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Chappaqua NY Real Estate & Homes for Sale

29 Properties Found

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$1,275,000

10 North Ln Chappaqua, NY 10514

MLS: 879079 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
3,155
Status:
NEW LISTING
MLS#:
879079
Type:
Single Family
Lot size:
1.1 Acres
Year built:
1950
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Keller Williams Realty Partner 914-962-0007
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ADDITIONAL INFORMATION

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 dead-end street just minutes from the Taconic Parkway, shopping, and the vibrant Chappaqua town center. Enjoy a beautifully level yard, ideal for outdoor entertaining, play, or peaceful relaxation. Featuring updated hardwood floors, a convenient first-floor bedroom, and tasteful minor updates throughout, this home blends space, style, and serenity. A rare opportunity in one of Westchester’s most desirable communities!

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$2,225,000

50 Overlook Dr Chappaqua, NY 10514

MLS: 877002 Photos
Beds:
6
Baths:
6.00
Sq.Ft.:
5,234
Status:
NEW LISTING
MLS#:
877002
Type:
Single Family
Lot size:
1.2 Acres
Year built:
1929
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-238-4766
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ADDITIONAL INFORMATION

50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors. This one-of-a-kind home is a must see. Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can offer. Homes built to this quality are a rare find. Constructed in 1929, the home is also graced with soaring ceilings, intricate period moldings, and expansive sunlit interiors. Designed for both grand entertaining and comfortable living, this spacious home is roaring with charm and can suit a variety of tastes and living styles. The first floor offers a living room with fireplace, an all seasons sunroom, a bright and airy dining room, a kitchen with pantry and wet-bar, a half bath, and an in-law or au pair suite with a full bath. Upstairs features 5 bedrooms and 3 full baths, a grand hallway, and attic access. Additional recreational space is provided in the finished basement, with a family room, a gym, and large mudroom, a half-bath, and a utility room. The beautifully landscaped 1.2-acre lot boasts stunning specimen plantings and a private stone patio adjacent to the all-seasons sunroom. There is also a charming bridge, designed by renowned architect Ned Baldwin, leading to a park-like setting in the backyard. This is an incredible opportunity to own a truly distinguished home in one of Chappaqua’s most desirable neighborhoods. Experience the perfect balance of classic architecture and modern luxury in this extraordinary residence, in a home that is built to stand the test of time.

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$850,000

249 Mill River Rd Chappaqua, NY 10514

MLS: 876568 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
2,100
Status:
NEW LISTING
MLS#:
876568
Type:
Single Family
Lot size:
0.45 Acres
Year built:
1967
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Town and Village Real Estate 877-295-4111
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ADDITIONAL INFORMATION

Contemporary bi-level 4 beds 2 Bath home. Enjoy comfort and sophistication with red oak hardwood flooring, recent upgrades like a new roof, boiler, and sanitary system. Large living room with ample space for holiday gatherings. Entertain effortlessly with three freshly stained multi-level decks, perfect for parties and functions. Large yard to enjoy outdoor activities, with three sheds, offers plenty of outdoor storage . Located in Chappaqua P.O. within the prestigious Pleasantville School system, enjoy convenience with a Rare FREE SCHOOL BUS PICK UP! in a walking school district of Pleasantville!!! On a Cul-de-sac. Easy 5-minute walk to the Chappaqua Train station just 45 minutes to Grand Central Station. Park-like grounds, fostering freedom and adventure. Inside, cathedral ceilings and Red Oak hardwood floors elegance, comfort and style in a coveted Chappaqua location, minutes to Farmers market shops train and restaurants. 1 Car Attached Garage

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$1,275,000

4 Southview Rd Chappaqua, NY 10514

MLS: 864093 Photos

Open House:

Saturday, 6/21 1:00-3:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
2,111
Status:
Active
MLS#:
864093
Type:
Single Family
Lot size:
0.7 Acres
Year built:
1952
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-238-4766
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ADDITIONAL INFORMATION

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 to the Saw Mill River Parkway and Downtown Chappaqua. This location is one of the best in Chappaqua and is highly coveted. This lovingly-maintained home is flooded with sunlight and has all new windows and doors, which provide easy access to and enjoyment of its lush landscaping and beautiful perennial gardens. Substantial Entry Foyer with Closet leads to large open plan Living Room with stone wood burning fireplace, custom built-ins, and separate Dining Area. Sliding glass doors in Living Room lead to expansive Deck with steps to Lower Patio which is ideal for Outdoor Firepit. There is a tremendous amount of room for entertaining! The Kitchen is beautifully renovated with stainless steel appliances, and a Breakfast Nook. Additional rooms on the first floor include a very large and sunny Primary Bedroom with an oversized picture window, two ample closets, and a Primary Bathroom, one additional Bedroom, a large and well-appointed Office/Bedroom, and a Hall Bathroom with gleaming hardwood floors throughout the first floor. Lower level is fully finished with a Yoga/Exercise Room, Office/Bedroom with another stone wood burning fireplace, luxurious Bathroom with Steam Room, and a separate Entrance which opens on to the Lower Patio, ideal for au pair, mother-in-law suite, or overnight guests from the city! The Attic is accessed by a full staircase, provides an enormous amount of storage, and is ready for substantial expansion possibilities. Do not miss this wonderful Home with its spectacular location close to everything Chappaqua has to offer! New Septic Fields, New Water Heater, and Newly Paved Driveway.

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$1,200,000

29 Begg Dr Chappaqua, NY 10514

MLS: 863423 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
863423
Type:
Single Family
Lot size:
0.43 Acres
Year built:
1934
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-238-4766
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ADDITIONAL INFORMATION

Welcome to 29 Begg Drive, a meticulously-maintained gem in Chappaqua! This serene property features an open floor plan with hardwood floors, charming traditional architectural features, and numerous upgrades. The sunlit first floor features a kitchen with a large picture window, a living room area, and a dining area. An attached screened-in porch, which overlooks the yard and connects to a large refurbished exterior deck, is a love place to relax and enjoy the bucolic views. The 2nd level features a full bath, 2 bedrooms, and a home office. Continue to the 3rd level, which boasts a newly updated primary suite with skylights, walk-in closets, and fully renovated bathroom. The basement level, with a laundry and utility room, offers additional space and many opportunities. Outside, lush landscaping with mature shade trees create a private setting to enjoy for years to come, with a stone patio for additional outdoor entertainment. This picturesque home is close proximity to Metro North and downtown Chappaqua, which features delightful shops and restaurants, a fantastic library, a thriving farmer's market, and award-winning schools.

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$2,800,000

61 Carolyn Pl Chappaqua, NY 10514

MLS: 872931 Photos
Beds:
5
Baths:
6.00
Sq.Ft.:
5,907
Status:
Active
MLS#:
872931
Type:
Single Family
Lot size:
2.19 Acres
Year built:
1995
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Julia B Fee Sothebys Int. Rlty 914-234-0200
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ADDITIONAL INFORMATION

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 solarium, both accessing a large outdoor deck and rocking chair porch. The second-floor features a large primary suite with a gorgeous, sun-drenched bedroom complete with western-views and a wood burning fire place. A sitting room/second office, double walk-in closets, and a lavish bath with a jacuzzi tub, dual vanities and a spacious shower complete the suite. A wide hallway spanning the breadth of the home gives access to two additional ensuite bedrooms, the upstairs laundry room, and home office. The home’s eastern wing, features the final two bedrooms, connected by a Jack-and-Jill bath and features a Juliet balcony overlooking the front yard. A heated, three car garage, connecting mudroom, and full, walk-out basement complete the interior, while the expansive front and backyards feature vast rolling lawns, beautiful scenery, and a potential pool site. Conveniently located between Chappaqua and Armonk, close to town and highways, and approximately 50 minutes to NYC, 61 Carolyn Place is a truly remarkable home and not to be missed.

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$1,799,999

200 Millwood Rd Chappaqua, NY 10514

MLS: 875237 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
3,009
Status:
Active
MLS#:
875237
Type:
Single Family
Lot size:
3 Acres
Year built:
1932
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-238-0676
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ADDITIONAL INFORMATION

Tucked away in a 3+ acre private storybook setting, this reimagined farmhouse blends timeless charm with modern comfort. Set back from the road on a scenic, private property with gorgeous mature landscaping, two tranquil ponds, and wide-open views, this 4-bedroom home is a peaceful retreat unlike any other. Inside, the open, sunlit layout features oversized windows that invite the outdoors in, and wide-plank hardwood floors that bring warmth to every room. The beautifully updated kitchen anchors the main living space, offering high-end finishes and a seamless flow into dining and gathering areas—perfect for entertaining or quiet nights at home. Upstairs, the serene primary suite features a spa-inspired bath and a large, hotel-style walk-in closet. Three additional bedrooms and a dedicated office provide ample space for family, guests, or working from home. A detached garage with finished space above offers endless potential—think studio, gym, office, playroom or guest suite. Whether relaxing on the patio, strolling around the ponds, or enjoying the sweeping grounds, this rare farmhouse property delivers privacy, beauty, and a sense of home that feels like a hidden gem.

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$1,049,000

100 Castle Rd Chappaqua, NY 10514

MLS: 869177 Photos
Beds:
3
Baths:
4.00
Sq.Ft.:
2,590
Status:
Active
MLS#:
869177
Type:
Single Family
Lot size:
0.22 Acres
Year built:
1996
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-238-4766
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ADDITIONAL INFORMATION

Charm. Character. Convenience. Beautiful curb appeal! Welcome home to this wonderful home with rocking chair front porch. Original owners who built this delightful home in 1996. Impeccable 3 bedroom, 3.5 baths Traditional Colonial located in the heart of Chappaqua with level backyard. This home is better than new, it has been extensively renovated in the past 2 years. This modern home has it all: elegant interior, gracious foyer, a wonderful vista of surrounding countryside, hardwood floors, very bright with wall of new windows, crown molding, ceiling fire sprinker throughout, finished lower level with a bath and french door to outdoor. Main level consists of the chef's eat-in-kitchen with top-of-the-line stainless steel appliances, gardener's window, French door to wrap-around deck and pantry. Elegant formal living room with a fireplace and custom built-ins book shelves and seating bench, it opens to formal dining room with French door to huge wrap-around deck. Den/Office/Playroom and beautifully renovated powder room finishes the 1st floor. Second floor: a huge and bright Loft with two windows currently use for office/study/reading area. Luxurious primary bedroom with two walk-in her and his closets and brand new luxurious an en-suite primary bath (May 2025). Two bedrooms and beautifully renovated hall bath with a window completes the 2nd floor. Lower level has a new finished playroom/gym (May 2025) with a bath and walk-out French door to level backyard, private laundry and utilities. Addional upgrades: paved driveway (2024), new gas furnace (2023), new roof (2023), new AC, new landscaping (2024). On town sewer, natural gas and water. Minutues to all town amenities, including schools, shopping, dining, bus and train. It will not last!

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$1,890,000

50 Kerry Ln Chappaqua, NY 10514

MLS: 865068 Photos
Beds:
4
Baths:
5.00
Sq.Ft.:
4,051
Status:
Active
MLS#:
865068
Type:
Single Family
Lot size:
2.02 Acres
Year built:
1960
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-273-9505
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ADDITIONAL INFORMATION

Nestled on a coveted lane in Chappaqua, this expanded 4-bedroom Colonial offers an unparalleled blend of privacy, luxury, and charm. Set on over 2 acres of meticulously landscaped grounds, this exceptional property features a stunning gunite heated saltwater pool, lush mature plantings, and a picture-perfect setting that defines upscale suburban living. Step inside to discover a beautifully renovated kitchen, outfitted with top-of-the-line Wolf and Sub-Zero appliances, custom cabinetry, and a breathtaking picture window that overlooks the expansive backyard—a true centerpiece of the home. Enjoy family time in the casual family room or cozy nights by the fireplace in the living room. A perfectly situated main-level office is thoughtfully tucked away for quiet and privacy. Upstairs, the primary suite offers a walk-in closet that will delight even the most dedicated shoppers. Whether hosting poolside gatherings or enjoying peaceful mornings in your private sanctuary, this home offers it all.

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$1,265,000

26 Mayberry Rd Chappaqua, NY 10514

MLS: 868152 Photos
Beds:
5
Baths:
3.00
Sq.Ft.:
3,200
Status:
Active
MLS#:
868152
Type:
Single Family
Lot size:
1.1 Acres
Year built:
1964
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: William Raveis-New York, LLC 914-238-0505
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ADDITIONAL INFORMATION

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 open to the breakfast area, and a family room featuring a wood-burning fireplace with heat insert, skylight, and stairs up to a bonus/playroom over the garage. The family room has direct access to a fully enclosed 3-season sunroom and upper deck with stairs down to the stone patio below. The first floor also includes the primary bedroom with an en-suite bathroom, a home office, and an additional full bathroom. Upstairs, there are four generously sized bedrooms and a full bathroom. The walkout lower level has a sliding glass door to the patio and includes an additional 900 square feet of finished storage, a dedicated laundry room, and plenty of utility/storage areas.

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$3,499,000

93 Haights Cross Rd Chappaqua, NY 10514

MLS: 868090 Photos
Beds:
4
Baths:
5.00
Sq.Ft.:
6,542
Status:
Active
MLS#:
868090
Type:
Single Family
Lot size:
3.66 Acres
Year built:
1979
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-238-0676
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ADDITIONAL INFORMATION

Exceptional and sophisticated Nantucket shingle style Colonial on 3.66 private acres in one of Chappaqua’s most desirable neighborhoods, offers the perfect balance of casual elegance and resort-style living. Just 45 minutes from NYC and minutes to town, train, and top-rated schools, this turnkey home offers unmatched convenience and luxury. Designed for both everyday comfort and effortless entertaining, the property features sophisticated interiors and breathtaking outdoor spaces—creating a true sanctuary for modern family living. From the moment you arrive, you’ll be captivated by the lush, professionally landscaped grounds and impeccable curb appeal. The backyard is a true resort-style retreat, complete with a sparkling pool and spa, a built-in fire pit, an outdoor refrigerator and beverage area, and expansive level lawns—perfect for entertaining or unwinding in total privacy. Step inside and experience a turnkey masterpiece of design and craftsmanship. The interiors are adorned with high-end finishes, custom millwork, gorgeous hardwood floors and designer touches throughout. The chef’s kitchen is an entertainer’s dream, featuring top-of-the-line Wolf ovens and microwave, a six-burner Wolf range, a separate full size Sub-Zero refrigerator and freezer, dual dishwashers, and sleek, custom cabinetry. Other first floor highlights include a large office, a family room w/walls of windows, a billiard or living room w/ bar and sleek built-ins, and an incredible oversized screened porch w/fireplace and TV—perfect for gatherings and seamless indoor-outdoor entertaining. Upstairs, the primary suite is a luxurious sanctuary, boasting exposed wood beams, a cozy stone fireplace, a spa-like ensuite bath w/ steam shower, and generous walk-in closets. Three additional oversized bedrooms—two sharing a bath and one with its own ensuite—offer ample space and comfort, all connected by a versatile upstairs lounge area perfect for homework or hanging out. The finished walkout lower level adds even more living space with a media/playroom, a state-of-the-art home gym, a full bath, and access to a covered porch. Additional premium features include a heated three-car garage, whole-house generator, dual laundry rooms, whole house camera security system, and stunning stone walls that frame the property’s exceptional landscaping. Meticulously maintained and 100% move-in ready, this one-of-a-kind estate is a rare opportunity to enjoy resort-caliber living in a premier location. Prepare to fall in love!

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$1,175,000

57 Hamilton Dr Chappaqua, NY 10514

MLS: 844404 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
3,728
Status:
Active
MLS#:
844404
Type:
Single Family
Lot size:
0.9 Acres
Year built:
1965
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-591-2700
Request Info Save Property
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ADDITIONAL INFORMATION

Welcome to a sleek contemporary home that seamlessly blends indoor comfort with an exceptional outdoor retreat. From the moment you enter, you'll appreciate the design's focus on chic, easy living, bathed in natural light and showcasing exposed beams, custom built-ins, and premium appointments. This home boasts an open concept and has been fully updated, living generously like a 4 or 5-bedroom residence. The versatile lower level is a true bonus, offering a family room with a second fireplace, a wet bar perfect for entertaining, a guest room, a bathroom, and a flexible two-room office suite. Both levels feature glass doors that lead to three levels of decking, providing abundant space for outdoor enjoyment and tranquil views. Set on a hillside, this property offers a feeling of a private, elevated treehouse, ideal for entertaining or simply unwinding. Enjoy the convenience of being close to Chappaqua's town amenities and train station.

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$1,150,000

124 Seven Bridges Rd Chappaqua, NY 10514

MLS: H6324407 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,918
Status:
Active
MLS#:
H6324407
Type:
Single Family
Lot size:
3.25 Acres
Year built:
1935
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-962-4900
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ADDITIONAL INFORMATION

This beautiful Chappaqua house sits on 3.25 acres surrounded by formal gardens and woods. Designed by the renowned Westchester architect James Renwick Thomson in the 30's, this home seamlessly incorporates both elements of formal sophistication along with more casual charm. It is a one-of-a-kind gem, containing Palladian windows, vaulted ceiling, custom wood work, bay windows, Dutch doors, roughhewn beams and a second-floor terrace for dining al fresco. The grounds include formal gardens with multiple sitting areas, two koi ponds, and pebbled pathways. The red clay tennis court, stream, and long driveway add to the property's unique qualities. Join one of the many swim and tennis clubs minutes away. All this in the award-winning Chappaqua School District. Convenient to NYC by either car or train.

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$3,499,999

5 Briarcliff Rd Chappaqua, NY 10514

MLS: 843053 Photos
Beds:
4
Baths:
7.00
Sq.Ft.:
7,305
Status:
Active
MLS#:
843053
Type:
Single Family
Lot size:
1.29 Acres
Year built:
2007
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-238-0676
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ADDITIONAL INFORMATION

This distinguished 7,300-square-foot Colonial residence, constructed in 2007, is ideally situated on a level, professionally landscaped property, offering a rare blend of timeless architectural elegance and modern luxury. Meticulously designed and impeccably maintained, this exceptional home features four en-suite bedrooms with space for a fifth , a spacious bonus room/office, and a thoughtfully curated layout that strikes a balance between refined entertaining and everyday living. A dramatic two-story foyer introduces sun-drenched interiors adorned with detailed millwork, soaring ceilings, and four fireplaces—two adaptable for wood or gas—enhancing the formal living room, great room, primary suite, and lower-level entertaining space. At the heart of the home is a chef’s kitchen, outfitted with premium stainless steel appliances, custom cabinetry, and a striking marble island. This space opens gracefully to both formal and casual living areas, featuring multiple doors that lead directly to the porch, pool and patios, providing a seamless indoor-outdoor flow—ideal for entertaining, al fresco dining, and effortless serving. The main level is further enhanced by a custom-built mudroom with built-in storage, two elegantly appointed powder rooms, and an ideal layout for both formal and informal occasions. The expansive primary suite offers a private sanctuary, complete with a sunlit sitting room, custom walk-in closet, and a newly renovated spa bath finished with premium materials and fixtures. Three additional en suite bedrooms offer privacy and comfort, while the generously proportioned bonus room provides flexible space for a media lounge, home office, playroom, or guest accommodations. The walk-out lower level enhances the home’s appeal, featuring a full summer kitchen, a state of the art fitness center, a full bath, and an extraordinary 1,400-bottle climate-controlled wine room. A built-in movie screen paired with a state-of-the-art Dolby surround sound system creates a truly immersive in-home theater experience. Direct access to the grounds enhances the home’s indoor-outdoor lifestyle. The completely private, fully-fenced exterior is equally impressive, with a heated Gunite pool, patio, multiple lounging areas and flat lawns ideal for recreation, and a fully equipped outdoor kitchen designed for exceptional outdoor entertaining. Landscape uplighting and a backyard sound system enhance your outdoor enjoyment. This stately and luxurious residence represents a rare opportunity to acquire a home of scale, quality, and distinction in one of the area’s most sought-after locations.

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$1,199,000

34 Glenside Pl Chappaqua, NY 10514

MLS: 864676 Photos

Open House:

Wednesday, 6/18 11:00-3:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,880
Status:
Active
MLS#:
864676
Type:
Single Family
Lot size:
1.11 Acres
Year built:
1925
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Keller Williams NY Realty 914-437-6100
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ADDITIONAL INFORMATION

Live minutes from the heart of Chappaqua! Commuters dream to live in this charming tudor-style home near all everyday amenities. Nestled on 1.11 acres, with 3-bedrooms and 2 bathrooms, this fully renovated residence offers timeless character and thoughtful updates throughout. The main level features an inviting entry foyer, a chef’s eat-in kitchen equipped with a gas oven/range, microwave, and dishwasher, great for cooking and hosting. Step into the spacious living room with a cozy stone fireplace, den/office space, full bathroom and laundry hook up completing the first floor. On the second level, the primary bedroom offers a walk-in closet, along with two additional bedrooms and full bathroom. Distinctive interior details include beamed ceilings, crown molding, original woodwork, and recessed lighting. Enjoy hardwood floors throughout, central A/C, laundry hookups, and ample storage with a full attic and partial unfinished basement. The exterior is equally impressive with stone-accented driveway, peaceful surroundings the large front and back yards. Quiet and desirable street with no through traffic. Close to all, don't miss out on this opportunity!

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$899,000

341 Millwood Rd Chappaqua, NY 10514

MLS: 841702 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,541
Status:
Active
MLS#:
841702
Type:
Single Family
Lot size:
1.93 Acres
Year built:
1964
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Julia B Fee Sothebys Int. Rlty 914-295-3500
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ADDITIONAL INFORMATION

Nestled on nearly 2 acres of serene, wooded land, this beautifully maintained 4-bedroom, 2.5-bath home offers space, comfort, and privacy. The bright and airy eat-in kitchen features abundant cabinet space, a convenient in-kitchen laundry, and a large picture window overlooking the scenic backyard. A sun-filled living room with an oversized picture window enhances the home's warm and inviting atmosphere. The generously sized bedrooms provide ample space for relaxation, while the renovated lower level boasts all-tile flooring, a cozy wood-burning fireplace in the family room, an additional bedroom, a powder room, and plenty of storage. Enjoy outdoor living on the spacious deck, perfect for entertaining or unwinding while taking in the tranquil surroundings. The upper level of the private yard offers even more space, perfect for a fire pit or additional outdoor activities. Additional highlights include a full-house generator for year-round peace of mind, freshly painted interior, and hardwood floors under the carpeting. A perfect blend of space, functionality, and charm, this home is ready to welcome its next owners!

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$2,149,000

56 Annandale Rd Chappaqua, NY 10514

MLS: 859757 Photos
Beds:
4
Baths:
5.00
Sq.Ft.:
4,543
Status:
Active
MLS#:
859757
Type:
Single Family
Subdivision:
Lawrence Farms East
Lot size:
1.4 Acres
Year built:
2006
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: eXp Realty 888-276-0630
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ADDITIONAL INFORMATION

Welcome to 56 Annandale Road – a sleek & sophisticated Contemporary Colonial tucked into the prestigious Lawrence Farms East enclave, with panoramic views of the Mount Kisco Country Club’s fairways & pool. This rare offering delivers a perfect blend of privacy, style, & convenience in one of Westchester’s most sought-after communities. Set on almost an acre & a half of beautifully landscaped property, this home offers a fresh take on timeless living. Step through the entry door flanked by beautiful stonework into a large, open foyer & immediately feel the airiness & flow that define the home’s design. Large windows, wide hallways, & seamless transitions between rooms make every space feel connected, yet distinct. The main floor is designed for modern living – spacious enough to entertain, yet warm enough to feel like home. The formal Living & Dining Rooms are framed by elegant fireplaces & oversized picture windows, bringing in natural light & picturesque views. At the center of it all, the chef’s kitchen stuns with custom cabinetry, granite countertops, a large island, a gas cooktop, & high-end appliances from Sub-Zero, Bosch, & Thermador – the ideal space to cook, gather, & connect. With four bedrooms (lives like five), the layout fits today’s needs for flexible, functional spaces. The first-floor primary suite is a serene retreat, complete with its own sitting area & a steam shower in the primary bathroom. A second en-suite bedroom on the main level is perfect for guests, family, or a private office. A huge main level bonus room adds even more versatility – use your imagination. Three french doors give access from the main level to outdoor patio spaces, including one from the Primary Bedroom. A 2nd entrance into a well appointed mudroom & a powder room off the kitchen complete the main level. Upstairs, two additional bedrooms share a Jack & Jill bath & are joined by another spacious bonus room – ideal as a playroom, creative workspace, or remote office. Be sure to check out the extra finished storage space & secret room. The fully finished lower level offers endless options: a fitness zone, home theater, guest suite, storage areas, or all of the above – plus a full bathroom & direct access to the oversized 3-car garage with a Chargepoint EV charger. High-end touches elevate every corner: wide-plank Brazilian Cherry floors, detailed millwork, recessed lighting, a whole-house sound system, & smart upgrades throughout. Outside, enjoy two sun-soaked patios, a built-in propane grill with granite countertops, & a resistance spa/pool that transforms your backyard into a wellness retreat. Other highlights include: automatic whole-house generator (propane), central vacuum, security system, & school bus pickup right at your door. You're just minutes from Chappaqua Crossing’s shopping & dining scene – including Whole Foods, Starbucks, & more – & close to schools, Metro-North, & charming local villages. 56 Annandale Road is more than just a home – it’s where modern luxury meets laid-back elegance. Come experience the best of country club living with a modern twist. This one won’t stay on the market for long.

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$629,000

324 N Greeley Ave Chappaqua, NY 10514

MLS: 864496 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
1,608
Status:
Active
MLS#:
864496
Type:
Condo
Subdivision:
Chestnut Oaks
Year built:
1988
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: K. Fortuna Realty, Inc. 845-632-3492
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ADDITIONAL INFORMATION

Welcome to this beautifully renovated home in highly sought after Chestnut Oaks, steps from downtown Chappaqua. A rare opportunity to buy this end unit townhouse in the award-winning Chappaqua school district. This bright and spacious two-bedroom townhouse features a loft, its own washer/drier and balcony. Enjoy stress free living with low maintenance and taxes, close to town with a pool and tennis court on the property. Enter this unit from the second floor. The first level features completely redone and brand new hickory wood floors, 2 generous sized bedrooms and 2 full and newly updated bathrooms and a full size washer and drier. The 2nd level includes a large loft, perfect for a home office or small workout area. The kitchen features brand new appliances; a new stove, oven, refrigerator and microwave. Step out to your picturesque balcony overlooking a beautiful green common area behind the unit.

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$1,575,000

58 Spring Ln Chappaqua, NY 10514

MLS: 823805 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
3,457
Status:
Active
MLS#:
823805
Type:
Single Family
Lot size:
2 Acres
Year built:
1917
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-228-2656
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ADDITIONAL INFORMATION

Welcome to 58 Spring Lane – A stunning chalet-style retreat nestled at the end of a private lane just a short walk from the town of Chappaqua and Metro North train. This special home exudes timeless elegance and abundant period charm with its cathedral-vaulted ceilings, original gothic doors, expansive windows and versatile entertaining spaces. The main floor primary suite is a true sanctuary – like waking up in a forest canopy – and features an adjoining room with pocket doors ideal for a home office, nursery, or sitting area. Upstairs, three additional spacious bedrooms and full bath are complemented by a delightful nook, perfect for storage or a whimsical playroom. Abundant, well-outfitted closet spaces are found throughout the home. Entertain with ease in the beautifully updated kitchen with custom cabinetry and high-end appliances, all encompassing sleek finishes that blend modern appeal with classic charm. Be sure to check out the full-closet revolving spice rack. Powder room located conveniently off the kitchen adjacent the front door. An oversized dining area off the kitchen offers a gas fireplace and expansive views to the backyard with amazing natural light. Enjoy cozy evenings and effortless entertaining options in the cathedral-like living room with palladian-style windows and direct access to an outdoor wrap-around stone terrace – perfect for hosting meals and watching sunrise/sunset. Other highlights of the home include an outfitted workshop (formerly garage) with built-in shelving and side entry, and a finished walk-out lower level with a wet bar offering multiple options for a gym, playroom, or home office. Stone terraces and a wooden deck with views of the backyard offer ample entertaining options. Comfort and sustainability abounds with the home's 10.6KW solar panel array and Unico small-duct, high-velocity central heating, ventilation and air conditioning technology. This private oasis with gated-entry borders preserved land with direct access to a private trail leading to Pinecliff Audubon Sanctuary. Walking distance to town and train. A truly one-of-a-kind offering that is not to be missed.

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$3,150,000

70 Haights Cross Rd Chappaqua, NY 10514

MLS: 846261 Photos
Beds:
5
Baths:
9.00
Sq.Ft.:
8,775
Status:
Active
MLS#:
846261
Type:
Single Family
Lot size:
2.17 Acres
Year built:
2005
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-238-4766
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ADDITIONAL INFORMATION

Welcome to 70 Haights Cross, a stunning turn-key 5 bedroom, 7.2 bath colonial designed by noted architect Tasos Kokoris. Located in a coveted neighborhood, this home is set on 2 plus private professionally landscaped acres with a Gunite pool with waterfall and jacuzzi. The heart of the home lies in the gourmet kitchen featuring a Wolf-6-burner range, warming and fridge drawer, 2 Bosch dishwashers and a Subzero refrigerator. Flooded with sun-light and offering all of today's modern amenities, this home is truly a serene oasis offering unparalleled living space and is perfect for indoor or outdoor entertaining with an oversized deck and stunning patio. There is an expansive family room with gas fireplace, a wood paneled library with wood burning stove, home office and upstairs gathering room. The lower level features a spectacular garden room leading to a patio, 2 full baths, rec room, lounge, sitting room and mudroom. This home borders Glazier Arboretum and its spectacular hiking trails for ultimate tranquility: private and serene! Experience the pinnacle of gracious living.

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$2,300,000

3 Boulder Trl Chappaqua, NY 10514

MLS: 855848 Photos
Beds:
5
Baths:
5.00
Sq.Ft.:
5,183
Status:
Active
MLS#:
855848
Type:
Single Family
Subdivision:
Hardscrabble Lake
Lot size:
1.11 Acres
Year built:
2000
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 914-273-1001
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ADDITIONAL INFORMATION

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 the heated and air-conditioned 3-car garage. The top floor includes a primary bedroom suite with 2 walk-in closets, sun-filled primary bathroom with two separate vanities, walk-in steam shower and free standing soaking tub. Adjacent to the primary suite is a cozy study, 2 ensuite bedrooms with full bathrooms and one with access to the hall, plus a large fourth bedroom with walk-in closet and a 2nd floor laundry room. Completing this incredible home is a full walk-out lower level features a large rec room/family room with dry bar, wine cellar, a home theater, gym, full bathroom, and a bedroom/office. Enjoy entertaining and relaxing on the spacious, new Trex deck, play in the yard or telling stories while roasting marshmallows around the firepit. This property provides plenty of privacy with stone pillars at the entrance of the tree-lined driveway leading to the house. All just minutes to the town of Chappauqua and Metro North Train station into Grand Central Station.

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$1,790,000

21 Wallace Way Chappaqua, NY 10514

MLS: 854430 Photos
Beds:
3
Baths:
4.00
Sq.Ft.:
3,614
Status:
Active
MLS#:
854430
Type:
Townhouse
Subdivision:
Chappaqua Crossings Carriages
Lot size:
0.07 Acres
Year built:
2023
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Redfin Real Estate 631-337-8238
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ADDITIONAL INFORMATION

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 the distinct advantage of being within walking distance of various conveniences, retail establishments, Life Time fitness center, Starbucks, Whole Foods, community pool & state-of-the art clubhouse, shuttle service to the train for easy access to Manhattan, scenic walking trails, golf nearby and all the lower Hudson Valley has to offer. This exceptional home features beautifully appointed living space of the highest quality and perfectly designed for your enjoyment. It features three bedrooms, three and a half baths, a dedicated main floor office space, a versatile loft, and a large finished lower level complete with a full bathroom and large storage area ready to be finished to create even more space. The open-concept great room and kitchen are conducive to hosting large gatherings, and the expansive island with ample seating will be particularly appealing to those who enjoy culinary pursuits. The inviting fireplace surrounded by custom built-ins enhances the warmth and character of this fabulous room. There is also an ample sized mudroom with custom built-ins, conveniently located off the kitchen and leading to the convenient 2-car garage. This amazing home has been built with the highest quality interior and exterior architectural details with luxury landscape design and amenities surrounding. Also included in the sale are the Tv's, high end whole house surround sound system and terrace furniture. Don't miss the opportunity to call this home your own!

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$1,699,000

8 Carriage Ln Unit 84 Chappaqua, NY 10514

MLS: 852630 Photos
Beds:
2
Baths:
4.00
Sq.Ft.:
3,269
Status:
Active
MLS#:
852630
Type:
Condo
Subdivision:
Chappaqua Crossings
Lot size:
0.08 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-591-2700
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ADDITIONAL INFORMATION

Home Under construction a spacious 3269’ ! Move-in by Summer 2025' As you enter the Greeley Newhaven, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. The spacious kitchen and great room provide the ideal space for entertaining. The casual dining area provides the perfect space for entertaining guests with easy access to the kitchen. The two-story great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The first-floor primary bedroom suite features a lavish bathroom and a huge walk-in closet. The secondary bedroom includes a shared hall bath. The versatile loft can be suited to fit your lifestyle. Home features a covered and open 2nd floor terrace with built-in outdoor kitchen and gas grill. Work from home in the secluded second-floor office -Enjoy seamless indoor/outdoor living with the large second-floor terrace complete with an outdoor kitchen -The finished basement includes a media room and full bath -This home is located on a private street with wooded views from the terrace and sunset views from your front door.

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$1,679,000

10 Carriage Ln Unit 85 Chappaqua, NY 10514

MLS: 852625 Photos
Beds:
2
Baths:
4.00
Sq.Ft.:
3,269
Status:
Active
MLS#:
852625
Type:
Condo
Subdivision:
Chappaqua Crossings
Lot size:
0.08 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-591-2700
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ADDITIONAL INFORMATION

Home Under construction! Move-in by Summer 2025' 3269 square feet ! As you enter the Greeley Newhaven, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. The spacious kitchen and great room provide the ideal space for entertaining. The casual dining area provides the perfect space for entertaining guests with easy access to the kitchen. The two-story great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The first-floor primary bedroom suite features a lavish bathroom and a huge walk-in closet. The secondary bedroom includes a shared hall bath. The versatile loft can be suited to fit your lifestyle. Home features a covered and open 2nd floor terrace with built-in outdoor kitchen and gas grill. Work from home in the secluded second-floor office -Enjoy seamless indoor/outdoor living with the large second-floor terrace complete with an outdoor kitchen -The finished basement includes a media room and full bath -This home is located on a private street with wooded views from the terrace and sunset views from your front door.

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$1,724,995

19 Wallace Way Unit 25 Chappaqua, NY 10514

MLS: 852631 Photos
Beds:
2
Baths:
4.00
Sq.Ft.:
3,432
Status:
Active
MLS#:
852631
Type:
Condo
Subdivision:
Chappaqua Crossing Carriage Houses
Lot size:
0.07 Acres
Year built:
2022
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-591-2700
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ADDITIONAL INFORMATION

FULLY DECORATED AND FURNISHED MODEL HOME FOR SALE. 3432’ ‘Square Feet, 2 BR Byram Farmhouse. This model home includes an array of Luxury upgrades, which you can enjoy and move into this school year (Fall 2025). The Byram includes a finished basement with half bath and many more luxurious finishes. The open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private Rooftop Terrace with included Outdoor gas fireplace, 2 - Car Garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! Once completed this 91- Townhome community will surround it's owners with a delightful and eminently walkable Village full of the niceties that make Westchester living so extraordinary; charming Cafes & Restaurants, Lifetime fitness center, golf, Whole Foods Market, Shuttle to train into Manhattan, Walking Trails, Outdoor Pool, Clubhouse which will open this Summer, and much more.

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025, OneKey MLS, Inc. All Rights Reserved.


Chappaqua 10514 Real Estate

Chappaqua is located in New York. Chappaqua, New York 10514has a population of 3,062. Chappaqua 10514 is more family-centric than the surrounding county with 46.13% of the households containing married families with children. The county average for households married with children is 35.32%.

The median household income in Chappaqua, New York 10514 is $196,141. The median household income for the surrounding county is $105,387 compared to the national median of $69,021. The median age of people living in Chappaqua 10514 is 44.3 years.

Chappaqua Weather

The average high temperature in July is 82.7 degrees, with an average low temperature in January of 20.6 degrees. The average rainfall is approximately 50.2 inches per year, with 32.5 inches of snow per year.

Chappaqua Map

Chappaqua Real Estate Market Conditions

  • Median sales price

    $1,501,250
    10.6%
    change since last quarter

  • # Active listings

    29
    30-day change

Chappaqua Schools and Demographics

Education near Chappaqua, NY

City County
High School Graduates 98.63 88.85
College Degree - 2 year 0 6.61
College Degree - 4 year 82.49 50.65
Graduate Degree 30.75 17.54
Expenditures per Student 31,362 31,362
Students per Teacher 12.7 12.7

Elementary Schools near Chappaqua, NY

Grades Students P/T Ratio ZIP
Bedford Road School KG - 04 598 12.7 10570
Brookside School 01 - 02 743 15.5 10562
Claremont School 03 - 05 750 16.6 10562
Columbus Elementary School 03 - 05 446 12.6 10594
Douglas G Grafflin School KG - 04 414 13.8 10514
Mount Kisco Elementary School PK - 05 641 12.1 10549
Park School PK - KG 638 17.5 10562
Roaring Brook School KG - 04 464 14.1 10514
Westorchard School KG - 04 457 14.7 10514

Middle Schools near Chappaqua, NY

Grades Students P/T Ratio ZIP
Anne M Dorner Middle School 06 - 09 1,050 14.1 10562
Pleasantville Middle School 05 - 08 558 13.2 10570
Robert E Bell School 05 - 08 633 12.9 10514
Roosevelt School 05 - 05 344 18.1 10562
Seven Bridges Middle School 05 - 08 620 12.4 10514
Westlake Middle School 06 - 08 463 10.7 10594

High Schools near Chappaqua, NY

Grades Students P/T Ratio ZIP
Horace Greeley High School 09 - 12 1,331 12.3 10514
Ossining High School 09 - 12 1,343 13.7 10562
Pleasantville High School 09 - 12 601 11.8 10570
Westlake High School 09 - 12 589 13.1 10594

Ungraded Schools near Chappaqua, NY

Grades Students P/T Ratio ZIP
Edenwald School 01 - 12 107 6.7 10570
Mount Pleasant-Cottage School KG - 12 133 10.2 10570

Demographics near Chappaqua, NY 10514

Zip Code City
Neighborhood Type Suburban
Population 3,062 999,723
Population Density 6,700 2,322
Median Age 44.3 41.2
People per Household 2.7 2.7
Median Household Income 196,141 105,387
Average Income per Capita 99,474 61,830

Real estate near Chappaqua

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