Chappaqua, NY Homes

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  $1,550,000 Open Sat 12PM - 3PM

  • 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

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  /25

  $3,775 - $5,300 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
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  $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 $1,606,014

  Last Listing Agent Christopher Rose REALHome Services & Solutions

  50 North Place, Chappaqua, NY 10514
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  Est $1,372,333 Not Listed For Sale

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

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514
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  $1,375,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,891 Sq Ft

  7 Byram Meadows Rd, Chappaqua, NY 10514

  Welcome to this beautifully maintained home featuring a spacious 476 sq ft sunroom with direct access from both the living room and family room—ideal for year-round enjoyment. Recent updates include new central air unit (2022) and all new water systems in the basement. The family room boasts a classic wood-burning fireplace, perfect for cozy evenings. Enjoy a formal dining room and an eat-in

  Ken Wile Redfin Real Estate

  7 Byram Meadows Rd, Chappaqua, NY 10514
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  /40

  $10,000 per month

  • 3 Beds
  • 3.5 Baths
  • 4,780 Sq Ft
  • House for Rent

  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
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  $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

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  70 Haights Cross Rd, Chappaqua, NY 10514
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  Est $1,772,999 Not Listed For Sale

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

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514
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  $1,299,500 Pending

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

  36 Pond Hill Rd, Chappaqua, NY 10514

  Set on a quiet cul-de-sac, this charming 3-bedroom Cape, which could live like a 4-bedroom, offers the perfect blend of comfort, convenience, and style. The home has been impeccably maintained and thoughtfully renovated, with updates that make it truly move-in ready.From the moment you arrive, the curb appeal stands out, enhanced by updated landscaping and a freshly painted exterior. Inside,

  Danae Richards William Raveis-New York, LLC

  36 Pond Hill Rd, Chappaqua, NY 10514
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  $5,750 per month

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Townhouse for Rent

  103 Rambling Brook Rd, Chappaqua, NY 10514

  Beautifully updated townhome overlooking a picturesque lake with a private yard. Features two primary bedrooms, a large family room or office, modern eat-in kitchen with stainless steel appliances and quartz countertops, plus dining and living rooms with cathedral ceilings. Private stone patio off the kitchen and oversized deck with lake views.Community amenities include tennis courts, pool,

  Sandra Scarano William Raveis Real Estate

  103 Rambling Brook Rd, Chappaqua, NY 10514
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  $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 $2,512,329

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

  27 Neustadt Ln, Chappaqua, NY 10514
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  Est $1,624,145 Not Listed For Sale

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

  265 Mill River Rd, Chappaqua, NY 10514

  265 Mill River Rd, Chappaqua, NY 10514
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  $839,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,648 Sq Ft

  11 Pondview Close Unit 37, Chappaqua, NY 10514

  Updated end-unit townhome with an oversized patio, featuring 3 bedrooms, 2.1 baths, and a spacious loft in the sought-after Apple Hill Farm complex. Airy and private. Tranquil setting among apple orchards and woody walking trails by the pond. This beautiful unit has been extensively renovated and offers hardwood floors throughout, fresh paint, an updated kitchen with stainless steel appliances

  Alicja Bohmrich Houlihan Lawrence Inc.

  11 Pondview Close Unit 37, Chappaqua, NY 10514
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  /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
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  $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
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  Est $847,232 Not Listed For Sale

  70 Leroy Rd, Chappaqua, NY 10514

  70 Leroy Rd, Chappaqua, NY 10514
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  /20

  $475,000 Open Sat 12PM - 2PM

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

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

  Location, Location, Location! Chestnut Oak Complex. Dramatic and bright townhouse with natural lighting. This 1 bedroom 1.1 bath plus huge Loft/Den is in mint condition. Updated kitchen with stainless-steel appliances. Living room with high ceilings, fireplace and wall of windows is combined with spacious dining area. Updated powder room on the first level. Huge primary bedroom with with two

  Alicja Bohmrich Houlihan Lawrence Inc.

  356 N Greeley Ave Unit 28G, Chappaqua, NY 10514
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  $3,775 per month

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

  480 Bedford Rd Unit 208, Chappaqua, NY 10514

  One bedroom plus den apartment the Chappaqua Crossing Community. Two landscaped interior courtyards. On-site walking trail. Resident superintendent and on-site property management. Outdoor playground area, large gym and separate exercise room, Two laundry rooms, Beautiful club/multi-purpose room, including kitchenette. Elegant reading library with dramatic views. The apartment features Luxury

  Donna Lee Blais Northridge Realty

  480 Bedford Rd Unit 208, Chappaqua, NY 10514
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  $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 $1,896,329

  Last Listing Agent Usha Subramaniam Compass Greater NY, LLC

  22 Mountain Peak Rd, Chappaqua, NY 10514
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  Not Listed For Sale

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

  45 Lila Ln Unit 62, Chappaqua, NY 10514

  45 Lila Ln Unit 62, Chappaqua, NY 10514
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  $1,749,000 Pending

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

  2 Whippoorwill Close, Chappaqua, NY 10514

  Exceptionally renovated and truly turnkey, this striking Whippoorwill cul-de-sac Contemporary is located in the highly acclaimed Chappaqua School District. Dramatic, airy, and light-filled, the 4-bedroom home is set in a serene and sought-after neighborhood, offering both privacy and convenience. A wall of windows, skylights, soaring ceilings, and an open floor plan flood the interiors with

  Cindy Glynn Compass Greater NY, LLC

  2 Whippoorwill Close, Chappaqua, NY 10514
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  /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
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  $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 $2,755,381

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

  3 Bradley Farms, Chappaqua, NY 10514
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  Not Listed For Sale

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

  41 Lila Ln Unit 60, Chappaqua, NY 10514

  41 Lila Ln Unit 60, Chappaqua, NY 10514
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  $1,650,000 Pending

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

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514

  Welcome to this sophisticated 4-bedroom, 3.5-bath contemporary residence, perfectly designed for today’s lifestyle with a seamless blend of modern style and functional comfort. Set on a gracious property, this home offers open, luminous living spaces flooded with natural light and thoughtful architectural detail throughout. At the heart of the home, a beautifully appointed kitchen opens to a

  Sari Shaw Compass Greater NY, LLC

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514
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  /11

  $5,300 per month

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft
  • Apartment for Rent

  480 Bedford Rd Unit 210, Chappaqua, NY 10514

  Stunning 2 Bedroom, 2 baths apartment the Chappaqua Crossing Community. Two landscaped interior courtyards. On-site walking trail. Resident superintendent and on-site property management. Outdoor playground area, large gym and separate exercise room, Two laundry rooms, Beautiful club/multi-purpose room, including kitchenette. Elegant reading library with dramatic views. The apartment features

  Donna Lee Blais Northridge Realty

  480 Bedford Rd Unit 210, Chappaqua, NY 10514
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  $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 $1,451,001

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC

  33 High Way, Chappaqua, NY 10514
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  Not Listed For Sale

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

  39 Lila Ln Unit 59, Chappaqua, NY 10514

  39 Lila Ln Unit 59, Chappaqua, NY 10514
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  $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
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  /26

  $8,000 per month

  • 4 Beds
  • 3 Baths
  • 3,141 Sq Ft
  • House for Rent

  49 Commodore Rd, Chappaqua, NY 10514

  Picture perfect center hall colonial. Ideal executive rental, walk to town and train. Living room with fireplace, dining room with sliders to large deck, and modern eat-in kitchen. Bedroom and full bath on first level, perfect for au-pair or guest suite. Primary bedroom with en-suite bath, featuring double sink vanity, jacuzzi tub and stand alone shower. Two more hall bedrooms, well-appointed

  Gail Silverstein ERA Insite Realty Services

  49 Commodore Rd, Chappaqua, NY 10514
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  $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 $857,605

  Last Listing Agent David Turner Compass Greater NY, LLC

  12 Pines Ln, Chappaqua, NY 10514
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  Est $1,888,000 Not Listed For Sale

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

  2 Point Place, Chappaqua, NY 10514

  2 Point Place, Chappaqua, NY 10514
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  $1,199,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,069 Sq Ft

  111 Seven Bridges Rd, Chappaqua, NY 10514

  Welcome to this sparkling sun-filled ranch, this beautifully updated 4 bedroom/2.1 bath home offers an easy living floorplan, lovely landscaped property and easy access to top rated schools, shops and commuter train. Over 2000 sq ft, on an acre, offering privacy amidst a neighborhood feel. Newly renovated bathrooms, updated kitchen, freshly painted interior, and gleaming newly refinished white

  Sena Baron William Raveis-New York, LLC

  111 Seven Bridges Rd, Chappaqua, NY 10514
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  /11

  $3,600 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  327 N Greeley Ave, Chappaqua, NY 10514

  Walk to town shops, restaurants, park, library, farmers market and commuter train from this conveniently located well established condo complex in the heart of Chappaqua. Bright, sunny, meticulously maintained ground floor one level unit is move-in ready and features a fireplace, patio, recessed lighting, renovated kitchen with quartzite counters, renovated bathroom and ample closet space

  Sena Baron William Raveis-New York, LLC

  327 N Greeley Ave, Chappaqua, NY 10514
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  $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

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate

  24 North Way, Chappaqua, NY 10514
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  Not Listed For Sale

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

  35 Lila Ln Unit 57, Chappaqua, NY 10514

  35 Lila Ln Unit 57, Chappaqua, NY 10514
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  /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
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  $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

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  100 Old Farm Rd N, Chappaqua, NY 10514
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  Not Listed For Sale

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

  33 Lila Ln Unit 56, Chappaqua, NY 10514

  33 Lila Ln Unit 56, Chappaqua, NY 10514
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  $1,100,000 Open Sat 11AM - 2:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,445 Sq Ft

  29 Meadow Ln, Chappaqua, NY 10514

  Welcome to 29 Meadow Lane, ideally tucked away on a quiet, picturesque cul-de-sac in the heart of Chappaqua. Set on over half an acre of beautifully landscaped, private property, this fully updated ranch offers flexible living, modern comfort, and an exceptional location. Sidewalk-lined streets lead from the neighborhood into bucolic downtown Chappaqua, just minutes from shops, dining, and the

  Lauren Zaccaria Houlihan Lawrence Inc.

  29 Meadow Ln, Chappaqua, NY 10514

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