4,418

Chappaqua, NY Homes

Section Image
  • 734 King St, Chappaqua, NY 10514
    734 King St, Chappaqua, NY 10514
    734 King St, Chappaqua, NY 10514
    /39

    $1,599,999

    Pending
    • 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
  • 507 Millwood Rd, Chappaqua, NY 10514
    507 Millwood Rd, Chappaqua, NY 10514
    507 Millwood Rd, Chappaqua, NY 10514
    /10

    $9,500 Per Month

    • 3 Beds
    • 3 Baths
    • 3,136 Sq Ft
    • House for Rent

    507 Millwood Rd, Chappaqua, NY 10514

    Recently renovated raised ranch at 507 Millwood Road in Chappaqua. This spacious home sits on 1.13 private acres featuring mature landscaping, a footbridge and a stream.The 3,136 sq ft home offers 3 bedrooms, 3 bathrooms plus flexible living spaces that can easily function as a office , etc. Updated gourmet kitchen with granite counters, tiled backsplash and stainless steel appliances. The

    Faisal Faisal Faze One Real Estate, LLC

    507 Millwood Rd, Chappaqua, NY 10514
  • 20 Bristol Place, Chappaqua, NY 10514

    $1,835,000

    Sold Jun 30, 2025

    20 Bristol Place, Chappaqua, NY 10514

    • 4 Beds
    • 4 Baths
    • 4,082 Sq Ft
    • Built 1965

    Last Sold Summary

    • 23% Above List Price
    • $450/SF
    • 6 Days On Market

    Current Estimated Value $1,908,333

    Last Listing Agent Kori Sassower Compass Greater NY, LLC

    20 Bristol Place, Chappaqua, NY 10514
  • 10 North Ln, Chappaqua, NY 10514
    10 North Ln, Chappaqua, NY 10514
    10 North Ln, Chappaqua, NY 10514
    /45

    $1,350,000

    $45K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,155 Sq Ft

    10 North Ln, Chappaqua, NY 10514

    Welcome to 10 North Lane, a spacious 3-bedroom, 3-bath home offering 3,155 square feet of comfortable living in the heart of Chappaqua. Located within the highly acclaimed Chappaqua School District, this charming residence is perfectly positioned on a quiet, private cul-de-sac street just minutes from the Taconic Parkway, shopping, and the vibrant Chappaqua town center. Enjoy a beautifully level

    Annette Cicinelli Keller Williams Realty Partner

    10 North Ln, Chappaqua, NY 10514
  • 17 Rambling Brook Rd, Chappaqua, NY 10514
    17 Rambling Brook Rd, Chappaqua, NY 10514
    17 Rambling Brook Rd, Chappaqua, NY 10514
    /32

    $6,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,553 Sq Ft
    • Townhouse for Rent

    17 Rambling Brook Rd, Chappaqua, NY 10514

    Move In Ready, Recently Remodeled Townhouse in Old Farm Lake, Chappaqua. Discover this beautifully updated end unit townhouse offering 3 bedrooms, 3 baths, one car garage, deck, and a bonus room on each level. With a natural organic feel to compliment quiet community settings and landscaping, your new home offers calming sensory attentive features throughout to fit any mood. Enjoy New Designer

    Lauren Zaccaria Houlihan Lawrence Inc.

    17 Rambling Brook Rd, Chappaqua, NY 10514
  • 200 S Bedford Rd, 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

    Last Listing Agent Annette Cicinelli Keller Williams Realty Partner

    200 S Bedford Rd, Chappaqua, NY 10514
  • 127 Stone Bridge Square Unit 127, Chappaqua, NY 10514
    127 Stone Bridge Square Unit 127, Chappaqua, NY 10514
    127 Stone Bridge Square Unit 127, Chappaqua, NY 10514
    /24

    $799,000

    • 2 Beds
    • 2.5 Baths
    • 1,244 Sq Ft

    127 Stone Bridge Square Unit 127, Chappaqua, NY 10514

    TURNKEY in every way! Beautiful End Unit Townhouse in Old Farm Lake with private wooded views. Spacious Living Room with Wood Burning Fireplace and Cathedral Ceilings. Open Floor Plan with Living Room/Dining Room combination and sliding glass doors out to Deck. Renovated Eat in Kitchen with Carrera Marble counters and Stainless Steel Appliances -- including Bosch Dishwasher, Fisher & Paykel

    Victoria Miller Compass Greater NY, LLC

    127 Stone Bridge Square Unit 127, Chappaqua, NY 10514
  • 45 S Greeley Ave Unit 3, Chappaqua, NY 10514
    45 S Greeley Ave Unit 3, Chappaqua, NY 10514
    45 S Greeley Ave Unit 3, Chappaqua, NY 10514
    /11

    $4,500 Per Month

    • 1 Bed
    • 1 Bath
    • 1,100 Sq Ft
    • Apartment for Rent

    45 S Greeley Ave Unit 3, Chappaqua, NY 10514

    Bright and spacious one-bedroom apartment with an office and den in the heart of downtown Chappaqua. Features a primary bedroom with a walk-in closet, open living and dining area, modern kitchen, full bath, and in-unit laundry. Conveniently located near the train, restaurants, Whole Foods, shops, and schools.

    Holly Tsuei Houlihan Lawrence Inc.

    45 S Greeley Ave Unit 3, Chappaqua, NY 10514
  • 150 N Bedford Rd Unit 6D, 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 $668,685

    Last Listing Agent Sari Shaw Compass Greater NY, LLC

    150 N Bedford Rd Unit 6D, Chappaqua, NY 10514
  • 39 Barnes Ln, Chappaqua, NY 10514
    39 Barnes Ln, Chappaqua, NY 10514
    39 Barnes Ln, Chappaqua, NY 10514
    /8

    $2,895,000

    • 4 Beds
    • 5.5 Baths
    • 4,589 Sq Ft

    39 Barnes Ln, Chappaqua, NY 10514

    Exceptional new construction opportunity in the highly sought-after Chappaqua School District, currently being built with anticipated completion in August 2026. Early buyers will have the rare chance to customize many of the final finishes and tailor the home to their personal style. This thoughtfully designed home offers 4 bedrooms and 5.1 bathrooms, with a highly desirable layout that lives

    Karin Kimtis Compass Greater NY, LLC

    39 Barnes Ln, Chappaqua, NY 10514
  • 343 N Greeley Ave Unit 8D, Chappaqua, NY 10514
    343 N Greeley Ave Unit 8D, Chappaqua, NY 10514
    343 N Greeley Ave Unit 8D, Chappaqua, NY 10514
    /26

    $4,700 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
  • 6 Dewitt Dr Unit 65, Chappaqua, NY 10514

    $1,600,000

    Sold Jul 22, 2025

    6 Dewitt Dr Unit 65, Chappaqua, NY 10514

    • 2 Beds
    • 3.5 Baths
    • 3,353 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $477/SF
    • 66 Days On Market

    Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

    6 Dewitt Dr Unit 65, Chappaqua, NY 10514
  • 25 Longview Ln, Chappaqua, NY 10514
    25 Longview Ln, Chappaqua, NY 10514
    25 Longview Ln, Chappaqua, NY 10514
    /16

    $1,299,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,193 Sq Ft

    25 Longview Ln, Chappaqua, NY 10514

    Tastefully updated and well maintained, this sophisticated yet traditional Contemporary home offers the perfect balance of elegance and comfort in the highly sought-after Chappaqua school district. The light-filled, open floor plan welcomes you with spacious rooms, soaring ceilings, and a floor-to-ceiling stone fireplace anchoring the dramatic great room. The expansive eat-in kitchen is a chef’s

    Cindy Glynn Compass Greater NY, LLC

    25 Longview Ln, Chappaqua, NY 10514
  • 26 Mayberry 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 $1,364,464

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

    26 Mayberry Rd, Chappaqua, NY 10514
  • 2 Turner Dr, Chappaqua, NY 10514
    2 Turner Dr, Chappaqua, NY 10514
    2 Turner Dr, Chappaqua, NY 10514
    /49

    $1,100,000

    • 5 Beds
    • 3 Baths
    • 2,715 Sq Ft

    2 Turner Dr, Chappaqua, NY 10514

    Some homes have good bones. This one has great ones in a private setting. Nestled in Chappaqua's beloved Seven Bridges neighborhood, this 1934 Colonial sits on nearly three-quarters of an acre where tree-lined streets and a true sense of community appeal to buyers who embrace Chappaqua and remain for years. Original hardwood floors, a wood-burning fireplace, crown molding, and a screened porch

    Lauren Zaccaria Houlihan Lawrence Inc.

    2 Turner Dr, Chappaqua, NY 10514
  • 3 Boulder Trail, 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 $2,398,667

    Last Listing Agent Nancy Strong Douglas Elliman Real Estate

    3 Boulder Trail, Chappaqua, NY 10514
  • 40 Kings Ct, Chappaqua, NY 10514
    40 Kings Ct, Chappaqua, NY 10514
    40 Kings Ct, Chappaqua, NY 10514
    /36

    $1,599,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 3,121 Sq Ft

    40 Kings Ct, Chappaqua, NY 10514

    A truly exceptional offering, this picture-perfect 1930s Colonial blends timeless elegance with modern luxury. Set on beautifully landscaped property in a serene setting yet just a moment away from town. Impeccably maintained, tastefully expanded & renovated, the home showcases refined design, effortless flow, and enduring architectural charm.The main level is thoughtfully designed with a

    Jennifer Harris Compass Greater NY, LLC

    40 Kings Ct, Chappaqua, NY 10514
  • 16 Dewitt Dr Unit 70, Chappaqua, NY 10514

    $1,570,856

    Sold Jul 25, 2025

    16 Dewitt Dr Unit 70, Chappaqua, NY 10514

    • 2 Beds
    • 3.5 Baths
    • 3,269 Sq Ft
    • Built 2025

    Last Sold Summary

    • 11% Below List Price
    • $481/SF
    • 323 Days On Market

    Current Estimated Value $1,603,997

    Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

    16 Dewitt Dr Unit 70, Chappaqua, NY 10514
  • 28 Valley View Rd, Chappaqua, NY 10514
    28 Valley View Rd, Chappaqua, NY 10514
    28 Valley View Rd, Chappaqua, NY 10514
    /43

    $1,099,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,999 Sq Ft

    28 Valley View Rd, Chappaqua, NY 10514

    Some homes offer space. Others offer a feeling.Tucked along a picturesque tree lined street in the sought after Dodge Farm section of Chappaqua, 28 Valley View Road is a place where privacy, comfort and timeless charm come together beautifully. Privately sited on approximately 1.2 acres, framed by beautiful landscaping, mature plantings and striking stone walls, this thoughtfully designed 3

    Kile Boga-Ibric Houlihan Lawrence Inc.

    28 Valley View Rd, Chappaqua, NY 10514
  • 106 Random Farms Dr, 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 $1,670,337

    Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

    106 Random Farms Dr, Chappaqua, NY 10514
  • 17 Lila Ln, Chappaqua, NY 10514
    17 Lila Ln, Chappaqua, NY 10514
    17 Lila Ln, Chappaqua, NY 10514
    /23

    $1,590,000

    $35K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,576 Sq Ft

    17 Lila Ln, Chappaqua, NY 10514

    Welcome to this sophisticated carriage home at 17 Lila Lane, offering a rare blend of contemporary luxury and maintenance-free living within the prestigious Chappaqua Crossing community. The thoughtfully designed layout is anchored by a gorgeous chef’s kitchen, featuring a large center island with ample seating and a premium JennAir appliance package. Equally enticing is the coveted first-floor

    Jocelyn Cloder Compass Greater NY, LLC

    17 Lila Ln, Chappaqua, NY 10514
  • 356 N Greeley Ave Unit 28G, 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 $472,834

    Last Listing Agent Alicja Bohmrich Houlihan Lawrence Inc.

    356 N Greeley Ave Unit 28G, Chappaqua, NY 10514
  • 65 Douglas Rd, Chappaqua, NY 10514
    65 Douglas Rd, Chappaqua, NY 10514
    65 Douglas Rd, Chappaqua, NY 10514
    /41

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,702 Sq Ft

    65 Douglas Rd, Chappaqua, NY 10514

    The truly enchanting waterfront setting of this exceptional in-town 1930 Dutch Colonial is defined by sweeping views, lush landscaping, expansive flat yards and a pristine spring-fed duck pond. Meandering stone pathways guide you through beautifully curated grounds, revealing peaceful gathering spaces and quiet corners perfect for enjoying the storybook scenery. Just off the kitchen, a generous

    Lynn Harmonay North Country Sothebys Int Rlt

    65 Douglas Rd, Chappaqua, NY 10514
  • 9 Whitlaw Ln, 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 $1,522,469

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

    9 Whitlaw Ln, Chappaqua, NY 10514
  • 2 Dewitt Dr, Chappaqua, NY 10514
    2 Dewitt Dr, Chappaqua, NY 10514
    2 Dewitt Dr, Chappaqua, NY 10514
    /42

    $1,799,000

    $100K PRICE DROP
    • 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 (lives like a 3BR) and 3.5 baths, thoughtfully designed with high-end finishes and sophisticated upgrades throughout. Expansive windows flood the home with

    Joann Galluccio William Raveis-New York LLC

    2 Dewitt Dr, Chappaqua, NY 10514
  • 4 Carriage Ln Unit 82, 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
    • 16 Kittle Rd, Chappaqua, NY 10514

      Est $2,637,338

      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

  • 22 Random Farms Cir, Chappaqua, NY 10514
    22 Random Farms Cir, Chappaqua, NY 10514
    22 Random Farms Cir, Chappaqua, NY 10514
    /39

    $2,195,000

    Pending
    • 6 Beds
    • 5.5 Baths
    • 6,563 Sq Ft

    22 Random Farms Cir, Chappaqua, NY 10514

    Set on a picturesque property in sought-after Random Farms, this stunning 6-bedroom residence offers dramatic views, soaring ceilings, and exceptional living spaces designed for both everyday comfort and elegant entertaining. A breathtaking double-height entry welcomes you into sun-drenched interiors featuring walls of windows, rich hardwood floors, and seamless open-concept flow

    Sari Shaw Compass Greater NY, LLC

    22 Random Farms Cir, Chappaqua, NY 10514
  • 375 Quaker Rd, 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 $913,324

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

    375 Quaker Rd, Chappaqua, NY 10514

Showing Results 41 - 80, Page 2 of 18

New York Westchester County Chappaqua

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group