Browse All Bay Shore NY 5 Bedroom Properties for Sale

Welcome to this beautifully maintained 5-bedroom, 2-bath home, lovingly cared for by the same owners for many, many years! This spacious and inviting property offers a wonderful combination of charm, comfort, and versatility, with part of the home currently utilized as an Airbnb, providing an excellent opportunity for additional income potential. Inside, you’ll find beautiful wood floors, crown molding, a cozy fireplace, central air, gas heat, and a bright, inviting sunroom perfect for enjoying your morning coffee or relaxing at the end of the day. The bedrooms are generously sized and the primary accommodates king-size furniture, while the large 'granny' attic offers abundant storage. Step outside to an amazing entertaining yard featuring a sparkling inground pool, spacious deck, and plenty of room for gatherings and summer fun. The large driveway provides ample parking, complemented by a garage for additional storage and convenience. Cedar-impression vinyl siding adds attractive curb appeal with easy maintenance. Ideally located less than a mile from Main Street and the railroad station, and close to the Fire Island ferries, hospitals, shopping, dining, and transportation. Whether you’re looking for a spacious home, an entertaining oasis, or a property with income-producing potential, this well-loved home offers it all!

73 Maple Avenue, Bay Shore

$689,900

5 Beds ⋅ 3 Baths ⋅ 1044627 MLS

Welcome home to this spacious Hi-Ranch nestled in the Bay Shore are, this stunning hi-ranch delivers five spacious bedrooms, three full baths, an eat-in-kitchen, a formal dining room, and an oversized living room designed for the way you live. The Layout offers incredible flexibility, making it an ideal candidate for a mother daughter set up with proper permits. Step outside and discover a parklike backyard, perfect for entertaining, relaxing and creating lasting memories. A few finishing touches away from perfection, this home is your blank canvas. Do not Miss this opportunity.

45 Massachusetts Avenue, Bay Shore

$757,000

5 Beds ⋅ 3 Baths ⋅ 1040683 MLS

Welcome to 16 West Drive, Bayshore. This move-in ready spacious single-family home with updated plumbing and electrical, new roof and lot more!!. Home offers comfort, flexibility, and ample living space. Ideal for a variety of lifestyles, this home features a bright and functional layout with plenty of natural light throughout. The updated kitchen is equipped with custom cabinetry, quartz countertops, stainless steel appliances and a practical workspace for meal preparation, while the adjoining living and dining areas create a warm and inviting atmosphere. Generously sized bedrooms on both floors provide generous space for relaxation, work, or guests, making it perfect for larger households or those needing extra rooms for offices or hobbies. The full bathrooms are conveniently located for everyday ease. Don't miss this opportunity to own a well-maintained home in a desirable neighborhood!

16 West Drive, Bay Shore

$619,999

5 Beds ⋅ 2 Baths ⋅ 1040654 MLS

Welcome to 21 Cherokee Drive, where space, flexibility, and opportunity come together! This spacious 5-bedroom, 2-full-bath home offers approximately 1,940 sq. ft. of living space and a truly unique layout that's perfect for today's extended or multi-generational household. The home is set up with two distinct ground-level living areas, offering the potential for a 3-bedroom setup on one side and a 2-bedroom setup on the other. The second living area already features kitchen cabinetry, providing a great head start for those looking to create a possible mother/daughter arrangement with proper permits. Freshly painted and ready for its next chapter, the home also features a new roof installed in 2020 and a brand-new 50-gallon gas hot water heater. Downstairs, a full unfinished basement offers a tremendous amount of additional space and potential—whether you're looking for storage, a workshop, recreation space, or room to bring your own ideas to life. With five bedrooms, two full baths, nearly 2,000 sq. ft., two flexible living areas all on one level, and a full basement, this is a home that can adapt to the way you want to live. Bring your vision and make 21 Cherokee Drive your own!

21 Cherokee Drive, Bay Shore

$829,000

5 Beds ⋅ 4 Baths ⋅ 1040238 MLS

Perfect opportunity for buyers with vision to bring this Pondersosa Style ranch in Southward estates to life !! Sitting on .085 acre lot you will have plenty of space to add your pool and your dream yard !! Once inside this 5 bedroom 3 .5 bath is ready for finishing touches . Living room ,Kitchen with nearby laundry area, full dining room, Master Suite, 3 bedrooms and upper level large bedroom with extra space for family or play room !!Located minutes from Downtown Bay Shore , Fire Island ferries, beaches, LIRR, Schools, Shopping and more!!

893 Gardiner Drive, Bay Shore

$1,788,000

5 Beds ⋅ 6 Baths ⋅ 1038627 MLS

Welcome to 16 S Montgomery Ave, a spacious and beautifully designed home offering 5 bedrooms and 5.5 bathrooms. The first-floor features 1 bedroom and 1.5 bathrooms, along with a kitchen, living room, and dining area. The second floor offers 4 bedrooms and 4 full bathrooms, providing exceptional space and privacy. Additional highlights include central heating and cooling, generous room sizes, abundant natural light, and a functional layout ideal for everyday living and entertaining. A wonderful opportunity for buyers seeking space, comfort, and convenience.

16 S Montgomery Avenue, Bay Shore

$559,000

5 Beds ⋅ 2 Baths ⋅ 1035708 MLS

Welcome to 23 Chris Matt Court, a spacious 5-bedroom, 2-full-bath home offering approximately 2,000 square feet of living space with 12 total rooms. Nestled on a quiet cul-de-sac in Bay Shore, this property presents an excellent opportunity for buyers looking to make a home their own. While the home does need some updating, it offers tremendous potential to add value and build equity. The generous layout provides plenty of space for large or extended families, entertaining, or a home office. Priced at just $559,000, this is a fantastic opportunity to own a sizeable home in a desirable neighborhood.

23 Chris Matt Court, Bay Shore

$500,000

5 Beds ⋅ 2 Baths ⋅ 1030527 MLS

This Colonial style home features 5 bedrooms and 2 baths, 1,488 sq ft of living space on a 4,792 sq ft lot. Needs work, priced to sell.

6 Hansen Street, Bay Shore

$899,000

5 Beds ⋅ 4 Baths ⋅ 1029811 MLS

Welcome 1641 East 3rd Avenue, Bayshore. This spacious, expanded cape offers five generously sized bedrooms and four full bathrooms, perfect for extended family or multigenerational living. A finished basement adds valuable recreation and living space, and the large property provides endless possibilities outdoors. Well-maintained and in good condition, this home is conveniently located near shopping, major highways, restaurants, and everyday amenities. Don’t miss this incredible opportunity to own a versatile and spacious home in the heart of Bayshore.

1641 E 3rd Avenue, Bay Shore

$599,000

5 Beds ⋅ 2 Baths ⋅ 1023123 MLS

Property Overview Address: 2 Seminole Drive Location: Bay Shore School District Lot Size: 0.29 Acres (oversized for the neighborhood) Living Space: 1,574 square feet Layout: 5 Bedrooms, 2 Full Bathrooms Basement: Semi-finished with Bilco door access, weather strip kit recently installed, recently painted, storage/rec space, and a plumbing utility ejector pump Key Interior Features Flexible Entry: Two separate entrances for enhanced privacy and daily convenience. Cosmetic Updates: Freshly painted living areas, newly painted basement floor, and modern brushed nickel door hardware. Kitchen Upgrades: Equipped with a newer stove, dishwasher, sink and fresh paint. Modern Lighting: Artika Sunnyvale "fandeliers" with remote controls in 2 of the main-floor bedrooms. Safety: Brand-new, dual-function smoke and carbon monoxide detectors installed throughout. Mechanicals & Energy Efficiency Primary Heat Source: Recently serviced boiler featuring a brand-new second-floor heating circulator pump. Secondary Heat Source: Extra-large Country wood-burning stove capable of heating the entire home. Hot Water: High-efficiency 50-gallon water heater installed in November 2025. Utilities: Upgraded 200-amp electrical service, enhanced gas lines, and a dedicated plumbing ejector pump. Exterior Shell: Durable roof (2013), energy-efficient Andersen second-floor windows. Exterior & Parking Amenities Detached Garage: 2-car structure perfect for vehicles, a workshop, or hobby storage. Driveway: Oversized layout accommodating multiple vehicles easily. Huge Backyard: Enclosed in black chain link. BBQ Amenity: Dedicated gas line for BBQ (no more propane tanks needed). Pool Potential: Plenty of space to accommodate any type of pool layout. Maintenance: Recent gutter repairs, thorough cleaning, and draft-reducing basement door sealing completed.

2 Seminole Drive, Bay Shore

$749,999

5 Beds ⋅ 2 Baths ⋅ 1020844 MLS

Welcome to your gorgeous colonial home that’s been awaiting you!! Nicely located within 10 minutes from shopping, dining, the Bay Shore Marina, and central to all LI's major highways. This beauty sits on 0.37 acres, boasts a Cul de sac driveway and falls nothing short of spectacular. The first floor hosts beautiful gray water-proof laminate hardwood floors throughout while having an open concept design with the spacious living room, a renovated kitchen that has endless soft close cabinetry which rests on breathtaking granite countertops, a large custom pantry, stackable W/D & a doggy haven near the front door for the fur baby lovers. The dining room, fully renovated bathroom with standup shower & 1 of the 5 bedrooms are also on the first floor along with a brand new Tankless Combo gas heat & hot water system. The second floor has a brand new bathroom that has a bath tub, a vanity with double sinks, bluetooth enabled surround sound, 4 spacious bedrooms that can easily fit queen size beds in it while the primary bedroom can have a California King bed to match its large walk in closet. Last but certainly not least, the backyard is a true hostess dream!!! Right off the sliding doors from the kitchen, The magnificent backyard has a full outdoor kitchen with a hibachi grill, bbq grill, ample counter space, mini fridge and high bar seating that can be used while watching T.V The outdoor living space is covered by 2 gazebos. You also have the option to take a swim in the beautiful` large above ground pool or the hottub- the possibilities to spend time with loved ones & friends under the stars is truly endless! This home will not last-run to make your showing appointment with me today! House is being sold as-is & 90% of outdoor oasis is included in the sale.

1634 N Gardiner Drive, Bay Shore

$699,000

5 Beds ⋅ 2 Baths ⋅ 1016661 MLS

Discover this large, expanded Cape in the heart of Bay Shore! Boasting 5 spacious bedrooms and 3 fully renovated baths, this home offers modern elegance and room for everyone—including a perfect space for mom. Just minutes from shopping, major routes, and Bay Shore’s vibrant amenities. Don’t miss your chance—schedule your private tour today!

27 Brook Avenue, Bay Shore

$899,999

5 Beds ⋅ 4 Baths ⋅ 1011097 MLS

Set on an impressive .44-acre lot, this beautifully renovated residence offers the perfect blend of space, comfort, and modern design. A long, paved driveway accommodates up to 10 vehicles, providing exceptional convenience for homeowners and guests alike. Surrounded by expansive lawn space and mature landscaping, the property immediately creates a sense of privacy, openness, and curb appeal that is rarely found. A welcoming front porch leads into a dramatic entry foyer featuring soaring double-height ceilings that create a stunning first impression. From the moment you step inside, you’ll appreciate the bright and airy atmosphere, enhanced by oversized windows, abundant natural light, gleaming hardwood floors, and impressive 9ft plus ceilings throughout. A spacious formal living room is highlighted by beautiful architectural details, including archways that create a natural flow from room to room. Flowing from the living room is a generously sized formal dining room capable of accommodating large gatherings with ease, making it perfect for holidays, celebrations, and entertaining. At the heart of the home is a bright and inviting kitchen surrounded by windows, allowing natural light to pour in throughout the day. Featuring stainless steel appliances including a built-in microwave, refrigerator, dishwasher, extensive cabinetry, and generous countertop space, the kitchen is designed to accommodate both everyday living and entertaining. The open and airy design creates a seamless connection between the kitchen and surrounding living spaces, allowing conversation and activity to flow effortlessly throughout the home. Sliding glass doors provide direct access to the backyard, extending the living space outdoors. Just beyond the kitchen is an open-concept family room that serves as the centerpiece of daily living. Whether preparing meals, entertaining guests, or enjoying a quiet evening at home, the layout allows everyone to remain connected. An electric fireplace serves as a beautiful focal point, adding warmth and character to the space. Completing the first floor is a conveniently located powder room and a spacious mudroom and laundry area, offering practical functionality for today’s active lifestyles, pets, and everyday organization. Beautiful wooden staircase leads to the second level, where you’ll find four generously sized bedrooms, each offering ample closet space, hardwood flooring, and large windows that fill the rooms with natural light. A well-appointed full bathroom serves the secondary bedrooms. The oversized primary suite offers a true retreat, featuring exceptional proportions, dual closets, and a beautifully updated en-suite bathroom complete with double vanities, quality finishes, and a bright, spa-like atmosphere. Additional attic storage space provides practical storage options for seasonal and household items. The fully finished lower level dramatically expands the home’s usable living space with approximately 8.5-foot ceilings, creating a bright and comfortable environment rarely found in lower levels. Complete with a wet bar and separate outside entrance, this versatile space can easily accommodate recreation, entertaining, fitness, hobbies, media space, or a variety of lifestyle needs. Step outside to your own private backyard retreat. Set on nearly half an acre and fully fenced for privacy, the property offers an exceptional amount of outdoor space to enjoy. A spacious 30’ x 20’ deck provides the perfect setting for outdoor dining, and gatherings while overlooking the expansive backyard. An oversized attached one-car garage provides additional parking and storage. Conveniently located near shopping, dining, parks, transportation, and everyday amenities, this home offers the perfect combination of space, quality, comfort, and convenience. A rare opportunity to own a beautifully renovated home on a substantial lot with the indoor and outdoor space today’s buyers are searching for.

40 Muncey Road, Bay Shore

$1,499,990

5 Beds ⋅ 4 Baths ⋅ 1001324 MLS

Nestled on Long Island’s coveted South Shore in desirable Bay Shore, this stunning five-bedroom ranch offers luxury living with a true resort-style feel. Beautifully landscaped grounds create a private backyard oasis featuring an Olympic-size swimming pool, expansive patio for entertaining, and a lighted professional tennis court for day or evening play. Inside, the home blends comfort and sophistication with an oversized family room ideal for gatherings, a sunroom showcasing panoramic yard views, and a chef’s kitchen featuring premium appliances, including a full-size Sub-Zero refrigerator and separate full-size Sub-Zero freezer with abundant storage. Recent upgrades include a Brand New sprinkler system, owned solar panels, a renovated double shower in the primary suite, updated heating and A/C in the kitchen, and a newly installed 5-ton central A/C unit. An upper-level bedroom with a private roof deck overlooks the pool and tennis court, completing this exceptional Bay Shore retreat. A rare opportunity to enjoy luxury, recreation, and effortless South Shore living.

9 Dove Lane, Bay Shore

$999,999

5 Beds ⋅ 3 Baths ⋅ 977405 MLS

Nestled in the coveted Penataquit Point community, this impressive Bay Shore residence offers sweeping views of the Great South Bay and a lifestyle of comfort and elegance. With five generously sized bedrooms, including a spacious primary suite complete with a private bath and dressing area, this home is designed to accommodate both privacy and ease of living. A bright and open kitchen with ample dining space leads directly to an expansive deck, setting the stage for seamless indoor-outdoor living. The backyard is perfectly suited for entertaining or quiet relaxation, framed by natural beauty & plenty of room for a pool. Inside, you'll find a spacious living room that connects effortlessly to the formal dining area—ideal for hosting. A cozy three-season room adds charm and versatility, providing a peaceful retreat throughout much of the year. Additional features include a wood-burning fireplace, a family room with wet bar, and a flexible bonus space that functions well as a home office or gym. The property also includes a large circular driveway and a detached 2.5-car garage, offering abundant parking. A separate entrance adds convenience for multigenerational living or visiting guests. Located just minutes from Fire Island ferries and local amenities, 146 Awixa Avenue is a rare offering in one of Bay Shore’s most desirable waterfront neighborhoods. **Renderings of Possible Kitchen Renovation Concepts & Pool Placement Options**

146 Awixa Avenue, Bay Shore

$3,350,000

5 Beds ⋅ 5 Baths ⋅ 973534 MLS

To-be-built remarkable colonial on one of the most beautiful and sought-after streets in Bay Shore, set on just shy of 1.5 acres with stunning water views of the Great South Bay from the second level. This exceptional 5-bedroom, 4 full bath, 1 half bath residence will feature thoughtfully designed living space and the rare opportunity for full customization, allowing the buyer to tailor every detail to their taste and lifestyle. Proposed features include 10ft first floor ceilings, a state-of-the-art chef's kitchen connecting to a formal dining room through the butler's pantry, additional breakfast room, family room with gas fireplace, spacious great room with gas fireplace- perfect for everyday living and entertaining. A stunning sunroom filled with abundant natural light creates the perfect place to relax while enjoying the surrounding beauty. The home will also feature a charming second-floor balcony overlooking the bay attached to a large master suite with his and her closets, walk in closets in the additional bedrooms, a laundry room on the second level, and beautiful carport, perfect for bringing in groceries, and a detached two-car garage. A truly unique opportunity to build your dream home in a premier Bay Shore location.

100 Awixa Avenue, Bay Shore

$665,000

5 Beds ⋅ 2 Baths ⋅ 968538 MLS

Welcome to 1081 Bay Shore Ave, a spacious Hi-Ranch home offering comfort, functionality and style! This beautiful property features 5 bedrooms and 2 full bathrooms , an open concept kitchen that flows into a formal dining room and living room. The lower level offers flexible living space with a separate outside entrance and potential for accessory use with proper permits. The property offers a spacious deck overlooking a Koi Pond, and a beautiful yard perfect for entertaining. This home is move in ready with plenty of space and possibilities. Property is being SOLD AS IS !!

1081 Bay Shore Avenue, Bay Shore

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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.

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