Waterfront Homes for Sale in Orange County, FL

7 Beds ⋅ 14 Baths ⋅ N/A SubDv. ⋅ 34786 Zip Code

Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multiple buildings spanning 51,000 square feet of space including an expansive 20,333 square-foot Georgian-style Plantation mansion that is a showplace residence with generous luxurious spaces, classic elegance, and the ultimate in security and serenity. The walled entry opens to a grand foyer with a floating mahogany staircase, marble floors, paneled walls, and Murano chandeliers. An art gallery leads to a spacious living room featuring rich mahogany millwork and expansive lake vistas. Gourmet kitchen: salamander, dual double convection ovens, commercial icemaker, full-size refrigerator, and freezer. The main level includes one of two owners' suites, plus a library-lounge or a possible sixth bedroom. Dual staircases or a Thyssenkrupp elevator provide access to the upper level, which features four-bedroom suites, including the primary retreat. An 85-foot parlor with 20-foot ceilings, built-in bookshelves, and a wet bar provide a dramatic entertaining space. Screened porch captures southern lake views and Disney fireworks. Breezeway connects to a 5,600 SF rustic lodge with a bar, catering kitchen, entertainment hall, and locker facilities. Outdoor amenities: Junior Olympic pool, spa, decorative fountain, architectural lighting, direct lake access. The vast and open water location offers an ideal space for seaplane arrivals and departures. Additional structures include a 4,000 SF paneled garage with 20-foot ceilings, an office, and a guest apartment; a 3,800 SF storage building; three separate garages accommodating motor coach and car collection; and staff quarters with a private courtyard. A rare fusion of Southern grandeur, lakefront serenity, and equestrian potential—without any interference of an HOA. Truly a legacy compound crafted for those who demand the extraordinary.

9508 Windy Ridge Road, Windermere

$27,000,000

7 Beds ⋅ 10 Baths ⋅ Na SubDv. ⋅ 34786 Zip Code

A rare legacy estate of extraordinary scale and architectural significance, this magnificent lakefront compound spans over 22,000 square feet across more than 11 private acres with over 440 feet of pristine frontage on Cypress Lake. Masterfully designed to deliver the ultimate blend of grandeur, privacy, and resort-inspired living, the residence is statement of uncompromising luxury. Beyond the gated entrance, a sweeping motor court and dramatic porte-cochère introduce the home’s commanding Mediterranean-inspired architecture, where turreted wings, natural stone detailing, and elegant arched windows create an unforgettable arrival experience. Inside, a breathtaking 28-foot grand foyer unfolds beneath soaring ceilings, anchored by a spectacular double staircase with intricate custom ironwork that evokes the elegance of a world-class villa. Flooded with natural light through towering arched windows, the space immediately establishes the scale and sophistication that define the estate. Designed for intimate living and large-scale entertaining, the interiors blend timeless craftsmanship with modern refinement. The gourmet chef’s kitchen is a showpiece of its own, featuring custom wood cabinetry, expansive stone countertops, professional-grade appliances, a dramatic custom range hood, oversized center island, hidden pantry and richly detailed ceiling treatments that elevate the space into a culinary centerpiece. Adjacent gathering areas showcase exposed wood beams, designer lighting and seamless indoor-outdoor connectivity, creating warm yet grand living environments ideal for entertaining on any scale. Every amenity within the residence has been thoughtfully curated to rival the finest luxury resorts. Highlights include a state-of-the-art theater, golf simulator, multiple game rooms, an expansive wine room, private elevator, smart home automation system and a fully equipped fitness center. Elegant fireplaces and sophisticated entertaining spaces add warmth and intimacy throughout the home. A private guest wing with two bedrooms, its own living room, and separate entrance offers luxurious accommodations for extended family, guests or staff. The outdoor experience is nothing short of spectacular. The rear elevation unfolds around a breathtaking 125,000-gallon resort-style pool complete with cascading waterfalls, bordered by natural stones, a water slide, diving board and expansive terraces that rival five-star destinations. At twilight, the towering palms and illuminated architecture reflect across the shimmering water, creating a setting reminiscent of an exclusive private resort with intimate lounge settings that invite grand entertaining and quiet moments of retreat. For the automotive enthusiast, the estate includes a 10-car garage equipped with two vehicle lifts. Recreational amenities continue across the grounds with a private basketball court, boat dock and private community boat ramp, which provide effortless access to the desired Butler Chain of Lakes for world-class boating and waterfront living. Surrounded by expansive lawns, mature landscaping and unmatched privacy, this extraordinary residence represents a once-in-a-generation opportunity to own a waterfront legacy estate, a property designed not only to impress, but to endure for generations to come.

5603 Marleon Drive, Windermere

$25,000,000

32712 Zip Code

Growing Area. Opportunity abounds. Sixty acres contiguous. Road Frontage in developing area. Buyer to verify all dimensions.

4625-4651 W Kelly Park Road, Apopka

$20,000,000

6 Beds ⋅ 9 Baths ⋅ Lake Nona Estates SubDv. ⋅ 32827 Zip Code

Pre-Construction. To be built. A once-in-a-generation waterfront estate, exclusively designed and built by Mrcela Custom Homes, setting a new benchmark for luxury living in Central Florida. This extraordinary showcase residence seamlessly combines timeless architecture, cutting-edge engineering, and world-class resort amenities into one remarkable estate. Constructed using the patented Fortex cast-in-place concrete wall system, the home is engineered for exceptional structural integrity, fire resistance, storm resilience, energy efficiency, and long-term durability, establishing a new standard for luxury residential construction. As the first Fortex showcase residence, this home represents the future of luxury homebuilding. Designed for both grand entertaining and everyday living, the estate features an underground collector garage, resort-style wellness spa, state-of-the-art movie theater, private championship tennis court, expansive indoor and outdoor living spaces, breathtaking waterfront views, and a fully reinforced concrete safe room. This space is engineered to provide exceptional security and resilience, making it ideal as a storm shelter, secure storage for valuables, or a private retreat. The safe room is constructed entirely of reinforced concrete and has been thoughtfully integrated into the home's luxury design, offering peace of mind without compromising functionality or aesthetics. Every detail has been thoughtfully designed to create an unmatched lifestyle where innovation, luxury, privacy, and security come together in one extraordinary residence. More than a luxury home, this is a legacy estate built to standards rarely seen in residential construction. Price includes a membership initiation fee to Lake Nona Golf & Country Club, subject to application and acceptance. Members of Lake Nona Golf & Country Club enjoy a wealth of amenities, including a premier championship golf course, 40,000-square-foot Clubhouse with an 18-room Lodge, a Bath & Racquet Club with tennis facilities, a resort-style, lakeside pool, year-round children’s programming, 24-hour gated security and outstanding water-based recreation on a trio of waterways.

10084 Tavistock Rd, Orlando

$20,000,000

28 Beds ⋅ 10 Baths ⋅ James B Parramores Add SubDv. ⋅ 32805 Zip Code

Rare opportunity to acquire a diverse, income-producing portfolio in the rapidly evolving Parramore area of Orlando. This offering includes 32 properties totaling 103 units, featuring a strong mix of asset types: duplexes, quadplexes, a 6-plex, 8-plex, and 10-plex, along with two single-family homes. The portfolio offers immediate cash flow, with the majority of units already leased and generating consistent rental income. Unit configurations range from studios to 3-bedroom units, providing broad tenant appeal and diversified income streams. Strategically located in the heart of Orlando’s urban core, these properties are within walking distance to the Kia Center, Inter&Co Stadium, and Camping World Stadium—major entertainment and sports hubs that continue to drive strong rental demand and neighborhood growth. This portfolio positions investors to benefit from ongoing redevelopment, population growth, and long-term appreciation in the Parramore submarket. With scale, density, and strong rental demand, this is an ideal opportunity for investors seeking both stable returns and future upside potential. Whether you’re looking to expand your existing holdings or establish a significant footprint in one of Orlando’s most promising areas, this portfolio delivers on all fronts. Don’t miss this chance to secure a high-performing, large-scale investment in a prime Central Florida location.

621 W South Street, Orlando

$18,900,000

Hamlin Southwest SubDv. ⋅ 34787 Zip Code

Price Improvement on this Rare Triple-Net Investment Opportunity: Flagship Leisure Anchor (ground lease) in America’s 2nd Best-Selling Community – Hamlin/Horizon West. Own a premier 61,844-square-foot Class A commercial asset situated in the heart of the 1,200-acre Hamlin master-planned development. This investment offers an exceptional arbitrage opportunity for a savvy buyer, pairing a high-performance corporate tenant with a long-term, secure ground lease in one of the nation's fastest-growing corridors. The purchase of the 5758 Hamlin Groves Trail building is a bet on a "flourishing" community that has transformed from raw land in 2011 to a 1,200-acre connected powerhouse in 2022. With thousands of homes still planned for the five villages of Horizon West and significant infrastructure projects underway, the area's commercial vacancy remains low while provider demand continues to escalate. This asset is perfectly positioned to capture the long-term value of Central Florida’s most successful "Live, Work, Play" destination. Offering Memorandum and NDA available for interested investors.

5758 Hamlin Groves Trail, Winter Garden

$17,250,000

7 Beds ⋅ 9 Baths ⋅ Metcalf Park Rep SubDv. ⋅ 34786 Zip Code

Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double residence guest house, and a majestic and stunning grand mansion with additional guest retreat, all spanning more than 14,444 square feet of living space and 11 bedrooms across both residences. Welcome to this one-of-a-kind haven of privacy and prominence showcasing the best of Central Florida living. Set on a rare 3.75 acres commanding enviable views on the northern shore of Lake Butler, every detail has been thoughtfully designed to celebrate both refinement and tranquility. The impressive palatial main residence boasts 10,649 square feet of living space with 6 bedrooms plus a one-bedroom guest retreat and an array of curated spaces. The Spanish Eclectic interior fuses classic craftsmanship with modern sophistication, creating an inviting and awe-inspiring escape from the ordinary. On entrance be greeted by sweeping floor to ceiling windows to allow breathtaking water vistas, double-sided gas fireplace, a grand colonnade hallway, and architectural details throughout. The gourmet chef’s kitchen features top of the line appliances, gas range with multiple burners, ovens, island with second sink, and walk-in pantry. A sports bar games room and showstopping home theater provide an abundance of entertaining options. Other notable amenities include a Castilian wine cellar, bay windows, two wet bars, private salon, elevator, gym, steam room and sauna. Outdoors, a generous summer kitchen with automatic roller screens provide an outdoor oasis for al fresco dining, cooking, or relaxing. The zero-entry infinity pool and vast resort decking provide a breathtaking vantage point for panoramic views of Lake Butler’s radiant sunsets, while the shaded Zen garden and white sandy beach offer a tranquil retreat for quiet reflection. With many distinct outdoor venues, serenity is never far away. The estate’s private island, accessed by an electric drawbridge, and a boat ramp provide unmatched exclusivity to Lake Butler and the world-famous Butler Chain of Lakes. The two-story detached guest house offers 3,795 sq feet of living space across two, 2-bedroom apartment homes, each with kitchens, laundry rooms, an elevator, and attached two-car garage. Built for a large multi-generational family, guest quarters, or on-site caretakers, the possibilities are endless. Truly a picture-perfect unmistakable showplace offering the very best for the most discriminating buyer.

11900 Lake Butler Boulevard, Windermere

$16,000,000

Orangewood Neighborhood-2 SubDv. ⋅ 32821 Zip Code

Exceptional 8.72 +/- Acre property located on International Drive at the intersection with Westwood Boulevard. Fully entitled with PD zoning allowing for tourist commercial uses up to 103,000 Sq. Ft and heights up to 200 feet for hotel and 60 feet retail. Site has access to public sewer and water and excellent visibility.

11990 International Drive, Orlando

$16,000,000

34787 Zip Code

This property is made up of 4 parcels totaling 99.86 acres and offers a very unique opportunity. Property located in “Village I” of Horizon West Master Development Plan created by Orange County to proactively manage the considerable population and housing growth in southwest orange County. A total area of 28,000 acres was zoned appropriately and 45,000 households, 6 villages, a Town Center, Golf Courses and more expected at completion. Property has 424’ feet of frontage. 1 miles west of Expressway 429. Area has seen a increase in land value. Trend should continue as residential and commercial development plans go up. Minutes from Windermere, Downtown Orlando and Disney.

17802 Old Ymca Road, Winter Garden

$15,900,000

7 Beds ⋅ 9 Baths ⋅ Keene's Point SubDv. ⋅ 34786 Zip Code

Experience luxury lakefront living on a grand scale in this exquisite estate on Lake Tibet, part of the pristine Butler Chain of Lakes in Windermere. This custom-built masterpiece by Goehring & Morgan is inspired by Andrea Palladio, one of the most influential architects in history, celebrated for his elegant country houses and villas. The design draws inspiration from the diverse regions of Italy, with the finest imported materials hand-selected to ensure authenticity. Every finish and detail was thoughtfully curated, showcasing refined craftsmanship, exquisite design elements and seamless indoor-outdoor living enhanced by stunning water views. Offering 14,068 square feet of living space with an elevator on more than four acres, this remarkable residence enjoys one of the most breathtaking lake views in the area. Thoughtfully designed with Palladian principles, the rear elevation is every bit as impressive as the front, maximizing the beauty of its exceptional waterfront setting. With six bedrooms and eight-and-a-half baths plus guest house, this home offers every luxury amenity imaginable. The floor plan includes formal living and dining rooms, an open-concept kitchen and family room that flow effortlessly into the outdoor living spaces, a climate-controlled wine room, an office, a library, two bonus rooms, a fitness room and a private attached guest suite. The backyard retreat evokes the feeling of Lake Como, with picturesque sightlines, expansive lake views and covered outdoor living areas featuring fireplaces that surround the resort-style pool. Mature landscaping provides exceptional privacy while enhancing the ambiance of this extraordinary outdoor oasis. Artistry is evident throughout every space, highlighted by exposed wood beams with hand-painted details, frescoed ceilings, Old World tumbled brick floors and ceilings, inlaid marble and wood accents, barrel-vaulted ceilings, Venetian plaster finishes and countless other custom architectural elements. Within the guard-gated community of Keene's Pointe, this estate enjoys access to an exceptional lifestyle. Lake Tibet is one of the largest lakes on the Butler Chain, offering privacy and connectivity through the navigable canal system. The Butler Chain of Lakes, also known as the Windermere Chain of Lakes, consists of 13 interconnected lakes encompassing more than 5,000 acres of spring-fed water. Residents of Keene's Pointe enjoy access to the renowned Golden Bear Club, featuring a 250-acre Jack Nicklaus Signature Golf Course, a resort-style pool, tennis courts, a fitness center, multiple playgrounds and a clubhouse for private events. Combining small-town charm with unparalleled convenience, Windermere is just minutes from downtown Orlando and offers easy access to fine dining, world-class shopping, championship golf courses, top-rated schools, international and private airports, and world-famous theme parks. The Butler Chain of Lakes spans more than 4,900 acres of crystal-clear, spring-fed water and is renowned for its pristine sand bottoms, exceptional water quality and designation as an "Outstanding Florida Water."

6119 Grosvenor Shore Drive, Windermere

$15,500,000

10 Beds ⋅ 17 Baths ⋅ Chaine Du Lac SubDv. ⋅ 34786 Zip Code

Commanding a rare 2.75-acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a meticulous, ground-up transformation, the residence showcases a level of craftsmanship, design integrity, and finish quality that is simply unrivaled in Central Florida. From the moment you arrive, the estate announces itself with undeniable presence. Grand entry doors open to a breathtaking interior defined by soaring 30-foot ceilings, dramatic architectural volumes, and a sleek, contemporary aesthetic softened by warm, bespoke materials. Walls of glass frame panoramic lake views, creating a seamless dialogue between indoor elegance and the natural beauty beyond. Designed for both refined living and grand-scale entertaining, the interior amenities rival those of a world-class resort. Highlights include a private spa sanctuary, fully equipped fitness center, state-of-the-art home theater, and an expansive game and entertainment lounge. The chef’s kitchen is a showpiece, thoughtfully designed for culinary excellence, intimate gatherings, or catered events, anchored by Wolf & Miele appliances, custom cabinetry, and flawless detailing throughout. The primary suite is nothing short of spectacular: a serene retreat offering commanding lake views, spa-inspired bath accommodations, and an atmosphere of complete privacy and indulgence. Every element of the home is enhanced by cutting-edge smart home technology, delivering effortless control, comfort, and security. A thoughtfully designed separate guest wing allows for exceptional flexibility, making the estate equally suited as a private family residence, an entertainer’s dream, or an inspired corporate retreat. Outdoors, the property unfolds into a private resort oasis. Impeccably manicured grounds lead to a private boat dock on the Butler Chain, a hidden garden retreat, and a stunning resort-style pool ideal for both relaxation and large-scale gatherings. Additional features include a putting green, a nine-car garage, and a detached guest house complete with its own kitchen, living area, and bedroom, perfect for extended guests or staff accommodations. A rare opportunity to own one of Central Florida’s most iconic and impressive lakefront compounds, where every detail has been elevated to the highest standard.

12488 Park Avenue, Windermere

$15,500,000

4 Beds ⋅ 5 Baths ⋅ Golden Oak Florian Park Condominium SubDv. ⋅ 32836 Zip Code

A new luxury Four Seasons Private Residences opportunity is now available at Golden Oak at Walt Disney World® Resort. The proposed project by HHR FSO LAND LLC will feature a collection of nine attached boutique homes and 31 luxe residences, including five stunning multi-level penthouses, all within a single, elevated residential address. Designed for hotel-inspired living at a magical address, these residences provide an elevated lifestyle enhanced by Four Seasons’ renowned service. Penthouses provide breathtaking views and spacious designs. The Crestline plan features 6,725 square feet and soaring two-story living room with grand staircase leading the second level. Stunning living space with custom-built shelving featuring natural stone and warm, wooden accents. Gourmet kitchen with frameless contemporary cabinetry, a large center prep island, a spacious pantry with built-in cabinetry and refrigerated wine storage. The luxurious dining room is perfect for gracious gatherings. Premium finishes like Wolf, Subzero, and Cove appliances enhance the gourmet kitchens, while other features include two flex spaces, in-unit lift, thoughtful balcony placement, and modern-transitional design. Golden Oak is a gated residential resort community where families can enjoy luxury, privacy, and the magic of Disney. It features distinctive neighborhoods with magnificent homes, expansive natural preserves, and a range of inviting amenities. Residents will have access to Golden Oak’s private clubhouse, Summerhouse, with superb dining, courtyards, a pool area, fitness facilities, and a family room. Additionally, residents can enjoy Club Life, which includes services like park transportation, signature club events, theme park experiences, and much more. As Four Seasons residents, owners will have access to exceptional services such as in-home dining, poolside food and beverage service, dog walking areas, and more. Exclusive privileges also include access to the Four Seasons Resort Orlando amenities, such as the Fitness Center, Tennis and Pickleball courts, the 13,000-square-foot spa, and the acclaimed Tom Fazio-designed Golf Course. Members also have the opportunity for unlimited golf and invitations to special events.

10160 Autumn Mist Lane Unit 800, Golden Oak

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