Chappaqua, NY Homes

• 

  

  

  /32

  $1,550,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,029 Sq Ft

  636 Quaker Rd, Chappaqua, NY 10514

  Move right into this sun-drenched, turnkey four-bedroom, four-bath home by Tom O’Brien Architecture, where classic design meets easy, comfortable living. Enter through cedar gates to a welcoming front portico with double columns and a barrel roof, setting the stage for what’s inside. The interior is bright and inviting, with newly refinished floors, custom millwork, recessed lighting, and

  

  Deena Bouchier

  Compass Greater NY, LLC

  (914) 350-6847

  636 Quaker Rd, Chappaqua, NY 10514
• Explore Chappaqua

• 

  

  

  /25

  $3,595 - $3,995 per month

  Chappaqua Crossing Apartments

  1 - 2 Beds

  480 Bedford Rd, Chappaqua, NY 10514

  Wilder Balter Partners, Inc., Hudson valley's premier developer of luxury homes has written a new chapter for the iconic reader's digest building. The four-story structure has undergone an unprecedented renovation, and the finished product embraces the nostalgia of the old media empire's headquarters with the extravagance of contemporary housing. Chappaqua Crossing Apts is now open! Please call

  480 Bedford Rd, Chappaqua, NY 10514
• 

  $1,313,550 Sold Apr 07, 2025

  50 North Place, Chappaqua, NY 10514

  • 5 Beds
  • 4 Baths
  • 5,590 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $235/SF
  • 15 Days On Market

  Current Estimated Value $1,676,766

  Last Listing Agent Christopher Rose REALHome Services & Solutions

  50 North Place, Chappaqua, NY 10514
• 

  Est $1,264,333 Not Listed For Sale

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 1,995 Sq Ft
  • Built 1960

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 3% Below List Price
  • $652/SF
  • 11 Days On Market

  Last Sold Price $1,300,000

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate
• 

  

  

  /39

  $1,599,999 Coming Soon

  • 4 Beds
  • 3 Baths
  • 3,672 Sq Ft

  734 King St, Chappaqua, NY 10514

  Thoughtfully reimagined farmhouse with barn, this distinctive 4-bedroom, 3-bath home blends historic charm with striking modern design. Set on close to 2 private acres surrounded by mature trees, the property offers exceptional privacy and a peaceful natural setting. Inside, soaring ceilings, oversized windows, and multiple skylights flood the home with natural light. The open-concept living

  Sari Shaw Compass Greater NY, LLC

  734 King St, Chappaqua, NY 10514
• 

  

  /20

  $5,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,569 Sq Ft
  • Townhouse for Rent

  118 Stone Bridge Square Unit 118, Chappaqua, NY 10514

  Three bedroom freshly painted unit in cul-de-sac location of Old Farm Lake. New refrigerator and new dishwasher in Eat-in-Kitchen with access to deck. Living Room/Dining Area with skylight and fireplace. Second level offers a primarty bedroom with walk-in closet and main bath. Two additional bedrooms and hall bath complete the second level. Complex offers pool, party room, tennis & clubhouse.

  Holly Tsuei Houlihan Lawrence Inc.

  118 Stone Bridge Square Unit 118, Chappaqua, NY 10514
• 

  $1,600,000 Sold Feb 27, 2026

  36 Pond Hill Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 2,866 Sq Ft
  • Built 1952

  Last Sold Summary

  • 23% Above List Price
  • $558/SF
  • 11 Days On Market

  Current Estimated Value $1,376,429

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

  36 Pond Hill Rd, Chappaqua, NY 10514
• 

  Est $1,721,605 Not Listed For Sale

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,700 Sq Ft
  • Built 2014

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 15% Above List Price
  • $405/SF
  • 54 Days On Market

  Last Sold Price $1,499,000

  Last Listing Agent Mary Ann Tighe Houlihan Lawrence Inc.
• 

  

  /40

  $1,475,000 Pending

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

  9 Whitlaw Ln, Chappaqua, NY 10514

  Welcome home to this beautifully maintained, move-in ready classic Center Hall Colonial, perfectly tucked away on a peaceful cul-de-sac just moments from schools, shopping, and town conveniences. Enjoy direct on-street access to the North County Trailway — ideal for biking, walking, or running right from your neighborhood.Offering approximately 2,900+ square feet of comfortable living space,

  Sena Baron William Raveis-New York, LLC

  9 Whitlaw Ln, Chappaqua, NY 10514
• 

  

  /31

  $11,500 per month

  • 4 Beds
  • 3.5 Baths
  • 4,644 Sq Ft
  • House for Rent

  291 Roaring Brook Rd, Chappaqua, NY 10514

  Welcome to the Jonathan Tompkins House, a true New Castle landmark dating back to 1750 where history and modern living intertwine. Ideally situated in the heart of Chappaqua and located within the award-winning Chappaqua School District, this fully furnished rental weaves centuries of New Castle’s past into its walls. Original hand-hewn beams and stained glass evoke timeless old-world charm,

  Rachel Lacoste Houlihan Lawrence Inc.

  291 Roaring Brook Rd, Chappaqua, NY 10514
• 

  $2,825,000 Sold Dec 15, 2025

  70 Haights Cross Rd, Chappaqua, NY 10514

  • 5 Beds
  • 9 Baths
  • 8,775 Sq Ft
  • Built 2005

  Last Sold Summary

  • 10% Below List Price
  • $322/SF
  • 159 Days On Market

  Current Estimated Value $2,898,699

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  70 Haights Cross Rd, Chappaqua, NY 10514
• 

  Est $1,515,627 Not Listed For Sale

  265 Mill River Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 4,811 Sq Ft
  • Built 2010

  265 Mill River Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 28% Above List Price
  • $246/SF
  • 68 Days On Market

  Last Sold Price $1,185,000

  Last Listing Agent Sandra Cappucci Julia B Fee Sothebys Int. Rlty
• 

  

  /43

  $1,899,000

  • 2 Beds
  • 3.5 Baths
  • 3,574 Sq Ft

  2 Dewitt Dr, Chappaqua, NY 10514

  Welcome to 2 DeWitt Drive — a stunning 2025-built carriage home offering refined luxury and effortless living in one of Chappaqua’s most desirable communities. This light-filled corner residence spans 3,574 square feet with 2 spacious bedrooms (with options for more) and 3.5 baths, thoughtfully designed with high-end finishes and sophisticated upgrades throughout. Expansive windows flood the home

  Joann Galluccio William Raveis-New York LLC

  2 Dewitt Dr, Chappaqua, NY 10514
• 

  

  /13

  $4,500 per month

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Townhouse for Rent

  150 N Bedford Rd Unit 2F, Chappaqua, NY 10514

  Spacious, light filled townhouse close to restaurants, town and train. Features include a large great room with fireplace, walls of glass and sliders to large balcony. A kitchen, separate dining room , powder room and laundry complete the first floor. The 2nd floor offers a spacious primary with en suite bath and a 2nd private bedroom with en suite bath and loft space.2 assigned spaces and

  Barbara Pagliuca Houlihan Lawrence Inc.

  150 N Bedford Rd Unit 2F, Chappaqua, NY 10514
• 

  $2,475,000 Sold May 06, 2025

  27 Neustadt Ln, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 4,974 Sq Ft
  • Built 1986

  Last Sold Summary

  • 29% Above List Price
  • $498/SF
  • 8 Days On Market

  Current Estimated Value $2,463,746

  Last Listing Agent Joanne Milch William Raveis-New York, LLC

  27 Neustadt Ln, Chappaqua, NY 10514
• 

  Est $834,128 Not Listed For Sale

  70 Leroy Rd, Chappaqua, NY 10514

  70 Leroy Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 11% Above List Price
  • 56 Days On Market

  Last Sold Price $749,000

  Last Listing Agent Jaimme Pudalov Houlihan Lawrence Inc.
• 

  

  /39

  $1,450,000 Pending

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

  40 Smith St, Chappaqua, NY 10514

  Step into a story of timeless elegance in this enchanting 1920s village colonial, where the romantic allure of yesteryear meets the effortless luxury of modern living. Located in the heart of the village, this home offers a lifestyle of rare convenience—just a gentle stroll to vibrant shops, local cafes, and the morning train.Inside, the home whispers of its storied past through beautifully

  Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  40 Smith St, Chappaqua, NY 10514
• 

  

  /10

  $2,200 per month

  • 1 Bed
  • 1 Bath
  • 832 Sq Ft
  • Apartment for Rent

  85 Paulding Dr, Chappaqua, NY 10514

  Bright one=bedroom accessory apartment in Chappaqua. Open floor plan gives a spacious feel. Sliding glass door opens to large deck running the length of the unit. Enjoy beautiful vistas in this private setting. Heat, electricity, water, trash and snow removal included in the rent. Driveway parking available for one car. Home is equipped with a generator in case of power outage. No pets allowed.

  Mary Grant Houlihan Lawrence Inc.

  85 Paulding Dr, Chappaqua, NY 10514
• 

  $805,000 Sold Nov 21, 2025

  149 King St Unit 4, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,767 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $456/SF
  • 105 Days On Market

  Last Listing Agent Nancy Jones Julia B Fee Sothebys Int. Rlty

  149 King St Unit 4, 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

  • $489/SF
  • 5 Days On Market

  Last Sold Price $1,631,110

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

  

  /13

  $2,000,000

  • 4 Beds
  • 2.5 Baths
  • 4,500 Sq Ft

  0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514

  Custom design your dream home in a seamless process with ZappiCo, Westchester County's premier Real Estate Developer! This luxurious home is to-be-built in the highly desirable Chappaqua school district. With 4 spacious bedrooms and 2.5 beautifully appointed bathrooms, this home will be meticulously crafted with the finest materials and attention to detail. As you enter, you will be greeted by an

  Rachel Lacoste Houlihan Lawrence Inc.

  0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514
• 

  $1,850,000 Sold Jul 15, 2025

  22 Mountain Peak Rd, Chappaqua, NY 10514

  • 5 Beds
  • 4.5 Baths
  • 4,419 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Above List Price
  • $419/SF
  • 17 Days On Market

  Current Estimated Value $1,879,304

  Last Listing Agent Usha Subramaniam Compass Greater NY, LLC

  22 Mountain Peak 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

  • $569/SF
  • 3 Days On Market

  Last Sold Price $1,763,056

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

  

  /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
• 

  $2,700,000 Sold May 09, 2025

  3 Bradley Farms, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 5,947 Sq Ft
  • Built 1947

  Last Sold Summary

  • 2% Above List Price
  • $454/SF
  • 15 Days On Market

  Current Estimated Value $2,722,420

  Last Listing Agent Amrita Singh William Raveis-New York, LLC

  3 Bradley Farms, 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

  • $524/SF
  • 117 Days On Market

  Last Sold Price $1,624,375

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

  

  /43

  $1,699,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 4,780 Sq Ft

  790 Hardscrabble Rd, Chappaqua, NY 10514

  A Timeless Colonial, Thoughtfully Reimagined for the Way We Live Today There is a certain feeling you get the moment you arrive, a sense of history, warmth, and quiet refinement. Set on a lush, level acre within the coveted Chappaqua School District, this stately Colonial has been beautifully renovated to honor its classic roots while embracing modern comfort and flexibility. The home’s striking

  Kile Boga-Ibric Houlihan Lawrence Inc.

  790 Hardscrabble Rd, Chappaqua, NY 10514
• 

  $1,465,000 Sold Oct 01, 2025

  33 High Way, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 1,917 Sq Ft
  • Built 1938

  Last Sold Summary

  • 22% Above List Price
  • $764/SF
  • 11 Days On Market

  Current Estimated Value $1,485,959

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC

  33 High Way, 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

  • $524/SF
  • 5 Days On Market

  Last Sold Price $1,626,348

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

  

  /34

  $1,450,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,885 Sq Ft

  18 Hayrake Ln, Chappaqua, NY 10514

  Nestled on one of Chappaqua’s most desirable cul-de-sac neighborhoods, this move-right-in, Bradley-built 5-bedroom Cape is privately set and offers the perfect blend of refined living and everyday comfort. Sun-filled interiors exude warmth and character, with graciously sized rooms and a highly versatile layout designed to grow with your family. The main level features a spacious living room with

  Danae Richards William Raveis-New York, LLC

  18 Hayrake Ln, Chappaqua, NY 10514
• 

  $765,000 Sold Apr 07, 2025

  12 Pines Ln, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 2,249 Sq Ft
  • Built 1948

  Last Sold Summary

  • 4% Below List Price
  • $340/SF
  • 93 Days On Market

  Current Estimated Value $858,412

  Last Listing Agent David Turner Compass Greater NY, LLC

  12 Pines Ln, Chappaqua, NY 10514
• 

  Est $1,968,629 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

  • 11% Above List Price
  • $374/SF
  • 116 Days On Market

  Last Sold Price $1,775,000

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

  

  /23

  $1,425,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,921 Sq Ft

  110 Marcourt Dr, Chappaqua, NY 10514

  Picturesque and spectacular center hall Colonial, beautifully situated on a cul de sac in the highly sought-after Dodge Farms neighborhood of Chappaqua. This sun-filled home blends suburban convenience with timeless warmth and character, offering generous-sized rooms and remarkable versatility throughout. The thoughtfully renovated chef's kitchen and baths complement a seamless flow ideal for

  Stephanie Garbuio Houlihan Lawrence Inc.

  110 Marcourt Dr, Chappaqua, NY 10514
• 

  $2,300,000 Sold Nov 20, 2025

  24 North Way, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 3,960 Sq Ft
  • Built 1986

  Last Sold Summary

  • 24% Above List Price
  • $581/SF
  • 7 Days On Market

  Current Estimated Value $2,220,099

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate

  24 North Way, Chappaqua, NY 10514
• 

  Est $1,755,044 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

  • 6% Above List Price
  • $407/SF
  • 9 Days On Market

  Last Sold Price $1,662,500

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  

  /38

  $1,150,000 Pending

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

  200 S Bedford Rd, Chappaqua, NY 10514

  Completely updated and remodeled residence in the heart of Chappaqua, offering a highly versatile layout ideal for in-law suite, professional office, and/or apartment use. The home features two bedrooms plus an office in the main residence, plus a private, 1-bedroom legal accessory apartment currently generating $2,500 per month in rental income. The property also offers the flexibility to live

  Annette Cicinelli Keller Williams Realty Partner

  200 S Bedford Rd, Chappaqua, NY 10514
• 

  $1,550,000 Sold Jan 20, 2026

  100 Old Farm Rd N, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,971 Sq Ft
  • Built 2010

  Last Sold Summary

  • 19% Above List Price
  • $522/SF
  • 13 Days On Market

  Current Estimated Value $1,344,160

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  100 Old Farm Rd N, 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

  • $588/SF
  • 115 Days On Market

  Last Sold Price $1,990,428

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

  

  /18

  $699,000 Pending

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

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

  Immaculate townhouse in a desirable walk-to-town location close to shops, restaurants, and the train. Refinished maple hardwood floors, custom built-ins, and a fireplace define the main living level, highlighted by a dramatic wall of windows with sunset views. Newer Pella sliders open to a private deck for seamless indoor-outdoor living. Custom stair railings, upgraded solid interior doors, and

  Sari Shaw Compass Greater NY, LLC

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

  $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 $1,617,966

  Last Listing Agent Catherine O'Connor Houlihan Lawrence Inc.

  395 Bedford Rd, Chappaqua, NY 10514

Showing Results 1 - 40, Page 1 of 18