Watermarke and Castaway
Approximately 2,102–2,263 square feet with courtyard pool and garage. Compare end or interior position, parking, pool and condition.
West Kissimmee · Private-pool resort homes
Windsor at Westside 5-Bedroom Properties
Explore exact 5-bedroom Windsor at Westside properties with live MLS listings and guidance on townhome versus detached-home type, floor plan, bathrooms, private pool and spa, deck, outlook, furniture, HOA, rental setup and condition.
LocationWest Kissimmee / SR–429
Property typesTownhome + single family
BedroomsExactly 5 bedrooms
Private outdoorPrivate pool typical
Signature amenityLazy river & waterslide
Team DonovanLocal resale specialists
Townhome
Single family
Private pool
Lazy river
Clubhouse
Community overview
Compare 5-bedroom properties across Windsor at Westside
Start with the legal property type because townhomes and detached homes have different plans, exterior responsibilities and resale sets. Then compare bathrooms and suites, ground-floor bedrooms, private pool and spa, deck, rear outlook, parking, furniture, entertainment spaces, HOA obligations, rental framework, systems and condition.
The detached lineup stretches from approximately 2,490 to 4,382 square feet. Townhomes are roughly 2,102 or 2,263 square feet. That range supports personal-use families through large rental groups without leaving the same resort.
The official clubhouse is a true social hub, pairing lazy-river and pool recreation with food, fitness, games and organized activities. Phase, plan, pool exposure, water view, parking and condition still create meaningful resale differences.
Home choices
From efficient townhomes to group-scale villas
Family and extended-group plans
Winstone, Lakeshore, Hideaway and Seashore formats balance detached privacy, covered lanai and substantial guest capacity.
Baymont and Clearwater scale
Approximately 4,000 square feet and above, these plans require close review of systems, furnishings, utilities, cleaning and management.
Plan dimensions and bed/bath counts can differ between records and modified homes. Verify builder plan, county record and current MLS details.
Resort amenities
A full clubhouse day without leaving home
〰
Lazy river and waterslide
The zero-entry pool, waterslide, lazy river, hot tub and children’s water playground anchor the outdoor experience.
⌂
10,000 sq ft clubhouse
The official clubhouse includes an activity center, free game room, gym and rentable meeting or event facilities.
★
Tu Casa Bar & Lounge
Food and beverage service, poolside dining and scheduled activities add a managed-resort feel.
Operating hours, menu, events, cabanas, parking fees, amenities and access rules can change. Confirm current details directly.
Getting around
Approximate driving times
Planning estimates only. US–192, SR–429, I–4 traffic, parking and attraction entrances can materially affect travel.
5–10 minGroceries and dining
15–25 minWalt Disney World area
25–35 minSeaWorld Orlando
30–45 minUniversal Orlando Resort
30–45 minOrlando International Airport
NearbySR–429 access
NearbyUS–192 services
NearbyGolf courses
Ownership intelligence
Match the property type to the operating plan
| Property and plan | Confirm phase, legal type, plan, heated area, bedrooms, lot or townhome position, parking, pool and comparable sales. |
|---|---|
| Private pool | Inspect shell, surface, screen or courtyard, deck, heater, pump, filter, controls, spa, drainage and safety barrier. |
| Association | Review declarations, amendments, rules, budget, reserves, insurance, assessments, minutes, projects and litigation. |
| Vacation rental | Verify licensing, occupancy, parking fees, quiet hours, pets, platforms, guest registration and management requirements. |
| Home systems | Inspect roof, HVAC zones, water heaters, plumbing, electrical, appliances, windows, doors and fire-safety equipment. |
| Furniture and themes | Document every item that conveys and assess bedroom themes, games, theater equipment and replacement cost. |
| Operating costs | Model utilities, pool and lawn service, cleaning, repairs, insurance, taxes, dues, supplies and management. |
| Rental evidence | Review statements, bookings, owner use, rate and occupancy history, reviews and management-contract transferability. |
Explore Windsor at Westside
Compare type, plan and pool
Buyer and seller strategy
Clear guidance for both sides
For buyers
Compare property type, plan, pool, lot or position, condition, costs, furniture, rental evidence and management.
Plan your purchase →For sellers
Present plan, pool, view, themed spaces, upgrades, dues, furnishings and rental performance accurately.
Request a selling strategy →For overseas owners
Coordinate access, preparation, contracts and closing remotely, with specialist FIRPTA or tax guidance where appropriate.
Talk with Team Donovan →Live and exact from the MLS
Windsor at Westside 5-bedroom properties for sale
This search uses an exact 5-bedroom MLS filter. Compare legal type, plan, baths, pool, deck, outlook, parking, furniture, HOA, rental setup and condition.
Windsor at Westside 5-Bedroom Properties for Sale
Frequently asked questions
5-bedroom Windsor at Westside buyer questions
What property types are available at Windsor at Westside?
The community includes four- and five-bedroom townhomes plus detached single-family homes that commonly range from five to nine bedrooms.
Do both home types have private pools?
Yes. Townhomes commonly have private courtyard pools, while detached homes have screened pools and covered lanais. Pool, spa, heat and exposure vary.
What amenities are available?
The official resort currently promotes a 10,000-square-foot clubhouse, zero-entry pool, waterslide, lazy river, hot tub, children’s water playground, activity center, game room, gym and Tu Casa Bar & Lounge.
Can owners use short-term rentals?
Vacation rental use is established, but buyers must verify current association rules, Osceola County licensing, occupancy, parking, pets, platforms and management requirements.
How large are the townhomes?
The four-bedroom Watermarke is approximately 2,102 square feet and the five-bedroom Castaway approximately 2,263 square feet. Verify the specific plan and county record.
How large are the detached homes?
Established plans range from roughly 2,490-square-foot five-bedroom homes to approximately 4,382-square-foot nine-bedroom homes, with several six- to eight-bedroom choices between.
Are homes sold furnished?
Many vacation resales are offered furnished and may include themed rooms, theaters or games, but every inclusion and condition should be documented.
How does Team Donovan help at Windsor at Westside?
We help buyers compare property type, plan, pool, lot, condition, furnishings and rental setup, and help sellers present those differences accurately.
Compare 5-bedroom Windsor at Westside properties with clarity
Team Donovan combines detailed vacation-home knowledge with straightforward advice from property-type comparison through closing.
Talk with Team Donovan