New Castle, NY Homes

Est $1,762,607

Not Listed For Sale

4 Circle Dr, Mount Kisco, NY 10549
- 3 Beds
- 1 Bath
- 1,307 Sq Ft
- Built 1957
4 Circle Dr, Mount Kisco, NY 10549

Last Sold Summary
- 48 Days On Market

/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
$1,975,000

Sold Aug 28, 2025

18 Brandon Dr, Mount Kisco, NY 10549
- 4 Beds
- 5.5 Baths
- 5,365 Sq Ft
- Built 1968
Last Sold Summary
- 1% Below List Price
- $368/SF
- 33 Days On Market
Current Estimated Value $2,148,453

Last Listing Agent Kile Boga-Ibric Houlihan Lawrence Inc.

18 Brandon Dr, Mount Kisco, NY 10549

Est $3,040,471

Not Listed For Sale

12 Petersville Rd, Mount Kisco, NY 10549
- 5 Beds
- 4.5 Baths
- 6,334 Sq Ft
- Built 2000
12 Petersville Rd, Mount Kisco, NY 10549

Last Sold Summary
- 6 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
$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 $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

/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
$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 $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

/28
$735,000

Pending
- 3 Beds
- 2 Baths
- 1,672 Sq Ft
20 Highview Rd, Ossining, NY 10562

Welcome to 20 Highview Road! Tucked away on a beautiful cul-de-sac in the desirable town of New Castle, this charming ranch offers a wonderful blend of comfort, functionality, and the opportunity to make it your own. Inside, you’ll find a bright, inviting layout featuring a spacious living room with a wood-burning fireplace, hardwood floors, and large windows that fill the space with natural

Yarden Ronen-van Heerden Compass Greater NY, LLC

20 Highview Rd, Ossining, NY 10562
$1,090,000

Sold Aug 08, 2025

83 Inningwood Rd, Millwood, NY 10546
- 4 Beds
- 2 Baths
- 1,874 Sq Ft
- Built 1955
Last Sold Summary
- 9% Below List Price
- $582/SF
- 34 Days On Market
Current Estimated Value $1,112,835

Last Listing Agent Amy Via Houlihan Lawrence Inc.

83 Inningwood Rd, Millwood, NY 10546

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

/26
$949,000
- 4 Beds
- 3 Baths
- 3,012 Sq Ft
6 Maria Ln, Ossining, NY 10562

Spacious and beautifully maintained raised ranch set on 2 level acres, offering the perfect combination of comfort, functionality, and flexible living space. This 4 bedroom, 3 full bath home lives like a 5 bedroom and features sun-filled interiors, hardwood floors, and charming brick fireplaces. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring rich

Mark Boyland Keller Williams Realty Partner

6 Maria Ln, Ossining, NY 10562
$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 $2,762,104

Not Listed For Sale

11 Hammond Ridge Rd, Mount Kisco, NY 10549
- 5 Beds
- 4.5 Baths
- 5,337 Sq Ft
- Built 2006
11 Hammond Ridge Rd, Mount Kisco, NY 10549

Last Sold Summary
- 10 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
$1,500,000

Sold Jul 24, 2025

134 Ruxton Rd, Mount Kisco, NY 10549
- 2 Beds
- 2.5 Baths
- 3,100 Sq Ft
- Built 1988
Last Sold Summary
- 3% Above List Price
- $484/SF
- 7 Days On Market
Current Estimated Value $1,540,340

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

134 Ruxton Rd, Mount Kisco, NY 10549

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

/2
$239,000

$36K PRICE DROP Pending
- Land
- 2.02 Acres
- $118,317 per Acre
181 Somerstown Rd, Millwood, NY 10546

2+ acres of Land in Chappaqua School District. Calling all Buyers that can't find what they're looking for in a single family home...Build Your own home just the way you like! Moments from Shopping, Highways and Schools. Over 150' of frontage. Needs Zoning, Planning, BOH approvals. Get started today. Additional Information: SoilType:Unknown,

Andrea Martone Houlihan Lawrence Inc.

181 Somerstown Rd, Millwood, NY 10546
$1,200,000

Sold Jul 31, 2025

16 Gregory Ln, Millwood, NY 10546
- 4 Beds
- 2.5 Baths
- 2,251 Sq Ft
- Built 1968
Last Sold Summary
- 10% Above List Price
- $533/SF
- 20 Days On Market
Current Estimated Value $1,222,991

Last Listing Agent Adriane Defeo Compass Greater NY, LLC

16 Gregory Ln, Millwood, NY 10546

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

/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
$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 $1,657,465

Not Listed For Sale

133 Westwood Dr, Mount Kisco, NY 10549
- 2 Beds
- 3 Baths
- 4,626 Sq Ft
- Built 1997
133 Westwood Dr, Mount Kisco, NY 10549

Last Sold Summary
- 107 Days On Market

/14
$299,000

Pending
- 4 Beds
- 2.5 Baths
- 2,374 Sq Ft
5 Maria Ln, Ossining, NY 10562

Opportunity knocks on this exceptionally private, 2+ acre parcel tucked away on a serene street ending with a cul-de-sac in the sought-after Town of New Castle. Whether you are looking to take on a complete top-to-bottom renovation or build the custom home of your dreams, this property offers the perfect foundation and acreage for your vision. While you'll feel worlds away in your own private

Anthony Lando Julia B Fee Sothebys Int. Rlty

5 Maria Ln, Ossining, NY 10562
$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 $7,521,348

Not Listed For Sale

123 Westwood Dr, Mount Kisco, NY 10549
- 8 Beds
- 14 Baths
- 9,952 Sq Ft
- Built 2007
123 Westwood Dr, Mount Kisco, NY 10549

Last Sold Summary
- 148 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
$1,679,000

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 $4,177,244

Not Listed For Sale

115 Westwood Dr, Mount Kisco, NY 10549
- 5 Beds
- 5.5 Baths
- 8,406 Sq Ft
- Built 2002
115 Westwood Dr, Mount Kisco, NY 10549

Last Sold Summary
- 27 Days On Market

/28
$1,100,000
- 4 Beds
- 3 Baths
- 2,606 Sq Ft
54 Allapartus Rd, Ossining, NY 10562

Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home offers a rare balance of privacy, space, convenience, and flexibility. Positioned on a corner lot and set far back from the road, the property provides a quiet and secluded feel while still being conveniently located approximately 15 minutes from downtown Chappaqua, the Chappaqua Train Station, shopping,

Derek Greene Greene Realty Group

54 Allapartus Rd, Ossining, NY 10562
$1,402,970

Sold Jun 23, 2025

8 Dewitt Dr Unit 66, Chappaqua, NY 10514
- 2 Beds
- 3.5 Baths
- 2,945 Sq Ft
- Built 2024
Last Sold Summary
- 5% Above List Price
- $476/SF
- 142 Days On Market
Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

8 Dewitt Dr Unit 66, Chappaqua, NY 10514

Est $1,438,135

Not Listed For Sale

39 Kitchel Rd, Mount Kisco, NY 10549
- 3 Beds
- 2.5 Baths
- 2,059 Sq Ft
- Built 1955
39 Kitchel Rd, Mount Kisco, NY 10549

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 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 $1,641,354

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

40 Smith St, Chappaqua, NY 10514

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

/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
$1,125,000

Sold Jul 21, 2025

16 Garey Dr, Chappaqua, NY 10514
- 4 Beds
- 2.5 Baths
- 1,888 Sq Ft
- Built 1958
Last Sold Summary
- 25% Above List Price
- $596/SF
- 18 Days On Market
Current Estimated Value $1,232,542

Last Listing Agent Sherry Wiggs Houlihan Lawrence Inc.

16 Garey Dr, Chappaqua, NY 10514

Est $2,240,885

Not Listed For Sale

19 Tall Timber, Mount Kisco, NY 10549
- 4 Beds
- 3.5 Baths
- 4,427 Sq Ft
- Built 1961
19 Tall Timber, Mount Kisco, NY 10549

Last Sold Summary
- 10 Days On Market

Showing Results 121 - 160, Page 4 of 18

New York Westchester County New Castle

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

New Castle, NY Homes

Real Estate & Homes