Homes in ZIP Code 10514

/35
$1,975,000
- 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

(914) 977-0609

111 Prospect Dr, Chappaqua, NY 10514
/25

$3,595 - $3,995 per month

Chappaqua Crossing Apartments

1 - 2 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
$1,600,000 Sold Feb 27, 2026

36 Pond Hill Rd, Chappaqua, NY 10514
- 3 Beds
- 3.5 Baths
- 2,866 Sq Ft
- Built 1952
Last Sold Summary
- 23% Above List Price
- $558/SF
- 11 Days On Market
Current Estimated Value $1,379,076

Last Listing Agent Danae Richards William Raveis-New York, LLC

36 Pond Hill Rd, Chappaqua, NY 10514

Est $1,296,667 Not Listed For Sale

27 Hardscrabble Hill Rd, Chappaqua, NY 10514
- 3 Beds
- 2.5 Baths
- 1,995 Sq Ft
- Built 1960
27 Hardscrabble Hill Rd, Chappaqua, NY 10514

Last Sold Summary
- $652/SF
- 11 Days On Market
- Last Sold Price $1,300,000
- Sep 04, 2024
Last Listing Agent Pamela Akin Douglas Elliman Real Estate

/39
$1,599,999 Pending
- 4 Beds
- 3 Baths
- 3,672 Sq Ft
734 King St, Chappaqua, NY 10514

Thoughtfully reimagined farmhouse with barn, this distinctive 4-bedroom, 3-bath home blends historic charm with striking modern design. Set on close to 2 private acres surrounded by mature trees, the property offers exceptional privacy and a peaceful natural setting. Inside, soaring ceilings, oversized windows, and multiple skylights flood the home with natural light. The open-concept living

Sari Shaw Compass Greater NY, LLC

734 King St, Chappaqua, NY 10514
/33
$11,500 per month
- 4 Beds
- 3.5 Baths
- 4,644 Sq Ft
- House for Rent
291 Roaring Brook Rd, Chappaqua, NY 10514

Welcome to the Jonathan Tompkins House, a true New Castle landmark dating back to 1750 where history and modern living intertwine. Ideally situated in the heart of Chappaqua and located within the award-winning Chappaqua School District, this fully furnished rental weaves centuries of New Castle’s past into its walls. Original hand-hewn beams and stained glass evoke timeless old-world charm,

Rachel Lacoste Houlihan Lawrence Inc.

291 Roaring Brook Rd, Chappaqua, NY 10514
$2,825,000 Sold Dec 15, 2025

70 Haights Cross Rd, Chappaqua, NY 10514
- 5 Beds
- 9 Baths
- 8,775 Sq Ft
- Built 2005
Last Sold Summary
- 10% Below List Price
- $322/SF
- 159 Days On Market
Current Estimated Value $2,949,884

Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

70 Haights Cross Rd, Chappaqua, NY 10514

Est $1,751,829 Not Listed For Sale

34 Hardscrabble Hill Rd, Chappaqua, NY 10514
- 4 Beds
- 3.5 Baths
- 3,700 Sq Ft
- Built 2014
34 Hardscrabble Hill Rd, Chappaqua, NY 10514

Last Sold Summary
- 17% Above List Price
- $405/SF
- 54 Days On Market
- Last Sold Price $1,499,000
- Aug 25, 2023
Last Listing Agent Mary Ann Tighe Houlihan Lawrence Inc.

/36
$1,599,000
- 3 Beds
- 2.5 Baths
- 3,121 Sq Ft
40 Kings Ct, Chappaqua, NY 10514

A truly exceptional offering, this picture-perfect 1930s Colonial blends timeless elegance with modern luxury. Set on beautifully landscaped property in a serene setting yet just a moment away from town. Impeccably maintained, tastefully expanded & renovated, the home showcases refined design, effortless flow, and enduring architectural charm.The main level is thoughtfully designed with a

Jennifer Harris Compass Greater NY, LLC

40 Kings Ct, Chappaqua, NY 10514
/10
$2,200 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. No pets allowed.

Mary Grant Houlihan Lawrence Inc.

85 Paulding Dr, Chappaqua, NY 10514
$2,475,000 Sold May 06, 2025

27 Neustadt Ln, Chappaqua, NY 10514
- 4 Beds
- 4 Baths
- 4,974 Sq Ft
- Built 1986
Last Sold Summary
- 29% Above List Price
- $498/SF
- 8 Days On Market
Current Estimated Value $2,462,862

Last Listing Agent Joanne Milch William Raveis-New York, LLC

27 Neustadt Ln, Chappaqua, NY 10514

Est $1,537,597 Not Listed For Sale

265 Mill River Rd, Chappaqua, NY 10514
- 4 Beds
- 4.5 Baths
- 4,811 Sq Ft
- Built 2010
265 Mill River Rd, Chappaqua, NY 10514

Last Sold Summary
- 30% Above List Price
- $246/SF
- 68 Days On Market
- Last Sold Price $1,185,000
- May 31, 2024
Last Listing Agent Sandra Cappucci Julia B Fee Sothebys Int. Rlty

/50
$2,475,000
- 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
$805,000 Sold Nov 21, 2025

149 King St Unit 4, Chappaqua, NY 10514
- 2 Beds
- 2.5 Baths
- 1,767 Sq Ft
- Built 1988
Last Sold Summary
- 6% Below List Price
- $456/SF
- 105 Days On Market
Last Listing Agent Nancy Jones Julia B Fee Sothebys Int. Rlty

149 King St Unit 4, Chappaqua, NY 10514

Est $839,224 Not Listed For Sale

70 Leroy Rd, Chappaqua, NY 10514
70 Leroy Rd, Chappaqua, NY 10514

Last Sold Summary
- 12% Above List Price
- 56 Days On Market
- Last Sold Price $749,000
- Aug 12, 2024
Last Listing Agent Jaimme Pudalov Houlihan Lawrence Inc.

/32
$1,949,000 Pending
- 4 Beds
- 5 Baths
- 5,767 Sq Ft
5 Morning View Ct, Chappaqua, NY 10514

A refined expression of modern Colonial living, this exceptional 4-bedroom, 5 full bath residence offers nearly 6,000 square feet of impeccably finished space, including a walk-out lower level, in one of Chappaqua’s most coveted settings. Built in 2012 and featuring natural gas and municipal sewer—an uncommon and highly desirable pairing—this home delivers a rare combination of quality, scale,

Sari Shaw Compass Greater NY, LLC

5 Morning View Ct, Chappaqua, NY 10514
$1,850,000 Sold Jul 15, 2025

22 Mountain Peak Rd, Chappaqua, NY 10514
- 5 Beds
- 4.5 Baths
- 4,419 Sq Ft
- Built 1972
Last Sold Summary
- 6% Above List Price
- $419/SF
- 17 Days On Market
Current Estimated Value $1,909,675

Last Listing Agent Usha Subramaniam Compass Greater NY, LLC

22 Mountain Peak Rd, Chappaqua, NY 10514

Not Listed For Sale

149 King St Unit 19, Chappaqua, NY 10514
- 2 Beds
- 2.5 Baths
- 1,664 Sq Ft
- Built 1988
149 King St Unit 19, Chappaqua, NY 10514

Last Sold Summary
- $526/SF
- 6 Days On Market
- Last Sold Price $875,000
- Apr 03, 2025
Last Listing Agent Alicja Bohmrich Houlihan Lawrence Inc.

/33
$2,300,000 Pending
- 3 Beds
- 3.5 Baths
- 3,960 Sq Ft
24 North Way, Chappaqua, NY 10514

AO-3/29-Move-in ready, light and bright 3 bedroom/ 3.5 bathroom home that lives like a 4 bedroom in the coveted Lawrence Farms South neighborhood with a private, flat backyard with a stone patio, heated gunite pool and a charming pergola. This inviting home with high ceilings throughout, offers a spacious living room with a fireplace, adjacent to a formal dining room, both with glass door access

Pamela Akin Douglas Elliman Real Estate

24 North Way, Chappaqua, NY 10514
$2,700,000 Sold May 09, 2025

3 Bradley Farms, Chappaqua, NY 10514
- 4 Beds
- 3.5 Baths
- 5,947 Sq Ft
- Built 1947
Last Sold Summary
- 2% Above List Price
- $454/SF
- 15 Days On Market
Current Estimated Value $2,779,273

Last Listing Agent Amrita Singh William Raveis-New York, LLC

3 Bradley Farms, Chappaqua, NY 10514

Not Listed For Sale

26 Dewitt Dr Unit 75, Chappaqua, NY 10514
- 3 Beds
- 2.5 Baths
- 3,335 Sq Ft
- Built 2024
26 Dewitt Dr Unit 75, Chappaqua, NY 10514

Last Sold Summary
- $489/SF
- 5 Days On Market
- Last Sold Price $1,631,110
- Feb 25, 2025
Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

/13
$2,000,000 Pending
- 4 Beds
- 2.5 Baths
- 4,500 Sq Ft
0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514

Custom design your dream home in a seamless process with ZappiCo, Westchester County's premier Real Estate Developer! This luxurious home is to-be-built in the highly desirable Chappaqua school district. With 4 spacious bedrooms and 2.5 beautifully appointed bathrooms, this home will be meticulously crafted with the finest materials and attention to detail. As you enter, you will be greeted by an

Rachel Lacoste Houlihan Lawrence Inc.

0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514
$810,000 Sold Feb 20, 2026

17 Ledgewood Commons, Millwood, NY 10546
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
- Built 1984
Last Sold Summary
- 2% Above List Price
- $368/SF
- 18 Days On Market
Current Estimated Value $717,775

Last Listing Agent Lindsay Silverman Compass Greater NY, LLC

17 Ledgewood Commons, Millwood, NY 10546

Not Listed For Sale

45 Lila Ln Unit 62, Chappaqua, NY 10514
- 2 Beds
- 3.5 Baths
- 3,101 Sq Ft
- Built 2023
45 Lila Ln Unit 62, Chappaqua, NY 10514

Last Sold Summary
- $569/SF
- 3 Days On Market
- Last Sold Price $1,763,056
- Jan 07, 2025
Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

/39
$1,549,000 Pending
- 4 Beds
- 2.5 Baths
- 3,956 Sq Ft
21 Kitchawan Dr, Chappaqua, NY 10514

Picture-perfect Colonial in one of Chappaqua’s most sought-after neighborhoods, blends timeless 1920s charm with modern comfort and style. Set on over an acre of exquisitely manicured, park-like grounds, this nearly 4,000 sq. ft. home offers 4 bedrooms, 2.5 baths, beautifully scaled rooms, and abundant natural light throughout.Anchoring the home, a magnificent living room welcomes you with a

Jennifer Harris Compass Greater NY, LLC

21 Kitchawan Dr, Chappaqua, NY 10514
$1,465,000 Sold Oct 01, 2025

33 High Way, Chappaqua, NY 10514
- 3 Beds
- 3.5 Baths
- 1,917 Sq Ft
- Built 1938
Last Sold Summary
- 22% Above List Price
- $764/SF
- 11 Days On Market
Current Estimated Value $1,481,971

Last Listing Agent Jennifer Harris Compass Greater NY, LLC

33 High Way, Chappaqua, NY 10514

Not Listed For Sale

41 Lila Ln Unit 60, Chappaqua, NY 10514
- 2 Beds
- 3.5 Baths
- 3,101 Sq Ft
- Built 2023
41 Lila Ln Unit 60, Chappaqua, NY 10514

Last Sold Summary
- $524/SF
- 117 Days On Market
- Last Sold Price $1,624,375
- Jan 21, 2025
Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

/36
$2,499,000 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

Natalia Wixom Compass Greater NY, LLC

34 Pebblebrook Way, Chappaqua, NY 10514
$1,550,000 Sold Jan 20, 2026

100 Old Farm Rd N, Chappaqua, NY 10514
- 3 Beds
- 2.5 Baths
- 2,971 Sq Ft
- Built 2010
Last Sold Summary
- 19% Above List Price
- $522/SF
- 13 Days On Market
Current Estimated Value $1,447,158

Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

100 Old Farm Rd N, Chappaqua, NY 10514

Not Listed For Sale

39 Lila Ln Unit 59, Chappaqua, NY 10514
- 2 Beds
- 4 Baths
- 3,101 Sq Ft
- Built 2023
39 Lila Ln Unit 59, Chappaqua, NY 10514

Last Sold Summary
- $524/SF
- 5 Days On Market
- Last Sold Price $1,626,348
- Nov 15, 2024
Last Listing Agent Debbe Yarosh Toll Brothers Real Estate Inc.

/43
$1,699,000 Pending
- 3 Beds
- 3.5 Baths
- 4,780 Sq Ft
790 Hardscrabble Rd, Chappaqua, NY 10514

A Timeless Colonial, Thoughtfully Reimagined for the Way We Live Today There is a certain feeling you get the moment you arrive, a sense of history, warmth, and quiet refinement. Set on a lush, level acre within the coveted Chappaqua School District, this stately Colonial has been beautifully renovated to honor its classic roots while embracing modern comfort and flexibility. The home’s striking

Kile Boga-Ibric Houlihan Lawrence Inc.

790 Hardscrabble Rd, Chappaqua, NY 10514
$1,589,000 Sold May 28, 2025

395 Bedford Rd, Chappaqua, NY 10514
- 5 Beds
- 3.5 Baths
- 3,041 Sq Ft
- Built 1955
Last Sold Summary
- $523/SF
- 26 Days On Market
Current Estimated Value $1,621,098

Last Listing Agent Catherine O'Connor Houlihan Lawrence Inc.

395 Bedford Rd, Chappaqua, NY 10514

Est $1,968,629 Not Listed For Sale

2 Point Place, Chappaqua, NY 10514
- 4 Beds
- 5 Baths
- 4,745 Sq Ft
- Built 2017
2 Point Place, Chappaqua, NY 10514

Last Sold Summary
- 11% Above List Price
- $374/SF
- 116 Days On Market
- Last Sold Price $1,775,000
- Dec 11, 2024
Last Listing Agent Hayes Hopple Julia B Fee Sothebys Int. Rlty

/36
$1,699,000 Pending
- 4 Beds
- 2.5 Baths
- 3,483 Sq Ft
12 Suzanne Ln, Chappaqua, NY 10514

Perfectly positioned at the end of a quiet cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath Colonial offers the ideal blend of space, comfort, and effortless living—set on expansive, level property designed for both everyday enjoyment and memorable entertaining. A gracious foyer welcomes you, seamlessly opening to the living and dining rooms and creating a natural flow for gatherings.

Jennifer Harris Compass Greater NY, LLC

12 Suzanne Ln, Chappaqua, NY 10514
$1,659,995 Sold Sep 10, 2025

19 Wallace Way Unit 25, Chappaqua, NY 10514
- 2 Beds
- 4 Baths
- 3,432 Sq Ft
- Built 2022
Last Sold Summary
- 4% Below List Price
- $484/SF
- 91 Days On Market
Current Estimated Value $1,727,711

Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

19 Wallace Way Unit 25, Chappaqua, NY 10514

Est $1,742,677 Not Listed For Sale

20 Lawrence Frm Crswy, Chappaqua, NY 10514
- 4 Beds
- 2.5 Baths
- 4,085 Sq Ft
- Built 1978
20 Lawrence Frm Crswy, Chappaqua, NY 10514

Last Sold Summary
- 5% Above List Price
- $407/SF
- 9 Days On Market
- Last Sold Price $1,662,500
- Mar 08, 2025
Last Listing Agent Cindy Glynn Compass Greater NY, LLC

/33
$1,599,000
- 4 Beds
- 2.5 Baths
- 3,496 Sq Ft
34 Turner Dr, Chappaqua, NY 10514

Welcome to 34 Turner Drive South -- an expanded and gracious 4-bedroom, 2-1/2 Bath, Farmhouse Colonial nestled at the end of a private drive. This special home is set on over an acre of flat, private property, surrounded by towering trees and tranquil woods. The interior features 3 fireplaces, custom millwork, hardwood floors and classic architectural details. The main level has a gracious Living

Victoria Miller Compass Greater NY, LLC

34 Turner Dr, Chappaqua, NY 10514
$3,400,000 Sold Sep 09, 2025

5 Briarcliff Rd, Chappaqua, NY 10514
- 4 Beds
- 7 Baths
- 7,305 Sq Ft
- Built 2007
Last Sold Summary
- 8% Below List Price
- $465/SF
- 65 Days On Market
Current Estimated Value $3,449,113

Last Listing Agent Sari Shaw Compass Greater NY, LLC

5 Briarcliff Rd, Chappaqua, NY 10514

Not Listed For Sale

35 Lila Ln Unit 57, Chappaqua, NY 10514
- 2 Beds
- 3.5 Baths
- 3,386 Sq Ft
- Built 2023
35 Lila Ln Unit 57, Chappaqua, NY 10514

Last Sold Summary
- $588/SF
- 115 Days On Market
- Last Sold Price $1,990,428
- Oct 25, 2024
Last Listing Agent Debbe Yarosh Toll Brothers Real Estate Inc.

/38
$1,249,000 Coming Soon
- 4 Beds
- 2.5 Baths
- 2,478 Sq Ft
14 Aldridge Rd, Chappaqua, NY 10514

Classic 1920 Colonial brimming with vintage charm and modern updates, ideally located on a desirable cul-de-sac just a short walk to town. This beautifully maintained 4/5-bedroom home features 2 renovated full baths plus a new powder room, a sparkling white renovated kitchen with floor to ceiling cabinetry, stainless steel appliances-Sub Zero, Miele, & Viking and a generous eat-in area with door

Sena Baron William Raveis-New York, LLC

14 Aldridge Rd, Chappaqua, NY 10514

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New York Westchester County Chappaqua 10514

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Homes in ZIP Code 10514

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