5333 GREENSIDE COURT Orlando, FL $ 2,150,000
5333 GREENSIDE COURT
$ 2,150,000
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5333 GREENSIDE COURT

Orlando, FL, 32819
$ 2,150,000
Bedrooms8 Baths9.0 Sq 8,386

Monthly Estimate*

$ 13,575

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Single Family Home for sale in Orlando, FL

for $2,150,000 with 8 bedrooms and 9 full baths. This 8,386 square foot home was built in 1985 on a lot size of 0.71.

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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Single Family Active

Price

$ 2,150,000

Bedrooms

8

Full Bath

9

Property Type

Single Family

Taxes

$ 12,837

Style

Colonial Courtyard Traditional

Lot Size

0.71

Year Built

1985

Town/City

Orlando

County/Region

Orange

MLS | Web ID

A4699411

Features
General
Sewer Public Sewer Septic Tank
Heating Central Electric
Cooling Central Air
Utilities Cable Connected Electricity Connected Phone Available Sewer Connected Street Lights Water Connected
Roof Shingle
Appliances Dishwasher Dryer Electric Water Heater Microwave Range Range Hood Refrigerator Washer
Zoning R-1AAAA
HOA Fee 880
Garage Spaces 9
Patio/Porch Features Covered Front Porch
Architectural Style Colonial Courtyard Traditional
Pool Features Heated In Ground Lighting
Construction Materials Block Stucco Wood Frame
Pets Allowed Cats OK Dogs OK
Year Built 1985
Electric Photovoltaics Seller Owned
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Assoc Fee Paid Per Annually
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name TURNBURY WOODS
Facing Direction North
Garage Y/N true
Green Energy Generation Solar
Total Rooms 3
Full Baths 9
Status Active
Directions 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.
High School Olympia High
City ORLANDO
Association Name Jeff Calvert
Senior Community Y/N false
MLS Area 32819 - Orlando/Bay Hill/Sand Lake
Lot Size Units Square Feet
Lot Size Square Feet 30800
Carport Y/N false
Listing Terms Cash Conventional VA Loan
Spa Features Heated In Ground
Elementary School Palm Lake Elem
Land Lease Y/N false
Tax Annual Amount 12837
Middle/Junior High School Chain of Lakes Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://my.matterport.com/show/?m=F3Mq8Qjuax6&mls=1 https://www.dropbox.com/scl/fo/yam12g3iby9w0z6hf34wn/ALOvWRI1PQid23tqIKgq8Hc?rlkey=1nuyq7e46i6kao6grslphdvox&st=5377643e&dl=0
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 33
Legal Description TURNBURY WOODS 13/24 LOT 33
Minimum Lease 1-2 Years
Water Access Y/N false
Monthly HOA Amount 73.33
Additional Rooms Bonus Room Den/Library/Office Family Room Great Room Inside Utility Interior In-Law Suite w/Private Entry Storage Rooms
Water View Y/N false
Flood Zone Code X
In Law Suite YN true
In Law Suite Description 2+ Bathrooms 2+ Bedrooms Kitchen Private Entrance
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Interior
Interior Amenities Ceiling Fan(s) Eating Space 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
Flooring Carpet Tile Hardwood
Furnished Y/N Unfurnished
Fireplace Features Family Room Wood Burning
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 0
Laundry Features Inside Laundry Room
Total Bedrooms 8
Total Baths 9
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Exterior
Exterior Amenities Courtyard French Doors Irrigation System Lighting Private Mailbox Private Yard Rain Gutters
Vegetation Oak Trees Trees/Landscaped
Parking Features Driveway Garage Door Opener Ground Level Oversized Parking Pad RV Parking
Lot Features Cul-De-Sac Landscaped Level Oversized Lot Private
Water Source Public
Lot Size Area 30800
Foundation Details Slab
Spa true
Building Area Total 11305
Lot Size Acres 0.71
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 9
Road Frontage Type Street Paved
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* Excluded Features
List By
hoppersellshomes@gmail.com

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Affordability Calculator

$14,645
Per Month
93%
7%
0%
Monthly Principal & Interest
$13,575
Monthly Property Taxes
$1,070
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Olympia High High School High School
Pricing History
DatePricePrice ChangeDescription
7/10/2026$2,150,000 Listed Price

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5333 GREENSIDE COURT, Orlando, FL, 32819 is a Single Family Home for sale at $2,150,000 with 8,386 sqft and a lot size of 0.71. 5333 GREENSIDE COURT has 8 bedrooms, 9.0 baths, and was built in 1985. The property's zip code is 32819 which is in Orlando, FL