Chappaqua, NY Homes

• 

  Est $2,092,850

  Not Listed For Sale

  2 Cedar Ln, Chappaqua, NY 10514

  • 5 Beds
  • 3.5 Baths
  • 4,462 Sq Ft
  • Built 1963

  2 Cedar Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 35 Days On Market
• 

  

  

  /37

  $2,250,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,988 Sq Ft

  21 Hemlock Hills, Chappaqua, NY 10514

  Experience modern luxury at 21 Hemlock Hills, a stunning home set on 1.8 acres of meticulously landscaped grounds. This residence features 4 spacious bedrooms and 3.5 bathrooms, including a gorgeous, luxurious master bathroom that serves as a private retreat. The heart of the home is the Carol Kurth-designed Leicht kitchen, a masterpiece featured in a magazine, seamlessly flowing into the open

  Debra Goldenberg Compass Greater NY, LLC

  21 Hemlock Hills, Chappaqua, NY 10514
• 

  $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 $1,510,111

  Last Listing Agent Brendan Preston Houlihan Lawrence Inc.

  27 Deepwood Hill, Chappaqua, NY 10514
• 

  Est $1,378,165

  Not Listed For Sale

  1283 Hardscrabble Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 2,830 Sq Ft
  • Built 1820

  1283 Hardscrabble Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 94 Days On Market
• 

  

  

  /42

  $1,995,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 5,247 Sq Ft

  33 Aldridge Rd, Chappaqua, NY 10514

  REHOBETH. A New Castle Landmark and on the National Register of Historic Places. Horace Greeley’s original stone barn, circa 1857. The first stone and cement structure built in the states converted to a residence in 1892 by one of Greeley’s daughters. They commissioned architect Ralph Adams Cram to remodel it into their house, which they named Rehoboth. Dramatic and impressive spaces with high

  Benjamin Ginnel Ginnel Real Estate

  33 Aldridge Rd, Chappaqua, NY 10514
• 

  $875,000

  Sold Aug 06, 2025

  341 Millwood Rd, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,541 Sq Ft
  • Built 1964

  Last Sold Summary

  • 3% Below List Price
  • $344/SF
  • 32 Days On Market

  Current Estimated Value $1,348,498

  Last Listing Agent Jo Ann Reilly Julia B Fee Sothebys Int. Rlty

  341 Millwood Rd, Chappaqua, NY 10514
• 

  Est $2,502,772

  Not Listed For Sale

  650 Quaker Rd, Chappaqua, NY 10514

  • 5 Beds
  • 6 Baths
  • 6,349 Sq Ft
  • Built 2012

  650 Quaker Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 46 Days On Market
• 

  

  /36

  $2,750,000

  Pending

  • 6 Beds
  • 4.5 Baths
  • 5,004 Sq Ft

  7 Quaker Ln, Chappaqua, NY 10514

  Welcome to this timeless and stunning Colonial, sited on 1.3 beautifully landscaped, private acres. This gracious 4-Bedroom Colonial blends classic architectural details with modern amenities -- open renovated kitchen with large island w/seating, spa-like bathrooms, new windows, solar paneling, Sonos throughout, a 2-bedroom cottage over the garage for long term guests, and a stunning Shoreline

  Victoria Miller Compass Greater NY, LLC

  7 Quaker Ln, Chappaqua, NY 10514
• 

  $1,850,000

  Sold Jun 01, 2026

  21 Kitchawan Dr, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 3,956 Sq Ft
  • Built 1922

  Last Sold Summary

  • 16% Above List Price
  • $468/SF
  • 13 Days On Market

  Current Estimated Value $1,922,898

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC

  21 Kitchawan Dr, Chappaqua, NY 10514
• 

  Est $3,112,093

  Not Listed For Sale

  76 Valley Ln, Chappaqua, NY 10514

  • 5 Beds
  • 5.5 Baths
  • 6,177 Sq Ft
  • Built 1987

  76 Valley Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 158 Days On Market
• 

  

  /14

  $1,665,000

  $85K PRICE DROP

  • Land
  • 12.92 Acres
  • $128,870 per Acre

  767 King St, Chappaqua, NY 10514

  Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park,

  Sena Baron William Raveis-New York, LLC

  767 King St, Chappaqua, NY 10514
• 

  $1,250,000

  Sold Jun 20, 2025

  64 Stornowaye St, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 2,144 Sq Ft
  • Built 1973

  Last Sold Summary

  • 4% Above List Price
  • $583/SF
  • 11 Days On Market

  Current Estimated Value $1,350,669

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

  64 Stornowaye St, Chappaqua, NY 10514
• 

  Est $1,788,105

  Not Listed For Sale

  20 Suzanne Ln, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft
  • Built 1965

  20 Suzanne Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 8 Days On Market
• 

  

  /50

  $1,200,000

  $149K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 3,112 Sq Ft

  335 Roaring Brook Rd, Chappaqua, NY 10514

  "VICTORIAN SPLENDOR" - A unique opportunity to own an early Grand Victorian home on park-like property with 3 fireplaces, a pool and a barn.Designated a New Castle George Carpenter Historic Landmark dating back to 1780. As you enter the main entrance a flood of natural light welcome you. The two-story projection of the façade’s central section, rising to a peak at the roofline, along

  Alicja Bohmrich Houlihan Lawrence Inc.

  335 Roaring Brook Rd, Chappaqua, NY 10514
• 

  $1,850,000

  Sold Sep 02, 2025

  42 Cross Ridge Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 3,102 Sq Ft
  • Built 1959

  Last Sold Summary

  • 35% Above List Price
  • $596/SF
  • 7 Days On Market

  Current Estimated Value $1,888,100

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate

  42 Cross Ridge Rd, Chappaqua, NY 10514
• 

  Est $2,409,816

  Not Listed For Sale

  95 Valley Ln, Chappaqua, NY 10514

  • 5 Beds
  • 5 Baths
  • 5,570 Sq Ft
  • Built 1979

  95 Valley Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market
• 

  

  /35

  $2,200,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 5,012 Sq Ft

  15 Haights Cross Rd, Chappaqua, NY 10514

  A serene, light-filled retreat where modern design meets timeless comfort, this exceptional four bedroom four and one half bath contemporary residence offers an elevated lifestyle in one of Chappaqua’s most coveted settings. Set along a premier Chappaqua road on nearly three acres, the home is defined by its airy interiors, soaring ceilings, light hardwood floors throughout, and walls of windows

  Donna Gordon Julia B Fee Sothebys Int. Rlty

  15 Haights Cross Rd, Chappaqua, NY 10514
• 

  $1,290,000

  Sold May 22, 2026

  80 Roaring Brook Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 3,421 Sq Ft
  • Built 1954

  Last Sold Summary

  • $377/SF
  • 20 Days On Market

  Current Estimated Value $1,297,343

  Last Listing Agent Mark Okamoto Houlihan Lawrence Inc.

  80 Roaring Brook Rd, Chappaqua, NY 10514
• 

  Est $1,553,270

  Not Listed For Sale

  1266 Hardscrabble Rd, Chappaqua, NY 10514

  • 5 Beds
  • 4 Baths
  • 4,447 Sq Ft
  • Built 1956

  1266 Hardscrabble Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 18 Days On Market
• 

  

  /40

  $1,336,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,417 Sq Ft

  148 Devoe Rd, Chappaqua, NY 10514

  Classic Devoe Road colonial! A covered front portico welcomes you to this timeless traditional 3-bedroom, 2.5-bath colonial-style home. The spacious living room, anchored by a wood burning fireplace and lined with custom bookshelves enjoys radiant sunshine from the oversized true divided light picture window overlooking the front of the residence. The living room adjoins the formal dining room,

  Stacy Levey William Raveis-New York, LLC

  148 Devoe Rd, Chappaqua, NY 10514
• 

  $1,025,000

  Sold Aug 22, 2025

  100 Castle Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 2,590 Sq Ft
  • Built 1996

  Last Sold Summary

  • 9% Below List Price
  • $396/SF
  • 19 Days On Market

  Current Estimated Value $1,186,132

  Last Listing Agent Alicja Bohmrich Houlihan Lawrence Inc.

  100 Castle Rd, Chappaqua, NY 10514
• 

  Est $1,476,005

  Not Listed For Sale

  24 Hilltop Dr, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 3,186 Sq Ft
  • Built 1964

  24 Hilltop Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 27 Days On Market
• 

  

  /35

  $1,299,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,096 Sq Ft

  14 Garey Dr, Chappaqua, NY 10514

  Completely reimagined and move-in ready, this sun-filled 3-bedroom plus home office, 2.5-bath home sits on over one acre of rare, level property in one of Chappaqua’s most sought-after neighborhoods. Blending modern updates with timeless design, the home offers a bright, open flow ideal for today’s lifestyle, with expansive windows that flood every room with natural light. The main level

  Whitney Bagliebter Compass Greater NY, LLC

  14 Garey Dr, Chappaqua, NY 10514
• 

  $995,000

  Sold Jul 28, 2025

  2 Woodmill Rd, Chappaqua, NY 10514

  • 5 Beds
  • 3.5 Baths
  • 5,227 Sq Ft
  • Built 1900

  Last Sold Summary

  • 15% Below List Price
  • $190/SF
  • 55 Days On Market

  Current Estimated Value $1,125,599

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team

  2 Woodmill Rd, Chappaqua, NY 10514
• 

  Est $1,459,137

  Not Listed For Sale

  20 Hilltop Dr, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,762 Sq Ft
  • Built 1966

  20 Hilltop Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 7 Days On Market
• 

  

  /36

  $1,699,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,483 Sq Ft

  12 Suzanne Ln, Chappaqua, NY 10514

  Perfectly positioned at the end of a quiet cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath Colonial offers the ideal blend of space, comfort, and effortless living—set on expansive, level property designed for both everyday enjoyment and memorable entertaining. A gracious foyer welcomes you, seamlessly opening to the living and dining rooms and creating a natural flow for gatherings.

  Jennifer Harris Compass Greater NY, LLC

  12 Suzanne Ln, Chappaqua, NY 10514
• 

  $1,660,000

  Sold Oct 03, 2025

  43 Random Farms Cir, Chappaqua, NY 10514

  • 5 Beds
  • 4.5 Baths
  • 5,357 Sq Ft
  • Built 1993

  Last Sold Summary

  • 13% Below List Price
  • $310/SF
  • 25 Days On Market

  Current Estimated Value $1,826,068

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.

  43 Random Farms Cir, Chappaqua, NY 10514
• 

  Est $1,392,054

  Not Listed For Sale

  48 Hilltop Dr, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 1,836 Sq Ft
  • Built 1969

  48 Hilltop Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 10 Days On Market
• 

  

  /33

  $1,599,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,496 Sq Ft

  34 Turner Dr, Chappaqua, NY 10514

  Welcome to 34 Turner Drive South -- an expanded and gracious 4-bedroom, 2-1/2 Bath, Farmhouse Colonial nestled at the end of a private drive. This special home is set on over an acre of flat, private property, surrounded by towering trees and tranquil woods. The interior features 3 fireplaces, custom millwork, hardwood floors and classic architectural details. The main level has a gracious Living

  Victoria Miller Compass Greater NY, LLC

  34 Turner Dr, Chappaqua, NY 10514
• 

  $999,999

  Sold Aug 18, 2025

  9 Campfire Rd, Chappaqua, NY 10514

  • 2 Beds
  • 1.5 Baths
  • 2,300 Sq Ft
  • Built 1930

  Last Sold Summary

  • 7% Below List Price
  • $435/SF
  • 21 Days On Market

  Current Estimated Value $1,120,375

  Last Listing Agent Therese Herrero Coldwell Banker Realty

  9 Campfire Rd, Chappaqua, NY 10514
• 

  Est $2,486,254

  Not Listed For Sale

  66 Hilltop Dr, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 5,395 Sq Ft
  • Built 1966

  66 Hilltop Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 7 Days On Market
• 

  

  /30

  $829,000

  • 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

  73 S Bedford Rd, Chappaqua, NY 10514
• 

  $1,300,033

  Sold Mar 27, 2026

  29 Meadow Ln, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,445 Sq Ft
  • Built 1960

  Last Sold Summary

  • 18% Above List Price
  • $532/SF
  • 10 Days On Market

  Current Estimated Value $1,272,972

  Last Listing Agent Lauren Zaccaria Houlihan Lawrence Inc.

  29 Meadow Ln, Chappaqua, NY 10514
• 

  Est $1,727,431

  Not Listed For Sale

  2 West Way, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 2,369 Sq Ft
  • Built 1949

  2 West Way, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market
• 

  

  /33

  $895,000

  $4K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  249 Mill River Rd, Chappaqua, NY 10514

  NOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed

  Harry Donofrio Town and Village Real Estate

  249 Mill River Rd, Chappaqua, NY 10514
• 

  $1,750,000

  Sold Jun 15, 2026

  4 Wright Dr, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,712 Sq Ft
  • Built 2023

  Last Sold Summary

  • $645/SF
  • 22 Days On Market

  Current Estimated Value $1,730,028

  Last Listing Agent Karin Kimtis Compass Greater NY, LLC

  4 Wright Dr, Chappaqua, NY 10514
• 

  Est $2,393,412

  Not Listed For Sale

  1 Green Ln, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 6,444 Sq Ft
  • Built 1987

  1 Green Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 15 Days On Market
• 

  

  /24

  $685,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,299 Sq Ft

  80 Bischoff Ave, Chappaqua, NY 10514

  Experience the best of convenient living in this stylishly updated 3-bedroom home, perfectly situated in a walk-to-all neighborhood near the train, schools, shopping, and library. This meticulously maintained property boasts significant modern upgrades, including double pane windows, Hardiplank siding, and a spacious Trex deck overlooking a private, flat, grassy backyard. Inside, enjoy hardwood

  Jeremy Zucker Keller Williams NY Realty

  80 Bischoff Ave, Chappaqua, NY 10514
• 

  $2,250,000

  Sold Mar 04, 2026

  19 Stony Hollow, Chappaqua, NY 10514

  • 3 Beds
  • 4.5 Baths
  • 3,880 Sq Ft
  • Built 1994

  Last Sold Summary

  • 13% Above List Price
  • $580/SF
  • 14 Days On Market

  Current Estimated Value $2,239,549

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

  19 Stony Hollow, Chappaqua, NY 10514
• 

  Est $1,880,810

  Not Listed For Sale

  55 Shadow Brook Pkwy, Chappaqua, NY 10514

  • 5 Beds
  • 3 Baths
  • 3,291 Sq Ft
  • Built 1964

  55 Shadow Brook Pkwy, Chappaqua, NY 10514

  Last Sold Summary

  • 49 Days On Market

Showing Results 161 - 200, Page 5 of 18