Chappaqua, NY Homes

• 

  $1,589,000 Sold May 28, 2025

  395 Bedford Rd, Chappaqua, NY 10514

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

  Last Sold Summary

  • $523/SF
  • 26 Days On Market

  Current Estimated Value $1,630,129

  Last Listing Agent Catherine O'Connor Houlihan Lawrence Inc.

  395 Bedford Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

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

  1176 Hardscrabble Rd, Chappaqua, NY 10514

  1176 Hardscrabble Rd, Chappaqua, NY 10514
• 

  

  

  /48

  $1,999,999 Pending

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

  19 Stony Hollow, Chappaqua, NY 10514

  Living like a four-bedroom, this gracious and spacious three-bedroom plus bonus room modern Colonial shines from top to bottom from the meticulous maintenance and updates by the original owners. A welcoming, grand two-story entry introduces a large formal living room brightly illuminated by large front- and side-facing windows, recessed lighting and a wood-burning fireplace. French doors add

  Stacy Levey William Raveis-New York, LLC

  19 Stony Hollow, Chappaqua, NY 10514
• 

  $1,659,995 Sold Sep 10, 2025

  19 Wallace Way Unit 25, Chappaqua, NY 10514

  • 2 Beds
  • 4 Baths
  • 3,432 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $484/SF
  • 91 Days On Market

  Current Estimated Value $1,704,012

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

  19 Wallace Way Unit 25, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  9 McKesson Hill Rd, Chappaqua, NY 10514

  9 McKesson Hill Rd, Chappaqua, NY 10514
• 

  

  /22

  $1,780,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 3.5 Baths
  • 2,945 Sq Ft

  26 Wallace Way, Chappaqua, NY 10514

  Welcome to 26 Wallace Way — a standout residence in the coveted, sold-out Chappaqua Crossings Carriages community. Thoughtfully designed and impeccably finished, this first-floor primary bedroom home elevates townhouse living with refined interiors, dramatic architecture, and a setting that is both private and connected.The main level makes an immediate impression with a dramatic

  Craig DeCecchis Corcoran Legends Realty

  26 Wallace Way, Chappaqua, NY 10514
• 

  $3,400,000 Sold Sep 09, 2025

  5 Briarcliff Rd, Chappaqua, NY 10514

  • 4 Beds
  • 7 Baths
  • 7,305 Sq Ft
  • Built 2007

  Last Sold Summary

  • 8% Below List Price
  • $465/SF
  • 65 Days On Market

  Current Estimated Value $3,419,274

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  5 Briarcliff Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

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

  219 Hamilton Rd, Chappaqua, NY 10514

  219 Hamilton Rd, Chappaqua, NY 10514
• 

  

  /33

  $999,999

  • 3 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  105 Douglas Rd, Chappaqua, NY 10514

  .Welcome to this unique and charming carriage home nestled in the heart of Chappaqua. Legally 2BR but lives as 3 BR with permitted additions. Bright and sunny, set on a private 0.69-acre lot. This well-maintained residence blends timeless character with modern updates. Step inside to a welcoming entry foyer that leads to a spacious living room, complete with a cozy fireplace and French doors

  Al Posillico Keller Williams Realty Group

  105 Douglas Rd, Chappaqua, NY 10514
• 

  $1,050,000 Sold Feb 27, 2025

  106 Marcourt Dr, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 2,814 Sq Ft
  • Built 1961

  Last Sold Summary

  • 6% Above List Price
  • $373/SF
  • 35 Days On Market

  Current Estimated Value $1,182,362

  Last Listing Agent Madelyn Ricciardi Houlihan Lawrence Inc.

  106 Marcourt Dr, Chappaqua, NY 10514
• 

  Est $2,700,303 Not Listed For Sale

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

  16 Kittle Rd, Chappaqua, NY 10514

  16 Kittle Rd, Chappaqua, NY 10514
• 

  

  /22

  $669,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,479 Sq Ft

  10 Grove Mews, Chappaqua, NY 10514

  Move right in to this 2-bedroom + loft, 2.5-bathroom townhouse in the highly sought-after Chappaqua School District. Freshly painted throughout and updated with brand-new quartz countertops, new dishwasher and new kitchen flooring, this home offers immediate comfort with the flexibility to personalize. The dining area features sliding doors that open to a grassy green space, while the kitchen

  Karin Kimtis Compass Greater NY, LLC

  10 Grove Mews, Chappaqua, NY 10514
• 

  $820,000 Sold Aug 20, 2025

  149 King St Unit 15, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,925 Sq Ft
  • Built 1988

  Last Sold Summary

  • $426/SF
  • 15 Days On Market

  Last Listing Agent Janet Short Houlihan Lawrence Inc.

  149 King St Unit 15, Chappaqua, NY 10514
• 

  Est $1,873,085 Not Listed For Sale

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

  55 Cowdin Cir, Chappaqua, NY 10514

  55 Cowdin Cir, Chappaqua, NY 10514
• 

  

  /47

  $3,499,000 Pending

  • 4 Beds
  • 7 Baths
  • 7,708 Sq Ft

  5 Sutton Farm Dr, Chappaqua, NY 10514

  Nestled on over 5 private, professionally landscaped acres in the exclusive cul-de-sac of Sutton Farm within Chappaqua’s esteemed Whippoorwill area, this custom-designed and custom-built Shingle Style home is a rare and refined first opportunity. Completed in 2008 by a renowned builder and architect, the 4+ bedroom home (lives like a 5/6) has been meticulously detailed with luxurious, high-end

  Cindy Glynn Compass Greater NY, LLC

  5 Sutton Farm Dr, Chappaqua, NY 10514
• 

  $1,632,000 Sold Apr 21, 2025

  81 Cross Ridge Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 3,211 Sq Ft
  • Built 1963

  Last Sold Summary

  • 17% Above List Price
  • $508/SF
  • 14 Days On Market

  Current Estimated Value $1,691,876

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate

  81 Cross Ridge Rd, Chappaqua, NY 10514
• 

  Est $1,835,720 Not Listed For Sale

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

  70 Cowdin Cir, Chappaqua, NY 10514

  70 Cowdin Cir, Chappaqua, NY 10514
• 

  

  /36

  $2,499,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,482 Sq Ft

  34 Pebblebrook Way, Chappaqua, NY 10514

  The only triple mint move-in condition house in Chappaqua schools. Nestled within 1.65 acres in the sought-after Hardscrabble Lake development and Chappaqua school district, this rare find modern Center Hall Colonial home epitomizes luxury living. If you are searching for a masterpiece beautifully finished home that is turnkey inside and out, this is your home. This meticulously thought-out

  Natalia Wixom Compass Greater NY, LLC

  34 Pebblebrook Way, Chappaqua, NY 10514
• 

  $1,835,000 Sold Jun 30, 2025

  20 Bristol Place, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 4,082 Sq Ft
  • Built 1965

  Last Sold Summary

  • 23% Above List Price
  • $450/SF
  • 6 Days On Market

  Current Estimated Value $1,839,000

  Last Listing Agent Kori Sassower Compass Greater NY, LLC

  20 Bristol Place, Chappaqua, NY 10514
• 

  Est $2,590,530 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,600 Sq Ft

  76 Cowdin Ln, Chappaqua, NY 10514

  76 Cowdin Ln, Chappaqua, NY 10514
• 

  

  /48

  $1,995,000

  • 4 Beds
  • 3 Baths
  • 5,216 Sq Ft

  35 Neustadt Ln, Chappaqua, NY 10514

  Modern Masterpiece! Soaring contemporary on a serene cul-de-sac, this 4-bedroom, 5216 sq ft home is defined by walls of glass and dramatic, oversized rooms. Set amidst rock outcroppings on 2.39 wooded acres with towering pines and babbling brook, this one-of-a-kind home in the acclaimed Chappaqua School District is situated in one of the most desirable neighborhoods offering both privacy and

  Sena Baron William Raveis-New York, LLC

  35 Neustadt Ln, Chappaqua, NY 10514
• 

  $1,600,000 Sold Jul 22, 2025

  6 Dewitt Dr Unit 65, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,353 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $477/SF
  • 66 Days On Market

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

  6 Dewitt Dr Unit 65, Chappaqua, NY 10514
• 

  Est $3,165,391 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 7,764 Sq Ft

  63 Cowdin Ln, Chappaqua, NY 10514

  63 Cowdin Ln, Chappaqua, NY 10514
• 

  

  /21

  $649,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,292 Sq Ft

  221 N Greeley Ave, Chappaqua, NY 10514

  Fantastic opportunity just steps from downtown Chappaqua. Only a short three minute walk to the heart of town, this property sits on a generous lot with great outdoor space and endless potential. Currently used as a single family home, the Business Retail zoning allows for a variety of uses whether you are an investor, looking for a live work setup, or considering a residential conversion. An

  Robert Dellaero Julia B Fee Sothebys Int. Rlty

  221 N Greeley Ave, Chappaqua, NY 10514
• 

  $1,275,000 Sold Oct 03, 2025

  26 Mayberry Rd, Chappaqua, NY 10514

  • 5 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Above List Price
  • $398/SF
  • 85 Days On Market

  Current Estimated Value $1,272,920

  Last Listing Agent Edward Holmes William Raveis-New York, LLC

  26 Mayberry Rd, Chappaqua, NY 10514
• 

  Est $2,295,461 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 5,309 Sq Ft

  70 Cowdin Ln, Chappaqua, NY 10514

  70 Cowdin Ln, Chappaqua, NY 10514
• 

  

  /21

  $849,000

  • 3 Beds
  • 2.5 Baths
  • 1,569 Sq Ft

  23 Waters Edge Unit 23, Chappaqua, NY 10514

  Welcome to 23 Waters Edge, a delightful three-bedroom, two-and-a-half-bath home in the sought-after Old Farm Lake community in Chappaqua. This natural light-filled residence features an open floor plan with sliding doors that lead to a private patio—perfect for relaxed, easy living. Ideally located in the complex, this home enjoys privacy along with proximity to the community amenities. The open

  Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  23 Waters Edge Unit 23, Chappaqua, NY 10514
• 

  $2,300,000 Sold Oct 08, 2025

  3 Boulder Trail, Chappaqua, NY 10514

  • 5 Beds
  • 4.5 Baths
  • 5,183 Sq Ft
  • Built 2000

  Last Sold Summary

  • 18% Above List Price
  • $444/SF
  • 91 Days On Market

  Current Estimated Value $2,302,236

  Last Listing Agent Nancy Strong Douglas Elliman Real Estate

  3 Boulder Trail, Chappaqua, NY 10514
• 

  Est $1,630,950 Not Listed For Sale

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

  9 Killington St, Chappaqua, NY 10514

  9 Killington St, Chappaqua, NY 10514
• 

  

  /48

  $1,375,000 Pending

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

  341 Millwood Rd, Chappaqua, NY 10514

  Discover the perfect balance of modern design and peaceful living at 341 Millwood Road. Set on nearly 2 acres of wooded privacy within the Chappaqua School District, this completely renovated 4-bedroom, 2.5-bath Raised Ranch has been transformed from top to bottom. Every detail shines - from new flooring, doors, moldings, lighting, and baths to a stunning eat-in kitchen with GE Cafe

  Lauren Zaccaria Houlihan Lawrence Inc.

  341 Millwood Rd, Chappaqua, NY 10514
• 

  $1,570,856 Sold Jul 25, 2025

  16 Dewitt Dr Unit 70, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft
  • Built 2025

  Last Sold Summary

  • 11% Below List Price
  • $481/SF
  • 323 Days On Market

  Current Estimated Value $1,605,031

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

  16 Dewitt Dr Unit 70, Chappaqua, NY 10514
• 

  Est $2,575,663 Not Listed For Sale

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

  17 Colony Row, Chappaqua, NY 10514

  17 Colony Row, Chappaqua, NY 10514
• 

  

  /35

  $3,450,000

  • 6 Beds
  • 5.5 Baths
  • 8,200 Sq Ft

  20 Bessel Ln, Chappaqua, NY 10514

  Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides

  Tianying Xu Houlihan Lawrence Inc.

  20 Bessel Ln, Chappaqua, NY 10514
• 

  $1,920,000 Sold Apr 21, 2025

  22 Valley Ln, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 4,145 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Above List Price
  • $463/SF
  • 5 Days On Market

  Current Estimated Value $1,905,974

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  22 Valley Ln, Chappaqua, NY 10514
• 

  Est $1,140,847 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,887 Sq Ft

  2 Apple Tree Close, Chappaqua, NY 10514

  2 Apple Tree Close, Chappaqua, NY 10514
• 

  

  /21

  $1,099,000

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  10 Barnes Ln, Chappaqua, NY 10514

  Move right into this beautifully updated three bedroom, two bathroom ranch, perfectly situated within the award-winning Chappaqua school district. Thoughtfully renovated from top to bottom, this home offers modern comfort and timeless charm. The heart of the home is the stylish kitchen featuring classic oak cabinetry, sleek quartz countertops, and ample space for cooking and entertaining. Both

  Alexander Marks William Raveis-New York LLC

  10 Barnes Ln, Chappaqua, NY 10514
• 

  $1,600,000 Sold Aug 22, 2025

  106 Random Farms Dr, Chappaqua, NY 10514

  • 5 Beds
  • 3.5 Baths
  • 3,859 Sq Ft
  • Built 1920

  Last Sold Summary

  • $415/SF
  • 40 Days On Market

  Current Estimated Value $1,600,818

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  106 Random Farms Dr, Chappaqua, NY 10514
• 

  Est $1,392,074 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,356 Sq Ft

  416 Bedford Rd, Chappaqua, NY 10514

  416 Bedford Rd, Chappaqua, NY 10514
• 

  

  /21

  $2,850,000 Pending

  • 4 Beds
  • 7 Baths
  • 5,536 Sq Ft

  211 Bedford Rd, Chappaqua, NY 10514

  Exciting and new state-of-the-art expansion and renovation by highly recognized local developer, Tavo Development teaming with noted architect Teo Seguenza. Ready for occupancy in Spring 2026. Meticulous attention to detail, years of experience and master craftsmanship are combined in this new offering, encompassing 5,536 sq ft, 4 bedrooms, 5 full and 2 half baths, a finished walk-out lower level

  Brian Milton Compass Greater NY, LLC

  211 Bedford Rd, Chappaqua, NY 10514
• 

  $1,658,000 Sold Aug 25, 2025

  4 Carriage Ln Unit 82, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,614 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $459/SF
  • 47 Days On Market

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

  4 Carriage Ln Unit 82, Chappaqua, NY 10514

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