Ridgecrest Rd, Briarcliff Manor, NY 10510

  BREATHTAKING YEAR ROUND HUDSON RIVER PANORAMIC VIEWS define this iconic Mid-Century Modern residence! Located on Briarcliff’s coveted Ridgecrest Road in the highly sought-after Briarcliff Manor School District, this modern masterpiece, being sold FURNISHED, is well known in architectural and interior design circles. Ideally located just minutes from the Scarborough Metro-North station, this home

  Cindy Glynn Compass Greater NY, LLC

  132 Ridgecrest Rd, Briarcliff Manor, NY 10510
• 

  $610,000

  Sold Nov 14, 2025

  73 van Cortlandt Ave, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft
  • Built 1882

  Last Sold Summary

  • 2% Above List Price
  • $412/SF
  • 56 Days On Market

  Current Estimated Value $616,300

  Last Listing Agent Patricia Wolny Corcoran Legends Realty

  73 van Cortlandt Ave, Ossining, NY 10562
• 

  Est $215,000

  Not Listed For Sale

  129 S Highland Ave Unit B4, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 890 Sq Ft
  • Built 1962

  129 S Highland Ave Unit B4, Ossining, NY 10562

  Last Sold Summary

  • 6% Above List Price
  • $228/SF
  • 23 Days On Market

  • Last Sold Price $203,000
  • Sep 15, 2023

  Last Listing Agent Anthony Sarro At Home With Yara Realty
• 

  

  /45

  $1,799,999

  • 5 Beds
  • 4.5 Baths
  • 6,458 Sq Ft

  11 Hollow Tree Rd, Briarcliff Manor, NY 10510

  Nestled on a quiet cul-de-sac in Briarcliff Manor, this inviting 5-bedroom, 4.5 bath home combines space, light, and a layout that simply works for the way people live today. A grand entry foyer with hardwood floors and inlay detail sets the tone, opening to well-proportioned formal and informal spaces suited for both everyday living and entertaining. The living room features recessed lighting

  Suzan Zeolla Houlihan Lawrence Inc.

  11 Hollow Tree Rd, Briarcliff Manor, NY 10510

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