5 Bedroom Homes for Sale in Westchester, NY

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

$3,825,000

5 Beds ⋅ 5 Baths ⋅ 987844 MLS

Priced to SELL! Five-plus private acres. A century-old Georgian. Towering trees, beautiful gardens, charming guest cottage and a pool within an hour of NYC! Historic without feeling precious. Private without feeling remote. Grand enough for a proper dinner party, relaxed enough for barefoot afternoons by the pool. • Exceptional early-20th-century Georgian architecture by Delano & Aldrich • High ceilings, great flow, French doors, fireplaces, and beautiful original details • Generous living and dining rooms for entertaining • Light-filled sunroom opening to a stone terrace and gardens • Inviting kitchen (6 burner Viking stove, Sub Zero fridge) + adjoining sitting room for everyday living • Primary suite with fireplace and sun-filled ensuite bath • Multiple bedrooms with fireplaces and garden views • Skylit third-floor artist’s studio + adjoining atelier • 5+ acres of privacy and peaceful natural surroundings, extra land available • Gated, tree-lined gravel drive • Specimen trees + curated perennial gardens • Lovely pool • Enchanting guest cottage • Greenhouse • Detached two-car garage. Chic Classic architecture. Modern country life. Room to make it yours.

328 McLain Street, Bedford Hills

$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

$2,995,000

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 an option to put in a heated gunite pool. 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

$3,500,000

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

$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

$1,125,000

5 Beds ⋅ 4 Baths ⋅ 980003 MLS

Location, Location, Location!!! Welcome to this tremendous all-brick 2-family home perfectly tucked away on a beautiful tree-lined street in the heart of McLean Heights. This sun-drenched home features a spacious 4-bedroom, 2.5-bath triplex that spans three floors of living space. The main level offers a grand living room, formal dining room with soaring ceilings, and multiple terraces perfect for relaxing outdoors. The primary suite includes its own private bath, and the third floor offers incredible versatility — ideal for a home office, family room, or fifth bedroom. The home retains its classic charm with original wood trim, bannisters, and gleaming hardwood floors throughout. The lower level hosts a legal 1-bedroom apartment with a living room, kitchen, bedroom, and bath — perfect for extended family or additional rental income. Rents at $2800 Outside, you’ll find a beautifully landscaped yard with lush greenery and a private patio oasis, perfect for friends. A commuter’s dream, this home is just blocks from Metro-North, buses, shopping centers, and only 25–30 minutes to Manhattan. Don’t miss this rare opportunity to own a timeless gem in one of Yonkers’ most desirable neighborhoods!

128 Parkway N, Yonkers

$2,599,000

5 Beds ⋅ 7 Baths ⋅ 976870 MLS

Step into a slice of Mediterranean paradise at 105 Cross Pond Road, where timeless elegance meets modern luxury. This breathtaking villa, inspired by classic European architecture, boasts over 6,000 square feet of refined living space on 5.+ meticulously landscaped acres. From the iconic red clay roof to the graceful stucco and stately arches, this property exudes sophistication at every turn. Key Features That Will Steal Your Heart: Mediterranean Charm: The distinctive architectural elements create an enchanting, old-world aesthetic. Expansive Interiors: Multiple fireplaces, private terraces, and oversized balconies invite seamless indoor-outdoor living. Private Waterfront Oasis: Your very own lagoon offers tranquil views, waterside relaxation, and kayaking adventures just steps away. Luxurious Finishes Throughout: Marble and natural stone details bring warmth and elegance to every room. Nature’s Playground: Over 5+ acres of pristine grounds, complete with a private island, provide endless opportunities for outdoor entertaining and peaceful solitude. Inside the Villa: From the moment you enter, the grand scale and thoughtful design captivate. Open-concept spaces flow effortlessly, perfect for everything from quiet evenings to hosting grand gatherings. Marble and stone finishes elevate the interiors, while fireplaces add cozy charm. Step outside onto expansive terraces and balconies to savor al fresco dining or watch the sunset over your serene property. The home also offers flexible spaces ideal for a chef’s kitchen, wine room, home gym, or a luxurious primary suite. Unbeatable Location for a Coveted Lifestyle: Nestled on prestigious Cross Pond Road in Pound Ridge, this estate combines privacy with accessibility. It’s part of the highly regarded Bedford Central School District and offers convenient access to I-684, Saw Mill Parkway, and Metro-North stations for an effortless commute to Manhattan. Nature lovers will adore the proximity to Ward Pound Ridge Reservation for hiking, camping, and fishing, while the charming nearby towns of Katonah, Bedford, and Stamford, CT, provide boutique shopping, fine dining, and cultural experiences. For wine enthusiasts, local vineyards and specialty shops await to help you curate the perfect collection. A Once-in-a-Lifetime Opportunity: 105 Cross Pond Road isn’t just a home—it’s an experience. Whether you’re savoring lakeside mornings, hosting elegant, or simply enjoying the serene beauty of your surroundings, this estate offers a lifestyle of unparalleled luxury and tranquility. Don’t miss your chance to make this extraordinary retreat your own.

105 Cross Pond Road, Pound Ridge

$949,000

5 Beds ⋅ 3 Baths ⋅ 940338 MLS

Legal three-family property in a convenient Peekskill location near downtown, restaurants, shopping, bus service and Metro-North. The property includes a spacious 3-bedroom apartment and two 1-bedroom apartments, currently generating $7,500 per month in rental income. An opportunity to live in one apartment and collect rent from the other two, or keep all three rented. Additional features include a three-car garage, off-street parking, a recently replaced roof and a large unfinished walk-up attic offering storage space. The seller is working with the City of Peekskill on an updated certificate of occupancy.

147 Union Avenue, Peekskill

$11,500,000

5 Beds ⋅ 7 Baths ⋅ 823682 MLS

Originally designed in 1925 by renowned architect Lewis Bowman, this extraordinary residence has been meticulously reimagined by Lucio DiLeo of Studio RAI Architects and its current owners through a comprehensive, four-year, world-class renovation. Seamlessly blending timeless architectural beauty with modern luxury, this nearly 9,200 SF masterpiece is defined by exquisite design, fine craftsmanship, and resort-style amenities. Set back along a private drive, the home’s stately facade gives way to a world of refined elegance. Stone steps wind toward an enchanting terrace and a glass-enclosed loggia, opening into interiors that are nothing short of breathtaking. A dramatic, balconied foyer overlooks a grand living room featuring a 14-foot soaring beamed ceiling, striking Palladian windows, and an imported 7x6-foot limestone fireplace, setting the tone for the extraordinary quality found throughout the home. The formal dining room, wrapped in silk-lined walls and centered around a second fireplace, is both luxurious and welcoming—ideal for elegant entertaining or intimate gatherings. Every inch of this residence reflects a deep commitment to artisanal detail and exceptional materials. At the heart of the home is a chef’s dream kitchen—bright and expansive, with a stunning barrel-arched ceiling and views of the rear gardens. A 12-foot island with a champagne sink, natural quartz countertops, and top-of-the-line appliances—including a La Cornue Grand Palais 180 range, La Cornue Flamberge rotisserie, Blue Star electric oven with pizza stone, Miele fridge and freezer, steam and speed oven, and separate coffee station—creates the ultimate culinary experience. A custom Vaclav brass and pewter hood, custom cabinetry by Nils Kasperson, a large pantry with an ice maker, a kitchen office, and a fully outfitted mudroom add both beauty and function. Flowing seamlessly from the kitchen, the spectacular Great Room is the home’s showpiece—anchored by a dramatic stone fireplace and enhanced by custom wood beams, a full built-in entertainment wet bar, bespoke built-in shelving, an 82-inch hidden drop-down TV, and state-of-the-art AV. Adjacent is a light-filled breakfast/dining room surrounded by Palladian windows that open to a private terrace with its own fireplace—perfect for al fresco dining and quiet evenings. Upstairs, five luxurious bedroom suites (easily convertible to six) each offer en-suite baths with steam showers, walk-in closets, AV systems, and custom built-ins. The primary suite is a serene retreat featuring a cathedral ceiling, private balcony, soundproof linen walls, a hidden 65-inch TV, and a lavish spa bath with radiant-heated floors, gas fireplace, soaking tub, and steam shower. Included in the 9,200 SF is 3,000 SF of upper- and lower-level, fully permitted space with infrastructure in place to build out a myriad of amenities such as a home gym, golf simulator, game room, home office, wine room, and more. The estate’s outdoor spaces are equally impressive, replete with endless stone walls and bluestone patios throughout. Designed for entertaining on a grand scale, the grounds feature a 42-foot heated pool and spa, a 70x60 sports court, multiple Lynx grill stations, expansive dining and lounge terraces, koi ponds, a secret garden with a swing, two cozy fireplace terraces, and ample space for a massive party tent. A fully automated Savant/Lutron lighting, AV control, and surveillance system ensures comfort and security in this private paradise. Completing the estate is a temperature-controlled, customized two-car garage with 11-foot ceilings outfitted for two auto lifts to accommodate two SUVs and two sports vehicles, plus additional driveway parking for eight vehicles—providing a total of 12 parking spaces. Set in a quiet, exclusive enclave just minutes from Bronxville village and a quick commute to Manhattan—all in a community celebrated for its top-rated schools and exceptional quality of life.

47 Masterton Road, Bronxville

$4,995,000

5 Beds ⋅ 6 Baths ⋅ 966535 MLS

Luxurious new construction in prestigious Ardsley Park! Located in the charming village of Dobbs Ferry, this prime home offers nearly 8,000 square feet of beautifully designed living space including a finished lower level. This exceptional, custom house features five spacious bedrooms, 5.5 baths, and a three-car garage, with time still available to personalize select finishes. Designed for modern living and effortless entertaining, the home also includes a stunning 20’ x 40’ swimming pool, creating a private backyard oasis. The chef’s kitchen is outfitted with premium appliances including a Sub-Zero refrigerator, Wolf range, and Bosch dishwasher, complemented by elegant quartz countertops and impeccable craftsmanship throughout. The spectacular primary suite offers a serene retreat with two, large walk-in closets and a luxurious spa-inspired bath with soaking tub, shower, double vanity, and quartz counters. Ideally located close to the Metro-North train station with a 36-minute commute to Grand Central Terminal, and within the highly regarded, award-winning Dobbs Ferry School District. A rare opportunity to enjoy sophisticated, new-construction living in one of Westchester’s most desirable Rivertown neighborhoods.

161 Sherman Avenue, Dobbs Ferry

5 Bedroom Homes for Sale in Westchester, NY

All 5 Bedroom Homes for Sale in Westchester, NY

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