Tucked away in one of Kissimmee’s most desirable communities, this exceptional property at 5500 Willow Bend Trail offers a rare combination of space, privacy, and breathtaking views. Situated on one of the largest—and arguably the nicest—lots in the neighborhood, this home stands out from the moment you arrive.Inside, you’ll find a home that has been meticulously maintained and thoughtfully cared for, offering a clean, move-in-ready feel throughout. The layout is both functional and inviting, with comfortable living spaces designed for everyday living and effortless entertaining. The kitchen is equipped with brand new stainless steel appliances, adding a modern touch and peace of mind for the next owner.Step outside to your private outdoor retreat featuring a large screened pool cage that fully encloses the pool—perfect for enjoying Florida living year-round. The pool pump is brand new, and the A/C system has also been recently replaced, providing added efficiency and confidence in the home’s major systems. With a roof that’s just 7 years old, the big-ticket items have already been taken care of.What truly sets this home apart is the setting. Overlooking a peaceful lake with a vast conservation area beyond, the backdrop delivers a sense of tranquility and natural beauty that is increasingly hard to find. From the comfort of your screened-in porch, you can regularly enjoy Florida wildlife, including birds and turtles — creating a true connection to nature right in your backyard. Whether you’re enjoying a quiet morning coffee, entertaining guests, or unwinding at sunset, the views here are simply unmatched. The expansive lot provides added privacy and room to breathe, creating a setting that feels both open and secluded.Even better—there is no HOA, giving you added flexibility and freedom, while still offering great amenitities such as a softball field, soccer fields, basketball courts and tennis courts and more.With standout outdoor living, premium lot positioning, major system updates, and unforgettable water and conservation views, 5500 Willow Bend Trail is a rare opportunity you don’t want to miss.
Property Details
Price:
$499,000
MLS #:
S5147335
Status:
Active
Beds:
4
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WILLOW BEND AT CRESCENT LAKES
Neighborhood:
34758kissimmeepoinciana
Listed Date:
Apr 7, 2026
Finished Sq Ft:
2,847
Total Sq Ft:
3,403
Lot Size:
8,617 sqft / 0.20 acres (approx)
Year Built:
2003
See this Listing
Schools
Elementary School:
Reedy Creek Elem (K 5)
Middle School:
Horizon Middle
High School:
Poinciana High School
Interior
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Ceramic Tile, Vinyl
Heating
Central, Electric, Natural Gas
Interior Features
Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Open Floorplan, Thermostat, Window Treatments
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Contemporary
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
North
Exterior Features
Private Yard, Sliding Doors
Garage Spaces
2
Lot Features
Conservation Area, Greenbelt, Landscaped, Oversized Lot, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener
Patio And Porch Features
Covered, Porch, Rear Porch, Screened
Roof
Shingle
View
Park/Greenbelt, Pool, Trees/Woods, Water
Waterfront Features
Lake Front
Window Features
Blinds
Financial
Tax Year
2025
Taxes
$4,099
Map
Community
- Address5500 WILLOW BEND TRAIL KISSIMMEE FL
- SubdivisionWILLOW BEND AT CRESCENT LAKES
- CityKISSIMMEE
- CountyOsceola
- Zip Code34758
Subdivisions in KISSIMMEE
- Association of Poinciana Villages
- BELLALAGO
- BELLAVIDA PH 01
- COMPASS BAY
- EAGLE LAKE PH 1
- EAST PALM RESORT CONDO
- MargaritaVille
- POINCIANA NBRHD 5 NORTH VILL 3
- POINCIANA SUBDIVISION NBRHD 5 NORTH VIL 3
- POINCIANA VLG 2 NBHD 1
- ROLLING OAKS PH 7
- Siesta Lago
- SONOMA RESORT AT TAPESTRY PH 1
- STOREY CREEK PH6
- STOREY LAKE TR K
- SUMMERVILLE RESORT
- VENTURA AT WINDSOR HILLS CONDO PH 1
Market Summary
Current real estate data for Single Family in KISSIMMEE as of Aug 29, 2026
2,313
Single Family Listed
161
Avg DOM
217
Avg $ / SqFt
$472,649
Avg List Price
Property Summary
- Located in the WILLOW BEND AT CRESCENT LAKES subdivision, 5500 WILLOW BEND TRAIL KISSIMMEE FL is a Single Family for sale in KISSIMMEE, FL, 34758. It is listed for $499,000 and features 4 beds, 3 baths, and has approximately 2,847 square feet of living space, and was originally constructed in 2003. The current price per square foot is $175. The average price per square foot for Single Family listings in KISSIMMEE is $217. The average listing price for Single Family in KISSIMMEE is $472,649. To schedule a showing of MLS#s5147335 at 5500 WILLOW BEND TRAIL in KISSIMMEE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of RE/MAX HERITAGE PROFESSIONALS. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 5500 WILLOW BEND TRAIL
KISSIMMEE, FL

