Chappaqua Homes under $1.5 million

Welcome to Chappaqua, a charming community nestled in the heart of Westchester County, New York. Renowned for its picturesque landscapes and vibrant community spirit, Chappaqua is not just a place to live but a lifestyle to embrace. One of the standout features of this delightful town is its exceptional school district, which consistently ranks among the top in the state. The Chappaqua Central School District is dedicated to fostering academic excellence and personal growth, offering a robust curriculum and a wealth of extracurricular activities that cater to students' diverse interests. Parents can rest assured that their children will receive a high-quality education in an environment that encourages creativity, critical thinking, and collaboration.

For those considering making Chappaqua their home, the real estate market offers an array of options, with charming homes available under $1.5 million. Whether you’re seeking a cozy colonial, a modern contemporary, or a classic Cape Cod, you’ll find properties that blend comfort with style, all set against the backdrop of beautiful tree-lined streets and serene parks. The community is known for its welcoming atmosphere, where neighbors become friends and families thrive.

Living in Chappaqua means enjoying a balance of suburban tranquility and urban convenience. With easy access to New York City and local amenities, including quaint shops, delightful restaurants, and vibrant cultural attractions, you’ll find everything you need right at your fingertips. Embrace the opportunity to be part of this exceptional community where quality education and charming homes await you!

Newest Chappaqua Homes under $1.5 million

$959,000

3 Beds ⋅ 2 Baths ⋅ 1057537 MLS

A private acre, a sought-after Chappaqua location, and the convenience of one-level living come together in this inviting Rolling Fields home. With three bedrooms, a spacious primary suite with its own bath, and an easy-flowing floor plan, the home offers comfortable living with room to make it your own.The heart of the home is the renovated kitchen, featuring granite countertops and stainless steel appliances with an open connection to the dining area. Hardwood floors and a wood-burning fireplace add warmth and character to the generous living room. The primary suite provides a comfortable retreat with a private en-suite bath.The home was substantially updated in 2013, including the roof, windows, mechanical systems, kitchen, and baths. A standout feature is the three-car garage, with both an attached garage and a separate two-car garage. Set in the desirable Rolling Fields neighborhood and within the award-winning Chappaqua School District, the property is conveniently located near Chappaqua and Mount Kisco, Metro-North transportation to NYC, shopping, restaurants, parks, and local amenities.

10 Horseshoe Road, Mount Kisco

$1,249,000

3 Beds ⋅ 4 Baths ⋅ 1015940 MLS

Sophisticated Riverwoods Living. Elegant, private, and impeccably appointed, this exceptional Riverwoods townhome offers a refined lifestyle in one of the area’s most desirable communities. Meticulously maintained and recently renovated, this sophisticated residence combines timeless architectural details with thoughtfully updated interiors, generous living spaces, and an enviable setting within the sought-after Chappaqua school district. At its heart, the open-concept main level offers a sun-filled eat-in kitchen, beautifully renovated in 2025 with custom-style cabinetry, new appliances, and quartz countertops. The adjoining dining area is enhanced by elegant architectural molding, while the beautifully proportioned living room offers a wood-burning fireplace and double French doors that open onto an expansive deck. Overlooking mature, park-like landscaping, the deck provides a serene private retreat for morning coffee, al fresco dining, or effortless entertaining. An additional family room and guest quarters with built-ins and an adjacent powder room offers exceptional flexibility rarely found in townhouse living. Upstairs, two generously proportioned bedrooms feature high ceilings, abundant closet space, and an airy, light-filled ambiance. The spacious primary suite is a private sanctuary, complete with double French doors opening to a charming Juliette balcony. Beautifully updated bathrooms, an upstairs laundry area, and thoughtfully designed storage further enhance the home’s comfort and functionality. The finished lower level extends the living experience with a generous family/media room featuring a built-in entertainment center, private guest quarters with a bedroom and full bath, and three additional walk-in storage rooms - perfect for guests, recreation, work, or hobbies. Adding to the appeal is the home’s exceptional privacy. Attached only at the garage, with no shared living walls, the residence enjoys an uncommon sense of separation and tranquility, complemented by open-space views and mature landscaping. Set within the coveted Riverwoods community, residents enjoy an elevated array of amenities designed for both recreation and relaxation. The beautifully appointed clubhouse features an indoor pool, fitness center, and community rooms, while outdoor amenities include tennis courts and a swimming pool. Ideally located just minutes from the train, shopping, dining, and all that the surrounding area has to offer, this exceptional residence represents upscale, effortless living at its finest—where privacy, elegance, space, and convenience come together in a truly special setting.

34 Old Town Crossing, Mount Kisco

$1,299,000

3 Beds ⋅ 2 Baths ⋅ 1056666 MLS

Enjoy easy, comfortable living in this beautifully renovated and meticulously maintained Mid century modern home with one level living, situated in the sought-after Chappaqua School District. Set on more than a half acre of beautifully landscaped property, this inviting home offers privacy, level play areas, and a convenient location close to both the charming towns of Chappaqua and Pleasantville. This mid century modern home contains period related elements including large picture windows, stacked stone fireplace and slate flooring in the dining area. A welcoming foyer opens to an expansive, light-filled living and dining area designed for both everyday living and entertaining. The spacious living room features an oversized picture window, filling the space with natural light, along with a raised-hearth, stacked-stone wood-burning fireplace that creates a warm and inviting focal point. Large windows throughout the home bring in an abundance of natural light and offer lovely views of the surrounding property. Glass sliders provide seamless access to the rear yard and patio. The newly renovated eat-in kitchen combines style and function with crisp white cabinetry and beautiful quartz countertops. Three generously sized bedrooms provide comfortable accommodations, including a spacious primary suite with an en-suite bath and two large closets. Two additional bedrooms share a well-appointed hall bath. Step outside to a serene and private setting where the beautifully landscaped grounds create an ideal backdrop for relaxation and recreation. The expansive patio is perfect for al fresco dining, entertaining, or simply enjoying a quiet afternoon with a good book. New washer/dryer and kitchen appliances including wine refrigerator, new hardwood floors, new LED overhead lighting, freshly painted interior, whole house Generator and more. Charming, turnkey, and thoughtfully updated, this wonderful home offers easy living in a highly desirable location. Move right in and enjoy all that this special property has to offer!

11 Greenbriar Drive, Chappaqua

$649,000

2 Beds ⋅ 2 Baths ⋅ 1054305 MLS

Welcome to Chestnut Oaks, where generous space, a convenient Chappaqua location, and a thoughtfully designed layout come together in this beautifully maintained two-bedroom, two-bath residence offering more than 1,500 square feet. Step inside and you immediately appreciate how spacious this home feels. The large kitchen offers abundant cabinetry, granite countertops, and plenty of workspace for cooking, gathering, and entertaining. Just beyond, the dining area overlooks the living room below, creating an open, connected feel while still giving each space its own sense of place. The living room is warm and inviting, with sliding glass doors opening directly to a private patio, extending the living space outdoors for morning coffee, dining, or simply enjoying the surroundings. One of the highlights of this home is its wonderfully functional layout. The primary bedroom is located on the same level as the main living area and offers beautiful natural light, generous closet space, and a spacious en-suite bath with a walk-in shower, oversized vanity, and excellent cabinetry and storage. Upstairs, a second generously sized bedroom is nicely separated from the primary suite, offering flexibility for a bedroom, home office, den, library, or guest space. Additional closets and conveniently located laundry add to the ease of everyday living. Lovingly maintained over the years, this home is ready for its next chapter. And then there is the location. Chestnut Oaks offers an in-ground pool, tennis courts, and a community garden, all just moments from the heart of downtown Chappaqua. Leave the car behind and enjoy easy access to Metro-North, shops, restaurants, cafés, and everything the village has to offer. Spacious, versatile, and beautifully situated, this is an opportunity to enjoy more than 1,500 square feet of living space with outdoor access and community amenities in the heart of Chappaqua.

331 N Greeley Avenue, Chappaqua

$1,375,000

3 Beds ⋅ 2 Baths ⋅ 1048628 MLS

Location, Location, Location and the yard you have dreamt of! Set on a gorgeous, level, private acre on a flat cul-de-sac street that leads to sidewalks to downtown Chappaqua, Grafflin Elementary, and Bell Middle School, and just minutes from Whole Foods, Lifetime Fitness, Greeley High School, and more. This well maintained 3-bedroom, 2-bath home, with only $21,452 in taxes, shows pride of ownership the moment you walk down its blue stone walkway, with recent updates including a roof (2020), low-maintenance siding (2020), new AC (2020), new above-ground oil tank (2026), updated bathrooms, and a generator transfer switch for peace of mind. A well proportioned foyer opens to a spacious living room with wood-burning fireplace and large bay window, flowing seamlessly into a generously sized dining room. The sun-drenched eat-in kitchen with large picture windows and door opens to the oversized deck overlooking the picture-perfect backyard — providing ample space for outdoor dining and relaxing. Inside, are three well-appointed bedrooms, including a primary bedroom with recently renovated ensuite bathroom (2025) (hardwood under all bedroom carpets). The finished lower level boasts recessed lighting and second wood-burning fireplace with a door to the expansive backyard. The lower level also features built in shelves, and ample storage. The huge, flat backyard speaks for itself — perfect for all field sports, a playground, and trampoline (yes all three at once), home expansion, or - with septic in front - a possible pool site. Dream Big - Here!

88 Brevoort Road, Chappaqua

$1,359,000

3 Beds ⋅ 3 Baths ⋅ 1041830 MLS

A private woodland retreat in the Chappaqua School District, where natural beauty, flexible living space, and everyday convenience come together. Tucked along a charming woodland drive, this inviting home offers privacy, natural beauty, and an exceptional location close to everything. Surrounded by mature trees, natural rock formations, and lush landscaping, the property feels wonderfully secluded while remaining convenient to Chappaqua and Millwood shops, restaurants, parks, hiking trails, Metro-North, and the Taconic Parkway. Inside, abundant natural light, hardwood floors, oversized windows, and beautiful architectural details create a warm and welcoming setting. The main level is designed for both everyday living and entertaining, with an eat-in kitchen and bright breakfast nook, formal dining room, comfortable living room, and an expansive sunken family room with fireplace. Easy access to the deck and private grounds creates a natural indoor-outdoor connection. Upstairs, the generously proportioned primary suite provides a peaceful private retreat, with a dedicated vanity and sink area and a comfortable sense of separation from the rest of the home. Two additional bedrooms and a separate home office/den complete the second level, providing an ideal dedicated workspace for today’s lifestyle. Outside, the spacious deck overlooks the lush, private grounds and surrounding woodland, offering a beautiful setting for morning coffee, outdoor dining, entertaining, or simply unwinding at the end of the day. A two-car garage adds everyday convenience, while the location provides easy access to Chappaqua schools, Gedney Park, hiking trails, local shopping and dining, Metro-North, and the Taconic Parkway, making the NYC commute straightforward. Private, peaceful, and connected, this is a wonderful opportunity to enjoy the best of the Chappaqua area with space to live, work, entertain, and truly enjoy home.

180 Somerstown Road, Millwood

$679,000

4 Beds ⋅ 2 Baths ⋅ 1034483 MLS

A Rare Opportunity in the Heart of Millwood. Lake life, privacy, Chappaqua schools, and the convenience of being minutes from the heart of Millwood. This unique property offers an exceptional opportunity to create your own retreat in one of Westchester's most desirable communities. Set back from the road on 0.55 acres of beautiful grounds, this four-bedroom Raised Ranch enjoys a wonderful sense of privacy and connection to nature, while being just minutes from Millwood's shops, restaurants, and everyday conveniences. Mature landscaping and wooded surroundings create a natural buffer from the road and a setting that feels surprisingly removed from the activity of the area. And then there is Hidden Hollow Lake one of the property's most exceptional features. The home enjoys exclusive rights to the private Hidden Hollow Lake Community at no additional charge, a rare benefit enjoyed by very few properties. Residents have access to a private sandy beach where they can swim, kayak, and canoe, creating a true vacation-like lifestyle just steps from home. Built in 1954 and offering approximately 1,200 square feet, the four-bedroom, 2 bath home is being offered strictly as-is and presents an exciting opportunity for buyers looking to renovate, expand, or create a home uniquely suited to their needs. The main level features a welcoming living room with an open red-brick fireplace and wood-burning stove, with sliding doors opening to a charming three-season sunroom overlooking the backyard. The kitchen and dining area, powder room, laundry room, and access to the one-car garage complete this level. Upstairs are four bedrooms and a full bathroom. The primary bedroom offers access to a large covered sunroom and a beautiful wooden deck overlooking the grounds, providing a wonderful place to enjoy the natural setting and envision future possibilities. Outside, mature landscaping, flowering trees, specimen plantings, and wooded surroundings create a beautiful natural backdrop. A walking trail from the property leads toward Hidden Hollow Lake, making it easy to enjoy the lake and its recreational amenities right from home. The location is equally appealing. The property is just minutes from Millwood Shopping Plaza, home to DeCicco's Gourmet Market, Tazza Cafe, Drug Mart, and the Millwood Post Office. The Taconic State Parkway is easily accessible, as is Gedney Park and the North County Trailway, offering miles of opportunities for walking, running, and biking. Located in the highly regarded Chappaqua Central School District, the property combines the convenience of a central Millwood location with the beauty of mature grounds, lake access, and abundant outdoor recreation. A rare Millwood opportunity with deeded Hidden Hollow Lake rights, Chappaqua schools, beautiful grounds, and room to create something truly your own. A property with possibilities and a lifestyle that is increasingly difficult to find.

457 Saw Mill River Road, Millwood

$1,490,000

3 Beds ⋅ 4 Baths ⋅ 1017997 MLS

$100,000 REDUCTION Expanded and Renovated Colonial in the Heart of Chappaqua - New 4 bedroom Septic, 2024 Roof and Exceptional Indoor/Outdoor Living. Just moments to Chappaqua village, Metro North and highly regarded Chappaqua schools. A flexible first-floor guest/au pair suite with private bath, chefs kitchen with Wolf appliances, private primary suite, 2 fireplaces, expansive deck and mature grounds backing to protected green space. A welcoming foyer opens to a gracious living room and fireplace. A formal dining room with a tray ceiling. Timeless appointed chefs eat-in-kitchen with Wolf appliances, custom cabinetry and marble counter tops, wine refrigerator and breakfast bar. The family room offers a second fireplace, a coffered ceiling, and a wall of windows to view the private setting. The sunroom offers custom built-ins and an abundance of natural light. A first floor au pair/guest room and full bath. Upstairs is the primary bedroom with high ceilings, walk-in custom closet, private study with built-ins, and en-suite bath with double sinks, marble shower and whirlpool tub. Two additional bedrooms, one with custom built-ins, custom closets, and a hall bath. New laundry is located conveniently on the second floor. Outdoors, an expansive deck extending the living space and creating the perfect setting for entertaining, dining and relaxing while overlooking mature landscaping and private grounds that back up to protected green space. Completing the property is a detached two car-garage with generous storage above.

131 Douglas Road, Chappaqua

$995,000

2 Beds ⋅ 3 Baths ⋅ 1004449 MLS

Welcome to this beautifully situated townhouse in the highly desirable Riverwoods community, where tranquil woodland views and thoughtfully designed living spaces create the perfect retreat. Nestled against a picturesque backdrop of mature trees and a gently flowing stream, this home offers both privacy and natural beauty in an exceptional setting. The sun-filled eat-in kitchen is as inviting as it is functional, featuring granite countertops, a gas stove, abundant cabinetry, and plenty of space for casual dining. Just beyond, the elegant formal dining room is framed by stunning triple floor-to-ceiling windows that bring the outdoors in and fill the space with natural light. The gracious living room is equally impressive, highlighted by detailed dentil moldings, a classic wood-burning fireplace with a handsome wood mantel, and sliding doors that open to a spacious deck overlooking the serene wooded landscape—an ideal spot for morning coffee, outdoor dining, or simply unwinding in nature. As you ascend to the second floor, a sunlit hallway lined with three oversized windows creates a bright and airy ambiance throughout the home. The expansive primary suite is a true sanctuary, featuring soaring cathedral ceilings, a generous walk-in closet, and a charming Juliet balcony with peaceful views of the private woods below. The luxurious primary bath offers a double vanity, a relaxing soaking tub, and a separate stall shower for a spa-like experience. A second spacious bedroom with its own ensuite bath provides comfort and privacy for family or guests, while the conveniently located laundry area on the upper landing adds everyday ease. The walk-out lower level offers exceptional flexibility, with a large family room perfect for gatherings, movie nights, or recreation. An additional versatile room can easily serve as a home office, gym, or guest space, complemented by a convenient half bath. A dedicated storage room and utility area complete this well-designed lower level. Combining elegant architectural details, generous living spaces, and a spectacular natural setting, this exceptional Riverwoods home offers comfort, charm, and a lifestyle of relaxed sophistication.

4 Annes Wood Lane, Mount Kisco

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 1013791 MLS

Renovated and Reimagined Colonial on Spectacular Park-Like Grounds, this exceptional residence includes a separate cottage-style bonus building that offers endless possibilities. Whether envisioned as a private home office, artist’s studio, yoga or fitness center, man cave or an inspiring creative workspace, this detached structure provides exceptional flexibility and privacy. Nestled amid the lush grounds and mature landscaping, it serves as a peaceful extension of the home and creates a rare opportunity for today’s work-from-home lifestyle or entrepreneurial pursuits. At the heart of the home, an original stone wood-burning fireplace serves as a stunning focal point, infusing the living space with warmth, character, and timeless charm. Perfect for cozy winter evenings, holiday celebrations, and memorable gatherings with family and friends, this impressive architectural feature creates an inviting atmosphere that embodies the true spirit of home. The stunning chef’s kitchen features premium stainless-steel Thermador appliances, elegant quartz countertops, a spacious walk-in pantry, and seamless access to an oversized slate patio—ideal for indoor-outdoor entertaining. The captivating primary suite offers soaring beamed ceilings, a generous sized walk-in closet, and a luxurious spa-inspired bath complete with dual vanities and a classic clawfoot soaking tub. Convenient second-floor laundry with storage enhance everyday living. Additional highlights include all-new Anderson windows, all new electrical, all new plumbing, new roof, new c/air, new Navien system, energy-efficient blown-in insulation, solid wide-plank oak flooring, and exquisite custom millwork throughout. The separate cottage building has all new electrical, blown insulation, windows, flooring and roof. Located minutes from the Metro North Train Station and downtown Chappaqua, you'll have quick access to commuter routes and a charming village filled with shopping, restaurants and community events. A rare offering that perfectly blends timeless charm with sophisticated modern updates, all set within a serene and private setting. The outbuilding / studio can be converted back to a garage. Square footage does not include the studio space.

676 Hardscrabble Road, Chappaqua

$999,000

3 Beds ⋅ 3 Baths ⋅ 997307 MLS

Private access to the scenic North County Trailway, offering miles of paved trails for walking, running, and biking, is just one of the many highlights of this beautifully maintained home. Not to be missed, this sun-filled 3-bedroom, 3-bath raised ranch offers a comfortable layout ideal for both everyday living and entertaining. Set privately on over 1.3 level acres and screened from the road by a row of mature trees, the property provides exceptional privacy and a peaceful setting. Enjoy summers by the in-ground pool, a spacious backyard perfect for play and gatherings, and the convenience of a 2-car garage. Ideally located in the heart of Millwood, close to shopping, restaurants, and major parkways and in Chappaqua Schools, this home offers the perfect balance of privacy, recreation, and convenience. New AC!

568 Saw Mill River Road, Millwood

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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.