Osceola Homes with Lake Privileges Frontage

Osceola Homes with Lake Privileges Frontage

Welcome to Osceola County, Florida, a vibrant and picturesque region that perfectly blends natural beauty with modern living. Nestled in the heart of Central Florida, Osceola is renowned for its stunning landscapes, charming communities, and an abundance of recreational opportunities. With a rich tapestry of cultural heritage, the county is home to the bustling city of Kissimmee, offering a unique blend of attractions, dining, and shopping experiences.

One of the standout features of Osceola County is its stunning waterfront properties. Imagine waking up each day to breathtaking views of serene lakes, with homes that boast lake privileges and direct frontage. Whether you’re looking for a cozy retreat or a spacious family home, the real estate options here cater to a variety of lifestyles. Enjoy leisurely afternoons fishing, kayaking, or simply soaking in the sun on your private dock. The lakes not only provide recreational opportunities but also create a peaceful ambiance that enhances your living experience.

Osceola County is also conveniently located near major attractions such as Walt Disney World, Universal Studios, and the beautiful Kissimmee State Park, making it an ideal location for families and adventure seekers alike. With a strong sense of community and a commitment to preserving its natural beauty, Osceola County offers a welcoming environment for those looking to plant roots in Florida.

Explore the charm of Osceola County and discover your dream home with lake privileges today! Embrace a lifestyle filled with adventure, relaxation, and the beauty of nature right at your doorstep.

Newest Osceola Homes with Lake Privileges Frontage

$275,000
Cypress Shores Rep SubDv. ⋅ 34744 Zip Code
This property is a CASH only LAND only sale. The home is uninhabitable. Located on a canal with direct access to Lake Toho. The neighborhood also has a private boat ramp. You can build your dream lake house here and save money on impact fees. During specific Holidays you have views of the city run Fireworks from your backyard.

740 Shore Drive, Kissimmee
$275,000
3 Beds ⋅ 2 Baths ⋅ Cypress Shores Rep SubDv. ⋅ 34744 Zip Code
This property is a CASH only LAND only sale. The home is uninhabitable. Located on a canal with direct access to Lake Toho. The neighborhood also has a private boat ramp. You can build your dream lake house here and save money on impact fees. During specific Holidays you have views of the city run Fireworks from your backyard.

740 Shore Drive, Kissimmee
$1,375,000
6 Beds ⋅ 5 Baths ⋅ Waterside Vista SubDv. ⋅ 34771 Zip Code
Virtually Staged. Mediterranean Elegance Meets Waterfront Luxury in the Exclusive Gated Community of Waterside Vista. Experience luxury, privacy, and convenience in this stunning Mediterranean-inspired estate nestled within the exclusive gated enclave of a private boating community of only 24 custom residences. This one-of-a-kind property features a residential elevator, large home theater, breathtaking canal views, direct access to the Chain of Lakes, a heated saltwater pool, a rare five-car split garage, and an extended driveway accommodating up to 11 vehicles, perfect for your boats, cars, RVs, and all your recreational toys. Enjoy the benefit of lower St. Cloud taxes while being adjacent to Lake Nona, just 10 minutes from Lake Nona Medical City, highway 417 exit, world-class dining, shopping, and only 20 minutes from Orlando International Airport. Situated on a .64-acre waterfront homesite, this 5,193-square-foot estate offers 6 bedrooms, 5 bathrooms, and three versatile flex rooms ideal for a home office, gym, movie theater, playroom, or additional guest space. Enjoy breathtaking canal views with direct access to Fells Cove, East Lake Tohopekaliga, and the Chain of Lakes. The deep-water canal offers the opportunity to build your own private dock and enjoy the ultimate Florida boating lifestyle. From the moment you arrive, the home's striking Mediterranean architecture commands attention. A dramatic two-story turreted entrance, reminiscent of a castle, welcomes you into a spectacular 24-foot foyer with an elegant Juliet balcony. The home's impressive curb appeal is further enhanced by an extended driveway that comfortably accommodates accommodates up to 11 vehicles and is complemented by a rare five-car split garage, perfect for car enthusiasts, boat owners, or multigenerational living. The garage also features both a Tesla charger and an EVBox charging station. The open-concept floor plan is designed for entertaining and everyday living, featuring a chef's kitchen with an oversized granite island, upgraded countertops, stainless steel appliances, gas cooktop, and separate butler's pantry. An oversized laundry room offers abundant cabinetry, while thoughtful accessibility features including a residential elevator and front entry ramp provide comfort and convenience. The first-floor owner's suite is a private retreat featuring a custom walk-in closet with built-in organizers. A second first-floor bedroom and full bath are ideal for guests or multigenerational living. Upstairs offers a spacious living room with wet bar, a dedicated theater room, and four oversized bedrooms, including one with its own Juliet balcony. Step onto the second-floor balcony and take in beautiful canal views. Outdoor living shines with a heated saltwater pool, recently replaced pool motor, and a brand-new screened enclosure. More than 84 solar panels will convey with the home to help minimize electric costs, while a whole-home water treatment system enhances everyday comfort and efficiency. This exceptional home combines luxury waterfront living, private boating access, energy-efficient upgrades, accessibility features, abundant parking, and an unbeatable location next to Lake Nona. RSVP for the upcoming viewing event.

5229 Waterside Vista Lane, St Cloud
$649,000
5 Beds ⋅ 4 Baths ⋅ Bellalago SubDv. ⋅ 34746 Zip Code
Virtually Staged. Stunning LAKEFRONT estate on an oversized .44-acre premium lot in the resort-style, guard-gated community of Bellalago. Nestled directly along the shores of Lake Tohopekaliga on the scenic Kissimmee Chain of Lakes. This home has "WOW" factor and offers exceptional waterfront living and access to one of Central Florida’s most iconic lake systems. This beautifully maintained home offers a multi-generational floor plan featuring 5-bedrooms, 4-bathrooms as well as a dedicated office and offers high end upgrades throughout. The first-floor features 4 bedrooms, 3 bathrooms, and an office, while the spacious upstairs bonus room serves as a 5th bedroom with an en-suite full bath. Gorgeous wood flooring, a fully fenced backyard, and an expansive screened patio with a summer kitchen and jacuzzi. This home is perfect for entertaining. The sellers have replaced all bedroom carpeting, installed engineered wood on the stairs, and refreshed the handrails with new spindles for a refined look. The kitchen impresses with newly upgraded granite countertops, a stylish backsplash, and added cabinetry including a 9'6"×24" white shaker cabinet. Lighting has been modernized with new pendants and a chandelier, complemented by a new sink and spray faucet. Additional updates include fresh interior paint, a charming barn door in the laundry room, premium wood pantry shelving, and custom closet organizers, including a redesigned primary closet with wood shelving and rods for enhanced storage. Bellalago offers a true resort-style experience along the scenic shores of Lake Toho, known for its world-class bass fishing. Community amenities include multiple pools, fitness center, lakeside clubhouses, on-site dining, tennis and basketball courts, walking trails, and a private boat ramp with direct lake access. Families enjoy the water park and zero-entry pool, while residents appreciate 24-hour security. CABLE AND INTERNET ARE INCLUDED! This home is a must see!

1511 Gateway Lane, Kissimmee
$600,000
Mccools Add To Kissimmee Park SubDv. ⋅ 34772 Zip Code
WATERFRONT INVESTMENT & DEVELOPMENT OPPORTUNITY ON WEST LAKE TOHO! Approximately 1.89 acres with freshwater canal access to Lake Tohopekaliga, offering water views, lake privileges and a unique opportunity in the rapidly growing St. Cloud market. An adjoining approximately 1.83-acre waterfront parcel may also be available, creating the potential to assemble approximately 3.72 waterfront acres. With utilities available and commercial or mixed-use possibilities subject to county approval, this property offers exciting potential for an investor, developer or owner-user. Conveniently located near major roadways, shopping, dining and the continued growth of the St. Cloud area. Buyer to independently verify zoning, land use, development potential and permitted uses with the appropriate county authorities.

Seaman Avenue, St Cloud
$450,000
4 Beds ⋅ 2 Baths ⋅ Bellalago Ph 4k SubDv. ⋅ 34746 Zip Code
Welcome to 3801 Bowfin Trail, Kissimmee, FL 34746 — a beautifully maintained WATERFRONT ACCESS HOME located in the award-winning resort-style community of Bellalago. Positioned on a premium lot with only one direct neighbor, this exceptional one-story residence offers 3 bedrooms, 2 bathrooms, a dedicated den/study or 4th bedroom, and a spacious 3-car garage. Nestled on a quiet corner homesite, the property backs directly to waterfront access leading to Lake Tohopekaliga, creating a peaceful setting with added privacy and beautiful natural surroundings. Designed with both comfort and functionality in mind, the open-concept floor plan seamlessly connects the living, dining, and kitchen areas, making it ideal for entertaining or everyday living. Large windows fill the home with natural light while the covered lanai provides the perfect space to relax and enjoy Florida's outdoor lifestyle. This home has been lightly lived in as a secondary residence, occupied approximately 6–8 weeks per year, resulting in minimal wear and exceptional overall condition. For added peace of mind, a NEW A/C SYSTEM was installed approximately two months ago. When built, the owners selected numerous upgrades, including: • Upgraded cabinetry in the kitchen, bathrooms, and laundry room • Laundry room cabinets • Upgraded tile flooring throughout the main living areas, bathrooms • Interior paint upgrades • Upgraded master shower and soaking tub • Upgraded sinks and plumbing fixtures • Upgraded front entry door • Window blinds throughout • Security system installation • Added gutters • Over-cabinet electrical outlets • Covered lanai and paver driveway Beyond the home itself, Bellalago offers one of the most impressive lifestyle experiences in Central Florida. This master-planned waterfront community showcases stunning Spanish Mediterranean architecture, barrel tile roofs, lush landscaping, scenic water views, and resort-inspired amenities throughout. Residents enjoy: • 24-hour manned gated security • Direct access to Lake Tohopekaliga via private boat ramp and lakefront docks • Three resort-style swimming pools • Two state-of-the-art fitness centers • Tennis, pickleball and basketball courts • Walking and biking trails • Fishing pier and waterfront recreation areas • Dog parks and playgrounds • Daily community activities and fitness classes • On-site poolside restaurant and gathering spaces • Cable TV included through the HOA Whether you're looking for a full-time residence, seasonal retreat, or waterfront lifestyle without the waterfront price tag, 3801 Bowfin Trail offers an incredible opportunity to enjoy one of Central Florida's premier lakefront communities. Come experience the Bellalago lifestyle and discover why so many residents proudly call this community home.

3801 Bowfin Trail, Kissimmee
$415,000
East Lake Reserve At Narcoossee Unit 3 SubDv. ⋅ 34771 Zip Code
Increased value now that two lots listed $499K and $475K pending same lot as sellers lot !Don’t miss the chance to own one of the few remaining buildable lots on East Lake Toho!Bring your vision to life on this beautiful vacant waterfront lot in one of St. Cloud’s sought-after GATED communities. Just shy of an acre, this property offers the perfect opportunity to build your dream home ! Enjoy peaceful water views, your own private dock, and breathtaking sunsets right from your future backyard. Whether you’re looking to build a full-time residence, second home or a relaxing retreat, this rare lakefront lot offers the space, scenery, and lifestyle you’ve been searching for Discover the opportunity to build your dream waterfront estate on nearly .8 acres along the shores of East Lake Toho inside one of Osceola County’s most sought-after gated communities. Unlike newer subdivisions near Lake Nona, this rare homesite offers something increasingly difficult to find — meaningful acreage, direct waterfront access, mature natural surroundings, and lasting privacy. Positioned to capture breathtaking western-facing sunset views, the property overlooks East Lake Toho with evening reflections stretching across the water, creating the perfect backdrop for future outdoor living and architectural design. A mature oak hammock anchors the rear of the property, offering a natural privacy buffer and an established setting that cleared lots simply cannot replicate. The recent value repositioning creates an exceptional advantage for the next owner, allowing additional flexibility to immediately incorporate luxury features into the build such as a private dock, resort-style pool, summer kitchen, expansive outdoor entertaining space, or custom lakefront design elements from the very beginning. Despite the peaceful waterfront setting, the location remains highly connected — just minutes from Lake Nona Medical City, premier dining, shopping, major highways, and Orlando International Airport. As buildable waterfront inventory near Lake Nona continues to disappear, opportunities like this become increasingly rare. This is more than vacant land — it is the foundation for a lifestyle that cannot easily be replicated. More land. More water. More privacy. A smarter entry point into luxury waterfront living. Schedule your private tour today to experience the scale, setting, and sunset views in person.

4810 Calasans Avenue, St Cloud
$429,900
3 Beds ⋅ 2 Baths ⋅ Maple Terrace SubDv. ⋅ 34771 Zip Code
MOVE-IN READY! UNIQUE LAKE-ACCESS OPPORTUNITY! Welcome to 2234 Maple Ter, a charming 3-bedroom, 2-bath single-family home in the Maple Terrace area of St. Cloud. Built in 1979 and offering approximately 1,504 heated square feet, this one-story home sits on a spacious 0.40-acre lot in a quiet established neighborhood near Alligator Lake. The property features a private screened pool, in-ground spa, covered carport, mature landscaping, and a peaceful outdoor setting with nearby canal and lake views. The owner has directly stated that the home offers front-door access to Alligator Lake and the connected Chain of Lakes, plus shared ownership interest in a private canal with private boat dock and direct lake access. Inside, the home offers a functional layout with separate living and dining areas, solid-surface kitchen counters, ceiling fans, window treatments, and accessibility-friendly bathroom features including a walk-in tub and shower grab bars. Recent owner-reported updates include a new roof in 2023, new pool screen in 2022, new pool pump in 2025, pool tile and resurfacing in 2026, A/C system serviced in 2025, well pump serviced in 2026, whole-home generator with 100-gallon rented propane tank, and transferable Massey termite bond. Carpet has been removed and not replaced, and seller is offering up to $20,000 in buyer concessions, which may be used toward flooring, repairs, closing costs, prepaid items, or other allowable costs. Conveniently located near US-192, Lake Nona area access, shopping, dining, schools, and major Central Florida roadways. IMPORTANT NOTE TO BUYER AGENT: Limited-service listing. Please see Realtor Only Remarks or Showingtime Instructions on StellarMLS for showing and offer instructions.

2234 W Maple Terrace, St Cloud
$1,290,000
4 Beds ⋅ 4 Baths ⋅ Oakwood Shores SubDv. ⋅ 34771 Zip Code
Experience the best of Central Florida lakefront living on Trout Lake, part of the Alligator Chain of Lakes, with this exceptional custom-built home located at 6805 Bass Highway in St. Cloud. Offering a rare combination of luxury, privacy, and investment potential, this stunning waterfront property is perfectly suited as a primary residence, second home, or vacation rental — all with NO HOA restrictions. Ideally positioned within one hour of Walt Disney World Resort and Universal Orlando Resort, Orlando’s world-famous attractions, and Florida’s beautiful east coast beaches, and just 30 minutes from Lake Nona and the Orlando International Airport this property offers the perfect balance of peaceful lakefront living and convenient access to everything Central Florida has to offer. Built in 2014, this impressive 3,535-square-foot custom home features 4 bedrooms, 4 bathrooms, and thoughtfully designed living spaces filled with high-end upgrades and custom details throughout. From the moment you enter, you’ll appreciate the upgraded cabinetry, premium countertops, designer fixtures, upgraded flooring, and beautifully finished stained concrete surfaces that create a warm yet modern lakefront aesthetic. The spacious chef’s kitchen was designed with both functionality and entertaining in mind, featuring extensive custom cabinetry and an expansive hidden walk-in pantry that provides exceptional storage and organization. Throughout the home, you’ll find numerous built-in storage areas, window seats in most bedrooms, and carefully crafted details that add both charm and practicality. The primary suite offers a luxurious private retreat complete with a dedicated vanity/glam room and generous storage solutions. Upstairs, a versatile bonus room provides endless possibilities and can easily function as a home office, media room, playroom, or be converted into an additional bedroom. Additional flexible living spaces include a separate air-conditioned room ideal for a home gym, hobby room, or flex space, along with a dedicated air-conditioned laundry room conveniently located off the garage. The property also includes multiple outdoor storage sheds, offering even more room for tools, lake toys, and equipment. Set on 160 feet of fully cleared lakefront, the property showcases breathtaking water views, a private sand beach area, and direct access to the highly sought-after Alligator Lake Chain — a connected chain of five lakes known for boating, fishing, and watersports. The outdoor amenities are truly exceptional. A brand-new 110-foot dock features a covered metal roof, electric boat lift, lakeside sitting area, and propane fire pit, creating the ultimate waterfront gathering space. The expansive 600-square-foot fully enclosed screened outdoor kitchen overlooks the lake and offers year-round enjoyment for entertaining family and guests. An additional lakeside fire pit area further enhances the unmatched outdoor lifestyle this property provides. Major recent upgrades include a roof and exterior paint both completed just 2 years ago, adding long-term value and peace of mind. This is a rare opportunity to own a true Central Florida lakefront lifestyle property with freedom, luxury, space, and exceptional vacation rental potential!

6805 Bass Highway, St Cloud
$1,250,000
5 Beds ⋅ 3 Baths ⋅ S L & I C SubDv. ⋅ 34772 Zip Code
Welcome to an extraordinary opportunity at 4901 Manor House Lane in beautiful St. Cloud — located in one of Central Florida’s rare private fly-in communities! This stunning 4+ acre estate offers a lifestyle that is nearly impossible to find anywhere else in Florida, combining both private runway access and lakefront living in one incredible property. Adjoining the community runway, this one-of-a-kind property is perfect for aviation enthusiasts and those seeking privacy, luxury, and adventure. Enjoy approximately 350 feet of deeded water frontage with direct access to Lake Gentry and the highly sought-after Southern Chain of Lakes in Osceola County, creating endless opportunities for boating, fishing, and waterfront recreation. The beautifully designed custom home features 5 spacious bedrooms and 3 full bathrooms with exceptional craftsmanship and upscale finishes throughout. Inside, you’ll find custom upgraded countertops, cabinetry, upgraded tile flooring throughout entire home, fixtures, and thoughtfully designed living spaces ideal for both entertaining and everyday comfort. Step outside to your own private resort-style retreat featuring a stunning outdoor living and kitchen area, perfect for hosting gatherings year-round, along with a built-in swimming pool surrounded by the peaceful beauty of the property. Additional features include a spacious 3-car garage and a private detached guest house complete with 1 bedroom, 1 bathroom, and a mini kitchen — ideal for guests, extended family, or additional income potential. Conveniently located just 30 minutes south of Lake Nona Medical City and only 30 minutes from Florida’s beautiful East Coast beaches, this property offers the perfect balance of luxury, convenience, and recreation. Properties like this rarely become available — schedule your private showing today before this exceptional estate is gone!

4901 Manor House Lane, St Cloud
$375,000
1 Beds ⋅ 2 Baths ⋅ Shelter Cove SubDv. ⋅ 34771 Zip Code
This is everything you have been dreaming of! Check out this 1bedroom 1 bathroom lakefront on the Alligator Chain of Lakes with extensive upgrades and superior construction. Tray ceilings, crown molding, full baseboards, vinyl plank flooring, quartz counters in kitchen and bath with custom backsplash, large stainless sink, solid wood cabinetry, walk-in glass shower, and ceiling fans. Stainless appliance package includes glass-top range, oven, microwave, dishwasher, and upgraded refrigerator with ice maker. Garbage disposal and Culligan RO filtration system. Built with 2x6 shear walls, Hardie board concrete siding to the base, metal roof, double-pane windows, double cross tie-down system anchored into concrete, and upgraded 200-amp service.Outdoor living is taken to the next level with a composite dock and decking leading to a custom-built tiki bar, constructed on pilings driven to the lake bottom and topped with a standing seam metal roof. The tiki area is fully equipped with 50-amp electric, water, refrigeration, and a bar setup—perfect for entertaining. Remote-controlled screens provide comfort and shade while you enjoy the view. The composite seawall is reinforced with stainless steel tie-backs and durable filter fabric, offering both beauty and long-term stability. Boat ramp is located just seconds away. Excellent waterfront location for boating, fishing, and skiing. Ideal for primary residence or weekend retreat. Don't miss this opportunity to own your own private oasis. Home is located close to beaches, resturants, hospitals loca shopping but still maintains a privacy with its own community.

1315 Pine Island Dr N, St Cloud
$495,900
4 Beds ⋅ 3 Baths ⋅ Bellalago Ph 4k SubDv. ⋅ 34746 Zip Code
Beautifully remodeled waterfront home in Bellalago with private boat dock and ramp, offering direct access to the Chain of Lakes. Enjoy stunning water views from the open-concept living space and screened Florida room. Features include real hardwood flooring throughout, a modern kitchen with center island, quartz countertops, full-height cabinetry with crown molding, and built-in appliances. Additional highlights: • Walk-in wine cellar with racks, dual coolers & glass barn door • Utility room with porcelain sink and ample storage • First-floor walk-out balcony • LED recessed lighting throughout Professionally designed interior with high-end finishes throughout. A must-see waterfront property.

3879 Shoreside Drive, Kissimmee
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