Ossining, NY Homes

• 

  

  

  /43

  $779,900

  $20K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,563 Sq Ft

  65 Morningside Dr, Ossining, NY 10562

  Take A Stroll in the Park...The market has waited 50 years for this true gem of a home to become yours in this special, sought-after quiet and serene residential neighborhood in the unincorporated Town of Ossining. This light and bright three bedroom, two bath ranch house sits on a half-acre lot on the high side of Morningside Drive with beautiful scenic views, and borders the 130-acre Charles K

  Cindy Cassuto Corcoran Legends Realty

  65 Morningside Dr, Ossining, NY 10562
• 

  $845,000

  Sold Jun 26, 2026

  20 Highview Rd, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • Built 1959

  Last Sold Summary

  • 15% Above List Price
  • $505/SF
  • 10 Days On Market

  Current Estimated Value $768,449

  Last Listing Agent Yarden Ronen-van Heerden Compass Greater NY, LLC

  20 Highview Rd, Ossining, NY 10562
• 

  Est $788,634

  Not Listed For Sale

  17 Adams Rd, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft
  • Built 1958

  17 Adams Rd, Ossining, NY 10562

  Last Sold Summary

  • 15 Days On Market
• 

  

  

  /19

  $624,000

  $236K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 3,128 Sq Ft

  398 Illington Rd, Ossining, NY 10562

  A Charming Farmhouse Style Home, Carefully Restored to Blend Historic Character with Modern Comfort. Nestled on 3 acres of landscaped grounds, this inviting residence offers spacious living and serene privacy just minutes from local amenities and commuting routes. The renovations that were made still kept its original charm. Features like the woodwork, beamed ceilings, built-in cabinets, and

  Joann Perna Guardian Realty Center, LLC

  398 Illington Rd, Ossining, NY 10562
• 

  $332,500

  Sold Jan 02, 2026

  16 Rockledge Ave Unit 5B1, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Below List Price
  • $210/SF
  • 94 Days On Market

  Last Listing Agent Melissa Terman River Realty Services, Inc.

  16 Rockledge Ave Unit 5B1, Ossining, NY 10562
• 

  Est $1,720,891

  Not Listed For Sale

  50 Cloverhill Ln, Ossining, NY 10562

  • 5 Beds
  • 4.5 Baths
  • 5,006 Sq Ft
  • Built 2005

  50 Cloverhill Ln, Ossining, NY 10562

  Last Sold Summary

  • 24 Days On Market
• 

  

  /42

  $996,000

  Pending

  • 3 Beds
  • 3 Baths
  • 3,492 Sq Ft

  47 Willow Dr, Briarcliff Manor, NY 10510

  You can’t ask for a more turn-key home! Everything inside has been updated tastefully in the last few years, and the shy 1/2 acre is beautifully landscaped and perfect for entertaining, with a large deck plus back patio and privacy fence in the rear. If you’re looking for a mother-daughter home, or a home office with a separate entrance, this ranch with a walk-out lower level would be perfect for

  Susan Strawgate Code Houlihan Lawrence Inc.

  47 Willow Dr, Briarcliff Manor, NY 10510
• 

  $915,000

  Sold Aug 26, 2025

  11 Pond View Ln, Ossining, NY 10562

  • 2 Beds
  • 3.5 Baths
  • 3,240 Sq Ft
  • Built 1996

  Last Sold Summary

  • 5% Above List Price
  • $282/SF
  • 77 Days On Market

  Last Listing Agent Bill D'Ambrosio Compass Greater NY, LLC

  11 Pond View Ln, Ossining, NY 10562
• 

  Est $1,662,400

  Not Listed For Sale

  1340 Kitchawan Rd, Ossining, NY 10562

  • 8 Beds
  • 6.5 Baths
  • 6,500 Sq Ft
  • Built 1906

  1340 Kitchawan Rd, Ossining, NY 10562

  Last Sold Summary

  • 27 Days On Market
• 

  

  /11

  $950,000

  • 7 Beds
  • 4 Baths

  38 Main St, Ossining, NY 10562

  The subject property is located at 38 Main St, Ossining, NY 10562. Strategically located in Ossining between Water St and Secor Rd. Lot consists of 24ft x 102ft. Includes 4 residential units not subject to rent regulation. Tenants on month-to-month leases. The property consists of (3) 2 bedrooms and (1) 1 bedrooms. This well-maintained 4 unit multifamily building represents a compelling

  Matthew Barbaccia Brix Real Estate Advisors

  38 Main St, Ossining, NY 10562
• 

  $928,000

  Sold Dec 17, 2025

  175 Croton Ave, Ossining, NY 10562

  • 8 Beds
  • 3 Baths
  • 3,648 Sq Ft
  • Built 1900

  Last Sold Summary

  • $254/SF
  • 85 Days On Market

  Current Estimated Value $944,195

  Last Listing Agent Owen Leggio Leggio Realty Group

  175 Croton Ave, Ossining, NY 10562
• 

  Est $921,692

  Not Listed For Sale

  1709 Spring Valley Rd, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 1790

  1709 Spring Valley Rd, Ossining, NY 10562

  Last Sold Summary

  • 18 Days On Market
• 

  

  /36

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  310 Kemeys Ave Unit 3-10, Briarcliff Manor, NY 10510

  As nice as they come. Hudson River views. Totally renovated from top to bottom. New kitchen, new baths, new flooring, new crown molding, recessed lighting, ceiling fans and speakers, new a/c units, expanded and organized closets, new separate laundry closet. Open Living Room/Dining Area with Hudson River Views and slider to patio with awning. Super-efficient galley kitchen outfitted with Bosch

  Stacy Levey William Raveis-New York, LLC

  310 Kemeys Ave Unit 3-10, Briarcliff Manor, NY 10510
• 

  $510,000

  Sold Jan 23, 2026

  608 Kemeys Cove Unit 6-08, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,265 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $403/SF
  • 122 Days On Market

  Last Listing Agent Kareem Kirby Keller Williams Realty NYC Grp

  608 Kemeys Cove Unit 6-08, Briarcliff Manor, NY 10510
• 

  Est $1,005,338

  Not Listed For Sale

  1137 Estates Dr, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft
  • Built 1997

  1137 Estates Dr, Ossining, NY 10562

  Last Sold Summary

  • 41 Days On Market
• 

  

  /27

  $1,250,000

  $100K PRICE DROP Pending

  • 7 Beds
  • 4 Baths
  • 2,967 Sq Ft

  858 Pleasantville Rd, Briarcliff Manor, NY 10510

  Don't miss this rare opportunity in the coveted Briarcliff Manor School District; Welcome to this exceptional multi-family home located in the highly desirable village of Briarcliff Manor, offering a unique potential to live in one unit while collecting rental income from the others. Located within the award-winning Briarcliff Manor School District, this property presents a unique blend of

  Nancy Beard Houlihan Lawrence Inc.

  858 Pleasantville Rd, Briarcliff Manor, NY 10510
• 

  $645,000

  Sold Aug 13, 2025

  25 Brookville Ave, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 1,673 Sq Ft
  • Built 1890

  Last Sold Summary

  • $386/SF
  • 40 Days On Market

  Current Estimated Value $676,517

  Last Listing Agent Heather Bouza Compass Greater NY, LLC

  25 Brookville Ave, Ossining, NY 10562
• 

  Est $866,827

  Not Listed For Sale

  376 Illington Rd, Ossining, NY 10562

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 1929

  376 Illington Rd, Ossining, NY 10562

  Last Sold Summary

  • 65 Days On Market
• 

  

  /50

  $3,100,000

  Coming Soon

  • 3 Beds
  • 5 Baths
  • 6,091 Sq Ft

  23 Inningwood Rd, Ossining, NY 10562

  No words or photos will justify the Magical beauty of this luxurious home. The woodwork in this custom built home was done by craftsman Mark Pedley, a very talented carpenter/joiner from Vermont who previously worked in Palaces in Jordan. The home is flawless and impeccable with spa like bathrooms, a gourmet kitchen, outdoor grilling area, sauna, steam bath and jacuzzi, with marble, granite and

  Dee Rabady Woodfront Realty, Inc.

  23 Inningwood Rd, Ossining, NY 10562
• 

  $200,000

  Sold Aug 13, 2025

  121 S Highland Ave Unit 4B, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1964

  Last Sold Summary

  • 12% Above List Price
  • $222/SF
  • 20 Days On Market

  Last Listing Agent Jeannette Boccini Coldwell Banker Realty

  121 S Highland Ave Unit 4B, Ossining, NY 10562
• 

  Est $837,240

  Not Listed For Sale

  5 Ridgeview Dr, Ossining, NY 10562

  • 4 Beds
  • 3 Baths
  • 2,192 Sq Ft
  • Built 1952

  5 Ridgeview Dr, Ossining, NY 10562

  Last Sold Summary

  • 36 Days On Market
• 

  

  /33

  $899,222

  $100K PRICE INCREASE Pending

  • 3 Beds
  • 2 Baths
  • 2,056 Sq Ft

  74 Hungerford Rd, Briarcliff Manor, NY 10510

  Nestled in a quiet neighborhood near a local park, this wonderful split-level home in the highly sought-after village of Briarcliff Manor offers the perfect blend of comfort, style, and community living. Step inside to discover an updated eat-in kitchen featuring granite countertops and built-in seating—ideal for both everyday living and casual entertaining. The open-concept living and dining

  Mark Seiden Mark Seiden Real Estate Team

  74 Hungerford Rd, Briarcliff Manor, NY 10510
• 

  $425,000

  Sold Oct 28, 2025

  29 William St, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 1,688 Sq Ft
  • Built 1912

  Last Sold Summary

  • 6% Above List Price
  • $252/SF
  • 6 Days On Market

  Current Estimated Value $470,873

  Last Listing Agent Justin Landon Howard Hanna Rand Realty

  29 William St, Ossining, NY 10562
• 

  Est $619,428

  Not Listed For Sale

  18 Ridgeview Dr, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft
  • Built 1947

  18 Ridgeview Dr, Ossining, NY 10562

  Last Sold Summary

  • 13 Days On Market
• 

  

  /6

  $1,899,000

  • 4 Beds
  • 3.5 Baths
  • 2,693 Sq Ft

  94 Somerstown Rd, Ossining, NY 10562

  Rooted in the aesthetic of Frank Lloyd Wright's Usonia District and inspired by the classic era of mid-century design, Moradia is abrand-new community of to-be-built, high-end residences. Located along a picturesque road in historic Ossining, NY, each home is set on a beautiful parcel of virgin land. The homesites are elevated and private-ranging between 1 1/2 and 3 acres. Masia, is the first

  David Turner Compass Greater NY, LLC

  94 Somerstown Rd, Ossining, NY 10562
• 

  $703,000

  Sold Jun 29, 2026

  56 Hudson Watch Dr, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,629 Sq Ft
  • Built 1987

  Last Sold Summary

  • 8% Above List Price
  • $432/SF
  • 10 Days On Market

  Current Estimated Value $666,971

  Last Listing Agent Heather Bouza Compass Greater NY, LLC

  56 Hudson Watch Dr, Ossining, NY 10562
• 

  Est $672,467

  Not Listed For Sale

  30 Morningside Dr, Ossining, NY 10562

  • 3 Beds
  • 2.5 Baths
  • 2,616 Sq Ft
  • Built 1920

  30 Morningside Dr, Ossining, NY 10562

  Last Sold Summary

  • 19 Days On Market
• 

  

  /25

  $235,000

  Pending

  • 2 Beds
  • 1 Bath
  • 860 Sq Ft

  42 Charter Cir Unit 42, Ossining, NY 10562

  Welcome to 42 Charter Circle in Ossining, a home that offers space, comfort, and an incredibly convenient lifestyle. Life at High Meadow means having everything within easy reach. Commuting is simple with a 1.1-mile journey to the Scarborough Metro-North Station and a 46-minute commute to Grand Central Station. Daily errands are quick, and nearby shops, restaurants, and essentials make day-to-day

  Amanda Saraceno Keller Williams Realty Group

  42 Charter Cir Unit 42, Ossining, NY 10562
• 

  $535,000

  Sold Mar 26, 2026

  504 Kemeys Cove Unit 5-04, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2 Baths
  • 1,227 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Above List Price
  • $436/SF
  • 18 Days On Market

  Last Listing Agent Nicholas McMillan Century 21 Hire Realty

  504 Kemeys Cove Unit 5-04, Briarcliff Manor, NY 10510
• 

  Est $759,291

  Not Listed For Sale

  6 Morningside Dr, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,695 Sq Ft
  • Built 1950

  6 Morningside Dr, Ossining, NY 10562

  Last Sold Summary

  • 20 Days On Market
• 

  

  /40

  $1,975,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,080 Sq Ft

  159 Chappaqua Rd, Briarcliff Manor, NY 10510

  From the outside, 159/161 Chappaqua Road presents as a charming farmhouse—but it offers far more than its picturesque post-and-rail fence suggests. Set on 1.29 acres, with a newly renovated guest house Cottage, this 19th-century compound seamlessly blends historic character with modern luxury, featuring a four-bedroom, 3.1-bath Colonial-style Main House.A bluestone walkway leads to the

  Marcene Hedayati Corcoran Legends Realty

  159 Chappaqua Rd, Briarcliff Manor, NY 10510
• 

  $679,000

  Sold Mar 30, 2026

  33 Ryder Rd, Ossining, NY 10562

  • 5 Beds
  • 2.5 Baths
  • 3,656 Sq Ft
  • Built 1826

  Last Sold Summary

  • 4% Below List Price
  • $186/SF
  • 82 Days On Market

  Current Estimated Value $714,484

  Last Listing Agent Justin Landon Howard Hanna Rand Realty

  33 Ryder Rd, Ossining, NY 10562
• 

  Est $882,767

  Not Listed For Sale

  18 Studio Hill Rd, Briarcliff Manor, NY 10510

  • 3 Beds
  • 3 Baths
  • 2,224 Sq Ft
  • Built 1964

  18 Studio Hill Rd, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 13 Days On Market
• 

  

  /48

  $650,000

  • 4 Beds
  • 2 Baths
  • 1,667 Sq Ft

  24 Fuller Rd, Ossining, NY 10562

  Beautiful 4-bedroom, 2 full bath home located on a quiet cul-de-sac in Ossining, offering a comfortable layout and inviting indoor-outdoor living. The main level features an open-concept design connecting the eat-in kitchen and living room, highlighted by modern stainless steel appliances, beautiful moldings, and expansive windows that fill the home with natural light, creating an ideal setting

  Joseph Lukic Compass Greater NY, LLC

  24 Fuller Rd, Ossining, NY 10562
• 

  $190,000

  Sold Aug 04, 2025

  117 S Highland Ave Unit 1L, Ossining, NY 10562

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

  Last Sold Summary

  • 3% Below List Price
  • $211/SF
  • 57 Days On Market

  Current Estimated Value $158,000

  Last Listing Agent Danielle Mango Houlihan Lawrence Inc.

  117 S Highland Ave Unit 1L, Ossining, NY 10562
• 

  Est $901,815

  Not Listed For Sale

  3 Haymont Terrace, Briarcliff Manor, NY 10510

  • 4 Beds
  • 2 Baths
  • 2,436 Sq Ft
  • Built 1960

  3 Haymont Terrace, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 83 Days On Market
• 

  

  /26

  $329,222

  $40K PRICE DROP Pending

  • 2 Beds
  • 1.5 Baths
  • 972 Sq Ft

  42 Campwoods Grounds, Ossining, NY 10562

  This beautifully updated home now features several new upgrades, including a fully reconstructed floor on the main level, professionally rebuilt for lasting stability and comfort. Step back in time and discover the charm of this turn-of-the-century cottage, nestled in the heart of the historic Campwoods Grounds Community. Enjoy the unique blend of community living and the privacy of a

  Mark Seiden Mark Seiden Real Estate Team

  42 Campwoods Grounds, Ossining, NY 10562
• 

  $119,000

  Sold Jun 02, 2026

  121 S Highland Ave Unit 5F, Ossining, NY 10562

  • 1 Bath
  • 650 Sq Ft
  • Built 1964

  Last Sold Summary

  • 8% Below List Price
  • $183/SF
  • 37 Days On Market

  Last Listing Agent Robert Pape Keller Williams NY Realty

  121 S Highland Ave Unit 5F, Ossining, NY 10562
• 

  Est $780,159

  Not Listed For Sale

  75B Morningside Dr, Ossining, NY 10562

  • 3 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1956

  75B Morningside Dr, Ossining, NY 10562

  Last Sold Summary

  • 21 Days On Market
• 

  

  /38

  $724,222

  • 2 Beds
  • 2.5 Baths
  • 1,899 Sq Ft

  86 Woods Brooke Terrace, Ossining, NY 10562

  Experience turnkey luxury in this beautifully renovated corner unit at The Woods, where every detail has been thoughtfully updated from top to bottom. The heart of the home is the custom high-end Bilotta kitchen, featuring a granite center island with seating, Bosch stainless steel appliances, induction cooktop, pantry, and under-cabinet lighting. The open-concept main level is ideal for both

  Mark Seiden Mark Seiden Real Estate Team

  86 Woods Brooke Terrace, Ossining, NY 10562

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