Westchester, NY Homes

/27
$210,000
- 2 Beds
- 1 Bath
- 672 Sq Ft
135 - 6 Highland Ave S Unit D1, Ossining, NY 10562

Discover this charming, updated two-bedroom co-op in highly sought-after Highland Terrace. This unique unit offers the convenience of both a main building entrance and its own private entry. Inside, you'll find a spacious and bright primary bedroom with ample closet space, while the versatile second bedroom That is currently being utilized as a home office. Abundant windows fill the living areas

Sherry Wiggs

Houlihan Lawrence Inc.

(914) 601-2993

135 - 6 Highland Ave S Unit D1, Ossining, NY 10562
/12
$9,400 per month
- 4 Beds
- 3.5 Baths
- 2,468 Sq Ft
- House for Rent
187 Croton Ave, Mount Kisco, NY 10549

Move right in to this bright and sunny recently renovated 4 bedroom home in the Chappaqua School District. Enjoy easy living and a great layout for entertaining family and friends. Open concept kitchen - family room with access to wrap around deck and great yard. 1st floor primary with renovated en-suite, walk in closet and sliders to deck, living room, dining room and powder room complete the

Deena Bouchier

Compass Greater NY, LLC

(914) 814-6734

187 Croton Ave, Mount Kisco, NY 10549
$1,445,000 Sold Aug 07, 2025
- 2,652 Sq Ft
- $545/SF
- 5 Days On Market
- 3 Beds
- 3 Baths
- Built 1951
12 Pond Hill Rd, Chappaqua, NY 10514

Picture perfect Cape on level landscaped property with lush lawns radiates curb appeal. Beautifully updated and impeccably maintained with a blend of classic charm and modern luxury. Light-filled rooms with gleaming hardwood floors enhance the well proportioned living spaces. The renovated eat-in kitchen features white cabinetry, stainless steel appliances, quartz countertops and tasteful

Jennifer Harris Compass Greater NY, LLC

12 Pond Hill Rd, Chappaqua, NY 10514

Est $920,596 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,688 Sq Ft
16 Seth Canyon Dr, Mount Kisco, NY 10549

16 Seth Canyon Dr, Mount Kisco, NY 10549

/35
$1,350,000 Pending
- 6 Beds
- 4 Baths
- 5,034 Sq Ft
62 Taconic Rd, Millwood, NY 10546

MOTIVATED SELLER! PRICE REDUCED! Welcome to this spacious, peaceful, and impeccably maintained 6-bedroom, 4-bathroom home with tennis court and pool in the highly sought-after Chappaqua School District (Millwood). This home offers 5,034 sq ft of move-in ready living space on a scenic and private 2-acre lot. The large rooms and easy layout provide the perfect canvas to create your dream home

Hillary Landau

Compass Greater NY, LLC

(914) 996-2889

62 Taconic Rd, Millwood, NY 10546
/25

$2,400 - $6,850 per month

Chappaqua Crossing Apartments

1 - 3 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
$875,000 Sold Aug 06, 2025
- 2,541 Sq Ft
- $344/SF
- 32 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1964
341 Millwood Rd, Chappaqua, NY 10514

Nestled on nearly 2 acres of serene, wooded land, this beautifully maintained 4-bedroom, 2.5-bath home offers space, comfort, and privacy. The bright and airy eat-in kitchen features abundant cabinet space, a convenient in-kitchen laundry, and a large picture window overlooking the scenic backyard. A sun-filled living room with an oversized picture window enhances the home's warm and inviting

Jo Ann Reilly Julia B Fee Sothebys Int. Rlty

341 Millwood Rd, Chappaqua, NY 10514

Est $666,647 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,918 Sq Ft
36 Ledgewood Commons, Millwood, NY 10546

36 Ledgewood Commons, Millwood, NY 10546

/49
$2,200,000
- 5 Beds
- 4.5 Baths
- 4,172 Sq Ft
77 Haights Cross Rd, Chappaqua, NY 10514

Timeless elegance meets modern comfort in this enchanting 1901 hunting lodge, masterfully restored in 1991 and recently enhanced. Set on beautifully landscaped grounds with lush gardens, this distinguished home features a dramatic front portico, high ceilings, intricate millwork, and unique architectural details throughout. Grand living spaces include a library/home office with French doors and

Joshua Rogull Julia B Fee Sothebys Int. Rlty

77 Haights Cross Rd, Chappaqua, NY 10514
/12
$4,500 per month
- 2 Beds
- 2.5 Baths
- 1,408 Sq Ft
- Townhouse for Rent
82 Pheasant Run Unit 82B, Millwood, NY 10546

Welcome to this beautifully updated 2-bedroom, 2.5-bath condo in the desirable Pheasant Run community. Located in the Chappaqua School District, this home offers the perfect blend of comfort, convenience, and lifestyle.The main level offers a welcoming layout with an eat-in kitchen that opens to the spacious living and dining area—ideal for entertaining. Enjoy cozy evenings by the

Jill Urban Compass Greater NY, LLC

82 Pheasant Run Unit 82B, Millwood, NY 10546
$1,615,000 Sold Aug 01, 2025
- 4,099 Sq Ft
- $394/SF
- 13 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1985
7 High Point Cir, Chappaqua, NY 10514

Beautifully positioned at the end of a quiet cul-de-sac, this contemporary home offers style and serenity in a prime Chappaqua location. Designed with today’s lifestyle in mind, the open and airy floor plan features soaring ceilings, floor-to-ceiling windows, and sun-drenched spaces throughout. A beautifully updated modern kitchen flows seamlessly into expansive living and dining areas, ideal for

Cindy Glynn Compass Greater NY, LLC

7 High Point Cir, Chappaqua, NY 10514

Not Listed For Sale
- 4 Beds
767 King St, Chappaqua, NY 10514

767 King St, Chappaqua, NY 10514

/44
$1,774,000
- 3 Beds
- 3.5 Baths
- 3,614 Sq Ft
21 Wallace Way, Chappaqua, NY 10514

Better than new at Chappaqua Crossings Carriages! Be among the first to experience this spectacular new community featuring a delightful and charming village atmosphere in the heart of Westchester, Chappaqua, NY. This stunning “Byram Newhaven model” situated in a prime location within the community, offers great curb appeal with its expansive front porch, stone walls and specimen plantings; and

Ken Wile Redfin Real Estate

21 Wallace Way, Chappaqua, NY 10514
/21
$6,250 per month
- 3 Beds
- 2 Baths
- 1,912 Sq Ft
- House for Rent
235 Douglas Rd, Chappaqua, NY 10514

This beautifully updated rental offers a bright, open layout and a prime location just under a mile from downtown Chappaqua and the Metro North station—perfect for easy commuting and enjoying all the local spots. Freshly painted and move-in ready, the home is available furnished or unfurnished.The main level features a sun-filled living and dining area, an updated kitchen, a spacious

Danielle Della Pella Compass Greater NY, LLC

235 Douglas Rd, Chappaqua, NY 10514
$600,000 Sold Aug 01, 2025
- 1,608 Sq Ft
- $373/SF
- 28 Days On Market
- 2 Beds
- 2 Baths
- Built 1988
324 N Greeley Ave, Chappaqua, NY 10514

Welcome to this beautifully renovated home in highly sought after Chestnut Oaks, steps from downtown Chappaqua. A rare opportunity to buy this end unit townhouse in the award-winning Chappaqua school district. This bright and spacious two-bedroom townhouse features a loft, its own washer/drier and balcony. Enjoy stress free living with low maintenance and taxes, close to town with a pool and

Nick Rie K. Fortuna Realty, Inc.

324 N Greeley Ave, Chappaqua, NY 10514

Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 4,477 Sq Ft
38 Taylor Rd, Mount Kisco, NY 10549

38 Taylor Rd, Mount Kisco, NY 10549

/9
$1,807,995 Pending
- 2 Beds
- 3.5 Baths
- 3,269 Sq Ft
2 Carriage Ln Unit 81, Chappaqua, NY 10514

HOME IS TO BE BUILT. 2 BR very popular Greeley Floorplan with primary on first floor. We have a model of this home to walk through. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner

Thomas Jacovino Toll Brothers Real Estate Inc.

2 Carriage Ln Unit 81, Chappaqua, NY 10514
/24
$9,750 per month
- 4 Beds
- 3.5 Baths
- 3,882 Sq Ft
- House for Rent
777 Armonk Rd, Mount Kisco, NY 10549

Set on over five secluded acres with picturesque pond and woodland views, this beautifully furnished 4-bedroom home offers a perfect blend of timeless character and modern comfort. Ideal for short- or long-term stays, the residence is thoughtfully designed for both relaxation and functionality.The main level welcomes you with a gracious entry foyer, a chef’s kitchen with premium

Mark Sanford Berkshire Hathaway HS NE Prop.

777 Armonk Rd, Mount Kisco, NY 10549
$2,500,000 Sold Aug 01, 2025
- 6,612 Sq Ft
- $378/SF
- 47 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2012
177 Somerstown Rd, Millwood, NY 10546

California dreaming’ but East Coast leaning? You can catch the bi-coastal wave in this masterfully built & deliciously designed modern home which at once combines Santa Monica & Scandinavia. Glass, steel, cement & brick both gird & grace this built to stand for centuries place. Why settle for a house that settles? Wood-Free construction provides worry-free living & that peace of mind is

Owen Berkowitz Christie's Int. Real Estate

177 Somerstown Rd, Millwood, NY 10546

Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,280 Sq Ft
9 McKesson Hill Rd, Chappaqua, NY 10514

9 McKesson Hill Rd, Chappaqua, NY 10514

/35
$2,195,000 Open Sat 1PM - 3PM
- 4 Beds
- 3.5 Baths
- 4,004 Sq Ft
4 Circle Dr, Mount Kisco, NY 10549

Brand New Construction in the award-winning Chappaqua School District set on over one level acre. Ready for occupancy at the end of July or early August 2025 – just in time for the new school year. With 4 bedrooms and 3.1 bathrooms, it offers a flexible and functional layout with spacious, sunlit interiors that feel welcoming and refined. The open-concept living and dining areas are complemented

Aurora Banaszek Compass Greater NY, LLC

4 Circle Dr, Mount Kisco, NY 10549
/29
$5,000 per month
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
- House for Rent
49 Spring Valley Rd, Ossining, NY 10562

A rare rental opportunity for a totally renovated Vintage country estate set home. . 49 Spring Valley offers the perfect balance of peace and quiet in a location close to all the modern creature comforts you seek. Step inside the main house's freshly-painted entry hall and admire the gleaming hardwood flooring. The gourmet kitchen is the heart of the home, featuring granite counters, 42"

Maria Vele Keller Williams Realty Partner

49 Spring Valley Rd, Ossining, NY 10562
$2,050,000 Sold Jul 31, 2025
- 3,939 Sq Ft
- $520/SF
- 6 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1964
122 Valley View Rd, Chappaqua, NY 10514

Ideally located in the coveted Dodge Farms neighborhood, this classic Colonial offers an exceptional combination of space, charm, and functionality. Set on over 1.2 acres of lush, private property, this six-bedroom, 3.5-bath home is perfect for both everyday living and effortless entertaining. Step inside to find a sun-drenched main level featuring a spacious formal living room with a beautiful

Sari Shaw Compass Greater NY, LLC

122 Valley View Rd, Chappaqua, NY 10514

Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,427 Sq Ft
16 Maria Ln, Ossining, NY 10562

16 Maria Ln, Ossining, NY 10562

/16
$1,450,000
- 4 Beds
- 5 Baths
- 2,875 Sq Ft
136 Roaring Brook Rd, Chappaqua, NY 10514

Experience the pinnacle of refined living in this newly reimagined modern farmhouse, perfectly sited on a secluded, tree-lined acre in the heart of Chappaqua. With over 2,800 square feet of exquisitely finished space, this residence blends timeless architectural detail with sophisticated, high-end design for the ultimate in quiet luxury. Andersen 400 series windows and doors throughout, most are

Aric Wiser Douglas Elliman Real Estate

136 Roaring Brook Rd, Chappaqua, NY 10514
/35
$5,700 per month
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
- House for Rent
25 Maple Ave, Chappaqua, NY 10514

Charming 3-Bedroom, 2-Bath Home in the Heart of Chappaqua!Welcome to this beautifully updated home located just steps from the train, shops, schools, and restaurants in vibrant downtown Chappaqua. This move-in ready residence features three spacious bedrooms and two full bathrooms, perfect for comfortable family living.Recent upgrades include fresh interior paint, new

Heidi Oliver Houlihan Lawrence Inc.

25 Maple Ave, Chappaqua, NY 10514
$1,200,000 Sold Jul 31, 2025
- 2,251 Sq Ft
- $533/SF
- 20 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1968
16 Gregory Ln, Millwood, NY 10546

Set on over an acre of park-like grounds on a quiet double cul-de-sac, this classic Millwood residence offers refined living in one of Westchester’s most desirable enclaves. Framed by mature trees and natural beauty, the home combines timeless design with modern comforts—all within the award-winning Chappaqua School District. A gracious entry opens to an oversized formal living room, where three

Adriane Defeo Compass Greater NY, LLC

16 Gregory Ln, Millwood, NY 10546

Not Listed For Sale
- 6 Beds
- 5 Baths
- 3,853 Sq Ft
229 Pinesbridge Rd, Ossining, NY 10562

229 Pinesbridge Rd, Ossining, NY 10562

/36
$1,795,000
- 4 Beds
- 3.5 Baths
- 4,576 Sq Ft
20 Little Pine Rd, Mount Kisco, NY 10549

Located at the end of a quiet cul-de-sac, 20 Little Pine Road is a Modern Farmhouse Colonial situated on over an acre of beautifully landscaped grounds. Interior spaces are light and fresh with a wonderful floorplan for everyday living. Approximately 4600 square feet, it houses nine main rooms on two levels. There is additional finished living space in the walk-out lower level. Interior spaces

Mary Dowdle Ginnel Real Estate

20 Little Pine Rd, Mount Kisco, NY 10549
/9
$2,100 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.

Mary Grant Houlihan Lawrence Inc.

85 Paulding Dr, Chappaqua, NY 10514
$2,875,000 Sold Jul 31, 2025
- 7,038 Sq Ft
- $408/SF
- 63 Days On Market
- 5 Beds
- 6.5 Baths
- Built 1989
26 Hemlock Hills, Chappaqua, NY 10514

Introducing this spectacular country retreat, nestled peacefully on over four and a half acres in the leafy and much loved hamlet of Chappaqua. A glorious heated pool, panoramic patios, and endless lawns for play - offering complete privacy and seclusion, while just minutes from Chappaqua’s vibrant downtown and top-rated schools! At the end of the long scenic drive, an architectural beauty

Wendy Alper Julia B Fee Sothebys Int. Rlty

26 Hemlock Hills, Chappaqua, NY 10514

Not Listed For Sale
- 8 Beds
- 8 Baths
- 5,337 Sq Ft
51 Pinesbridge Rd, Ossining, NY 10562

51 Pinesbridge Rd, Ossining, NY 10562

/43
$2,000,000
- 6 Beds
- 6 Baths
- 5,234 Sq Ft
50 Overlook Dr, Chappaqua, NY 10514

50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors. This one-of-a-kind home is a must see. Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can

Wendy Nolan Houlihan Lawrence Inc.

50 Overlook Dr, Chappaqua, NY 10514
/17
$4,995 per month
- 3 Beds
- 1.5 Baths
- 2,200 Sq Ft
- Apartment for Rent
52 Orchard Ridge Rd, Chappaqua, NY 10514

Multi-level home featuring large rms and open plan kitch/dining area. Bdrm's are located upstairs and are well sized with beautiful crown molding and large closets. Large, flat backyard perfect for play, outdoor BBQ & entertaining includes your own small garden to grow fresh vegetables for the family. Kitchen with granite countertops, natural gas stove and stainless steel appliances. Mudroom and

Valon Nikci Link NY Realty

52 Orchard Ridge Rd, Chappaqua, NY 10514
$1,804,000 Sold Jul 31, 2025
- 3,219 Sq Ft
- $560/SF
- 7 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1972
10 Glen Terrace, Chappaqua, NY 10514

Discover the perfect blend of elegance and comfort in this beautifully updated four-bedroom colonial, nestled in the coveted Glen Terrace cul-de-sac. This exceptional home is filled with natural light, enhanced by designer-selected colors, stylish light fixtures, and recessed lighting.The heart of the home is the spacious eat-in kitchen, featuring premium finishes such as Emerald Green

Brendan Preston Houlihan Lawrence Inc.

10 Glen Terrace, Chappaqua, NY 10514

Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,644 Sq Ft
130 Pinesbridge Rd, Ossining, NY 10562

130 Pinesbridge Rd, Ossining, NY 10562

/34
$1,799,999
- 4 Beds
- 3 Baths
- 3,009 Sq Ft
200 Millwood Rd, Chappaqua, NY 10514

Tucked away in a 3+ acre private storybook setting, this reimagined farmhouse blends timeless charm with modern comfort. Set back from the road on a scenic, private property with gorgeous mature landscaping, two tranquil ponds, and wide-open views, this 4-bedroom home is a peaceful retreat unlike any other.Inside, the open, sunlit layout features oversized windows that invite the outdoors in,

Sari Shaw Compass Greater NY, LLC

200 Millwood Rd, Chappaqua, NY 10514
/19
$6,400 per month
- 2 Beds
- 4 Baths
- 2,200 Sq Ft
- Condo for Rent
11 Station Place Unit 9, Millwood, NY 10546

Luxury Town House Rental - In Chappaqua Schools. Hardwood floors, stainless steel appliances, granite counters and island, elevator to all floors, crown molding. High ceilings, full sized laundry front loaders on bedroom level. Gas fireplace in LR. Large floored attic for storage. Convenient to shops, restaurant, pharmacy, biking trail across street, elementary, Gedney Park, sports fields and

Cindy Glynn Compass Greater NY, LLC

11 Station Place Unit 9, Millwood, NY 10546
$999,000 Sold Jul 29, 2025
- 2,609 Sq Ft
- $383/SF
- 6 Days On Market
- 3 Beds
- 3 Baths
- Built 1927
185 Harriman Rd, Mount Kisco, NY 10549

Nestled on one of Mount Kisco’s most picturesque streets, this beautifully updated three-bedroom home blends timeless charm with modern comfort. Just a short stroll from Burden Preserve and Leonard Park, the location offers both convenience and a tranquil, nature-filled setting. Move-in ready and filled with natural light, the classic first-floor layout features a gracious living room, an

Sonya Cronin Julia B Fee Sothebys Int. Rlty

185 Harriman Rd, Mount Kisco, NY 10549

Est $1,569,374 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,973 Sq Ft
370 Sarles St, Mount Kisco, NY 10549

370 Sarles St, Mount Kisco, NY 10549

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