Homes for Sale near Horace Greeley High School

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

Welcome to 56 Annandale Drive, Chappaqua, a capacious and captivating Cape Cod commandingly set on 1.4 acres in sought-after Lawrence Farms East within walking distance to Mount Kisco Country Club, Kittle House, Chappaqua Crossing, Horace Greeley High School and the town of Mount Kisco. Built for entertaining, every day is a holiday to celebrate in the open, spacious interiors, starting with the

Stacy Levey William Raveis-New York, LLC

Welcome to 9 Point Place, an exquisite, 4-bedroom, 3.5-bath Colonial located at the end of a cul-de-sac. This home offers approximately 4,100 sq ft of beautifully finished living space on nearly half an acre in the desirable Chappaqua school district. Step inside to an open, light-filled layout ideal for everyday living and entertaining. The kitchen features high-quality finishes and flows

Mark Boyland Keller Williams Realty Partner

Hywood Ledge is a spectacular expanded ranch in the desirable Deepwood neighborhood of Chappaqua, which presents sophisticated charm and tranquility. This cedar-shake beauty is perfectly situated at the end of a cul-de-sac on 1.9 acres, offering unparalleled privacy, yet only 5 minutes to the center of town and the Chappaqua Metro-North. The home was renovated between 2000-22 offering years of

Brendan Preston Houlihan Lawrence Inc.

Brand New Construction in the award-winning Chappaqua School District set on over one level acre. Ready for occupancy at the end of July or early August 2025 – just in time for the new school year. With 4 bedrooms and 3.1 bathrooms, it offers a flexible and functional layout with spacious, sunlit interiors that feel welcoming and refined. The open-concept living and dining areas are complemented

Aurora Banaszek Compass Greater NY, LLC

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

Welcome to Mill Stream Farm, privately set on13.7 picture book acres with a sweeping entrance through towering trees, & a terrace with firepit overlooking a scenic pond and stream with waterfall. Experience the magic of a private lake, cascading waterfalls, and your own private mountain range. Historical and breathtaking beauty surrounds this special home. Live your dreams now. The stunning

Sena Baron William Raveis-New York, LLC

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

Over the river and through the woods to 18 Cross River Road, a rare opportunity to live in Riverwoods, one of Westchester’s most desirable luxury townhome communities. Perfectly situated in the Town of New Castle with Chappaqua schools and just minutes to the Village of Mount Kisco, this home offers unmatched convenience to shops, restaurants, a movie theater, major highways, and the Metro North

Justine Flanagan Houlihan Lawrence Inc.

Welcome to 20 Wallace Way – a rare offering in the sold-out Chappaqua Crossings Carriages community. This sophisticated Byram Wetherby model redefines townhouse living with nearly 3,000 sq. ft. of thoughtfully curated interiors, exceptional finishes, and inviting outdoor spaces. Ideally set along an expansive open lawn, the home enjoys abundant sunlight, privacy, and serene views throughout the

Craig DeCecchis Corcoran Legends Realty

Welcome to Hidden Hollow, one of the most sought-after neighborhoods within The Chappaqua School District. This pristine move-in ready four-bedroom Colonial offers the perfect balance of privacy, natural beauty, and convenience as well as access to a private, lifeguarded swimming lake. The home has been meticulously maintained and updated with top quality products and lots of love. From the

Helen Dorman Houlihan Lawrence Inc.

Striking frame and brick-front split-level. Welcoming front-deck. Grand and gracious living room richly adorned with a brick-front, wood-burning fireplace, built-in cabinetry, hardwood flooring, recessed lighting, and three front-facing, sliding glass doors to the deck, which illuminate the space in natural light, let gentle breezes cool the space, and provide easy access for indoor/outdoor

Stacy Levey William Raveis-New York, LLC

A Luxurious Townhouse in the highly sought-after Chappaqua School District with low property taxes.Move right into this 2-3 bedroom + loft, 2.5-bathroom with an Abundanceof oversized closet spaces. The updatedkitchen opens to the oversized living room, with a wood-burning fireplace and sliding glass doors to a private deck and lounge area with a wet-bar. The living room area offers plenty of

Robert Spence

Chappaqua Schools. The Pride of Homeownership Starts Here. Tucked away in the highly sought-after Chappaqua School District, this meticulously maintained Raised Ranch blends comfort, style, and functionality in all the right ways. Step inside to find a bright and open layout—perfect for everyday living and entertaining. The spacious living room flows effortlessly into the dining room with

Yara Annechiarico At Home With Yara Realty

This is the unit you have been waiting for in Riverwoods! Stunning and completely renovated first floor primary bedroom and two car garage unit at the end of a quiet cul de sac in the sought after Riverwoods community in the Chappaqua school district. This maintenance free community is a suburban oasis offering residents access to resort style amenities. Live like you are on vacation in a complex

Amanda Goldberg William Raveis-New York, LLC

Move right in to this 2-bedroom + loft, 2.5-bathroom townhouse in the highly sought-after Chappaqua School District. Freshly painted throughout and updated with brand-new quartz countertops, new dishwasher and new kitchen flooring, this home offers immediate comfort with the flexibility to personalize. The dining area features sliding doors that open to a grassy green space, while the kitchen

Karin Kimtis Compass Greater NY, LLC

Turn Key and Move In Ready! Located in the Nationally Ranked Chappaqua School District! Welcome to this charming, fully renovated home on a bucolic, level 1/2 acre in the desirable Rolling Fields neighborhood. Sun drenched with three finished levels providing a flexible layout. The spacious living room with a cathedral ceiling opening to the kitchen and dining area with a wonderful bay

Usha Subramaniam Compass Greater NY, LLC

Nestled in a tranquil cul-de-sac, this captivating single-family home effortlessly combines historical charm with modern amenities. Set on a third of an acre with lush, mature landscaping for beauty and privacy, the property also features a fenced yard—an ideal space for pets, play, or outdoor relaxation. The antique home, distinguished by its high ceilings and vintage architectural details,

Mark Boyland Keller Williams Realty Partner

Welcome to this beautifully maintained four-bedroom Colonial home nestled in the highly sought-after Chappaqua School District. Offering exclusive lake rights to the serene Hidden Hollow Lake, this exceptional property combines classic charm with modern amenities in a truly picturesque setting.Step inside to discover freshly painted interiors, gleaming hardwood floors, and an abundance of

Wendy Nolan Houlihan Lawrence Inc.

Tucked back on a private corner lot on one of Chappaqua’s most desirable and quiet streets, this expanded mid-century ranch offers a rare opportunity to create your dream home in an award-winning school district. The property is well situated on the lot, leaving plenty of space for a pool or future outdoor expansion.Inside, the home offers a light-filled layout with generously sized

Lindsay Rothman Compass Greater NY LLC

Accepted offer 8/19 Inspections scheduled 8/20 Showing for back-ups only.Discover exceptional living in this well maintained 2-bedroom, 2-bath townhome.A true gem within Chappaqua's coveted Old Farm Lake community. Enjoy lake views from your back deck or use the electric roller shades for the living room view. This unique unit boasts a front lawn, inviting patio, and lush

Clayton Livingston McGrath Realty Inc

Experience the pinnacle of refined living in this newly reimagined modern farmhouse, perfectly sited on a secluded, tree-lined acre in the heart of Chappaqua. With over 2,800 square feet of exquisitely finished space, this residence blends timeless architectural detail with sophisticated, high-end design for the ultimate in quiet luxury. Andersen 400 series windows and doors throughout, most are

Aric Wiser Douglas Elliman Real Estate

All the space and privacy of a single-family home with the ease of condo living! One of the few completely stand-alone and private townhouses in Apple Hill Farm, this spacious 2-bedroom, 2.5-bath home offers a rare blend of comfort, style, and convenience. Enjoy the serene setting from a large wrap-around wood deck overlooking lush, wooded views—perfect for morning coffee or evening entertaining.

Karin Kimtis Compass Greater NY, LLC

Nestled on over 5 private, professionally landscaped acres in the exclusive cul-de-sac of Sutton Farm within Chappaqua’s esteemed Whippoorwill area, this custom-designed and custom-built Shingle Style home is a rare and refined first opportunity. Completed in 2008 by a renowned builder and architect, the 4+ bedroom home (lives like a 5/6) has been meticulously detailed with luxurious, high-end

Cindy Glynn Compass Greater NY, LLC

Move right into this beautifully updated three bedroom, two bathroom ranch, perfectly situated within the award-winning Chappaqua school district. Thoughtfully renovated from top to bottom, this home offers modern comfort and timeless charm. The heart of the home is the stylish kitchen featuring classic oak cabinetry, sleek quartz countertops, and ample space for cooking and entertaining. Both

Alexander Marks William Raveis-New York LLC

Enjoy the highly desirable Riverwoods lifestyle, Chappaqua's premiere upscale condo/townhouse community close to Mt Kisco Village with Chappaqua schools & commute. Easy living in this bright sunny, 3 level end unit with main floor primary bedroom and an elevator. "Lives" like a 4 bedroom with 2 home offices and additional flexible spaces. Versatile floorplan. Renovated kitchen, updated baths,

Sena Baron William Raveis-New York, LLC

Chappaqua Gem—Welcome to 816 Hardscrabble Road located in a Top-Rated School District!Discover your opportunity to live in the coveted Chappaqua School District with this charming 3-bedroom, 2-bath Split-Level Ranch, nestled on a tranquil half acre lot.This home features a spacious Primary En-Suite, offering comfort and privacy. Recent upgrades include Roof, Liters & Gutters

Daniel Berger RE/MAX Prestige Properties

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

Thomas Hennerty

Location, Location, Location. Welcome to the sought-after hamlet of Chappaqua! 29 Meadow Lane is nestled on a charming Cul-De-Sac in a quiet and beautiful neighborhood, this lovely home sitting on over a half-acre offers the perfect blend of comfort, elegance, and versatility. The open concept main floor features a spacious sun-lit dining area, kitchen, living room and sunroom. With 4 bedrooms

Daniel Berger RE/MAX Prestige Properties

Experience the vibrancy and user-friendly vibe of the Hamlet of Chappaqua in this very special move-in ready, end-unit townhouse, which could be the one you’ve been waiting for. Perfectly located, it is walkable to train, schools, restaurants, shops, farmer’s market, town hall, library and more. It offers generous space with flexibility of use featuring two large bedrooms, plus loft, lower level

Nancy Jones Julia B Fee Sothebys Int. Rlty

A truly one-of-a-kind investment opportunity in the sought-after Chappaqua School District—2 houses for the price of one! This eclectic & historic property offers unmatched versatility, character & endless potential. Originally built in 1926 as a horse stable & previously home to a Houlihan Lawrence office, the property has served multiple uses over time, including commercial space & residential

Scott O'Shea Howard Hanna Rand Realty

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

Cindy Glynn Compass Greater NY, LLC

This meticulously designed Colonial in the prestigious Chappaqua Central School District provides a true haven for those who appreciate refined living with a contemporary turnkey design aesthetic. The blend of traditional and contemporary vibes creates an exquisite mix of sophistication and relaxed comfort for entertaining and everyday living. Featuring high-end finishes throughout, every level

Alaina Bainlardi William Raveis-New York LLC

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

Wendy Nolan Houlihan Lawrence Inc.

Stylishly reimagined by two New York fashion VIPs, this sophisticated 1905 Colonial blends modern luxury with the home’s original integrity, grandeur and charm. Tucked away on Hardscrabble Road, the serene sanctuary---a highlight of the New Castle Historical Society house tour—offers a Martha Baker-designed landscape, close to an acre, comprising woodlands, curated boxwoods, flowering dogwoods

Susan Stillman Houlihan Lawrence Inc.

Welcome to 26 Kings Court, Chappaqua, a storybook, village Colonial enchantingly set among towering trees on a quiet cul-de-sac just a short stroll to schools, shops, town and train. If your Brooklyn brownstone could move to the suburbs, this would be it. Regal, barrel-vaulted front portico. Welcoming front entry. French doors introduce the gracious front-facing living room warmed by morning sun

Stacy Levey William Raveis-New York, LLC