Homes in ZIP Code 10514

/39
$2,195,000

Pending
- 6 Beds
- 5.5 Baths
- 6,563 Sq Ft
22 Random Farms Cir, Chappaqua, NY 10514

Set on a picturesque property in sought-after Random Farms, this stunning 6-bedroom residence offers dramatic views, soaring ceilings, and exceptional living spaces designed for both everyday comfort and elegant entertaining. A breathtaking double-height entry welcomes you into sun-drenched interiors featuring walls of windows, rich hardwood floors, and seamless open-concept flow

Sari Shaw Compass Greater NY, LLC

22 Random Farms Cir, Chappaqua, NY 10514
$1,658,000

Sold Aug 25, 2025

4 Carriage Ln Unit 82, Chappaqua, NY 10514
- 2 Beds
- 3.5 Baths
- 3,614 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $459/SF
- 47 Days On Market
Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

4 Carriage Ln Unit 82, Chappaqua, NY 10514

Est $1,869,953

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

/7
$1,658,995

Pending
- 2 Beds
- 3.5 Baths
- 3,353 Sq Ft
11 Wallace Way Unit 18, Chappaqua, NY 10514

To be Built! Spring 2025 move-in. 3485 square feet ! Still time to personalize interior finishes at our luxury Design Studio. Final building for sale at Chappaqua Crossing! A roaring fireplace will warm the entire home. A private rooftop terrace with included outdoor gas fireplace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this

Andrea Martone Houlihan Lawrence Inc.

11 Wallace Way Unit 18, Chappaqua, NY 10514
$752,000

Sold Aug 19, 2025

375 Quaker Rd, Chappaqua, NY 10514
- 3 Beds
- 2.5 Baths
- 2,084 Sq Ft
- Built 1910
Last Sold Summary
- 16% Above List Price
- $361/SF
- 17 Days On Market
Current Estimated Value $913,324

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

375 Quaker Rd, Chappaqua, NY 10514

Est $2,011,758

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

/41
$1,600,000

Pending
- 4 Beds
- 3.5 Baths
- 3,138 Sq Ft
14 Crossways, Chappaqua, NY 10514

Most “walk-to-town” homes ask you to compromise on space, privacy, or both. At 14 Crossways, you get all three. Set less than a mile from the Chappaqua station, it combines true walkability with more than 3,100 square feet of well-organized living space on a private, level half-acre. Carefully maintained and thoughtfully improved, it is also a house designed for entertaining. At its center, the

Jonathan Cape Julia B Fee Sothebys Int. Rlty

14 Crossways, Chappaqua, NY 10514
$2,960,000

Sold Dec 26, 2025

93 Haights Cross Rd, Chappaqua, NY 10514
- 4 Beds
- 4.5 Baths
- 6,542 Sq Ft
- Built 1979
Last Sold Summary
- 15% Below List Price
- $452/SF
- 102 Days On Market
Current Estimated Value $3,077,164

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

93 Haights Cross Rd, Chappaqua, NY 10514

Est $1,669,211

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

/49
$2,475,000

$124K PRICE DROP Pending
- 4 Beds
- 4.5 Baths
- 6,640 Sq Ft
17 Byram Meadows Rd, Chappaqua, NY 10514

Beautifully appointed and meticulously maintained 4 bedroom, 4 1/2 bath Colonial set on a level acre at the end of a quiet cul-de-sac in prestigious Inglenook Farm in the coveted Byram Hills Schools. A grand and light-filled two-story entry welcomes you into this refined open layout home featuring 9-foot ceilings on 1st and 2nd levels, oak flooring, and custom moldings and trim throughout. Formal

Cindy Glynn Compass Greater NY, LLC

17 Byram Meadows Rd, Chappaqua, NY 10514
$525,000

Sold Oct 16, 2025

380 Whippoorwill Rd, Chappaqua, NY 10514
- 3 Beds
- 2 Baths
- 880 Sq Ft
- Built 1927
Last Sold Summary
- 16% Below List Price
- $597/SF
- 61 Days On Market
Current Estimated Value $730,660

Last Listing Agent Sari Shaw Compass Greater NY, LLC

380 Whippoorwill Rd, Chappaqua, NY 10514

Est $2,470,629

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

/17
$3,350,000

New Construction Pending
- 4 Beds
- 7 Baths
- 5,712 Sq Ft
201 Bedford Rd, Chappaqua, NY 10514

Exciting all new construction by highly regarded local builder, Tavo Development, along with noted architect Teo Siguenza, aiming for a Fall 2026 completion. This refined, 5,712 sq ft Colonial blends classic architecture with sophisticated modern living. The light-filled main level, with 10’ ceilings, offers a seamless open floorplan featuring a chef’s kitchen with island and service pantry,

Brian Milton Compass Greater NY, LLC

201 Bedford 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 $1,084,340

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

326 Millwood Rd, Chappaqua, NY 10514

Est $3,219,580

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

/6
$639,000
- Land
- 7,405 Sq Ft
- $3,758,824 per Acre
65 S Bedford Rd, Chappaqua, NY 10514

A rare opportunity to build mixed use consisting of commercial/professional and multi-family with huge income potential.The 1st floor as commercial and the 2nd and 3rd floors residential apartments.An architect has drawn 4 concept plans ranging from commercial space and lobby with (4) 2-bedroom apartments to commercial space and lobby with (6) 1-bedroom apartments.One example:1st

Theodore Weinstein REO Edge LLC

65 S Bedford Rd, 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 $2,699,597

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

8 Turtleback Way, Chappaqua, NY 10514

Est $2,296,437

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

/47
$3,389,000
- 4 Beds
- 6.5 Baths
- 5,563 Sq Ft
40 Algonquin Dr, Chappaqua, NY 10514

Timeless elegance meets relaxed country chic at this extraordinary Chappaqua retreat. Ideally situated on one of Chappaqua's most coveted streets, this remarkable residence was originally built in 1910 and completely renovated and reimagined in 200l and then again in 2009 for modern living. Privately set amid beautifully landscaped grounds, 40 Algonquin blends classic country manor-style

Kathryn Weinberger Compass Greater NY, LLC

40 Algonquin Dr, 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 $1,310,363

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

71 Commodore Rd, Chappaqua, NY 10514

Est $1,571,266

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

/29
$1,499,000

Pending
- 4 Beds
- 3 Baths
- 3,002 Sq Ft
95 Old Lyme Rd, Chappaqua, NY 10514

Attractive contemporary home ideally located near town, offering over 3,000 square feet of light-filled living space with soaring ceilings and a wonderful open flow for today’s lifestyle. This 4-bedroom home features a spacious cook’s kitchen, three fireplaces, and generously scaled rooms designed for comfortable everyday living and easy entertaining. A flexible first-floor room plus full bath

Amy Singer Houlihan Lawrence Inc.

95 Old Lyme 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 $1,933,333

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

2 Whippoorwill Close, Chappaqua, NY 10514

Est $1,707,696

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

/49
$2,350,000

Pending
- 4 Beds
- 5 Baths
- 4,385 Sq Ft
790 King St, Chappaqua, NY 10514

A Rare Opportunity Where History Meets Modern Living.Built in 1750 and thoughtfully renovated in 2005. White clapboard, black shutters, cedar shake roof, and copper gutters set a timeless exterior, framed by professionally designed grounds.A wide entry hall opens to living and dining rooms bookended by floor-to-ceiling stone fireplaces. Hardwood floors and detailed millwork mark the

Harriet Libov Houlihan Lawrence Inc.

790 King St, Chappaqua, NY 10514
$1,800,000

Sold Jul 24, 2025

10 Tall Timber, Mount Kisco, NY 10549
- 4 Beds
- 2.5 Baths
- 3,354 Sq Ft
- Built 1960
Last Sold Summary
- 20% Above List Price
- $537/SF
- 10 Days On Market
Current Estimated Value $1,921,749

Last Listing Agent Lindsay Matthews Houlihan Lawrence Inc.

10 Tall Timber, Mount Kisco, NY 10549

Est $2,084,717

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

/36
$1,299,000

Pending
- 3 Beds
- 3 Baths
- 2,444 Sq Ft
816 Hardscrabble Rd, Chappaqua, NY 10514

Just north of NYC, this move-in ready CHAPPAQUA home delivers effortless, elevated living—done RIGHT.3 min drive to Metro North station - 48 min ride to Grand Central Station * Set behind a long private driveway with an attached 2-car garage and expansive front yard, the property captures stunning sunset views, with golden hour pouring in the best way. Inside captures a calm, grounded palette

Bianca Siani eXp Realty

816 Hardscrabble Rd, Chappaqua, NY 10514
$950,000

Sold Jul 17, 2025

514 Saw Mill River Rd, Millwood, NY 10546
- 3 Beds
- 3 Baths
- 2,296 Sq Ft
- Built 1976
Last Sold Summary
- 7% Above List Price
- $414/SF
- 6 Days On Market
Current Estimated Value $1,016,226

Last Listing Agent Hiralben Trivedi Compass Greater NY, LLC

514 Saw Mill River Rd, Millwood, NY 10546

Est $2,780,990

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

/27
$899,000

Open Sat 12PM - 3PM
- 3 Beds
- 2.5 Baths
- 1,586 Sq Ft
2 Timberland Pass, Chappaqua, NY 10514

Welcome to Apple Hill Farm, sitting on highly desirable, 37+ Wooded Acres. Where calm meets comfort. This corner Townhome, located in a cul-de-sac for added privacy, features a manicured lawn and a carefully curated garden. Experience modern elegance in this home, with high ceilings, lots of Windows and Skylights that bring abundant natural daylight and sunlight indoors. It has 3 Bedrooms and 2.5

Nana Aboagye Dorothy Jensen Realty, Inc.

2 Timberland Pass, 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 $1,739,959

Last Listing Agent Sari Shaw Compass Greater NY, LLC

6 Whippoorwill Lake Rd, Chappaqua, NY 10514

Est $1,537,264

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

/41
$2,750,000

Pending
- 6 Beds
- 3.5 Baths
- 6,532 Sq Ft
276 Quaker Rd, Chappaqua, NY 10514

A truly rare Chappaqua mini-estate with pool and tennis, offering resort-style living just a short walk from the town and train. Privately perched atop a hill and approached by a sweeping stone-lined driveway, this property delivers an exceptional blend of privacy, presence, and convenience—moments from shops, dining, and Metro-North. The expansive grounds are designed for all-season enjoyment,

Sari Shaw Compass Greater NY, LLC

276 Quaker Rd, Chappaqua, NY 10514
$1,775,000

Sold Jul 17, 2025

3 Sunset Dr, Chappaqua, NY 10514
- 4 Beds
- 3.5 Baths
- 3,587 Sq Ft
- Built 1969
Last Sold Summary
- 11% Above List Price
- $495/SF
- 7 Days On Market
Current Estimated Value $1,894,662

Last Listing Agent Debra Goldenberg Compass Greater NY, LLC

3 Sunset Dr, Chappaqua, NY 10514

Est $2,594,096

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

/42
$1,399,000

Pending
- 4 Beds
- 2.5 Baths
- 2,443 Sq Ft
6 Killington St, Chappaqua, NY 10514

Dreamy modern ranch nestled on a private landscaped acre on a cul-de-sac in sought-after Whippoorwill. A flagstone walkway leads to a covered entry. The contemporary-styled front door with cross-reed glass panels and sidelight sets a refined first impression. Designed for effortless indoor/outdoor living, the rear-facing living room anchors the home with a wood-burning fireplace and two sets of

Stacy Levey William Raveis-New York, LLC

6 Killington St, 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 $2,950,859

Not Listed For Sale

6 Hemlock Hollow, Chappaqua, NY 10514
- 4 Beds
- 4.5 Baths
- 6,422 Sq Ft
- Built 1998
6 Hemlock Hollow, Chappaqua, NY 10514

Last Sold Summary
- 21 Days On Market

/47
$1,100,000

Pending
- 4 Beds
- 3.5 Baths
- 2,429 Sq Ft
8 Old Roaring Brook Rd, Mount Kisco, NY 10549

Set on a bucolic country road, this unique early-1900s home seamlessly blends old world charm with modern-day amenities. Bright and happy throughout, the home offers a wonderful flow ideal for both everyday living and entertaining. A sun-filled dining room with walls of glass brings the outdoors in, while the inviting living spaces create warmth and comfort. The first floor also features a living

Stacey Sporn William Raveis Real Estate

8 Old Roaring Brook Rd, Mount Kisco, NY 10549

Showing Results 81 - 120, Page 3 of 18

New York Westchester County Chappaqua 10514

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Homes in ZIP Code 10514

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