New Castle, NY Homes

• 

  $2,250,000

  Sold Aug 11, 2026

  22 Random Farms Cir, Chappaqua, NY 10514

  • 6 Beds
  • 5.5 Baths
  • 6,563 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Above List Price
  • $343/SF
  • 10 Days On Market

  Current Estimated Value $2,206,714

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  22 Random Farms Cir, Chappaqua, NY 10514
• 

  Est $2,710,900

  Not Listed For Sale

  11 Hammond Ridge Rd, Mount Kisco, NY 10549

  • 5 Beds
  • 4.5 Baths
  • 5,337 Sq Ft
  • Built 2006

  11 Hammond Ridge Rd, Mount Kisco, NY 10549

  Last Sold Summary

  • 10 Days On Market

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

  

  

  /24

  $725,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,307 Sq Ft

  65 Laurelton Rd, Mount Kisco, NY 10549

  CHARMING 1930'S. The perfect country house. Wood-Shingle Cape in the Heart of Stanwood. Beautifully updated four-bedroom home-circa 1937. Sun-filled rooms with Fir floors. Living Room with stone fireplace. Dining Area opening to renovated Kitchen with granite countertops and stainless appliances. Four Bedrooms with Two full Baths. Spacious rear deck for summer barbecues and outdoor entertaining.

  Claudia Atkinson Ginnel Real Estate

  65 Laurelton Rd, Mount Kisco, NY 10549
• 

  $1,391,022

  Sold Oct 23, 2025

  6 Algonquin Dr, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,776 Sq Ft
  • Built 1952

  Last Sold Summary

  • 16% Above List Price
  • $368/SF
  • 30 Days On Market

  Current Estimated Value $1,513,457

  Last Listing Agent Lindsay Rothman Compass Greater NY LLC

  6 Algonquin Dr, Chappaqua, NY 10514
• 

  Est $1,715,117

  Not Listed For Sale

  9 Killington St, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 2,625 Sq Ft
  • Built 1968

  9 Killington St, Chappaqua, NY 10514

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Natalia Wixom Compass Greater NY, LLC
• 

  

  /31

  $1,725,000

  • 4 Beds
  • 3.5 Baths
  • 3,581 Sq Ft

  53 W Orchard Rd, Chappaqua, NY 10514

  Welcome to an exceptional move-in ready home located in a highly desirable Chappaqua neighborhood known for its award-winning schools & sought-after lifestyle. Perfectly positioned in a quiet neighborhood, this stunning property offers privacy, space & luxury living at its finest. In addition, easy access to the North County Trail for any outdoor activities of your choice. Step inside & you'll

  Lori Meringolo Houlihan Lawrence Inc.

  53 W Orchard Rd, Chappaqua, NY 10514
• 

  $732,500

  Sold Dec 15, 2025

  30 Rambling Brook Rd, Chappaqua, NY 10514

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

  Last Sold Summary

  • 2% Below List Price
  • $589/SF
  • 24 Days On Market

  Current Estimated Value $752,223

  Last Listing Agent Amanda Acard Nestedge Realty

  30 Rambling Brook Rd, Chappaqua, NY 10514
• 

  Est $1,770,061

  Not Listed For Sale

  395 Bedford Rd, Chappaqua, NY 10514

  • 5 Beds
  • 3.5 Baths
  • 3,041 Sq Ft
  • Built 1955

  395 Bedford Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Catherine O'Connor Houlihan Lawrence Inc.
• 

  

  /27

  $1,590,000

  • 3 Beds
  • 3.5 Baths
  • 2,690 Sq Ft

  131 Douglas Rd, Chappaqua, NY 10514

  Tastefully Expanded and Renovated Colonial in the Heart of Chappaqua - New 4 bedroom Septic, 2024 Roof and Exceptional Indoor/Outdoor Living. Just moments to Chappaqua village, Metro North and highly regarded Chappaqua schools. A flexible first-floor guest/au pair suite with private bath, chefs kitchen with Wolf appliances, private primary suite, 2 fireplaces, expansive deck and mature grounds

  Toni DiMichelo Houlihan Lawrence Inc.

  131 Douglas Rd, Chappaqua, NY 10514
• 

  $1,731,000

  Sold Aug 06, 2026

  14 Crossways, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,138 Sq Ft
  • Built 1960

  Last Sold Summary

  • 8% Above List Price
  • $552/SF
  • 41 Days On Market

  Current Estimated Value $1,603,706

  Last Listing Agent Jonathan Cape Julia B Fee Sothebys Int. Rlty

  14 Crossways, Chappaqua, NY 10514
• 

  Est $1,582,048

  Not Listed For Sale

  133 Westwood Dr, Mount Kisco, NY 10549

  • 2 Beds
  • 3 Baths
  • 4,626 Sq Ft
  • Built 1997

  133 Westwood Dr, Mount Kisco, NY 10549

  Last Sold Summary

  • 107 Days On Market

  Last Listing Agent Jayne Begley William Raveis Real Estate
• 

  

  /49

  $1,800,000

  Open Sat 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 2,913 Sq Ft

  406 Bedford Rd, Chappaqua, NY 10514

  Welcome to this beautifully maintained almost 3000 sq ft 4 bedroom 4 bath Colonial set on a private, sun-filled one acre property framed by mature trees, a classic stone wall , and meticulously maintained landscaping and plantings.Elegance and craftsmanship are evident throughout with beautiful hardwood floors, generously sized bedrooms and a primary suite with private en-suite bath. At

  Donna Powers-Amori Howard Hanna Rand Realty

  406 Bedford Rd, Chappaqua, NY 10514
• 

  $1,780,000

  Sold Dec 22, 2025

  56 Annandale Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 4,543 Sq Ft
  • Built 2006

  Last Sold Summary

  • 1% Below List Price
  • $392/SF
  • 16 Days On Market

  Current Estimated Value $1,921,171

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

  56 Annandale Rd, Chappaqua, NY 10514
• 

  Est $8,053,102

  Not Listed For Sale

  123 Westwood Dr, Mount Kisco, NY 10549

  • 8 Beds
  • 14 Baths
  • 9,952 Sq Ft
  • Built 2007

  123 Westwood Dr, Mount Kisco, NY 10549

  Last Sold Summary

  • 148 Days On Market

  Last Listing Agent Brian Milton Compass Greater NY, LLC
• 

  

  /30

  $809,000

  $20K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  73 S Bedford Rd, Chappaqua, NY 10514

  Welcome home to this well-maintained residence in the heart of vibrant Chappaqua! This 4 bedroom and 2.5 full bathroom house is located in the award-winning Chappaqua school district. Step inside to discover gleaming hardwood floors throughout, a cozy living room with a wood-burning fireplace, and a bright, charming dining room. The kitchen features ample cabinetry, granite countertops, and

  Thomas Hennerty Thomas S. Hennerty

  73 S Bedford Rd, Chappaqua, NY 10514
• 

  $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 $767,437

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

  20 Highview Rd, Ossining, NY 10562
• 

  Est $3,949,327

  Not Listed For Sale

  115 Westwood Dr, Mount Kisco, NY 10549

  • 5 Beds
  • 5.5 Baths
  • 8,406 Sq Ft
  • Built 2002

  115 Westwood Dr, Mount Kisco, NY 10549

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Angela Kessel Houlihan Lawrence Inc.
• 

  

  /30

  $749,000

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft

  27 Mill River Rd, Chappaqua, NY 10514

  You’ll be hard-pressed to find a turn-key home like this—especially at this price—in the Chappaqua School District, let alone Westchester County! Welcome to this charming 1850s Colonial, ideally situated in the heart of Chappaqua, just 0.3 miles on foot via a convenient sidewalk to Metro-North and close to all that the village has to offer. With an easy walk to the train and convenient access by

  Johanna Kline Houlihan Lawrence Inc.

  27 Mill River Rd, Chappaqua, NY 10514
• 

  $1,424,000

  Sold Jun 08, 2026

  146 Fieldstone Dr Unit 146, Mount Kisco, NY 10549

  • 2 Beds
  • 3.5 Baths
  • 3,428 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Above List Price
  • $415/SF
  • 6 Days On Market

  Current Estimated Value $1,426,988

  Last Listing Agent Amanda Goldberg William Raveis-New York, LLC

  146 Fieldstone Dr Unit 146, Mount Kisco, NY 10549
• 

  Est $1,432,748

  Not Listed For Sale

  39 Kitchel Rd, Mount Kisco, NY 10549

  • 3 Beds
  • 2.5 Baths
  • 2,059 Sq Ft
  • Built 1955

  39 Kitchel Rd, Mount Kisco, NY 10549

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent MaryAnn Bayer Compass Greater NY, LLC
• 

  

  /43

  $1,575,000

  $75K PRICE DROP Pending

  • 4 Beds
  • 4 Baths
  • 2,715 Sq Ft

  50 Ludlow Dr, Chappaqua, NY 10514

  Set on a sought-after cul-de-sac lined with charming classic homes, this 1938 Colonial masterfully blends period charm with today’s lifestyle needs. Set on a lovely private acre with flat lawns surrounded by towering trees yet nestled in a neighborhood setting, this 2,715 square foot center hall Colonial home offers 4 bedrooms, 2 full and 2 half baths. The heart of the home is the family room

  Sena Baron William Raveis-New York, LLC

  50 Ludlow Dr, Chappaqua, NY 10514
• 

  $1,795,000

  Sold Oct 07, 2025

  20 Little Pine Rd, Mount Kisco, NY 10549

  • 4 Beds
  • 3.5 Baths
  • 4,576 Sq Ft
  • Built 1994

  Last Sold Summary

  • $392/SF
  • 30 Days On Market

  Current Estimated Value $1,860,132

  Last Listing Agent George D'Ambrosio Ginnel Real Estate

  20 Little Pine Rd, Mount Kisco, NY 10549
• 

  Est $2,129,303

  Not Listed For Sale

  14 Tall Timber, Mount Kisco, NY 10549

  • 4 Beds
  • 3.5 Baths
  • 4,312 Sq Ft
  • Built 1962

  14 Tall Timber, Mount Kisco, NY 10549

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Danae Richards William Raveis-New York, LLC
• 

  

  /31

  $1,375,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,254 Sq Ft

  88 Brevoort Rd, Chappaqua, NY 10514

  Location, Location, Location and the yard you have dreamt of! Set on a gorgeous, level, private acre on a flat cul-de-sac street that leads to sidewalks to downtown Chappaqua, Grafflin Elementary, and Bell Middle School, and just minutes from Whole Foods, Lifetime Fitness, Greeley High School, and more. This well maintained 3-bedroom, 2-bath home, with only $21,452 in taxes, shows pride of

  Lori Hoffman-Chlapowski Compass Greater NY, LLC

  88 Brevoort Rd, Chappaqua, NY 10514
• 

  $1,180,000

  Sold Feb 13, 2026

  65 Red Oak Ln, Mount Kisco, NY 10549

  • 3 Beds
  • 2 Baths
  • 1,992 Sq Ft
  • Built 1976

  Last Sold Summary

  • 7% Above List Price
  • $592/SF
  • 23 Days On Market

  Current Estimated Value $1,171,389

  Last Listing Agent Klevis Tana Howard Hanna Rand Realty

  65 Red Oak Ln, Mount Kisco, NY 10549
• 

  Est $2,707,571

  Not Listed For Sale

  35 Ivy Hill Rd, Chappaqua, NY 10514

  • 5 Beds
  • 4.5 Baths
  • 4,004 Sq Ft
  • Built 1942

  35 Ivy Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 47 Days On Market

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

  

  /24

  $700,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  440 Saw Mill River Rd, Millwood, NY 10546

  Welcome to 440 Saw Mill River Road, a meticulously maintained Cape Cod style home located in the heart of Millwood, NY and within the nationally renowned Chappaqua Central School District with its highly regarded Horace Greeley High School, Seven Bridges Middle School, and Westorchard Elementary. Built in 1950 the house has been owned and cared for by the same family since 1958. They made an

  David Valdez Houlihan Lawrence Inc.

  440 Saw Mill River Rd, Millwood, NY 10546
• 

  $2,597,511

  Sold Dec 04, 2025

  482 Armonk Rd, Mount Kisco, NY 10549

  • 5 Beds
  • 4.5 Baths
  • 4,348 Sq Ft
  • Built 1936

  Last Sold Summary

  • 4% Above List Price
  • $597/SF
  • 121 Days On Market

  Current Estimated Value $2,702,448

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

  482 Armonk Rd, Mount Kisco, NY 10549
• 

  Est $2,279,905

  Not Listed For Sale

  19 Tall Timber, Mount Kisco, NY 10549

  • 4 Beds
  • 3.5 Baths
  • 4,427 Sq Ft
  • Built 1961

  19 Tall Timber, Mount Kisco, NY 10549

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  $1,630,000

  Sold Jun 15, 2026

  114 Old Lyme Rd, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • Built 1977

  Last Sold Summary

  • 25% Above List Price
  • $663/SF
  • 6 Days On Market

  Current Estimated Value $1,623,784

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  114 Old Lyme Rd, Chappaqua, NY 10514
• 

  Est $1,861,163

  Not Listed For Sale

  10 Tall Timber, Mount Kisco, NY 10549

  • 4 Beds
  • 2.5 Baths
  • 3,354 Sq Ft
  • Built 1960

  10 Tall Timber, Mount Kisco, NY 10549

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Lindsay Matthews Houlihan Lawrence Inc.
• 

  $1,100,000

  Sold Aug 17, 2026

  6 Maria Ln, Ossining, NY 10562

  • 4 Beds
  • 3 Baths
  • 3,012 Sq Ft
  • Built 1975

  Last Sold Summary

  • 16% Above List Price
  • $365/SF
  • 13 Days On Market

  Current Estimated Value $947,476

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  6 Maria Ln, Ossining, NY 10562
• 

  Est $2,802,316

  Not Listed For Sale

  17 Colony Row, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,680 Sq Ft
  • Built 1965

  17 Colony Row, Chappaqua, NY 10514

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  $1,375,000

  Sold Apr 20, 2026

  111 Seven Bridges Rd, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,069 Sq Ft
  • Built 1961

  Last Sold Summary

  • 15% Above List Price
  • $665/SF
  • 32 Days On Market

  Current Estimated Value $1,365,777

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

  111 Seven Bridges Rd, Chappaqua, NY 10514
• 

  Est $2,381,749

  Not Listed For Sale

  23 Taylor Rd, Mount Kisco, NY 10549

  • 4 Beds
  • 5 Baths
  • 4,416 Sq Ft
  • Built 1929

  23 Taylor Rd, Mount Kisco, NY 10549

  Last Sold Summary

  • 154 Days On Market

  Last Listing Agent Maureen Verre Houlihan Lawrence Inc.
• 

  $2,375,000

  Sold Jun 12, 2026

  24 North Way, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 3,960 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Above List Price
  • $600/SF
  • 7 Days On Market

  Current Estimated Value $2,384,793

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate

  24 North Way, Chappaqua, NY 10514
• 

  Est $1,784,796

  Not Listed For Sale

  21 Taylor Rd, Mount Kisco, NY 10549

  • 3 Beds
  • 4 Baths
  • 3,957 Sq Ft
  • Built 1965

  21 Taylor Rd, Mount Kisco, NY 10549

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Reza Zoroufie Siano & Company Ltd.
• 

  $2,551,201

  Sold May 15, 2026

  0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 4,500 Sq Ft
  • Built 2026

  Last Sold Summary

  • 29% Above List Price
  • $567/SF
  • 88 Days On Market

  Last Listing Agent Rachel Lacoste Houlihan Lawrence Inc.

  0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514
• 

  Est $1,576,281

  Not Listed For Sale

  3 Kitchel Rd, Mount Kisco, NY 10549

  • 4 Beds
  • 4 Baths
  • 3,072 Sq Ft
  • Built 1980

  3 Kitchel Rd, Mount Kisco, NY 10549

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  $1,600,000

  Sold Dec 12, 2025

  27 Deepwood Hill, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft
  • Built 1950

  Last Sold Summary

  • 14% Above List Price
  • $565/SF
  • 35 Days On Market

  Current Estimated Value $1,542,333

  Last Listing Agent Brendan Preston Houlihan Lawrence Inc.

  27 Deepwood Hill, Chappaqua, NY 10514

Showing Results 161 - 200, Page 5 of 18