Davenport · Polk County · Gated

Windsor at Westside Homes for Sale

Resort-style gated community near Disney with private pools and vacation rental potential.

Live ListingsFrom $400KEst. 2015Gated
Active Listings

Homes for sale in Windsor at Westside

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About

Inside Windsor at Westside

Windsor at Westside is a gated vacation home community developed by Pulte Homes between 2015 and 2020 in the Four Corners area near Davenport and Kissimmee, roughly 20 minutes from Walt Disney World. The resort comprises over 600 units of townhomes and single-family homes ranging from 4 to 9 bedrooms, with pricing that started at approximately $400,000 for townhomes and extended to $515,000 and beyond for larger single-family homes during the initial development phase.

The community features Mediterranean-style architecture with barrel tile roofs, brick paver driveways, and uniform aesthetic standards. All homes include private heated pools and screened lanai areas. Floor plan options include the Castaway, Hideaway, Seashore, Baymont, and Clearwater models, offering buyers flexibility in size and layout. Many homes are designed and marketed as turnkey vacation rental investments, with open floor plans, multiple en-suite bedrooms, and gaming rooms.

Homeowners Association fees range from $374 to $410 per month depending on lot size and homesites, and include high-speed internet, basic cable, lawn care, landscaping, irrigation, pest control, gated security, and access to community amenities. These fees represent significant value given the included services and resort-level facilities.

The centerpiece of Windsor at Westside is a 10,000 square-foot clubhouse with a zero-entry resort-style pool featuring a waterslide, lazy river, and kids’ water playground. Additional amenities include a state-of-the-art fitness center, volleyball courts, basketball courts, sand volleyball, arcade, and the Tu Casa Tiki bar serving poolside dining. The gated community operates with 24-hour staffed security and a guard gate, providing residents and guests with peace of mind. Short-term rentals are permitted, making the community attractive to investors seeking income-generating vacation home properties.

Community at a Glance

The facts

Total Homes
600
HOA / Month
$374-$410
School District
Polk County Public Schools
Questions, Answered

Frequently asked

What is the price range for homes in Windsor at Westside?

New construction pricing at Windsor at Westside started around $400,000 for 4-5 bedroom townhomes and ranged up to $515,000 and beyond for 8-9 bedroom single-family homes. Current resale prices may vary. Contact a Market Connect Realty agent for current market pricing and available inventory.

Is Windsor at Westside a gated community?

Yes, Windsor at Westside is a fully gated community with 24-hour staffed security and a guard gate. The gated design provides controlled access and enhanced security for residents and their guests, contributing to the resort-style community atmosphere.

What schools are zoned for Windsor at Westside?

School zoning for Windsor at Westside addresses in Davenport/Kissimmee can vary. To determine specific elementary, middle, and high schools zoned for a particular address, check Polk County Public Schools GeoZone tool at polkschoolsfl.com/schoolzones or contact Pupil Accounting at 863-519-7600.

What are the HOA fees in Windsor at Westside?

HOA fees range from $374 to $410 per month depending on lot size. These fees include high-speed internet, basic cable, lawn care, landscaping, pest control, exterior maintenance, and access to all community resort amenities including the clubhouse, pools, fitness center, and sports courts.

What amenities does Windsor at Westside offer?

Windsor at Westside features a 10,000 sq ft clubhouse, zero-entry resort-style pool with waterslide and lazy river, kids' water playground, fitness center, volleyball courts, basketball courts, sand volleyball, video arcade, tiki bar with restaurant, and 24-hour gated security. All homes include private heated pools and screened lanai areas.

How many homes are in Windsor at Westside?

Windsor at Westside contains over 600 residential units total, comprised of both 4-5 bedroom townhomes and 5-9 bedroom single-family homes. The community includes approximately 219 single-family homes on 40-foot homesites and 285 single-family homes on 50-foot homesites, plus additional townhome units.

Is short-term rental allowed in Windsor at Westside?

Yes, short-term rentals are permitted at Windsor at Westside. The community is marketed as a vacation rental resort destination, and many homes are designed and sold as turnkey rental-ready properties. This makes it attractive for investors seeking income-generating vacation home investments near Disney.

What year was Windsor at Westside developed?

Pulte Homes began development of Windsor at Westside in 2015, with closeout and buildout completion occurring around 2020. The community was developed in phases to accommodate the 600+ unit build-out while maintaining quality construction and consistent design standards.