Homes in ZIP Code 10514

/44
$4,500,000
- 5 Beds
- 7 Baths
- 7,608 Sq Ft
150 Old Farm Rd N, Chappaqua, NY 10514

1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original

Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

150 Old Farm Rd N, 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 $2,115,131

Not Listed For Sale

9 Meadow Hill Place, Armonk, NY 10504
- 5 Beds
- 4 Baths
- 4,664 Sq Ft
- Built 1975
9 Meadow Hill Place, Armonk, NY 10504

Last Sold Summary
- 37 Days On Market
Last Listing Agent Michael Neeley William Raveis-New York LLC

/36
$2,499,000

$101K PRICE DROP Pending
- 5 Beds
- 4.5 Baths
- 4,482 Sq Ft
34 Pebblebrook Way, Chappaqua, NY 10514

The only triple mint move-in condition house in Chappaqua schools. Nestled within 1.65 acres in the sought-after Hardscrabble Lake development and Chappaqua school district, this rare find modern Center Hall Colonial home epitomizes luxury living. If you are searching for a masterpiece beautifully finished home that is turnkey inside and out, this is your home. This meticulously thought-out home

Natalia Wixom Compass Greater NY, LLC

34 Pebblebrook Way, 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 $3,625,174

Not Listed For Sale

29 Carolyn Place, Armonk, NY 10504
- 5 Beds
- 4.5 Baths
- 7,448 Sq Ft
- Built 1972
29 Carolyn Place, Armonk, NY 10504

Last Sold Summary
- 46 Days On Market
Last Listing Agent Brian Milton 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 $2,859,881

Not Listed For Sale

16 Kittle Rd, Chappaqua, NY 10514
- 5 Beds
- 5.5 Baths
- 4,249 Sq Ft
- Built 1936
16 Kittle Rd, Chappaqua, NY 10514

Last Sold Summary
- 13 Days On Market
Last Listing Agent Heather Bouza Compass Greater NY, LLC

/44
$1,399,000
- 3 Beds
- 3 Baths
- 2,821 Sq Ft
10 Deborah Ln, Chappaqua, NY 10514

SoHo in Chappaqua! Chappaqua schools! Dramatic, Airy and Light-filled 3 Bedroom Contemporary in immaculate condition located in sought-after neighborhood and Cul-De-Sac. Set on almost an acre of private property with rocking-chair front porch. Elegant living room features a soaring cathedral ceiling, wall of built-in bookshelves and wall of windows opening to dining area with access to deck.

Alicja Bohmrich Houlihan Lawrence Inc.

10 Deborah Ln, 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 $1,953,892

Not Listed For Sale

55 Cowdin Cir, Chappaqua, NY 10514
- 4 Beds
- 3.5 Baths
- 4,045 Sq Ft
- Built 1952
55 Cowdin Cir, Chappaqua, NY 10514

Last Sold Summary
- 13 Days On Market
Last Listing Agent Eric Stein RE/MAX Distinguished Hms.&Prop

/5
$679,000
- 4 Beds
- 2 Baths
- 2,464 Sq Ft
10 Paula Place, Chappaqua, NY 10514

A unique opportunity to create your dream home on 3+ wooded acres in the highly sought-after Chappaqua School District. Tucked away at the end of a cul-de-sac, this exceptional property offers privacy, natural beauty, and tremendous potential for a builder, investor or end user.The existing home is in need of removal, presenting an opportunity to bring your vision to life and build a new

Victoria Miller Compass Greater NY, LLC

10 Paula Place, 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 $2,008,269

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
$2,299,000

Open Sat 1PM - 3PM Coming Soon
- 5 Beds
- 4.5 Baths
- 4,661 Sq Ft
20 Hitching Post Ln, Chappaqua, NY 10514

Welcome to 20 Hitching Post Lane in Chappaqua, New York. This five-bedroom, 4.1 bath Colonial is set on over 2 bucolic acres on a beautiful tree-lined street. An impressive oak floored entry foyer with cherry inlay opens to a spacious formal living room with crown moldings and new windows (2023), warmed by a wood burning fireplace with decorative mantle. The adjacent family room has a second wood

John Buckley William Raveis-New York LLC

20 Hitching Post Ln, 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 $1,751,550

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.

/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 $2,733,935

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

/31
$1,725,000
- 4 Beds
- 3.5 Baths
- 3,581 Sq Ft
53 W Orchard Rd, 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 in a quiet neighborhood, this stunning property offers privacy, space & luxury living at its finest. In addition, easy access to the North County Trail for any outdoor activities of your choice. Step inside & you'll

Lori Meringolo Houlihan Lawrence Inc.

53 W Orchard 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 $3,360,018

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

/27
$1,590,000
- 3 Beds
- 3.5 Baths
- 2,690 Sq Ft
131 Douglas Rd, Chappaqua, NY 10514

Tastefully 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

Toni DiMichelo Houlihan Lawrence Inc.

131 Douglas 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 $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

/49
$1,800,000
- 4 Beds
- 3.5 Baths
- 2,913 Sq Ft
406 Bedford Rd, Chappaqua, NY 10514

Welcome to this beautifully maintained almost 3000 sq ft 4 bedroom 4 bath Colonial set on a private, sun-filled one acre property framed by mature trees, a classic stone wall , and meticulously maintained landscaping and plantings.Elegance and craftsmanship are evident throughout with beautiful hardwood floors, generously sized bedrooms and a primary suite with private en-suite bath. At

Donna Powers-Amori Howard Hanna Rand Realty

406 Bedford Rd, Chappaqua, NY 10514
$1,745,000

Sold Aug 03, 2026

2 Dewitt Dr, Chappaqua, NY 10514
- 2 Beds
- 3.5 Baths
- 3,574 Sq Ft
- Built 2025
Last Sold Summary
- 8% Below List Price
- $488/SF
- 73 Days On Market
Last Listing Agent Joann Galluccio William Raveis-New York LLC

2 Dewitt Dr, 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

/30
$809,000

$20K PRICE DROP Pending
- 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
$1,725,000

Sold Oct 31, 2025

9 Point Place, Chappaqua, NY 10514
- 4 Beds
- 3.5 Baths
- 4,100 Sq Ft
- Built 2019
Last Sold Summary
- 11% Above List Price
- $421/SF
- 24 Days On Market
Current Estimated Value $1,849,020

Last Listing Agent Mark Boyland Keller Williams Realty Partner

9 Point Place, 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.

/30
$749,000
- 3 Beds
- 1.5 Baths
- 1,414 Sq Ft
27 Mill River Rd, Chappaqua, NY 10514

You’ll be hard-pressed to find a turn-key home like this—especially at this price—in the Chappaqua School District, let alone Westchester County! Welcome to this charming 1850s Colonial, ideally situated in the heart of Chappaqua, just 0.3 miles on foot via a convenient sidewalk to Metro-North and close to all that the village has to offer. With an easy walk to the train and convenient access by

Johanna Kline Houlihan Lawrence Inc.

27 Mill River Rd, Chappaqua, NY 10514
$2,250,000

Sold Aug 11, 2026

22 Random Farms Cir, Chappaqua, NY 10514
- 6 Beds
- 5.5 Baths
- 6,563 Sq Ft
- Built 1993
Last Sold Summary
- 3% Above List Price
- $343/SF
- 10 Days On Market
Current Estimated Value $2,206,714

Last Listing Agent Sari Shaw Compass Greater NY, LLC

22 Random Farms Cir, Chappaqua, NY 10514

Est $2,129,303

Not Listed For Sale

14 Tall Timber, Mount Kisco, NY 10549
- 4 Beds
- 3.5 Baths
- 4,312 Sq Ft
- Built 1962
14 Tall Timber, Mount Kisco, NY 10549

Last Sold Summary
- 11 Days On Market
Last Listing Agent Danae Richards William Raveis-New York, LLC

/31
$849,999

$49K PRICE DROP
- 4 Beds
- 2 Baths
- 2,100 Sq Ft
249 Mill River Rd, Chappaqua, NY 10514

NOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed

Harry Donofrio Town and Village Real Estate

249 Mill River Rd, Chappaqua, NY 10514
$1,391,022

Sold Oct 23, 2025

6 Algonquin Dr, Chappaqua, NY 10514
- 4 Beds
- 3.5 Baths
- 3,776 Sq Ft
- Built 1952
Last Sold Summary
- 16% Above List Price
- $368/SF
- 30 Days On Market
Current Estimated Value $1,513,457

Last Listing Agent Lindsay Rothman Compass Greater NY LLC

6 Algonquin Dr, 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

/43
$1,575,000

$75K PRICE DROP Pending
- 4 Beds
- 4 Baths
- 2,715 Sq Ft
50 Ludlow Dr, Chappaqua, NY 10514

Set on a sought-after cul-de-sac lined with charming classic homes, this 1938 Colonial masterfully blends period charm with today’s lifestyle needs. Set on a lovely private acre with flat lawns surrounded by towering trees yet nestled in a neighborhood setting, this 2,715 square foot center hall Colonial home offers 4 bedrooms, 2 full and 2 half baths. The heart of the home is the family room

Sena Baron William Raveis-New York, LLC

50 Ludlow Dr, Chappaqua, NY 10514

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