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$1,899,000

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.

8 Beds ⋅ 9 Baths ⋅ A4699411 MLS

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.

5333 Greenside Court, Orlando

Listing courtesy of PREFERRED SHORE LLC. 941-999-1179

$947,500

Ready to move in? Priced to sell for those seeking quality craftmanship and a neighborhood that is conveniently located. Not a detail has been spared. This Turnbury Woods modern treasure boasts a traditional contemporary feel. Are you seeking the sought after Dr. Phillips neighborhood with almost an acre of land? Welcome to your new home. Not a detail has been spared***newly resurfaced pool***Generac 24 KW Generator wired to home for continual power during any hurricane with two one-hundred gallons above ground tanks***New Roof within the last 6 years***new separate well for irrigation***Outdoor full-service kitchen with a Jennaire grill, refrigerator, granite stone tops, and travertine tile leading to the screened-in pool. Also, has two stainless steel 24 inch-3 drawer banks with an additional two storage cabinets in the outdoor kitchen. Enjoy this home in any season: winter, spring, summer, or fall. Find traditional 8 1/4 crown molding throughout with colonial 7 1/4' baseboards with updated luxury bathrooms, spacious bedrooms, and plantation shutters. The kitchen features custom 42" kitchen cabinets with stone backsplash featuring fantasy brown countertops and pool backsplash. Leading to the pool you'll discover New Renewal by Anderson French Door Sliders and windows throughout the home. No carpets and custom 30% staggered Porcelain Tile keeps with contemporary home easy to clean. In addition to the 3-car garage entrance, recessed LED lighting, oversized ceiling fans, and a circular drive welcome you home. This beauty and well-cared for home is waiting for the appreciative buyer.

4 Beds ⋅ 3 Baths ⋅ O6396612 MLS

Ready to move in? Priced to sell for those seeking quality craftmanship and a neighborhood that is conveniently located. Not a detail has been spared. This Turnbury Woods modern treasure boasts a traditional contemporary feel. Are you seeking the sought after Dr. Phillips neighborhood with almost an acre of land? Welcome to your new home. Not a detail has been spared***newly resurfaced pool***Generac 24 KW Generator wired to home for continual power during any hurricane with two one-hundred gallons above ground tanks***New Roof within the last 6 years***new separate well for irrigation***Outdoor full-service kitchen with a Jennaire grill, refrigerator, granite stone tops, and travertine tile leading to the screened-in pool. Also, has two stainless steel 24 inch-3 drawer banks with an additional two storage cabinets in the outdoor kitchen. Enjoy this home in any season: winter, spring, summer, or fall. Find traditional 8 1/4 crown molding throughout with colonial 7 1/4' baseboards with updated luxury bathrooms, spacious bedrooms, and plantation shutters. The kitchen features custom 42" kitchen cabinets with stone backsplash featuring fantasy brown countertops and pool backsplash. Leading to the pool you'll discover New Renewal by Anderson French Door Sliders and windows throughout the home. No carpets and custom 30% staggered Porcelain Tile keeps with contemporary home easy to clean. In addition to the 3-car garage entrance, recessed LED lighting, oversized ceiling fans, and a circular drive welcome you home. This beauty and well-cared for home is waiting for the appreciative buyer.

8707 Fernwicke Court, Orlando

Listing courtesy of KELLER WILLIAMS CLASSIC. 407-292-5400

$975,000

Welcome to 5314 Shadywood Lane, a private Dr. Phillips estate where thoughtful design, expansive scale, and modern infrastructure come together on a rare half-acre homesite. Originally built in 1985 and masterfully expanded and renovated over time, this residence now offers approximately 3,600 square feet of refined living space and more than 5,300 square feet under roof, creating a seamless blend of comfort, entertainment, and everyday luxury. Inside, the home reveals four spacious bedrooms, four full baths, and multiple lifestyle spaces, including a dedicated home theater with wet bar and sound isolation, a workout or bonus room, and an expansive garage and workshop addition. The 2021 kitchen and living area renovation introduced elevated finishes, smart functionality, and timeless design, complemented by porcelain flooring throughout and upgraded electrical, plumbing, and mechanical systems that provide long-term peace of mind. Outdoor living is equally compelling, featuring a heated pool and spa, outdoor kitchen, and extended patio environment designed for entertaining or quiet retreat. Smart home enhancements—including app-controlled irrigation, modern AC systems, EV charging capability, and updated garage technology—further enhance daily living. Positioned within one of Orlando’s most established luxury corridors, this property offers proximity to Restaurant Row, premier attractions, and top-rated schools, while maintaining the privacy and space rarely found in Dr. Phillips. A carefully evolved residence with intention behind every addition, 5314 Shadywood Lane presents a distinctive opportunity to own a truly complete Central Florida luxury home.

4 Beds ⋅ 4 Baths ⋅ O6383621 MLS

Welcome to 5314 Shadywood Lane, a private Dr. Phillips estate where thoughtful design, expansive scale, and modern infrastructure come together on a rare half-acre homesite. Originally built in 1985 and masterfully expanded and renovated over time, this residence now offers approximately 3,600 square feet of refined living space and more than 5,300 square feet under roof, creating a seamless blend of comfort, entertainment, and everyday luxury. Inside, the home reveals four spacious bedrooms, four full baths, and multiple lifestyle spaces, including a dedicated home theater with wet bar and sound isolation, a workout or bonus room, and an expansive garage and workshop addition. The 2021 kitchen and living area renovation introduced elevated finishes, smart functionality, and timeless design, complemented by porcelain flooring throughout and upgraded electrical, plumbing, and mechanical systems that provide long-term peace of mind. Outdoor living is equally compelling, featuring a heated pool and spa, outdoor kitchen, and extended patio environment designed for entertaining or quiet retreat. Smart home enhancements—including app-controlled irrigation, modern AC systems, EV charging capability, and updated garage technology—further enhance daily living. Positioned within one of Orlando’s most established luxury corridors, this property offers proximity to Restaurant Row, premier attractions, and top-rated schools, while maintaining the privacy and space rarely found in Dr. Phillips. A carefully evolved residence with intention behind every addition, 5314 Shadywood Lane presents a distinctive opportunity to own a truly complete Central Florida luxury home.

5314 Shadywood Lane, Orlando

Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS. 407-629-4420