4,418

Chappaqua, NY Homes

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  • /21

    $510,000

    Pending
    • 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

    Agent Photo

    Donna McKenna Edlund

    Coldwell Banker Realty

    (914) 537-3558

    368 N Greeley Ave Unit 34G, Chappaqua, NY 10514
  • /25

    Starting at $3,237 Per Month

    • 1 - 3 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

    Chappaqua Crossing Apartments

    (914) 340-5070

    480 Bedford Rd, Chappaqua, NY 10514
  • 36 Pond Hill 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 $1,587,630

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

    36 Pond Hill Rd, Chappaqua, NY 10514
  • /36

    $1,975,000

    Pending
    • 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

    Agent Photo

    Usha Subramaniam

    Compass Greater NY, LLC

    (914) 977-0609

    111 Prospect Dr, Chappaqua, NY 10514
  • /19

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Townhouse for Rent

    311 N Greeley Ave Unit 6A, Chappaqua, NY 10514

    Bright contemporary 2-bedroom and 2-bathroom townhouse in desirable Chestnut Oaks. Enter through the foyer to the eat-in kitchen featuring a counter and stainless steel appliances. The formal dining area overlooks the sun-filled living room with vaulted ceilings, a wood-burning fireplace, and a sliding door to a patio and fabulous yard. Upstairs, you will find a bedroom and a full bath. Off the

    Nargis Rakhmatova Compass Greater NY, LLC

    311 N Greeley Ave Unit 6A, Chappaqua, NY 10514
  • 70 Haights Cross 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 $3,059,209

    Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

    70 Haights Cross Rd, Chappaqua, NY 10514
  • /38

    $1,249,000

    Pending
    • 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
  • /30

    $11,500 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,202 Sq Ft
    • Modern Farmhouse 3 Bedroom 3.5 Barhroom

    1111 Hardscrabble Rd, Chappaqua, NY 10514

    Modern Farmhouse - Prime Location! Experience luxury living in this newly constructed custom-built modern farmhouse, Mere minutes from downtown Chappaqua and the train station. Situated on a beautiful flat yard, this meticulously crafted home offers the epitome of comfort and style.Key Features:- Spacious first-floor bedroom, providing luxurious comfort and convenience.-

    1111 Hardscrabble Rd, Chappaqua, NY 10514
  • 149 King St Unit 4, 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
  • /29

    $1,199,000

    • 4 Beds
    • 2.5 Baths
    • 2,207 Sq Ft

    21 Campfire Rd, Chappaqua, NY 10514

    Move right into this sparkling, beautifully updated 4-bedroom Colonial, ideally located in the highly sought-after Chappaqua School District. Blending timeless pre-war charm with modern amenities, this home offers exceptional comfort and style. Freshly painted inside and out, the home features beautiful hardwood floors, recessed lighting, a renovated kitchen, updated bathrooms, a wood burning

    Cindy Glynn Compass Greater NY, LLC

    21 Campfire Rd, Chappaqua, NY 10514
  • /12

    $3,495 Per Month

    • 1 Bed
    • 1.5 Baths
    • 957 Sq Ft
    • Apartment for Rent

    480 Bedford Rd Unit 110, Chappaqua, NY 10514

    Stunning 1 loft Bedroom, 1.5 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

    Donna Lee Blais Northridge Realty

    480 Bedford Rd Unit 110, Chappaqua, NY 10514
  • 22 Mountain Peak Rd, 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 $1,986,892

    Last Listing Agent Usha Subramaniam Compass Greater NY, LLC

    22 Mountain Peak Rd, Chappaqua, NY 10514
  • /50

    $2,699,000

    • 4 Beds
    • 4.5 Baths
    • 5,918 Sq Ft

    40 Hamilton Dr, Chappaqua, NY 10514

    Tucked away on over two exquisitely landscaped acres in one of Chappaqua’s most prestigious enclaves, this exceptional newly constructed modern home redefines luxury living through a masterful blend of architectural sophistication, cutting-edge efficiency, and timeless elegance. Designed with a discerning eye and crafted with uncompromising quality, this magazine-worthy residence offers the

    Matthew Valvano Berkshire Hathaway HS NY Prop

    40 Hamilton Dr, Chappaqua, NY 10514
  • /44

    $10,000 Per Month

    • 3 Beds
    • 4 Baths
    • 3,320 Sq Ft
    • Stunning Updated Home with Private Pond Views in Chappaqua

    8 Granite Rd, Chappaqua, NY 10514

    Nestled on a beautifully landscaped property, this exceptional home offers the perfect blend of tranquility and convenience. Featuring an airy open-concept layout across three levels, the residence is filled with natural light and scenic views throughout.The beautifully renovated eat-in kitchen and dining area include radiant heated floors and flow into the spacious living room, where

    8 Granite Rd, Chappaqua, NY 10514
  • 110 Marcourt Dr, Chappaqua, NY 10514

    $1,905,000

    Sold Jun 02, 2026

    110 Marcourt Dr, Chappaqua, NY 10514

    • 4 Beds
    • 2.5 Baths
    • 2,921 Sq Ft
    • Built 1961

    Last Sold Summary

    • 34% Above List Price
    • $652/SF
    • 6 Days On Market

    Current Estimated Value $1,528,759

    Last Listing Agent Stephanie Garbuio Houlihan Lawrence Inc.

    110 Marcourt Dr, Chappaqua, NY 10514
  • /43

    $1,495,000

    • 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
  • /18

    $6,250 Per Month

    • 2 Beds
    • 1.5 Baths
    • 2,220 Sq Ft
    • House for Rent

    105 Douglas Rd, Chappaqua, NY 10514

    Set far back from the road in a private and peaceful setting, this beautifully maintained home offers exceptional flexibility in the highly sought-after Chappaqua School District, just moments to town, Metro-North train to NYC, parks, shopping, and restaurants. Offering a flexible layout with 2 legal bedrooms plus additional office and bonus spaces that can live like a 3- or 4-bedroom home, this

    Karin Kimtis Compass Greater NY, LLC

    105 Douglas Rd, Chappaqua, NY 10514
  • 33 High Way, 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 $1,537,702

    Last Listing Agent Jennifer Harris Compass Greater NY, LLC

    33 High Way, Chappaqua, NY 10514
  • /26

    $1,095,000

    Pending
    • 4 Beds
    • 4 Baths
    • 2,108 Sq Ft

    3 Elm St, Chappaqua, NY 10514

    Discover this 4-bed two-family home in Chappaqua, NY, offering strong income potential, a prime village location, and excellent commuter convenience just one mile from the train. Ideal for investors or owner-occupants, this updated colonial duplex features two fully leased 2-bedroom, 2-bath units, each with approximately 1,054 square feet, private in-unit laundry, hardwood floors, covered front

    Edward Holmes William Raveis-New York, LLC

    3 Elm St, Chappaqua, NY 10514
  • /12

    $6,850 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft
    • Apartment for Rent

    480 Bedford Rd Unit 401, Chappaqua, NY 10514

    Stunning 3 Bedroom, 2.5 baths with loft 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

    Donna Lee Blais Northridge Realty

    480 Bedford Rd Unit 401, Chappaqua, NY 10514
  • 100 Old Farm Rd N, 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 $1,535,011

    Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

    100 Old Farm Rd N, Chappaqua, NY 10514
  • /48

    $1,998,999

    • 4 Beds
    • 3.5 Baths
    • 3,124 Sq Ft

    4 Old House Ln, Chappaqua, NY 10514

    Nestled on over an acre of beautifully landscaped grounds in the highly sought-after Chappaqua School District, this exceptional residence offers a rare blend of privacy, craftsmanship, and versatility. Behind a gated entrance, mature specimen plantings, expansive lawns, and a tranquil natural setting create a true private retreat just minutes from downtown Chappaqua and Metro-North. Thoughtfully

    Laura Lulgjuraj Houlihan Lawrence Inc.

    4 Old House Ln, Chappaqua, NY 10514
  • /23

    $3,675 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    352 N Greeley Ave, Chappaqua, NY 10514

    This spacious bi-level apartment is in Chestnut Oaks Condominium located just half a mile from the train station and downtown shops. It is bright and open with high cathedral ceiling. Kitchen, living room and powder room are on the main level, with sliding doors leading to a patio. On cold nights you will enjoy the fireplace that is decorating the llvingroom wall. On the second floor is a large

    Gabriela Kosek ERA Insite Realty Services

    352 N Greeley Ave, Chappaqua, NY 10514
  • 19 Wallace Way Unit 25, 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 $1,777,316

    Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

    19 Wallace Way Unit 25, Chappaqua, NY 10514
  • /39

    $1,199,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 2,708 Sq Ft

    25 Cabin Ridge Rd, Chappaqua, NY 10514

    Escape to your own private retreat on 3.44 acres of wooded land, where rustic charm meets modern comfort. This unique residence was thoughtfully expanded in 2005 and refined with modern luxuries while preserving its timeless character. The beautifully crafted, freshly painted 2,708-square-foot home offers 3 bedrooms and 4 bathrooms in a serene, nature-filled setting. Inside, you'll find a

    Jia Wei Keller Williams Realty Group

    25 Cabin Ridge Rd, Chappaqua, NY 10514
  • /34

    $11,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 4,345 Sq Ft
    • House for Rent

    3 Breckenridge Rd, Chappaqua, NY 10514

    Privately set on two beautifully level acres in Chappaqua’s sought-after Whippoorwill neighborhood, this sophisticated contemporary offers exceptional light, space, and seamless indoor-outdoor living. Thoughtfully updated and impeccably maintained, the home is surrounded by tranquil natural beauty with picturesque views from nearly every room. A dramatic open floor plan is enhanced by soaring

    Bonnie Field Besner Houlihan Lawrence Inc.

    3 Breckenridge Rd, Chappaqua, NY 10514
  • 5 Briarcliff Rd, 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 $3,614,719

    Last Listing Agent Sari Shaw Compass Greater NY, LLC

    5 Briarcliff Rd, Chappaqua, NY 10514
  • /21

    $1,195,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,178 Sq Ft

    26 Meadow Ln, Chappaqua, NY 10514

    Welcome to 26 Meadow Lane, a pristine 2,178-square-foot ranch set on over half an acre of flat, beautifully landscaped property in one of Chappaqua’s most coveted residential neighborhoods. A rocking chair front porch and Belgian block-lined driveway offer an immediate sense of arrival, while sidewalk-lined streets connect the neighborhood to the acclaimed village of Chappaqua, minutes from

    Lauren Zaccaria Houlihan Lawrence Inc.

    26 Meadow Ln, Chappaqua, NY 10514
  • /16

    $4,900 Per Month

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • Apartment for Rent

    91 Bedford Rd Unit 2, Chappaqua, NY 10514

    Unparalleled opportunity to attain one of the only 2 exceptional apartments in the corner turret at the newly constructed building in the heart of Chappaqua. Quality construction by a highly regarded local builder. This apartment features a stunning octagonal living room/dining room, 2 bedrooms and 2 full baths/ADA shower. Glamorous modern styling quartz counters, island open to bright open floor

    Grace Priore ERA Insite Realty Services

    91 Bedford Rd Unit 2, Chappaqua, NY 10514
  • 149 King St Unit 15, 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

Showing Results 1 - 40, Page 1 of 18

Home Prices in Chappaqua, NY

Home Price Trends

Median Sale Price
$1,605,000
Median Single Family Sale Price
$1,600,000
Median Townhouse Sale Price
$1,665,164
Median 2 Bedroom Sale Price
$1,389,114
Median 1 Bedroom Sale Price
$464,500
Average Price Per Sq Ft
$521
Number of Homes for Sale
18
Last 12 months Home Sales
133
Months of Supply
1.60
Median List Price
$1,450,000
Median Change From 1st List Price
-5%
Median Home Sale Price YoY Change
3%
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