$359,900
4708 Windwood DriveKissimmee, FL 34746
Listing updated: October 23, 2026 at 9:16 PM ET
Listing courtesy of Southern Prestige Realty Inc · Ali Yche · MLS #O6451109 · Active · 407-614-3873Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
Virtually Staged. Whether you are searching for a sun-drenched primary residence to raise your family or a high-performing asset for your real estate portfolio, this charming, move-in-ready pool home with 3bedrooms/2bathrooms/2car garage, delivers the best of both worlds. Nestled in the established and quiet community of Windward Cay, this property offers the ultimate blend of peace, privacy, and unbeatable proximity to Orlando’s world-class attractions. Tucked away just off US-192, you will enjoy a quiet neighborhood feel paired with prime Central Florida convenience. Best of all, a BRAND NEW ROOF (October 2026) AND NEW A/C UNIT, (September 2026) gives you immediate peace of mind. The home features a central, open-concept kitchen effortlessly connects the formal dining and living rooms on one side to a cozy family room and breakfast dinette on the other ;The spacious primary suite is positioned completely separate from the guest bedrooms for maximum privacy ; the home showcases a blend of low-maintenance ceramic tile in wet areas, cozy Berber carpet in the guest bedrooms, and durable luxury vinyl plank flooring throughout the main living areas and primary suite. The family room opens up to a fully screened, in-ground swimming pool and a securely fenced backyard—providing a private haven for pets, and the perfect setup for year-round entertaining and weekend barbecues. It is perfect as a primary residence, a seasonal getaway, or a high-demand, income-producing vacation home and only minutes from local schools, championship golf courses, premier shopping, dining, and major highways. You are just a short drive from Walt Disney World, Universal Studios, and SeaWorld, ensuring a premium lifestyle for residents and maximum occupancy for short-term guests.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history4 days on market
- Status: ActiveOct 19, 2026
- Listed$359,900Oct 19, 2026
Property Documents
Documents the listing agent has made public for this property. Free to view and download.
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 4
- Subdivision
- Windward Cay Unit 1
- County
- Osceola
- Year built
- 1992
- Living area
- 1,657 sq ft
- Price/sq ft
- $217
- Building area
- 2,117 sq ft (Public Records)
- Lot size
- 7,492 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12097C0065G)
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $5,659 (2025)
- Parcel #
- 13-25-28-5469-0001-0070
- Zoning
- OPUD
- MLS #
- O6451109
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Flooring
- Carpet, Luxury Vinyl, Tile
- Appliances
- Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Interior features
- Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan
- Laundry
- In Garage
- Stories / Levels
- One
- Direction faces
- North
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
HOA & Financial
- HOA fee
- $300 / Annually
- Monthly HOA
- $25/mo
- Total monthly fees
- $25/mo
- Total annual fees
- $300
- HOA name
- Sentry Management/Rebecca Gray
- CDD
- No
- Min lease term
- 1-7 Days
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
Exterior & Construction
- Exterior features
- Other
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Slab
- Pool
- Private pool
- Water access
- Yes
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Water Connected
Community
- Pets allowed
- Breed Restrictions, Cats OK, Dogs OK
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | ||
| Great Room | ||
| Living Room | ||
| Primary Bedroom | 12x15 | |
| Bedroom 2 | 10x11 | |
| Bedroom 3 | 10x11 |
Listing Details
- Listing date
- 2026-10-18
- On market date
- 2026-10-19
- Original list price
- $359,900
- Occupant type
- Vacant
- MLS area
- 34746 - Kissimmee (West of Town)
- Listing AOR
- Orlando Regional
- Status changed
- 2026-10-19
- Tax legal description
- WINDWARD CAY UNIT 1 PB 6 PG 220 LOT 7
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From 192 East and Four Winds Blvd: Head East on US-192 toward Four Winds Boulevard. Turn Right onto Four Winds Boulevard, Turn Right into the Windwood Cay community and then turn Left onto Windwood Drive.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of October 23, 2026 at 9:16 PM ET. All data is obtained from various sources and may not have been verified by 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.
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