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    Active
    Single Family Residence

    5333 GREENSIDE COURT

    ORLANDO, FL, 32819·TURNBURY WOODS

    MLS# A4699411

    $1,899,000

    8

    Beds

    9

    Baths

    8,386

    Sq Ft

    Description

    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 Overview

    StatusActive
    TypeSingle Family Residence
    Year Built1985
    CityORLANDO
    Area32819 - ORLANDO
    SubdivisionTURNBURY WOODS
    StateFL
    CountyOrange
    List Date07/10/2026
    MLS#A4699411
    List Price$1,899,000

    Bedrooms & Bathrooms

    Bedrooms8
    Bathrooms9
    Full Bathrooms9
    Half Bathrooms0

    Structure

    StyleColonial, Courtyard, Traditional
    Garage Capacity9
    ParkingDriveway, Garage Door Opener, Ground Level, Oversized, Parking Pad, RV Access/Parking
    Construction MaterialsBlock, Stucco, Frame
    RoofShingle
    Foundation DetailsSlab
    FlooringCarpet, Tile, Wood
    Private PoolYes
    Patio & PorchCovered, Front Porch

    Size & Lot

    Living Area8,386 sqft
    Lot Size30,800 sqft
    Acres0.71
    Lot DescriptionCul-De-Sac, Landscaped, Level, Oversized Lot, Private, Paved
    Water FrontNo

    Utilities

    HeatingCentral, Electric
    CoolingCentral Air
    WaterPublic
    SewerPublic Sewer, Septic Tank

    Additional Features

    Interior FeaturesCeiling 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
    Exterior FeaturesCourtyard, Lighting, Private Mailbox, Private Yard, Rain Gutters
    AppliancesDishwasher, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer

    Contact Agent

    Holiday Realty LLC

    Central Florida Real Estate Experts

    (800) 936-1754

    Our team typically responds within 1 hour during business hours.

    Neighborhood

    About TURNBURY WOODS

    5333 GREENSIDE COURT is located in the TURNBURY WOODS community in ORLANDO, FL. Part of Orange County.

    The TURNBURY WOODS neighborhood offers convenient access to local schools, shopping, dining, parks, and major commute routes.

    HOA & Tax Information

    Annual Property Tax$12,837 (2025)

    HOA, Community & Pets

    HOA & Recurring Fees

    AssociationJeff Calvert
    HOA Fee$880 / annually

    Community Features

    Street Lights

    Pet Policy

    Pets AllowedCats OK, Dogs OK

    Pet policies are subject to HOA/condo association rules. Verify current restrictions before purchase.

    Ask About This Property

    Ask a question about this home and get quick, listing-based help from Holiday Realty.

    Answers are generated from listing data and may be incomplete — please verify details with a Holiday Realty agent.

    Listing courtesy of PREFERRED SHORE LLC · Johnny Hopper, PA

    Frequently Asked Questions

    What is the asking price for 5333 GREENSIDE COURT?

    The listing price for 5333 GREENSIDE COURT is $1,899,000.

    How many bedrooms and bathrooms does 5333 GREENSIDE COURT have?

    This property features 8 bedrooms and 9 full bathrooms.

    What is the square footage of 5333 GREENSIDE COURT?

    The living area is approximately 8,386 square feet.

    What community is 5333 GREENSIDE COURT located in?

    This property is located in the TURNBURY WOODS community in ORLANDO, FL. The neighborhood offers convenient access to local schools, shopping, dining, and parks.

    When was 5333 GREENSIDE COURT built?

    This property was built in 1985.

    What schools are near 5333 GREENSIDE COURT?

    ORLANDO is served by the Orange County Public Schools district. Contact us for details on nearby elementary, middle, and high schools, including ratings and enrollment information.

    How do I schedule a showing for 5333 GREENSIDE COURT?

    You can schedule a private showing by clicking "Schedule a Showing" on this page or calling us at (800) 936-1754.

    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 2026-09-07. All data is obtained from various sources and may not have been verified by broker or MLS GRID.

    IDX information is provided exclusively for consumers' personal noncommercial use.

    © 2026 Stellar MLS. All rights reserved.