Chappaqua, NY Homes

• 

  

  

  /43

  $1,495,000

  Pending

  • 4 Beds
  • 4 Baths
  • 2,953 Sq Ft

  105 Cross Ridge Rd, Chappaqua, NY 10514

  Beautifully updated split ranch set on 1.02 park-like acres in a sought-after Chappaqua location near school, train and walkable to village center train and shops. The heart of this home is a spectacular high-end renovated eat-in kitchen featuring white cabinetry, Wolf, Miele, and Sub-Zero appliances, honed marble and granite counters, a center island with pendant lighting, a peninsula with

  Sena Baron William Raveis-New York, LLC

  105 Cross Ridge Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

  26 Dewitt Dr Unit 75, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 3,335 Sq Ft
  • Built 2024

  26 Dewitt Dr Unit 75, Chappaqua, NY 10514

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.
• 

  

  

  /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
• 

  $1,350,000

  Sold Apr 10, 2026

  200 S Bedford Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 2,364 Sq Ft
  • Built 1955

  Last Sold Summary

  • 17% Above List Price
  • $571/SF
  • 14 Days On Market

  Current Estimated Value $1,342,268

  Last Listing Agent Annette Cicinelli Keller Williams Realty Partner

  200 S Bedford Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

  45 Lila Ln Unit 62, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,101 Sq Ft
  • Built 2023

  45 Lila Ln Unit 62, Chappaqua, NY 10514

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.
• 

  

  /49

  $3,599,000

  Pending

  • 5 Beds
  • 6.5 Baths
  • 10,594 Sq Ft

  301 Whippoorwill Rd, Chappaqua, NY 10514

  Timeless elegance meets exceptional craftsmanship in this spectacular brick and stone estate, privately set behind gates on 4+ acres in one of Chappaqua's prestigious Whippoorwill neighborhoods. Designed by acclaimed architect Carol Kurth and masterfully built in 2003 by renowned builder Robert Torre, this extraordinary 5-bedroom, 6 full, 1 half bath residence offers over 10,000 square feet of

  Cindy Glynn Compass Greater NY, LLC

  301 Whippoorwill Rd, Chappaqua, NY 10514
• 

  $1,175,000

  Sold Jul 16, 2026

  3 Elm St, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 2,108 Sq Ft
  • Built 1905

  Last Sold Summary

  • 7% Above List Price
  • $557/SF
  • 16 Days On Market

  Current Estimated Value $1,103,421

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

  3 Elm St, Chappaqua, NY 10514
• 

  Not Listed For Sale

  41 Lila Ln Unit 60, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,101 Sq Ft
  • Built 2023

  41 Lila Ln Unit 60, Chappaqua, NY 10514

  Last Sold Summary

  • 117 Days On Market

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.
• 

  

  /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
• 

  $699,000

  Sold Jun 04, 2026

  150 N Bedford Rd Unit 6D, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,483 Sq Ft
  • Built 1984

  Last Sold Summary

  • $471/SF
  • 17 Days On Market

  Current Estimated Value $682,907

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  150 N Bedford Rd Unit 6D, Chappaqua, NY 10514
• 

  Not Listed For Sale

  39 Lila Ln Unit 59, Chappaqua, NY 10514

  • 2 Beds
  • 4 Baths
  • 3,101 Sq Ft
  • Built 2023

  39 Lila Ln Unit 59, Chappaqua, NY 10514

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Debbe Yarosh Toll Brothers Real Estate Inc.
• 

  

  /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
• 

  $1,275,000

  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 $1,368,808

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

  26 Mayberry Rd, Chappaqua, NY 10514
• 

  Est $2,005,906

  Not Listed For Sale

  2 Point Place, Chappaqua, NY 10514

  • 4 Beds
  • 5 Baths
  • 4,745 Sq Ft
  • Built 2017

  2 Point Place, Chappaqua, NY 10514

  Last Sold Summary

  • 116 Days On Market

  Last Listing Agent Hayes Hopple Julia B Fee Sothebys Int. Rlty
• 

  

  /47

  $3,389,000

  Pending

  • 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
• 

  $2,300,000

  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 $2,412,333

  Last Listing Agent Nancy Strong Douglas Elliman Real Estate

  3 Boulder Trail, Chappaqua, NY 10514
• 

  Est $1,856,673

  Not Listed For Sale

  20 Lawrence Frm Crswy, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 4,085 Sq Ft
  • Built 1978

  20 Lawrence Frm Crswy, Chappaqua, NY 10514

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  

  /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
• 

  $1,600,000

  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 $1,684,746

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  106 Random Farms Dr, Chappaqua, NY 10514
• 

  Not Listed For Sale

  35 Lila Ln Unit 57, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,386 Sq Ft
  • Built 2023

  35 Lila Ln Unit 57, Chappaqua, NY 10514

  Last Sold Summary

  • 115 Days On Market

  Last Listing Agent Debbe Yarosh Toll Brothers Real Estate Inc.
• 

  

  /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
• 

  $460,000

  Sold May 01, 2026

  356 N Greeley Ave Unit 28G, Chappaqua, NY 10514

  • 1 Bed
  • 1.5 Baths
  • 1,207 Sq Ft
  • Built 1988

  Last Sold Summary

  • 15% Below List Price
  • $381/SF
  • 162 Days On Market

  Current Estimated Value $480,125

  Last Listing Agent Alicja Bohmrich Houlihan Lawrence Inc.

  356 N Greeley Ave Unit 28G, Chappaqua, NY 10514
• 

  Not Listed For Sale

  33 Lila Ln Unit 56, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,101 Sq Ft
  • Built 2023

  33 Lila Ln Unit 56, Chappaqua, NY 10514

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Debbe Yarosh Toll Brothers Real Estate Inc.
• 

  

  /40

  $1,399,000

  Pending

  • 3 Beds
  • 4 Baths
  • 3,140 Sq Ft

  22 Garey Dr, Chappaqua, NY 10514

  Perched on a lushly landscaped acre and thoughtfully expanded, offering a comforting blend of function, space, and versatility for today’s lifestyle, whether working from home (the main-level office opens to a private deck, creating a delightful setting for morning coffee or an inspiring workday), entertaining (the spacious living room with fireplace adjoins the formal dining room with sliding

  Stacy Levey William Raveis-New York, LLC

  22 Garey Dr, Chappaqua, NY 10514
• 

  $1,350,000

  Sold Jul 31, 2026

  10 North Ln, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 3,155 Sq Ft
  • Built 1950

  Last Sold Summary

  • 3% Below List Price
  • $428/SF
  • 40 Days On Market

  Current Estimated Value $1,382,544

  Last Listing Agent Annette Cicinelli Keller Williams Realty Partner

  10 North Ln, Chappaqua, NY 10514
• 

  Not Listed For Sale

  1176 Hardscrabble Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 3,537 Sq Ft
  • Built 1956

  1176 Hardscrabble Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Amy Via Houlihan Lawrence Inc.
• 

  

  /27

  $879,000

  $20K PRICE DROP

  • 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
• 

  $1,655,800

  Sold Apr 21, 2026

  9 Whitlaw Ln, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,932 Sq Ft
  • Built 1969

  Last Sold Summary

  • 12% Above List Price
  • $565/SF
  • 10 Days On Market

  Current Estimated Value $1,612,237

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

  9 Whitlaw Ln, Chappaqua, NY 10514
• 

  Not Listed For Sale

  85 Haights Cross Rd, Chappaqua, NY 10514

  • 7 Beds
  • 6 Baths
  • 6,814 Sq Ft
  • Built 1969

  85 Haights Cross Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Amy Via Houlihan Lawrence Inc.
• 

  

  /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
• 

  $1,658,000

  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
• 

  Not Listed For Sale

  219 Hamilton Rd, Chappaqua, NY 10514

  • 6 Beds
  • 4.5 Baths
  • 4,692 Sq Ft
  • Built 1929

  219 Hamilton Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 11 Days On Market

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

  

  /33

  $1,999,999

  Pending

  • 5 Beds
  • 4.5 Baths
  • 4,058 Sq Ft

  765 King St, Chappaqua, NY 10514

  Perfectly situated on over three picturesque acres, this timeless 5 bedroom Federal Colonial effortlessly blends historical charm with modern convenience. Thoughtfully updated while maintaining its classic character, the home offers expansive living spaces, refined finishes, and an exceptional layout designed for today’s lifestyle. At the heart of the home is the stunning chef’s kitchen featuring

  Sari Shaw Compass Greater NY, LLC

  765 King St, Chappaqua, NY 10514
• 

  $752,000

  Sold Aug 19, 2025

  375 Quaker Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,084 Sq Ft
  • Built 1910

  Last Sold Summary

  • 16% Above List Price
  • $361/SF
  • 17 Days On Market

  Current Estimated Value $829,294

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

  375 Quaker Rd, Chappaqua, NY 10514
• 

  Est $2,859,881

  Not Listed For Sale

  16 Kittle Rd, Chappaqua, NY 10514

  • 5 Beds
  • 5.5 Baths
  • 4,249 Sq Ft
  • Built 1936

  16 Kittle Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Heather Bouza Compass Greater NY, LLC
• 

  

  /44

  $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
• 

  $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 $3,142,458

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  93 Haights Cross Rd, Chappaqua, NY 10514
• 

  Est $1,953,892

  Not Listed For Sale

  55 Cowdin Cir, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 4,045 Sq Ft
  • Built 1952

  55 Cowdin Cir, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Eric Stein RE/MAX Distinguished Hms.&Prop
• 

  

  /36

  $2,499,000

  $101K PRICE DROP 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
• 

  $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 $773,976

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  380 Whippoorwill Rd, Chappaqua, NY 10514

Showing Results 41 - 80, Page 2 of 18