About Crestwynd Bay
Crestwynd Bay is a gated townhome resort community tucked along N. Old Lake Wilson Road (SR-545) in the western Kissimmee resort corridor, sharing a boundary wall with the larger Windsor Hills Resort. Built between 2006 and 2007 by KB Homes, the community consists of approximately 184 two-story townhomes arranged in a Spanish Mediterranean and Contemporary architectural style, characterized by clay tile roofs, stucco exteriors, and vibrant landscaping throughout the tree-lined interior streets.
The community is approved for short-term vacation rental use, making it a versatile acquisition for owner-occupants, second-home buyers, and investors alike. Crestwynd Bay's compact footprint means residents enjoy a tight-knit resort atmosphere, with the community pool, playground, and nature trail positioned as central gathering spaces. A natural lake within the community grounds adds scenic character to the neighborhood setting.
Crestwynd Bay offers four distinct floor plans ranging from approximately 1,187 to 1,595 square feet of living space, all with three bedrooms and two to three bathrooms. Every home features a private rear patio area and a fully equipped kitchen, making units equally suited as full-time residences, seasonal retreats, or income-generating rentals. The US-192 corridor places restaurants, entertainment venues, outlet shopping, and the Kissimmee Lakefront Park within a short drive.
Because Crestwynd Bay sits at the intersection of the resort corridor and established residential neighborhoods along SR-545, it occupies a unique position in the Kissimmee market — more affordable than full resort communities with private water parks, yet still professionally managed and gated, with easy access to the SR-429 Daniel Webster Western Beltway for regional commuting.
📊 Quick Facts
🏠 Home Features
Interior features typical of Crestwynd Bay townhomes include:
- Open-concept first floor combining kitchen, dining, and living areas
- Fully equipped kitchen with standard appliances
- Tile flooring on ground floor; carpet upstairs in most units
- Three bedrooms accommodating 6–10 guests in furnished rental configurations
- Two to three full bathrooms depending on floor plan
- Many units offered furnished and move-in ready
Exterior & community features:
- Spanish Mediterranean-style clay tile roofs
- Stucco exterior with vibrant color palette
- Private rear patio area per unit
- Tree-lined interior streets with mature tropical landscaping
- Natural lake within community grounds
💡 No CDD Fee — A Financial Advantage
Crestwynd Bay has no Community Development District (CDD) fee, which is a meaningful financial differentiator compared to many newer resort communities in the Kissimmee area that add CDD assessments on top of regular HOA dues. Learn more about how CDDs work in our guide: What's a CDD?
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Crestwynd Bay Location & Connections
Crestwynd Bay is positioned along N. Old Lake Wilson Road (SR-545) in the western resort corridor of Kissimmee, placing it directly in the heart of Osceola County's vacation destination zone. The community shares its northern border with Windsor Hills Resort, and the US-192 (W. Irlo Bronson Memorial Highway) corridor runs nearby to the south, providing immediate access to theme park employment, retail centers, and entertainment destinations.
The SR-429 (Daniel Webster Western Beltway) is minutes away to the northwest, offering a direct toll route to Winter Garden, Apopka, and I-4 without navigating through heavily trafficked tourist areas. This beltway access significantly enhances the community's appeal for residents commuting to employment centers across greater Orlando.
🏘️ Adjacent Neighborhoods & Areas
- Windsor Hills Resort — directly adjacent to the north, sharing boundary wall
- Indian Ridge — nearby Westside corridor community
- Lake Wilson Reserve — to the east along Lake Wilson Road corridor
- Mystic Dunes Golf Club — resort and golf destination to the southwest
- N. Old Lake Wilson Road / Sand Hill Road / Teascone Boulevard corridor — area road network providing access to US-192 and SR-429
🚗 Detailed Commute Times
- Walt Disney World: ~8–12 minutes (3.5 miles)
- Universal Orlando: ~25–30 minutes (20 miles)
- SeaWorld Orlando: ~20–25 minutes (15 miles)
- Downtown Orlando: ~35–40 minutes (25 miles)
- UCF Campus: ~45–50 minutes (35 miles)
- Lake Nona Medical City: ~35–40 minutes (28 miles)
- Cocoa Beach: ~70–80 minutes (60 miles)
- Celebration: ~10–12 minutes (7 miles)
✈️ Airport Access
- Orlando International Airport (MCO): ~30–35 minutes (22 miles)
- Orlando Sanford International Airport (SFB): ~55–65 minutes (48 miles)
- Kissimmee Gateway Airport (ISM): ~20–25 minutes (15 miles)
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Crestwynd Bay Amenities & Lifestyle
Crestwynd Bay delivers the core resort lifestyle essentials in a compact, gated setting. The community's appeal centers on its extraordinary location — within minutes of Walt Disney World, surrounded by the full spectrum of Westside corridor dining, shopping, and entertainment — combined with a manageable community that feels less like a large resort complex and more like a private retreat.
For investors, the short-term rental eligibility positions Crestwynd Bay as a hands-off income opportunity in one of Central Florida's most in-demand vacation markets. For owner-occupants and seasonal residents, the community's proximity to the US-192 corridor means world-class entertainment, dining, and employment are never more than a few minutes away. Read our Kissimmee entertainment guide for a full picture of what this part of Osceola County has to offer.
🏊 Neighborhood Amenities
Amenities found within Crestwynd Bay:
- Gated entry with security access
- Community swimming pool with pool deck
- Playground / children's play area
- Nature trail winding through the community
- Natural lake within the community grounds
- Landscaped, tree-lined internal streets
🛍️ Shopping & Services
Crestwynd Bay residents enjoy some of Central Florida's best retail within a short drive. The Loop Shopping Center on John Young Parkway provides a large outdoor mall experience with major retailers, theaters, and dining. For upscale outlet shopping, the Orlando Vineland Premium Outlets and Lake Buena Vista Factory Stores are both reachable in under 15 minutes. Formosa Gardens Village, just east on Funie Steed Road, provides grocery and daily services.
For comprehensive shopping information: View our Kissimmee Shopping Guide →
🍽️ Restaurants
The US-192 corridor surrounding Crestwynd Bay is one of Florida's densest dining corridors, with options ranging from nationally recognized chains to Kissimmee's celebrated Latin cuisine scene featuring Cuban, Venezuelan, and Puerto Rican flavors. Dinner shows including Medieval Times and Capone's are also minutes away for a full evening out.
For comprehensive restaurant information: View our Kissimmee Restaurants Guide →
🎭 Arts & Culture
Crestwynd Bay residents can easily reach Osceola Arts in downtown Kissimmee for live theater, concerts, and community programs, and the Pioneer Village at Shingle Creek for Old Florida living history. Downtown Kissimmee's vibrant public art and mural scene along Broadway is a 20-minute drive.
For comprehensive arts & culture information: View our Kissimmee Arts & Culture Guide →
🏃 Health & Wellness
The nearest major hospitals are AdventHealth Kissimmee and HCA Florida Osceola Hospital, both accessible within 20–25 minutes. Gyms and fitness studios along the US-192 corridor provide convenient workout options, and the Bob Makinson Aquatic Center offers lap swimming and community wellness programs.
For comprehensive health & wellness information: View our Kissimmee Health & Wellness Guide →
🌳 Parks & Recreation
Crestwynd Bay's location in the western Kissimmee resort corridor puts residents close to a remarkable range of outdoor recreation. Kissimmee Lakefront Park on Lake Tohopekaliga is a 20-minute drive, offering waterfront trails, a marina, and family-friendly green space. Shingle Creek Regional Park provides kayaking and nature trails, and Kissimmee Prairie Preserve State Park — Florida's only International Dark Sky Park — is a day-trip destination.
For comprehensive parks & recreation information: View our Kissimmee Parks & Recreation Guide →
⚽ Sports & Athletics
Golfers near Crestwynd Bay have access to a strong collection of Kissimmee-area courses. The community sits near Mystic Dunes Golf Club, and championship courses throughout Kissimmee are within a short drive. The Bob Makinson Aquatic Center provides competitive aquatics facilities.
For comprehensive sports & athletics information: View our Kissimmee Sports & Athletics Guide →
🎉 Fun Things to Do
Living at Crestwynd Bay means Walt Disney World is a 10-minute drive. Gatorland, Old Town Kissimmee, Sunset Walk, and Island H2O Water Park are all within a short drive. The full theme park corridor including Universal Orlando and SeaWorld is easily accessible.
For comprehensive entertainment information: View our Kissimmee Entertainment Guide →
🎓 Schools
Crestwynd Bay (ZIP 34747) is served by Osceola County Public Schools:
- K–8: Westside K-8 School
- High School: Celebration High School
Note: School assignments are subject to change. Always verify current zoning with the Osceola County School District before purchase.
For comprehensive school information: View our Kissimmee Schools & Education Guide →
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How Crestwynd Bay Compares
Crestwynd Bay occupies a unique market position in the Kissimmee Westside corridor — offering vacation-rental eligibility and gated resort living at a price point substantially below larger resort communities with private water parks and clubhouse staffing. For buyers who want Disney-proximity and short-term rental income potential without the premium pricing of communities like Windsor Hills or Solara Resort, Crestwynd Bay is a compelling alternative.
The absence of a CDD fee is a meaningful long-term financial advantage. Many comparable resort communities in the 34747 ZIP code carry CDD assessments that add several hundred dollars per year to the cost of ownership. Crestwynd Bay homeowners avoid this additional expense while still benefiting from a well-maintained gated community setting.
| Feature | Crestwynd Bay | Windsor Hills | Indian Ridge |
|---|---|---|---|
| Home Style | 2-story townhomes | Condos, townhomes, single-family | Single-family & villas |
| Home Size | 1,187–1,595 sq ft | Varies widely (800–3,000+ sq ft) | Varies |
| Year Built | 2006–2007 | Various (2003–present) | Various |
| CDD Fee | None | Varies by section | None |
| Vacation Rental | Yes — eligible | Yes — full resort community | Check current zoning |
| Distance to Disney | ~3.5 miles | ~2 miles | ~4–5 miles |
💡 Value Proposition: Crestwynd Bay offers vacation-rental eligibility and gated living in one of Kissimmee's most desirable resort ZIP codes, with no CDD fee — making it one of the more cost-efficient entry points into the short-term rental investment market in western Osceola County.
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Crestwynd Bay HOA & CDD Information
Crestwynd Bay is governed by a mandatory Homeowners Association that oversees the gated entry, community pool, playground, nature trail, and common area landscaping. The HOA structure supports the community's resort character while maintaining common areas that serve both full-time residents and vacation rental guests.
Crestwynd Bay has no Community Development District (CDD) fee — a notable financial advantage over many resort communities in the broader 34747 area. If you'd like to understand how CDDs compare to HOAs before making a purchase decision, our guide What's a CDD? explains the key differences.
💰 HOA Fees & Management Contact
HOA fees and management company information often change. Please contact us and we will be happy to provide you with the current HOA fee, payment schedule, and direct contact information for the HOA management company. We can also check for you to see if there are any current or upcoming special assessments.
📋 What HOA Fees Typically Cover
- Gated entry maintenance and security access systems
- Community pool maintenance and upkeep
- Playground and common area maintenance
- Nature trail and lakefront common area landscaping
- Common area landscaping and irrigation throughout community
- Street lighting within the community
- Reserve funds for future capital improvements
📄 HOA Rules & Vacation Rental Policy
Crestwynd Bay is approved for short-term vacation rental use, which is a defining feature of the community's investment appeal. Specific rules regarding rental duration minimums, guest policies, and parking are governed by the current HOA documents. Please contact us for the current governing documents and rental policy details.
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Tanya Cheng
