Chappaqua, NY Homes

• 

  Est $2,008,269

  Not Listed For Sale

  70 Cowdin Cir, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 3,689 Sq Ft
  • Built 1963

  70 Cowdin Cir, Chappaqua, NY 10514

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.
• 

  

  

  /25

  $890,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,569 Sq Ft

  20 Waters Edge, Chappaqua, NY 10514

  Welcome to Old Farm Lake - one of Chappaqua's most desirable condominium communities, offering low-maintenance living with resort-style amenities. This 3-bedroom, 2.5-bath townhome is set in a private setting and lives beautifully with natural light across three levels. The main level features an open living and dining area with cathedral ceilings, a skylight, and a wood-burning fireplace. The

  Edward Holmes William Raveis-New York, LLC

  20 Waters Edge, Chappaqua, NY 10514
• 

  $799,000

  Sold Aug 05, 2026

  127 Stone Bridge Square Unit 127, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,244 Sq Ft
  • Built 1986

  Last Sold Summary

  • $642/SF
  • 11 Days On Market

  Current Estimated Value $799,865

  Last Listing Agent Victoria Miller Compass Greater NY, LLC

  127 Stone Bridge Square Unit 127, Chappaqua, NY 10514
• 

  Est $1,751,550

  Not Listed For Sale

  64 Cowdin Cir, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,911 Sq Ft
  • Built 1962

  64 Cowdin Cir, Chappaqua, NY 10514

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.
• 

  

  

  /31

  $725,000

  Pending

  • 2 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  134 Bayberry Close Unit 134, Chappaqua, NY 10514

  Welcome to 134 Bayberry Close in the sought-after Old Farm Lake community, in the heart of Chappaqua. This spacious 2-bedroom, 2.5-bathroom townhouse offers over 1,800 sq ft of living space across three levels, including a finished walk-out lower level. The main level features an eat-in kitchen, a dining area with sliding glass doors to the deck, and a sun-filled living room with cathedral

  Mark Boyland Keller Williams Realty Partner

  134 Bayberry Close Unit 134, Chappaqua, NY 10514
• 

  $1,620,000

  Sold Jun 17, 2026

  25 Longview Ln, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,193 Sq Ft
  • Built 1979

  Last Sold Summary

  • 25% Above List Price
  • $507/SF
  • 12 Days On Market

  Current Estimated Value $1,467,231

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  25 Longview Ln, Chappaqua, NY 10514
• 

  Est $2,733,935

  Not Listed For Sale

  76 Cowdin Ln, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,600 Sq Ft
  • Built 1962

  76 Cowdin Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Yona Strougo Compass Greater NY, LLC
• 

  

  /49

  $1,595,000

  Pending

  • 7 Beds
  • 3 Baths
  • 5,200 Sq Ft

  52 Orchard Ridge Rd, Chappaqua, NY 10514

  Rare opportunity to own two side-by-side residences on a beautifully landscaped 0.45-acre property in the highly sought-after Chappaqua School District. 52 Orchard Ridge features a renovated 3-bedroom, 1.5-bath home with hardwood floors, stainless steel appliances, updated cabinetry and countertops, and in-unit laundry. This residence will be delivered vacant at closing, offering immediate

  Valon Nikci Link NY Realty

  52 Orchard Ridge Rd, Chappaqua, NY 10514
• 

  $999,000

  Sold Aug 18, 2025

  326 Millwood Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 2,313 Sq Ft
  • Built 1924

  Last Sold Summary

  • $432/SF
  • 3 Days On Market

  Current Estimated Value $1,169,432

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  326 Millwood Rd, Chappaqua, NY 10514
• 

  Est $3,360,018

  Not Listed For Sale

  63 Cowdin Ln, Chappaqua, NY 10514

  • 4 Beds
  • 5.5 Baths
  • 7,764 Sq Ft
  • Built 2007

  63 Cowdin Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  

  /42

  $2,650,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 4,975 Sq Ft

  3 Pondfield Dr S, Chappaqua, NY 10514

  Welcome to an exceptional move-in ready home located in a highly desirable Chappaqua neighborhood known for its award-winning schools & sought-after lifestyle. Perfectly positioned at the end of a quiet cul-de-sac, this stunning & chic property offers privacy, space & luxury living at its finest. Step inside & you'll find a bright, open-concept floor plan with natural light & high-end finishes

  Lori Meringolo Houlihan Lawrence Inc.

  3 Pondfield Dr S, Chappaqua, NY 10514
• 

  $2,635,000

  Sold Aug 25, 2025

  8 Turtleback Way, Chappaqua, NY 10514

  • 5 Beds
  • 4.5 Baths
  • 6,649 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Above List Price
  • $396/SF
  • 10 Days On Market

  Current Estimated Value $2,695,335

  Last Listing Agent Michele Iasich-Pagnotta Houlihan & O'Malley R. E. Serv

  8 Turtleback Way, Chappaqua, NY 10514
• 

  Est $2,339,947

  Not Listed For Sale

  70 Cowdin Ln, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 5,309 Sq Ft
  • Built 1987

  70 Cowdin Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 97 Days On Market

  Last Listing Agent Suzanne Sanborn William Raveis Real Estate
• 

  

  /38

  $1,925,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 4,489 Sq Ft

  1 Hitching Post Ln, Chappaqua, NY 10514

  Welcome to this warm, inviting 5-bedroom home nestled on a tree-lined beautiful Chappaqua street. It has a lovely front porch with plenty of room for cozy chairs, perfect for sipping coffee in the morning. Inside, there is a spacious living room with a wood burning fireplace, a bright kitchen and a large island. First floor features a Primary Suite, 4 additional bedrooms with 2 full baths

  Yona Strougo Compass Greater NY, LLC

  1 Hitching Post Ln, Chappaqua, NY 10514
• 

  $1,290,000

  Sold Jan 21, 2026

  71 Commodore Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft
  • Built 1955

  Last Sold Summary

  • 11% Below List Price
  • $659/SF
  • 37 Days On Market

  Current Estimated Value $1,314,792

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  71 Commodore Rd, Chappaqua, NY 10514
• 

  Est $1,715,117

  Not Listed For Sale

  9 Killington St, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 2,625 Sq Ft
  • Built 1968

  9 Killington St, Chappaqua, NY 10514

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Natalia Wixom Compass Greater NY, LLC
• 

  

  /35

  $549,000

  $301K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 711 Sq Ft

  58 Maple Ave, Chappaqua, NY 10514

  Opportunities like this do not come around often in Chappaqua, and when they do, they tend to move quickly. What is being offered at 58 Maple Ave is a flat, level, in-town parcel with an existing 2-bedroom, 1-bath cottage set back from the road among towering pines, in one of Westchester County's most coveted villages. Whether a buyer chooses to develop the land, renovate what is there, or simply

  Christian Lugo Howard Hanna Rand Realty

  58 Maple Ave, Chappaqua, NY 10514
• 

  $2,025,000

  Sold Jul 22, 2026

  40 Kings Ct, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 3,121 Sq Ft
  • Built 1939

  Last Sold Summary

  • 27% Above List Price
  • $649/SF
  • 13 Days On Market

  Current Estimated Value $1,587,092

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC

  40 Kings Ct, Chappaqua, NY 10514
• 

  Est $1,770,061

  Not Listed For Sale

  395 Bedford Rd, Chappaqua, NY 10514

  • 5 Beds
  • 3.5 Baths
  • 3,041 Sq Ft
  • Built 1955

  395 Bedford Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Catherine O'Connor Houlihan Lawrence Inc.
• 

  

  /29

  $790,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,538 Sq Ft

  220 Mill River Rd, Chappaqua, NY 10514

  Straight from the pages of a storybook, this enchanting French Revival Tudor-inspired home is tucked amongst a canopy of mature trees and natural stone walls which create an unforgettable first impression. A winding stone walkway leads to a charming covered entry highlighted by a stained glass front door, hinting at the warmth and character that await inside. Living room with fireplace, eat-in

  Beth Silfen Compass Greater NY, LLC

  220 Mill River Rd, Chappaqua, NY 10514
• 

  $2,000,000

  Sold Feb 09, 2026

  2 Whippoorwill Close, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,022 Sq Ft
  • Built 1980

  Last Sold Summary

  • 14% Above List Price
  • $662/SF
  • 4 Days On Market

  Current Estimated Value $1,956,749

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  2 Whippoorwill Close, Chappaqua, NY 10514
• 

  Est $2,707,571

  Not Listed For Sale

  35 Ivy Hill Rd, Chappaqua, NY 10514

  • 5 Beds
  • 4.5 Baths
  • 4,004 Sq Ft
  • Built 1942

  35 Ivy Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Stacy Levey William Raveis-New York, LLC
• 

  

  /36

  $1,975,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 4,166 Sq Ft

  111 Prospect Dr, Chappaqua, NY 10514

  Exquisite architectural design, timeless charm & luxurious modern amenities merge effortlessly in this elegant Colonial in the heart of Chappaqua. C.1902 & superbly upgraded and meticulously maintained, the home offers an open, sun-bathed interior w/hardwood floors, high ceilings, abundant built-ins, extensive millwork and a quintessential porch - sure to please the most discerning buyers! The

  Usha Subramaniam Compass Greater NY, LLC

  111 Prospect Dr, Chappaqua, NY 10514
• 

  $1,455,000

  Sold Jul 22, 2026

  28 Valley View Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft
  • Built 1956

  Last Sold Summary

  • 32% Above List Price
  • $728/SF
  • 9 Days On Market

  Current Estimated Value $1,119,928

  Last Listing Agent Kile Boga-Ibric Houlihan Lawrence Inc.

  28 Valley View Rd, Chappaqua, NY 10514
• 

  Est $2,802,316

  Not Listed For Sale

  17 Colony Row, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,680 Sq Ft
  • Built 1965

  17 Colony Row, Chappaqua, NY 10514

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  

  /30

  $750,000

  Pending

  • 2 Beds
  • 2.5 Baths
  • 1,653 Sq Ft

  110 Woods End Rd Unit 110, Chappaqua, NY 10514

  Offering over 1650SF of living space, this spacious townhouse in the sought-after Old Farm Lake community has private wooded views and an open, light-filled floor plan. The living room which is open to the dining area, features cathedral ceilings, a wood-burning fireplace, and sliding glass doors to a private deck. A renovated eat-in kitchen is well- appointed with granite countertops and

  Amy Singer Houlihan Lawrence Inc.

  110 Woods End Rd Unit 110, Chappaqua, NY 10514
• 

  $1,720,000

  Sold Feb 04, 2026

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,244 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Above List Price
  • $530/SF
  • 25 Days On Market

  Current Estimated Value $1,785,288

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514
• 

  Est $1,494,552

  Not Listed For Sale

  416 Bedford Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 2,356 Sq Ft
  • Built 1952

  416 Bedford Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Edward Holmes William Raveis-New York, LLC
• 

  

  /35

  $1,299,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,096 Sq Ft

  14 Garey Dr, Chappaqua, NY 10514

  Completely reimagined and move-in ready, this sun-filled 3-bedroom plus home office, 2.5-bath home sits on over one acre of rare, level property in one of Chappaqua’s most sought-after neighborhoods. Blending modern updates with timeless design, the home offers a bright, open flow ideal for today’s lifestyle, with expansive windows that flood every room with natural light. The main level

  Whitney Bagliebter Compass Greater NY, LLC

  14 Garey Dr, Chappaqua, NY 10514
• 

  $1,679,000

  Sold Sep 18, 2025

  10 Carriage Ln Unit 85, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft
  • Built 2025

  Last Sold Summary

  • $514/SF
  • 137 Days On Market

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

  10 Carriage Ln Unit 85, Chappaqua, NY 10514
• 

  Est $3,138,186

  Not Listed For Sale

  26 Hemlock Hills, Chappaqua, NY 10514

  • 5 Beds
  • 6.5 Baths
  • 7,038 Sq Ft
  • Built 1989

  26 Hemlock Hills, Chappaqua, NY 10514

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Wendy Alper Julia B Fee Sothebys Int. Rlty
• 

  

  /17

  $649,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  353 N Greeley Ave Unit 353, Chappaqua, NY 10514

  Welcome to Chestnut Oaks. Corner unit Townhome located in building 5 featuring 2 bedrooms, 2 full baths, fireplace, attached garage and balcony. Located in the heart of Chappaqua and close to train, town and schools. Renovated in 2010 with new dine-in kitchen, granite counter tops, stainless steel appliances, hardwood floors, renovated primary bathroom, custom walk-in closet, new washer/dryer and

  Toni DiMichelo Houlihan Lawrence Inc.

  353 N Greeley Ave Unit 353, Chappaqua, NY 10514
• 

  $2,000,000

  Sold Apr 28, 2026

  40 Smith St, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,658 Sq Ft
  • Built 1927

  Last Sold Summary

  • 38% Above List Price
  • $752/SF
  • 7 Days On Market

  Current Estimated Value $1,830,770

  Last Listing Agent Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  40 Smith St, Chappaqua, NY 10514
• 

  Est $2,767,687

  Not Listed For Sale

  31 Hemlock Hills, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 6,187 Sq Ft
  • Built 1989

  31 Hemlock Hills, Chappaqua, NY 10514

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Judith Kelly Houlihan Lawrence Inc.
• 

  

  /30

  $1,590,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,690 Sq Ft

  131 Douglas Rd, Chappaqua, NY 10514

  Enter into this enduring Colonial blending elegance with today's lifestyle. This home lives like a 4-bedroom and has 4 BR septic. Set on beautifully landscaped property moments away from town, the train and Chappaqua schools. Tastefully expanded and renovated in 2008, this home showcases classic architectural details everywhere. A welcoming foyer opens to a gracious living room and fireplace. A

  Toni DiMichelo Houlihan Lawrence Inc.

  131 Douglas Rd, Chappaqua, NY 10514
• 

  $1,320,000

  Sold Dec 11, 2025

  41 Valley Ln, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 1972

  Last Sold Summary

  • 2% Above List Price
  • $649/SF
  • 10 Days On Market

  Current Estimated Value $1,365,768

  Last Listing Agent Amanda Goldberg William Raveis-New York, LLC

  41 Valley Ln, Chappaqua, NY 10514
• 

  Est $3,375,662

  Not Listed For Sale

  3 Trails End, Chappaqua, NY 10514

  • 5 Beds
  • 5.5 Baths
  • 6,083 Sq Ft
  • Built 1994

  3 Trails End, Chappaqua, NY 10514

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC
• 

  

  /30

  $809,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  73 S Bedford Rd, Chappaqua, NY 10514

  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 Thomas S. Hennerty

  73 S Bedford Rd, Chappaqua, NY 10514
• 

  $1,376,000

  Sold Jul 23, 2026

  65 Douglas Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 1930

  Last Sold Summary

  • 10% Above List Price
  • $808/SF
  • 17 Days On Market

  Current Estimated Value $1,243,114

  Last Listing Agent Lynn Harmonay North Country Sothebys Int Rlt

  65 Douglas Rd, Chappaqua, NY 10514
• 

  Est $3,024,148

  Not Listed For Sale

  6 Trails End, Chappaqua, NY 10514

  • 5 Beds
  • 7 Baths
  • 7,624 Sq Ft
  • Built 1994

  6 Trails End, Chappaqua, NY 10514

  Last Sold Summary

  • 164 Days On Market

  Last Listing Agent Yaxing Zhang Houlihan Lawrence Inc.

Showing Results 81 - 120, Page 3 of 18