KISSIMMEE, FL 34747
Welcome to Windsor at Westside—one of Central Florida's premier resort communities and one of the most sought-after destinations for vacation homeowners and short-term rental investors. This beautifully furnished 4-bedroom, 3.5-bathroom townhome combines exceptional guest appeal with thoughtful upgrades, a private pond view, and a proven rental history. The open-concept floor plan offers a spacious kitchen featuring upgraded white quartz countertops, stainless steel appliances, abundant cabinet space, and a large breakfast bar overlooking the dining and living areas, creating the perfect space for entertaining family and guests. Sliding glass doors lead to the covered lanai with a convenient poolside half bath and a private screened-in pool overlooking a tranquil pond, providing a peaceful setting with no direct rear neighbors. The first floor features a spacious guest bedroom and a full bathroom, making it ideal for multigenerational families or guests seeking first-floor accommodations. Upstairs you'll find three additional bedrooms, including a generous primary suite with an en-suite bathroom and walk-in closet. A custom-themed bunk room showcases a hand-painted mural by a local artist, creating a unique and memorable space that guests of all ages will appreciate, while an additional guest bedroom and full bathroom complete the second floor. Beyond its beautiful presentation, this property boasts a proven short-term rental history, making it an outstanding turnkey investment opportunity or vacation home. Residents and guests enjoy access to Windsor at Westside's exceptional resort amenities, including a 10,000-square-foot clubhouse, lagoon-style pool, lazy river, waterslide, splash pad, fitness center, arcade, basketball, volleyball and soccer courts, Tu Casa Bar & Lounge, on-site restaurant and coffee bar, playground, and 24-hour gated security. Ideally located just minutes from Walt Disney World, championship golf courses, shopping, dining, and Orlando's world-famous attractions, this exceptional property offers the perfect combination of location, lifestyle, and investment potential.
Sample estimate — not an appraisal
Based on 17 comparable sales within 2 miles of KISSIMMEE, FL. priced under RENA ValiQ.
Reference only. Estimates blend public sale comps, neighbourhood trend and the listing’s own metrics. Final price moves on diligence, terms and timing — RENA is your second read, not your agent.
Tax, insurance and HOA are editable estimates with Florida-typical defaults — Florida homeowners insurance in particular varies widely by location and elevation. Confirm exact figures with a lender and insurer.
Reference timeline for $409,900. Live MLS history swaps in with the Stellar feed.
| Date | Event | Price | Change |
|---|---|---|---|
| 2026-07 | Listing updated | $409,900 | — |
| 2026-04 | Price changed | $409,900 | −$20,495 |
| 2026-02 | Listed | $430,395 | — |
Reference scores for KISSIMMEE, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.
Listed by Uno Sorlie · HOPKEY REALTY
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
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