5333 Greenside Court, Orlando, FL 32819
For Sale $1,575,000
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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.
Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Primary Bedroom Main Floor
Stone Counters
Vaulted Ceiling(s)
Walk-In Closet(s)
Wet Bar
Window Treatments
Taxes: $12,837.00
Tax Year: 2025
Association Fee: $880.00
Association Fee Frequency: Annually
Courtyard
Lighting
Private Mailbox
Private Yard
Rain Gutters
Dishwasher
Dryer
Electric Water Heater
Microwave
Range
Range Hood
Refrigerator
Washer
Elementary School: Palm Lake Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
Building Description: Colonial, Courtyard, Traditional
MLS Area: 32819 - Orlando/Bay Hill/Sand Lake
Total Square Footage: 11,305
Price per Square Feet: $187.81
Water: Public
Construction: Block, Stucco, Frame
Date Listed: 2026-07-10 00:00:00
Pool: Y
Pool Description: Heated, In Ground, Lighting
Private Spa: Y
Furnished: Unfurnished
Parking: Driveway, Garage Door Opener, Ground Level, Oversized, Parking Pad, Rv Access/Parking
Garage Description: Y
Garage Spaces: 9
Attached Garage: Y
Flooring: Carpet, Tile, Wood
Roof: Shingle
Heating: Central, Electric
Cooling: Central Air
Fireplace: Y
Laundry: Inside, Laundry Room
Pets: Cats Ok, Dogs Ok
Sewer: Public Sewer, Septic Tank
Lot Desc.: Cul-De-Sac, Landscaped, Level, Oversized Lot, Private, Paved
Parcel ID: 15-23-28-8783-0
Listing Courtesy Of: Preferred Shore Llc
hoppersellshomes@gmail.com
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.
Property Details
Price: $1,575,000
Sq Ft: 8,386
($188 per
sqft)
Bedrooms: 8
Bathrooms: 9
City: Orlando
County: Orange
Type: Single Family
Development: Turnbury Woods
Acres: 0.7100
Virtual Tour/Floorplan: View
Year Built: 1985
Listing Number: A4699411
Status Code: A-Active
Taxes: $12,837.00
Tax Year: 2025
Garage:
9
/
Y
Furnishings: Unfurnished
Pets Allowed: Cats OK, Dogs OK
Total Recurring Fees: $73
Total Recurring Fee Frequency: 0.00
Interior Features:
Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Primary Bedroom Main Floor
Stone Counters
Vaulted Ceiling(s)
Walk-In Closet(s)
Wet Bar
Window Treatments
Financial Information:
Taxes: $12,837.00
Tax Year: 2025
Association Fee: $880.00
Association Fee Frequency: Annually
Exterior Features:
Courtyard
Lighting
Private Mailbox
Private Yard
Rain Gutters
Equipment:
Dishwasher
Dryer
Electric Water Heater
Microwave
Range
Range Hood
Refrigerator
Washer
School Information:
Elementary School: Palm Lake Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
Additional Information:
Building Description: Colonial, Courtyard, Traditional
MLS Area: 32819 - Orlando/Bay Hill/Sand Lake
Total Square Footage: 11,305
Price per Square Feet: $187.81
Water: Public
Construction: Block, Stucco, Frame
Date Listed: 2026-07-10 00:00:00
Pool: Y
Pool Description: Heated, In Ground, Lighting
Private Spa: Y
Furnished: Unfurnished
Parking: Driveway, Garage Door Opener, Ground Level, Oversized, Parking Pad, Rv Access/Parking
Garage Description: Y
Garage Spaces: 9
Attached Garage: Y
Flooring: Carpet, Tile, Wood
Roof: Shingle
Heating: Central, Electric
Cooling: Central Air
Fireplace: Y
Laundry: Inside, Laundry Room
Pets: Cats Ok, Dogs Ok
Sewer: Public Sewer, Septic Tank
Lot Desc.: Cul-De-Sac, Landscaped, Level, Oversized Lot, Private, Paved
Parcel ID: 15-23-28-8783-0
Map of 5333 Greenside Court, Orlando, FL 32819
Listing Courtesy Of: Preferred Shore Llc
hoppersellshomes@gmail.com