Chappaqua, NY Homes

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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
• 

  $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 $3,077,164

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  93 Haights Cross Rd, Chappaqua, NY 10514
• 

  Est $2,011,758

  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
• 

  

  

  /41

  $1,600,000

  Pending

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

  14 Crossways, Chappaqua, NY 10514

  Most “walk-to-town” homes ask you to compromise on space, privacy, or both. At 14 Crossways, you get all three. Set less than a mile from the Chappaqua station, it combines true walkability with more than 3,100 square feet of well-organized living space on a private, level half-acre. Carefully maintained and thoughtfully improved, it is also a house designed for entertaining. At its center, the

  Jonathan Cape Julia B Fee Sothebys Int. Rlty

  14 Crossways, 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 $730,660

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  380 Whippoorwill Rd, Chappaqua, NY 10514
• 

  Est $1,669,211

  Not Listed For Sale

  64 Cowdin Cir, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,911 Sq Ft
  • Built 1962

  64 Cowdin Cir, Chappaqua, NY 10514

  Last Sold Summary

  • 14 Days On Market
• 

  

  /49

  $2,475,000

  $124K PRICE DROP Pending

  • 4 Beds
  • 4.5 Baths
  • 6,640 Sq Ft

  17 Byram Meadows Rd, Chappaqua, NY 10514

  Beautifully appointed and meticulously maintained 4 bedroom, 4 1/2 bath Colonial set on a level acre at the end of a quiet cul-de-sac in prestigious Inglenook Farm in the coveted Byram Hills Schools. A grand and light-filled two-story entry welcomes you into this refined open layout home featuring 9-foot ceilings on 1st and 2nd levels, oak flooring, and custom moldings and trim throughout. Formal

  Cindy Glynn Compass Greater NY, LLC

  17 Byram Meadows Rd, 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 $1,084,340

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  326 Millwood Rd, Chappaqua, NY 10514
• 

  Est $2,470,629

  Not Listed For Sale

  76 Cowdin Ln, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,600 Sq Ft
  • Built 1962

  76 Cowdin Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 14 Days On Market
• 

  

  /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
• 

  $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 $2,699,597

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

  8 Turtleback Way, Chappaqua, NY 10514
• 

  Est $3,219,580

  Not Listed For Sale

  63 Cowdin Ln, Chappaqua, NY 10514

  • 4 Beds
  • 5.5 Baths
  • 7,764 Sq Ft
  • Built 2007

  63 Cowdin Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 11 Days On Market
• 

  

  /6

  $639,000

  • Land
  • 7,405 Sq Ft
  • $3,758,824 per Acre

  65 S Bedford Rd, Chappaqua, NY 10514

  A rare opportunity to build mixed use consisting of commercial/professional and multi-family with huge income potential.The 1st floor as commercial and the 2nd and 3rd floors residential apartments.An architect has drawn 4 concept plans ranging from commercial space and lobby with (4) 2-bedroom apartments to commercial space and lobby with (6) 1-bedroom apartments.One example:1st

  Theodore Weinstein REO Edge LLC

  65 S Bedford 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 $1,310,363

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  71 Commodore Rd, Chappaqua, NY 10514
• 

  Est $2,296,437

  Not Listed For Sale

  70 Cowdin Ln, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 5,309 Sq Ft
  • Built 1987

  70 Cowdin Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 97 Days On Market
• 

  

  /47

  $3,389,000

  • 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
• 

  $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 $1,933,333

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  2 Whippoorwill Close, Chappaqua, NY 10514
• 

  Est $1,571,266

  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
• 

  

  /29

  $1,499,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,002 Sq Ft

  95 Old Lyme Rd, Chappaqua, NY 10514

  Attractive contemporary home ideally located near town, offering over 3,000 square feet of light-filled living space with soaring ceilings and a wonderful open flow for today’s lifestyle. This 4-bedroom home features a spacious cook’s kitchen, three fireplaces, and generously scaled rooms designed for comfortable everyday living and easy entertaining. A flexible first-floor room plus full bath

  Amy Singer Houlihan Lawrence Inc.

  95 Old Lyme 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 $1,739,959

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514
• 

  Est $1,707,696

  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
• 

  

  /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
• 

  $1,775,000

  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 $1,894,662

  Last Listing Agent Debra Goldenberg Compass Greater NY, LLC

  3 Sunset Dr, Chappaqua, NY 10514
• 

  Est $2,780,990

  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
• 

  

  /36

  $1,299,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,444 Sq Ft

  816 Hardscrabble Rd, Chappaqua, NY 10514

  Just north of NYC, this move-in ready CHAPPAQUA home delivers effortless, elevated living—done RIGHT.3 min drive to Metro North station - 48 min ride to Grand Central Station * Set behind a long private driveway with an attached 2-car garage and expansive front yard, the property captures stunning sunset views, with golden hour pouring in the best way. Inside captures a calm, grounded palette

  Bianca Siani eXp Realty

  816 Hardscrabble Rd, Chappaqua, NY 10514
• 

  $1,679,000

  Sold Sep 18, 2025

  10 Carriage Ln Unit 85, Chappaqua, NY 10514

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

  Last Sold Summary

  • $514/SF
  • 137 Days On Market

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

  10 Carriage Ln Unit 85, Chappaqua, NY 10514
• 

  Est $1,537,264

  Not Listed For Sale

  416 Bedford Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 2,356 Sq Ft
  • Built 1952

  416 Bedford Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 17 Days On Market
• 

  

  /27

  $899,000

  Open Sat 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,586 Sq Ft

  2 Timberland Pass, Chappaqua, NY 10514

  Welcome to Apple Hill Farm, sitting on highly desirable, 37+ Wooded Acres. Where calm meets comfort. This corner Townhome, located in a cul-de-sac for added privacy, features a manicured lawn and a carefully curated garden. Experience modern elegance in this home, with high ceilings, lots of Windows and Skylights that bring abundant natural daylight and sunlight indoors. It has 3 Bedrooms and 2.5

  Nana Aboagye Dorothy Jensen Realty, Inc.

  2 Timberland Pass, Chappaqua, NY 10514
• 

  $1,402,970

  Sold Jun 23, 2025

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 2,945 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Above List Price
  • $476/SF
  • 142 Days On Market

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514
• 

  Est $2,594,096

  Not Listed For Sale

  31 Hemlock Hills, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 6,187 Sq Ft
  • Built 1989

  31 Hemlock Hills, Chappaqua, NY 10514

  Last Sold Summary

  • 21 Days On Market
• 

  

  /41

  $2,750,000

  Pending

  • 6 Beds
  • 3.5 Baths
  • 6,532 Sq Ft

  276 Quaker Rd, Chappaqua, NY 10514

  A truly rare Chappaqua mini-estate with pool and tennis, offering resort-style living just a short walk from the town and train. Privately perched atop a hill and approached by a sweeping stone-lined driveway, this property delivers an exceptional blend of privacy, presence, and convenience—moments from shops, dining, and Metro-North. The expansive grounds are designed for all-season enjoyment,

  Sari Shaw Compass Greater NY, LLC

  276 Quaker Rd, Chappaqua, NY 10514
• 

  $2,000,000

  Sold Apr 28, 2026

  40 Smith St, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,658 Sq Ft
  • Built 1927

  Last Sold Summary

  • 38% Above List Price
  • $752/SF
  • 7 Days On Market

  Current Estimated Value $1,641,354

  Last Listing Agent Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  40 Smith St, Chappaqua, NY 10514
• 

  Est $2,950,859

  Not Listed For Sale

  6 Hemlock Hollow, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 6,422 Sq Ft
  • Built 1998

  6 Hemlock Hollow, Chappaqua, NY 10514

  Last Sold Summary

  • 21 Days On Market
• 

  

  /42

  $1,399,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,443 Sq Ft

  6 Killington St, Chappaqua, NY 10514

  Dreamy modern ranch nestled on a private landscaped acre on a cul-de-sac in sought-after Whippoorwill. A flagstone walkway leads to a covered entry. The contemporary-styled front door with cross-reed glass panels and sidelight sets a refined first impression. Designed for effortless indoor/outdoor living, the rear-facing living room anchors the home with a wood-burning fireplace and two sets of

  Stacy Levey William Raveis-New York, LLC

  6 Killington St, Chappaqua, NY 10514
• 

  $1,125,000

  Sold Jul 21, 2025

  16 Garey Dr, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 1,888 Sq Ft
  • Built 1958

  Last Sold Summary

  • 25% Above List Price
  • $596/SF
  • 18 Days On Market

  Current Estimated Value $1,232,542

  Last Listing Agent Sherry Wiggs Houlihan Lawrence Inc.

  16 Garey Dr, Chappaqua, NY 10514
• 

  Est $3,399,549

  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

  • 29 Days On Market
• 

  

  /43

  $2,499,000

  • 3 Beds
  • 4 Baths
  • 6,115 Sq Ft

  33 Greenbriar Dr, Chappaqua, NY 10514

  Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods, this exceptional luxury Colonial blends timeless architecture, designer finishes, and an unmatched indoor-outdoor lifestyle within the award-winning Chappaqua school district. Privately positioned against acres of preserved land, this premier Westchester County property offers both tranquility and convenience,

  Wendy Nolan Houlihan Lawrence Inc.

  33 Greenbriar Dr, Chappaqua, NY 10514
• 

  $1,320,000

  Sold Dec 11, 2025

  41 Valley Ln, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 1972

  Last Sold Summary

  • 2% Above List Price
  • $649/SF
  • 10 Days On Market

  Current Estimated Value $1,369,703

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

  41 Valley Ln, Chappaqua, NY 10514
• 

  Est $2,674,972

  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

  • 164 Days On Market
• 

  

  /22

  $1,780,000

  Pending

  • 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

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