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Single family home for sale at 1999 Key Bay Trl, Kissimmee, FL 34747 | MLS# TB8559333 | Listing updated on 2026-10-27
Photo 1 of Single family home for sale at 1999 Key Bay Trl, Kissimmee, FL 34747 | MLS# TB8559333 | Listing updated on 2026-10-27
Photo 2 of Single family home for sale at 1999 Key Bay Trl, Kissimmee, FL 34747 | MLS# TB8559333 | Listing updated on 2026-10-27
Photo 3 of Single family home for sale at 1999 Key Bay Trl, Kissimmee, FL 34747 | MLS# TB8559333 | Listing updated on 2026-10-27
Photo 4 of Single family home for sale at 1999 Key Bay Trl, Kissimmee, FL 34747 | MLS# TB8559333 | Listing updated on 2026-10-27
7+
Beds Icon

Street View

$399,900

Monthly Est:$1,990

  • Beds Icon2 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,583sqft

1999 Key Bay Trl, Kissimmee, FL 34747

$1,990/moEst:

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  • Single Family Residence

  • Built in 2023

  • $480/mo HOA

  • 4,356 sqft lot

  • $253/sq.ft

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.

  • Houzeo last checked: 5 minutes ago
  • Listing updated: October 27, 2026 at 8:01 pm
  • Listing Provided by: Jonathan Minerick (888) 400-2513 | HOMECOIN.COM (888) 400-2513
  • Source: Stellar MLS-FL | MLS#: TB8559333 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Osceola County

  • City

    Kissimmee

  • Neighborhood

    --

  • Year Built

    2023

  • HOA Fees

    $480/mo

  • Finished Area

    1,583 sqft

  • Lot Size

    4,356 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    TB8559333

  • MLS Status

    Active

  • Days on Market

    1

  • Cumulative Days on Market

    178

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Location

HOA Management

Castle

HOA Fees

$480/ Monthly

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Security Guard Security Guard

Pool Pool

Club House Club House

Security Gate Security Gate

Gym Gym

Trash Pickup Trash Pickup

Maintenance Maintenance

Sports Court Sports Court

Lobby Key Required Lobby Key Required

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 2

    Bathrooms: 2

Interior

  • Appliances

    Built In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Exhaust Fan, Gas Water Heater, Microwave, Range, Range Hood, Tankless Water Heater

  • Window Features

    Energy Star Qualified Windows, Shutters

  • Cooling

    Central Air

  • Heating

    Electric

  • Flooring

    Laminate

  • Interior Features

    Crown Molding, Eat 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

  • Exterior Features

    Hurricane Shutters, Rain Gutters, Sidewalk

  • Sewer

    Public Sewer

Construction

  • Year Built

    Year Built: 2023

  • Home type

    Single Family Residence

  • Architectural Style

    Ranch

  • Roof

    Shingle

  • Construction Materials

    Stucco

  • Foundation Details

    Slab

Utilities & Energy

  • Water Source

    Public

  • Laundry Features

    Laundry Room

  • Parking Features

    Driveway, Garage Door Opener

  • Association Amenities

    Clubhouse, Fitness Center, Gated, Lobby Key Required, Pickleball Court(s), Pool, Security, Shuffleboard Court

  • Security Features

    Gated Community, Key Card Entry, Security Gate, Security System, Security System Owned

  • Utilities

    Bb/hs Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Underground Utilities, Water Available, Water Connected

Other Features

  • Vegetation

    Trees/landscaped

  • Subdivision Name

    Four Seasons At Orlando Ph 4b

  • Community Features

    Deed Restrictions, Fitness Center, Gated Community Guard, Golf Carts Ok, Irrigation Reclaimed Water, Pool, Sidewalks, Tennis Court(s), Street Lights

  • Patio And Porch Features

    Deck, Enclosed, Rear Porch

  • Lot Features

    Sidewalk, Paved, Unincorporated

Price History

DateEventPrice

10/27/2026

Source: mls_logoStellar MLS-FL #MFRTB8559333

Listed for Sale

$399,900 -4.56%

$253/sqft

10/04/2026

Source: mls_logoStellar MLS-FL #MFRO6396388

Listing Removed

$419,000

$265/sqft

05/12/2026

Source: mls_logoStellar MLS-FL #MFRO6396388

Price Decreased

$419,000 -2.55%

$265/sqft

04/09/2026

Source: mls_logoStellar MLS-FL #MFRO6396388

Price Increased

$429,980 +2.62%

$272/sqft

04/09/2026

Source: mls_logoStellar MLS-FL #MFRO6396388

Listed for Sale

$419,000

$265/sqft

Nearby Homes

Based on information from Stellar MLS® through Oct 28, 2026, 07:00AM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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