5333 GREENSIDE CT, Orlando, FL 32819
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George Duquette

George Duquette

+1(917) 331-0412
$ 2,150,000
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5333 GREENSIDE CT Orlando, FL 32819

8 Beds

9 Baths

8,386 SqFt

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 8,386 sqft

Price per Sqft $256

Subdivision Turnbury Woods

MLS Listing ID A4699411

Bedrooms 8

Full Baths 9

HOA Fees $880/ann

HOA Y/N Yes

Annual Recurring Fee 880.0

Year Built 1985

Annual Tax Amount $12,837

Lot Size 0.710 Acres

Acres 0.71

Property Sub-Type Single Family Residence

Source Stellar MLS

Property 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.

Location

State FL

County Orange

Community Turnbury Woods

Area 32819 - Orlando/Bay Hill/Sand Lake

Zoning R-1AAAA

Rooms

Other Rooms Bonus Room, Den/Library/Office, Family Room, Great Room, Inside Utility, Interior In-Law Suite w/Private Entry, Storage Rooms

Interior

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

Heating Central, Electric

Cooling Central Air

Flooring Carpet, Tile, Wood

Fireplaces Type Family Room, Wood Burning

Furnishings Unfurnished

Fireplace true

Appliance Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer

Laundry Inside, Laundry Room

Exterior

Exterior Feature Courtyard, French Doors, Lighting, Private Mailbox, Private Yard, Rain Gutters

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

Garage Spaces 9.0

Pool Heated, In Ground, Lighting

Community Features Street Lights

Utilities Available Cable Connected, Electricity Connected, Phone Available, Sewer Connected, Water Connected

Water Access No

Roof Type Shingle

Porch Covered, Front Porch

Attached Garage true

Exposure North

Garage true

Private Pool Yes

Building

Lot Description Cul-De-Sac, Landscaped, Level, Oversized Lot, Private, Paved

Entry Level Two

Foundation Slab

Lot Size Range 1/2 to less than 1

Sewer Public Sewer, Septic Tank

Water Public

Architectural Style Colonial, Courtyard, Traditional

Structure Type Block,Stucco,Frame

New Construction false

Schools

Elementary Schools Palm Lake Elem

Middle Schools Chain Of Lakes Middle

High Schools Olympia High

Others

Pets Allowed Cats OK, Dogs OK

Senior Community No

Ownership Fee Simple

Monthly Total Fees $73

Acceptable Financing Cash, Conventional, VA Loan

Membership Fee Required Required

Listing Terms Cash, Conventional, VA Loan

Special Listing Condition None

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Stellar MLS
© 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved.
Listed by Johnny Hopper, PA PREFERRED SHORE LLC

NEARBY SCHOOLS & PROPERTIES

George Duquette

George Duquette

Advisor | License ID: SL3461231

+1(917) 331-0412

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5333 GREENSIDE CT