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

$2,795,000

5 Beds ⋅ 5 Baths ⋅ 991143 MLS

This one-of-a-kind 5 bedroom, 5 full bathroom rustic California inspired residence on one of the toniest roads in Pound Ridge sits on 6.5 private acres, complete with a pool, tennis court and treehouse. Situated in a resort like setting, the home's exquisite indoor-outdoor flow and abundant natural materials, you'll feel worlds away, but is just 3 minutes from town and an hour from NYC. Once owned by Ted Sorenson, JFK's speechwriter, the unique estate is ideal as a year-round home, weekend retreat or secluded hideaway with Belgian block and chestnut floors, stone columns (the stone of which was excavated from the site), tongue-in-groove cedar walls, soaring beamed ceilings, 22 skylights and custom windows. Custom stair railings designed by renowned rustic artist, Daniel Mack. Enjoy lavish entertaining in impressive living spaces with floor-to-ceiling fireplace and windows. The rustic dining room seats 16, the masterful kitchen with original copper bar counter, accommodates gatherings of any size. Upper-level primary suite, main-floor two-bedroom suite, home gym, media room, sauna and office with custom desk made of one solid piece of hundreds of years old Baobab tree. The lower level en suite bunk room provides ample accommodations, with private entrance. Resort-like grounds and a bucolic location make this an exceptional country estate. Custom, high level properties like this don't come up very often.

217 Trinity Pass, Pound Ridge

$1,999,000

5 Beds ⋅ 5 Baths ⋅ 992869 MLS

OWNER WANTS THIS HOME SOLD>>PRICED DROPPED BY !100k!!!!!!! Welcome to 65 Wildway, a stunning residence set within one of Bronxville’s most coveted communities. This exceptional home is distinguished by its premier first-floor location, expansive layout, custom enhancements, and a beautifully landscaped private terrace—offering a rare blend of classic elegance and modern luxury. Thoughtfully upgraded throughout, the residence showcases spa-like renovated bathrooms, custom architectural millwork, designer wallpaper, and a seamless mix of new flooring and plush wall-to-wall carpeting. Generously sized bedrooms, oversized windows, walk-in closets, and abundant storage create a refined yet comfortable living experience. Notable upgrades include 6” select white oak flooring, central air conditioning and heating across all three levels, and a fully renovated kitchen featuring exquisite Calacatta stone surfaces and a matching statement fireplace. Elegant Italian-style handrails further enhance the home’s sophisticated design. The lower level offers a spacious and versatile bonus room—ideal for entertaining or a private retreat— Step outside to a luxurious stone patio surrounded by a natural rock wall, creating a private outdoor oasis perfect for gatherings or relaxing. The added structure complete with a Mitsubishi split system for heating and cooling, a dedicated 60-amp service panel, mounted TV, and Gamco double door, offers outside leaving at his best The chef’s kitchen is equipped with premium stainless-steel appliances, multiple ovens, and a separate, comfortable dining area. The living room is filled with natural light and features custom built-in cabinetry and designer blinds. A spacious two-car garage adds convenience, while the home’s prime location places you just moments from Bronxville’s Metro-North station, along with the Village’s charming shops and restaurants. 65 Wildway offers the perfect balance of luxury living and everyday comfort—an ideal place to call home. Schedule your private showing today before this exceptional property is gone.

65 Wildway, Bronxville

$4,125,000

5 Beds ⋅ 5 Baths ⋅ 987844 MLS

Refined and timeless, this gracious residence has been meticulously preserved and maintained for over a century. Approached by a gated, tree-lined gravel drive, the house is a distinguished example of early 20th-century Georgian architecture, offering exceptional privacy and a profound sense of tranquility. Set on over five acres in the heart of Bedford Hills, surrounded by majestic specimen trees and beautifully curated perennial gardens, the property embodies the essence of a classic country estate. Amenities include a heated pool, an enchanting guest cottage, a greenhouse, a caretaker’s residence, a detached two-car garage, and dedicated maintenance buildings. Inside, the house reflects the signature elegance and proportion associated with Delano & Aldrich; high ceilings, expansive openings between principal rooms, and refined architectural detailing create a seamless flow for both formal entertaining and relaxed living. Fireplaces anchor the generously scaled living and dining rooms, while framed-glass French doors open to a grand sunroom. This light-filled space extends to a stone terrace overlooking the gardens—ideal for summer gatherings or sunlit winter afternoons. The kitchen, complemented by an adjoining sitting room, offers an inviting setting for intimate meals and everyday living. Upstairs, the primary suite provides a serene retreat, complete with its own fireplace and a luxurious ensuite bath designed for quiet indulgence. A former sleeping porch has been thoughtfully reimagined as a charming playroom with adjoining guest quarters, accompanied by an additional spacious bedroom and hall bath. Each bedroom features its own distinctive fireplace and enjoys picturesque garden views through large casement windows. The third floor offers two substantial bedrooms, a classic bath, and a skylit artist’s studio filled with natural light, along with an adjoining atelier and generous storage. More land available.

328 McLain Street, Bedford Hills

$5,500,000

5 Beds ⋅ 8 Baths ⋅ 922795 MLS

A new build echoing the great modern masters, Haines House spans across nearly six pristine Bedford acres. While its spirit evokes the harmony often associated with Frank Lloyd Wright, its identity is rooted in the modernist vision of his contemporary, Frank Dushin. This turnkey estate includes walls of glass wrapped in warm cedar, sculptural rooflines tracing the hillside, and natural bluestone. Within the main residence, the great room opens as a sweeping expanse of glass anchored by a central fireplace. A glass enclosed elevator glides from the garage to the primary suite, reaching every level and framing the estate at each stop. The suite crowns the top floor with dual baths, a sitting room, an office, and private terraces set among the treetops. The additional bedroom suites unfold as retreats of their own. The separate guest pavilion, a light-filled structure of two suites joined by a luminous glass corridor, forms a second residence. Together the two living spaces are generous and flexible for both residents and guests, including studio spaces for creative work. Internal garages include a rare drive through bay, and there is expansive guest parking. Beyond the residences, newly relandscaped grounds unfold in broad, level gardens and lawns rolling to a tranquil pond, a shimmering saltwater pool, and a sports court. Wide open and gently sculpted, the grounds invite play, gathering, and quiet exploration alike, a private world to roam from morning to evening. Enveloped in its own green canopy, the estate offers rare privacy and security. A newly installed three zone high velocity cooling/heating system, with additional underfloor heating ensures comfort year-round. Turnkey and unique, Haines House sits minutes from Bedford Village and within easy reach of Manhattan.

496 Haines Road, Bedford Corners

$2,995,000

5 Beds ⋅ 7 Baths ⋅ 986239 MLS

There are homes… and then there are places that feel quietly set apart from the world around them. Tucked behind a gentle approach, on nearly four private acres in the heart of Briarcliff Manor, 36 Revolutionary Road reveals itself slowly, intentionally… like a secret meant only for those who understand what true luxury feels like. This is not just a home. This is a legacy estate. Set perfectly between the Hudson River and Sleepy Hollow Country Club, the location offers the rare balance today’s buyers search for privacy, proximity, and prestige. Minutes to Metro North, fine dining, boutique shopping, and everything that defines Westchester luxury living… yet once you arrive, the outside world seems to soften. There is a stillness here. You feel it walking the grounds, where mature trees frame rolling lawns and sunlight filters through in that unmistakable golden way. There is a rhythm to the property… the kind that invites long mornings on the porch, quiet afternoons by the pool, and evenings that stretch just a little longer than planned. And somewhere within it all… life quietly thrives. Bees drift from bloom to bloom, tending to the landscape in a way that feels both timeless and grounding… a subtle reminder that this estate is not just maintained, it is alive. Inside, the home unfolds with a level of craftsmanship and scale rarely seen today. Five ensuite bedrooms offer both privacy and comfort, anchored by a truly exceptional primary suite with its own fireplace, spa like bath, expansive dressing room, and a private sleeping porch… a nod to a more romantic era of living, where fresh air and slow mornings were part of everyday life. The kitchen is designed not just for cooking, but for gathering… a chef’s workspace complemented by a generous butler’s pantry, ideal for seamless entertaining. It flows effortlessly into a formal dining room that feels pulled from the pages of a design magazine, where hand printed Zuber wallpaper and a fireplace create a setting that is both refined and deeply inviting. Every room tells a story. A wood paneled office with its own fireplace opens to the front porch, offering a work from home experience that feels anything but ordinary. The living room, wrapped in double walls of French doors, blurs the line between indoors and out, filling the space with natural light throughout the day. Nearby, the sunroom becomes its own retreat… a place to pause, unwind, and simply take in the beauty of the property. Step outside, and the estate continues to reveal itself. A gunite pool set within manicured grounds. Multiple porches designed for every mood and moment. A historic Lord and Burnham greenhouse… a rare and remarkable feature that speaks to the property’s heritage. And a four plus car garage with a private apartment above, offering flexibility for guests, extended stays, or staff. This is Westchester luxury real estate at its finest, where historic architecture meets modern lifestyle, where privacy meets convenience, and where every detail has been thoughtfully considered. Because the truth is… You can always renovate a home. But you cannot recreate land like this. You cannot replicate this setting. And you cannot manufacture the feeling this property gives you the moment you arrive. 36 Revolutionary Road is not just being listed. It is being offered.

36 Revolutionary Road, Briarcliff Manor

$2,375,000

5 Beds ⋅ 3 Baths ⋅ 980144 MLS

WILLOW FARM. Pristine Pre-Revolutionary Farmhouse. A Barrett Family homestead dating to 1750. Expanded in the 1930’s, with the addition of a handsome stone wing. Interior spaces replete with original details -- spectacular wide-plank floors, vintage millwork, built-in cupboards, windows salvaged from the old Katonah Library and three fireplaces. Beautifully proportioned Living Room with fireplace, ceiling beams, plaster walls and antique bow window. Formal Dining Room with American Chestnut floor. Beautifully renovated Kitchen with custom cabinetry, marble counters and high-end appliances. Breakfast Area with spectacular antique window. Family Room with fireplace and pond view. Choice of Offices for working remotely. Private Primary Suite with exposed beams, fireplace, Dressing Room and Bath. Two additional Bedrooms. Renovated Hall Bath. Located on a quiet country road, six bucolic acres with gorgeous open property, spectacular plantings and gardens and two scenic ponds. Private Swimming Pool. Separate Guest Cottage. Detached Garage with Guest/Office Suite. Two Antique Storage Barns. Conveniently close to the village of Katonah, the Metro North train and commuting arteries. A fabulous country retreat and truly special offering!

95 Croton Lake Road, Katonah

$3,500,000

5 Beds ⋅ 6 Baths ⋅ 984817 MLS

Two homes, one gorgeous estate. This exceptional property features two distinct residences—a stunning modern new-construction main home and a charming, fully renovated 2 bedroom cottage—situated together on a picturesque, private estate. Modern and European-inspired, this residence balances scale with sophistication. Thoughtfully crafted to blend clean architectural lines with warm, natural materials, the home features 10-foot ceilings on the main level, a dramatic 12-foot great room, and vaulted ceilings on the second floor that create an airy, light-filled atmosphere throughout. The interior is finished with wide-plank walnut floors, custom millwork, and a curated mix of shiplap and reclaimed beams, lending richness and character at every turn. The kitchen serves as the heart of the home, featuring refined white cabinetry, quartz countertops, an expansive center island. The primary suite is a private retreat with a spa-like ensuite and walk-in closet, while each additional bath is appointed with heated floors and custom finishes. An unfinished, above-grade lower level with nine-foot ceilings provides 1,500 square feet of potential for future expansion, accompanied by a separate 800-square-foot bonus space perfect for an office, studio, or recreation room. Completing the estate is a delightful, fully renovated 861 square foot, two-bedroom cottage with its own 2 car garage. Offering total independence, it serves as the ideal setup for guests, extended family, or a dedicated home office, adding incredible versatility to the property. Exterior details are equally compelling, featuring Hardie siding, a striking engineered slate roof, and oversized European windows. The grounds are designed for leisure, with bluestone patios, professional landscaping, a full irrigation system, and a heated gunite pool framed by stonework. A semi-circular pergola with open beams serves as a unique architectural focal point, perfectly positioned to enjoy the exterior side of the home’s double-sided fireplace—the ideal setting for intimate evenings and effortless entertaining. Located just minutes from top-rated schools, local shopping, and outdoor gems like Bedford Village Memorial Park and the Ward Pound Ridge Reservation, this estate offers the perfect balance of privacy, luxury, and convenience. Total (taxable living area) square footage includes the cottage square footage.

515 Long Ridge Road, Bedford

$3,995,000

5 Beds ⋅ 6 Baths ⋅ 823299 MLS

Behind private gates, nearly six acres of bucolic countryside unfold around a spring-fed lake — a setting that feels worlds away, yet sits just one hour from Manhattan. Gut-renovated to the studs and reimagined from the ground up, this Pound Ridge estate blends Mid-Century Modern design with original stone construction and hand-hewn beams — a rare marriage of architectural integrity and contemporary refinement. The result is a home that feels both timeless and entirely of the moment. The main residence offers four bedrooms and has sweeping water views that define the property. A detached guest studio with two-car garage provides flexible accommodation for visitors or staff, while the heated gunite pool and pool house — complete with full bath, wet bar, and huge fireplace — create an effortless setting for both quiet evenings and elevated entertaining. An additional detached two car garage rounds out the offering. Outside, the grounds have been as thoughtfully curated as the interiors: new landscaping, artisan stonework, full irrigation system, patios, and mature tree work frame the lake and connect seamlessly to the Pound Ridge Land Conservancy — a permanent buffer that ensures the privacy and natural beauty of this property endure. Canoe and Kayak directly from the property! Truly turnkey. Completely one-of-a-kind.

39 Old Snake Hill Road, Pound Ridge

$998,000

5 Beds ⋅ 6 Baths ⋅ 984886 MLS

Auction Pricing. All qualified bids over asking will be considered, Tucked away in the picturesque village of Dobbs Ferry, this expansive residence effortlessly combines comfort, flexibility, and timeless appeal. Encompassing more than 3,700 sq ft on nearly one private acre, this property is a rare opportunity to create your forever home in one of Westchester’s most sought-after Rivertowns. Inside, you’ll find five spacious bedrooms, five full baths, and a convenient main-level powder room, offering an ideal layout for large households and those who love to entertain. The generous floor plan provides a seamless flow between living, dining, and lounging spaces, perfect for both everyday living and memorable gatherings. A versatile lower level invites endless possibilities: imagine a recreation room, home gym, studio, or private guest suite, the choice is yours. The oversized driveway easily accommodates multiple vehicles, making hosting effortless. With its generous proportions, solid bones, and limitless potential for customization, this home invites you to bring your vision to life. Set just minutes from downtown Dobbs Ferry, residents enjoy access to award-winning schools, Metro-North service to Manhattan, charming shops, vibrant dining, and the scenic Hudson River parks that define Rivertown living. Discover the space to grow and the freedom to dream, schedule your private showing today.

5 Forkland Lane, Dobbs Ferry

$1,100,000

5 Beds ⋅ 3 Baths ⋅ 981518 MLS

Back and better than ever! During its brief time off the market, the seller completed valuable improvements, including a brand-new roof over the balcony/deck and attached garage, along with beautifully refinished and updated flooring in the living and dining rooms, making this exceptional Colonial even more appealing. Rich in character and timeless charm, this spacious home sits on a picturesque corner lot directly across from James M. Carroll Park. The main residence offers 5 bedrooms and 3 full baths, while a thoughtfully designed addition includes a two-car garage and a versatile mother/daughter or au pair suite complete with a bedroom, summer kitchen, living area, and private entrance—ideal for extended family, guests, or multigenerational living. Enjoy summer concerts from your second-floor balcony overlooking the park or relax in the screened gazebo surrounded by mature landscaping, privacy-enhancing trees, and a fully fenced backyard with plenty of room for recreation or a future in-ground pool. Multiple outdoor entertaining spaces include an upper balcony/deck with park views and a lower-level deck for family gatherings. Inside, you'll appreciate the home's historic craftsmanship, highlighted by impressive two-foot-thick stone walls, a stunning stone fireplace, a spacious family room, and a large attic offering exceptional storage or future expansion potential. Additional features include a new roof over the balcony/deck and garage, a 15-year-old architectural roof on the main home, 200-amp electrical service with generator hookup, an oversized driveway, and a freshly painted exterior. Convenient sidewalks in both directions provide easy access to shopping, parks, and everyday amenities, while the home's location on a bus route offers added convenience. A rare opportunity to own a home that combines historic character, modern updates, flexible living space, and an unbeatable location.

7 Rolling Hills Road, Thornwood

$749,000

5 Beds ⋅ 2 Baths ⋅ 975998 MLS

Welcome home! 31 Kipling Street is a lovely 5-bedroom, 2-bath, split-level home, set on a quiet street in the sought-after Poets’ Corner neighborhood of Hartsdale, known for its established homes, and convenient access to transportation and everyday amenities. This well-placed spacious home features an ideal setup for visiting guests. The recently updated eat in kitchen has an island and is open to the dining/living room with hardwood flooring and soaring ceilings with a mid-century style windows, allowing for sundrenched rooms. The lower level has been freshly painted!

31 Kipling Street, Hartsdale

$3,498,000

5 Beds ⋅ 6 Baths ⋅ 956150 MLS

Experience refined new construction living at 50 Austin Place, a thoughtfully designed to-be-built 2026 Colonial estate set on 11.22 private acres in the heart of Briarcliff Manor. Offering 5,775 square feet of elevated living space, this 5-bedroom, 5.5-bath residence seamlessly blends timeless architecture with modern functionality. Estimated completion Winter 2026. A dramatic double-height foyer sets the tone upon entry, complemented by custom millwork, oversized windows, and 7-inch white oak flooring that extends throughout the home. The main level features 9-foot ceilings and a seamless, open flow designed for both everyday living and elevated entertaining. Anchoring the home is a chef’s kitchen outfitted with premium GE Monogram appliances, quartz countertops, custom cabinetry, an oversized island with seating for five, a butler’s pantry, and a fully equipped wet bar with beverage and wine refrigeration. The upper level offers 8-foot ceilings and well-appointed bedrooms, including a luxurious primary suite designed as a true retreat. Highlights include tray ceilings, dual walk-in closets, and a spa-inspired bath featuring a soaking tub, glass-enclosed shower, double vanity, and designer finishes with porcelain and marble tile throughout. Each additional bedroom is complemented by its own en-suite bathroom with custom vanities, walk-in closets and high-end finishes. The lower level features 10-foot ceilings and a walk-out design, providing exceptional flexibility for future living space. A 3-car attached garage offers ample storage and convenience. Set far back from the road, a long private driveway leads to this secluded, wooded estate setting, offering unmatched privacy and tranquility. The expansive 11.22-acre property is site-approved for a pool and presents endless possibilities for outdoor living and recreation. Built with energy efficiency in mind, the home includes multi-zone HVAC, high-end windows, and spray foam insulation, delivering both comfort and long-term value. A rare opportunity to own new construction with scale, privacy, and craftsmanship in one of Briarcliff Manor’s most sought-after locations.

50 Austin Place, Briarcliff Manor

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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.