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.

Windsor at Westside Private-Pool Homes for Sale | Team Donovan, $400,000

Active

$428,000

WINDSOR AT WESTSIDE PH 3

2414 Dubai St, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Residential Townhouse MLS® # O6414579

Active

$425,000

WINDSOR/WESTSIDE PH 1

8932 Adriatico Ln, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Residential Townhouse MLS® # O6411777

Active

$425,000

▼ $20,000 WINDSOR AT WESTSIDE PH 3 PB 27 PGS 158-162 LOT 101

2436 Dubai St, KISSIMMEE

5 Beds 4 Baths 2,263 SqFt Residential Townhouse MLS® # O6417398

Active

$424,900

▼ $25,100 WINDSOR AT WESTSIDE PH 1

2070 Rome Dr, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Residential Townhouse MLS® # O6426610

Active

$424,000

▼ $20,000 WINDSOR AT WESTSIDE

2427 Dubai St, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Residential Townhouse MLS® # S5123971

Active

$420,000

WINDSOR AT WESTSIDE PH 2B

8875 Geneve Ct, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Residential Townhouse MLS® # O6422639

Active

$419,000

▼ $21,000 WINDSOR AT WESTSIDE PH 3

2428 Dubai St, KISSIMMEE

5 Beds 4 Baths 2,263 SqFt Residential Townhouse MLS® # O6233761

Active

$416,999

WINDSOR AT WESTSIDE PH 1

1987 Majorca Dr, KISSIMMEE

4 Beds 4 Baths 2,263 SqFt Residential Townhouse MLS® # O6397361

Active

$412,900

WINDSOR AT WESTSIDE

2015 Majorca Dr, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Residential Townhouse MLS® # S5148415

Active

$410,000

▼ $40,000 WINDSOR/WESTSIDE-PH 3

2407 Dubai St, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Residential Townhouse MLS® # O6398836

Active

$409,900

WINDSOR AT WESTSIDE

8899 Geneve Ct, KISSIMMEE

4 Beds 4 Baths 2,102 SqFt Residential Townhouse MLS® # O6427755

Active

$409,000

▼ $20,900 WINDSOR AT WESTSIDE

8944 Sydney Ave, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Residential Townhouse MLS® # O6306929

Windsor at Westside Private-Pool Homes for Sale, $400,000 - $500,000

$428,000

2414 Dubai St, KISSIMMEE

$425,000

8932 Adriatico Ln, KISSIMMEE

$425,000

2436 Dubai St, KISSIMMEE

$424,900

2070 Rome Dr, KISSIMMEE

$424,000

2427 Dubai St, KISSIMMEE

$420,000

8875 Geneve Ct, KISSIMMEE

$419,000

2428 Dubai St, KISSIMMEE

$416,999

1987 Majorca Dr, KISSIMMEE

$412,900

2015 Majorca Dr, KISSIMMEE

$410,000

2407 Dubai St, KISSIMMEE

$409,900

8899 Geneve Ct, KISSIMMEE

$409,000

8944 Sydney Ave, KISSIMMEE