Windsor Island Resort

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

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4433 Kaipo Road, DAVENPORT

$1,250,000

↓ $35,000

4433 Kaipo Road, DAVENPORT

10 Beds 8 Baths 4,383 SqFt Residential MLS® # O6221336
2126 Lelani Circle, DAVENPORT

$1,250,000

2126 Lelani Circle, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6150115
4141 Lana Avenue, DAVENPORT

$1,199,000

4141 Lana Avenue, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # S5117025
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3083 Mahalo Drive, DAVENPORT

$1,150,000

3083 Mahalo Drive, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6270285
4101 Lana Avenue, DAVENPORT

$1,150,000

4101 Lana Avenue, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # S5116126
3625 Lily Lane, DAVENPORT

$1,150,000

3625 Lily Lane, DAVENPORT

8 Beds 7 Baths 4,036 SqFt Residential MLS® # O6239189
4289 Lana Avenue, DAVENPORT

$1,099,000

4289 Lana Avenue, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6191499
3743 Lana Avenue, DAVENPORT

$1,050,000

↓ $100,000

3743 Lana Avenue, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6236050
4494 Kaipo Road, DAVENPORT

$1,049,900

↓ $40,100

4494 Kaipo Road, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6198330
2260 Lelani Circle, DAVENPORT

$1,030,000

2260 Lelani Circle, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6244611
2236 Lelani Circle, DAVENPORT

$1,030,000

↓ $100,000

2236 Lelani Circle, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6152222
2210 Lelani Circle, DAVENPORT

$1,000,000

2210 Lelani Circle, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6241834
3728 Lana Avenue, DAVENPORT

$999,999

↓ $100,001

3728 Lana Avenue, DAVENPORT

8 Beds 6 Baths 4,036 SqFt Residential MLS® # L4941084
2191 Lelani Circle, DAVENPORT

$999,000

2191 Lelani Circle, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6244538
2186 Lelani Circle, DAVENPORT

$999,000

↓ $51,000

2186 Lelani Circle, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # S5102888
3553 Lavender Drive, DAVENPORT

$999,000

↓ $76,000

3553 Lavender Drive, DAVENPORT

9 Beds 6 Baths 4,399 SqFt Residential MLS® # O6175204
3004 Mahalo Drive, DAVENPORT

$995,000

↓ $95,000

3004 Mahalo Drive, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # OM671799
4189 Lana Avenue, DAVENPORT

$990,000

↓ $50,000

4189 Lana Avenue, DAVENPORT

8 Beds 7 Baths 4,025 SqFt Residential MLS® # O6163649
4149 Lana Avenue, DAVENPORT

$985,000

4149 Lana Avenue, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6195199
3209 Lilac Way, DAVENPORT

$979,000

↓ $10,000

3209 Lilac Way, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # S5111293
3545 Lavender Drive, DAVENPORT

$975,000

↓ $75,000

3545 Lavender Drive, DAVENPORT

9 Beds 6 Baths 4,398 SqFt Residential MLS® # O6184803
4457 Kaipo Road, DAVENPORT

$965,000

4457 Kaipo Road, DAVENPORT

10 Beds 8 Baths 4,398 SqFt Residential MLS® # O6249985
3605 Lily Lane, DAVENPORT

$963,900

↓ $1,099

3605 Lily Lane, DAVENPORT

10 Beds 8 Baths 4,447 SqFt Residential MLS® # S5106703
2131 Lelani Circle, DAVENPORT

$960,000

2131 Lelani Circle, DAVENPORT

9 Beds 6 Baths 4,393 SqFt Residential MLS® # O6244474
2031 Lelani Circle, DAVENPORT

$950,000

↓ $40,000

2031 Lelani Circle, DAVENPORT

10 Beds 8 Baths 4,399 SqFt Residential MLS® # O6238410
4473 Kaipo Road, DAVENPORT

$949,000

↓ $16,000

4473 Kaipo Road, DAVENPORT

8 Beds 6 Baths 4,036 SqFt Residential MLS® # S5104740
3032 Mahalo Drive, DAVENPORT

$930,000

3032 Mahalo Drive, DAVENPORT

10 Beds 8 Baths 4,406 SqFt Residential MLS® # O6257885
4412 Kaipo Road, DAVENPORT

$928,000

↓ $40,000

4412 Kaipo Road, DAVENPORT

7 Beds 6 Baths 3,281 SqFt Residential MLS® # L4941083
4361 Lana Avenue, DAVENPORT

$925,000

4361 Lana Avenue, DAVENPORT

10 Beds 8 Baths 4,383 SqFt Residential MLS® # O6244685
4424 Kaipo Road, DAVENPORT

$924,900

4424 Kaipo Road, DAVENPORT

7 Beds 6 Baths 3,286 SqFt Residential MLS® # O6233962

Windsor Island Resort

Orlando Investment Properties Communities

Windsor Island Resort Real Estate Market Statistics

Average Price $772K
Lowest Price $475K
Highest Price $1.3M
Total Listings 112
Avg. Days On Market 152
Avg. Price/SQFT $3.1K
List to Sell Price Percentage 96 %

Property Types (active listings)


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: PulteGroup
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

Hospitals

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

*Distances are approximately measured from Windsor Island Resort community entrance

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