Westchester, NY Homes

/40
$1,295,000
- 2 Beds
- 2 Baths
- 2,344 Sq Ft
5 Shingle House Rd, Millwood, NY 10546

Retreat into a world of elegance and charm in this Enchanted Storybook Cottage located in the Chappaqua School District. Privately sited down a long private drive on 3.2 maturely landscaped acres, sits this whimsical craftsman style home. The well maintained impressive interior features elegant tile, wide plank wood flooring, pocket doors, archways, hand hewn beams and 2 magnificent stone

Amber Thomas Compass Greater NY, LLC

5 Shingle House Rd, Millwood, NY 10546
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/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
$1,615,000 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

Est $2,466,466 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 4,249 Sq Ft
16 Kittle Rd, Chappaqua, NY 10514

16 Kittle Rd, Chappaqua, NY 10514

/28
$1,425,000 Pending
- 4 Beds
- 4 Baths
- 3,072 Sq Ft
3 Kitchel Rd, Mount Kisco, NY 10549

NEW PRICE!! Don't miss this timeless and refined Colonial nestled in the heart of Chappaqua’s prestigious Lawrence Farms East neighborhood. Set on a spectacular park-like property, this classic home combines classic sited on beautifully landscaped grounds, features expansive green lawns, sweeping rear views, and charming stone walls that frame the property. A Belgium block-lined driveway leads

Cindy Glynn Compass Greater NY, LLC

3 Kitchel 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
$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

Est $1,740,250 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 4,045 Sq Ft
55 Cowdin Cir, Chappaqua, NY 10514

55 Cowdin Cir, Chappaqua, NY 10514

/34
$1,375,000 Pending
- 3 Beds
- 3 Baths
- 3,102 Sq Ft
42 Cross Ridge Rd, Chappaqua, NY 10514

Meticulously maintained move-in ready home on a park-like acre with an incredible flat, usable and private backyard with extensive mature trees and landscaping. This 3 bedroom/ 3 full bathroom house with hardwood flooring and recessed lighting throughout, has a perfect option for an additional guest bedroom/ office on the first floor and countless special features such as an in-ground sprinkler

Pamela Akin Douglas Elliman Real Estate

42 Cross Ridge Rd, 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
$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

Est $1,672,989 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,402 Sq Ft
515 Bedford Rd, Chappaqua, NY 10514

515 Bedford Rd, Chappaqua, NY 10514

/4
$1,338,995 Pending
- 2 Beds
- 2.5 Baths
- 2,503 Sq Ft
14 Carriage Ln Unit 87, Chappaqua, NY 10514

HOME IS UNDER CONSTRUCTION- READY FOR Summer 2025 closing 2 BR Briarcliff Floorplan with primary on first floor. You can still add structural and design features to this home. This outstanding home is located in a great location facing greenspace on one side and forest views from the rooftop deck. It is located in the heart of the neighborhood where you can walk to shopping, cafes,

Thomas Jacovino Toll Brothers Real Estate Inc.

14 Carriage Ln Unit 87, 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
$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

Est $1,712,316 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 3,930 Sq Ft
512 Bedford Rd, Mount Kisco, NY 10549

512 Bedford Rd, Mount Kisco, NY 10549

/34
$1,099,000 Open Sat 1PM - 3PM
- 3 Beds
- 2.5 Baths
- 2,195 Sq Ft
4 Oak Hill Rd, Chappaqua, NY 10514

Enjoy easy living in this fully renovated Cape Cod style home situated on a park-like, flat property. Located walking distance to town and train, this 3 bedroom/2.5 bathroom residence offers modern luxuries in a classic country-feeling home. Enter this home through an inviting foyer flanked by a front-to-back living room, featuring a wood-burning fireplace and a formal dining

Allison Tintenfass Compass Greater NY, LLC

4 Oak Hill Rd, Chappaqua, NY 10514
/30
$4,250 per month
- 4 Beds
- 1 Bath
- 1,100 Sq Ft
- Apartment for Rent
227 Saw Mill River Rd, Millwood, NY 10546

Welcome to this beautifully renovated 4 bed, 1bath apartment in the heart of Millwood. Thoughtfully renovated to modern standards, this residence blends style and function for those seeking a tranquil lifestyle in a charming town.Step inside and admire the details of this home, from porcelain floor tiles with a luxurious marble finish to illuminating recessed lighting throughout, this

Chintan Trivedi RE/MAX In The City

227 Saw Mill River Rd, Millwood, NY 10546
$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

Est $633,651 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,266 Sq Ft
10 Birch Dr, Mount Kisco, NY 10549

10 Birch Dr, Mount Kisco, NY 10549

/6
$1,090,000
- 3 Beds
- 2.5 Baths
- 3,990 Sq Ft
81 Glendale Rd, Ossining, NY 10562

Fantastic find for nature lovers seeking total stillness away form the City hustle and bustle, just a short 1 hr train ride from Manhattan! 14.5 wooded acres with beautiful stone outcroppings and a few clearings, suitable for chickens, goats and/or horses. The property has rustic outbuildings and walking paths that connect to Teatown trails. This home has large rooms with possibility for in-law

Helena Macintyre North Country Sothebys Int Rlt

81 Glendale Rd, Ossining, NY 10562
/26
$9,500 per month
- 4 Beds
- 4 Baths
- 3,000 Sq Ft
- House for Rent
306 Quaker Rd, Chappaqua, NY 10514

Smartly renovated 1930's Colonial walking distance to town, train, shops & school. Impressive columned front portico w/double-door entry. Formal living room w/fireplace & crown molding. Formal dining room w/French doors to patio & crown molding. High-end kitchen features Wolf, Fisher Paykel & Bosch appliances open to family room w/cathedral ceiling & French doors to patio. Main floor den/office

Stacy Levey William Raveis-New York, LLC

306 Quaker Rd, 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

Est $957,853 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,168 Sq Ft
120 Harriman Rd, Mount Kisco, NY 10549

120 Harriman Rd, Mount Kisco, NY 10549

/29
$1,200,000
- 4 Beds
- 3.5 Baths
- 3,776 Sq Ft
6 Algonquin Dr, Chappaqua, NY 10514

Tucked back on a private corner lot on one of Chappaqua’s most desirable and quiet streets, this expanded mid-century ranch offers a rare opportunity to create your dream home in an award-winning school district. The property is well situated on the lot, leaving plenty of space for a pool or future outdoor expansion.Inside, the home offers a light-filled layout with generously sized

Lindsay Rothman Compass Greater NY LLC

6 Algonquin Dr, Chappaqua, NY 10514
/19
$5,500 per month
- 3 Beds
- 1.5 Baths
- 1,386 Sq Ft
- Townhouse for Rent
29 Stone Creek Ln, Briarcliff Manor, NY 10510

A spacious and extremely comfortable townhouse for rent is located in the Stone Creek Townhouse Community. This townhome offers a spacious home in a beautiful environment. A quaint 3 bedroom home with 1 full updated bathroom,1 1/2 bathroom, a fully renovated kitchen, and large living space where residents can gather and enjoy free time together. The community has well maintained lawns where

Gerard Collins Corcoran Legends Realty

29 Stone Creek Ln, Briarcliff Manor, NY 10510
$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

Est $1,290,512 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,309 Sq Ft
4 Grayrock Pk Rd, Mount Kisco, NY 10549

4 Grayrock Pk Rd, Mount Kisco, NY 10549

/31
$799,000
- 4 Beds
- 2 Baths
- 1,420 Sq Ft
37 Hollow Oak Rd, Chappaqua, NY 10514

Charming and lovingly maintained cape cod home on beautiful private property. Located in the sought after Chappaqua Ridge neighborhood ,this home offers town water, sewer and natural gas, and is minutes to town, train and schools. The first floor features an open kitchen/dining/ living room plus 2 bedrooms and a bath. One of the bedrooms could also be used as a home office. There are sliders out

Lauren Goldenberg William Raveis Real Estate

37 Hollow Oak Rd, Chappaqua, NY 10514
/8
$3,500 per month
- 1 Bed
- 1 Bath
- 670 Sq Ft
- Apartment for Rent
91 Bedford Rd Unit 2, Chappaqua, NY 10514

This lovely one bedroom plus den apartment features an EIK with glamourous modern style quartz counters, bright open floor plan. Individual balcony. Storage closet included. HW/heater, washer/dryer. Quality construction built by highly regarded local builder. Amenities of this architecturally inspired building include Access control intercom/security cameras, FOB. Steel and concrete frame

Grace Priore ERA Insite Realty Services

91 Bedford Rd Unit 2, Chappaqua, NY 10514
$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 $2,735,999 Not Listed For Sale
- 4 Beds
- 6 Baths
- 5,653 Sq Ft
27 Petersville Rd, Mount Kisco, NY 10549

27 Petersville Rd, Mount Kisco, NY 10549

/27
$1,150,000
- 4 Beds
- 2.5 Baths
- 3,264 Sq Ft
569 Millwood Rd, Chappaqua, NY 10514

A dramatic and stunning four-bedroom Contemporary home set on 1.2 professionally landscaped acres, designed by Jan Johnsen, former landscape architect for the New York Botanical Gardens. Surrounded by wooded privacy, this serene setting features two separate decks and a ground-level patio that surrounds the exterior of the home. Inside, this home offers a light-filled, modern, and open layout

Edward Holmes William Raveis-New York, LLC

569 Millwood Rd, Chappaqua, NY 10514
/23
$4,700 per month
- 2 Beds
- 2 Baths
- 1,724 Sq Ft
- Condo for Rent
177 Birchwood Close Unit 177, Chappaqua, NY 10514

Beautifully maintained and renovated 2 bedroom unit: all new windows, new kitchen, new bathroom, new heating and HVAC-huge storage unit in basement, lots of storage-flooded with sunlight, private deck. Wonderful location. Sought-after OLD FARM LAKE complex. Shared complex amenities include pool, tennis and clubhouse with exercise room. Minutes from Chappaqua Train Station - great for

Wendy Nolan Houlihan Lawrence Inc.

177 Birchwood Close Unit 177, Chappaqua, NY 10514
$1,200,000 Sold Jul 29, 2025
- 2,559 Sq Ft
- $469/SF
- 19 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1980
174 Somerstown Rd, Millwood, NY 10546

Built as a custom home in 1980, this completely renovated four bedroom contemporary home in the Chappaqua school district is set very nicely away from the road offering wonderful privacy. The home boasts an open floor plan and a stunning double-height skylit living room bathed in natural light and anchored by a wood burning fireplace. The high-end kitchen is a chef's dream, featuring custom

Amanda Goldberg William Raveis-New York, LLC

174 Somerstown Rd, Millwood, NY 10546

Est $2,828,824 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 6,334 Sq Ft
12 Petersville Rd, Mount Kisco, NY 10549

12 Petersville Rd, Mount Kisco, NY 10549

/43
$775,000 Open Sun 12PM - 2PM
- 2 Beds
- 2 Baths
- 1,549 Sq Ft
77 Further Ln, Chappaqua, NY 10514

Fully Available!Discover exceptional living in this well maintained 2-bedroom, 2-bath townhome.A true gem within Chappaqua's coveted Old Farm Lake community. Enjoy lake views from your back deck or use the electric roller shades for the living room view. This unique unit boasts a front lawn, inviting patio, and lush landscaping overlooking a picturesque pond. The kitchen

Clayton Livingston McGrath Realty Inc

77 Further Ln, Chappaqua, NY 10514
/26
$2,900 per month
- 1 Bed
- 1 Bath
- 900 Sq Ft
- Condo for Rent
150 N Bedford Rd Unit 5A, Chappaqua, NY 10514

This spacious townhouse is waiting for you to come home! This well-appointed one-bedroom, one-bathroom home will pleasantly surprise you. As you enter the house, a large living area will greet you with polished wooden flooring and plenty of sunlight from the floor-to-ceiling windows. The adjoining kitchen is stylish and practical, with ample wooden cabinets contrasting beautifully with the dark

Xiao Hua Herman NextHome GoodLife

150 N Bedford Rd Unit 5A, Chappaqua, NY 10514
$995,000 Sold Jul 28, 2025
- 5,227 Sq Ft
- $190/SF
- 55 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1900
2 Woodmill Rd, Chappaqua, NY 10514

Spacious Turn-of-the-Century Converted Cider Mill – A True One-of-a-Kind Home! Nestled on just over 1 acre of lush property, this sprawling and unique home was once a cider mill and has been beautifully converted into a spacious residence. Boasting 3 working fireplaces and retaining many of its original architectural details, this home exudes character and charm. With hardwood floors, high wood

Mark Seiden Mark Seiden Real Estate Team

2 Woodmill Rd, Chappaqua, NY 10514

Est $2,582,578 Not Listed For Sale
- 4 Beds
- 6 Baths
- 5,600 Sq Ft
76 Cowdin Ln, Chappaqua, NY 10514

76 Cowdin Ln, Chappaqua, NY 10514

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