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Windsor Island Resort Kissimmee Vacation Homes for Sale Windsor Island Resort Real Estate Windsor Island Resort Orlando Vacation Homes for Sale Windsor Island Resort Orlando Investment Property Real Estate

A modern vacation home set within an exciting five-star luxury resort, multiple resort-style amenities, and convenience to Orlando’s world-class attractions are just some of stellar features of Windsor Island Vacation Community in Kissimmee. This Pulte Homes community offers some of the largest vacation homes you’ll find, from five bedroom townhomes to 10-bedroom single-family homes.

Windsor Island Resort Homes for Sale

Windsor Island Resort Homes for Sale

104 Properties Found. Page 1 of 7.
Photo of Listing #O6225531

4237 Lana Avenue

MLS® # O6225531
8 Beds, 6 Baths, 4,028 Sf
Photo of Listing #O6223775

4453 Kaipo Road

MLS® # O6223775
8 Beds, 6 Baths, 4,025 Sf
Photo of Listing #O6219052

4417 Kaipo Road

MLS® # O6219052
10 Beds, 8 Baths, 4,399 Sf
Photo of Listing #O6224151
MLS® # O6224151
6 Beds, 5 Baths, 3,111 Sf
Photo of Listing #O6213652

3954 Lana Avenue

MLS® # O6213652
5 Beds, 5 Baths, 2,283 Sf
Photo of Listing #O6223537

261 Jetty Way

MLS® # O6223537
5 Beds, 5 Baths, 2,283 Sf
Photo of Listing #O6222995
MLS® # O6222995
5 Beds, 4 Baths, 2,496 Sf
Photo of Listing #O6221892

4150 Lana Avenue

MLS® # O6221892
5 Beds, 5 Baths, 2,263 Sf
Photo of Listing #O6221210

3633 Lily Lane

MLS® # O6221210
10 Beds, 8 Baths, 4,399 Sf
Photo of Listing #O6221336

4433 Kaipo Road

MLS® # O6221336
10 Beds, 8 Baths, 4,383 Sf
Photo of Listing #S5108067

3907 Lana Avenue

MLS® # S5108067
7 Beds, 6 Baths, 3,281 Sf
Photo of Listing #O6220558
MLS® # O6220558
5 Beds, 6 Baths, 2,594 Sf
Photo of Listing #O6220252

4057 Lana Avenue

MLS® # O6220252
7 Beds, 6 Baths, 3,281 Sf
Photo of Listing #O6214848
Reduced 2.7%
MLS® # O6214848
6 Beds, 5 Baths, 3,102 Sf
Photo of Listing #S5107589
MLS® # S5107589
5 Beds, 6 Baths, 2,621 Sf

This gated community, located off of Highway 27 and Sand Mine Road in Davenport, is a dream come true for buyers who not only want space for the whole family, but who are also looking for an investment property and short term rental income, not to mention luxurious accommodations and top-notch resort amenities. 

With nine distinct designs to choose from, the 136 townhomes and 464 single-family homes here each feature modern, sophisticated décor, open concepts, and private pools or courtyards. Quality finishes include brick paver driveways, granite in the kitchen and baths, stainless steel appliances and shingle roofs. Each is designed to accommodate multiple guests and provide the very best when it comes to entertaining, but also focuses on the need for individual privacy.

Windsor Island Resort Private Vacation Home Pool

When not enjoying the comforts of home, residents have access to multiple amenities right outside their front door, from mini-golf, to a lazy river, to a clubhouse that includes a fitness center and game room. Nightly fireworks can be seen from the fire pit, which is also a great place to get to know neighbors. A sand volleyball court and basketball court are perfect for getting in some afternoon activity. And the spa and hammock garden are ideal for some rest and relaxation. 

This is a vacation-lovers paradise and one that is ripe with opportunities for those wanting to make short term rental income while not on vacation. Don’t delay. Find out how you can own a piece of this one-of-a-kind resort today!

Windsor Island Resort Community Site & Floor Plans

PDF Icon Windsor Island Resort Site Plan

PDF Icon Windsor Island Resort Floor Plans

Windsor Island Resort Community Information

Location: Sand Mine Road East of US-27
Year Built: 2020 - Homesites Available
Builder: Pulte Group
Number of Units: 617
Square Footage: 2,263 - 4,398
HOA: Yes
Community Amenities: Resort-style swimming pool, waterslide, pool bar, cabanas, spa, clubhouse, fitness center, game room, mini-golf, lazy river, beach volleyball, basketball court, fire pit, cornhole, hammock garden, walking paths, cafe, hammock garden, firework views, fully maintained landscaping and lawn irrigation.

Dining and Shopping

  • Berry Town Center with Publix Super Market – Distance: 1 mile 

  • Ridgeview Plaza – Distance: 4.5 miles
Posner Park Shopping Center – Distance: 6.5 miles
Orange Lake Towne Center with Grocery Store – Distance: 6.5 miles

  • Deer Creek Crossings Shopping Center – Distance: 7 miles
Champions Gate Village with Grocery Store – Distance: 7 miles
Rolling Oak Commons with Grocery Store, Dining & Services - Distance: 7 miles
Formosa Gardens Village – Distance: 7 miles
Celebration Town Center – Distance: 13 miles
  • Restaurant Row - Distance: 22 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 25.5 Miles
Downtown Orlando - Distance: 29 miles

Parks and Recreation

  • Florida Highlands Reserve: 1 mile

  • Northeast Regional Park – Distance: 1.5 miles

  • Polo Park – Distance: 3 miles
  • Loughman Park - Distance: 11.5 miles

  • Walt Disney World Resort – Distance: 11 miles

  • Universal Studios – Distance: 23 miles

  • SeaWorld – Distance - 21 miles


  • AdventHealth Celebration – Distance: 11.5 miles
  • Orlando Health Southlake Hospital – Distance: 18 miles

*Distances are approximately measured from Windsor Island Resort community entrance

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on July 22nd, 2024 at 7:19am EDT.