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5333 Greenside Court

ORLANDO, FL 32819
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Bed 8

Bed

Bath 9

Bath

SqFt8,386

Sqft

Acres0.71

Acre(Lot)

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.

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Detail Ic Property Details

Property Type : Residential

Price : $1,999,000

AD Id : 87874161

MLS Id : MFRA4699411

Beds : 8

Lot Size : 0.71 Acre

Living Area Size : 8,386

Year Built : 1985

Garage : 9

County : Orange

Subdivision: Turnbury Woods

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Map

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Feature Features

  • Bedroom Information

    Total Bedroom: 8

    Bathroom Information

    Total Baths: 9 Full Baths: 9

    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 Roof: Shingle Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer Laundry Features: Inside, Laundry Room

    Roofing Information

    Shingle
  • Flooring Information

    Flooring: Carpet, Tile, Wood Construction Materials: Block, Stucco, Frame
  • Heating & Cooling

    Heating: Central, Electric Cooling: Central Air WaterSource: Public

  • Building Information

    Year Built: 1985
  • Exterior Features

    Courtyard, French Doors, Lighting, Private Mailbox, Private Yard, Rain Gutters Construction Materials: Block, Stucco, Frame Foundation Details: Slab
  • Pool Features

    Private Pool: 1 Heated, In Ground, Lighting

  • Lot Information

    Lot Description: Cul-De-Sac, Landscaped, Level, Oversized Lot, Private, Paved Lot Square Feet: 30800 Lot Acres: 0.71 Lot Size (SqMt): 2861

    Property Information

    Property Type: Residential Sub Type: Single Family Residence Style: Colonial, Courtyard, Traditional

  • Listing Price Information

    Original List Price:$2150000

  • Tax Information

    Tax Block: NA Tax Book Number: 13-24 Tax Lot: 33 Tax Legal Description: TURNBURY WOODS 13/24 LOT 33 Annual Tax: $12837 Tax Year: 2025 Parcel Number: 15-23-28-8783-00-330

  • Parking Information

    Driveway, Garage Door Opener, Ground Level, Oversized, Parking Pad, RV Access/Parking

    Garage Information

    Has Garage: Yes Garage Space: 9

    Homeowners Association Information

    HOA: $880.00 Annually

  • School Information

    Elementary School: Palm Lake Elem Junior High School: Chain of Lakes Middle Senior High School: Olympia High
  • Utility Information

    Cable Connected, Electricity Connected, Phone Available, Sewer Connected, Water Connected Sewer: Public Sewer, Septic Tank Water Source: Public
  • Location Information

    Subdivision: TURNBURY WOODS City: ORLANDO Direction: From south Apopka Vineland Rd, take a right hand turn onto Bay Ridge Blvd; in .3 miles take a right hand turn onto Greenside Ct; in 450 ft, 5333 Greenside Ct will be on your left.
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ByOwner last updated this listing 07/18/2026 @ 06:20

MLS: MFRMLS #A4699411 LISTED BY: Johnny Hopper, PA, PREFERRED SHORE LLC 941-999-1179 SOURCE: MFRMLS (My Florida Regional MLS DBA Stellar MLS) (Listings courtesy of MFRMLS (My Florida Regional MLS DBA Stellar MLS) as distributed by MLS GRID)

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