Homes in ZIP Code 10514

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  /32

  $1,495,000

  • 5 Beds
  • 3.5 Baths
  • 4,400 Sq Ft

  250 New York 100, Mount Kisco, NY 10549

  This stately Second Empire Victorian, built in the late 1800's, proudly sits on over 11 acres of land and is characterized by its grand style, distinctive mansard roof and rich garnishment. A unique and special home that blends historic charm with classic elegance. When you drive onto the property, the mere sight of this special home will take your breath away! It's tall, stately,

  

  Loretta Fleming Chiavetta

  Coldwell Banker Realty

  (914) 647-4584

  250 New York 100, Mount Kisco, NY 10549
• 

  

  

  /14

  $4,050 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Townhouse for Rent

  7 Valley View Rd Unit 1, Chappaqua, NY 10514

  This is a rare and unique short-term rental opportunity at a below market rate of $4,050/month from November 2, 2025 - June 30, 2026. This one-time opportunity to lease a 2 bed/2 bath cottage in Chappaqua proper is being offered because the current tenant needs to move out before the current lease expires. Starting July 1, 2026, at landlord’s discretion, a new 12-month lease may be offered at no

  

  Deena Bouchier

  Compass Greater NY, LLC

  (914) 594-5450

  7 Valley View Rd Unit 1, Chappaqua, NY 10514
• 

  $525,000 Sold Oct 16, 2025

  • 880 Sq Ft
  • $597/SF
  • 61 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1927

  380 Whippoorwill Rd, Chappaqua, NY 10514

  This charming cottage has been completely reimagined, seamlessly blending timeless character with modern luxury. Fully gut-renovated and thoughtfully redesigned from top to bottom, this inviting home offers the perfect retreat—whether you're seeking a serene weekend escape or a full-time residence.Ideally located just minutes from downtown Chappaqua and seconds from Chappaqua Crossing, Horace

  Sari Shaw Compass Greater NY, LLC

  380 Whippoorwill Rd, Chappaqua, NY 10514
• 

  Est $1,214,306 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,995 Sq Ft

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514
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  /32

  $1,500,000

  • 4 Beds
  • 2.5 Baths
  • 2,891 Sq Ft

  7 Byram Meadows Rd, Chappaqua, NY 10514

  Welcome to this beautifully maintained home featuring a spacious 476 sq ft sunroom with direct access from both the living room and family room—ideal for year-round enjoyment. Recent updates include a new roof (2023), new central air unit (2022), and all new water and heating systems in the basement, offering peace of mind and modern efficiency. The family room boasts a classic wood-burning

  Ken Wile Redfin Real Estate

  7 Byram Meadows Rd, Chappaqua, NY 10514
• 

  

  /25

  $2,200 - $6,350 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
• 

  $1,075,000 Sold Oct 10, 2025

  • 2,447 Sq Ft
  • $439/SF
  • 48 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1981

  21 Kipp St, Chappaqua, NY 10514

  Step into this beautifully updated 4-bedroom, 2.5-bathroom home, just a short stroll from the vibrant shops, dining, and charm of downtown Chappaqua. Perfectly situated for an easy city commute, this home offers the ideal blend of convenience and tranquility. Inside, you'll find generously sized rooms filled with natural light. The serene primary suite provides a peaceful retreat at the end of

  Vanessa Catalano Julia B Fee Sothebys Int. Rlty

  21 Kipp St, Chappaqua, NY 10514
• 

  Est $1,753,825 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,700 Sq Ft

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514
• 

  

  /49

  $2,200,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,172 Sq Ft

  77 Haights Cross Rd, Chappaqua, NY 10514

  Timeless elegance meets modern comfort in this enchanting 1901 hunting lodge, masterfully restored in 1991 and recently enhanced. Set on beautifully landscaped grounds with lush gardens, this distinguished home features a dramatic front portico, high ceilings, intricate millwork, and unique architectural details throughout. Grand living spaces include a library/home office with French doors and

  Joshua Rogull Julia B Fee Sothebys Int. Rlty

  77 Haights Cross Rd, Chappaqua, NY 10514
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  /26

  $8,500 per month

  • 4 Beds
  • 3 Baths
  • 3,141 Sq Ft
  • House for Rent

  49 Commodore Rd, Chappaqua, NY 10514

  Picture perfect center hall colonial. Ideal executive rental, walk to town and train. Living room with fireplace, dining room with sliders to large deck, and modern eat-in kitchen. Bedroom and full bath on first level, perfect for au-pair or guest suite. Primary bedroom with en-suite bath, featuring double sink vanity, jacuzzi tub and stand alone shower. Two more hall bedrooms, well-appointed

  Gail Silverstein ERA Insite Realty Services

  49 Commodore Rd, Chappaqua, NY 10514
• 

  $1,800,000 Sold Oct 09, 2025

  • 5,089 Sq Ft
  • $354/SF
  • 15 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1991

  73 Random Farms Dr, Chappaqua, NY 10514

  Stately and Inviting, with a rocking chair front porch, this beautifully landscaped Post-Modern Colonial sitting on .73 acres is up for sale in the highly sought-after Random Farms Community. On a lush, level property framed with shade trees, this extraordinary house is beautifully designed and laid out. Enter this 5-bedroom 4.5 bath wonder through a light-filled double height foyer featuring

  Alicja Bohmrich Houlihan Lawrence Inc.

  73 Random Farms Dr, Chappaqua, NY 10514
• 

  Est $1,501,345 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,811 Sq Ft

  265 Mill River Rd, Chappaqua, NY 10514

  265 Mill River Rd, Chappaqua, NY 10514
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  /48

  $1,999,999

  • 3 Beds
  • 4.5 Baths
  • 3,880 Sq Ft

  19 Stony Hollow, Chappaqua, NY 10514

  Living like a four-bedroom, this gracious and spacious three-bedroom plus bonus room modern Colonial shines from top to bottom from the meticulous maintenance and updates by the original owners. A welcoming, grand two-story entry introduces a large formal living room brightly illuminated by large front- and side-facing windows, recessed lighting and a wood-burning fireplace. French doors add

  Stacy Levey William Raveis-New York, LLC

  19 Stony Hollow, Chappaqua, NY 10514
• 

  

  /39

  $7,500 per month

  • 3 Beds
  • 3.5 Baths
  • 4,780 Sq Ft
  • House for Rent

  790 Hardscrabble Rd, Chappaqua, NY 10514

  A Rare Blend of Timeless Charm & Modern Luxury in the Heart of Chappaqua Step back in time while indulging in the comforts of today in this exquisitely reimagined Stately Colonial, nestled within the prestigious Chappaqua School District. A captivating residence where old-world elegance meets contemporary sophistication. From the moment you arrive, the home's striking presence is undeniable. A

  Kile Boga-Ibric Houlihan Lawrence Inc.

  790 Hardscrabble Rd, Chappaqua, NY 10514
• 

  $2,300,000 Sold Oct 08, 2025

  • 5,183 Sq Ft
  • $444/SF
  • 91 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2000

  3 Boulder Trail, Chappaqua, NY 10514

  Turn-key, custom-built 5-bedroom center-hall colonial in Chappaqua’s desirable Hardscrabble Lake community. First floor includes an open floor plan between the updated kitchen and family room with wood-burning fireplace and sliders to the oversized, new Trex deck, a large living room with french doors to the library with access to the deck, formal dining room, powder room, mudroom and door to

  Nancy Strong Douglas Elliman Real Estate

  3 Boulder Trail, Chappaqua, NY 10514
• 

  Est $817,558 Not Listed For Sale

  70 Leroy Rd, Chappaqua, NY 10514

  70 Leroy Rd, Chappaqua, NY 10514
• 

  

  /39

  $1,450,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft

  71 Commodore Rd, Chappaqua, NY 10514

  Perfectly positioned on a serene and private 1.72 parcel in the sought-after, coveted Commodore Road neighborhood, this classic ranch-style home offers incredible potential just minutes from Chappaqua village, train, shops, and schools. Surrounded by mature trees, natural rock outcroppings, and a level backyard, this beautifully sited property with a majestic long driveway, is a rare

  Cindy Glynn Compass Greater NY, LLC

  71 Commodore Rd, Chappaqua, NY 10514
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  /12

  $2,800 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  205 N Greeley Ave Unit A, Chappaqua, NY 10514

  Two-bedroom, one-level unit with private entrance and short walk to train, restaurants, and shopping in the Village of Chappaqua, NY. Private laundry in the unit. Two large bedrooms. Private parking in the driveway for up to 2 cars. Water is included in the monthly rent.

  Edward Holmes William Raveis-New York, LLC

  205 N Greeley Ave Unit A, Chappaqua, NY 10514
• 

  $1,275,000 Sold Oct 06, 2025

  • 2,111 Sq Ft
  • $604/SF
  • 60 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1952

  4 Southview Rd, Chappaqua, NY 10514

  Fabulous 3 Bedroom Home which lives like 4 Bedroom on rare and lovely cul-de-sac within a 5-minute walk to the nationally ranked Horace Greeley High School, part of the award-winning Chappaqua School District, and to Chappaqua Crossing with its charming shops and restaurants, including Whole Foods, Life Time Gym, Starbucks, and the Chappaqua Performing Arts Center. It is also in close proximity

  Wendy Nolan Houlihan Lawrence Inc.

  4 Southview Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 4 Beds

  767 King St, Chappaqua, NY 10514

  767 King St, Chappaqua, NY 10514
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  /34

  $1,850,000 Open Sun 1PM - 2PM

  • 5 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  675 Quaker Rd, Chappaqua, NY 10514

  Stunning and elegant 5 bedroom/5.5 baths ranch style home plus detached garage studio with full bath and kitchenette. Luxuriously appointed. Custom millwork featured in every room. Open floor plan, living room with marble floors, fireplace surrounded by built-in shelving with adjacent dining room with built-in cabinetry and buffet. Custom kitchen with oversized marble island, custom cabinetry and

  Margaret Harrington Douglas Elliman Real Estate

  675 Quaker Rd, Chappaqua, NY 10514
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  /28

  $4,400 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  547 King St Unit B, Chappaqua, NY 10514

  Move right in to this freshly painted home with a beautifully renovated eat-in kitchen and new flooring. High ceilings add to the open feel, offering 2 bedrooms, 1 full bath, plus a versatile den/office. Perfectly located close to town, shops, restaurants, train, bus, and major routes — a blend of comfort and convenience!

  Patricia DelVecchio William Raveis Real Estate

  547 King St Unit B, Chappaqua, NY 10514
• 

  $1,660,000 Sold Oct 03, 2025

  • 5,357 Sq Ft
  • $310/SF
  • 25 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1993

  43 Random Farms Cir, Chappaqua, NY 10514

  Discover the most private home in the prestigious Random Farms community of Chappaqua, NY. Tucked away amid lush, mature landscaping, this stunning five-bedroom contemporary colonial offers a rare sense of natural seclusion and tranquility. Enjoy the ultimate in privacy without sacrificing convenience—just a short stroll to the neighborhood pool, clubhouse, and tennis courts. This exceptional

  Suzan Zeolla Houlihan Lawrence Inc.

  43 Random Farms Cir, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  9 McKesson Hill Rd, Chappaqua, NY 10514

  9 McKesson Hill Rd, Chappaqua, NY 10514
• 

  

  /33

  $1,850,000

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

  24 North Way, Chappaqua, NY 10514

  A/O-10/13-Move-in ready, light and bright 3 bedroom/ 3.5 bathroom home that can live like a 5 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

  Pamela Akin Douglas Elliman Real Estate

  24 North Way, Chappaqua, NY 10514
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  /21

  $6,250 per month

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft
  • House for Rent

  235 Douglas Rd, Chappaqua, NY 10514

  This beautifully updated rental offers a bright, open layout and a prime location just under a mile from downtown Chappaqua and the Metro North station—perfect for easy commuting and enjoying all the local spots. Freshly painted and move-in ready, the home is available furnished or unfurnished.The main level features a sun-filled living and dining area, an updated kitchen, a spacious

  Danielle Della Pella Compass Greater NY, LLC

  235 Douglas Rd, Chappaqua, NY 10514
• 

  $1,275,000 Sold Oct 03, 2025

  • 3,200 Sq Ft
  • $398/SF
  • 85 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1964

  26 Mayberry Rd, Chappaqua, NY 10514

  Welcome to 26 Mayberry Road, a charming and spacious 5-bedroom expanded ranch-style home on a quiet cul-de-sac street in the Chappaqua school district. Set on a private, landscaped acre, this home offers scenic views from the elevated deck and large stone patio just off the walkout lower level. The main floor features a versatile and inviting layout with formal living and dining rooms, a kitchen

  Edward Holmes William Raveis-New York, LLC

  26 Mayberry Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 4,692 Sq Ft

  219 Hamilton Rd, Chappaqua, NY 10514

  219 Hamilton Rd, Chappaqua, NY 10514
• 

  

  /26

  $1,650,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,244 Sq Ft

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514

  Welcome to this sophisticated 4-bedroom, 3.5-bath contemporary residence, perfectly designed for today’s lifestyle with a seamless blend of modern style and functional comfort. Set on a gracious property, this home offers open, luminous living spaces flooded with natural light and thoughtful architectural detail throughout. At the heart of the home, a beautifully appointed kitchen opens to a

  Sari Shaw Compass Greater NY, LLC

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514
• 

  

  /35

  $5,400 per month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  25 Maple Ave, Chappaqua, NY 10514

  Charming 3-Bedroom, 2-Bath Home in the Heart of Chappaqua!Welcome to this beautifully updated home located just steps from the train, shops, schools, and restaurants in vibrant downtown Chappaqua. This move-in ready residence features three spacious bedrooms and two full bathrooms, perfect for comfortable family living.Recent upgrades include fresh interior paint, new

  Heidi Oliver Houlihan Lawrence Inc.

  25 Maple Ave, Chappaqua, NY 10514
• 

  $1,375,000 Sold Oct 01, 2025

  • 2,195 Sq Ft
  • $626/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1937

  4 Oak Hill Rd, Chappaqua, NY 10514

  Enjoy easy living in this fully renovated Cape Cod style home situated on a park-like, flat property. Located walking distance to town and train, this 3 bedroom/2.5 bathroom residence offers modern luxuries in a classic country-feeling home. Enter this home through an inviting foyer flanked by a front-to-back living room, featuring a wood-burning fireplace and a formal dining

  Allison Tintenfass Compass Greater NY, LLC

  4 Oak Hill Rd, Chappaqua, NY 10514
• 

  Est $2,206,912 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,664 Sq Ft

  9 Meadow Hill Place, Armonk, NY 10504

  9 Meadow Hill Place, Armonk, NY 10504
• 

  

  /32

  $1,599,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,732 Sq Ft

  35 Whitlaw Ln, Chappaqua, NY 10514

  Timeless elegance meets modern comfort in this beautifully updated Colonial home. Double entry front doors open to a gracious foyer, setting the stage for the home’s expansive and light-filled layout. At its center, the renovated chef’s kitchen impresses with gleaming Caesarstone countertops, professional-grade stainless steel appliances, dual dishwashers, an oversized island with prep sink,

  Jennifer Harris Compass Greater NY, LLC

  35 Whitlaw Ln, Chappaqua, NY 10514
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  /9

  $2,100 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.

  Mary Grant Houlihan Lawrence Inc.

  85 Paulding Dr, Chappaqua, NY 10514
• 

  $1,465,000 Sold Oct 01, 2025

  • 1,917 Sq Ft
  • $764/SF
  • 11 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1938

  33 High Way, Chappaqua, NY 10514

  Picture-perfect Colonial in Chappaqua's highly sought after Lawrence Farms South neighborhood. Beautifully updated and impeccably maintained 3-bedroom, 3.5-bath home sits on nearly an acre of level, landscaped property with lush lawns and unparalleled curb appeal. Radiating a perfect blend of classic charm and modern luxury, this home welcomes you with light-filled, well-proportioned living

  Jennifer Harris Compass Greater NY, LLC

  33 High Way, Chappaqua, NY 10514
• 

  Est $2,517,274 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,249 Sq Ft

  16 Kittle Rd, Chappaqua, NY 10514

  16 Kittle Rd, Chappaqua, NY 10514
• 

  

  /39

  $2,500,000

  • 5 Beds
  • 5.5 Baths
  • 5,907 Sq Ft

  61 Carolyn Place, Chappaqua, NY 10514

  Located in the coveted Whippoorwill estate area, 61 Carolyn Place presides on 2.19 manicured acres and overlooks the Whippoorwill Country Club’s private golf course. Meticulous details abound with lofty ceilings and spacious rooms, complemented by warm, inviting, intimate spaces and outdoor areas. An open gourmet kitchen and breakfast room flow to the grand two-story family room and dedicated

  Richard Hopple Julia B Fee Sothebys Int. Rlty

  61 Carolyn Place, Chappaqua, NY 10514
• 

  

  /26

  $9,500 per month

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • House for Rent

  306 Quaker Rd, Chappaqua, NY 10514

  Smartly renovated 1930's Colonial walking distance to town, train, shops & school. Impressive columned front portico w/double-door entry. Formal living room w/fireplace & crown molding. Formal dining room w/French doors to patio & crown molding. High-end kitchen features Wolf, Fisher Paykel & Bosch appliances open to family room w/cathedral ceiling & French doors to patio. Main floor den/office

  Stacy Levey William Raveis-New York, LLC

  306 Quaker Rd, Chappaqua, NY 10514
• 

  

  /44

  $1,774,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,614 Sq Ft

  21 Wallace Way, Chappaqua, NY 10514

  Better than new at Chappaqua Crossings Carriages! Be among the first to experience this spectacular new community featuring a delightful and charming village atmosphere in the heart of Westchester, Chappaqua, NY. This stunning “Byram Newhaven model” situated in a prime location within the community, offers great curb appeal with its expansive front porch, stone walls and specimen plantings; and

  Ken Wile Redfin Real Estate

  21 Wallace Way, Chappaqua, NY 10514
• 

  Est $1,711,315 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,045 Sq Ft

  55 Cowdin Cir, Chappaqua, NY 10514

  55 Cowdin Cir, Chappaqua, NY 10514

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