5 Bedroom Homes for Sale in Westchester, NY

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Welcome to your dedicated resource for 5 bedroom homes for sale in Westchester, NY. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Westchester, NY agent, Tierra Stanback specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 5 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All 5 Bedroom Homes for Sale in Westchester, NY

$2,299,000

5 Beds ⋅ 5 Baths ⋅ 1036792 MLS

Welcome to 20 Hitching Post Lane in Chappaqua, New York. This five-bedroom, 4.1 bath Colonial is set on over 2 bucolic acres on a beautiful tree-lined street. An impressive oak floored entry foyer with cherry inlay opens to a spacious formal living room with crown moldings and new windows (2023), warmed by a wood burning fireplace with decorative mantle. The adjacent family room has a second wood burning fireplace, this one brick, spanning floor-to-ceiling with raised hearth. Sliding glass doors lead from the Family Room to an Azek deck installed in 2016. Walk through the formal dining room accented with chair rail and crown molding, into a chef's kitchen with Richmaid cabinetry and tumbled marble backsplash with hand painted accents, a center island, and GE Monogram 6 burner gas stove with convection oven, farm sink, GE Monogram side/side refrigerator, microwave and dishwasher. Sliding glass doors open from the kitchen to deck with internal shades. The second floor Primary bedroom has a private bath with steam shower, double vanity and a Crema Marfil counter, whirlpool tub and radiant heated stone floors. The walk out lower level is included in the square footage and has a laundry room, playroom and a full bath. The mechanicals include: 4 zone heat, 3 zone AC, sophisticated sound system and CAT 5 wiring, full house generator (2014) Azek deck with an automated awning, fenced in yard, above ground oil tank (2024) and irrigation system. Enjoy this professionally landscaped retreat, minutes from downtown with easy Metro-North railroad service to New York City.

20 Hitching Post Lane, Chappaqua

$975,000

5 Beds ⋅ 4 Baths ⋅ 1051320 MLS

Step into a home where history lives and every room has a story to tell. Nestled in the heart of Yorktown Heights, this extraordinary Colonial Farmhouse is far more than an older home, it’s a rare piece of the community’s history, thoughtfully preserved while offering endless possibilities for today’s lifestyle. The home features 4 bedrooms and 3 full baths, while adjoining a lovely 1-bedroom, 1-bath that is perfect for extended family, guests, rental income, or a private home office. Set on a generous property, the home beautifully blends historic charm with Mid-Century charm, creating a warm, inviting atmosphere that’s impossible to duplicate. Just minutes from shopping, restaurants, major highways, and public transportation, you’ll enjoy the convenience of modern living while owning a home with roots that stretch back generations. Over the years, countless lives have passed through these doors, each adding another chapter to its remarkable story. Local historians have even documented the home’s history, giving its next owner the opportunity to become part of a legacy that has stood the test of time. Some homes are built. Others are remembered. This is your chance to own one of Yorktown’s most treasured and storied residences. Truly a must see!

2930 Gomer Street, Yorktown Heights

$1,600,000

5 Beds ⋅ 4 Baths ⋅ 1050017 MLS

Stunning brand new build you have been waiting for in lower Westchester. This contemporary colonial checks all the boxes. Well thought out open concept floorplan with hardwood floors throughout the home. Fantastic location close to schools, shopping, train, and great for all commuters. Main level flows effortlessly with an inviting entryway into a kitchen and living room perfect for entertaining. Upstairs you will find 4 spacious bedrooms including a primary suite with walk in closets and incredible views. Downstairs includes a finished basement with a walkout to your private backyard oasis.

25 Joan Avenue, White Plains

$1,250,000

5 Beds ⋅ 3 Baths ⋅ 1041701 MLS

Welcome to 5 Woodland Place, a captivating 1924 Colonial set on beautifully landscaped grounds in White Plains. With five bedrooms, two-and-a-half bathrooms, and 2,714 square feet of living space (the entire sq ft of the house is estimated at 3101), this home offers the character of a classic residence with the room and flexibility today’s buyers value. Step inside to sun-filled rooms, hardwood floors, original architectural details, and a warm, inviting atmosphere. The gracious living room features a fireplace, while the formal dining room is ready for everything from intimate dinners to larger celebrations. At the center of the home is a spacious kitchen with granite countertops, abundant cabinetry, a large island, breakfast bar, and pantry. A dedicated office provides a comfortable place to work or study. Upstairs, generously sized bedrooms offer peaceful retreats filled with natural light. An additional sitting room, recreation space, and partially finished walk-up attic. Lower Level provides even more room for guests, hobbies, fitness, or relaxation. Outside, sweeping lawns, mature trees, established gardens, and private stone patios create a beautiful setting for entertaining or simply unwinding. A long driveway and detached garage add convenience and valuable storage. Close to downtown White Plains, Metro-North, restaurants, shopping, parks, and major roadways, 5 Woodland Place brings together space, character, and convenience in one impressive property.

5 Woodland Place, White Plains

$679,999

5 Beds ⋅ 3 Baths ⋅ 1049415 MLS

Welcome to 15 Stewart Place, a beautifully renovated two-family home in Yonkers offering an excellent opportunity for both owner-occupants and investors. This multifamily property is being delivered VACANT, giving the new owner the flexibility to occupy, rent, or position both units immediately after closing. The home has undergone extensive renovations, creating updated living spaces while maintaining a practical multifamily layout. Improvements include updated plumbing and electrical systems, along with a newer roof and siding. The property offers 6 bedrooms and 3 full bathrooms across two residential units, providing generous space and multiple living configurations. Separate entrances add privacy and convenience between units. A full basement provides additional space, while the backyard offers room for outdoor enjoyment. Conveniently situated near Ashburton Avenue with access to shopping, parks, schools, public transportation, and major roadways. A strong opportunity to acquire a renovated, vacant-delivery two-family property in Yonkers—ideal for an end user looking to offset housing expenses with rental income or an investor seeking a multifamily asset without existing tenant occupancy. Move-in ready and positioned for its next owner.

15 Stewart Place, Yonkers

$5,795,000

5 Beds ⋅ 7 Baths ⋅ 1033235 MLS

Where timeless architecture meets resort-style living. Set within Scarsdale’s coveted Murray Hill Estate Section, this distinguished Georgian Colonial offers a rare combination of scale, privacy, craftsmanship, and refined luxury. Encompassing 1.41 acres at the highest elevation in Scarsdale, this gated legacy property is an exceptional private sanctuary, thoughtfully designed for both gracious living and effortless entertaining. From the moment of arrival, the home’s commanding street presence and enduring architectural character is evident. Grand proportions, high ceilings, oversized windows, rich hardwood floors (exposed and under carpet), elegant Greek dentil moldings, and stone fireplaces create a sense of permanence and sophistication throughout. At the heart of the residence is a remarkable St. Charles kitchen, appointed with custom hand-carved cherry wood cabinetry, granite countertops, and a distinctive stone fireside lounge—an inviting setting for intimate gatherings or memorable entertaining. Enjoy a seamless transition between indoor and outdoor living with a 2500 square foot flagstone courtyard, offering an exceptional setting for al fresco dining, entertaining, and effortless indoor-outdoor flow. The home’s extraordinary amenities rival those of a private resort. A heated indoor gunite diving pool anchors the wellness and recreation wing, complemented by a jacuzzi, dedicated spa room, sauna, and steam shower. The finished lower level offers additional living and entertaining space, a fireplace, exterior access, and additional plumbing lines, providing exceptional flexibility for future customization. With five bedrooms, seven full bathrooms, and two office/flex spaces, the residence offers an abundance of space for family, guests, work, and relaxation. Two generously sized attics provide substantial storage and additional possibilities. Outside, the expansive level grounds offer an extraordinary canvas for creating a true private resort. There is ample room to add an outdoor pool, tennis or basketball court, putting green, or other recreational amenities, while the estate’s elevated setting provides an exceptional sense of privacy and serenity. The property is equally impressive from a utility and infrastructure perspective, featuring a four-car garage, motor court accommodating up to 15 cars, Generac 80kW whole-house generator, five-zone HVAC, central vacuum, automated front gate, whole-house water purification, integrated sound system, home security, and extensive video surveillance system. This is more than a residence—it is a lifestyle. A rare opportunity to experience private, resort-inspired living in one of Scarsdale’s most prestigious estate enclaves, while remaining conveniently close to Scarsdale Village, top-rated schools, major highways, and transportation. Manhattan is less than an hour away by car, with Metro-North providing 30-minute access to Grand Central Terminal. A truly exceptional Scarsdale estate where timeless elegance, sophisticated amenities, and extraordinary privacy converge.

109 Mamaroneck Road, Scarsdale

$2,600,000

5 Beds ⋅ 4 Baths ⋅ 1048871 MLS

Offered for the first time by its original owner, direct waterfront on the Isle of Sans Souci, one of New Rochelle's most sought-after enclaves. Approximately 105 feet of seawall, with the backyard opening directly onto the beach below. Floor-to-ceiling windows carry the Sound into the family room off the kitchen, which opens to a wide deck above the large backyard, and from there down to the sand, usable at any tide. A sunken living room of generous proportion and a formal dining room complete the 2,800 SF main level. Four bedrooms and three full baths occupy the same floor. The primary suite faces south through a wall of windows, with an expansive view of the Sound straight across to Long Island, and offers an ensuite bath with double vanity and ample closet space. The 1,200 SF finished lower level of this 4,050 SF high ranch includes a fifth generously sized bedroom with full bath, a large open room long used for a bar, pool table, and media lounge, a summer wet bar, dedicated laundry room, and abundant storage. A two-car garage, half-moon front drive, and a long side driveway yield 8+ parking spaces. Membership in the 126-home Isle of Sans Souci Association conveys with ownership: a private gated beach club on a beautiful Sound inlet, with fire pit, kayak storage, bocce court, gazebo, dock, grills, and mooring rights. Pool, tennis, and basketball are available for a modest additional fee, well below what comparable clubs in the area charge. Waterfront on Sans Souci comes available rarely. This one never has.

73 Kensington Oval, New Rochelle

$675,000

5 Beds ⋅ 4 Baths ⋅ 1047732 MLS

WELCOME!! to this beautifully renovated 5-bedroom, 3.5-bath single-family home in the desirable Rockledge Heights neighborhood of Yonkers, thoughtfully designed with exceptional attention to detail. Enter through a spacious enclosed front porch featuring a conveniently placed washer and dryer. The main level offers a welcoming foyer, generous living room, comfortable family room, separate dining room, modern kitchen, and powder room. The second floor features three spacious bedrooms and a full bath, while the third floor offers two additional well-proportioned bedrooms and another full bath. The full walk-out basement includes two versatile utility rooms, a full bathroom, abundant storage, and endless possibilities. Completing this exceptional property is an impressive 25-by-195-foot lot. A private garden oasis with incredible outdoor potential, and parking facilities just steps away. The photos simply do not do this remarkable property justice. It must be seen to be fully appreciated!

183 Saratoga Avenue, Yonkers

$1,069,000

5 Beds ⋅ 2 Baths ⋅ 1048392 MLS

Attention investors and homebuyers: don’t miss this extraordinary find! Nestled at 40 Main Street, this impeccably updated two-family home in Dobbs Ferry blends timeless charm with modern sophistication. Positioned just minutes from the Metro-North train station, shops, restaurants, and the Dobbs Ferry Waterfront, this property offers convenience and lifestyle to match. The main floor unit features a bright and airy two-bedroom, one-bath layout, including a convenient back door entrance. The larger 3 bedroom 1 bathroom unit spans the second floor, boasting a private back patio, a covered porch, and a fully fenced yard, providing space for relaxation or entertaining. With its tasteful upgrades, private parking and unbeatable location to everything Dobbs Ferry has to offer, this property won’t stay on the market long. Schedule your private tour today and discover the blend of investment potential and move-in-ready appeal!

40 Main Street, Dobbs Ferry

$2,395,000

5 Beds ⋅ 4 Baths ⋅ 1034176 MLS

Turnkey luxury awaits in sought-after gated Morningside! Completely renovated with sophisticated finishes and exceptional attention to detail, this stunning home is designed for effortless everyday living and entertaining. A dramatic two-story foyer with radiant heated floors and custom glass railings opens to a formal living room with floor-to-ceiling stone fireplace, elegant dining room, and spectacular chef’s kitchen featuring premium appliances, custom cabinetry, propane cooking, oversized peninsula, radiant heat, and breakfast area. The adjoining family room with a second wood-burning fireplace opens to an expansive deck with propane hookup—perfect for outdoor entertaining. A flexible office/guest bedroom, custom mudroom, and oversized two-car garage with EV hookups complete the main level. Upstairs, the luxurious primary suite features custom walk-in closets and a spa-like bath with radiant heat, soaking tub, and oversized steam shower. Three additional bedrooms and beautifully renovated baths offer plenty of space for family and guests. The finished lower level, included in the square footage, provides exceptional flexibility for a playroom, gym, media room, guest suite, or au pair quarters. Smart lighting, new roof and condensers, new driveway and walkway, and professionally designed landscaping with elegant lighting complete this exceptional property. Enjoy the privacy and lifestyle of Morningside, with newly renovated basketball and pickleball courts. Move right in and enjoy one of Purchase’s most desirable gated communities!

6 Harrows Lane, Purchase

$699,000

5 Beds ⋅ 2 Baths ⋅ 1047324 MLS

931 2nd Street is a two-family property offering flexibility for both owner-occupants and investors. Each unit provides approximately 900 square feet of living space. The first-floor unit is vacant and features 2 bedrooms, 1 full bath, an eat-in kitchen, living room, and access to the yard, giving a new owner the opportunity for immediate occupancy or to select their own tenant. The second-floor unit features 3 bedrooms, 1 full bath, kitchen, and a private balcony, providing additional outdoor space. Located in the heart of Peekskill, the property offers convenient access to downtown shopping, dining, local amenities, and transportation. With two separate units and a vacant first floor, 931 2nd Street presents an opportunity to live in one unit while generating rental income from the other or add a multifamily property to an investment portfolio. Square footage is approximate; buyers and buyers' agents should independently verify all information.

931 2nd Street, Peekskill

$2,900,000

5 Beds ⋅ 5 Baths ⋅ 1037090 MLS

Set behind stone pillars at the end of a meandering private drive, this custom-built stone manor draws its inspiration from a 19th-century English manor house. This home features a rare blend of Old World craftsmanship and modern-day comfort on more than four private, lushly landscaped acres, just about an hour from New York City. Built in 1988 and thoughtfully updated since, the residence features Five fireplaces anchor the home's principal rooms. The living room, a soaring 39' x 24' space with 12' coffered pine ceilings and a massive floor-to-ceiling stone fireplace, sets a formal yet inviting tone, while the library's built-in cabinetry and Art Deco lighting bring a warmer, more contemporary counterpoint. The gourmet kitchen is a true tour de force, outfitted with Neff cabinetry, Viking appliances, and its own floor-to-ceiling stone fireplace. A library with French doors opens directly onto a stone terrace, ideal for quiet mornings or evening entertaining. Upstairs, the primary suite is accessed through a generous sitting room/office with its own fireplace and continues into a bedroom with a tray ceiling and another fireplace, as well as a dressing area with a lovely walk-in closet and a spacious primary bath. Three additional bedrooms and a bath complete the sleeping quarters. Outdoors, the grounds are just as considered as the interiors: an oversized heated gunite pool and spa, surrounded by extensive stone terracing, formal and English gardens, and manicured lawns. The detached three-car garage includes a heated guest, staff, or au pair suite with a full bath, offering flexible space for visitors, live-in help, or a private studio/office. Notable amenities include marble and granite finishes throughout, gleaming hardwood floors, and 9' and 12' ceilings. Every detail reflects a home that was built without compromise and maintained the same way. Zoned for the highly regarded Katonah-Lewisboro School District, including Meadow Pond Elementary School, John Jay Middle School, and John Jay High School, this is a rare offering for buyers seeking a full-time residence or a refined weekend retreat within easy reach of Manhattan.

295 Salem Road, Pound Ridge

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

5 Bedroom Homes for Sale in Westchester, NY

All 5 Bedroom Homes for Sale in Westchester, NY

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Tierra Stanback