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Property for sale at 1999 KEY BAY TRAIL, KISSIMMEE, FL, 34747
Property for sale at 1999 KEY BAY TRAIL, KISSIMMEE, FL, 34747
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1999 Key Bay TrailKissimmee, FL, 34747

2beds
2baths
1,583sqft
Single Family Residence
Built in 2023
$480 Monthly HOA Fee
$378,000
For sale
$399,900−$21,900 (5%)Reduced Nov 5, 2026
Price per sqft
$239
Days on market
11
Listed
Oct 27
MLS #TB8559333Updated Nov 5, 2026

About this property

Beautifully Upgraded Villa in Four Seasons at Orlando — 55+ Gated Community Welcome to 1999 Key Bay Trail, a beautifully maintained 2023 Sandpiper villa offering comfortable single-story living, thoughtful upgrades, and the convenience of a 55+ community in Kissimmee, Florida. This inviting home features two bedrooms, two full bathrooms, and a versatile den or home office with French doors. The open floor plan, high ceilings, crown molding, and plantation shutters create a bright, welcoming living environment. Exceptional upgrades provide comfort and peace of mind, including a 22 kW Generac whole-home standby generator with automatic transfer switch, surge protection, and warranty coverage through 2030, along with remote-controlled motorized storm shutters. HVAC and water heater service contract prepaid for one year. Enjoy Florida's outdoor lifestyle on the extended paver lanai and screened patio. Additional features include an upgraded kitchen with gas cooktop, wall oven, microwave, and dishwasher; a hot-water recirculation system; upgraded gutters; and a security alarm system. Located in Four Seasons at Orlando, residents enjoy a gated community with clubhouse, swimming pool, fitness center, tennis courts, and other recreational amenities. Convenient to Celebration, shopping, dining, entertainment, and area attractions.

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Property details

Property type
Single Family Residence
Street address
1999 Key Bay Trail
City
Kissimmee
State
FL
ZIP code
34747
Year built
2023
New construction
No
Faces
East
Rooms
7
Living area
1,583 sqft
Total building area
2,165 sqft
Architectural style
Ranch
Levels
One

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at November 7, 2026 at 2:45 PM EST

Price & sale history

Asking price reduced by $21,900 (5.5%) since first listed.

EventPrice
Price reducedMLS #TB8559333$378,000Change: −5.5%−$21,900
Listed for saleMLS #TB8559333$399,900
History may be incomplete.
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Location

Property for sale at 1999 KEY BAY TRAIL, KISSIMMEE, FL, 34747
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