Chappaqua, NY Homes

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  /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
• 

  $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 $2,998,601

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  93 Haights Cross Rd, Chappaqua, NY 10514
• 

  Est $3,113,594 Not Listed For Sale

  3 Trails End, Chappaqua, NY 10514

  • 5 Beds
  • 5.5 Baths
  • 6,083 Sq Ft
  • Built 1994

  3 Trails End, Chappaqua, NY 10514

  Last Sold Summary

  • 9% Above List Price
  • $469/SF
  • 29 Days On Market

  Last Sold Price $2,850,000

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC
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  /27

  $778,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  158 Millwood Rd, Chappaqua, NY 10514

  This classic center hall Colonial sits across the street, just steps from Gedney Park - one of the area’s most beloved parks, offering direct access to trails, fields, a playground, a sledding hill, a fishing pond, and year-round recreation. Inside, enjoy a sunlit living room with a wood-burning fireplace, French doors to a 3-season porch with new vinyl flooring, and refinished wood floors

  Edward Holmes William Raveis-New York, LLC

  158 Millwood Rd, Chappaqua, NY 10514
• 

  $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 $751,388

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  380 Whippoorwill Rd, Chappaqua, NY 10514
• 

  Est $2,772,583 Not Listed For Sale

  6 Trails End, Chappaqua, NY 10514

  • 5 Beds
  • 7 Baths
  • 7,624 Sq Ft
  • Built 1994

  6 Trails End, Chappaqua, NY 10514

  Last Sold Summary

  • 12% Above List Price
  • $325/SF
  • 164 Days On Market

  Last Sold Price $2,480,000

  Last Listing Agent Yaxing Zhang Houlihan Lawrence Inc.
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  /48

  $4,500,000

  • 5 Beds
  • 7 Baths
  • 7,608 Sq Ft

  150 Old Farm Rd N, Chappaqua, NY 10514

  1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original

  Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  150 Old Farm Rd N, Chappaqua, NY 10514
• 

  $745,000 Sold Mar 25, 2025

  105 Rambling Brook Rd, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,296 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Below List Price
  • $575/SF
  • 63 Days On Market

  Current Estimated Value $773,990

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  105 Rambling Brook Rd, Chappaqua, NY 10514
• 

  Est $2,858,970 Not Listed For Sale

  6 Paula Place, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 5,272 Sq Ft
  • Built 2005

  6 Paula Place, Chappaqua, NY 10514

  Last Sold Summary

  • 209% Above List Price
  • $175/SF
  • 85 Days On Market

  Last Sold Price $925,000

  Last Listing Agent Joe Hasselt Joe Hasselt Real Estate
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  /37

  $1,099,000

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

  2 Apple Tree Close, Chappaqua, NY 10514

  Nestled on a quiet cul-de-sac, 2 Apple Tree Close is a rare 1930s Colonial that beautifully honors its architectural heritage while offering the comforts of contemporary living. Located within the award-winning Chappaqua Central School District, this 3-bedroom, 1.5-bath residence perfectly preserves both authenticity and timeless appeal. Behind the original front door, a welcoming entry and

  Rachel Lacoste Houlihan Lawrence Inc.

  2 Apple Tree Close, Chappaqua, NY 10514
• 

  $2,875,000 Sold Mar 21, 2025

  76 Valley Ln, Chappaqua, NY 10514

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

  Last Sold Summary

  • 4% Above List Price
  • $465/SF
  • 158 Days On Market

  Current Estimated Value $2,874,800

  Last Listing Agent Harriet Libov Houlihan Lawrence Inc.

  76 Valley Ln, Chappaqua, NY 10514
• 

  Est $833,821 Not Listed For Sale

  15 Paula Place, Chappaqua, NY 10514

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1952

  15 Paula Place, Chappaqua, NY 10514

  Last Sold Summary

  • 18% Above List Price
  • $608/SF
  • 32 Days On Market

  Last Sold Price $705,000

  Last Listing Agent Lauren Zaccaria Houlihan Lawrence Inc.
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  /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
• 

  $999,000 Sold Aug 18, 2025

  326 Millwood Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 2,313 Sq Ft
  • Built 1924

  Last Sold Summary

  • $432/SF
  • 3 Days On Market

  Current Estimated Value $1,078,695

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  326 Millwood Rd, Chappaqua, NY 10514
• 

  Est $2,212,556 Not Listed For Sale

  345 Roaring Brook Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 5,668 Sq Ft
  • Built 1965

  345 Roaring Brook Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 15% Above List Price
  • $340/SF
  • 24 Days On Market

  Last Sold Price $1,925,000

  Last Listing Agent Sena Baron William Raveis-New York, LLC
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  /27

  $799,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  5 Grove Mews, Chappaqua, NY 10514

  All the space and privacy of a single-family home with the ease of condo living! One of the few completely stand-alone and private townhouses in Apple Hill Farm, this spacious 2-bedroom, 2.5-bath home offers a rare blend of comfort, style, and convenience. Enjoy the serene setting from a large wrap-around wood deck overlooking lush, wooded views—perfect for morning coffee or evening entertaining.

  Karin Kimtis Compass Greater NY, LLC

  5 Grove Mews, Chappaqua, NY 10514
• 

  $2,635,000 Sold Aug 25, 2025

  8 Turtleback Way, Chappaqua, NY 10514

  • 5 Beds
  • 4.5 Baths
  • 6,649 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Above List Price
  • $396/SF
  • 10 Days On Market

  Current Estimated Value $2,580,925

  Last Listing Agent Michele Iasich-Pagnotta Houlihan & O'Malley R. E. Serv

  8 Turtleback Way, Chappaqua, NY 10514
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  Est $2,342,996 Not Listed For Sale

  15 Kerry Ln, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 5,534 Sq Ft
  • Built 1935

  15 Kerry Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 17% Above List Price
  • $361/SF
  • 128 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Janine Marino Houlihan Lawrence Inc.
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  /44

  $3,400,000

  • 4 Beds
  • 5 Baths
  • 4,236 Sq Ft

  12 Haights Cross Rd, Chappaqua, NY 10514

  Experience the art of living well in this extraordinary private retreat overlooking Heaptaugua Lake. Set on just under five acres, the property offers total serenity while remaining just minutes from Chappaqua’s quaint downtown, restaurants, Metro-North, and shopping. Enter through the gates and follow the sweeping driveway as it curves past the pool house and pool, passing a sweeping lawn before

  Amy Via Houlihan Lawrence Inc.

  12 Haights Cross Rd, Chappaqua, NY 10514
• 

  $1,290,000 Sold Jan 21, 2026

  71 Commodore Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft
  • Built 1955

  Last Sold Summary

  • 11% Below List Price
  • $659/SF
  • 37 Days On Market

  Current Estimated Value $1,349,817

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  71 Commodore Rd, Chappaqua, NY 10514
• 

  Est $1,991,768 Not Listed For Sale

  28 McKesson Hill Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,541 Sq Ft
  • Built 1967

  28 McKesson Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 4% Above List Price
  • $539/SF
  • 12 Days On Market

  Last Sold Price $1,909,000

  Last Listing Agent Amanda Acard Nestedge Realty
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  /21

  $849,000 Pending

  • 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
• 

  $1,450,000 Sold May 22, 2025

  2 South Place, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,233 Sq Ft
  • Built 1936

  Last Sold Summary

  • 32% Above List Price
  • $649/SF
  • 9 Days On Market

  Current Estimated Value $1,439,914

  Last Listing Agent Toni DiMichelo Houlihan Lawrence Inc.

  2 South Place, Chappaqua, NY 10514
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  Est $1,879,595 Not Listed For Sale

  1 Round Hill Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 3,164 Sq Ft
  • Built 1963

  1 Round Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 7% Above List Price
  • $553/SF
  • 52 Days On Market

  Last Sold Price $1,750,000

  Last Listing Agent Elaine Wasserman Houlihan Lawrence Inc.
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  /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
• 

  $2,000,000 Sold Feb 09, 2026

  2 Whippoorwill Close, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,022 Sq Ft
  • Built 1980

  Last Sold Summary

  • 14% Above List Price
  • $662/SF
  • 4 Days On Market

  Current Estimated Value $1,741,668

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  2 Whippoorwill Close, Chappaqua, NY 10514
• 

  Est $2,045,598 Not Listed For Sale

  2 Sunset Dr, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,474 Sq Ft
  • Built 1986

  2 Sunset Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 16% Above List Price
  • $322/SF
  • 6 Days On Market

  Last Sold Price $1,760,000

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  

  /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
• 

  $2,300,000 Sold May 29, 2025

  25 Random Farms Dr, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 4,490 Sq Ft
  • Built 1992

  Last Sold Summary

  • 21% Above List Price
  • $512/SF
  • 6 Days On Market

  Current Estimated Value $2,281,742

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  25 Random Farms Dr, Chappaqua, NY 10514
• 

  Est $1,253,963 Not Listed For Sale

  610 Quaker Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 2,022 Sq Ft
  • Built 1954

  610 Quaker Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 109% Above List Price
  • $297/SF
  • 2 Days On Market

  Last Sold Price $600,000

  Last Listing Agent Igor Krasnoperov Rising Star Realty
• 

  

  /29

  $1,149,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,139 Sq Ft

  35 Hamilton Rd, Chappaqua, NY 10514

  .

  Caroline Shepherd Houlihan Lawrence Inc.

  35 Hamilton Rd, Chappaqua, NY 10514
• 

  $870,000 Sold Jun 04, 2025

  10 Leroy Place, Chappaqua, NY 10514

  • 2 Beds
  • 1.5 Baths
  • 1,492 Sq Ft
  • Built 1905

  Last Sold Summary

  • 35% Above List Price
  • $583/SF
  • 12 Days On Market

  Current Estimated Value $869,260

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

  10 Leroy Place, Chappaqua, NY 10514
• 

  Est $1,564,250 Not Listed For Sale

  15 Suzanne Ln, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,032 Sq Ft
  • Built 1965

  15 Suzanne Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 20% Above List Price
  • $431/SF
  • 14 Days On Market

  Last Sold Price $1,307,000

  Last Listing Agent MaryAnn Bayer Compass Greater NY, LLC
• 

  

  /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
• 

  $1,720,000 Sold Feb 04, 2026

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,244 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Above List Price
  • $530/SF
  • 25 Days On Market

  Current Estimated Value $1,674,078

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514
• 

  Est $1,281,362 Not Listed For Sale

  619 Quaker Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 1961

  619 Quaker Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 21% Above List Price
  • $564/SF
  • 33 Days On Market

  Last Sold Price $1,055,000

  Last Listing Agent Karin Kimtis Compass Greater NY, LLC
• 

  

  /5

  $1,599,995 Pending

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

  15 Wallace Way Unit 20, Chappaqua, NY 10514

  TO BE BUILT. Move-in Spring 2026. Spacious 3485 square feet ! Still time to personalize interior finishes by visiting our luxurious Design Studio. As you enter the Millwood Elite, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. A large center island in the kitchen overlooks the casual dining area. The great room is the perfect setting

  Andrea Martone Houlihan Lawrence Inc.

  15 Wallace Way Unit 20, Chappaqua, NY 10514
• 

  $1,775,000 Sold Jul 17, 2025

  3 Sunset Dr, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,587 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Above List Price
  • $495/SF
  • 7 Days On Market

  Current Estimated Value $1,795,259

  Last Listing Agent Debra Goldenberg Compass Greater NY, LLC

  3 Sunset Dr, Chappaqua, NY 10514
• 

  Est $1,045,125 Not Listed For Sale

  625 Quaker Rd, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 1,740 Sq Ft
  • Built 1950

  625 Quaker Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 39% Above List Price
  • $431/SF
  • 11 Days On Market

  Last Sold Price $750,000

  Last Listing Agent John Buckley William Raveis-New York LLC
• 

  

  /4

  $1,399,995 Pending

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

  13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514

  2 BR Primary on first floor home. Large Eat in kitchen with island, open to great room and dining room. Second floor office and wet bar makes entertaining easy on rooftop terrace with built-in kitchen BBQ. Lower level is finished with media room and full bath.

  Thomas Jacovino Toll Brothers Real Estate Inc.

  13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514

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