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.
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.
Property Details
Price:
$359,900
MLS #:
O6451109
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDWARD CAY UNIT 1
Neighborhood:
34746kissimmeewestoftown
Listed Date:
Oct 19, 2026
Finished Sq Ft:
1,657
Total Sq Ft:
2,117
Lot Size:
7,492 sqft / 0.17 acres (approx)
Year Built:
1992
See this Listing
Schools
Interior
Appliances
Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Luxury Vinyl, Tile
Heating
Central
Interior Features
Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan
Laundry Features
In Garage
Levels
One
Exterior
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
North
Exterior Features
Other
Garage Spaces
2
Roof
Shingle
Spa Features
In Ground
View
Water
Financial
HOA Fee
$300
HOA Fee Frequency
Annually
HOA Name
Sentry Management/Rebecca Gray
HOA Phone
407-846-6323
Tax Year
2025
Taxes
$5,659
Map
Community
- Address4708 WINDWOOD DRIVE KISSIMMEE FL
- SubdivisionWINDWARD CAY UNIT 1
- CityKISSIMMEE
- CountyOsceola
- Zip Code34746
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 Oct 21, 2026
2,278
Single Family Listed
165
Avg DOM
215
Avg $ / SqFt
$475,187
Avg List Price
Property Summary
- Located in the WINDWARD CAY UNIT 1 subdivision, 4708 WINDWOOD DRIVE KISSIMMEE FL is a Single Family for sale in KISSIMMEE, FL, 34746. It is listed for $359,900 and features 3 beds, 2 baths, and has approximately 1,657 square feet of living space, and was originally constructed in 1992. The current price per square foot is $217. The average price per square foot for Single Family listings in KISSIMMEE is $215. The average listing price for Single Family in KISSIMMEE is $475,187. To schedule a showing of MLS#o6451109 at 4708 WINDWOOD DRIVE in KISSIMMEE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of SOUTHERN PRESTIGE REALTY INC. 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. 4708 WINDWOOD DRIVE
KISSIMMEE, FL
