New Castle, NY Homes

/39
$1,450,000 Pending
- 4 Beds
- 2.5 Baths
- 2,658 Sq Ft
40 Smith St, Chappaqua, NY 10514

Step into a story of timeless elegance in this enchanting 1920s village colonial, where the romantic allure of yesteryear meets the effortless luxury of modern living. Located in the heart of the village, this home offers a lifestyle of rare convenience—just a gentle stroll to vibrant shops, local cafes, and the morning train.Inside, the home whispers of its storied past through beautifully

Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

40 Smith St, Chappaqua, NY 10514
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/50
$9,999 per month
- 4 Beds
- 3.5 Baths
- 4,340 Sq Ft
- House for Rent
82 Shingle House Rd, Millwood, NY 10546

Welcome to 82 Shingle House Road, a stunning 6.9-acre mini-estate tucked away on a quiet, tree-lined street in Millwood. This exceptional property offers an ideal blend of space, comfort, and natural beauty. The main residence features 4 bedrooms and 3.5 bathrooms, complemented by generous living areas and timeless charm. A fully renovated guest cottage sits above a 3-car garage, perfect for

Frank Norwood DC & SF Inc

82 Shingle House Rd, Millwood, NY 10546
$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 $1,485,959

Last Listing Agent Jennifer Harris Compass Greater NY, LLC

33 High Way, Chappaqua, NY 10514

Not Listed For Sale

1176 Hardscrabble Rd, Chappaqua, NY 10514
- 4 Beds
- 3 Baths
- 3,537 Sq Ft
- Built 1956
1176 Hardscrabble Rd, Chappaqua, NY 10514

Last Sold Summary
- $560/SF
- 44 Days On Market
Last Sold Price $1,980,000

Last Listing Agent Amy Via Houlihan Lawrence Inc.

/13
$2,000,000
- 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
/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
$765,000 Sold Apr 07, 2025

12 Pines Ln, Chappaqua, NY 10514
- 3 Beds
- 2 Baths
- 2,249 Sq Ft
- Built 1948
Last Sold Summary
- 4% Below List Price
- $340/SF
- 93 Days On Market
Current Estimated Value $858,412

Last Listing Agent David Turner Compass Greater NY, LLC

12 Pines Ln, Chappaqua, NY 10514

Not Listed For Sale

16 Maria Ln, Ossining, NY 10562
- 4 Beds
- 3.5 Baths
- 3,427 Sq Ft
- Built 1887
16 Maria Ln, Ossining, NY 10562

Last Sold Summary
- $455/SF
- 33 Days On Market
Last Sold Price $1,560,222

Last Listing Agent Mark Seiden Mark Seiden Real Estate Team

/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
/26
$8,000 per month
- 4 Beds
- 3 Baths
- 3,141 Sq Ft
- House for Rent
49 Commodore Rd, Chappaqua, NY 10514

Picture perfect center hall colonial. Ideal executive rental, walk to town and train. Living room with fireplace, dining room with sliders to large deck, and modern eat-in kitchen. Bedroom and full bath on first level, perfect for au-pair or guest suite. Primary bedroom with en-suite bath, featuring double sink vanity, jacuzzi tub and stand alone shower. Two more hall bedrooms, well-appointed

Gail Silverstein ERA Insite Realty Services

49 Commodore Rd, Chappaqua, NY 10514
$2,300,000 Sold Nov 20, 2025

24 North Way, Chappaqua, NY 10514
- 3 Beds
- 3.5 Baths
- 3,960 Sq Ft
- Built 1986
Last Sold Summary
- 24% Above List Price
- $581/SF
- 7 Days On Market
Current Estimated Value $2,220,099

Last Listing Agent Pamela Akin Douglas Elliman Real Estate

24 North Way, Chappaqua, NY 10514

Not Listed For Sale

9 Barnes Rd, Ossining, NY 10562
- 4 Beds
- 4.5 Baths
- 4,583 Sq Ft
- Built 1797
9 Barnes Rd, Ossining, NY 10562

Last Sold Summary
- $305/SF
- 37 Days On Market
Last Sold Price $1,399,000

Last Listing Agent Sena Baron William Raveis-New York, LLC

/42
$1,399,000 Open Sun 12PM - 2PM
- 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
$1,589,000 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 $1,617,966

Last Listing Agent Catherine O'Connor Houlihan Lawrence Inc.

395 Bedford Rd, Chappaqua, NY 10514

Not Listed For Sale

504 Millwood Rd, Mount Kisco, NY 10549
- 4 Beds
- 2.5 Baths
- 3,182 Sq Ft
- Built 1910
504 Millwood Rd, Mount Kisco, NY 10549

Last Sold Summary
- $270/SF
- 116 Days On Market
Last Sold Price $860,000

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

/34
$1,450,000 Pending
- 5 Beds
- 3 Baths
- 2,885 Sq Ft
18 Hayrake Ln, Chappaqua, NY 10514

Nestled on one of Chappaqua’s most desirable cul-de-sac neighborhoods, this move-right-in, Bradley-built 5-bedroom Cape is privately set and offers the perfect blend of refined living and everyday comfort. Sun-filled interiors exude warmth and character, with graciously sized rooms and a highly versatile layout designed to grow with your family. The main level features a spacious living room with

Danae Richards William Raveis-New York, LLC

18 Hayrake 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 $1,702,037

Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

19 Wallace Way Unit 25, Chappaqua, NY 10514

Not Listed For Sale

51 Pinesbridge Rd, Ossining, NY 10562
- 8 Beds
- 8 Baths
- 5,337 Sq Ft
- Built 1935
51 Pinesbridge Rd, Ossining, NY 10562

Last Sold Summary
- $178/SF
- 10 Days On Market
Last Sold Price $950,000

Last Listing Agent Angela Kessel Houlihan Lawrence Inc.

/40
$1,336,000 Pending
- 3 Beds
- 2.5 Baths
- 2,417 Sq Ft
148 Devoe Rd, Chappaqua, NY 10514

Classic Devoe Road colonial! A covered front portico welcomes you to this timeless traditional 3-bedroom, 2.5-bath colonial-style home. The spacious living room, anchored by a wood burning fireplace and lined with custom bookshelves enjoys radiant sunshine from the oversized true divided light picture window overlooking the front of the residence. The living room adjoins the formal dining room,

Stacy Levey William Raveis-New York, LLC

148 Devoe Rd, 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 $3,443,758

Last Listing Agent Sari Shaw Compass Greater NY, LLC

5 Briarcliff Rd, Chappaqua, NY 10514

Not Listed For Sale

130 Pinesbridge Rd, Ossining, NY 10562
- 4 Beds
- 3 Baths
- 2,644 Sq Ft
- Built 1946
130 Pinesbridge Rd, Ossining, NY 10562

Last Sold Summary
- $170/SF
- 168 Days On Market
Last Sold Price $450,000

Last Listing Agent Natalia Wixom Compass Greater NY, LLC

/36
$2,175,000 Pending
- 4 Beds
- 4.5 Baths
- 5,541 Sq Ft
17 Hammond Ridge Rd, Mount Kisco, NY 10549

Set within the coveted Hammond Ridge neighborhood of Bedford Corners, this impressive 4-bedroom, 5-bath Colonial blends timeless elegance with today’s modern comforts. A long, welcoming driveway leads to a home with a private and serene setting, sun-filled interiors and expansive picture windows create a bright, airy ambiance throughout. The home offers a versatile layout ideal for both

Susan Slotnick William Raveis Real Estate

17 Hammond Ridge Rd, Mount Kisco, NY 10549
$956,000 Sold Jun 25, 2025

21 Vails Ln, Ossining, NY 10562
- 5 Beds
- 3.5 Baths
- 2,684 Sq Ft
- Built 1968
Last Sold Summary
- 3% Above List Price
- $356/SF
- 17 Days On Market
Current Estimated Value $969,572

Last Listing Agent Sherry Wiggs Houlihan Lawrence Inc.

21 Vails Ln, Ossining, NY 10562

Not Listed For Sale

49 Spring Valley Rd, Ossining, NY 10562
- 5 Beds
- 3 Baths
- 2,754 Sq Ft
- Built 1855
49 Spring Valley Rd, Ossining, NY 10562

Last Sold Summary
- $283/SF
- 75 Days On Market
Last Sold Price $780,000

Last Listing Agent Maria Vele Keller Williams Realty Partner

/38
$1,150,000 Pending
- 3 Beds
- 3 Baths
- 2,364 Sq Ft
200 S Bedford Rd, Chappaqua, NY 10514

Completely updated and remodeled residence in the heart of Chappaqua, offering a highly versatile layout ideal for in-law suite, professional office, and/or apartment use. The home features two bedrooms plus an office in the main residence, plus a private, 1-bedroom legal accessory apartment currently generating $2,500 per month in rental income. The property also offers the flexibility to live

Annette Cicinelli Keller Williams Realty Partner

200 S Bedford Rd, Chappaqua, NY 10514
$820,000 Sold Aug 20, 2025

149 King St Unit 15, Chappaqua, NY 10514
- 2 Beds
- 2.5 Baths
- 1,925 Sq Ft
- Built 1988
Last Sold Summary
- $426/SF
- 15 Days On Market
Last Listing Agent Janet Short Houlihan Lawrence Inc.

149 King St Unit 15, Chappaqua, NY 10514

Not Listed For Sale

219 Hamilton Rd, Chappaqua, NY 10514
- 6 Beds
- 4.5 Baths
- 4,692 Sq Ft
- Built 1929
219 Hamilton Rd, Chappaqua, NY 10514

Last Sold Summary
- $474/SF
- 11 Days On Market
Last Sold Price $2,225,000

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

/18
$699,000
- 2 Beds
- 2.5 Baths
- 1,483 Sq Ft
150 N Bedford Rd Unit 6D, Chappaqua, NY 10514

Immaculate townhouse in a desirable walk-to-town location close to shops, restaurants, and the train. Refinished maple hardwood floors, custom built-ins, and a fireplace define the main living level, highlighted by a dramatic wall of windows with sunset views. Newer Pella sliders open to a private deck for seamless indoor-outdoor living. Custom stair railings, upgraded solid interior doors, and

Sari Shaw Compass Greater NY, LLC

150 N Bedford Rd Unit 6D, Chappaqua, NY 10514
$1,632,000 Sold Apr 21, 2025

81 Cross Ridge Rd, Chappaqua, NY 10514
- 4 Beds
- 3 Baths
- 3,211 Sq Ft
- Built 1963
Last Sold Summary
- 17% Above List Price
- $508/SF
- 14 Days On Market
Current Estimated Value $1,699,095

Last Listing Agent Pamela Akin Douglas Elliman Real Estate

81 Cross Ridge Rd, Chappaqua, NY 10514

Est $1,642,651 Not Listed For Sale

370 Sarles St, Mount Kisco, NY 10549
- 4 Beds
- 3.5 Baths
- 2,973 Sq Ft
- Built 1908
370 Sarles St, Mount Kisco, NY 10549

Last Sold Summary
- 8% Above List Price
- $514/SF
- 27 Days On Market
Last Sold Price $1,527,000

Last Listing Agent Jody Rosen Julia B Fee Sothebys Int. Rlty

/20
$475,000
- 1 Bed
- 1.5 Baths
- 1,207 Sq Ft
356 N Greeley Ave Unit 28G, Chappaqua, NY 10514

Location, Location, Location! Chestnut Oak Complex. Dramatic and bright townhouse with natural lighting. This 1 bedroom 1.1 bath plus huge Loft/Den is in mint condition. Updated kitchen with stainless-steel appliances. Living room with high ceilings, fireplace and wall of windows is combined with spacious dining area. Updated powder room on the first level. Huge primary bedroom with with two

Alicja Bohmrich Houlihan Lawrence Inc.

356 N Greeley Ave Unit 28G, Chappaqua, NY 10514
$1,040,000 Sold Nov 25, 2025

81 Hidden Hollow Ln, Millwood, NY 10546
- 4 Beds
- 2.5 Baths
- 2,368 Sq Ft
- Built 1971
Last Sold Summary
- 1% Below List Price
- $439/SF
- 53 Days On Market
Current Estimated Value $1,062,074

Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

81 Hidden Hollow Ln, Millwood, NY 10546

Est $2,520,515 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
- 3% Below List Price
- $609/SF
- 13 Days On Market
Last Sold Price $2,588,444

Last Listing Agent Heather Bouza William Raveis-New York, LLC

/30
$1,249,000
- 4 Beds
- 3 Baths
- 2,940 Sq Ft
508 Millwood Rd, Mount Kisco, NY 10549

Set back from the road on beautifully landscaped grounds, this inviting Colonial offers a rare combination of privacy and refined modern living within the highly sought-after Chappaqua School District. Thoughtfully designed and beautifully updated, the home features four bedrooms and could comfortably live as five, with three full bathrooms and generous, well-proportioned living spaces

Jennifer Harris Compass Greater NY, LLC

508 Millwood Rd, Mount Kisco, NY 10549
$1,600,000 Sold Jul 22, 2025

6 Dewitt Dr Unit 65, Chappaqua, NY 10514
- 2 Beds
- 3.5 Baths
- 3,353 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $477/SF
- 66 Days On Market
Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

6 Dewitt Dr Unit 65, Chappaqua, NY 10514

Est $1,686,917 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
- 24% Above List Price
- $336/SF
- 13 Days On Market
Last Sold Price $1,361,000

Last Listing Agent Eric Stein RE/MAX

/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
$2,260,000 Sold May 02, 2025

8 Kitchel Rd, Mount Kisco, NY 10549
- 4 Beds
- 3.5 Baths
- 5,376 Sq Ft
- Built 2006
Last Sold Summary
- 6% Below List Price
- $420/SF
- 43 Days On Market
Current Estimated Value $2,252,316

Last Listing Agent Cindy Glynn Compass Greater NY, LLC

8 Kitchel Rd, Mount Kisco, NY 10549

Est $1,786,853 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% Above List Price
- $434/SF
- 12 Days On Market
Last Sold Price $1,600,018

Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

/30
$1,299,999 Open Sun 12PM - 2PM
- 4 Beds
- 2.5 Baths
- 2,460 Sq Ft
114 Old Lyme Rd, Chappaqua, NY 10514

Meticulously maintained and move-in ready, this light-filled 4-bedroom, 2.5-bath contemporary is set on one of Chappaqua’s most desirable streets. The open-concept layout offers seamless flow for everyday living and entertaining, enhanced by exceptional natural light throughout provided by pristine windows. Updated baths in 2025 bring a fresh, modern feel, complementing the home’s clean

Sari Shaw Compass Greater NY, LLC

114 Old Lyme Rd, Chappaqua, NY 10514

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