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Windsor at Westside Resort Vacation Homes for Sale

1940 Nice Court, Kissimmee image
1940 Nice Court, Kissimmee $749,000

Luxury Villa – “Lord of the Manor” – Minutes from Disney Experience elevated comfort and themed luxury at “Lord of the Manor,” a fully renovated 9-bedroom, 6-bathroom ...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
8887 Menton Loop, Kissimmee image
8887 Menton Loop, Kissimmee $739,999

Turnkey investment opportunity in a highly sought-after resort-style community just minutes from Disney World! This fully furnished home is a heavily booked short-term re...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside Ph 1 SubDv.
  • 34747 Zip Code
2451 Luxor Drive, Kissimmee image
2451 Luxor Drive, Kissimmee $720,000

Welcome to this beautiful 8-bedroom, 6-bathroom vacation home in the highly desirable Windsor at Westside Resort. Perfectly located in a quiet section of the community, t...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Phase 3 SubDv.
  • 34747 Zip Code
2100 Rome Drive, Kissimmee image
2100 Rome Drive, Kissimmee $720,000

Welcome to this exceptional 7-bedroom, 5-bathroom vacation home located in the highly desirable Windsor at Westside Resort. This fully furnished property is turn-key and ...

  • 7 Beds
  • 6 Baths
  • Windsor At Westside Ph 1 Pb 23 Pg 112-118 Lot 100 SubDv.
  • 34747 Zip Code
2112 Morocco Way, Kissimmee image
2112 Morocco Way, Kissimmee $699,900

7-Bedroom 5.5-Bathroom fully furnished home at Windsor at Westside a Gated Community. Located around 15 minutes from Disney World, Master Bedroom in the First Floor. Reso...

  • 7 Beds
  • 6 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
8879 Qin Loop, Kissimmee image
8879 Qin Loop, Kissimmee $699,000

Private Wooded Lot | 8 Bedrooms | 6 Bathrooms | Heated Pool & Spa | 12-Seat Movie Theater | Game Room | Fully Furnished Discover the perfect blend of privacy, luxury, ...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
2105 Malta Terrace, Kissimmee image
2105 Malta Terrace, Kissimmee $699,000

Welcome to this stunning 8-bedroom, 6-bathroom vacation home in the highly sought-after Windsor at Westside gated resort community just 2.5 miles from Walt Disney World. ...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8832 Macapa Drive, Kissimmee image
8832 Macapa Drive, Kissimmee $699,000 ▼

Welcome to the best of Florida resort life! This 8 bedroom 6 bathroom house has all you can ask for and more! Fully furnished, this home is ready for an immediate occupa...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
2137 Malta Terrace, Kissimmee image
2137 Malta Terrace, Kissimmee $695,000

Discover this stunning 8-bedroom, 6-bathroom luxury home located in the highly sought-after Windsor at Westside Resort, just 15 minutes from Walt Disney World! This prope...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph1 SubDv.
  • 34747 Zip Code
1517 Mumbai Way, Kissimmee image
1517 Mumbai Way, Kissimmee $690,000 ▲

Welcome to 1517 Mumbai Way, a spacious and beautifully positioned 6-bedroom, 4.5-bathroom pool home in the highly sought-after Windsor at Westside community! Built in 201...

  • 6 Beds
  • 5 Baths
  • Windsor/Westside Ph 2b SubDv.
  • 34747 Zip Code
8815 Macapa Drive, Kissimmee image
8815 Macapa Drive, Kissimmee $689,000

Enjoy breathtaking pond views and exceptional backyard privacy in this stunning 8-bedroom, 5.5-bathroom home located in the highly sought-after Windsor at Westside commun...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
8812 Macapa Drive, Kissimmee image
8812 Macapa Drive, Kissimmee $680,000

Discover an exceptional opportunity to own this beautifully furnished 8-bedroom, 6-bathroom pool home in the highly sought-after GATED resort community of Windsor at West...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
1682 Lima Avenue, Kissimmee image
1682 Lima Avenue, Kissimmee $679,000

Welcome to this stunning 8-bedroom, 6-bathroom vacation home located in the highly desirable resort community of Windsor at Westside. Built in 2019, this turn-key propert...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8817 Corcovado Drive, Kissimmee image
8817 Corcovado Drive, Kissimmee $678,000

Experience the ultimate blend of luxury, comfort, and investment potential in this stunning fully furnished 9-bedroom, 6-bathroom lakefront home. Turnkey and short-term r...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8825 Rhodes Street, Kissimmee image
8825 Rhodes Street, Kissimmee $675,000

Welcome to 8825 Rhodes Street, 4041sqft beautifully maintained and fully furnished 8-bedroom, 6-bathroom home located within the highly sought-after gated Windsor at West...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
1941 Nice Court, Kissimmee image
1941 Nice Court, Kissimmee $670,000

Take a look at this unique amazing property at 1941 Nice Ct located in Windsor Westside, one of Disney’s most popular short term rental vacation home communities. This in...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a Rep SubDv.
  • 34747 Zip Code
1908 Nice Court, Kissimmee image
1908 Nice Court, Kissimmee $669,990 ▼

Welcome to this spectacular 9-bedroom, 6-bathroom fully furnished pool home located in the highly desirable Windsor at Westside Resort! Built in 2018, this spacious two-s...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
1599 Lima Avenue, Kissimmee image
1599 Lima Avenue, Kissimmee $665,000 ▼

Beautifully decorated and Spacious 8-bedroom, 6-bathroom vacation home just minutes from Disney and major attractions. Ideal for short-term rental, investment, or persona...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
1690 Lima Avenue, Kissimmee image
1690 Lima Avenue, Kissimmee $660,000 ▼

Turnkey 8-bedroom, 6-bath fully furnished pool home located in the highly desirable Windsor at Westside Resort. This well-maintained property offers over 4,000 sq ft of l...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8896 Bengal Court, Kissimmee image
8896 Bengal Court, Kissimmee $660,000

Welcome to 8896 Bengal Court, an exceptional opportunity to own a residence in one of Central Florida’s most sought-after destinations. Positioned in the desirable Kissim...

  • 5 Beds
  • 6 Baths
  • Windsor/Westside-Ph 2a SubDv.
  • 34747 Zip Code
2183 Tripoli Ct, Kissimmee image
2183 Tripoli Ct, Kissimmee $659,000 ▼

This spacious fully furnished 9-bedroom, 6-bathroom pool home is located in the sought-after Windsor at Westside Resort. One of the largest floor plans in the community,...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
2147 Tripoli Court, Kissimmee image
2147 Tripoli Court, Kissimmee $658,000 ▼

The largest home on one of the best lots in entire Windsor at Westside resort. This fully furnished/equipped home with private pool deck, is just stone throw away from fa...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
1610 Lima Avenue, Kissimmee image
1610 Lima Avenue, Kissimmee $655,000

Imagine pulling into a community where every day feels like you're on vacation. Located in the 24/7 guard-gated community of Windsor at Westside, this sprawling 8-bedroom...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
1844 Gobi Drive, Kissimmee image
1844 Gobi Drive, Kissimmee $655,000

Priced to sell! This fully furnished 6 bedroom, 4.5 bathroom vacation home is already operating and generating short term rental income, featuring three themed bedrooms, ...

  • 6 Beds
  • 5 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
1638 Lima Avenue, Kissimmee image
1638 Lima Avenue, Kissimmee $650,000

2025 Gross: $133,345! First available to view Monday Sept 28! Contact your agent today!!! This is the vacation home guests remember! Updates focusing on guests enjoyme...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8853 Rhodes Street, Kissimmee image
8853 Rhodes Street, Kissimmee $645,000 ▼

Welcome to one of the largest homes on one of the most desirable lots in Windsor at Westside Resort! This impressive, fully furnished and equipped vacation home offers an...

  • 9 Beds
  • 6 Baths
  • Windsor/Westside-Ph 1 SubDv.
  • 34747 Zip Code
8924 Bengal Court, Kissimmee image
8924 Bengal Court, Kissimmee $639,900 ▼

Welcome to this spacious 9-bedroom, 6-bath pool home located in the sought-after Windsor at Westside Resort community of Kissimmee! Offering approximately 4,391 square fe...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
1614 Lima Avenue, Kissimmee image
1614 Lima Avenue, Kissimmee $639,900 ▼

Spacious 8-bedroom, 6-bathroom single-family home located in the gated community Windsor at Westside Resort. This two-story home offers a functional layout with an open-c...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
1885 Gobi Drive, Kissimmee image
1885 Gobi Drive, Kissimmee $629,999 ▼

OVER $200K IN CUSTOM RENOVATIONS & THEMED UPGRADES! Welcome to the ultimate turn-key investment property at 1885 Gobi Drive in the premier, guard-gated community of Winds...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside, Windsor At Westside SubDv.
  • 34747 Zip Code
1829 Gobi Drive, Kissimmee image
1829 Gobi Drive, Kissimmee $629,000

Welcome to this exceptional 8-bedroom, 6-bathroom resort home in the highly desirable Windsor at Westside community, where stunning pond views, privacy, and resort-style ...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
1744 Lima Avenue, Kissimmee image
1744 Lima Avenue, Kissimmee $589,000

Experience the ultimate Orlando getaway in this beautifully appointed 7-bedroom, 5.5-bath vacation home located in the highly desirable Windsor at Westside Resort, just m...

  • 7 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
1627 Lima Ave, Kissimmee image
1627 Lima Ave, Kissimmee $580,000 ▼

Welcome to this beautiful 7 Bed/ 5.5 Bath luxury vacation/investment home with WATERVIEW, nested in one of the most popular resort in Orlando: Windsor at Westside. This T...

  • 7 Beds
  • 6 Baths
  • Windsor/Westside-Ph 2a SubDv.
  • 34747 Zip Code
8900 Prague Way, Kissimmee image
8900 Prague Way, Kissimmee $579,000 ▼

Welcome to this stunning 7-bedroom, 5-bathroom pool home situated on a spacious corner lot in the highly sought-after Windsor at Westside Resort. Ideal for large families...

  • 7 Beds
  • 6 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
8956 Zurich Lane, Kissimmee image
8956 Zurich Lane, Kissimmee $575,000

Location, location!!!!This fully furnished, turn-key 7-bedroom, 5.5-bathroom home offers 3,314 sq ft at Windsor at Westside a Gated Community. Enjoy an open-concept kitch...

  • 7 Beds
  • 6 Baths
  • Windsor At Westside Ph 3a SubDv.
  • 34747 Zip Code
8824 Bengal Court, Kissimmee image
8824 Bengal Court, Kissimmee $570,000

Welcome to 8824 Bengal Court, a FULLY FURNISHED 8-BEDROOM, 6-BATHROOM home in the prestigious GUARD-GATED WINDSOR AT WESTSIDE RESORT. Built in 2019, this exceptional prop...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b-1 SubDv.
  • 34747 Zip Code
1724 Lima Ave, Kissimmee image
1724 Lima Ave, Kissimmee $570,000 ▼

New Price! Luxurious 7-Bed, 5.5-Bath Retreat in Windsor at Westside! Nestled on a premium lot in the coveted Windsor at Westside gated community, this fully furnished 7-...

  • 7 Beds
  • 6 Baths
  • Windsor/Westside-Ph 2a SubDv.
  • 34747 Zip Code
8877 Bengal Court, Kissimmee image
8877 Bengal Court, Kissimmee $565,000

Spacious 5-bedroom, 5.5-bathroom pool home located just 8 miles from Walt Disney World. This open-concept property features a modern kitchen equipped with stainless steel...

  • 5 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
1836 Nice Court, Kissimmee image
1836 Nice Court, Kissimmee $560,000 ▲

Short Sale. Welcome to your own slice of paradise in the highly sought-after, guard-gated Windsor at Westside Resort! This beautifully updated and fully furnished 8-bedro...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside-Ph 2a SubDv.
  • 34747 Zip Code
1885 Nice Court, Kissimmee image
1885 Nice Court, Kissimmee $559,000

Welcome to resort-style living at its finest in the highly sought-after Windsor at Westside Resort! This beautifully maintained 6-bedroom, 4.5-bath pool home is offered f...

  • 6 Beds
  • 5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
9013 Rhodes Street, Kissimmee image
9013 Rhodes Street, Kissimmee $550,000 ▼

Located in the exclusive gated community of Windsor at Westside, this beautiful two-story residence, sold fully furnished, is the perfect combination of comfort, sophisti...

  • 6 Beds
  • 5 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
1861 Nice Ct, Kissimmee image
1861 Nice Ct, Kissimmee $550,000 ▼

INVESTOR ALERT — NOW $550,000! TURNKEY 7-BEDROOM SHORT-TERM RENTAL | WINDSOR AT WESTSIDE | PRIVATE POOL | MINUTES TO DISNEY 7 BEDROOMS. 5+ BATHROOMS. 3,281 SQ. FT. FUL...

  • 7 Beds
  • 6 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
1917 Nice Court, Kissimmee image
1917 Nice Court, Kissimmee $549,990

Welcome to this stunning 5-bedroom, 4-bathroom home located in the highly desirable gated community of Windsor at Westside in Kissimmee. This spacious residence offers ap...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
8956 Rhodes Street, Kissimmee image
8956 Rhodes Street, Kissimmee $540,000 ▼

Great, great price improvement!! It is really priced to sell quickly!! Beautiful 6 bedroom 4 1/2 bathroom, hideaway open floor plan on a corner lot in the desirable Winds...

  • 6 Beds
  • 5 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
1881 Nice Court, Kissimmee image
1881 Nice Court, Kissimmee $535,000 ▼

HUGE Price Improvement!! Welcome to your dream vacation retreat in the highly sought-after Windsor at Westside Resort! This stunning 7-bedroom, 5.5-bath pool home is pro...

  • 7 Beds
  • 6 Baths
  • Windsor/Westside-Ph 2a SubDv.
  • 34747 Zip Code
1809 Nice Court, Kissimmee image
1809 Nice Court, Kissimmee $529,000

Escape to this exceptional vacation retreat located within the popular Windsor at Westside Resort, one of Central Florida’s premier resort communities. Offering 3,142 squ...

  • 6 Beds
  • 5 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
2440 Tangier Drive, Kissimmee image
2440 Tangier Drive, Kissimmee $525,000

Located within the highly sought-after Windsor at Westside gated resort community, this fully furnished home offers flexibility as a primary residence, vacation getaway, ...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8936 Prague Way, Kissimmee image
8936 Prague Way, Kissimmee $524,900 ▼

Just reduced $25,000! PRICED BELOW MARKET VALUE. This fully furnished property with EV station is within walking distance of the clubhouse. Rental-ready 6-bedroom proper...

  • 6 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
8904 Prague Way, Kissimmee image
8904 Prague Way, Kissimmee $515,000

Located in one of Central Florida's premier resort communities, this beautifully maintained and fully furnished 5-bedroom, 4-bath pool home offers the perfect blend of co...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
1921 Nice Court, Kissimmee image
1921 Nice Court, Kissimmee $510,000 ▼

Fully Furnished Pool and Spa Home. A fantastic choice to be your Vacation Home or Rental Property in the Windsor at Westside Resort! 6 Bedrooms - 4.5 Bathrooms and a Gorg...

  • 6 Beds
  • 5 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
1888 Gobi Drive, Kissimmee image
1888 Gobi Drive, Kissimmee $499,900 ▼

Welcome to the ultimate Florida lifestyle in the highly desirable guard-gated community of winsor at westsite! This stunning, professionally decorated 6 bedroom, 5 bath p...

  • 6 Beds
  • 5 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
2462 Dubai Street, Kissimmee image
2462 Dubai Street, Kissimmee $499,000

Welcome to this beautifully furnished 5-bedroom, 4-bathroom pool home in the sought-after Windsor at Westside Resort! SHORT-TERM RENTAL ALLOWED........ Situated on a desi...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside Ph 3a SubDv.
  • 34747 Zip Code
2429 Dubai Street, Kissimmee image
2429 Dubai Street, Kissimmee — Phase 3 $499,000 ▼

GREAT, GREAT PRICE IMPROVEMENT!! This beautiful home is locate on the third and newest phase of the sought after Windsor at Westside Resort. It boasts 5 bedrooms and 4 ba...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
2417 Dubai Street, Kissimmee image
2417 Dubai Street, Kissimmee — N/A $495,000

Welcome to this beautifully maintained 5-bedroom, 4.5-bathroom home located in the highly sought-after Windsor at Westside Resort in Kissimmee. Whether you're searching f...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
2426 Tangier Drive, Kissimmee image
2426 Tangier Drive, Kissimmee — 2426 $495,000

Welcome to this beautifully maintained, fully furnished 5-bedroom, 4.5-bath townhome with a private screened pool, located in the highly desirable Windsor at Westside Res...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
1512 Mumbai Way, Kissimmee image
1512 Mumbai Way, Kissimmee $490,000 ▼

Check out this beautiful 5-bedroom, 4-bathroom pool home in the highly sought after resort community of Windsor at Westside! This fully furnished home is in great conditi...

  • 5 Beds
  • 4 Baths
  • Windsor/Westside-Ph 2b SubDv.
  • 34747 Zip Code
2430 Tangier Drive, Kissimmee image
2430 Tangier Drive, Kissimmee — 2430 $490,000 ▼

*** INCOME POTENTIAL *** VACATION HOME FULLY FURNISHED. In Excellent condition and beautifully decorated this 5 Bedroom Townhome with a splash pool has all you need for s...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
1857 Nice Court, Kissimmee image
1857 Nice Court, Kissimmee $489,000 ▼

Welcome to a fantastic investment opportunity in the Windsor at Westside resort community! This fully furnished 5-bedroom, 4-bathroom pool home offers a luxurious living ...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8933 Prague Way, Kissimmee image
8933 Prague Way, Kissimmee $489,000 ▼

FULLY FURNISHED | TURNKEY INVESTMENT | RESORT-STYLE COMMUNITY Welcome to this beautiful two-story home located in the highly desirable resort-style community of Windso...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
8931 Zurich Lane, Kissimmee image
8931 Zurich Lane, Kissimmee $483,000 ▼

A fantastic choice to be your Vacation Rental Property in the Windsor at Westside, located in Kissimmee Florida! 5 Bedrooms - 4 Bathrooms and your own Private Pool. Welco...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside Ph 3a SubDv.
  • 34747 Zip Code
8926 Zurich Lane, Kissimmee image
8926 Zurich Lane, Kissimmee $482,900 ▼

Your Dream Vacation Home—Just Minutes from Disney! Imagine owning a fully furnished 5-bedroom home in one of Kissimmee’s most sought-after resort communities—Windsor a...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside Ph 3a SubDv.
  • 34747 Zip Code
8916 Sydney Avenue, Kissimmee image
8916 Sydney Avenue, Kissimmee — 00 $479,000 ▼

Welcome to this beautiful home located at the unique Windsor At Westside. This 5 bedrooms, 4 full bathrooms and 1 half bathroom features an open plan family room, kitchen...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
2452 Dubai St, Kissimmee image
2452 Dubai St, Kissimmee — 1 $474,000 ▼

Welcome to Windsor at Westside! This stunning 5-bedroom, 4.5-bathroom townhome is beautifully decorated and comes fully furnished with top-of-the-line model home furnitur...

  • 5 Beds
  • 5 Baths
  • Wndsor/Westside-Ph 3 SubDv.
  • 34747 Zip Code
8866 Geneve Court, Kissimmee image
8866 Geneve Court, Kissimmee — X $469,000 ▼

Welcome to 8866 Geneve Court, an exceptional 5-bedroom, 4.5-bathroom townhome located in the highly sought-after Windsor at Westside Resort. Beautifully maintained and fu...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8923 Sydney Avenue, Kissimmee image
8923 Sydney Avenue, Kissimmee — 8923 $465,000

Fully Furnished 5-Bedroom Townhome with Heated Private Pool in Prime Kissimmee Location Welcome to this exceptional two-story townhome in the heart of Kissimmee, offer...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
8929 Sydney Avenue, Kissimmee image
8929 Sydney Avenue, Kissimmee — 8929 $460,000

***We have bookings - great investment opportunity!!! This beautiful townhouse at 8929 Sydney Ave in Kissimmee, FL is ready for immediate occupancy and offers exceptional...

  • 5 Beds
  • 5 Baths
  • Windsor/Westside-Ph 3 SubDv.
  • 34747 Zip Code
2402 Dubai Street, Kissimmee image
2402 Dubai Street, Kissimmee — No, $460,000 ▲

This is Windsor at Westside, your new home far from home! This beautiful townhouse features an amazing living room facing the desired pool you crave to see after a day of...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
8879 Geneve Court, Kissimmee image
8879 Geneve Court, Kissimmee — Pulte Group $455,000 ▼

This beautifully maintained home is currently part of a successful short-term rental program, making it an excellent opportunity for both investors and end users. Thought...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8932 Sydney Avenue, Kissimmee image
8932 Sydney Avenue, Kissimmee — 2428 $449,000

TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| END UNIT Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment oppo...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside; Windsor/Westside SubDv.
  • 34747 Zip Code
8942 Sydney Avenue, Kissimmee image
8942 Sydney Avenue, Kissimmee — 2428 $445,000 ▼

TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opp...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside; Windsor/Westside SubDv.
  • 34747 Zip Code
1869 Nice Court, Kissimmee image
1869 Nice Court, Kissimmee $445,000 ▼

Welcome to tastefully designed 5/bed 4/bath home with private pool facing conservation area in the prestige Community Windsor at Westside, zoned for short term vacation r...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
8936 Sydney Avenue, Kissimmee image
8936 Sydney Avenue, Kissimmee — 8936 $445,000

Beautiful fully furnished vacation home located in the highly desirable Windsor at Westside Resort. This property offers an open floor plan, private screened pool and spa...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
8838 Geneve Court, Kissimmee image
8838 Geneve Court, Kissimmee — 8838 $435,000

Welcome to this stunning, fully furnished home located in the highly sought-after gated resort community of Windsor at Westside! Beautifully decorated and meticulously ma...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8907 Sydney Avenue, Kissimmee image
8907 Sydney Avenue, Kissimmee — 8907 $430,000

Turnkey 5-Bedroom Townhome – Short-Term Rental Approved! Welcome to this beautifully furnished 5-bedroom, 4.5-bathroom townhome, thoughtfully designed with fun Mickey Mo...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
8904 Sydney Avenue, Kissimmee image
8904 Sydney Avenue, Kissimmee — 2428 $429,000 ▼

TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment oppor...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside; Windsor/Westside SubDv.
  • 34747 Zip Code
2414 Dubai Street, Kissimmee image
2414 Dubai Street, Kissimmee — 2414 $428,000

Priced to sell! This stunning home sits in the third and newest phase of the sought-after Windsor at Westside Resort, with also a Private Heated Pool. Featuring 5...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
2436 Dubai Street, Kissimmee image
2436 Dubai Street, Kissimmee — N/A $425,000 ▼

Beautiful fully furnished townhouse located in the highly sought-after resort-style community of Windsor at Westside. This 2-story property features an open-concept floor...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside Ph 3 Pb 27 Pgs 158-162 Lot 101 SubDv.
  • 34747 Zip Code
8932 Adriatico Lane, Kissimmee image
8932 Adriatico Lane, Kissimmee — N/A $425,000

Welcome to resort-style living and effortless ownership in this fully furnished end-unit townhome, ideally located just a short 3-minute walk from the community's premier...

  • 5 Beds
  • 5 Baths
  • Windsor/Westside Ph 1 SubDv.
  • 34747 Zip Code
1909 Majorca Drive, Kissimmee image
1909 Majorca Drive, Kissimmee — 1909 $424,999 ▼

Discover the pinnacle of Florida living in this stunning, fully furnished 5-bedroom, 4.5-bathroom townhome, nestled within the highly sought-after Windsor at Westside res...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
2070 Rome Drive, Kissimmee image
2070 Rome Drive, Kissimmee — 2070 $424,900 ▼

Welcome to one of the best-located homes in Windsor at Westside Resort! Situated on a premium corner lot and just steps from the clubhouse, this fully furnished 5-bedroom...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
8875 Geneve Ct, Kissimmee image
8875 Geneve Ct, Kissimmee — 8911 $420,000

Stunning 5-bedroom, 4.5-bath vacation home in the highly sought-after Encore at Reunion! Located at 8875 Geneve Ct, Kissimmee, this beautifully furnished property is the ...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
2428 Dubai Street, Kissimmee image
2428 Dubai Street, Kissimmee — 2428 $419,000 ▼

Nestled Townhouse in Windsor at Westside, one of Kissimmee's premier short-term rental communities, this FULLY FURNISHED townhouse is your oasis of luxury and relaxation....

  • 5 Beds
  • 4 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
1987 Majorca Drive, Kissimmee image
1987 Majorca Drive, Kissimmee — Na $416,999

INCOME-PRODUCING OPPORTUNITY in Windsor at Westside, one of Kissimmee’s most sought-after short-term rental communities near Orlando’s world-famous theme parks. Unlike ma...

  • 4 Beds
  • 4 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
2015 Majorca Drive, Kissimmee image
2015 Majorca Drive, Kissimmee — Windsor At Westside $412,900

Welcome to your slice of paradise at Windsor at Westside! Fully furnished and Airbnb-ready, this spacious 5-bedroom, 4.5-bath townhome with a private pool is located in o...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
2407 Dubai Street, Kissimmee image
2407 Dubai Street, Kissimmee — 2407 $410,000 ▼

This beautifully furnished 5-bedroom, 4.5-bath townhouse offers an exceptional investment opportunity just minutes from Walt Disney World. Located in the highly desirable...

  • 5 Beds
  • 5 Baths
  • Windsor/Westside-Ph 3 SubDv.
  • 34747 Zip Code
8930 Sydney Avenue, Kissimmee image
8930 Sydney Avenue, Kissimmee — 8930 $409,000

UNIQUE OPPORTUNITY AT WINDSOR AT WESTSIDE | PREMIUM CORNER LOT Step into luxury living with this stunning fully furnished 5 bed/4.5 bath pool home located in the highly s...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
2427 Dubai Street, Kissimmee image
2427 Dubai Street, Kissimmee — 2427 $408,000 ▼

Dive headfirst into paradise at 2427 Dubai Street, Windsor At Westside! Forget ordinary – this is your resort, a dazzling, delivering a 6.9% Cap rate to the current owner...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8944 Sydney Avenue, Kissimmee image
8944 Sydney Avenue, Kissimmee — Pulte Homes $404,900 ▼

Step into this stunning and beautifully furnished 5-bedroom, 4-bathroom townhome nestled within an exclusive resort-style community. Designed with comfort and style in mi...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8867 Geneve Court, Kissimmee image
8867 Geneve Court, Kissimmee $404,000

Welcome to your ideal vacation home and income-producing property in the highly sought-after Windsor at Westside Resort! This beautifully appointed 4-bedroom, 3.5-bathroo...

  • 4 Beds
  • 4 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
2022 Majorca Drive, Kissimmee image
2022 Majorca Drive, Kissimmee — Pulte Homes $399,990

Welcome to 2022 Majorca Drive, a highly desirable 4-bedroom, 3.5-bathroom townhome located in the Windsor at Westside Resort. Positioned in the preferred Phase 1 of the c...

  • 4 Beds
  • 4 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
2410 Tangier Drive, Kissimmee image
2410 Tangier Drive, Kissimmee — N/A $399,900 ▼

MAJOR PRICE IMPROVEMENT — TURNKEY, FULLY FURNISHED 5-BEDROOM POOL HOME IN WINDSOR AT WESTSIDE! Welcome to 2410 Tangier Drive, a beautifully maintained and fully furnis...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 3 SubDv.
  • 34747 Zip Code
8887 Geneve Court, Kissimmee image
8887 Geneve Court, Kissimmee — 8887 $395,000 ▼

Stunning, FULLY FURNISHED home located in the much sought after gated community of Windsor at Westside. This beautiful home is meticulously furnished and beautifully deco...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8899 Geneve Ct, Kissimmee image
8899 Geneve Ct, Kissimmee — 8899 $394,900 ▼

Welcome to Windsor at Westside—one of Central Florida's premier resort communities and one of the most sought-after destinations for vacation homeowners and short-term re...

  • 4 Beds
  • 4 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8891 Geneve Court, Kissimmee image
8891 Geneve Court, Kissimmee — 8891 $390,000

Step into this beautifully furnished 5-bedroom, 4.5-bathroom townhome at Windsor at Westside, one of Kissimmee's popular vacation communities. With 2,263 square feet of l...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
9025 Rhodes Street, Kissimmee image
9025 Rhodes Street, Kissimmee — N/A $390,000 ▼

Priced to Sell! Where else can you live in Florida feeling like you are on Vacation everyday?! Resort style pools, Lazy River, Water Playground, Fitness Center, Restauran...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
1995 Majorca Drive, Kissimmee image
1995 Majorca Drive, Kissimmee — Na $389,000 ▲

Incredible opportunity in the highly sought-after Windsor at Westside Resort! This fully furnished five bedroom, four and a half bathroom retreat comfortably accommodate...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
8859 Geneve Court, Kissimmee image
8859 Geneve Court, Kissimmee — 8859 $388,000

Exceptional Investment Opportunity in Windsor at Westside! Welcome to 8859 Geneve Court, a spacious 5-bedroom, 4.5-bathroom townhome with a private pool, located in th...

  • 5 Beds
  • 5 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code

Windsor at Westside Resort - West Hwy 192

Orlando Vacation Homes › West Hwy 192 Resort Area › Windsor at Westside Resort

Owning a Vacation Home at Windsor at Westside Resort

Windsor at Westside Resort near Disney WorldWindsor at Westside Resort is a gated resort of Single/Multi Family Homes and Townhomes in the West Hwy 192 Resort Area of Orlando. Windsor at Westside is a medium sized townhome and single/multi family resort with BIG amenities.

Owners and guests enjoy a clubhouse packed with amenities including tiki bar and grill, fitness center, arcade, sundry and gift shop, resort pool with splash zone, lazy river and much more. Homes range from 2102 sq ft townhomes to 4391 sq ft 9 bedroom homes with private pools.

Where is Windsor at Westside Resort?

Windsor at Westside Resort is located off Monaco Blvd in the West Hwy 192 resort area near Disney World.

The resort is East of Westside Blvd and South of Hwy 192 and is found in the 34747 zip code in Osceola County.

How Far from Windsor at Westside Resort to...

  • Walt Disney World: 7 miles
  • Universal Studios:20 miles
  • Sea World: 17 miles
  • Busch Gardens Tampa: 62 miles
  • Kennedy Space Center: 70 miles
  • Cocoa Beach: 78 miles
  • Daytona Beach: 82 miles
  • Clearwater Beach: 87 miles
  • Orlando International Airport: 28 miles
  • Port Canaveral Cruise Ships: 72 miles

Windsor at Westside Resort Owner Usage & Property Management

Windsor at Westside Resort ClubhouseWindsor at Westside Resort owners my use their property up to 365 days per year if they so choose. Owners may also rent their unit out for any length of time when not in use to generate income and/or to cover part or all of the owner fees.

There is on site property management at Windsor at Westside Resort. Owners may use 3rd Party rental management or self manage. to handle to reservations and management of their unit at Windsor at Westside Resort.

Windsor at Westside Resort AmenitiesWindsor at Westside Resort Amenities

The 10,000 sq ft clubhouse is the heart of the resort. An on site concierge greets you upon entry and within the clubhouse you have an arcade, state of the art fitness center, sundry shop and kids club. The main pool is more of a miniature water park with a zero entry beach style pool with splash zone on one side and lazy river on the other. The Tu Casa Tiki Bar and Fireplace Lounge offers poolside food and drinks daily and will also have the big game on the TV.

Other amenities include sand volleyball court, tennis court, playground and fishing pier. There is a secondary "quiet" pool overlooking a lake in the newer phase of the resort.

Windsor at Westside Resort Amenities in Orlando near Disney

Windsor at Westside Resort Amenities include:

  • Fishing
  • Fitness Center
  • Playground
  • Park
  • Clubhouse
  • Security
  • Spa/Hot Tub
  • Tennis Courts
  • Basketball Court
  • Waterfront Resort Pool Area with Water-slide
  • Lazy River
  • Restaurant
  • Bar
  • Marketplace
  • Game Room
  • Sand Volleyball Court

Vacation Homes Available in Windsor at Westside Resort

Windsor at Westside Resort Homes for SaleThe majority of the homes in Windsor at Westside Resort were built 2015-2019 by Pulte Homes. There are 3 to 10 bedrooms, a similar number of bathrooms, and between 2500 to 5000 square feet of living space in each of the houses.

All townhomes and homes come with full size kitchens with granite counter-tops in the kitchen and bathrooms, laundry rooms or closets with washer and dryer as well as private, screen pools.

All homes are individually owned, so owners may decorate their home in any style they like. Many of the bedrooms are decorated in a unique theme and most of the garages have been converted to either game rooms or movie theaters.

Windsor at Westside Resort Homes

Typical Windsor at Westside Resort Home Features Include:

  • Architectural Style(s): Florida
  • Number of Bedrooms: 3 to 10
  • Garage Spaces: 2
  • Approx Sq Ft under AC: 2500 to 5000
  • Interior Rooms: Family Room, Great Room, Inside Utility, Loft and Screened Pool
  • Construction Material: Block, Concrete
  • Roof: Tile

Windsor at Westside Resort Video Tour Courtesy of Pulte Homes

Call Us Now at 407-801-3286 and schedule your viewing of vacation homes for sale in Windsor at Westside Resort today!

Photo Credit: Above images by Magical Vacation Homes.

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David Myers - Broker Associate
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Ziro Realty, LLC
549B Water Street
Celebration, FL 34747
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