Chappaqua, NY Homes

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  /13

  $599,000

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  150 Bedford Rd Unit 12A, Chappaqua, NY 10514

  Welcome to this move-in-ready 2-bedroom, 2-bath residence in highly sought-after Chappaqua Commons. Recently refreshed with thoughtful updates throughout, this sun-filled home combines modern finishes with effortless convenience.The spacious open-concept living and dining area features brand-new flooring (2025) and a seamless flow to the updated kitchen, boasting new countertops and

  Sari Shaw Compass Greater NY, LLC

  150 Bedford Rd Unit 12A, Chappaqua, NY 10514
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  /26

  $2,800 per month

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  150 N Bedford Rd Unit 5A, Chappaqua, NY 10514

  This spacious townhouse is waiting for you to come home! This well-appointed one-bedroom, one-bathroom home will pleasantly surprise you. As you enter the house, a large living area will greet you with polished wooden flooring and plenty of sunlight from the floor-to-ceiling windows. The adjoining kitchen is stylish and practical, with ample wooden cabinets contrasting beautifully with the dark

  Xiao Hua Herman NextHome GoodLife

  150 N Bedford Rd Unit 5A, Chappaqua, NY 10514
• 

  $1,725,000 Sold Oct 31, 2025

  • 4,100 Sq Ft
  • $421/SF
  • 24 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2019

  9 Point Place, Chappaqua, NY 10514

  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

  9 Point Place, Chappaqua, NY 10514
• 

  Est $1,773,072 Not Listed For Sale

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

  55 Cowdin Cir, Chappaqua, NY 10514

  55 Cowdin Cir, Chappaqua, NY 10514
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  /14

  $1,750,000

  • Land
  • 12.92 Acres
  • $135,449 per Acre

  767 King St, Chappaqua, NY 10514

  Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park,

  Sena Baron William Raveis-New York, LLC

  767 King St, Chappaqua, NY 10514
• 

  $2,000,000 Sold Oct 29, 2025

  • 5,234 Sq Ft
  • $382/SF
  • 70 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1929

  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 offer.

  Wendy Nolan Houlihan Lawrence Inc.

  50 Overlook Dr, Chappaqua, NY 10514
• 

  Est $1,757,830 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,689 Sq Ft

  70 Cowdin Cir, Chappaqua, NY 10514

  70 Cowdin Cir, Chappaqua, NY 10514
• 

  

  /21

  $649,000

  • 3 Beds
  • 1.5 Baths
  • 1,292 Sq Ft

  221 N Greeley Ave, Chappaqua, NY 10514

  Fantastic opportunity just steps from downtown Chappaqua. Only a short three minute walk to the heart of town, this property sits on a generous lot with great outdoor space and endless potential. Currently used as a single family home, the Business Retail zoning allows for a variety of uses whether you are an investor, looking for a live work setup, or considering a residential conversion. An

  Robert Dellaero Julia B Fee Sothebys Int. Rlty

  221 N Greeley Ave, Chappaqua, NY 10514
• 

  $1,175,000 Sold Oct 27, 2025

  • 2,695 Sq Ft
  • $436/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  495 Quaker Rd, Chappaqua, NY 10514

  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

  495 Quaker Rd, Chappaqua, NY 10514
• 

  Est $2,513,678 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,600 Sq Ft

  76 Cowdin Ln, Chappaqua, NY 10514

  76 Cowdin Ln, Chappaqua, NY 10514
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  /48

  $1,375,000

  • 4 Beds
  • 2.5 Baths
  • 2,541 Sq Ft

  341 Millwood Rd, Chappaqua, NY 10514

  Discover the perfect balance of modern design and peaceful living at 341 Millwood Road. Set on nearly 2 acres of wooded privacy within the Chappaqua School District, this completely renovated 4-bedroom, 2.5-bath Raised Ranch has been transformed from top to bottom. Every detail shines - from new flooring, doors, moldings, lighting, and baths to a stunning eat-in kitchen with GE Cafe

  Lauren Zaccaria Houlihan Lawrence Inc.

  341 Millwood Rd, Chappaqua, NY 10514
• 

  $1,391,022 Sold Oct 23, 2025

  • 3,776 Sq Ft
  • $368/SF
  • 30 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1952

  6 Algonquin Dr, Chappaqua, NY 10514

  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

  6 Algonquin Dr, Chappaqua, NY 10514
• 

  Est $3,151,445 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 7,764 Sq Ft

  63 Cowdin Ln, Chappaqua, NY 10514

  63 Cowdin Ln, Chappaqua, NY 10514
• 

  

  /20

  $475,000

  • 1 Bed
  • 1.5 Baths
  • 1,207 Sq Ft

  356 N Greeley Ave Unit 28G, Chappaqua, NY 10514

  Location, Location, Location! Chestnut Oak Complex. Dramatic and bright townhouse with natural lighting. This 1 bedroom 1.1 bath plus huge Loft/Den is in mint condition. Updated kitchen with stainless-steel appliances. Living room with high ceilings, fireplace and wall of windows is combined with spacious dining area. Updated powder room on the first level. Huge primary bedroom with with two

  Alicja Bohmrich Houlihan Lawrence Inc.

  356 N Greeley Ave Unit 28G, Chappaqua, NY 10514
• 

  $775,000 Sold Oct 22, 2025

  • 1,549 Sq Ft
  • $500/SF
  • 42 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  77 Further Ln, Chappaqua, NY 10514

  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 Premier Real Estate

  77 Further Ln, Chappaqua, NY 10514
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  Est $2,020,701 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 5,309 Sq Ft

  70 Cowdin Ln, Chappaqua, NY 10514

  70 Cowdin Ln, Chappaqua, NY 10514
• 

  

  /21

  $2,850,000

  • 4 Beds
  • 7 Baths
  • 5,536 Sq Ft

  211 Bedford Rd, Chappaqua, NY 10514

  Exciting and new state-of-the-art expansion and renovation by highly recognized local developer, Tavo Development teaming with noted architect Teo Seguenza. Ready for occupancy in Spring 2026. Meticulous attention to detail, years of experience and master craftsmanship are combined in this new offering, encompassing 5,536 sq ft, 4 bedrooms, 5 full and 2 half baths, a finished walk-out lower level

  Brian Milton Compass Greater NY, LLC

  211 Bedford Rd, Chappaqua, NY 10514
• 

  $1,646,500 Sold Oct 21, 2025

  • 2,550 Sq Ft
  • $646/SF
  • 17 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1914

  59 Crest Rd, Chappaqua, NY 10514

  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

  59 Crest Rd, Chappaqua, NY 10514
• 

  Est $1,267,875 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,137 Sq Ft

  45 Jeffrey Ln, Chappaqua, NY 10514

  45 Jeffrey Ln, Chappaqua, NY 10514
• 

  

  /35

  $3,450,000

  • 6 Beds
  • 5.5 Baths
  • 8,200 Sq Ft

  20 Bessel Ln, Chappaqua, NY 10514

  Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides

  Tianying Xu Houlihan Lawrence Inc.

  20 Bessel Ln, Chappaqua, NY 10514
• 

  $525,000 Sold Oct 16, 2025

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

  • 3 Beds
  • 2 Baths
  • Built 1927

  380 Whippoorwill Rd, Chappaqua, NY 10514

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

  Sari Shaw Compass Greater NY, LLC

  380 Whippoorwill Rd, Chappaqua, NY 10514
• 

  Est $1,365,497 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,356 Sq Ft

  416 Bedford Rd, Chappaqua, NY 10514

  416 Bedford Rd, Chappaqua, NY 10514
• 

  

  /22

  $669,000

  • 2 Beds
  • 2.5 Baths
  • 1,479 Sq Ft

  10 Grove Mews, Chappaqua, NY 10514

  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

  10 Grove Mews, Chappaqua, NY 10514
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  $1,075,000 Sold Oct 10, 2025

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

  • 4 Beds
  • 2.5 Baths
  • Built 1981

  21 Kipp St, Chappaqua, NY 10514

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

  Vanessa Catalano Julia B Fee Sothebys Int. Rlty

  21 Kipp St, Chappaqua, NY 10514
• 

  Est $2,347,542 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 5,098 Sq Ft

  1186 Hardscrabble Rd, Chappaqua, NY 10514

  1186 Hardscrabble Rd, Chappaqua, NY 10514
• 

  

  /21

  $1,099,000

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  10 Barnes Ln, Chappaqua, NY 10514

  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

  10 Barnes Ln, Chappaqua, NY 10514
• 

  $1,800,000 Sold Oct 09, 2025

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

  • 5 Beds
  • 4.5 Baths
  • Built 1991

  73 Random Farms Dr, Chappaqua, NY 10514

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

  Alicja Bohmrich Houlihan Lawrence Inc.

  73 Random Farms Dr, Chappaqua, NY 10514
• 

  Est $2,542,442 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 6,187 Sq Ft

  31 Hemlock Hills, Chappaqua, NY 10514

  31 Hemlock Hills, Chappaqua, NY 10514
• 

  $1,699,000 New Construction

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

  Greeley Newhaven Plan at Chappaqua Crossing Carriages, Chappaqua, NY 10514

  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

  Toll Brothers, Inc. Builder

  19 Wallace Way Unit 36358705, Chappaqua, NY 10514
• 

  $2,300,000 Sold Oct 08, 2025

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

  • 5 Beds
  • 4.5 Baths
  • Built 2000

  3 Boulder Trail, Chappaqua, NY 10514

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

  Nancy Strong Douglas Elliman Real Estate

  3 Boulder Trail, Chappaqua, NY 10514
• 

  Est $2,779,363 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 6,422 Sq Ft

  6 Hemlock Hollow, Chappaqua, NY 10514

  6 Hemlock Hollow, Chappaqua, NY 10514
• 

  

  /29

  $1,199,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,069 Sq Ft

  111 Seven Bridges Rd, Chappaqua, NY 10514

  Welcome to this sparkling sun-filled ranch, this beautifully updated 4 bedroom/2.1 bath home offers an easy living floorplan, lovely landscaped property and easy access to top rated schools, shops and commuter train. Over 2000 sq ft, on an acre, offering privacy amidst a neighborhood feel. Newly renovated bathrooms, updated kitchen, freshly painted interior, and gleaming newly refinished white

  Sena Baron William Raveis-New York, LLC

  111 Seven Bridges Rd, Chappaqua, NY 10514
• 

  $1,275,000 Sold Oct 06, 2025

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

  • 3 Beds
  • 2.5 Baths
  • Built 1952

  4 Southview Rd, Chappaqua, NY 10514

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

  Wendy Nolan Houlihan Lawrence Inc.

  4 Southview Rd, Chappaqua, NY 10514
• 

  Est $3,079,027 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 6,083 Sq Ft

  3 Trails End, Chappaqua, NY 10514

  3 Trails End, Chappaqua, NY 10514
• 

  

  /39

  $1,425,000 Pending

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

  71 Commodore Rd, Chappaqua, NY 10514

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

  Cindy Glynn Compass Greater NY, LLC

  71 Commodore Rd, Chappaqua, NY 10514
• 

  $1,275,000 Sold Oct 03, 2025

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

  • 5 Beds
  • 3 Baths
  • Built 1964

  26 Mayberry Rd, Chappaqua, NY 10514

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

  Edward Holmes William Raveis-New York, LLC

  26 Mayberry Rd, Chappaqua, NY 10514
• 

  Est $2,768,990 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 7,624 Sq Ft

  6 Trails End, Chappaqua, NY 10514

  6 Trails End, Chappaqua, NY 10514
• 

  

  /40

  $1,300,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,971 Sq Ft

  100 Old Farm Rd N, Chappaqua, NY 10514

  Chappaqua Schools! This immaculately maintained 3-bedroom stone and shingle Colonial is gracefully sited on nearly an acre of professionally landscaped grounds, offering exceptional privacy and tranquility. A charming stone portico welcomes you at the front entry, setting the tone for the elegant interiors that follow. Sun-drenched spaces and an open-concept layout create an inviting and seamless

  Wendy Nolan Houlihan Lawrence Inc.

  100 Old Farm Rd N, Chappaqua, NY 10514
• 

  $1,660,000 Sold Oct 03, 2025

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

  • 5 Beds
  • 4.5 Baths
  • Built 1993

  43 Random Farms Cir, Chappaqua, NY 10514

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

  Suzan Zeolla Houlihan Lawrence Inc.

  43 Random Farms Cir, Chappaqua, NY 10514
• 

  Est $813,089 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft

  15 Paula Place, Chappaqua, NY 10514

  15 Paula Place, Chappaqua, NY 10514

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