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$429,980 Just Listed
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Property Description
Welcome to resort-style living in the sought-after 55+ guard-gated community of Four Seasons at Orlando. This beautifully maintained home at 1999 Kay Bay Trail offers comfort, security, and thoughtful upgrades designed for easy, relaxed living. From the moment you arrive, you'll notice the care and improvements throughout the home. Enjoy your extended paver lanai (2023), perfect for morning coffee or evening gatherings, along with added gutters (2024), full-house crown molding (2023), updated blinds (2023), a screened patio (2024), and a security system (2023). The home also features a water heater with a built-in circulating pump for added convenience. Peace of mind comes standard here. A 22.000 kw standby generator ensures you'll never be without power it automatically activates within seconds, so you can continue cooking, doing laundry, and enjoying your home without interruption. For added protection, all openings are equipped with motorized roll-down shutters, offering security during storms and strong winds. This is just a glimpse of what this home has to provide. Located near hospitals, shopping, dining, and world-famous attractions like Disney, you'll have everything you need just minutes away. Come see it for yourself this may be the lifestyle and home you've been waiting for.
Full Property Details
Full Property Details for 1999 Key Bay Trail
General
- Price: $429,980
- HOA FEE: $480/month
- Taxes: $6,794 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6396388
- Updated: 4/9/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 6
- Interior Features: Crown Molding, High Ceilings, Open Floorplan
- Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator
- 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
Exterior
- Exterior Features: Hurricane Shutters
- Deck/Patio: Front Porch, Patio
- Porch/Patio/Deck: Front Porch, Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 34747 - Kissimmee/Celebration
- County: Osceola
- Development Name: 34747 - Kissimmee/Celebration
- Subdivision: FOUR SEASONS AT ORLANDO PH 4B
- Driving Directions: Driving Directions (from Downtown Orlando): Take I-4 West toward Tampa. Merge onto FL-429 South (Western Beltway) via Exit 58. Continue on FL-429 South and take Exit 6 for US-192 toward Kissimmee. Turn right onto US-192 West, then turn left onto Four Seasons Blvd. Proceed through the guard gate and continue to Key Bay Trail 1999 Key Bay Trail will be on your right.
- Direction Faces: West
School Information
- Elementary School: Island Village Elementary School
- Middle School: Horizon Middle
- High School: Poinciana High School
Community
- Community Name: 34747 - Kissimmee/Celebration
- Community Features: Clubhouse, Community Mailbox, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf Carts OK, Pool, Sidewalks, Tennis Court(s)
- Optional Amenities: Clubhouse, Fitness Center, Gated
- Association: Yes
- Assoc. Name: Manuel Trinidad
- Assoc. Fees Include: 24-Hour Guard, Common Area Taxes, Community Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Maintenance Repairs, Manager, Pest Control, Trash
- Pet Restrictions: Please contact the applicable Homeowners Association (HOA) to independently verify all pet restrictions, regulations, and requirements, as such rules are subject to change and are not guaranteed by the listing agent or brokerage.
- Adult Community: Yes
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Cable Connected, Electricity Available, Electricity Connected, Natural Gas Available, Phone Available
Structural Information
- Builder: K. Hovnanian Homes
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Common Walls: Corner Unit
- Stories/Levels: One
- Square Feet: 1,557
- Sq. Ft. Source: Public Records
- 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
- Street/Road Desc.: 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
Listed by Charles Rutenberg Realty Orlando
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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
4/09/2026
Listed
$429,980
23.44%
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# O6396388) is a Single Family property with 2 bedrooms and 2 full bathrooms. 1999 Key Bay Trail is currently listed for $429,980 and was received on April 09, 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.

