Bayside Estates Homes under $500,000

Bayside Estates Homes under $500,000

Welcome to Bayside Estates, a hidden gem nestled in the picturesque Fort Myers Beach, Florida, where coastal charm meets vibrant community living. This delightful development offers a unique blend of serene waterfront views and a warm, welcoming atmosphere, making it the perfect destination for those seeking a tranquil lifestyle without breaking the bank.

Bayside Estates is renowned for its stunning homes, many of which are available for under $500,000, providing an incredible opportunity for first-time buyers, retirees, or anyone looking to invest in a slice of paradise. These well-appointed residences boast a variety of styles and sizes, ensuring there’s something to suit every taste and preference. Imagine waking up to the gentle sound of waves lapping against the shore, all while enjoying the comforts of a beautifully designed home.

Living in Bayside Estates means more than just owning a home; it’s about embracing a lifestyle filled with outdoor adventures, social gatherings, and community spirit. Residents can take advantage of the nearby beaches, indulge in water sports, or explore the local dining and shopping options that Fort Myers Beach has to offer. With a strong sense of community, neighbors become friends, and every day feels like a vacation.

Whether you’re looking for a seasonal retreat or a permanent residence, Bayside Estates presents an exceptional opportunity to own a piece of Florida’s paradise without exceeding your budget. Come and discover the charm of Bayside Estates, where your dream home awaits!

Newest Bayside Estates Homes under $500,000

11390 Azalea Lane, Fort Myers Beach
$264,900
2 Beds ⋅ 2 Baths ⋅ 2026043053 MLS
YOUR SLICE OF TROPICAL PARADISE AWAITS IN BAYSIDE ESTATES! Enjoy gorgeous canal views, visiting manatees, and the best of Southwest Florida waterfront living in this beautifully updated 2-bedroom, 2-bath, furnished home located in the highly desirable Bayside Estates boating community! Built in 2006 and elevated higher than many surrounding homes, this spacious 1,188-square-foot residence features soaring ceilings, an open and inviting floor plan, luxury vinyl flooring, beautiful quartz countertops, a NEW A/C, and a durable metal roof! The oversized primary suite offers a walk-in closet and private bath with dual sinks. Additional conveniences include indoor laundry and plenty of room to relax and entertain. Situated on a LARGE CORNER LOT with TWO DRIVEWAYS, this property offers exceptional outdoor space! Enjoy your morning coffee on the screened lanai, unwind on the patio, or simply take in the peaceful canal views and watch the manatees swim by. This is the Florida lifestyle you've been dreaming of! Bayside Estates is a vibrant 55+ boating community offering an incredible selection of activities and amenities, all conveniently located near Fort Myers Beach, restaurants, shopping, and everything Southwest Florida has to offer! Whether you're looking for a seasonal getaway or your full-time Florida retreat, this home checks all the boxes! Don't miss this opportunity to own your own piece of paradise. Schedule your private showing today! Buyers pay a $2,800 resale capital contribution fee.

11390 Azalea Lane, Fort Myers Beach
17611 Canal Cove Court, Fort Myers Beach
$479,000
2 Beds ⋅ 2 Baths ⋅ 226036884 MLS
If you’ve been considering Bayside Estates as your next home or investment opportunity, there has never been a better moment to make your move. Home and lot prices are currently more attractive than they were even after the hurricane three years ago, and recent months have brought a wave of savvy buyers eager to secure property in this highly desirable community. This particular home is an exceptional find for anyone wanting to enjoy Bayside without stretching their budget. Priced at only $479,000, it features two generously sized bedrooms, two bathrooms, a den or office, a beautifully updated kitchen, a spacious family room, a bright Florida room and not only a one car garage but also carport. Step out back and you’ll find a waterfront deck and boat lift—the perfect place to unwind with a glass of wine while watching the sun set. There is even room for your own private swimming pool if you desire. The garage offers ample room to store your electric bicycles, canoe, or any of your favorite recreational toys not to mention a full-size car or truck. Don’t wait—opportunities like this don’t last long. Schedule your visit today and see why now is the ideal time to buy. Bayside Estates truly is the best-kept secret of Fort Myers Beach. This vibrant and welcoming 55+ community is considered the crown jewel of the Gulf Coast. Just 2.5 miles from the beach, residents can access the shoreline by car or by boat—from their own driveway or private dock. A favorite pastime among residents is riding electric bicycles to the beach and spending the day near the world-famous Jimmy Buffett’s Margaritaville-just don't step on a pop top. Convenience is unmatched, with nearly all major retail options just minutes away. For those new to Bayside Estates, it’s an incredibly fun place to live—often described as a “mature person’s playground.” Whether you love pickleball, tennis, bocce ball, lounging by the community pool, enjoying a swim in the heated community pool, or cruising the neighborhood in your swanky golf cart, there’s always something happening around here. Most importantly, the people here are friendly, active, and ready to welcome you with open arms.

17611 Canal Cove Court, Fort Myers Beach
11220 Bayside Lane, Fort Myers Beach
$489,777
2 Beds ⋅ 2 Baths ⋅ 2026041880 MLS
THIS ISN'T JUST A HOME—IT'S A LIFESTYLE! Quality construction, thoughtful design, and an incredible location come together in this beautifully maintained home in Bayside Estates. Situated just steps from the clubhouse and pool, this 2-bedroom home also offers an office/sunroom that provides flexible additional living space. With up to five parking spaces and a full garage beneath the home, there is room for vehicles, storage, and all the extras that come with enjoying Southwest Florida. The quality of construction is one of the features that truly sets this home apart. Built on a substantial steel I-beam structure with a 12' steel frame, 2x10 floor joists, 2x6 walls, concrete pad, and helical supports beneath the steel beams, the home was designed with durability in mind. Hurricane windows, a hurricane-rated garage door, steel garage siding, composite decking and stairs, and a premium insulation package add to the home's thoughtful construction. Inside, you'll find 9' ceilings, complete drywall, LVP flooring throughout, recessed lighting, and a chandelier over the dining area. The kitchen features an island and quality appliances, while the primary suite offers a double-sink vanity and large walk-in closet. The Allied commercial HVAC system features a variable-speed heat pump with 18.2 SEER2 efficiency. A screened lanai overlooks the community and creates the perfect spot to relax with a glass of wine at the end of the day or coffee at the beginning. Get this...paver area ready for a hot tub. And then there is Bayside Estates. This is a community where neighbors gather, activities are plentiful, and there is always something happening at the clubhouse. Residents have access to a community pool, pickleball, tennis, shuffleboard, horseshoes, bocce, fitness facilities, library, community room, cards, gatherings, and a busy social calendar. All of this with a very low HOAfee! Best of all, the location puts you just 2.5 miles from the sugar-sand beaches of Fort Myers Beach. Ride your bike to the island, take the trolley, or make the quick drive to the beach, restaurants, entertainment, and waterfront destinations. The Sanibel Causeway is also just minutes away, opening the door to spectacular sunsets, shelling, boating, and exploring everything Southwest Florida has to offer. Whether you're looking for a full-time residence, seasonal retreat, or a place to enjoy between adventures, this home delivers a rare combination of quality construction, community, and proximity to the beach. Transferable flood insurance policy may be available; buyer to verify terms and transferability with the insurance provider. 55+ community.

11220 Bayside Lane, Fort Myers Beach
11321 Bougainvillea Lane, Fort Myers Beach
$285,000
2 Beds ⋅ 2 Baths ⋅ 2026039586 MLS
2-Bed/2-Bath water front home with DIRECT GULF ACCESS, NO BRIDGES OR LIFT STATION! Beautiful south facing canal views! NEW DOCK WITH electric BOAT LIFT. Enjoy the dolphins, manatees and fishing right outside your door. The open floor plan allows for great entertaining space inside and out! . COMPLETE REMODEL!stainless appliances, soft close kitchen cabinets, stone surfaces and pantry. New drywall, insulation, electric and 3 mini split AC , subfloor, vinyl plank flooring, cabinets with stone surfaces and stone vanities, new showers and toilets. Large florida room with laundry and strorage. The deep carport parks 2+ vehicles. . Bayside Estates is a highly desirable community with community pool, tennis, pickle ball, horse shoes, bocce ball, community room and library. Enjoy boating to Ft. Myers Beach, Sanibel and all of the local restaurants and beaches right from your dock. Drive minutes to beaches, restaurants shopping and more! 55+ community. Community offers pickle ball, tennis, shuffle board, pool, work out facility, library, club house, horseshoes, community parties, cards, and tons of social events. Owner open to rental options. Transferable flood insurance.

11321 Bougainvillea Lane, Fort Myers Beach
17620 Bryan Court, Fort Myers Beach
$340,777
2 Beds ⋅ 2 Baths ⋅ 2026035446 MLS
Beautifully updated 2-bedroom, 2-bath home in Bayside Estates, showcasing meticulous attention to detail throughout. The property features a covered carport with electric hurricane shutters, professional landscaping, inviting canal views, and a covered back patio perfect for enjoying the Florida setting. Inside, built-in buffet cabinetry and thoughtful updates create a comfortable and stylish living space. Bayside Estates offers a low HOA and an array of community amenities and activities, including dinners, live bands, boating opportunities, and social gatherings. Conveniently located approximately 2.5 miles from the island, with easy access for biking to the island’s restaurants and entertainment, including Margaritaville. Whether relaxing at home, enjoying time on the water, or exploring nearby dining and entertainment, this beautifully maintained property provides an opportunity to embrace the Southwest Florida lifestyle.

17620 Bryan Court, Fort Myers Beach
17920 Bryan Court, Fort Myers Beach
$310,000
2 Beds ⋅ 2 Baths ⋅ 2026024155 MLS
Located at Bayside Estates, a 55+ Community. This 1406 sq. ft. Canal Front Home has Easy Direct Access to the Gulf of America for your boating needs. This Home is Furnished and has nearly New Appliances. The HVAC and Water Heater are approximately 1yr. Old. Both bathrooms have Hard Surface Countertops with the Master having Double Sinks. Both Bedrooms have walk in Closets. Bayside Estates the Best Kept Secret of Fort Myers Beach. This incredibly active and friendly community is the crown jewel of the Gulf Coast. Bayside is 2.5 miles from the beach and is accessible by car or boat. Bayside Estates is a very fun and friendly place to call home. Whether you want to play pickle ball, Tennis, boce ball or hang out at community pool, or simply cruise the hood in your golf cart there is something always going on. The owner has a recent Home Inspection Report that is available to the purchaser to save them $600.

17920 Bryan Court, Fort Myers Beach
17540 Peppard Drive, Fort Myers Beach
$340,777
2 Beds ⋅ 2 Baths ⋅ 2026022382 MLS
This beautifully remodeled Gulf-access home combines coastal elegance, modern upgrades, and exceptional outdoor living in one move-in-ready package. Offered with furnishings in a casual yet sophisticated coastal style, this meticulously maintained 2-bedroom, 2-bath residence features newer vinyl plank flooring throughout, newer shaker-style cabinetry, granite countertops, custom stone backsplash, stainless steel appliances, updated vanities, tiled showers, impact glass in the Florida room, and custom closet cabinetry in the guest bedroom. The thoughtfully designed kitchen includes a built-in desk overlooking the water — the perfect place to work, plan, or simply enjoy the peaceful canal views. Major improvements include newer A/C with updated ductwork, mini split systems for enhanced comfort, a newer hot water heater, and maintenance contracts already in place for lawn care, pest control, and A/C servicing. The spacious Florida room and lanai create inviting indoor-outdoor living spaces ideal for relaxing or entertaining. Situated on a large corner lot with lush mature tropical landscaping, the property also offers an extra-wide driveway with room for up to five vehicles, a spacious covered carport, and a detached outbuilding with additional storage, washer/dryer area, and extra screened entertaining space. Outdoor living truly shines with a large Trex dock, newer boat lift, kayak storage, and direct Gulf access for boating enthusiasts. Located in the highly desirable Bayside Estates, a pet-friendly 55+ boating and golf cart community where you own the land, residents enjoy an active lifestyle with amenities including a community pool, pickleball, tennis courts, shuffleboard, bocce ball, activity center, and numerous social activities. Quarterly HOA fees of $700 include internet, lawn and land maintenance, water, sewer, and trash service. Ideally positioned just 2.5 miles from Fort Myers Beach and minutes from Sanibel Island, this home offers convenient access to world-famous beaches, waterfront dining, entertainment, shopping, and the newly built Margaritaville resort. Move right in and enjoy the ultimate Southwest Florida lifestyle.

17540 Peppard Drive, Fort Myers Beach
11391 Cypress Lane, Fort Myers Beach
$309,000
2 Beds ⋅ 2 Baths ⋅ 2026020491 MLS
A charming canal-front manufactured home nestled in the welcoming Bayside Estates community. Boat lift and dock are ready for your boat. This delightful 2-bedroom + den, 2-bath retreat spans approximately 1,458 square feet and sits on a cozy 3,920 sq ft lot. Sip your coffee from the porch and watch the dolphins play. Step into a bright, airy layout that flows effortlessly into a screened porch and private patio—perfect for morning coffee or evening relaxation. The lush landscaping and direct canal access make this home a tropical oasis for boating enthusiasts and those seeking serene waterfront living. Bayside Estates offers a vibrant, active lifestyle with amenities like a clubhouse, pool, tennis and pickleball courts, shuffleboard, spa/hot tub, and more—all included in the HOA. Conveniently located just minutes from Fort Myers Beach, you’ll enjoy easy access to local favorites such as Bayfront Bistro, Publix Super Market, Snook Bight Marina, and many more.

11391 Cypress Lane, Fort Myers Beach
11291 Bougainvillea Lane, Fort Myers Beach
$347,900
2 Beds ⋅ 2 Baths ⋅ 2026015741 MLS
This meticulously updated 2-bedroom + den, 2-bath canal-front home with direct Gulf access is a boater’s paradise right from your dock. Seller offering Seller Financing! This home has been completely renovated from top to bottom, featuring a new A/C system, updated plumbing, a durable metal roof-over with reinforced carport, modern kitchen cabinetry with Samsung Bespoke appliances, plantation shutters, and luxury vinyl plank flooring installed over a reinforced plywood subfloor. Both bathrooms have been stylishly upgraded, and the home is fully insulated with spray foam—including the walls and underneath—for maximum comfort and efficiency. Step inside to a spacious screened lanai, perfect for entertaining family and friends. The lanai can also be fully opened to accommodate parking for your car and golf cart. The open-concept kitchen, dining, and living areas create a bright, inviting space ideal for everyday living. The primary suite features an updated bath with custom shower, while the guest bedroom and bath are conveniently located down the hall. The cozy den/sunroom—accessible from both the rear and the primary bedroom—offers a versatile space for guests or a peaceful retreat. Outside, enjoy a low-maintenance decorative paver driveway leading to the rear screened patio and a new composite dock with canopy, updated electrical, and beautiful canal views. Located in Bayside Estates, a vibrant 55+ boating community filled with amenities and activities, this home offers the perfect blend of relaxation and recreation. Take leisurely morning strolls, spend your days at the beach, and unwind with stunning sunset views—this is coastal living at its finest. Additional highlights include a Transferable Flood Insurance policy. Buyers in Bayside pay a $2,800 resale capital contribution fee.

11291 Bougainvillea Lane, Fort Myers Beach
17770 Bryan Court, Fort Myers Beach
$434,777
2 Beds ⋅ 2 Baths ⋅ 2026014921 MLS
Welcome to Bayside Estates, a desirable 55+ waterfront community offering relaxed coastal living. New construction and elevated to current standards, this canal-front home delivers modern quality and peace of mind—why wait to build when you can move right in and start enjoying it today? This property features a private dock with lift and canopy, ideal for boating and water access. Professionally landscaped and thoughtfully designed, it’s well-suited for seasonal use, full-time living, or as an investment opportunity. Enjoy your private balcony—perfect for morning coffee or evening refreshments while taking in the coastal surroundings. Located just 2.5 miles from Fort Myers Beach, you’ll have convenient access to the shoreline by tram, e-bike, or car, all while being tucked away from heavier traffic. Take advantage of nearby destinations like Margaritaville Beach Resort Fort Myers Beach and enjoy the ease of a move-in-ready home designed for comfortable coastal living.

17770 Bryan Court, Fort Myers Beach
17561 Canal Cove Court, Fort Myers Beach
$499,900
3 Beds ⋅ 2 Baths ⋅ 2026008561 MLS
Beautiful 3-bedroom, 2-bath home with quick access to the Gulf of Mexico! Wake up to beautiful morning sunrises and enjoy tranquil preserve views from your own canal-front property. Inside, you’ll find a thoughtfully designed open-concept layout that was completely remodeled in 2023. The kitchen features upscale appliances, granite countertops, and a spacious walk-in pantry. With a breakfast bar and seamless flow between the dining and living areas, this home is perfect for entertaining. Split floor plan offers a private primary suite with an en-suite bath that includes a custom shower. The guest bedroom, den, and additional bath are thoughtfully located on the opposite side of the home for added privacy. Step into the rear sunroom, which is fully air-conditioned and showcases sweeping canal and preserve views, AND no neighbors behind you. The expansive multi-level paver patio (with plenty of room to add a pool) leads directly to your captain’s walk dock and boat lift. 2-car covered carport can be an enclosed, making your own enclosed space to park your vehicles with extra storage. foundation certification. All Tie-Downs and Straps have been replaced under the home and is engineer certified to meet HUD Permanent Foundation requirements. Your slice of tropical paradise awaits! Bayside Estates, is a highly desirable boating community, close to beaches, restaurants and everything SW Florida has to offer. This fantastic 55+, manufactured home community has so many activities to choose from. The community Clubhouse & Office now have a water barrier planking system up to 31” High & Cool Seal waterproof insulated paint. Buyers in Bayside pay a $2800 resale capital contribution fee. Call to schedule your private showing!

17561 Canal Cove Court, Fort Myers Beach
17721 Stevens Boulevard, Fort Myers Beach
$309,777
2 Beds ⋅ 2 Baths ⋅ 2026006036 MLS
Located at 17721 Stevens Blvd, this waterfront property offers a premier opportunity to join the active 55+ community of Bayside Estates. Positioned on a canal with direct access to the Gulf of Mexico, this location is ideal for those who want to be on the water and minutes from the best of the local area. The interior features a functional layout highlighted by a kitchen outfitted with durable granite countertops. This home comes partially furnished, easing your transition into the Florida lifestyle. A standout feature is the large owner’s suite, which provides ample room for a full bedroom set and a private seating area, serving as a quiet retreat within the home. The living area is extended by a large, finished lanai in the back. Included in the home's total square footage, this versatile, enclosed space functions as a sunroom or secondary living area, allowing you to enjoy the canal views year-round. Living in Bayside Estates means enjoying a low-maintenance lifestyle where the monthly fees cover essential services including lawn care, water, trash, and internet. Residents also have access to a wide array of amenities such as a community pool, pickleball, tennis, and a busy clubhouse social calendar. The location is perfectly situated for beach lovers and explorers alike. You are located just 2.5 miles from the sugar-sand shores of Fort Myers Beach—a quick 5-minute drive or an easy bike ride away. Additionally, the property is just minutes from the Sanibel Causeway, providing fast access to world-class shelling and sunsets. Whether you are looking for a permanent residence or a seasonal escape, this property combines updated finishes with an unbeatable location.

17721 Stevens Boulevard, Fort Myers Beach
Start Your Search

How much is your home worth?

Get instant property value now!