Westchester, NY Homes

• 

  

  

  /35

  $1,350,000 Pending

  • 6 Beds
  • 4 Baths
  • 5,034 Sq Ft

  62 Taconic Rd, Millwood, NY 10546

  MOTIVATED SELLER! PRICE REDUCED! Welcome to this spacious, peaceful, and impeccably maintained 6-bedroom, 4-bathroom home with tennis court and pool in the highly sought-after Chappaqua School District (Millwood). This home offers 5,034 sq ft of move-in ready living space on a scenic and private 2-acre lot. The large rooms and easy layout provide the perfect canvas to create your dream home

  

  Hillary Landau

  Compass Greater NY, LLC

  (914) 996-2889

  62 Taconic Rd, Millwood, NY 10546
• 

  

  

  /12

  $9,400 per month

  • 4 Beds
  • 3.5 Baths
  • 2,468 Sq Ft
  • House for Rent

  187 Croton Ave, Mount Kisco, NY 10549

  Move right in to this bright and sunny recently renovated 4 bedroom home in the Chappaqua School District. Enjoy easy living and a great layout for entertaining family and friends. Open concept kitchen - family room with access to wrap around deck and great yard. 1st floor primary with renovated en-suite, walk in closet and sliders to deck, living room, dining room and powder room complete the

  

  Deena Bouchier

  Compass Greater NY, LLC

  (914) 814-6734

  187 Croton Ave, Mount Kisco, NY 10549
• 

  $2,282,000 Sold Aug 11, 2025

  • 5,254 Sq Ft
  • $434/SF
  • 17 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 1990

  92 Random Farms Dr, Chappaqua, NY 10514

  Welcome to 92 Random Farms Drive, ideally located in the sought-after Random Farms community of Chappaqua. Completely renovated in 2022, this stunning turnkey residence showcases modern design, luxurious upgrades, and an open layout tailored to today’s lifestyle.The main level features a dramatic double-height entry foyer, a gourmet kitchen outfitted with premium appliances, a sunlit living

  Sari Shaw Compass Greater NY, LLC

  92 Random Farms Dr, Chappaqua, NY 10514
• 

  Est $920,596 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,688 Sq Ft

  16 Seth Canyon Dr, Mount Kisco, NY 10549

  16 Seth Canyon Dr, Mount Kisco, NY 10549
• 

  

  

  /27

  $210,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  135 - 6 Highland Ave S Unit D1, Ossining, NY 10562

  Discover this charming, updated two-bedroom co-op in highly sought-after Highland Terrace. This unique unit offers the convenience of both a main building entrance and its own private entry. Inside, you'll find a spacious and bright primary bedroom with ample closet space, while the versatile second bedroom That is currently being utilized as a home office. Abundant windows fill the living areas

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 601-2993

  135 - 6 Highland Ave S Unit D1, Ossining, NY 10562
• 

  

  /25

  $2,400 - $6,850 per month

  Chappaqua Crossing Apartments

  1 - 3 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
• 

  $1,825,000 Sold Aug 11, 2025

  • 3,814 Sq Ft
  • $479/SF
  • 7 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1956

  33 W Orchard Rd, Chappaqua, NY 10514

  Beautiful, spacious, completely renovated three bedroom, four bathroom ranch style home that lives like a five bedroom on a quiet cul-de-sac neighborhood street in the Chappaqua school district. This home has undergone a comprehensive renovation in the last 8 years where every detail has been carefully crafted to blend sophistication, elegance, and functionality. The rear private yard

  Amanda Goldberg William Raveis-New York, LLC

  33 W Orchard Rd, Chappaqua, NY 10514
• 

  Est $666,647 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,918 Sq Ft

  36 Ledgewood Commons, Millwood, NY 10546

  36 Ledgewood Commons, Millwood, NY 10546
• 

  

  /49

  $2,200,000

  • 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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  /32

  $5,600 per month

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft
  • Townhouse for Rent

  44 Brook Farm Close Unit 44, Chappaqua, NY 10514

  Old Farm Lake Condo complex - Recent renovation includes new porcelain tiled entry and Kitchen floors, new white eat-in kitchen with quartz counters. range, refrigerator and DW. This 2 Bedroom unit has been freshly painted, new lighting fixtures, Washer & Dryer on second floor, each bedroom has a full bath, wood floors throughout and new windows, Primary BR has a large walk-in closet, Enter

  Janet Auer Coldwell Banker Realty

  44 Brook Farm Close Unit 44, Chappaqua, NY 10514
• 

  $1,090,000 Sold Aug 08, 2025

  • 1,874 Sq Ft
  • $582/SF
  • 34 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1955

  83 Inningwood Rd, Millwood, NY 10546

  Newly staged and a pleasure to show! Perched gracefully on a hill, this striking mid-century modern home is a testament to architect Aaron Resnick’s creative vision, shaped under the mentorship of Frank Lloyd Wright. Embracing the philosophy that architecture should harmonize with its surroundings, the design flows seamlessly with the natural topography rather than imposing upon it.With all

  Amy Via Houlihan Lawrence Inc.

  83 Inningwood Rd, Millwood, NY 10546
• 

  Not Listed For Sale

  • 4 Beds

  767 King St, Chappaqua, NY 10514

  767 King St, Chappaqua, NY 10514
• 

  

  /44

  $1,774,000

  • 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
• 

  

  /11

  $3,700 per month

  • 1 Bed
  • 2 Baths
  • 884 Sq Ft
  • Apartment for Rent

  91 Bedford Rd Unit 3, Chappaqua, NY 10514

  LIVES LIKE A TWO-BEDROOM. Master bed/bath, Den/bed. High Ceilings. Quality construction by highly regarded local builder. Glamorous modern styling: quartz counters, bright open floor plans, LED lighting, + individual balcony, storage closet. HW/heater & W/D. Amenities of this architecturally inspired bldg include Access control intercom/security cameras., FOB. Steel & concrete frame, rock wool

  Grace Priore ERA Insite Realty Services

  91 Bedford Rd Unit 3, Chappaqua, NY 10514
• 

  $1,890,000 Sold Aug 08, 2025

  • 4,561 Sq Ft
  • $414/SF
  • 7 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1785

  42 Seven Bridges Rd, Chappaqua, NY 10514

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

  Sena Baron William Raveis-New York, LLC

  42 Seven Bridges Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,477 Sq Ft

  38 Taylor Rd, Mount Kisco, NY 10549

  38 Taylor Rd, Mount Kisco, NY 10549
• 

  

  /9

  $1,807,995 Pending

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft

  2 Carriage Ln Unit 81, Chappaqua, NY 10514

  HOME IS TO BE BUILT. 2 BR very popular Greeley Floorplan with primary on first floor. We have a model of this home to walk through. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner

  Thomas Jacovino Toll Brothers Real Estate Inc.

  2 Carriage Ln Unit 81, Chappaqua, NY 10514
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  /12

  $4,500 per month

  • 2 Beds
  • 2.5 Baths
  • 1,408 Sq Ft
  • Townhouse for Rent

  82 Pheasant Run Unit 82B, Millwood, NY 10546

  Welcome to this beautifully updated 2-bedroom, 2.5-bath condo in the desirable Pheasant Run community. Located in the Chappaqua School District, this home offers the perfect blend of comfort, convenience, and lifestyle.The main level offers a welcoming layout with an eat-in kitchen that opens to the spacious living and dining area—ideal for entertaining. Enjoy cozy evenings by the

  Jill Urban Compass Greater NY, LLC

  82 Pheasant Run Unit 82B, Millwood, NY 10546
• 

  $1,325,000 Sold Aug 07, 2025

  • 2,665 Sq Ft
  • $497/SF
  • 27 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1972

  51 Hidden Hollow Ln, Millwood, NY 10546

  How about a picture-perfect, 4 bedroom, 2 1/2 bath colonial privately nestled behind a small stand of trees and offering a backyard paradise? Plus, it’s move-in ready. From the moment you turn down the spacious driveway, step out of your car, and walk up to the porticoed front entrance, you will have a lot to look forward to upon stepping inside. Open the front door and you’ll find yourself

  Mary Case Friedner Corcoran Legends Realty

  51 Hidden Hollow Ln, Millwood, NY 10546
• 

  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
• 

  

  /35

  $2,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,004 Sq Ft

  4 Circle Dr, Mount Kisco, NY 10549

  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

  4 Circle Dr, Mount Kisco, NY 10549
• 

  

  /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
• 

  $1,445,000 Sold Aug 07, 2025

  • 2,652 Sq Ft
  • $545/SF
  • 5 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1951

  12 Pond Hill Rd, Chappaqua, NY 10514

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

  Jennifer Harris Compass Greater NY, LLC

  12 Pond Hill Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,427 Sq Ft

  16 Maria Ln, Ossining, NY 10562

  16 Maria Ln, Ossining, NY 10562
• 

  

  /16

  $1,450,000

  • 4 Beds
  • 5 Baths
  • 2,875 Sq Ft

  136 Roaring Brook Rd, Chappaqua, NY 10514

  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

  136 Roaring Brook Rd, Chappaqua, NY 10514
• 

  

  /24

  $9,750 per month

  • 4 Beds
  • 3.5 Baths
  • 3,882 Sq Ft
  • House for Rent

  777 Armonk Rd, Mount Kisco, NY 10549

  Set on over five secluded acres with picturesque pond and woodland views, this beautifully furnished 4-bedroom home offers a perfect blend of timeless character and modern comfort. Ideal for short- or long-term stays, the residence is thoughtfully designed for both relaxation and functionality.The main level welcomes you with a gracious entry foyer, a chef’s kitchen with premium

  Mark Sanford Berkshire Hathaway HS NE Prop.

  777 Armonk Rd, Mount Kisco, NY 10549
• 

  $1,560,000 Sold Aug 07, 2025

  • 2,246 Sq Ft
  • $695/SF
  • 10 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1935

  45 Crossways, Chappaqua, NY 10514

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

  Stacy Levey William Raveis-New York, LLC

  45 Crossways, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 3,853 Sq Ft

  229 Pinesbridge Rd, Ossining, NY 10562

  229 Pinesbridge Rd, Ossining, NY 10562
• 

  

  /36

  $1,795,000

  • 4 Beds
  • 3.5 Baths
  • 4,576 Sq Ft

  20 Little Pine Rd, Mount Kisco, NY 10549

  Located at the end of a quiet cul-de-sac, 20 Little Pine Road is a Modern Farmhouse Colonial situated on over an acre of beautifully landscaped grounds. Interior spaces are light and fresh with a wonderful floorplan for everyday living. Approximately 4600 square feet, it houses nine main rooms on two levels. There is additional finished living space in the walk-out lower level. Interior spaces

  Mary Dowdle Ginnel Real Estate

  20 Little Pine Rd, Mount Kisco, NY 10549
• 

  

  /35

  $5,700 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
• 

  $875,000 Sold Aug 06, 2025

  • 2,541 Sq Ft
  • $344/SF
  • 32 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1964

  341 Millwood Rd, Chappaqua, NY 10514

  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

  Jo Ann Reilly Julia B Fee Sothebys Int. Rlty

  341 Millwood Rd, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 8 Beds
  • 8 Baths
  • 5,337 Sq Ft

  51 Pinesbridge Rd, Ossining, NY 10562

  51 Pinesbridge Rd, Ossining, NY 10562
• 

  

  /43

  $2,000,000

  • 6 Beds
  • 6 Baths
  • 5,234 Sq Ft

  50 Overlook Dr, Chappaqua, NY 10514

  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

  Wendy Nolan Houlihan Lawrence Inc.

  50 Overlook Dr, 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
• 

  $1,615,000 Sold Aug 01, 2025

  • 4,099 Sq Ft
  • $394/SF
  • 13 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1985

  7 High Point Cir, Chappaqua, NY 10514

  Beautifully positioned at the end of a quiet cul-de-sac, this contemporary home offers style and serenity in a prime Chappaqua location. Designed with today’s lifestyle in mind, the open and airy floor plan features soaring ceilings, floor-to-ceiling windows, and sun-drenched spaces throughout. A beautifully updated modern kitchen flows seamlessly into expansive living and dining areas, ideal for

  Cindy Glynn Compass Greater NY, LLC

  7 High Point Cir, Chappaqua, NY 10514
• 

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,644 Sq Ft

  130 Pinesbridge Rd, Ossining, NY 10562

  130 Pinesbridge Rd, Ossining, NY 10562
• 

  

  /34

  $1,799,999

  • 4 Beds
  • 3 Baths
  • 3,009 Sq Ft

  200 Millwood Rd, Chappaqua, NY 10514

  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,

  Sari Shaw Compass Greater NY, LLC

  200 Millwood Rd, Chappaqua, NY 10514
• 

  

  /17

  $4,995 per month

  • 3 Beds
  • 1.5 Baths
  • 2,200 Sq Ft
  • Apartment for Rent

  52 Orchard Ridge Rd, Chappaqua, NY 10514

  Multi-level home featuring large rms and open plan kitch/dining area. Bdrm's are located upstairs and are well sized with beautiful crown molding and large closets. Large, flat backyard perfect for play, outdoor BBQ & entertaining includes your own small garden to grow fresh vegetables for the family. Kitchen with granite countertops, natural gas stove and stainless steel appliances. Mudroom and

  Valon Nikci Link NY Realty

  52 Orchard Ridge Rd, Chappaqua, NY 10514
• 

  $600,000 Sold Aug 01, 2025

  • 1,608 Sq Ft
  • $373/SF
  • 28 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  324 N Greeley Ave, Chappaqua, NY 10514

  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

  Nick Rie K. Fortuna Realty, Inc.

  324 N Greeley Ave, Chappaqua, NY 10514
• 

  Est $1,569,374 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,973 Sq Ft

  370 Sarles St, Mount Kisco, NY 10549

  370 Sarles St, Mount Kisco, NY 10549

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