55 photos in the listing
4708 Windwood Drive
Kissimmee, FL 34746 · Osceola County
$359,900
3
Beds
2
Baths
1,657
Sq ft
1992
Year built
Location
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) 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.
Facts & features
Interior
- Bedrooms
- 3
- Bathrooms
- 2
- Living area
- 1,657 sq ft
- Stories
- 1
- Flooring
- Carpet, Luxury Vinyl, Tile
- Appliances
- Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Features
- Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan
- Cooling
- Central Air
- Heating
- Central
Exterior & lot
- Lot size
- 0.17 acres
- Construction
- Block, Stucco
- Roof
- Shingle
- Features
- Other
- Pool
- Yes
Parking
- Garage spaces
- 2
Financial
- Price / sqft
- $217/sqft
- Annual tax
- $5,658.63
- Tax year
- 2025
- HOA fee
- $300
- HOA billed
- Annually
Utilities
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Water Connected
- Water
- Public
- Sewer
- Public Sewer
Property
- Property type
- Single Family
- Year built
- 1992
- Subdivision
- Windward Cay Unit 1
- Days on market
- 1 day
Estimate your monthly cost
Twenty percent down over thirty years at 6.5%. Insurance is not included.
- Principal & interest
- $1,820
- Property tax
- $472
- HOA dues
- $25
- Estimated monthly
- $2,317
Ask about this property
Answered from this listing’s own figures and the sales around it.
Similar homes nearby
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Oct 19, 2026 | Listed | $359,900 | — |
Neighbourhood
The schools below come from the MLS record for this home. Walking, transit and cycling figures for Kissimmee, FL are not connected yet, so this page does not show them.
About this area
KISSIMMEE, FL sits in Osceola County. Asking prices on the 8 nearest homes we hold run from $356,000 to $545,000, with $427,500 in the middle. Those are asking prices, not closed sales.
Written from this listing’s own record and the homes we hold nearby.
- Elementary school
- Not listed
- Not named in the MLS record for this home
- Middle school
- Not listed
- Not named in the MLS record for this home
- High school
- Not listed
- Not named in the MLS record for this home
Frequently asked questions
What would 4708 WINDWOOD DRIVE, KISSIMMEE cost per month?
About $2,317 a month: $1,820 principal and interest, $472 property tax, $25 HOA. That assumes 20% down at 6.5% over 30 years, and leaves out insurance.
Is 4708 WINDWOOD DRIVE, KISSIMMEE priced fairly?
Comparable homes nearby put it between $359,826 and $413,994, with $386,910 in the middle. Those are asking prices, not closed sales: 8 properties of the same type within three miles, each within 20% of this one's size and a bedroom either way, at a median of $234 a square foot.
How does 4708 WINDWOOD DRIVE, KISSIMMEE compare to nearby homes?
8 comparable properties within three miles. The nearest: 4811 PLINY COURT, KISSIMMEE, FL at $356,000, 1,570 sq ft, 0.17 miles away; 4784 OREN BROWN ROAD, KISSIMMEE, FL at $545,000, 1,728 sq ft, 0.35 miles away; 1310 SEASONS BOULEVARD, KISSIMMEE, FL at $485,000, 1,940 sq ft, 0.43 miles away.
How long has 4708 WINDWOOD DRIVE, KISSIMMEE been on the market?
It came on the market today.
Has the price of 4708 WINDWOOD DRIVE, KISSIMMEE changed?
The price has not moved since it was listed.
How big is 4708 WINDWOOD DRIVE, KISSIMMEE?
3 bed, 2 bath, 1,657 square feet. That is $217 a square foot.
What year was 4708 WINDWOOD DRIVE, KISSIMMEE built?
Built in 1992.
What is the HOA fee at 4708 WINDWOOD DRIVE, KISSIMMEE?
The association fee works out to $25 a month.
What are the property taxes at 4708 WINDWOOD DRIVE, KISSIMMEE?
Property tax works out to about $472 a month, $5,659 a year, on the 2025 assessment.
Is 4708 WINDWOOD DRIVE, KISSIMMEE still available?
It is still on the market.
Listing
- Listed by
- Ali Yche
- Brokerage
- SOUTHERN PRESTIGE REALTY INC
- MLS number
- MFR814519099
Listing information is deemed reliable but is not guaranteed.