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

$799,000

5 Beds ⋅ 3 Baths ⋅ 982256 MLS

Calling all contractors! do not miss out on this two and a half story, 2 family home. Close proximity to the Wilson Wood Pool and Park. Close to public transportion. Close to schools.

129 Hillside Avenue, Mount Vernon

$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

$1,150,000

5 Beds ⋅ 3 Baths ⋅ 979152 MLS

Discover the potential at 18 Devon—an opportunity to create the home you’ve been envisioning in the highly sought-after Lawrence Park West. This charming, walkable neighborhood offers the perfect balance of suburban tranquility and easy access to the city, along with nearby shopping, dining, and entertainment. The home features a flexible and spacious layout with three generously sized bedrooms on the main level and two additional bedrooms in the attic—ideal for a growing household or anyone seeking extra space. Two full bathrooms are conveniently located on the first floor, with a half bath in the basement. The lower level provides versatile bonus space perfect for a home office, recreation area, gym, or media room, along with a dedicated laundry area. Set on lovely grounds, this property is ready for your personal touch. If you’re searching for space, layout, and location—and don’t mind adding your own updates—this is an exceptional opportunity. Schedule your private showing today and imagine the possibilities! Subject to third Party approval!

18 Devon Road, Bronxville

$1,095,000

5 Beds ⋅ 3 Baths ⋅ 977120 MLS

This distinctive Teatown compound made for gatherings and entertainment blends timeless craftsmanship with modern livability offering seclusion without sacrificing proximity to trains, parks, and major highways. Tucked at the end of a quiet cul-de-sac, this exceptional estate offers rare privacy on more than 3 picturesque acres while remaining conveniently close to everything. The stunning grounds showcase a harmonious mix of wooded areas, meandering walking trails, expansive lawns, curated gardens, and beautiful stonework, all connected by a thoughtful network of driveways, pathways, and steps. Multiple terraces, patios, and outdoor seating areas are perfectly positioned across the property to capture its remarkable natural surroundings. The thoughtfully designed Main house layout features an expansive family room with wood-burning fireplace perfect for everyday gathering, first-floor bedroom with a full en-suite bath, ideal for guests, along with a dedicated laundry room. The main floor features walls of windows showcasing the sylvan setting and a formal dining room that flows seamlessly into a spacious living room. The eat-in kitchen, complete with a charming breakfast nook, is easily accessible and well-suited for casual dining. This level also includes three additional bedrooms, including one with a private en-suite bath, two bedrooms share a well-appointed hall bath, and a laundry room. The Detached 3 car garage with guest quarters and guest patio with built-in wood grill and woodland views add to this retreat.

27 Allapartus Circle, Ossining

$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

$2,199,999

5 Beds ⋅ 5 Baths ⋅ 970202 MLS

Legal three-family home in prime Eastchester location, completely rebuilt from the ground up with brand new poured foundation, all new plumbing and electric, and high-end interior renovations throughout. Features include two 2-bedroom/2-bath unit and 1-bedroom/1-bath unit all within walking distance to train, shops, and restaurants. The upper floor offers cathedral ceilings in the master, floating vanities, sliding glass shower doors, open kitchen with marble counters and high end kitchen with GE appliances, walk-in pantry closet, washer/dryer, triple split-system HVAC with heat pumps, optional radiator heat, and square LED lighting, The main floor includes central HVAC, working fireplace, new kitchen with GE Cafe appliances, walk-in pantry, 27 bottle wine cooler, ultra-modern baths, sliding glass shower doors, floor-to-ceiling bathroom tile, two brand new NAVIAN high efficiency boilers. Exterior upgrades include brand new stucco, gutters, leaders, windows, a redesigned front facade with shed roof, underground Coltec drainage system, a six-car parking lot, EV charging station, three temperature-controlled 300 sq ft storage units at the driveway, and all new landscaping with gardens, walkways, paths, and a drainage system. Too much to list. A True Gem!!

137 Hillside Place, Eastchester

$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

$2,489,222

5 Beds ⋅ 5 Baths ⋅ 968446 MLS

Exquisite new 5 bedroom, 4.1 bath center hall colonial to be built offering refined luxury and timeless architectural elegance in an exceptional cul-de-sac setting. Perfectly positioned on just shy of one acre and backing the serene wooded grounds of the Edith Macy Center, this residence blends privacy, prestige, and natural beauty. A rare opportunity exists to fully customize finishes, materials, colors, and upgrades — allowing you to curate a home that reflects your personal vision and lifestyle. Upon entry, a dramatic double-sided staircase with an architectural catwalk creates a breathtaking focal point. Thoughtfully designed with 9-foot ceilings throughout and a soaring 20-foot cathedral ceiling in the family room, the home offers grand scale and open, light-filled living spaces. A statement fireplace anchors the family room, creating warmth and sophistication. The state-of-the-art chef’s kitchen will feature premium appliances, custom cabinetry, quartz countertops, and expansive workspace ideal for entertaining and everyday luxury living. Upstairs, generously proportioned bedrooms provide comfort and privacy, with the option to finish a bonus room tailored to your needs — whether a media lounge, private office, or fitness studio. The primary suite will serve as a tranquil retreat with spa-inspired bath potential. Additional exceptional features include: 3-car garage, expansive rear patio for seamless indoor/outdoor entertaining, large unfinished lower level, plumbed for future bath and endless possibilities, pool site potential in the rear yard. The home will be strategically set back and elevated on the property to maximize privacy, presence, and curb appeal. Driveway will be completely redone and re-pitched. House is currently staked out in yellow. Taxes are projected based on list price and consolidated tax rate and do not include STAR discount. A rare opportunity to build a luxury residence in a coveted location. Customize now and bring your dream home to life.

517A Old Chappaqua Road, Briarcliff Manor

$4,500,000

5 Beds ⋅ 7 Baths ⋅ 950756 MLS

1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!

150 Old Farm Road N, Chappaqua

$1,169,000

5 Beds ⋅ 3 Baths ⋅ 958299 MLS

For the buyer who wants to build something exactly right, 20 Old Farm Road in Scarsdale, NY is a rare opportunity. A five-bedroom, 2.5-bath Colonial on a sun-filled corner lot in Wilmot Woods, one of New Rochelle's most established neighborhoods, offered for the very first time after more than five decades in the same family. The home is being sold as-is and is priced accordingly. The structure itself is solid: generous room sizes, two-car garage, wood-burning fireplace, central air, finished basement, and a corner lot that offers openness, curb appeal, and real outdoor potential. With the Scarsdale 10583 post office address, easy access to multiple Metro-North stations, and a neighborhood known for its tree-lined streets and strong community character, the location delivers on every level. If you've been waiting for a home you can truly make your own in a location that already has everything, this is it.

20 Old Farm Road, Scarsdale

$2,650,000

5 Beds ⋅ 7 Baths ⋅ 929177 MLS

Welcome to an incredible retreat in beautiful Bedford, NY! This stunning 5-bedroom, 6.5-bath home spans over 10,000 square feet of elegant living space on nearly two acres of private land. From the moment you arrive, you will feel the warmth and sophistication of this well-designed residence. Step inside to find a gracious formal living and dining room that sets the tone for memorable gatherings. The expansive family room flows easily into a chef’s kitchen, complete with high-end appliances, custom cabinetry, and access to a spacious deck overlooking the grounds. The first-floor en-suite guest bedroom provides comfort and privacy, while the dedicated office offers a quiet place to focus or create. Upstairs, the primary suite feels like a personal getaway—featuring a cozy fireplace, two walk-in closets, a private balcony, and a luxurious bathroom designed for total relaxation. Three additional en-suite bedrooms and a wonderful bonus room complete this level, ensuring everyone has their own space. The lower level adds even more to love, with a media room for movie nights, a private gym, a walk-in spa like sauna, and a large family/game room with a full bar and bath that opens directly to the pool area . Outside, you’ll find a resort-like setting with an infinity-edge pool, relaxing spa, outdoor kitchen, and fire pit—perfect for unwinding or hosting. Set just 10 minutes from Scott’s Corners and downtown Bedford, this home blends tranquility with convenience, offering the best of refined living in a private, peaceful location.

496 Long Ridge Road, Bedford

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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.