1999 KEY BAY TRAIL KISSIMMEE FL 34747 | MLS #TB8559333

1999 KEY BAY TRAIL KISSIMMEE FL 34747 | MLS #TB8559333

1999 KEY BAY TRAIL
KISSIMMEE, FL, 34747
$399,900
2 Beds
2 Baths
1,583 SqFt
0.1 Acres
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MLS #TB8559333 image #0
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.

Property Details

Price:
$399,900
MLS #:
TB8559333
Status:
Active
Beds:
2
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
FOUR SEASONS AT ORLANDO PH 4B
Neighborhood:
34747kissimmeecelebration
Listed Date:
Oct 27, 2026
Finished Sq Ft:
1,583
Total Sq Ft:
2,165
Lot Size:
4,356 sqft / 0.10 acres (approx)
Year Built:
2023
RanchTennisCommunity PoolCommunity Gated34747 – Kissimmee/celebration34747kissimmeecelebrationFour Seasons At Orlando Ph 4b—1-2 YearsPets Allowed

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Schools

Interior

Appliances
Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Exhaust Fan, Gas Water Heater, Microwave, Range, Range Hood, Tankless Water Heater
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Laminate
Heating
Electric
Interior Features
Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Window Treatments
Laundry Features
Laundry Room
Levels
One

Exterior

Architectural Style
Ranch
Association Amenities
Clubhouse, Fitness Center, Gated, Lobby Key Required, Pickleball Court(s), Pool, Security, Shuffleboard Court
Attached Garage YN
1
Community Features
Deed Restrictions, Fitness Center, Gated Community – Guard, Golf Carts OK, Irrigation-Reclaimed Water, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Stucco
Covered Spaces
2
Direction Faces
East
Exterior Features
French Doors, Hurricane Shutters, Irrigation System, Rain Gutters, Sidewalk
Garage Spaces
2
Lot Features
Sidewalk, Unincorporated
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener
Patio And Porch Features
Deck, Enclosed, Rear Porch
Roof
Shingle
Security Features
Gated Community, Key Card Entry, Security Gate, Security System, Security System Owned
Window Features
ENERGY STAR Qualified Windows, Shutters

Financial

HOA Fee
$480
HOA Fee Frequency
Monthly
HOA Includes
24-Hour Guard, Community Pool, Maintenance Grounds, Pool Maintenance, Security, Trash
HOA Name
Castle
HOA Phone
954-792-6000
Tax Year
2025
Taxes
$6,794

Map

Community

Subdivisions in KISSIMMEE

Market Summary

Current real estate data for Single Family in KISSIMMEE as of Oct 28, 2026
2,267
Single Family Listed
166
Avg DOM
215
Avg $ / SqFt
$472,200
Avg List Price

Property Summary

    Located in the FOUR SEASONS AT ORLANDO PH 4B subdivision, 1999 KEY BAY TRAIL KISSIMMEE FL is a Single Family for sale in KISSIMMEE, FL, 34747. It is listed for $399,900 and features 2 beds, 2 baths, and has approximately 1,583 square feet of living space, and was originally constructed in 2023. The current price per square foot is $253. The average price per square foot for Single Family listings in KISSIMMEE is $215. The average listing price for Single Family in KISSIMMEE is $472,200. To schedule a showing of MLS#tb8559333 at 1999 KEY BAY TRAIL in KISSIMMEE, FL, contact your WINDERMERE INTERNATIONAL REALTY agent at 4079901329.

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1999 KEY BAY TRAIL
KISSIMMEE, FL

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