New Castle, NY Homes

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  Not Listed For Sale

  1176 Hardscrabble Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 3,537 Sq Ft
  • Built 1956

  1176 Hardscrabble Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Amy Via Houlihan Lawrence Inc.
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  /7

  $1,658,995

  Pending

  • 2 Beds
  • 3.5 Baths
  • 3,353 Sq Ft

  11 Wallace Way Unit 18, Chappaqua, NY 10514

  To be Built! Spring 2025 move-in. 3485 square feet ! Still time to personalize interior finishes at our luxury Design Studio. Final building for sale at Chappaqua Crossing! A roaring fireplace will warm the entire home. A private rooftop terrace with included outdoor gas fireplace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this

  Andrea Martone Houlihan Lawrence Inc.

  11 Wallace Way Unit 18, Chappaqua, NY 10514
• 

  $706,499

  Sold Oct 30, 2025

  52 Red Oak Ln, Mount Kisco, NY 10549

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft
  • Built 1938

  Last Sold Summary

  • 12% Below List Price
  • $398/SF
  • 127 Days On Market

  Current Estimated Value $745,879

  Last Listing Agent Kile Boga-Ibric Houlihan Lawrence Inc.

  52 Red Oak Ln, Mount Kisco, NY 10549
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  Not Listed For Sale

  16 Maria Ln, Ossining, NY 10562

  • 4 Beds
  • 3.5 Baths
  • 3,427 Sq Ft
  • Built 1887

  16 Maria Ln, Ossining, NY 10562

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team
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  /28

  $1,100,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  1 Commodore Rd, Chappaqua, NY 10514

  Welcome to a charming storybook Cape in the award-winning Chappaqua school district. This 3-bedroom, 2-bathroom home is sited on a beautiful, level property and features a 2-car garage attached by breezeway. Freshly painted and move-in ready, this inviting home offers comfortable living in one of Westchester's most sought-after communities. Enjoy the convenience of being just minutes to downtown

  Wendy Nolan Houlihan Lawrence Inc.

  1 Commodore Rd, Chappaqua, NY 10514
• 

  $1,830,000

  Sold Aug 13, 2026

  734 King St, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 3,672 Sq Ft
  • Built 1925

  Last Sold Summary

  • 14% Above List Price
  • $498/SF
  • 7 Days On Market

  Current Estimated Value $1,667,363

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  734 King St, Chappaqua, NY 10514
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  Not Listed For Sale

  9 Barnes Rd, Ossining, NY 10562

  • 4 Beds
  • 4.5 Baths
  • 4,583 Sq Ft
  • Built 1797

  9 Barnes Rd, Ossining, NY 10562

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Sena Baron William Raveis-New York, LLC
• 

  

  /27

  $800,000

  • 3 Beds
  • 2.5 Baths
  • 3,990 Sq Ft

  81 Glendale Rd, Ossining, NY 10562

  A rare convergence of land, privacy and proximity, 81 Glendale Road consists of 14.36 breathtaking acres in the Teatown area of New Castle, surrounded by some of Westchester County's most treasured protected landscapes. Set back from one of the area's most scenic roads, and nearly hidden from view (even in winter), the 3,990-square-foot residence is in the midst of a remarkable landscape of

  David Valdez Houlihan Lawrence Inc.

  81 Glendale Rd, Ossining, NY 10562
• 

  $460,000

  Sold May 01, 2026

  356 N Greeley Ave Unit 28G, Chappaqua, NY 10514

  • 1 Bed
  • 1.5 Baths
  • 1,207 Sq Ft
  • Built 1988

  Last Sold Summary

  • 15% Below List Price
  • $381/SF
  • 162 Days On Market

  Current Estimated Value $480,125

  Last Listing Agent Alicja Bohmrich Houlihan Lawrence Inc.

  356 N Greeley Ave Unit 28G, Chappaqua, NY 10514
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  Not Listed For Sale

  504 Millwood Rd, Mount Kisco, NY 10549

  • 4 Beds
  • 2.5 Baths
  • 3,182 Sq Ft
  • Built 1910

  504 Millwood Rd, Mount Kisco, NY 10549

  Last Sold Summary

  • 116 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
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  /49

  $3,599,000

  Pending

  • 5 Beds
  • 6.5 Baths
  • 10,594 Sq Ft

  301 Whippoorwill Rd, Chappaqua, NY 10514

  Timeless elegance meets exceptional craftsmanship in this spectacular brick and stone estate, privately set behind gates on 4+ acres in one of Chappaqua's prestigious Whippoorwill neighborhoods. Designed by acclaimed architect Carol Kurth and masterfully built in 2003 by renowned builder Robert Torre, this extraordinary 5-bedroom, 6 full, 1 half bath residence offers over 10,000 square feet of

  Cindy Glynn Compass Greater NY, LLC

  301 Whippoorwill Rd, Chappaqua, NY 10514
• 

  $1,350,000

  Sold Jul 31, 2026

  10 North Ln, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 3,155 Sq Ft
  • Built 1950

  Last Sold Summary

  • 3% Below List Price
  • $428/SF
  • 40 Days On Market

  Current Estimated Value $1,382,544

  Last Listing Agent Annette Cicinelli Keller Williams Realty Partner

  10 North Ln, Chappaqua, NY 10514
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  Not Listed For Sale

  90 Shingle House Rd, Millwood, NY 10546

  • 4 Beds
  • 3 Baths
  • 2,318 Sq Ft
  • Built 1940

  90 Shingle House Rd, Millwood, NY 10546

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent MaryAnn Bayer Compass Greater NY, LLC
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  /10

  $1,995,000

  Coming Soon

  • 4 Beds
  • 4.5 Baths
  • 4,796 Sq Ft

  76 Random Farms Cir, Chappaqua, NY 10514

  Set in Chappaqua’s desirable Random Farms community with pool, tennis and sports court, this custom-built, sleek and sophisticated Contemporary offers a distinctive blend of architectural style, natural light, and comfortable living. An exceptional open floor plan features vaulted ceilings, skylights, custom windows, and a combination of wood and granite floors. The spacious eat-in chef's kitchen

  Cindy Glynn Compass Greater NY, LLC

  76 Random Farms Cir, Chappaqua, NY 10514
• 

  $1,655,800

  Sold Apr 21, 2026

  9 Whitlaw Ln, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,932 Sq Ft
  • Built 1969

  Last Sold Summary

  • 12% Above List Price
  • $565/SF
  • 10 Days On Market

  Current Estimated Value $1,612,237

  Last Listing Agent Sena Baron William Raveis-New York, LLC

  9 Whitlaw Ln, Chappaqua, NY 10514
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  Not Listed For Sale

  130 Pinesbridge Rd, Ossining, NY 10562

  • 4 Beds
  • 3 Baths
  • 2,644 Sq Ft
  • Built 1946

  130 Pinesbridge Rd, Ossining, NY 10562

  Last Sold Summary

  • 168 Days On Market

  Last Listing Agent Natalia Wixom Compass Greater NY, LLC
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  /49

  $2,137,500

  $113K PRICE DROP

  • 4 Beds
  • 6 Baths
  • 4,340 Sq Ft

  82 Shingle House Rd, Millwood, NY 10546

  A rare opportunity to create a forever home on nearly 7 private acres in the Chappaqua School District. Rich in history, character and natural beauty, 82 Shingle House Road is a distinctive Millwood estate for the buyer who values land, privacy and potential over cookie-cutter perfection.Originally dating to 1762, the property has evolved over time and offers a unique combination of

  Vesna Kanacki Century 21 Elite Realty

  82 Shingle House Rd, Millwood, NY 10546
• 

  $1,436,000

  Sold Dec 05, 2025

  20 Pamela Place, Millwood, NY 10546

  • 4 Beds
  • 2.5 Baths
  • 3,103 Sq Ft
  • Built 1971

  Last Sold Summary

  • 9% Above List Price
  • $463/SF
  • 14 Days On Market

  Current Estimated Value $1,524,844

  Last Listing Agent Helen Dorman Houlihan Lawrence Inc.

  20 Pamela Place, Millwood, NY 10546
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  Not Listed For Sale

  50 Spring Valley Rd, Ossining, NY 10562

  • 3 Beds
  • 5 Baths
  • 3,902 Sq Ft
  • Built 1897

  50 Spring Valley Rd, Ossining, NY 10562

  Last Sold Summary

  • 388 Days On Market

  Last Listing Agent Michael Clemente DeSimone Real Estate
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  /17

  $3,350,000

  New Construction Pending

  • 4 Beds
  • 7 Baths
  • 5,712 Sq Ft

  201 Bedford Rd, Chappaqua, NY 10514

  Exciting all new construction by highly regarded local builder, Tavo Development, along with noted architect Teo Siguenza, aiming for a Fall 2026 completion. This refined, 5,712 sq ft Colonial blends classic architecture with sophisticated modern living. The light-filled main level, with 10’ ceilings, offers a seamless open floorplan featuring a chef’s kitchen with island and service pantry,

  Brian Milton Compass Greater NY, LLC

  201 Bedford Rd, Chappaqua, NY 10514
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  $2,960,000

  Sold Dec 26, 2025

  93 Haights Cross Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 6,542 Sq Ft
  • Built 1979

  Last Sold Summary

  • 15% Below List Price
  • $452/SF
  • 102 Days On Market

  Current Estimated Value $3,142,458

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  93 Haights Cross Rd, Chappaqua, NY 10514
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  Not Listed For Sale

  49 Spring Valley Rd, Ossining, NY 10562

  • 5 Beds
  • 3 Baths
  • 2,754 Sq Ft
  • Built 1855

  49 Spring Valley Rd, Ossining, NY 10562

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Matthew Valvano Berkshire Hathaway HS NY Prop
• 

  /2

  $239,000

  $36K PRICE DROP Pending

  • Land
  • 2.02 Acres
  • $118,317 per Acre

  181 Somerstown Rd, Millwood, NY 10546

  2+ acres of Land in Chappaqua School District. Calling all Buyers that can't find what they're looking for in a single family home...Build Your own home just the way you like! Moments from Shopping, Highways and Schools. Over 150' of frontage. Needs Zoning, Planning, BOH approvals. Get started today. Additional Information: SoilType:Unknown,

  Andrea Martone Houlihan Lawrence Inc.

  181 Somerstown Rd, Millwood, NY 10546
• 

  $525,000

  Sold Oct 16, 2025

  380 Whippoorwill Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 880 Sq Ft
  • Built 1927

  Last Sold Summary

  • 16% Below List Price
  • $597/SF
  • 61 Days On Market

  Current Estimated Value $773,976

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  380 Whippoorwill Rd, Chappaqua, NY 10514
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  Not Listed For Sale

  85 Haights Cross Rd, Chappaqua, NY 10514

  • 7 Beds
  • 6 Baths
  • 6,814 Sq Ft
  • Built 1969

  85 Haights Cross Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Amy Via Houlihan Lawrence Inc.
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  /47

  $3,389,000

  Pending

  • 4 Beds
  • 6.5 Baths
  • 5,563 Sq Ft

  40 Algonquin Dr, Chappaqua, NY 10514

  Timeless elegance meets relaxed country chic at this extraordinary Chappaqua retreat. Ideally situated on one of Chappaqua's most coveted streets, this remarkable residence was originally built in 1910 and completely renovated and reimagined in 200l and then again in 2009 for modern living. Privately set amid beautifully landscaped grounds, 40 Algonquin blends classic country manor-style

  Kathryn Weinberger Compass Greater NY, LLC

  40 Algonquin Dr, Chappaqua, NY 10514
• 

  $1,500,000

  Sold Aug 28, 2026

  120 Spring Valley Rd, Ossining, NY 10562

  • 11 Beds
  • 9 Baths
  • 3,366 Sq Ft
  • Built 1930

  Last Sold Summary

  • 6% Below List Price
  • $446/SF
  • 36 Days On Market

  Last Listing Agent Alfred Bruno Berkshire Hathaway HS NY Prop

  120 Spring Valley Rd, Ossining, NY 10562
• 

  Not Listed For Sale

  219 Hamilton Rd, Chappaqua, NY 10514

  • 6 Beds
  • 4.5 Baths
  • 4,692 Sq Ft
  • Built 1929

  219 Hamilton Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Stacy Levey William Raveis-New York, LLC
• 

  

  /27

  $1,079,000

  $21K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft

  54 Allapartus Rd, Ossining, NY 10562

  Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home offers a rare balance of privacy, space, convenience, and flexibility. Positioned on a corner lot and set far back from the road, the property provides a quiet and secluded feel while still being conveniently located approximately 15 minutes from downtown Chappaqua, the Chappaqua Train Station, shopping,

  Derek Greene Greene Realty Group

  54 Allapartus Rd, Ossining, NY 10562
• 

  $799,000

  Sold Aug 05, 2026

  127 Stone Bridge Square Unit 127, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,244 Sq Ft
  • Built 1986

  Last Sold Summary

  • $642/SF
  • 11 Days On Market

  Current Estimated Value $799,865

  Last Listing Agent Victoria Miller Compass Greater NY, LLC

  127 Stone Bridge Square Unit 127, Chappaqua, NY 10514
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  Est $1,710,490

  Not Listed For Sale

  370 Sarles St, Mount Kisco, NY 10549

  • 4 Beds
  • 3.5 Baths
  • 2,973 Sq Ft
  • Built 1908

  370 Sarles St, Mount Kisco, NY 10549

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Jody Rosen Julia B Fee Sothebys Int. Rlty
• 

  

  /49

  $2,350,000

  Pending

  • 4 Beds
  • 5 Baths
  • 4,385 Sq Ft

  790 King St, Chappaqua, NY 10514

  A Rare Opportunity Where History Meets Modern Living.Built in 1750 and thoughtfully renovated in 2005. White clapboard, black shutters, cedar shake roof, and copper gutters set a timeless exterior, framed by professionally designed grounds.A wide entry hall opens to living and dining rooms bookended by floor-to-ceiling stone fireplaces. Hardwood floors and detailed millwork mark the

  Harriet Libov Houlihan Lawrence Inc.

  790 King St, Chappaqua, NY 10514
• 

  $1,484,000

  Sold Sep 02, 2026

  67 Tripp St, Mount Kisco, NY 10549

  • 4 Beds
  • 3.5 Baths
  • 3,585 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $414/SF
  • 44 Days On Market

  Current Estimated Value $1,606,775

  Last Listing Agent George D'Ambrosio Ginnel Real Estate

  67 Tripp St, Mount Kisco, NY 10549
• 

  Est $2,859,881

  Not Listed For Sale

  16 Kittle Rd, Chappaqua, NY 10514

  • 5 Beds
  • 5.5 Baths
  • 4,249 Sq Ft
  • Built 1936

  16 Kittle Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Heather Bouza Compass Greater NY, LLC
• 

  

  /36

  $1,359,000

  • 3 Beds
  • 2.5 Baths
  • 2,798 Sq Ft

  180 Somerstown Rd, Millwood, NY 10546

  Welcome to this spacious and private Millwood home, ideally located in the award-winning Chappaqua School District. This 3-bedroom, 2.5-bath home lives like a 4-bedroom (currently used as a dedicated home office/den). A charming woodland driveway leads to a light-filled home featuring hardwood floors, oversized windows, and beautiful decorative mouldings. The main level offers an eat-in kitchen

  Wendy Nolan Houlihan Lawrence Inc.

  180 Somerstown Rd, Millwood, NY 10546
• 

  $865,000

  Sold Aug 04, 2026

  55 Hoags Cross Rd, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 2,292 Sq Ft
  • Built 1964

  Last Sold Summary

  • 4% Below List Price
  • $377/SF
  • 57 Days On Market

  Current Estimated Value $861,048

  Last Listing Agent Maryanne Durr Coldwell Banker Realty

  55 Hoags Cross Rd, Ossining, NY 10562
• 

  Est $1,953,892

  Not Listed For Sale

  55 Cowdin Cir, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 4,045 Sq Ft
  • Built 1952

  55 Cowdin Cir, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Eric Stein RE/MAX Distinguished Hms.&Prop
• 

  

  /27

  $49,500,000

  • 8 Beds
  • 10 Baths
  • 26,079 Sq Ft

  Unlisted Address

  ONE OF NEW YORK'S MOST COVETED ESTATES.Enter a world where timeless elegance meets state-of-the-art luxury. Originally built in 1901 for renowned financier J. Borden Harriman, this legendary estate - historically known as Devonshire, and earlier as Uplands and once Mannices - stands as a rare example of Gilded Age grandeur, reimagined for modern living. Over its long history, the estate

  Brian Sheerin William Raveis-New York LLC

  Unlisted Address
• 

  $1,620,000

  Sold Jun 17, 2026

  25 Longview Ln, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,193 Sq Ft
  • Built 1979

  Last Sold Summary

  • 25% Above List Price
  • $507/SF
  • 12 Days On Market

  Current Estimated Value $1,467,231

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  25 Longview Ln, Chappaqua, NY 10514
• 

  Est $2,008,269

  Not Listed For Sale

  70 Cowdin Cir, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 3,689 Sq Ft
  • Built 1963

  70 Cowdin Cir, Chappaqua, NY 10514

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

Showing Results 81 - 120, Page 3 of 18