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

$725,000

5 Beds ⋅ 3 Baths ⋅ 1037277 MLS

Enchanting, updated Victorian with character on a deep, private double lot nestled behind hedges and trees. Enjoy town & country living in historic Peekskill, across from an expansive park. Walk to shops, cafes, or train, 1 hour to Grand Central. Quintessential wraparound porch as well as back patio overlooking mature gardens & lawn with space for a future pool or garage. Inside features antique details, hardwood floors, high ceilings across 3 comfortable levels. The main floor boasts an ideal layout: entry, living & dining areas, full bath, laundry, walk-in pantry, new kitchen with quartz counters opening to a back patio, and a versatile office/guest bedroom. The basement offers updated systems, workshop space, & walk out bulkhead access. Upstairs, find 4 bright bedrooms, including a spacious primary with a custom closet, a spa-like bath with deep soaking tub, & a remodeled powder room. Heated, finished third floor has 3 bright bonus rooms with closets as well as attic storage.

304 Union Avenue, Peekskill

$3,499,000

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.

90 Greenhaven Road, Rye

$685,000

5 Beds ⋅ 3 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

$599,000

5 Beds ⋅ 4 Baths ⋅ 1034679 MLS

Wonderful opportunity to create your dream home in a highly desirable White Plains location. This spacious five-bedroom, four-bath Colonial offers a finished basement, fireplace, detached two-car garage, and excellent potential. The home needs updating and is conveniently located near schools, shopping, and public transportation. Bring your vision and make it your own.

780 Mamaroneck Avenue, White Plains

$3,950,000

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

$925,000

5 Beds ⋅ 3 Baths ⋅ 1035737 MLS

2 Units-6A features 2 bedroom, 2 baths w an EIK, deck off kitchen, 1st floor bathroom, washer/dryer hookup. Finished basement w additional storage space and additional room that can be used as an office. The roof on 6A was replaced in 2015 and added solar panels. Currently on a lease which expires in 2036. Monthly cost of panels is $65 and saves a ton on electric bill. Unit 6B features 3 bedrooms, 2 baths, separate dining area and kitchen, washer and dryer in place. Additional storage in basement. This unit is unique because it also features a basement apt with it's own walkout. Please note there is no C/O in place and will be responsibility of new owner to convert into a 3rd dwelling. House (s) Sold AS IS. This is a very rare opportunity to own and invest in a growing popular area like Pt. Chester. Only 0.7 miles to the train station, close to downtown shopping, and endless restaurants. This is a great opportunity to generate income and live in one of the units or to rent out both. An investors dream!

6 Angelo Place, Port Chester

$1,499,000

5 Beds ⋅ 6 Baths ⋅ 1027766 MLS

Experience timeless elegance in one of Westchester's premier country club communities, where history meets modern luxury. Presenting in Knollwood Country Club, 14 Crescent Drive. Beautifully reimagined while preserving the character and ambiance of yesteryear. This exceptional 5-bedroom, 6 Bath residence offers refined finishes, thoughtfully appointed spaces, and a gracious layout. A welcoming foyer leads to a beautifully updated kitchen with soaring ceilings, a charming breakfast nook, and direct access to the side patio and yard. The inviting living room, anchored by a fireplace, offers warmth and ambiance, while the formal dining room is perfect for memorable gatherings. At the heart of the home, the breathtaking great room is surrounded by panoramic windows that frame sweeping fairway views. French doors open to a spacious stone patio, creating an ideal setting for family and friends, outdoor dining, or simply relaxing with a glass of wine. The generous bedroom suites include a private au pair suite for guests or extended family. The exceptional primary suite is truly in a class of its own, with an oversized walk-in closet, a spa-inspired en-suite bath, separate shower, and luxurious jacuzzi tub. Every room captures breathtaking golf course views, creating a seamless connection to the surrounding landscape. Privately situated in one of Westchester's most desirable country club settings. This remarkable home offers a rare blend of timeless character, modern elegance, and an exceptional lifestyle.

14 Crescent Drive, Elmsford

$1,440,000

5 Beds ⋅ 3 Baths ⋅ 1030360 MLS

This 5-Bedroom, 2.1-Bath Split-Level Home in Greenville nestled on a quiet cul-de-sac in the highly acclaimed Edgemont School District, and only minutes from Scarsdale Village and the Metro-North Railroad Station, offering an ideal combination of convenience and suburban living. This move-in-ready home features new central air conditioning units, a new roof, some stainless steel appliances. The fully finished lower level includes a cozy fireplace and two versatile rooms, making it perfect for entertaining, a home office, guest accommodations, or extended family living. Step outside to enjoy the large deck and the stone patio, offering exceptional privacy for relaxing or hosting family and friends. For your convenience, the survey, property card, property disclosure, and floor plans are available for public review. Ideally located within walking distance to all schools and the express bus to New York City. Property taxes have never been grieved and do not reflect the STAR exemption. Buyers are encouraged to verify taxes and square footage prior to inspection or contract.

23 Greenville Road, Scarsdale

$1,350,000

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

$850,000

5 Beds ⋅ 3 Baths ⋅ 1030497 MLS

This Turn-Key two-family centrally located with amazing yard space is ready to be your next home! 3 Orchard Street offers two separate apartments highlighted by a first floor duplex including 3 bedrooms and 1.5 baths with granite countertops and top of the line finishes, featuring brand new carpeting and new split heating and cooling units throughout for year-round comfort. Enjoy access to an enclosed porch, perfect for gatherings and entertaining as well as a beautifully maintained outdoor patio and yard space. An ample driveway accommodating up to 4 cars adds exceptional convenience rarely found in the area. A perfect live-in unit or income producer at free-market rental rate! The second unit offers a spacious two bedrooms and a full bathroom with granite countertops, generous closet space throughout, brand new washer and dryer in unit, and its own new split heating and cooling system topped off with a beautifully finished attic space perfect for extra storage. Enjoy central location close to all major highways, shops, and public transportation. A great buy with no worries about renovations, don't miss out on this unique opportunity.

3 Orchard Street, Yonkers

$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, offering 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

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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.