# 1999 KEY BAY Trail, Kissimmee, FL 34747 > **TL;DR:** 2bd/2ba single family, $399,900 ($253/sqft), built 2023, 1,583 sqft. > A/C, 2-car garage. Est. $2,139/mo. Listed 8 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $399,900 | | Price/sqft | $253 | | Bedrooms | 2 | | Bathrooms | 2 full | | Square Feet | 1,583 | | Year Built | 2023 | | Lot Size | 4,356 sqft (0.10 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 8 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,022 | | Estimated Insurance | $117 | | **Total** | **$2,139** | ## Key Amenities - A/C - 2-car garage ## Property Highlights - Built in 2023 - 0.10 acre lot ## Description ### Agent 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. ## Location - **Address:** 1999 KEY BAY Trail, Kissimmee, FL 34747 - **County:** Osceola - **Neighborhood:** FOUR SEASONS AT ORLANDO PH 4B - **Coordinates:** 28.308517, -81.590708 - **Google Maps:** https://www.google.com/maps?q=28.308517,-81.590708 ## Listing Agent - **Name:** Jonathan Minerick - **Brokerage:** homecoin.com - **Broker Phone:** (888) 400-2513 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/1999-Key-Bay-Trl_Kissimmee_FL_34747_M92465-80274?f=listhub&s=MFRMLSFL&m=TB8559333&c=propsimple) ## Photos ![1999 KEY BAY Trail - Photo 1](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f2493049831r.jpg) ![1999 KEY BAY Trail - Photo 2](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f3868204132r.jpg) ![1999 KEY BAY Trail - Photo 3](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f944915224r.jpg) ![1999 KEY BAY Trail - Photo 4](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f1206401854r.jpg) ![1999 KEY BAY Trail - Photo 5](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f419919740r.jpg) ![1999 KEY BAY Trail - Photo 6](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f4195443854r.jpg) ![1999 KEY BAY Trail - Photo 7](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f2500419108r.jpg) ![1999 KEY BAY Trail - Photo 8](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f2874326288r.jpg) ![1999 KEY BAY Trail - Photo 9](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f491106280r.jpg) ![1999 KEY BAY Trail - Photo 10](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f2496266414r.jpg) ![1999 KEY BAY Trail - Photo 11](http://lh.rdcpix.com/1a16ef2b513aa56b045d814a8ec7332bl-f2378260640r.jpg) --- **MLS#:** TB8559333 | **Updated:** 2026-10-31 **Source:** listhub *Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/1999-key-bay-trail-kissimmee-fl-34747-49b5b4776cdf4b3aa03632168e81ccfa) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/1999-key-bay-trail-kissimmee-fl-34747-49b5b4776cdf4b3aa03632168e81ccfa#listing", "url": "https://www.propertysimple.ai/listing/1999-key-bay-trail-kissimmee-fl-34747-49b5b4776cdf4b3aa03632168e81ccfa", "name": "1999 KEY BAY Trail, Kissimmee, FL 34747", "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. 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