Chappaqua, NY Homes

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  /36

  $1,975,000

  • 5 Beds
  • 3.5 Baths
  • 4,166 Sq Ft

  111 Prospect Dr, Chappaqua, NY 10514

  Exquisite architectural design, timeless charm & luxurious modern amenities merge effortlessly in this elegant Colonial in the heart of Chappaqua. C.1902 & superbly upgraded and meticulously maintained, the home offers an open, sun-bathed interior w/hardwood floors, high ceilings, abundant built-ins, extensive millwork and a quintessential porch - sure to please the most discerning buyers! The

  

  Usha Subramaniam

  Compass Greater NY, LLC

  (914) 977-0609

  111 Prospect Dr, Chappaqua, NY 10514
• Explore Chappaqua

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  /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
• 

  $1,600,000 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 $1,379,076

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

  36 Pond Hill Rd, Chappaqua, NY 10514
• 

  Est $1,296,667 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

  • $652/SF
  • 11 Days On Market

  • Last Sold Price $1,300,000
  • Sep 04, 2024

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate
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  /21

  $510,000

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

  368 N Greeley Ave Unit 34G, Chappaqua, NY 10514

  Welcome to Chestnut Oaks, a sought-after condominium community just moments from downtown Chappaqua. This sun-filled 1-bedroom plus loft and den residence offers 5 well-designed rooms, 1.1 updated baths, and a flexible layout ideal for today’s living. The inviting entry hall features tile flooring and a generous closet, leading to an updated powder room accented by a charming octagonal window and

  

  Donna McKenna Edlund

  Coldwell Banker Realty

  (914) 537-3558

  368 N Greeley Ave Unit 34G, Chappaqua, NY 10514
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  /26

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Townhouse for Rent

  343 N Greeley Ave Unit 8D, Chappaqua, NY 10514

  Commuter’s Delight! Fabulous sun-filled completely updated 2 bedroom, 2 bath end unit with den/work from home office and oversized shared 1 car garage in desirable Chestnut Oaks complex. Chappaqua schools. Short distance to Chappaqua village, train station, shops and restaurants. The 1st level features an entry foyer with coat closet leading to the renovated chef’s eat-in-kitchen with quartz

  Alisa Kaplan Julia B Fee Sothebys Int. Rlty

  343 N Greeley Ave Unit 8D, 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 $2,949,884

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  70 Haights Cross Rd, Chappaqua, NY 10514
• 

  Est $1,751,829 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

  • 17% Above List Price
  • $405/SF
  • 54 Days On Market

  • Last Sold Price $1,499,000
  • Aug 25, 2023

  Last Listing Agent Mary Ann Tighe Houlihan Lawrence Inc.
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  /49

  $2,475,000 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
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  /9

  $2,900 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  150 N Bedford Rd Unit 1E, Chappaqua, NY 10514

  Storybook 1-Bedroom with Expansive Private Terrace in the Heart of Chappaqua. Welcome to a rare offering that seamlessly blends comfort, style, and outdoor living. This thoughtfully designed condo features an exceptional 300 sq. ft. private terrace, bringing your total usable space to nearly 1,100 sq. ft.—perfect for those who value space, light, and a connection to the outdoors. Step inside to

  Inaam Rahman Julia B Fee Sothebys Int. Rlty

  150 N Bedford Rd Unit 1E, 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 $2,462,862

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

  27 Neustadt Ln, Chappaqua, NY 10514
• 

  Est $1,537,597 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

  • 30% Above List Price
  • $246/SF
  • 68 Days On Market

  • Last Sold Price $1,185,000
  • May 31, 2024

  Last Listing Agent Sandra Cappucci Julia B Fee Sothebys Int. Rlty
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  /32

  $1,949,000 Pending

  • 4 Beds
  • 5 Baths
  • 5,767 Sq Ft

  5 Morning View Ct, Chappaqua, NY 10514

  A refined expression of modern Colonial living, this exceptional 4-bedroom, 5 full bath residence offers nearly 6,000 square feet of impeccably finished space, including a walk-out lower level, in one of Chappaqua’s most coveted settings. Built in 2012 and featuring natural gas and municipal sewer—an uncommon and highly desirable pairing—this home delivers a rare combination of quality, scale,

  Sari Shaw Compass Greater NY, LLC

  5 Morning View Ct, Chappaqua, NY 10514
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  /36

  $6,200 per month

  • 3 Beds
  • 2 Baths
  • 2,082 Sq Ft
  • House for Rent

  64 Pine Cliff Rd, Chappaqua, NY 10514

  In the Heart of Chappaqua! Beautiful, sparkling, updated and very bright home in immaculate condition. This 3 Bedroom plus Office/, Playroom and 2 Baths home is nestled next to the Pinecliff Sanctuary and at the end of the cul-de-sac. It has all: Living Room with Fireplace and walls of windows, Dining Area, Sun Room, Updated Kitchen with granite countertops and Sliding Glass Door to huge deck and

  Alicja Bohmrich Houlihan Lawrence Inc.

  64 Pine Cliff Rd, 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
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  Est $839,224 Not Listed For Sale

  70 Leroy Rd, Chappaqua, NY 10514

  70 Leroy Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 12% Above List Price
  • 56 Days On Market

  • Last Sold Price $749,000
  • Aug 12, 2024

  Last Listing Agent Jaimme Pudalov Houlihan Lawrence Inc.
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  /33

  $2,300,000 Pending

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

  24 North Way, Chappaqua, NY 10514

  AO-3/29-Move-in ready, light and bright 3 bedroom/ 3.5 bathroom home that lives like a 4 bedroom in the coveted Lawrence Farms South neighborhood with a private, flat backyard with a stone patio, heated gunite pool and a charming pergola. This inviting home with high ceilings throughout, offers a spacious living room with a fireplace, adjacent to a formal dining room, both with glass door access

  Pamela Akin Douglas Elliman Real Estate

  24 North Way, 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
• 

  $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 $1,909,675

  Last Listing Agent Usha Subramaniam Compass Greater NY, LLC

  22 Mountain Peak Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

  149 King St Unit 19, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,664 Sq Ft
  • Built 1988

  149 King St Unit 19, Chappaqua, NY 10514

  Last Sold Summary

  • $526/SF
  • 6 Days On Market

  • Last Sold Price $875,000
  • Apr 03, 2025

  Last Listing Agent Alicja Bohmrich Houlihan Lawrence Inc.
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  /13

  $2,000,000 Pending

  • 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
• 

  $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 $2,779,273

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

  3 Bradley Farms, Chappaqua, NY 10514
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  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
  • Feb 25, 2025

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

  $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 $1,481,971

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC

  33 High Way, Chappaqua, NY 10514
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  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
  • Jan 07, 2025

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

  $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 $1,447,158

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  100 Old Farm Rd N, Chappaqua, NY 10514
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  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
  • Jan 21, 2025

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.
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  /38

  $1,925,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,489 Sq Ft

  1 Hitching Post Ln, Chappaqua, NY 10514

  Welcome to this warm, inviting 5-bedroom home nestled on a tree-lined beautiful Chappaqua street. It has a lovely front porch with plenty of room for cozy chairs, perfect for sipping coffee in the morning. Inside, there is a spacious living room with a wood burning fireplace, a bright kitchen and a large island. First floor features a Primary Suite, 4 additional bedrooms with 2 full baths

  Yona Strougo Compass Greater NY, LLC

  1 Hitching Post Ln, 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 $1,621,098

  Last Listing Agent Catherine O'Connor Houlihan Lawrence Inc.

  395 Bedford Rd, Chappaqua, NY 10514
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  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
  • Nov 15, 2024

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

  $1,659,995 Sold Sep 10, 2025

  19 Wallace Way Unit 25, Chappaqua, NY 10514

  • 2 Beds
  • 4 Baths
  • 3,432 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $484/SF
  • 91 Days On Market

  Current Estimated Value $1,727,711

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

  19 Wallace Way Unit 25, 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
  • Dec 11, 2024

  Last Listing Agent Hayes Hopple Julia B Fee Sothebys Int. Rlty
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  /36

  $1,699,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,483 Sq Ft

  12 Suzanne Ln, Chappaqua, NY 10514

  Perfectly positioned at the end of a quiet cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath Colonial offers the ideal blend of space, comfort, and effortless living—set on expansive, level property designed for both everyday enjoyment and memorable entertaining. A gracious foyer welcomes you, seamlessly opening to the living and dining rooms and creating a natural flow for gatherings.

  Jennifer Harris Compass Greater NY, LLC

  12 Suzanne Ln, Chappaqua, NY 10514
• 

  $3,400,000 Sold Sep 09, 2025

  5 Briarcliff Rd, Chappaqua, NY 10514

  • 4 Beds
  • 7 Baths
  • 7,305 Sq Ft
  • Built 2007

  Last Sold Summary

  • 8% Below List Price
  • $465/SF
  • 65 Days On Market

  Current Estimated Value $3,449,113

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  5 Briarcliff Rd, Chappaqua, NY 10514
• 

  Est $1,742,677 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

  • 5% Above List Price
  • $407/SF
  • 9 Days On Market

  • Last Sold Price $1,662,500
  • Mar 08, 2025

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
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  /38

  $1,249,000

  • 4 Beds
  • 2.5 Baths
  • 2,478 Sq Ft

  14 Aldridge Rd, Chappaqua, NY 10514

  Classic 1920 Colonial brimming with vintage charm and modern updates, ideally located on a desirable cul-de-sac just a short walk to town. This beautifully maintained 4/5-bedroom home features 2 renovated full baths plus a new powder room, a sparkling white renovated kitchen with floor to ceiling cabinetry, stainless steel appliances-Sub Zero, Miele, & Viking and a generous eat-in area with door

  Sena Baron William Raveis-New York, LLC

  14 Aldridge Rd, Chappaqua, NY 10514
• 

  $820,000 Sold Aug 20, 2025

  149 King St Unit 15, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,925 Sq Ft
  • Built 1988

  Last Sold Summary

  • $426/SF
  • 15 Days On Market

  Last Listing Agent Janet Short Houlihan Lawrence Inc.

  149 King St Unit 15, Chappaqua, NY 10514

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