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

$999,000

5 Beds ⋅ 2 Baths ⋅ 1036297 MLS

Welcome to this beautifully maintained 5-bedroom, 2-bath home situated on approximately 0.40 acres in desirable Greenburgh. This inviting home features a spacious living room with a stunning brick fireplace, generously sized bedrooms, and a versatile floor plan designed for comfortable living and entertaining. The walk-out lower level offers excellent potential for an in-law suite, guest quarters, home office, or recreation space. Enjoy outdoor living on the split-level deck overlooking the spacious yard. Additional highlights include a large 2-car garage, wraparound driveway, and convenient access to major highways, shopping, and dining.

24 Old Knollwood Road, White Plains

$3,300,000

5 Beds ⋅ 6 Baths ⋅ 1036005 MLS

Nestled in the heart of Rye's coveted Greenhaven waterfront community, with DEEDED RIGHTS TO THE PRIVATE BEACH AND PIER located just steps away - at the end of the street, minutes from Greenwich, this exceptional 5-bedroom, 5.1 bathroom residence offers an extraordinary opportunity to enjoy luxury living in one of Westchester County's most prestigious neighborhoods. Situated on an expansive half acre lot, this lovingly maintained home boasts 3,804 square feet of beautifully designed living space, which does not include the lower level offering an additional 1300 sq ft of endless potential possibilities for recreation, a home gym, media room, guest quarters, or multigenerational living. Built in 1988, the home showcases a timeless brick colonial design with spacious, light-filled rooms, gracious entertaining spaces, and a seamless flow ideal for both everyday living and elegant gatherings. The generous floor plan offers oversized bedrooms, multiple living and entertaining areas with fireplaces. Outside, the level landscaped grounds create a private retreat with plenty of room for outdoor entertaining, or the addition of a pool. Set on over half an acre in the sought-after Greenhaven neighborhood, you'll enjoy a serene residential setting and moments from Milton Harbor, marinas, parks, beaches, and scenic waterfront walks. Residents appreciate Greenhaven's unique waterfront lifestyle while remaining just minutes from downtown Rye's vibrant restaurants, boutique shopping, Metro-North station, award-winning schools, and major highways, providing an effortless commute to Manhattan. House has been updated with new forced air heating system/central air and new H/W heater.

90 Greenhaven Road, Rye

$649,900

5 Beds ⋅ 2 Baths ⋅ 1036746 MLS

Welcome to 312 Bay Street in Peekskill! This beautifully renovated five-bedroom, three-bath single-family home offers generous living space, character, and an unbeatable commuter-friendly location. Renovated just a few years ago, the home features an inviting enclosed front porch, custom woodwork surrounding the doors and windows, and five generously sized bedrooms with plenty of room for today’s lifestyle. Located approximately a five-minute walk from the Peekskill Metro-North Hudson Line station, enjoy convenient access to New York City in about an hour. Close to major highways, shopping, dining, parks, and all that downtown Peekskill has to offer. A rare combination of space, updates, character, and accessibility—move in and make it yours!

312 Bay Street, Peekskill

$3,495,000

5 Beds ⋅ 6 Baths ⋅ 1035090 MLS

Designed by Vuko Tashkovich, one of Westchester's defining modernist architects, this home is privately sited on over 3 acres, offering 7,500+ square feet across three finished levels. Artfully refined while retaining the character of its original design, the home is defined by long horizontal lines, cylindrical forms, clerestory windows and walls of glass that connect the interiors to the surrounding landscape. A gallery-like entry introduces expansive, light-filled rooms with built-ins, tile work and exquisitely restored herringbone floors. The spacious living room is anchored by a stone fireplace, custom bookcase wall, and wet bar, with an adjoining sitting area that opens onto the broad outdoor terrace. The dining room with floor-to-ceiling windows and kitchen with attached breakfast room overlook the lush grounds, specimen trees and newly poured gunite pool with spa. Four bedrooms on the upper level include a spacious primary suite with fireplace, bath and private terrace. Additionally, the ease of single-level living is available with a desirable first-floor primary suite option. The finished lower level adds a newly completed gym, full bath and flexible recreation or office space. This private modernist retreat combines architectural character with modern livability. 50 miles to NYC.

10 Dogwood Hills Road, Pound Ridge

$1,250,000

5 Beds ⋅ 4 Baths ⋅ 1034206 MLS

A once-in-a-lifetime opportunity to own Maplehurst Farm, originally known as the Conklin-Chadeayne Farmhouse, an irreplaceable Antique Farmhouse Colonial estate dating back to the 1730s, nestled on five irreplaceable acres in the highly sought-after community of New Castle. Rich in history and timeless character, this extraordinary property preserves many of its original architectural details, including wide-plank pine floors, original farm doors, hand-crafted millwork, and three fireplaces. Offering exceptional versatility, the estate is ideally suited as a private country retreat, equestrian property, or multi-generational residence. Set on over five picturesque acres, the grounds are a true sanctuary. Enjoy peaceful mornings on the multi-level stone patios surrounded by mature landscaping and native plantings, or gather with family and friends on the expansive covered front porch. Equestrian enthusiasts will appreciate the six-stall horse barn, multiple paddocks, and riding arena, while the heated 20' x 50' in-ground pool, complete with its own stone patio and custom-built pergola, provides the perfect setting for summer relaxation. Historic stone walls, crafted from stones found on the property, and impressive steps built from reclaimed West Point stone further showcase the estate's remarkable heritage. A gracious front porch welcomes you into the center hall. The main level features a living room with a wood-burning fireplace, an intimate reading room, formal dining room, eat-in kitchen with its own fireplace, powder room, family room, laundry room, and walk-in pantry. The second level features a spacious primary suite, three additional bedrooms, and a full bath highlighted by a timeless clawfoot tub. The approximately 1,200-square-foot finished walk-out lower level offers exceptional flexibility, featuring a spacious living and dining area with wide-plank flooring, a former tiled summer kitchen, two bedrooms with hardwood flooring—one with a fireplace—a storage/mechanical room, and multiple exterior entrances, creating an ideal space for extended family, guests, or a potential mother/daughter arrangement with the appropriate approvals. While this private estate feels like a world away, it is just minutes from the Village of Ossining, the scenic Hudson River waterfront, and an array of restaurants, shops, parks, hiking trails, and recreational activities that make the Hudson Valley such a sought-after destination. Located approximately 45 minutes from New York City, this extraordinary estate presents a rare opportunity to own an authentic piece of American history while enjoying the privacy, beauty, and lifestyle of a truly exceptional country property. Estates of this significance, craftsmanship, and versatility are exceedingly rare and simply cannot be replicated.

15 Inningwood Road, Ossining

$1,150,000

5 Beds ⋅ 4 Baths ⋅ 1027260 MLS

WELCOME HOME! Ideally situated in one of Hastings-on-Hudson's most desirable locations, this spacious home is tucked away on a peaceful TRUE cul-de-sac lot, and Set on a generous 17,800-square-foot lot, a RARE find for this area, this property offers privacy, tranquility, and exceptional outdoor space.. A welcoming foyer opens to a bright, expansive living room that flows seamlessly into the spacious dining room—an inviting setting for everyday living, holiday celebrations, and entertaining. The thoughtfully positioned kitchen provides excellent workspace and easy access to the rest of the home. Just beyond, a large mudroom with laundry and direct backyard access adds everyday convenience. A centrally located full bathroom serves the main living areas and bedroom wing, featuring a comfortable family room and two generously sized bedrooms—ideal for guests or convenient first-floor living. Upstairs, a central hallway connects three well-proportioned bedrooms and two full bathrooms. The spacious primary bedroom offers a private bath, while the two additional bedrooms share a conveniently located full bathroom, creating a peaceful retreat away from the home's main gathering spaces. The versatile lower level features a private entrance, direct access to the attached two-car garage, two additional bedrooms, a full bathroom, a separate laundry room, and a mechanical room—offering excellent flexibility for guests, extended family, home offices, or recreational space. With its spacious and adaptable layout, desirable setting, and expansive property, this home offers an exceptional combination of comfort, privacy, and convenience.

14 Glenn Place, Hastings-On-Hudson

$699,999

5 Beds ⋅ 2 Baths ⋅ 1034494 MLS

Welcome to 462 S 3rd Avenue. Located in the South Side of Mount Vernon, this legal 2 family house offers a three bedroom, one bath unit over a 2 bed, one bath unit on the first floor. In addition, the basement offers a finished one bedroom, one bath unit with a separate entrance. Generous backyard and your own private driveway allows for comfort and convenience. Located close to the MetroNorth as well as the Bronx River and Cross County Parkways, I87 and I95 Expressways. Great opportunity for owner to live in one unit and rent out the other unit(s). Request a showing today.

462 S 3rd Avenue, Mount Vernon

$1,199,000

5 Beds ⋅ 4 Baths ⋅ 1034249 MLS

Distinguished Victorian residence located in New Rochelle's Historic District offering ample living space on a beautifully landscaped 0.36 - acre property. Rich in architectural detail and timeless craftsmanship, this home features a welcoming wraparound porch, soaring ceilings, original hardwood floors, detailed millwork, oversized windows, and generously proportioned rooms throughout. The spacious floor plan includes multiple living and entertaining areas, a formal dining room, a well-equipped kitchen with ample cabinetry and workspace, spacious bedrooms, multiple bathrooms, and abundant natural light throughout. The home's classic character, flexible layout, and impressive scale provide exceptional opportunities to enjoy as-is or personalize over time. Outdoor features include expansive grounds, mature landscaping, a detached garage, and an extended driveway, providing ample space for outdoor enjoyment, entertaining, gardening, or recreation. Conveniently located near parks, shopping, dining, Metro-North, major parkways, and other local amenities, this is a rare opportunity to own a historic home offering exceptional character, generous living space, and an outstanding setting.

29 The Boulevard, New Rochelle

$825,000

5 Beds ⋅ 2 Baths ⋅ 1021512 MLS

EXCELLENT OPPORTUNITY for today's buyers, come to see this spacious 5 bedroom, 2 full-bath home and discover the value it offers!. Now offered at $825,000, this home presents an excellent opportunity for buyers looking for space, comfort, and exceptional value in today's market. A fresh market position makes this exceptional 5 bedroom home an even more versatile to accommodate a variety of lifestyles. Feel a peaceful atmosphere stepping outside to a spacious back yard, perfect for relaxing. Schedule your private showing and discovery the value for yourself. Your dream home is awaiting your personal touch to enjoy in comfort, elegance and convenience. YOU MUST SEE IT TO APPRECIATE IT.

3 Greenwood Lane, White Plains

$1,250,000

5 Beds ⋅ 5 Baths ⋅ 1032285 MLS

Discover a truly one-of-a-kind brick-and-stone Cape Cod home offering beautifully reimagined living space across three expansive levels. Combining timeless architectural charm with modern finishes, this one-of-a-kind home features five bedrooms, multiple bonus living areas, and an incredibly versatile floor plan designed to adapt to your lifestyle. Beautifully renovated throughout with a new roof, distinctive architectural character, exceptional living space, and remarkable flexibility, this is a home that simply cannot be appreciated from photos alone. Whether you're looking for room to grow, space for extended family, multiple work-from-home options, or a home that evolves with your lifestyle, 6 Truman Avenue delivers a rare combination of comfort, character, and endless possibilities. The main level welcomes you with a bright, open-concept floor plan that seamlessly connects the family room, dining area, and chef's kitchen—ideal for both everyday living and entertaining. This floor also features two generously sized bedrooms, a versatile den or home office, and two beautifully renovated full bathrooms. The upper level offers two additional bedrooms, a spacious bonus room perfect for a playroom, studio, or media room, a full hall bathroom, and abundant storage space. The backyard is spacious enough for multiple zones and seating areas including dining, playground, your new edible garden, and fire pit. The attached two-car garage and driveway entrance provide outstanding convenience and flexibility. The heart of the home is an impressive chef's kitchen featuring soaring vaulted ceilings with exposed beams and a skylight. The elegant quartz countertops and a seamless quartz backsplash create an exceptional workspace for cooking and entertaining. There's ample counter space for meal prep and serving guests at the kitchen island. Two sinks and plenty of cabinet storage add to the functionality. The stainless-steel appliance suite features a gas range, wall oven, and sleek refrigerator. Off of the kitchen is your oversized balcony overlooking the backyard. The formal living room showcases a stunning cement fireplace harkening a European villa and pocket doors for added privacy when you need some quiet time. The den/home office is just the beginning of bonus spaces for a house that goes on and on. The first hall bath features a shower and floating toilet. The principal bedroom has two closets and a sunroom fitted with a laundry hook-up for ultimate convenience. The spacious second bedroom houses a walk-in closet. The second full bathroom on the first floor features a zero entry shower, floating vanity, and another tankless toilet. On the second story we have two additional bedrooms, a bonus room, and storage. The hall bathroom on the second floor has a tub and beautiful micro-cement finish for a timeless and elevated look. The walk-out lower level presents an expansive area with endless potential for all to spread out. Whether movie room, home gym, guest suite, and/or additional living space. Laundry and utility areas are also located on this level. New pellet boiler is highly energy efficient. Outside, the backyard offers endless possibilities for entertaining, outdoor dining, gardening, play areas, or relaxing around a future fire pit. Combining exceptional size, extensive renovations, distinctive architectural character, and remarkable versatility, this home is unlike anything else currently on the market. Whether you're seeking generous living space, room to entertain, or the opportunity to further customize the expansive lower level, this property delivers.

6 Truman Avenue, Yonkers

$682,500

5 Beds ⋅ 3 Baths ⋅ 1031355 MLS

From the moment you arrive, the home’s classic architectural presence and inviting layout offer endless possibilities. Inside, you’ll find spacious sun-filled rooms, high ceilings, and the perfect canvas to restore and customize a true vintage gem to your personal style. The private backyard provides space for entertaining, gardening, or simply enjoying peaceful outdoor living. Ideally located near schools, parks, shopping, transportation, and vibrant downtown New Rochelle, this property combines historic charm with everyday convenience. Whether you’re searching for a forever home or a unique restoration opportunity, 196 Elm Street is filled with potential and ready for its next chapter. Quick 45 Minute Ride to Manhattan on Metro North.

196 Elm Street, New Rochelle

$1,495,000

5 Beds ⋅ 5 Baths ⋅ 1022836 MLS

Welcome to Arrowcrest Estates at Hunterbrook, a premier Yorktown Heights enclave where elegance, privacy, and effortless living come together. Privately set on 3.67 beautifully manicured acres, this exceptional 5,715-square-foot custom home, built by respected local builder Wilder Balter Development, offers timeless craftsmanship and thoughtful design throughout. Sun-filled interiors, rich hardwood floors, and architecturally striking windows create an inviting backdrop from the moment you enter. At the heart of the home is an impressive chef’s kitchen featuring custom cherry cabinetry, a six-burner range with grill, dedicated wine refrigerator, oversized center island with vegetable sink, and a bright breakfast room perfectly suited for casual mornings and everyday gatherings. The kitchen flows seamlessly into the sunken great room, where a cozy fireplace and custom built-ins create a warm and sophisticated gathering space. A spacious formal dining room provides ample room for entertaining, while the elegant living room, complete with its own fireplace, offers a more intimate setting. A convenient first-floor den provides the perfect space for a home office, study, or quiet retreat. Upstairs, the thoughtfully designed floor plan continues to offer comfort and flexibility. Privately positioned away from the additional bedrooms, the expansive primary suite is a true sanctuary, featuring a tray ceiling, spa-like bath, and generous closet space. Additional accommodations include a bedroom with its own en-suite bath, two bedrooms connected by a Jack-and-Jill bath, and a spacious bonus room ready to adapt to your lifestyle—whether as a media room, playroom, gym, or additional office. Everyday functionality is equally well considered, with a spacious and well-organized mudroom and laundry area conveniently located just off the garage entry. The finished walk-out lower level expands the living space even further, offering a generous recreation/game room, full bath, and abundant room for entertaining and play, along with a large unfinished area providing excellent storage. Outdoor living is just as inviting. The expansive deck overlooks a private, wooded backdrop and level yard, creating a peaceful setting for summer gatherings, dining al fresco, or simply enjoying the serenity of the property. An inviting front porch adds another charming outdoor retreat and is sure to become a favorite spot for relaxing throughout the seasons. Meticulously maintained by its long-time owners, this exceptional estate offers a rare combination of privacy, polished craftsmanship, generous living spaces, and a truly comfortable lifestyle. Ideally located in the Huntersville area of Yorktown Heights, the property is conveniently close to shopping, schools, the Taconic State Parkway, and Metro-North—providing the perfect balance of tranquility and accessibility.

1985 Hunterbrook Road, Yorktown Heights

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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