• Skip to primary navigation
  • Skip to main content
  • Skip to footer
Florida for Boomers

Florida for Boomers

Guide to Florida Retirement Communities and Condos

  • About
  • Best Communities
  • Best Places
    • Regional Overview
    • Central Florida
    • Central Gulf Coast
    • East Coast
    • Northeast Florida
    • Panhandle
    • Southeast Florida
    • Southwest Florida
  • Free Newsletter
  • Recent Articles
  • Store
    • Florida Retirement Handbook
    • Florida Retirement Masterclass
    • My Book About The Villages
    • Pick the Right Place
  • Search
Search
Dashboard
Listings
Searches
Sign in / Sign up
Save
Ask
Tour
Hide
Share
$399,900
4 Days On Site

1999 KEY BAY TRAIL
KISSIMMEE, FL 34747

For Sale|Single Family Residence|Active
2
Beds
2
Total Baths
2
Full Baths
1,583
SqFt
$253
/SqFt
2023
Built
Subdivision:
FOUR SEASONS AT ORLANDO PH 4B
County:
Osceola
1999 KEY BAY TRAIL1999 KEY BAY TRAIL1999 KEY BAY TRAIL1999 KEY BAY TRAIL
Save
Ask
Tour
Hide
Share
Photos
Map
Nearby Listings

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.

Save
Ask
Tour
Hide
Share
Listing Snapshot
Price 
$399,900
Days On Site 
4 Days
Bedrooms 
2
Inside Area (SqFt) 
1,583 sqft
Total Baths 
2
Full Baths 
2
Partial Baths 
N/A
Lot Size 
0.1 Acres
Year Built 
2023
MLS Number 
TB8559333
Status 
Active
Property Tax 
$6,794
HOA/Condo/Coop Fees 
$480 monthly
Sq Ft Source 
Owner
Friends & Family
React
Comment
Invite
No Comments Yet

Did you know? You can invite friends and family to your search. They can join your search, rate and discuss listings with you.

What's This?
Private
Recent Activity
16 hours agoListing updated with changes from the MLS
yesterdayStatus changed to Active
4 days agoListing first seen on site
General Features
Acres 
0.1
Attached Garage 
Yes
Direction Faces 
East
Foundation 
Slab
Garage 
Yes
Garage Spaces 
2
Levels 
One
Parking 
DrivewayGarage Door OpenerAttached
Pets 
Yes
Property Sub Type 
Single Family Residence
Security 
Gated CommunityKey Card EntrySecurity GateSecurity SystemSecurity System Owned
Sewer 
Public Sewer
SqFt Total 
2165
Style 
Ranch
Utilities 
Natural Gas AvailableCable AvailableElectricity ConnectedNatural Gas ConnectedSewer ConnectedUnderground UtilitiesWater AvailableWater Connected
Water Source 
Public
Zoning 
0109
Interior Features
Appliances 
Convection OvenCooktopDishwasherDisposalExhaust FanGas Water HeaterMicrowaveRangeRange HoodTankless Water Heater
Cooling 
Central Air
Flooring 
Laminate
Furnished 
Unfurnished
Heating 
Electric
Interior 
Crown MoldingEat-in KitchenHigh CeilingsOpen FloorplanWalk-In Closet(s)
Laundry Features 
Laundry Room
Window Features 
ENERGY STAR Qualified WindowsShutters
Bathroom 2 
Features - Granite Counters
Dining Room 
Dimensions - 17.6x8.4Features - Breakfast Bar, Granite Counters, Stone Counters
Kitchen 
Dimensions - 15.1x11Features - Granite Counters, Pantry, Stone Counters
Living Room 
Dimensions - 15.8x12.6
Master Bedroom 
Dimensions - 12.1x16Features - Double Vanity, Granite Counters
Office 
Dimensions - 9x11.7
Save
Ask
Tour
Hide
Share
Exterior Features
Construction Details 
Stucco
Exterior 
Rain Gutters
Lot Features 
Paved
Patio And Porch 
DeckEnclosedRear Porch
Roof 
Shingle
Windows/Doors 
ENERGY STAR Qualified WindowsShutters
Community Features
Association Amenities 
ClubhouseFitness CenterGatedPoolSecurityShuffleboard Court
Association Fee 
$480.0
Association Fee Frequency 
Monthly
Community Features 
GatedFitness CenterPoolSidewalksTennis Court(s)Street Lights
MLS Area 
34747 - Kissimmee/Celebration
Township 
25
Financing Terms Available 
CashConventional
Roads 
Asphalt
Listing courtesy of HOMECOIN.COM (888) 400-2513



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-10-28 10:35 PM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
Powered by Showcase IDX, a Constellation1 Company
Save
Ask
Tour
Hide
Share

Don’t see any homes? The MLS system might be down. Check back shortly!

Footer

Popular Articles

25 Best Places to Retire in Florida
Best Florida Retirement Communities
Cost of Living in Florida
Florida Property Taxes

Florida 55+ Communities

Jacksonville 55+ Communities
Ocala 55+ Communities
Orlando 55+ Communities
Tampa 55+ Communities
Full List of 55+ Communities

Popular Communities

The Villages
On Top of the World
Valencia Riverland
Del Webb Communities
Villages of Citrus Hills

Regions

Northeast Florida
Central East Coast
Southeast Florida
Southwest Florida
Central Gulf Coast
Central Florida
Panhandle/NW Florida

Copyright 2007-2026 Florida for Boomers

  • About
  • Advertising
  • Blog
  • Contact
  • Privacy Policy
  • Terms of Use