Price
$1,899,000
Property type
Single Family Residence
Status
Active
Bedrooms
8 beds
Bathrooms
9 bath
Square feet
30800 Sqft
Year built
1985
Garages
9 cars
Lot size
30800 Sqft
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
Schools
Pets
Cafes
Restaurants
Frequently Asked Questions
Is it a good idea to buy a home in Kissimmee or Davenport to rent it on Airbnb?
Kissimmee and Davenport are two of the most profitable areas for vacation rentals near the Disney theme parks, thanks to year-round tourism demand. However, not all communities allow short-term rentals: you\'ll need to choose developments specifically zoned for short-term rental, such as ChampionsGate, Solara Resort, Storey Lake, Windsor Island, or Reunion. Profitability depends on the size of the home, average occupancy, and the cost of property management, HOA, and taxes. A well-located home can generate attractive income, though results may vary by season and how it\'s managed. At Florida HomeGroup Realty, we only show you Airbnb-approved properties and connect you with experienced vacation rental managers.
What are the closing costs and additional expenses when buying a property in Orlando?
When buying a property in Orlando, you should budget an additional 2% to 5% on top of the purchase price to cover closing costs. These typically include title insurance, title search, inspection, appraisal, prorated taxes, the first property insurance premium, and initial HOA fees if applicable. If you finance the purchase, add loan-related costs (origination, appraisal, and points). Property taxes in Florida usually range between 1% and 1.5% of the assessed value per year. Each transaction can vary depending on the area, property type, and builder. At Florida HomeGroup Realty, we provide a detailed estimate before you sign, so there are no surprises on closing day.
Is it better to buy a new construction home or a resale property in Orlando?
It depends on your goals. A new construction home usually comes with warranties, better energy efficiency, modern designs, and customization options; many builders also offer incentives such as rate buydowns or closing cost assistance. A resale property, on the other hand, may offer a more established location, mature landscaping, room to negotiate the price, and immediate availability. For vacation rental investment, new homes in short-term rental communities are often the preferred choice. Each decision depends on your budget, timing, and personal goals, so it\'s worth reviewing both options with a specialized advisor. At Florida HomeGroup Realty, we help you compare real options and negotiate with both builders and sellers.
Can I buy a house in Orlando if I\'m a foreigner and don\'t live in the United States?
Yes. In Florida, foreign buyers can purchase property without needing a visa, residency, or U.S. citizenship. The process is very similar to that of a local buyer: you submit an offer, complete the inspection, hire a title company, and close the deal. You\'ll only need a valid passport, proof of funds, and in some cases an ITIN for tax purposes. Keep in mind that regulations such as FIRPTA may apply when you sell the property, so it\'s wise to plan from the start. Each case can vary, which is why personalized guidance is recommended. At Florida HomeGroup Realty, we guide international buyers through every step with bilingual support and a fully transparent process.
What financing options are available to buy a home in Orlando if I\'m not a U.S. resident?
There are several alternatives to finance your Orlando property even if you live abroad. The most common is the foreign national loan, which usually requires a down payment between 25% and 35%, proof of income from your home country, and international bank references. Some buyers prefer to pay cash to close faster and refinance later. Interest rates for foreign buyers tend to be slightly higher than for local borrowers, and terms vary by lender. Each institution has its own policies, so it\'s recommended to review options with a specialized advisor before making an offer. At Florida HomeGroup Realty, we work with mortgage brokers who specialize in financing for international and Latin American buyers.
Veterans and Military Benefits
We work with Veterans specialists to provide expert guidance and access the exclusive homebuying benefits for those that have served. Find a Veterans real estate agent or VA loan officer today.
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