5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758

$499,0004 Beds3 Baths2,847 Sq. Ft.$175 / sq. ft.

KISSIMMEE, FL 34758 · MLS# S5147335 · Active · WILLOW BEND AT CRESCENT LAKES

Status
Active
Type
Single Family Residence
Year Built
2003
Days on Market
113
Lot Size
8,617 sqft
MLS #
S5147335
County
Osceola

Description of 5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758

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 for 5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758

Bathrooms Full
2
Bathrooms Half
1
Interior Features
Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Open Floorplan, Thermostat, Window Treatments
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer
Flooring
Carpet, Ceramic Tile, Vinyl
Heating
Central, Electric, Natural Gas
Cooling
Central Air
Furnished
Negotiable
Architectural Style
Contemporary
Garage Spaces
2
Attached Garage
Yes
Parking Features
Driveway, Garage Door Opener
Pool Features
Deck, Gunite, In Ground, Screen Enclosure
Pool Private
Yes
Direction Faces
North

Building Information for 5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758

Building Area Total
3403
Building Area Units
Square Feet
Association
No
Pets Allowed
Yes

Property Information for 5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758

Lot Features
Conservation Area, Greenbelt, Landscaped, Oversized Lot, Sidewalk
Lot Size Square Feet
8,617
Waterfront
Yes
Waterfront Features
Lake Front
View
Park/Greenbelt, Pool, Trees/Woods, Water
Construction Materials
Block, Stucco
Roof
Shingle
Exterior Features
Private Yard, Sliding Doors
Sewer
Public Sewer
Water Source
Public
New Construction
No

Public Records for 5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758

Parcel Number
152628550600010010
Tax Annual Amount
$4,099
Tax Year
2025
Tax Legal Description
WILLOW BEND AT CRESCENT LAKES PB 13 PG 35-37 LOT 1
Zoning
OPUD
County Or Parish
Osceola

Schools Near 5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758

Elementary School
Reedy Creek Elem (K 5)
Middle School
Horizon Middle
High School
Poinciana High School

School assignments are provided by the listing and should be independently verified.

Payment Calculator

Estimated Payment
$3,115/mo
Principal & Interest
$2,523
Property Taxes
$342
Home Insurance
$250

Estimate only — actual rates, taxes and insurance vary. Not a loan offer or financial advice. Financing through Matthew Gromadzki, NMLS #2560919 · Innovative Mortgage Services, Inc., NMLS #250769.

Location

5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758 · See all Kissimmee homes for sale

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More information about 5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758

5500 WILLOW BEND TRAIL is a single family home for sale in KISSIMMEE, FL 34758. This property was listed for sale on April 6, 2026 by RE/MAX HERITAGE PROFESSIONALS, it's currently listed at $499,000. This listing's school district is Osceola Public Schools. Nearby schools include Reedy Creek Elem (K 5), Horizon Middle and Poinciana High School. 5500 WILLOW BEND TRAIL is a 4-bed, 3-bath, 2,847 sqft single family home built in 2003.