4,411

Chappaqua, NY Homes

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  • 12 Pond Hill Rd, Chappaqua, NY 10514
    12 Pond Hill Rd, Chappaqua, NY 10514
    12 Pond Hill Rd, Chappaqua, NY 10514
    /30

    $1,199,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,652 Sq Ft

    12 Pond Hill Rd, Chappaqua, NY 10514

    Picture perfect Cape on level landscaped property with lush lawns radiates curb appeal. Beautifully updated and impeccably maintained with a blend of classic charm and modern luxury. Light-filled rooms with gleaming hardwood floors enhance the well proportioned living spaces. The renovated eat-in kitchen features white cabinetry, stainless steel appliances, quartz countertops and tasteful

    Jennifer Harris Compass Greater NY, LLC

    12 Pond Hill Rd, Chappaqua, NY 10514
  • 26 Dewitt Dr Unit 75, Chappaqua, NY 10514

    $1,631,110 Sold Feb 25, 2025

    • 3,335 Sq Ft
    • $489/SF
    • 5 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    26 Dewitt Dr Unit 75, Chappaqua, NY 10514

    HOME NOT COMPLETED YET- 3 BR Millwood Elite home. This outstanding home is located in the heart of the neighborhood where you can walk to shopping, cafe, gym, pool and more. Includes 3 BR + 2 offices, loft and outdoor terrace w built in grill and linear fireplace and interior wet bar in loft. The open concept great room and kitchen allow for large family gatherings. The open island with

    Thomas Jacovino Toll Brothers Real Estate Inc.

    26 Dewitt Dr Unit 75, Chappaqua, NY 10514
  • 101 Hardscrabble Lake Dr, Chappaqua, NY 10514
    101 Hardscrabble Lake Dr, Chappaqua, NY 10514
    101 Hardscrabble Lake Dr, Chappaqua, NY 10514
    /33

    $1,799,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 4,930 Sq Ft

    101 Hardscrabble Lake Dr, Chappaqua, NY 10514

    Welcome to this spacious 5 Bedrm Colonial on 1.5+ acres in the sought-after Hardscrabble Lake neighborhood. Step inside and you will be delighted throughout -- by the sweeping double staircase, beautiful light Oak flooring, freshly painted interior and so much more. The formal Dining Room and Living Room/Office are graciously-sized, perfect for entertaining. At the heart of the home is an

    Victoria Miller Compass Greater NY, LLC

    101 Hardscrabble Lake Dr, Chappaqua, NY 10514
  • 39 Barnes Ln, Chappaqua, NY 10514

    $425,000 Sold Feb 25, 2025

    • Land
    • 1.06 Acres
    • $400,943 per Acre
    • 87 Days On Market

    39 Barnes Ln, Chappaqua, NY 10514

    ATTENTION BUILDERS! GRAB YOUR HARD HATS! Build your dream home on a desirable cul de sac street in Chappaqua School District! 4 bedroom septic approved! Reach out today for more information!

    Sari Shaw Compass Greater NY, LLC

    39 Barnes Ln, Chappaqua, NY 10514
  • 2 Woodmill Rd, Chappaqua, NY 10514
    2 Woodmill Rd, Chappaqua, NY 10514
    2 Woodmill Rd, Chappaqua, NY 10514
    /49

    $1,075,222 Pending

    • 5 Beds
    • 3.5 Baths
    • 5,227 Sq Ft

    2 Woodmill Rd, Chappaqua, NY 10514

    Spacious Turn-of-the-Century Converted Cider Mill – A True One-of-a-Kind Home! Nestled on just over 1 acre of lush property, this sprawling and unique home was once a cider mill and has been beautifully converted into a spacious residence. Boasting 3 working fireplaces and retaining many of its original architectural details, this home exudes character and charm. With hardwood floors, high wood

    Mark Seiden Mark Seiden Real Estate Team

    2 Woodmill Rd, Chappaqua, NY 10514
  • 4 Timberland Pass, Chappaqua, NY 10514

    $595,000 Sold Feb 21, 2025

    • 1,550 Sq Ft
    • $384/SF
    • 34 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1979

    4 Timberland Pass, Chappaqua, NY 10514

    This home is located in Apple Hill Farm community in Chappaqua NY. This End unit Townhome is located on nice lot with large side and rear property & plenty of privacy. Lots of light with windows galore. This home features 2 bedrooms, with 2.5 baths. A huge living room with cathedral ceilings, a wood burning fireplace and lots of windows. Large formal dining room with sliders to a private patio

    Dorothy Botsoe Dorothy Jensen Realty, Inc.

    4 Timberland Pass, Chappaqua, NY 10514
  • 5 Crossways, Chappaqua, NY 10514
    5 Crossways, Chappaqua, NY 10514
    5 Crossways, Chappaqua, NY 10514
    /22

    $1,099,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,212 Sq Ft

    5 Crossways, Chappaqua, NY 10514

    Move right into this walk-to-town beautifully updated 4-bedroom, 2.5-bath Colonial that offers the perfect balance of classic charm and modern convenience. Just steps from the heart of Chappaqua, this home features an open-concept layout and flexible spaces ideal for everyday living and effortless entertaining.Step through the storybook Dutch door to a light-filled, double-height entry with a

    Jill Urban Compass Greater NY, LLC

    5 Crossways, Chappaqua, NY 10514
  • 7 Deer Run Unit 7, Chappaqua, NY 10514

    $750,000 Sold Feb 18, 2025

    • 1,549 Sq Ft
    • $484/SF
    • 27 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1986

    7 Deer Run Unit 7, Chappaqua, NY 10514

    Step into luxury - in this fully renovated condo in Chappaqua at Old Farm Lake development, close to town, train, shops and schools. Enter the foyer with marble floors, leading to the kitchen with Bosch stainless appliances and walk out to front patio. The dining room opens to a spacious living room with a vaulted high ceiling with skylights and decorated with hardwood, complete with a stunning

    Natalia Wixom Compass Greater NY, LLC

    7 Deer Run Unit 7, Chappaqua, NY 10514
  • 8 Turtleback Way, Chappaqua, NY 10514
    8 Turtleback Way, Chappaqua, NY 10514
    8 Turtleback Way, Chappaqua, NY 10514
    /50

    $2,485,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 6,649 Sq Ft

    8 Turtleback Way, Chappaqua, NY 10514

    Introducing a luxurious lifestyle at 8 Turtleback Way in the prestigious Hardscrabble Lake Community of Chappaqua. This private neighborhood graced with delightful lakes is perfect for peaceful strolls and getting in your daily steps. It also offers the convenience of door-to-door school bus service within the top-rated Chappaqua School District. Nestled on a magnificent 1.24-acre lot, this 6,649

    Michele Iasich-Pagnotta Houlihan & O'Malley R. E. Serv

    8 Turtleback Way, Chappaqua, NY 10514
  • 40 Aldridge Rd, Chappaqua, NY 10514

    $1,955,000 Sold Feb 04, 2025

    • 3,541 Sq Ft
    • $552/SF
    • 8 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1955

    40 Aldridge Rd, Chappaqua, NY 10514

    Move right in to this beautiful home perfectly situated on a tranquil cul-de-sac, offering the best of both worlds: a spacious, private retreat with the convenience of being close to town and train. This airy & bright 4-bedroom, 4-bathroom home is designed for both comfort & elegance. Discover a first-floor primary bedroom with soaring ceilings & a generous walk-in closet. The heart of the home

    Jodi Greebel Compass Greater NY, LLC

    40 Aldridge Rd, Chappaqua, NY 10514
  • 1 West Place, Chappaqua, NY 10514
    1 West Place, Chappaqua, NY 10514
    1 West Place, Chappaqua, NY 10514
    /43

    $1,799,000 Pending

    • 3 Beds
    • 3.5 Baths
    • 3,176 Sq Ft

    1 West Place, Chappaqua, NY 10514

    Welcome to this meticulously maintained home nestled in the heart of Hillholme, an idyllic and sought after neighborhood minutes to Chappaqua town, train and schools. Thoughtfully expanded by noted architect Carol Kurth, this spectacular three bedroom home (lives like a five bedroom), exudes timeless elegance with superior quality throughout. The first floor boasts an expanded foyer, formal

    Jennifer Harris Compass Greater NY, LLC

    1 West Place, Chappaqua, NY 10514
  • 55 Florence Dr, Chappaqua, NY 10514

    $2,275,000 Sold Jan 31, 2025

    • 2,984 Sq Ft
    • $762/SF
    • 4 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1978

    55 Florence Dr, Chappaqua, NY 10514

    Spectacular Mid-Century modern completely renovated and privately set on 2.23 gorgeous park-like acres at the end of a neighborhood cul-de-sac featuring stone walls, professional landscaping, perennial& vegetable gardens, specimen plantings & towering old growth trees for complete privacy, yet close to all. Expansive deck, soaring ceilings throughout, open plan, walls of glass & abundant natural

    Sena Baron William Raveis-New York, LLC

    55 Florence Dr, Chappaqua, NY 10514
  • 8 Elizabeth St, Chappaqua, NY 10514
    8 Elizabeth St, Chappaqua, NY 10514
    8 Elizabeth St, Chappaqua, NY 10514
    /33

    $999,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    8 Elizabeth St, Chappaqua, NY 10514

    Welcome to 8 Elizabeth Street – A Charming, Turnkey Colonial nestled on a quiet cul-de-sac street. A beautifully updated three-bedroom, two-and-a-half-bathroom Colonial that seamlessly blends style, comfort, and convenience. Step inside to discover a thoughtfully designed layout, where large, updated windows flood the home with natural light. The spacious living room is an inviting gathering

    Jennifer Harris Compass Greater NY, LLC

    8 Elizabeth St, Chappaqua, NY 10514
  • 32 Begg Dr, Chappaqua, NY 10514

    $999,999 Sold Jan 30, 2025

    • 1,657 Sq Ft
    • $603/SF
    • 20 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1927

    32 Begg Dr, Chappaqua, NY 10514

    Step into the timeless charm of this captivating colonial located on a sought-after tree-lined cul-de-sac. This move-in-ready home offers an open floor plan with abundant windows, creating a bright and welcoming atmosphere. The stunning living room/great room features a fireplace, elegant columns, detailed moldings, recessed lighting, and walls of windows, flooding the space with natural light.

    Wendy Nolan Houlihan Lawrence Inc.

    32 Begg Dr, Chappaqua, NY 10514
  • 180 Millwood Rd, Chappaqua, NY 10514
    180 Millwood Rd, Chappaqua, NY 10514
    180 Millwood Rd, Chappaqua, NY 10514
    /29

    $879,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,334 Sq Ft

    180 Millwood Rd, Chappaqua, NY 10514

    Welcome to a home full of warmth, charm, and everyday comfort — perfectly situated right across from beautiful Gedney Park and just around the corner from the elementary school.This inviting 4-bedroom, 2.5-bathroom home has everything you need for easy, relaxed living. Step inside to a bright and welcoming living room, a private office ideal for working from home, and a comfortable family

    Danae Richards William Raveis-New York, LLC

    180 Millwood Rd, Chappaqua, NY 10514
  • 33 Chatham Rd, Chappaqua, NY 10514

    $1,175,000 Sold Jan 24, 2025

    • 2,100 Sq Ft
    • $560/SF
    • 18 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1942

    33 Chatham Rd, Chappaqua, NY 10514

    Beautifully renovated home 3 bedroom 2.5 bath on 1.3 acres in Chappaqua Ridge community. With its classic center hall colonial layout and beautiful renovations, it's perfect for someone looking for both charm and modern updates. New kitchen with deck overlooking private yard Is ideal for entertaining, oversized Livingroom with wood burning fireplace, formal Dining Room, Primary suite , along

    Phyllis Lerner Corcoran Legends Realty

    33 Chatham Rd, Chappaqua, NY 10514
  • 42 Seven Bridges Rd, Chappaqua, NY 10514
    42 Seven Bridges Rd, Chappaqua, NY 10514
    42 Seven Bridges Rd, Chappaqua, NY 10514
    /49

    $1,799,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 4,561 Sq Ft

    42 Seven Bridges Rd, Chappaqua, NY 10514

    Featured in Westchester magazine’s “Best Places to Live 2016” as an outstanding example of a Federal style colonial residence, this one-of-a-kind classic offers architectural integrity combined w impeccable present day renovations & amenities. This 5BR/3.1Bth colonial offers center hall layout, multiple fireplaces, exposed hand hewn beamed ceilings, post & beam construction in upper level, wide

    Sena Baron William Raveis-New York, LLC

    42 Seven Bridges Rd, Chappaqua, NY 10514
  • 140 S Bedford Rd, Chappaqua, NY 10514

    $1,550,000 Sold Jan 23, 2025

    • 3,631 Sq Ft
    • $427/SF
    • 17 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2004

    140 S Bedford Rd, Chappaqua, NY 10514

    Modern Colonial, nestled on a private 1.23 acre lot in the Chappaqua School District. This 4 bedroom, 3,631 sq ft open flow, expansive home is thoughtfully crafted, featuring generously sized light-filled rooms with large windows and essential amenities. A double height entry foyer with chandelier opens to formal spaces, an office/guest room, formal dining and living rooms. This comfortable, open

    Cindy Glynn Compass Greater NY, LLC

    140 S Bedford Rd, Chappaqua, NY 10514
  • 13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514
    13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514
    13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514
    /4

    $1,399,995 Pending

    • 2 Beds
    • 3.5 Baths
    • 2,945 Sq Ft

    13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514

    2 BR Primary on first floor home. Large Eat in kitchen with island, open to great room and dining room. Second floor office and wet bar makes entertaining easy on rooftop terrace with built-in kitchen BBQ. Lower level is finished with media room and full bath.

    Thomas Jacovino Toll Brothers Real Estate Inc.

    13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514
  • 41 Lila Ln Unit 60, Chappaqua, NY 10514

    $1,624,375 Sold Jan 21, 2025

    • 3,101 Sq Ft
    • $524/SF
    • 117 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2023

    41 Lila Ln Unit 60, Chappaqua, NY 10514

    CONSTRUCTION TO BEGIN SOON ON THIS HOME:2 BR Greeley Floorplan with primary on first floor. An elevator is included as well as a finished basement with full bath, wet bar in 2nd floor loft and open railings to lower level, car charger and teak pavers on the terrace. This outstanding home is located in a private area of the community but still allows owners to walk to shopping,

    Thomas Jacovino Toll Brothers Real Estate Inc.

    41 Lila Ln Unit 60, Chappaqua, NY 10514
  • 45 Crossways, Chappaqua, NY 10514
    45 Crossways, Chappaqua, NY 10514
    45 Crossways, Chappaqua, NY 10514
    /36

    $1,200,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,246 Sq Ft

    45 Crossways, Chappaqua, NY 10514

    Storybook 1930’s-era Tudor-style shingle cottage delightfully renovated & updated with all the comforts for the 21st century. Believed to be originally derived from Standard Homes Co. classic Densmore model. A welcoming entry vestibule with French door introduces a wide, front-facing living room, warmed by a stout wood-burning fireplace. Gather together in the dining room to enjoy holiday feasts

    Stacy Levey William Raveis-New York, LLC

    45 Crossways, Chappaqua, NY 10514
  • 14 Alta Ln, Chappaqua, NY 10514

    $1,600,000 Sold Jan 21, 2025

    • 5,111 Sq Ft
    • $313/SF
    • 48 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 1979

    14 Alta Ln, Chappaqua, NY 10514

    Mid-century modern home lovers will appreciate this 1979 contemporary, designed by Chappaqua architect, Charles Napoli as an homage to Frank Lloyd Wright. Set on 1.35 acres, this 5 BR, 5.1 BA home has walls of windows showcasing the lush property and mature trees. The open plan of the house flows naturally with a grand, open living rm to dining and eat-in kitchen w/ sliders to patio. The great

    Stacey Rechler Douglas Elliman Real Estate

    14 Alta Ln, Chappaqua, NY 10514
  • 74 Seven Bridges Rd, Chappaqua, NY 10514
    74 Seven Bridges Rd, Chappaqua, NY 10514
    74 Seven Bridges Rd, Chappaqua, NY 10514
    /26

    $989,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,018 Sq Ft

    74 Seven Bridges Rd, Chappaqua, NY 10514

    Welcome to 74 Seven Bridges Road in Chappaqua—a home that perfectly blends comfort and style.This inviting home features an open floor plan designed for effortless living and entertaining. Enter into a large foyer with a smart mud room tucked away to the side. Here you also have direct and easy access to the garage. Once inside you will appreciate the warmth and sophistication this home

    Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

    74 Seven Bridges Rd, Chappaqua, NY 10514
  • 54 Spring Rd, Chappaqua, NY 10514

    $1,150,000 Sold Jan 15, 2025

    • 2,482 Sq Ft
    • $463/SF
    • 41 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1935

    54 Spring Rd, Chappaqua, NY 10514

    Set on a quiet street just a few minutes from Chappaqua town center, this charming colonial with effortlessly blends historical character with modern updates. The home showcases original arts & crafts and architectural features - exposed beams, wood trim, and beautifully refinished hardwood floors throughout. Handmade Motawi tiles adorn fireplace. The high-end kitchen, with custom Bilotta

    Natalia Wixom Compass Greater NY, LLC

    54 Spring Rd, Chappaqua, NY 10514
  • 14 Carriage Ln Unit 87, Chappaqua, NY 10514
    14 Carriage Ln Unit 87, Chappaqua, NY 10514
    14 Carriage Ln Unit 87, Chappaqua, NY 10514
    /4

    $1,338,995 Pending

    • 2 Beds
    • 2.5 Baths
    • 2,503 Sq Ft

    14 Carriage Ln Unit 87, Chappaqua, NY 10514

    HOME IS UNDER CONSTRUCTION- READY FOR Summer 2025 closing 2 BR Briarcliff Floorplan with primary on first floor. You can still add structural and design features to this home. This outstanding home is located in a great location facing greenspace on one side and forest views from the rooftop deck. It is located in the heart of the neighborhood where you can walk to shopping, cafes,

    Thomas Jacovino Toll Brothers Real Estate Inc.

    14 Carriage Ln Unit 87, Chappaqua, NY 10514
  • 3 High Point Cir, Chappaqua, NY 10514

    $1,700,214 Sold Jan 10, 2025

    • 3,421 Sq Ft
    • $497/SF
    • 9 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1955

    3 High Point Cir, Chappaqua, NY 10514

    Welcome to 3 High Point Circle! This delightful home features 4 spacious bedrooms + 3.5 bathrooms, all set on a beautifully landscaped, fenced-in, 1-acre lot on a sought after cul-de-sac. Inside, you'll love the open floor plan, perfect for entertaining and the spacious family room for relaxation. The Primary suite boasts a newly renovated bathroom and a spacious walk-in closet. The lower level

    Debra Goldenberg Compass Greater NY, LLC

    3 High Point Cir, Chappaqua, NY 10514

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