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$399,900 Just Listed
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Property Description
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.
Full Property Details
Full Property Details for 1999 Key Bay Trail
General
- Price: $399,900
- HOA FEE: $480/month
- Taxes: $6,794 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: TB8559333
- Updated: 10/27/2026
- Added to Site: 4 day(s) ago
Rental Information
- Min. Lease: 1-2 Years
Interior
- Number of Rooms: 7
- Interior Features: Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Window Treatments
- Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Exhaust Fan, Gas Water Heater, Microwave, Range, Range Hood, Tankless Water Heater
- Furnishings: Unfurnished
- Flooring: Laminate
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 2
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Clubhouse, Fitness Center, Gated, Lobby Key Required, Pickleball Court(s), Pool, Security, Shuffleboard Court
- Security/Safety: Gated Community, Key Card Entry, Security Gate, Security System, Security System Owned
Exterior
- Exterior Features: French Doors, Hurricane Shutters, Irrigation System, Rain Gutters, Sidewalk
- Deck/Patio: Deck, Enclosed, Rear Porch
- Porch/Patio/Deck: Deck, Enclosed, Rear Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Garage Door Opener
Location
- Area: 34747 - Kissimmee/Celebration
- County: Osceola
- Development Name: 34747 - Kissimmee/Celebration
- Subdivision: FOUR SEASONS AT ORLANDO PH 4B
- Driving Directions: From Mystic Dunes Golf Club, take US-192 West toward Kissimmee and turn left onto Four Seasons Boulevard. Pass through the gated entrance of Four Seasons at Orlando, continue straight to Key Bay Trail, and turn right. Drive to 1999 Key Bay Trail, Kissimmee, FL 34747, which will be on your right.
- Direction Faces: East
Community
- Community Name: 34747 - Kissimmee/Celebration
- Community Features: Deed Restrictions, Fitness Center, Gated Community - Guard, Golf Carts OK, Irrigation-Reclaimed Water, Pool, Sidewalks, Tennis Court(s)
- Optional Amenities: Clubhouse, Fitness Center, Gated, Lobby Key Required, Pickleball Court(s), Pool, Security, Shuffleboard Cou
- Association: Yes
- Assoc. Name: Castle
- Assoc. Fees Include: 24-Hour Guard, Community Pool, Maintenance Grounds, Pool Maintenance, Security, Trash
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Street Lights, Underground Utilities, Water Available, Water Connected
Structural Information
- Architectural Info: Ranch
- Architectural Style: Ranch
- Builder: K. Hovnanian Homes
- Exterior Const.: Stucco
- Roof: Shingle
- Windows: ENERGY STAR Qualified Windows, Shutters
- Stories/Levels: One
- Square Feet: 1,583
- Sq. Ft. Source: Owner
- Year Built: 2023
Manufactured Home
- Make: 04/28/2023
Lot Features
- Lot Size (Acres): 0.1
- Lot Size (Sq. Ft.): 4,356
- Lot Size: 4356
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
Financial Considerations
- Association Fee: $480
- Assoc Fee Freq.: Monthly
- Assoc Fee Desc.: Required
- CDD: Yes
- Tax Amount: $6,794
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: FOUR SEASONS AT ORLANDO PH 4B PB 32 PGS 37-39 LOT 550
- Flood Zone Info: X
- APN: 152527357100015500
- Property ID: 152527357100015500
- Block/Lot/Section: 1
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Schools
Schools serving 1999 Key Bay Trail
School District:Osceola County School District
| Name | Grades | Distance |
|---|---|---|
Celebration School 510 Campus St, Celebration, FL 34747 | PK-5 | 2.9 mi |
Poinciana High School 2300 South Poinciana Boulevard, Kissimmee, FL 34758 | 9-12 | 8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1999 Key Bay Trail
Date
Details
Price
Change
Source
10/27/2026
Listed
$399,900
14.8%
MLS
3/31/2023
Sold
$348,330
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 1999 Key Bay Trail
Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,794
3%
$219,066
3%
2024
$6,625
37%
$212,893
166%
2023
$4,838
89%
$80,000
220%
2022
$2,559
—
$25,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1999 Key Bay Trail
1999 Key Bay Trail, Kissimmee, FL 34747 (MLS# TB8559333) is a Single Family property with 2 bedrooms and 2 full bathrooms. 1999 Key Bay Trail is currently listed for $399,900 and was received on October 27, 2026. Want to learn more about 1999 Key Bay Trail? Do you have questions about finding other Single Family real estate for sale in Kissimmee? You can browse all Kissimmee real estate or contact a Coldwell Banker agent to request more information.

