Florida Waterfront Homes for Sale in Hillsborough County Florida United States

LAKEFRONT LOT in GATED NEIGHBORHOOD of HIDDEN HARBOR * 0.52 ACRES * PICK YOUR OWN BUILDER * BUILD ON YOUR TIMELINE * TENNIS COURTS, GAZEBO, BASEBALL DIAMOND and a FISHING PIER OVERLOOKING the NEIGHBORHOOD POND. Last available buildable LAKEFRONT lot in the EXCLUSIVE, GATED Hidden Harbor community, nestled on the stunning shores of Lake Toho, part of the renowned Chain of Lakes. This 0.52-acre cleared lot is ready for your dream home, offering sunrise views, lush oak trees, and a serene, private setting with no building time restrictions—pick your own builder! Enjoy resort-style amenities including tennis courts, a pond, fishing pier, and secrity gate, all within an established, low-HOA neighborhood. Ideal for both investment or personal use, this prime location is just minutes from NEO CITY AND NEO CITY ACADEMY, DOWNTOWN KISSIMMEE, popular travel destinations, shopping, restaurants & much more. With access to top bass fishing lakes and the ability to boat to the coast, this is an opportunity you won’t want to miss!

Rare opportunity to own nearly 2 acres of direct lakefront property on the pristine Lake Minnehaha, part of the highly desirable Clermont Chain of Lakes. Nestled in one of Central Florida’s most scenic and sought-after waterfront communities, this expansive property offers the perfect canvas to build your custom luxury dream home and private dock, all with beautiful views of the lake and breathtaking sunsets and NO HOA. The existing home offers value primarily in the land and location—providing an ideal teardown opportunity to create your personalized estate. With elevated views of Lake Minnehaha, well know for water sports such as wakeboarding, water skiing and fishing, this homesite offers room for an expansive residence, pool, and outdoor living space—all with private lake access just steps away. Design and build a custom dock tailored to your boating lifestyle-whether you need space for a wake boat, pontoon, jet skis or a covered lift, create the perfect setup for enjoying lake days. Imagine waking up to glassy water perfect for early morning paddleboarding, sunset cruises by boat, or weekend wake surfing and jet skiing with friends and family. The Clermont Chain of Lakes is renowned for its clear freshwater, connecting 11 lakes ideal for boating, fishing, and waterfront dining. It’s a lifestyle that blends recreation, relaxation, and natural beauty—all within a vibrant and active community. Located minutes from historic downtown Clermont, you’ll enjoy local restaurants, boutique shopping, farmers markets, and year-round festivals. With easy access to Orlando, theme parks, shopping, and a thriving lakeside culture, this is more than a property—it’s a lifestyle investment. Whether you’re envisioning a grand lakefront estate or a serene retreat surrounded by nature, this property is a rare gem waiting to be reimagined.

REGAL BAY - EXCLUSIVE GATED LAKEFRONT PRIVATE COMMUNITY with ONLY 24 homes on a PENINSULA offering Incredible Sunset's and the spectacular morning sun. LAKE TOHOPEKALIGA and the KISSIMMEE CHAIN of Lakes Famous for the top Bass Fishing, offers a SANCTUARY surrounding this Charming Home at 1465 Riviera Drive. Stunning 4-Bedroom, 3.5-Bathroom Home with Breathtaking Lake Views in Regal Bay. Start your mornings with a cup of coffee while soaking in the serene lakefront views and end your day with unforgettable sunsets. This exquisite home offers a rare opportunity to live right on the water with your own private dock and boat access, all in the highly sought-after Regal Bay community. The gourmet kitchen is a standout, featuring elegant granite countertops, stainless steel appliances, and a spacious island with seating, making it perfect for both everyday meals and entertaining. The walk-in pantry adds extra storage space for your convenience. The inviting family room boasts a grand stone fireplace, soaring vaulted ceilings, and a built-in bar. Large sliding doors open to a private outdoor oasis with direct access to the water, ideal for enjoying Florida’s beautiful weather. The master suite is truly a retreat, offering a private balcony with stunning lake views, a luxurious Jacuzzi tub, a walk-in shower, double sinks, and a generous walk-in closet. A guest bedroom on the lower level includes a double closet and an ensuite bathroom, offering comfort and privacy for visitors. The spacious loft area provides versatile space, perfect for a game room, extra living area, or home office. Enjoy the Florida lifestyle with multiple outdoor spaces, including a screened porch, two balconies, and your own private dock with a seawall. Additional thoughtful features include a laundry room with cabinetry, central vacuum, intercom system, and pocket doors for added convenience. Improvements: New Roof(2017), New AC(2017 & 2020), New Dock & Seawall (2016) Invisible Fence for pets(2024) As part of Regal Bay, you’ll have access to a community pool, cabana, and tennis courts, providing resort-style amenities just steps from your doorstep. This lakeside gem blends luxury, comfort, and convenience seamlessly. Don’t miss the opportunity to make it yours — schedule a tour today! #LakeLife #Lakefront

CYPRESS SHORES - WATERFRONT HOME with a neighborhood PRIVATE BOAT RAMP on LAKE TOHO - CYPRESS SHORES Embrace waterfront living at its finest in this exquisite canal-front residence! This single-story gem boasts 2 large bedrooms, 2 bathrooms, and a screened pool with a relaxing lanai overlooking the tranquil waters. Situated on an oversized lot(0.47 Acres) in a peaceful neighborhood without HOA restrictions, this home offers direct access to Lake Toho and the Kissimmee Chain of Lakes for endless aquatic excursions. With plentiful parking space and a 2-car garage, convenience is key. Enjoy the best of both worlds with close proximity to Kissimmee and St. Cloud, as well as easy access to the Turnpike for seamless commuting. Inside, revel in the elegance of Brazilian Cherry wood flooring, crown molding, neutral paint colors and ceiling fans in every room, enhancing the ambiance of this serene abode. Unwind in the spacious living room or family room, and savor the stunning views and sunsets from the outdoor patio. With modern amenities like an inside laundry/utility room, this home offers a perfect blend of comfort and sophistication for your waterfront oasis. Situated in an established neighborhood, this home is conveniently located close to restaurants, shopping, popular travel routes, area attractions, beaches, NEO City and the Orlando International Airport. Don’t miss the opportunity to own a piece of paradise where every detail is designed for your utmost comfort and convenience. All measurements are approximate and to be independently verified by buyer * THIS PROPERTY IS NOT ZONED SHORT TERM RENTAL. - ROOF(2014) - WATER KINETICO WATER SYSTEM - WATER HEATER(ORIGINAL) - PRIVATE ROAD - VOLUNTARY CANAL MAINTENANCE($350/YEAR) - POOL RESURFACED, RETILED & REPAINTED (2020)

Stunning Lakefront Estate with Pool and Dock in Gated Hickory Hammock. This is a rare opportunity to own a luxury residence on Johns Lake, located in vibrant Winter Garden. This beautifully appointed Lewiston floor plan offers five bedrooms, four full bathrooms, two half baths, and a host of refined upgrades throughout—perfectly blending elegance, comfort, and Florida outdoor living. From the moment you enter, you’re welcomed by a dramatic two-story foyer with 20-foot ceilings, a striking grand staircase, and an elegant powder room. Just off the entryway, a flexible space can serve as a formal dining room, living room, or home office to suit your lifestyle. At the center of the home is an impressive chef’s (super) kitchen, designed for both entertaining and everyday living. It features two large, wood-wrapped islands—one with a sink and one with counter seating—quartz countertops, white cabinetry with custom drawer storage, frosted glass accent doors, a stylish backsplash, and a double oven (including convection). The electric cooktop, walk-in pantry, sunlit dinette, and included appliances make this kitchen as functional as it is beautiful. The open-concept family room flows seamlessly to the outdoors through triple sliding glass doors. Step outside into your private retreat featuring a fully fenced backyard, resort-style saltwater pool with lap lane, 10-foot depth, and sun shelf—all surrounded by lush landscaping. Just beyond, follow a grassy path to your private boat dock, complete with electric, water, 7,500-pound lift, Trex walkway, ladder, and seating area. It's the perfect place to relax and enjoy the breathtaking sunsets and nightly Disney fireworks over Johns Lake. The thoughtful layout includes a first-floor in-law suite with a private entrance, full ensuite bath with walk-in shower, walk-in closet, and screened patio—ideal for guests or multigenerational living. Upstairs, the spacious primary suite offers panoramic lake views through a wall of windows, tray ceilings, and French doors that open to a private balcony overlooking the pool, backyard, and waterfront. The luxurious ensuite bathroom includes two vanities, a garden tub, large walk-in shower, and generous closet space. Three additional upstairs bedrooms include one with a private bath and two that share a Jack-and-Jill bathroom. A large laundry room with lower cabinets and sink adds convenience, while the spacious flex room facing the lake is perfect for a game room, media space, or home office. The home features 10-foot ceilings on the first floor, 9-foot ceilings upstairs, engineered hardwood flooring throughout, smart fans, fresh exterior paint completed in 2025, and a split three-car garage offering excellent storage for recreational gear, vehicles, or water toys. Located within one of Winter Garden’s premier gated communities, residents enjoy access to a resort-style pool, fitness center, clubhouse, tennis and volleyball courts, dog park, playground, fishing pier, and scenic walking trails. Zoned for top-rated schools and ideally situated near Winter Garden Village, downtown Winter Garden, major highways, and just 15 miles from Orlando’s world-class attractions, this exceptional lakefront home truly offers it all. Now available and ready for immediate occupancy—this is your opportunity to enjoy the ultimate Florida lifestyle. Contact the listing agent to schedule your private showing today.

HIGH & DRY WATERFRONT SINGLE FAMILY, ONE STORY BLOCK HOME! Located on protected waters in Coquina Key providing direct boat access to Tampa Bay, and the Gulf, with no bridges, this 3 bedroom, 2 bath, 1870 sq.ft. home is completely renovated and move-in ready for you to start enjoying life on the water. Hurricane Impact Windows and Doors provide energy efficiency and security from weather elements. Open floor plan, designed for easy flow and furniture placement flexibility. With lots of natural light in the kitchen, stainless steel appliances, an array of cabinet storage, and a breakfast bar, spending time in the kitchen is a delight. The spacious primary bedroom is en-suite with a chic-style primary bath and direct access to the pool. Two additional bedrooms, one of which also has direct access to the pool, and a sleek guest bathroom complete the sleeping quarters. A large 2 car garage, which includes a garage door screen, provides plenty of room for parking and storage. With a new roof, new HVAC system with duct work, new water heater, updated circuit boxes, new front door, and new PVC Lateral drain pipe to the public sewers, there’s nothing left to upgrade. Outside, you’ll find a fully fenced backyard with plenty of room for entertaining around the updated 17,000 gallon pool with a new pool deck, many sitting areas and a retractable awning expanding sun protection. In 2019, the seawall was completely replaced and there’s a composite dock with boat lift, electric, and water. The home presents great curb appeal and a new paver driveway in the front. Conveniently located within minutes to downtown St Pete, USF, 275, and the Gulf Beaches, this home offers the best of all worlds. Call us to schedule your tour!

A rare opportunity to own a beautifully enhanced Ryland Roake II model nestled at the end of a cul-de-sac with commanding views of Johns Lake, a natural pond, and protected conservation. This 5-bedroom, 4-bathroom estate spans nearly 5,000 total square feet and is situated on a premium oversized lot (153' x 161')—fully fenced and designed for privacy, serenity, and stunning sunset views over the water. Step inside and experience refined living with thoughtful upgrades and timeless design choices. The open-concept layout includes an extended gourmet kitchen and family room, expanded 4 feet beyond the standard model, and adorned with custom windows to maximize light and water views. The chef’s kitchen features under-cabinet lighting, sleek finishes, and flows seamlessly into a spacious family area perfect for entertaining. Upstairs boasts hardwood floors, elegant wrought iron railings, and crown molding in all common spaces, while the surround sound system adds ambiance throughout—indoors and outdoors. The owner’s suite is a luxurious retreat with tranquil water views and a frameless-glass walk-in shower. A bedroom and full bath downstairs provide added flexibility for guests or multigenerational living. Enjoy year-round energy savings with Fully Owned Solar Panels, fresh Exterior Paint (2025), Gutters, and Premium Sliding Glass Doors spanning the back of the home—seamlessly blending indoor and outdoor living. Located in Hickory Hammock, one of Winter Garden’s most desirable lakefront communities, residents enjoy resort-style amenities including a gated entry, clubhouse, resort pool, fitness center, tennis and volleyball courts, fishing pier, dog park, and miles of walking trails. Zoned for top-rated schools

Luxury, maintenance free living in VIZCAYA! Orlando’s premier waterfront community, where world-famous attractions and the dazzling culinary delights of "Restaurant Row" are just moments away! This is not just a home; it’s a lifestyle that doesn't disappoint—one that combines resort-style living with the unmatched convenience of Dr. Phillips. Gated, Secure, and Beyond Beautiful—this guard-gated community offers 24-hour security, giving you peace of mind while you indulge in the Florida lifestyle you’ve always dreamed of. Enjoy top-tier amenities including playgrounds, two pristine tennis courts, two sparkling pools, a clubhouse perfect for entertaining, and a fully-equipped fitness center in the master clubhouse. This Home is a Showstopper! No more 2004 here! With over $200K in renovations in 2023, every inch of this home has been transformed into a modern masterpiece from floor to ceiling, with only the finest finishes! Boasting 2,162 sqft, this 2-bedroom, 2-bathroom home has additional Office space with unique, custom bookshelf doors. The open-concept design flows seamlessly with beautiful wood floors, custom plantation shutters, crown molding, 10' ceilings, and sleek 6-inch baseboards that add sophistication at every turn. New AC and ductwork, Hot Water Heater, new lowE double pane sliding glass doors, plumbing, electrical and lighting throughout...the list goes on! The chef-inspired Kitchen features high-end GE Café appliances—perfect for cooking up gourmet meals. The Primary suite is a true retreat with amazing Lake views, and complete with a spa-like en-suite bathroom featuring a custom built-in closet and a rain shower that will transport you to your own private oasis. A stylish Bedroom 2 is perfectly paired with a gorgeous high-end design full bathroom with floor to ceiling tile. Step out onto your private balcony, where the expansive views of Big Sand Lake will take your breath away! Whether you're sipping your morning coffee or winding down after a day of adventure, this serene setting is the perfect place to relax and unwind. Get ready for ultimate convenience with plenty of storage in the hallway closet plus an extra 7'x7' private storage room in the garage—perfect for all your gear, tools, and more. And another great feature...you’ll have your own reserved parking spot in the secure, under-building garage. Top it all off with fantastic schools! This home offers the ultimate combination of luxury, location, and lifestyle. If you’re looking for a place where every detail has been carefully curated and every day feels like a vacation, this is the home for you!

Discover a rare blend of timeless elegance and modern comfort in this beautifully upgraded Standard Pacific “Stamford” model, ideally positioned in the prestigious Johns Lake Pointe community of Winter Garden. This expansive 4-bedroom, 4.5-bath residence offers a seamless 1-story layout with an upstairs bonus retreat featuring a private screened balcony that captures sweeping views of Johns Lake and magical Florida sunsets. From the moment you arrive, refined architectural details and custom finishes set the tone for a truly elevated living experience. The grand foyer makes a stunning first impression with intricate wall trim and a designer mirrored feature, leading into open, light-filled living spaces developed with both style and function in mind. The private office is smartly appointed with custom floor-to-ceiling built-ins and sleek pocket doors—perfect for working from home in comfort. At the heart of the home, the gourmet kitchen caters to culinary excellence, featuring a massive quartz island, premium JennAir appliances, induction cooktop, double convection ovens, built-in microwave, and striking glass accent cabinetry. Open shelving offers both charm and practicality, while the sunlit breakfast nook frames tranquil lake views. A butler’s pantry and a generous walk-in pantry seamlessly connect the kitchen to an elegant dining room with ceiling beams and refined wall detailing—creating an ideal setting for formal gatherings. Tile floors, 10-foot ceilings, wood encased windows, crown molding, and an abundance of natural light enhance the open-concept living areas, while a thoughtfully designed mudroom/drop zone ensures daily functionality. The primary suite is a serene retreat, tucked privately at the rear of the home with breathtaking views of the water. Tray ceilings, a custom-organized walk-in closet, and a spa-caliber bath complete the space, featuring dual vanities, a soaking tub, and an oversized frameless glass shower. Three additional bedrooms are positioned in a split layout for maximum privacy, each with ample closet space and access to well-appointed bathrooms. Upstairs, a spacious bonus room offers endless flexibility—ideal for a media lounge, playroom, or game room. Step out onto the screened-in upper balcony to unwind with panoramic lake views and catch nightly Disney fireworks lighting up the sky. The outdoor space is equally impressive, with an extended paver patio perfect for relaxing with friends and family plus an oversized side yard, perfect for adding a custom pool. With no rear neighbors, you'll enjoy unmatched privacy and an amazing view of the pristine Johns Lake. Set on a quiet cul-de-sac, this property offers exclusive access to resort-style amenities including a clubhouse, oversized pool, fitness center, tennis/pickleball courts, a playground, and a private walking path on Johns Lake. This exceptional location is just minutes from historic Downtown Winter Garden, with its vibrant mix of boutique shopping, gourmet dining, farmers market, and cultural events. You're also near Winter Garden Village, top-rated schools, and major highways—placing you just 15 miles from Orlando’s renowned attractions. Don’t miss the opportunity to own this distinguished lakeview residence—where custom craftsmanship, luxurious upgrades, and an unbeatable location come together to offer one of the finest living experiences in Central Florida.

TROPICAL LAKEFRONT OASIS with GUEST COTTAGE on 1.5 +/- acres - No HOA + 2 Large DETACHED GARAGES(3 Bays) and WORKSHOP. Escape to this beautifully updated 4-bedroom, 3-bath single-story home + Cottage situated on a true lakefront lot along the private shores of Fish Lake. The main home features 2,556 sq ft of living space (5,396 sq ft under roof), thoughtfully designed with natural light, soothing colors, and warm finishes throughout. The open-concept layout flows seamlessly for everyday living and entertaining, while the home’s tasteful updates and abundant windows create a serene, welcoming atmosphere. A fully equipped detached guest cottage includes its own kitchen and offers excellent flexibility for multigenerational living, private guest accommodations, or potential rental income. Outdoors, enjoy lush, Key West-inspired landscaping with mature plumeria, tabebuia, bougainvillea, cypress trees, and natural Florida brush. A charming bench swing hangs in the shade, adding to the peaceful, resort-style ambiance. The property also includes two detached garages — one of which could be converted into additional living or recreational space. The seller already has plans for the conversion. A wooden dock structure is already in place and and is ready to be rebuilt — offering incredible potential for enjoying lakefront living at its best. RECENT UPGRADES: Kitchen Remodel with Quartz countertops. The property has 2 AC units both have been updated(2018 &2023) Kitchen Remodel with Quartz countertops. Metal Roof front half & sky lights of Main Home(2019), Metal Roof on front half(2021) RUN BY PROPANE GAS: Kitchen Stove, Kitchen Water Heater & additional Rinnai Water Tankless Water Heater(2020) & Dryer. Exterior Main Electrical Panel and Pole(2021) Pool Heater(2017) Garage Doors(2018) Asphalt Driveway (2020) New Electrical Main Panel Outside & Pole(2021) The south side of Ames Haven is scheduled to become a Cul De Sac. Tucked away on 1.5~ acres, this property offers the perfect blend of privacy, charm, and convenience — with easy access to the Turnpike, shopping, dining, and major commuter routes.