luxury houses with pool for sale Windermere, United States

Under contract-accepting backup offers. Virtually Staged. Welcome to an exceptional opportunity in the heart of Bay Hill, situated directly on the green of Hole 4-one of the community's most sought-after golf course locations. This homesite offers sweeping views of manicured fairways, mature trees, and pristine landscape, delivering the privacy, prestige, and scenery that define the Bay Hill lifestyle. This spacious single-story, 4-bedroom, 3-bath home features 2,528 sq ft of living space and a smart, well-designed layout centered around golf views and indoor-outdoor living. High ceilings, large architectural windows, and multiple sets of French doors fill the home with natural light and frame tranquil views of the pool and course. Tile flooring runs throughout, and the home includes multiple living and dining areas, a wood-burning fireplace, and a large indoor laundry/mudroom with built-in cabinetry. The expansive kitchen offers tremendous potential with abundant cabinetry, a peninsula with bar seating, a breakfast nook overlooking the pool, a skylight, and direct access to the lanai. The thoughtful split-bedroom layout includes two bedroom suites-one ideal for guests and one serving as the primary-with pool access, a large walk-in closet, dual vanities, soaking tub, and separate shower. Outdoor living is the highlight: the oversized screen-enclosed pool and lanai create the perfect setting for entertaining, relaxing, and enjoying uninterrupted golf views with no rear neighbors. The full-length covered patio is ideal for year-round use. Whether you're seeking to renovate a home with incredible bones, invest in a premier golf community, or create a custom residence with unmatched views, this property represents a rare chance to secure a trophy location in the world-renowned Bay Hill community, home of the Arnold Palmer Invitational and minutes from dining, shopping, schools, and Dr. Phillips amenities. Bring your vision and make this standout Bay Hill address your own.

Introducing 5333 Greenside Court, a rare opportunity to own one of Dr. Phillips' most versatile and thoughtfully designed private estates. Rarely does an estate of this scale, flexibility and long-term vision come available in this coveted community. Situated on a beautifully landscaped .71-acre homesite, this timeless Colonial-inspired residence offers over 8,000 square feet of thoughtfully designed living space where classic architecture and extraordinary versatility come together. Expanded with long-term functionality in mind, the home features significant capital improvements including a newer roof, 44 hurricane impact windows installed in 2022, fresh exterior paint, and a new roof with an impressive 110 panel solar system installed in 2021. That keeps average monthly electric costs at approximately 50 dollars, which is remarkable given its size. Separate septic systems serve the primary living areas, with the rear system intentionally oversized to support future expansion, including the potential conversion of portions of the garage into additional living space. Designed to evolve alongside your family's needs, this is far more than a luxury residence. It's a true legacy estate built for generations. The multi family compound offers the flexibility to function as approximately 6 to 11 bedrooms (according to your needs), 9 full bathrooms, and 3 complete kitchens, with every addition intentionally designed to create independent yet connected living spaces. The original residence offers the warmth and functionality of a traditional family home, featuring an expansive first-floor primary suite with an adjoining flex room. Upstairs, three bedrooms and two full baths provide an ideal layout while multiple living rooms, a formal dining room and an oversized kitchen create exceptional spaces for both everyday living and entertaining. The kitchen is complemented by a butler's pantry with second refrigerator and oversized laundry. At the heart of the estate, a beautifully designed heated pool and spa courtyard seamlessly connects the separate living wings while preserving privacy, creating an inviting retreat for gatherings or quiet evenings. Connecting the residences, a fully equipped gym, complete with a full bath, offers exceptional flexibility as either a private wellness center or guest suite. The secondary residential wing dramatically expands the possibilities with Spectacular 1500-square-foot executive office with its own kitchen and full bath, creating an incredible work-from-home environment or an opportunity for another luxurious primary suite, if you preferred. Adjacent is an expansive 1700+ sq. ft game room with another full kitchen, massive recreation space, additional full bath, and another private suite, providing essentially limitless options for future owners. Whether your vision includes extra bedrooms, studios, media rooms, or expanded family living. Below, an exceptional 9-car garage divided into separate four-car and five-car garages with extensive built-in storage caters to collectors, entrepreneurs, hobbyists alike. Behind the residence, an enormous motor court provides parking for roughly 25 additional vehicles, offering unmatched flexibility. Opportunities to own an estate offering this level of versatility and future potential are extraordinarily rare. 5333 Greenside Court is far more than a luxury home. It's a legacy estate where generations gather, grow, and create lasting memories for decades to come.

Some homes are simply places to live. This one is a lifestyle. Positioned directly on the 12th fairway of Arnold Palmer's Bay Hill Championship PGA golf course, this fully reimagined golf-front residence is among the most coveted offerings in all of Central Florida. Set within the gated enclave of Bay Hill Village, it delivers the rarity buyers truly seek: brand-new luxury finishes, single-level living, and an address that speaks for itself. The Residence: Spanning approximately 2,500 square feet with a commanding 125 feet of direct golf course frontage, this home was stripped down to its concrete walls and foundation and rebuilt from the ground up, resulting in a finished product that rivals new construction in every way. The gourmet kitchen is anchored by custom cabinetry, striking marble countertops, and top-of-the-line appliances. Porcelain tile flows seamlessly through the main living areas, while the spacious family room, complete with a built-in bar and wine refrigerator, sets the stage for effortless entertaining. A versatile bonus room adapts beautifully to a home office, media room, or additional living space. The primary suite is a true retreat, featuring a generous walk-in closet, dual vanities, and a spa-inspired walk-in shower. With everything replaced and rebuilt, including the roof, A/C, bathrooms, fixtures, finishes, and landscaping, this is as close to a brand-new home as you will find in one of Orlando's most iconic communities. Smart Home & Outdoor Living: A fully integrated Control4 smart home system puts lighting, climate, audio, security, and entertainment at your fingertips, whether you're home or away. Outside, a private sanctuary awaits: a tranquil waterfall fountain, hot tub, and lounge area invite you to unwind in style. The 300-square-foot screened-in patio is climate-controlled, making it fully enjoyable even through Florida's hottest summer months and the perfect vantage point for the fairway and the world-renowned Arnold Palmer Invitational. The Community: Bay Hill Village is more than a neighborhood. It's a standard of living. This gated, well-established community of approximately 120 homes offers low-maintenance lots, privacy walls, tree-lined streets, and a park-like atmosphere. Amenities include a clubhouse, resort-style pool and hot tub, tennis and pickleball courts, and a fitness center. A private rear gate opens directly to Bay Hill Club, where membership unlocks 27 holes of Championship Golf, Tennis & Pickleball, Fine Dining, Lounge, Pro Shop, 66-Room Lodge, Marina, and more! The Location: Situated in the heart of the Dr. Phillips corridor, you're steps from Restaurant Row and minutes from Walt Disney World, Universal Orlando Resort, and SeaWorld, placing the best of Orlando's dining, culture, and entertainment at your doorstep.

*Seller is Motivated* Welcome to elevated luxury, situated on the 11th green of one of the world's most iconic golf courses: Arnold Palmer's Bay Hill Club and Lodge, home of the PGA Tour's Arnold Palmer Invitational since 1979. Located at the end of a private, gated cul-de-sac, this newly constructed six-bedroom, seven-bath estate is designed for high-end entertaining. Melding a clean, modern aesthetic with a highly functional floor plan, this steel-reinforced estate redefines luxury living on the fairway. Carrara porcelain tile flows seamlessly throughout the entire first floor, offering timeless beauty with effortless durability. Dramatic 22-foot soaring ceilings and double-height glazing frame uncompromised vistas of the golf course and shimmering infinity pool. A symphony of light and leisure, the sprawling floor plan is meticulously engineered for fluid indoor-outdoor living. Massive 9-foot glass walls slide away to merge the sleek, open-concept family spaces with a resort-caliber outdoor oasis. Boasting a coveted northern and northwestern rear orientation, the panoramic pool deck catches the breathtaking colors of Central Florida's sunsets. Built for the ultimate host, the main gourmet kitchen features dual islands, two dishwashers, Sub-Zero refrigeration and a Wolf gas oven, complemented by an adjacent 534-bottle, climate-controlled glass wine display. A fully equipped back kitchen with an additional full-size catering refrigerator ensures seamless, discreet event prep away from your primary living space. Enter the double doors to the exclusive owner's retreat for the ultimate sanctuary featuring dual custom closets, a dedicated lounging area with a private lanai, a spa-like bath with a soaking tub, a seamless glass smart shower and LED light inlay mirrors above the double vanities. The residence transitions effortlessly to warm engineered hardwood on the second level, beautifully bridging structural minimalism with residential warmth. This upper floor functions as a complete private sanctuary, offering an additional kitchen, living room and ensuite bedrooms perfectly suited for family or guests. No detail in luxury or efficiency was overlooked. This custom-engineered estate features a state-of-the-art tankless propane gas hot water system flawlessly supplying all baths, high-efficiency thermal windows and an aerobic water treatment system. An expansive covered lanai creates the ultimate backdrop for year-round entertaining, overlooking a mosaic-tiled infinity pool with a heated spa, dancing fire, water and light features, a full outdoor summer kitchen and a detached pool house complete with its own private en suite. Car enthusiasts and active golfers will appreciate the expansive 4-car garage, complete with a dedicated golf cart bay. Secluded behind this property offers supreme privacy, set on nearly an acre, yet just minutes from fine dining along famed Restaurant Row, high-end shopping, Universal Studios, Walt Disney World and Orlando International Airport, a short 20-minute drive. Optional private membership to Bay Hill unlocks premier resort amenities, including championship golf, tennis, pickleball, a state-of-the-art fitness center, a full-service marina, fine dining and dynamic social events, all right in your backyard.

Under contract-accepting backup offers. Pre-Construction. To be built. This is a rare opportunity to build a new construction custom home within an established, gated neighborhood - and the last available lakefront lot in the prestigious Cypress Point community. Konkol Custom Homes, one of Central Florida’s premier luxury builders, and MJS designed plans for a 7,000-square-foot lakefront masterpiece on nearly one acre along Lake Tibet, part of the world-renowned Butler Chain of Lakes. The proposed design includes five bedrooms, seven bathrooms, a pool, and a six-car garage, all fully customizable to your vision. From your backyard, enjoy breathtaking sunsets every evening and Disney fireworks each night - without the noise or the lines. From the front view of the home, enjoy a beautiful, well-maintained pond with a fountain, taken care of by the community - so you have water ON BOTH SIDES of the home. Nestled within Cypress Point, residents enjoy lush landscaping, 24-hour manned security, and exclusive community amenities including a clubhouse, playground, and walking paths. Located in the heart of Dr. Phillips, close to the Bay Hill area, this property offers the ultimate blend of luxury, privacy, and convenience - just minutes from Restaurant Row’s world-class dining, Bay Hill Country Club, and top-rated schools. Build not only your dream home, but your legacy, in one of Central Florida’s most exclusive lakefront enclaves. Don't miss this incredibly rare opportunity to fully customize your home that suits your needs, on one of the most premium lot sites available in Central Florida. The land itself is also available for purchase separately, offering endless potential to craft your dream home in one of Dr. Phillips’ most exclusive lakefront communities. Schedule a showing today!

Tucked away on a quiet cul-de-sac within the gated community of Palma Vista, this impeccably maintained single-story residence offers the perfect balance of timeless elegance, everyday comfort, and effortless Florida living. Situated on an oversized corner lot, this thoughtfully designed home features nearly 2,900 square feet of living space with four bedrooms, three full baths, and a desirable split-bedroom floor plan that provides privacy for family and guests alike. Designed for both relaxed living and elegant entertaining, the home showcases soaring tray ceilings, expansive formal and casual living spaces, a gas fireplace, and a dedicated executive office ideal for working from home. At the heart of the home, the spacious kitchen flows seamlessly into the family room and outdoor living areas, creating an inviting space for gatherings both large and small. Step outside to your own private retreat where a solar-heated pool and spa, screened lanai, and beautifully landscaped backyard provide the perfect setting to enjoy Florida's year-round lifestyle. Whether hosting friends, enjoying a quiet evening by the pool, or simply relaxing in your own backyard oasis, this home was designed to be lived in and enjoyed. Ideally located just minutes from Restaurant Row, Dr. Phillips, Universal Orlando Resort, championship golf, world-class dining, premier shopping, and major highways, Palma Vista offers the convenience of Central Florida living within an established gated community. Meticulously cared for and move-in ready, this exceptional residence presents a rare opportunity to enjoy luxury, privacy, and resort-style living every day of the year.

Welcome to your private lakefront retreat on beautiful Lake Rose. Nestled at the end of a quiet cul-de-sac, this stunning three-bedroom, two-bath home offers just under 2,000 square feet of thoughtfully designed living space, perfect for both relaxation and entertaining. The home features a spacious layout with comfortable living areas. A three-car garage provides ample space for vehicles, storage and all your lake toys. Outside you can experience the ultimate waterfront lifestyle with your own private concrete boat ramp, making launching effortless, along with two private docks, perfect for relaxing, entertaining, or securing multiple watercrafts. Boasting an impressive 159 feet of pristine lake frontage, this property delivers breathtaking water views and unmatched access to outdoor recreation. Whether you enjoy fishing at sunrise, boating across open water, or spending the day waterskiing, paddle boarding, or kayaking, this lake is a true playground right in your backyard. Additional peace of mind comes with a roof that was replaced four years ago, offering durability and long-term value. This rare lakefront gem combines privacy, functionality and year-round recreation, all in a highly desirable cul-de-sac location in Lake Rose Pointe. Whether you're looking for a full-time residence or a weekend escape, this property is ready to deliver the lifestyle you've been dreaming of.

For one who is unwilling to compromise. This is luxury at its absolute best. From the moment you enter this modern paradise your eyes will travel through the wall of windows to the gorgeous pool and water views beyond. This Magnificent Custom build offers 5 bedrooms, 5 1/2 Bathrooms with convenient first floor master. The chef's kitchen showcases two oversized islands, quartz countertops and premium contemporary imported European cabinetry. Beautiful upscale finishes like the elegant marble floors and an automated surveillance system that allows control from anywhere you are around the globe. An outside deck, summer kitchen and covered lanai complete this awe-inspired residence located in Lake Hancock, where you can boat to the future new Hamlin Marina with shopping, movie theater and dining. Or relax in your outside porch every night to watch Disney fireworks. A home with spectacular views awaits you. Truly the Florida Lifestyle. Call to schedule a visit to this pristine property and expect to be impressed!

Welcome to an exceptional residence where luxury, lifestyle, and location converge in one of Winter Garden's most desirable communities. Situated on a hard to find oversized premium corner lot, this stunning 4-bedroom, 4-full bath home offers 3,424 square feet of thoughtfully designed living space, perfectly positioned to capture serene park views in the front and tranquil pond vistas in the rear. From the moment you arrive, the home's elevated presence and expansive setting set the tone. Inside, you are greeted by a light-filled, open-concept layout designed for both elegant entertaining and everyday comfort. The spacious floor plan flows seamlessly, enhanced by refined finishes and generous living areas. At the heart of the home, the kitchen and great room spaces connect effortlessly to the outdoors, where your private resort-style retreat awaits, outdoor living at its finest! Step outside to your private POOL (built in 2022)-a true showpiece designed for relaxation and entertaining. The fully fenced backyard with a sleek metallic fence offers both privacy and unobstructed views, creating the perfect balance of security and openness. Whether hosting gatherings or enjoying a quiet evening, the backdrop of the pond and open skies delivers an unparalleled sense of tranquility. And as the sun sets, prepare for a truly magical experience-nightly views of the MAGIC KINGDOM FIREWORKS right from your backyard create a one-of-a-kind ambiance that elevates everyday living into something extraordinary. INTERIOR HIGHLIGHTS: 4 Bedrooms | 4 Full Bathrooms. A spacious DEN located in the first floor is currently set as a guest room, with the convenience of a full bathroom in the first floor with access to the pool. A spacious BONUS ROOM located on the second floor- ideal for a media room, office, or playroom. Expansive GREAT ROOM and entertaining areas including a STUDY SPACE off of the kitchen and a DINETTE SPACE. A thoughtfully designed layout with functional flow! Recent Update:A/C UNIT REPLACED in late 2025, offering peace of mind and energy efficiency for years to come. Park views from the front - providing openness and privacy. Pond views from the rear - creating a serene and picturesque backdrop. Oversized corner lot enhances curb appeal and outdoor space. This is more than just a home-it's a lifestyle property that blends natural beauty, luxury amenities, and a prime location. From quiet mornings overlooking the pond to evenings watching Disney fireworks, every day here feels elevated.

Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

Direct Panther Lake frontage. Sunset views from your own screened lanai. Disney fireworks shimmering across the water after dark. Welcome to 15594 Shorebird Lane, an exceptional Toll Brothers Bavaro residence set on an oversized 0.34-acre homesite with approximately 93 feet of lake frontage in Lakeshore Preserve, one of Horizon West's most desirable communities. From the moment you enter, the home is designed around the water. A dramatic two-story foyer with stained shiplap and architectural beams opens to bright, expansive living spaces where oversized windows frame tranquil Panther Lake views. The open-concept great room, dining area and gourmet kitchen flow naturally together, creating an ideal setting for both everyday living and entertaining. The kitchen features a generous center island, stone countertops, upgraded appliances, built-in and convection ovens, a range hood and abundant storage. Designer lighting, additional recessed lighting, upgraded interior finishes, plantation shutters and ceiling fans throughout add warmth and refinement. The first-floor primary suite offers a peaceful lakefront retreat, complete with serene water views, a custom closet system and a spa-inspired bath. Upstairs, three additional bedrooms and a spacious bonus room provide flexibility for guests, a media room, home office, game room or second living area. But the heart of this property is outdoors. An approximately 1,250-square-foot screened lanai opens directly toward Panther Lake, creating a private waterfront setting for dining, entertaining or simply watching the colors change across the lake at sunset. A hot tub, fire pit, fountain and outdoor shower are surrounded by mature landscaping and thoughtfully designed outdoor spaces, while Disney fireworks provide a memorable backdrop after dark. The home also offers an important long-term advantage: an owned, fully paid solar system with no lease and no loan, conveying with the property. A tankless water heater, foam insulation and plantation shutters further support energy-conscious living. Additional features include custom garage cabinetry, epoxy garage flooring, an oversized two-car garage, upgraded landscaping and irrigation, gutters and downspouts, a built-in pest-control system and extensive storage solutions. With 4 bedrooms, 3.5 baths and 3,022 square feet of heated living space, this home combines Toll Brothers quality with a waterfront setting that is difficult to duplicate. Lakeshore Preserve residents enjoy resort-style amenities including a clubhouse, community pool, fitness center, yoga and wellness studio, playground, dog park, sand volleyball courts, walking and biking trails, community canoes, dock and lake access. The home is also conveniently located near Walt Disney World, Hamlin Town Center, Flamingo Crossings, Winter Garden Village, Orange County National Golf Center and downtown Winter Garden, with convenient access to SR 429, Florida's Turnpike and Interstate 4. Lakefront living. Sunset views. Disney fireworks. Paid solar. An oversized homesite and an extraordinary outdoor living space. This is not simply another home in Horizon West—it is a property designed around the experience of living on the water.

Prepare to be awed by this stunning estate from the Toll Brothers executive collection in the renowned community of Lakeshore Preserve. This home presents an ultra modern layout bringing you an environment that caters to both entertaining and every day life. The first floor is open and has 2 sets of triple pane sliding glass doors that fully open to your personal oasis. Beyond the covered lanai is a beautiful pool, spa and cabana area, perfect for a mid day swim or watching Disney fireworks at night. The kitchens, indoor and outdoor, and sure to impress even the most fastidious of chefs with the natural gas cooktop, multiple mounted range hoods, quartz countertops and more. This property is not only a smart home but also environmentally conscientious with newly installed solar panels and an electric car charger. All furniture is included with the sale of this home, the only thing you need is the keys to begin living your best central Florida life. Virtual Tour Available.

Virtually Staged. Modern Luxury in the Heart of Winter Garden's Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community-one of the few neighborhoods within Winter Garden's beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36 dual-fuel range, warming oven, and a 48 side-by-side refrigerator and freezer. Upgraded quartz countertops, a brick backsplash and hearth with built-in electric fireplace, and engineered hardwood floors elevate the open-concept main living areas. Additional luxury touches include Brizo faucets, custom plantation shutters, and floating shelving systems in every bedroom closet. The owner's suite offers a spa-inspired retreat with a 6-foot soaking tub, while the upgraded pantry with butcher block countertop, dimmer switches, and ceiling fans throughout enhance everyday comfort. An in-law suite featuring a full bath, family room, and a private staircase above the garage provides the perfect space for guests, extended family, or a private home office. Enjoy peaceful mornings and sunset evenings from the screened front and side porches, adding to the home's charm and livability. Located in Oakland Park, residents enjoy resort-style amenities including two community pools, multiple parks and playgrounds, scenic walking and biking trails, a clubhouse, and direct access to the West Orange Trail. With tree-lined streets, lake views, and friendly front-porch living, this award-winning community captures the very best of Winter Garden living.