23

Homes for Sale in 10514

Section Image Section Image
  • /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

    Agent Photo

    Donna McKenna Edlund

    Coldwell Banker Realty

    (914) 537-3558

    368 N Greeley Ave Unit 34G, 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
  • /41

    $2,599,000

    • 4 Beds
    • 3.5 Baths
    • 3,523 Sq Ft

    14 Annandale Rd, Chappaqua, NY 10514

    Nestled in the heart of the coveted Lawrence Farms East neighborhood, 14 Annandale Road is a rare offering that seamlessly blends timeless sophistication with modern comfort on one of Chappaqua’s most desirable streets. Set on beautifully manicured, park-like grounds, this classic four-bedroom residence exudes understated elegance from the moment you arrive. A gracious approach leads to a

    Sari Shaw Compass Greater NY, LLC

    14 Annandale Rd, Chappaqua, NY 10514
  • /17

    $3,350,000

    • 4 Beds
    • 7 Baths
    • 5,712 Sq Ft

    201 Bedford Rd, Chappaqua, NY 10514

    Exciting all new construction by highly regarded local builder, Tavo Development, along with noted architect Teo Siguenza, aiming for a Fall 2026 completion. This refined, 5,712 sq ft Colonial blends classic architecture with sophisticated modern living. The light-filled main level, with 10’ ceilings, offers a seamless open floorplan featuring a chef’s kitchen with island and service pantry,

    Brian Milton Compass Greater NY, LLC

    201 Bedford Rd, Chappaqua, NY 10514
  • /49

    $2,350,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 5 Baths
    • 4,385 Sq Ft

    790 King St, Chappaqua, NY 10514

    A Rare Opportunity Where History Meets Modern Living.Built in 1750 and thoughtfully renovated in 2005. White clapboard, black shutters, cedar shake roof, and copper gutters set a timeless exterior, framed by professionally designed grounds.A wide entry hall opens to living and dining rooms bookended by floor-to-ceiling stone fireplaces. Hardwood floors and detailed millwork mark the

    Harriet Libov Houlihan Lawrence Inc.

    790 King St, Chappaqua, NY 10514
  • /43

    $2,499,000

    Open Sun 1:30PM - 3PM
    • 3 Beds
    • 4 Baths
    • 6,115 Sq Ft

    33 Greenbriar Dr, Chappaqua, NY 10514

    Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods, this exceptional luxury Colonial blends timeless architecture, designer finishes, and an unmatched indoor-outdoor lifestyle within the award-winning Chappaqua school district. Privately positioned against acres of preserved land, this premier Westchester County property offers both tranquility and convenience,

    Wendy Nolan Houlihan Lawrence Inc.

    33 Greenbriar Dr, Chappaqua, NY 10514
  • /35

    $2,990,000

    $687K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 8,200 Sq Ft

    20 Bessel Ln, Chappaqua, NY 10514

    Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides

    Tianying Xu Houlihan Lawrence Inc.

    20 Bessel Ln, Chappaqua, NY 10514
  • /41

    $2,250,000

    Open Sat 12PM - 3PM
    • 5 Beds
    • 4.5 Baths
    • 4,594 Sq Ft

    630 Chappaqua Rd, Briarcliff Manor, NY 10510

    Beautifully renovated and exceptionally private, this impressive Colonial is set on over 8 acres surrounded by mature trees, offering a peaceful retreat just minutes from town, Metro-North train service, shopping, dining, and all within the highly sought-after Chappaqua School District. Completely renovated between 2021–2022 with stylish, high-end finishes throughout, this expansive 5-bedroom,

    Karin Kimtis Compass Greater NY, LLC

    630 Chappaqua Rd, Briarcliff Manor, NY 10510
  • /32

    $2,285,000

    • 5 Beds
    • 5.5 Baths
    • 6,108 Sq Ft

    16 Carolyn Place, Armonk, NY 10504

    Introducing an exceptional offering in the prestigious Whippoorwill neighborhood of Armonk. Privately set on 2 beautiful landscaped acres, this expansive residence offers over 6,000 square feet of refined living space and the flexibility of a 5 bedroom home that lives like a 6 bedroom. Designed for both entertaining and comfortable living, the sun-drenched, renovated chef’s kitchen opens

    Amy Singer Houlihan Lawrence Inc.

    16 Carolyn Place, Armonk, NY 10504
  • /26

    $1,095,000

    • 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
  • /45

    $1,395,000

    Open Sun 10AM - 12PM
    • 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
  • /23

    $1,625,000

    • 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
  • /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
  • /41

    $1,600,000

    • 4 Beds
    • 3.5 Baths
    • 3,138 Sq Ft

    14 Crossways, Chappaqua, NY 10514

    Most “walk-to-town” homes ask you to compromise on space, privacy, or both. At 14 Crossways, you get all three. Set less than a mile from the Chappaqua station, it combines true walkability with more than 3,100 square feet of well-organized living space on a private, level half-acre. Carefully maintained and thoughtfully improved, it is also a house designed for entertaining. At its center, the

    Jonathan Cape Julia B Fee Sothebys Int. Rlty

    14 Crossways, Chappaqua, NY 10514
  • /6

    $639,000

    • Land
    • 7,405 Sq Ft
    • $3,758,824 per Acre

    65 S Bedford Rd, Chappaqua, NY 10514

    A rare opportunity to build mixed use consisting of commercial/professional and multi-family with huge income potential.The 1st floor as commercial and the 2nd and 3rd floors residential apartments.An architect has drawn 4 concept plans ranging from commercial space and lobby with (4) 2-bedroom apartments to commercial space and lobby with (6) 1-bedroom apartments.One example:1st

    Theodore Weinstein REO Edge LLC

    65 S Bedford Rd, Chappaqua, NY 10514
  • /36

    $1,299,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 3 Baths
    • 2,444 Sq Ft

    816 Hardscrabble Rd, Chappaqua, NY 10514

    Just north of NYC, this move-in ready CHAPPAQUA home delivers effortless, elevated living—done RIGHT.3 min drive to Metro North station - 48 min ride to Grand Central Station * Set behind a long private driveway with an attached 2-car garage and expansive front yard, the property captures stunning sunset views, with golden hour pouring in the best way. Inside captures a calm, grounded palette

    Bianca Siani eXp Realty

    816 Hardscrabble Rd, Chappaqua, NY 10514
  • /27

    $2,600,000

    • 6 Beds
    • 4 Baths
    • 4,233 Sq Ft

    82 Douglas Rd, Chappaqua, NY 10514

    UNIQUE HIGH-NET INVESTMENT OPPORTUNITY IN CHAPPAQUA SCHOOLS - 5 MIN WALK TO TRAIN. LIVE IN ONE UNIT AND COLLECT INCOME FROM TWO UNITS. LEGAL THREE-FAMILY PROPERTY WITH ONE SINGLE-FAMILY 2BR/2BA RESIDENCE AND A TWO-FAMILY (4BR/2BA) RESIDENCE. HIGH RENTS - $167K ANNUAL GROSS/ $135K NET. ALL UNITS CURRENTLY RENTED BUT TWO OF THREE UNITS EXPIRE 7/31/26, SO THERE IS FLEXIBILITY. SINGLE FAMILY TENANT

    Kristen Renzulli Arch & Gable Realty LLC

    82 Douglas Rd, Chappaqua, NY 10514
  • /48

    $4,500,000

    • 5 Beds
    • 7 Baths
    • 7,608 Sq Ft

    150 Old Farm Rd N, Chappaqua, NY 10514

    1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original

    Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

    150 Old Farm Rd N, Chappaqua, NY 10514
  • /14

    $1,750,000

    • Land
    • 12.92 Acres
    • $135,449 per Acre

    767 King St, Chappaqua, NY 10514

    Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park,

    Sena Baron William Raveis-New York, LLC

    767 King St, Chappaqua, NY 10514
  • /50

    $1,200,000

    $149K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,112 Sq Ft

    335 Roaring Brook Rd, Chappaqua, NY 10514

    "VICTORIAN SPLENDOR" - A unique opportunity to own an early Grand Victorian home on park-like property with 3 fireplaces, a pool and a barn.Designated a New Castle George Carpenter Historic Landmark dating back to 1780. As you enter the main entrance a flood of natural light welcome you. The two-story projection of the façade’s central section, rising to a peak at the roofline, along

    Alicja Bohmrich Houlihan Lawrence Inc.

    335 Roaring Brook Rd, Chappaqua, NY 10514
  • /30

    $829,000

    Open Sat 11AM - 12PM
    • 4 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    73 S Bedford Rd, Chappaqua, NY 10514

    Welcome home to this well-maintained residence in the heart of vibrant Chappaqua! This 4 bedroom and 2.5 full bathroom house is located in the award-winning Chappaqua school district. Step inside to discover gleaming hardwood floors throughout, a cozy living room with a wood-burning fireplace, and a bright, charming dining room. The kitchen features ample cabinetry, granite countertops, and

    Thomas Hennerty

    73 S Bedford Rd, Chappaqua, NY 10514
  • /33

    $899,000

    • 4 Beds
    • 2 Baths
    • 2,100 Sq Ft

    249 Mill River Rd, Chappaqua, NY 10514

    Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed for both everyday

    Harry Donofrio Town and Village Real Estate

    249 Mill River Rd, Chappaqua, NY 10514
  • /17

    $569,000

    $30K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 924 Sq Ft

    150 Bedford Rd Unit 12A, Chappaqua, NY 10514

    Welcome to this move-in-ready 2-bedroom, 2-bath residence in highly sought-after Chappaqua Commons. Recently refreshed with thoughtful updates throughout, this sun-filled home combines modern finishes with effortless convenience.The spacious open-concept living and dining area features brand-new flooring (2025) and a seamless flow to the updated kitchen, boasting new countertops and

    Sari Shaw Compass Greater NY, LLC

    150 Bedford Rd Unit 12A, Chappaqua, NY 10514
How to Buy a Home How to Finance a Home How to Sell a Home