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Windsor Hills Resort Vacation Homes for Sale

2530 Holtrock Street, Kissimmee image
2530 Holtrock Street, Kissimmee $734,900 ▼

Rare opportunity for a large corner lot that's just over a 1/4 acre!! Fully furnished turnkey 6 bed 4 bath Smart Home in the highly sought after, gated resort community o...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 7 SubDv.
  • 34747 Zip Code
2648 Daulby Street, Kissimmee image
2648 Daulby Street, Kissimmee $728,888 ▼

LOCATION, LOCATION, LOCATION!! ALL offers welcome. Ever popular Windsor Hills gated community, this is a 6 bedroom 3.5 bathroom with a WEST FACING pool/spa and lanai. The...

  • 6 Beds
  • 3.5 Baths
  • Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
7773 Basnett Circle, Kissimmee image
7773 Basnett Circle, Kissimmee $725,000

Presenting the Exquisite Windsor Estate, a symbol of unrivaled luxury and refined living. This breathtaking 6-bedroom, 4-bathroom property epitomizes opulence at its fine...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 03 SubDv.
  • 34747 Zip Code
2623 Pawnall Street, Kissimmee image
2623 Pawnall Street, Kissimmee $724,900 ▼

Absolutely stunning 6 bedrooms and 4 baths pool/jacuzzi home. This one owner property was never rented and comes fully furnished. This hidden gem is nestled in front of...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 06 SubDv.
  • 34747 Zip Code
2671 Manesty Lane, Kissimmee image
2671 Manesty Lane, Kissimmee $720,000 ▼

Welcome to 2671 Manesty Ln, an extraordinary fully furnished home located in the highly sought-after Windsor Hills community of Kissimmee, Florida. Offering immense poten...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 03 SubDv.
  • 34747 Zip Code
7751 Basnett Circle, Kissimmee image
7751 Basnett Circle, Kissimmee $717,770 ▼

GORGEOUS FULLY FURNISHED AND TURN-KEY SCREENED POOL & SPA HOME IN AWESOME LOCATION!!! JUST 1.4 MILES FROM WALMART SUPER-CENTER OLD LAKE WILSON, 10 MINUTES DRIVE TO WALT D...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 03 SubDv.
  • 34747 Zip Code
2692 Manesty Lane, Kissimmee image
2692 Manesty Lane, Kissimmee $713,999 ▼

Attention investors! You now have the opportunity to own one of the top producing homes in Windsor Hills. Already managed by a top producing company for vacation rentals,...

  • 5 Beds
  • 5 Baths
  • Windsor Hills Ph 03 SubDv.
  • 34747 Zip Code
2683 Manesty Lane, Kissimmee image
2683 Manesty Lane, Kissimmee $699,000

Welcome to this beautiful Turn-Key vacation home in Kissimmee. This 5/5 vacation home is located in the gated community of Windsor Hills Resort. This property offers an i...

  • 5 Beds
  • 5 Baths
  • Windsor Hills Ph 3 SubDv.
  • 34747 Zip Code
7755 Hockendale Street, Kissimmee image
7755 Hockendale Street, Kissimmee $699,000 ▼

*** YOU JUST HAVE TO LOOK AT THIS GREAT DEAL *** Welcome to Windsor Hills Resort; within this 24 x 7 manned gated resort where you’ll find this home which offers the perf...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 06 SubDv.
  • 34747 Zip Code
7759 Basnett Circle, Kissimmee image
7759 Basnett Circle, Kissimmee $695,000

Dream vacation Home! Space 6/bed 4/bath, Fully furnished and tastefully decorated. new roof 2021, one new air conditioner 2021,2 master suites, private pool/spa...2 miles...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 03 SubDv.
  • 34747 Zip Code
7812 Beechfield Street, Kissimmee image
7812 Beechfield Street, Kissimmee $685,000 ▼

JUST REDUCED!!!! Are you looking for a vacation rental close to the attractions that you can use when you want, and earn income on when you are not using it? Look no fur...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 05 SubDv.
  • 34747 Zip Code
2693 Manesty Lane, Kissimmee image
2693 Manesty Lane, Kissimmee $679,000 ▼

Price to Sale!!! Can you image: Sitting in the private Spa drinking a beer with friends, or enjoying Disney fireworks at second floor with your kids? This is your dream...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 03 SubDv.
  • 34747 Zip Code
2620 Dinville Street, Kissimmee image
2620 Dinville Street, Kissimmee $630,000 ▼

Excellent value on this FULLY FURNISHED 5 BR/5 BA holiday home in the desirable Windsor Hills, a gated resort community. Over $50,000 invested in quality updates, includi...

  • 5 Beds
  • 5 Baths
  • Windsor Hills Ph 03 SubDv.
  • 34747 Zip Code
7735 Comrow Street, Kissimmee image
7735 Comrow Street, Kissimmee $575,000

Are you looking for a vacation rental close to the attractions that you can use when you want, and earn income on when you are not using it? Look no further, the place fo...

  • 4 Beds
  • 4 Baths
  • Windsor Hills SubDv.
  • 34747 Zip Code
2547 Renshaw Street, Kissimmee image
2547 Renshaw Street, Kissimmee — 2547 $485,000

The turnkey investment you have been waiting for! Fully furnished 3 bed, 3 bath townhome located in the highly sought after community of Windsor Hills, located only a few...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
2575 Maneshaw Lane, Kissimmee image
2575 Maneshaw Lane, Kissimmee — 2575 $470,000 ▼

Absolutely beautiful completely remodeled 3 bedroom/3 bathroom townhouse located in the highly desired Windsor Hills! Fully furnished, new appliances, granite countertops...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 04 SubDv.
  • 34747 Zip Code
7682 Fitzclarence Street, Kissimmee image
7682 Fitzclarence Street, Kissimmee — 7682 $465,000

Welcome to this fully furnished 3 bedroom end unit townhome located in Windsor Hills with future bookings in place. This light and bright home boasts high ceilings and a ...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
2562 Renshaw Street, Kissimmee image
2562 Renshaw Street, Kissimmee — N/A $465,000

The townhome is a furnished 3 bedroom 3 FULL bathrooms, ideally located across from the clubhouse. Brand new A/C and Water heater means the two main interior expenses ar...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
7692 Sir Kaufmann Court, Kissimmee image
7692 Sir Kaufmann Court, Kissimmee — Na $460,000

Welcome to the secure, guard-gated community of Windsor Hills. This property serves as a versatile option, suitable for use as a primary residence or as a lucrative short...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
7660 Otterspool St, Kissimmee image
7660 Otterspool St, Kissimmee — 7660 $459,000

Introducing an impeccable investment opportunity, this exquisite 3-bedroom | 3-bathroom townhouse, featuring a private pool and a bathroom for each bedroom. With its exce...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 2 SubDv.
  • 34747 Zip Code
2503 Maneshaw Lane, Kissimmee image
2503 Maneshaw Lane, Kissimmee — Windsor Hills $450,000 ▼

This beautiful updated and fully renovated property offers a convenient and comfortable lifestyle, with its spacious layout and desirable features. With three bedrooms...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 04 SubDv.
  • 34747 Zip Code
2572 Maneshaw Lane, Kissimmee image
2572 Maneshaw Lane, Kissimmee — 2572 $435,000 ▼

This is a truly turnkey vacation townhouse – fully renovated and fully furnished. It is move-in ready. All bedrooms/bathrooms are en suite. The master bedroom has a kin...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 04 SubDv.
  • 34747 Zip Code
7669 Otterspool Street, Kissimmee image
7669 Otterspool Street, Kissimmee — 7669 $430,000 ▼

Welcome to this beautiful vacation home in Kissimmee, Florida! This luxurious fully furnished townhome has 3 bedrooms and 3 bathrooms, providing a comfortable and conven...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
7654 Otterspool Street, Kissimmee image
7654 Otterspool Street, Kissimmee — 7654 $430,000 ▼

PRICE IMPROVEMENT! The investment property you have been waiting for! Fully furnished 3 bed, 3 bath townhome located in the highly sought after community of Windsor Hills...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
7662 Otterspool Street, Kissimmee image
7662 Otterspool Street, Kissimmee — 7662 $430,000 ▼

This incredible renovated and totally furnished townhouse is move-in ready and totally set up for a successful short term rental program. It has great amenities to attra...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
7660 Comrow Street Unit 104, Kissimmee image
7660 Comrow Street Unit 104, Kissimmee — 7660 $375,000

SHORT WALK TO WINDSOR HILLS CLUBHOUSE, POOL, & WATERPARK! Ground Level!! This amazing 3 bedroom 2 bathroom ground-level condo is sold fully furnished and zoned for short-...

  • 3 Beds
  • 2 Baths
  • Ventura Windsor Hls P7 SubDv.
  • 34747 Zip Code
7671 Comrow Street Unit 103, Kissimmee image
7671 Comrow Street Unit 103, Kissimmee — 103 $360,000

Tastefully decorated and turnkey, this 3/2 condo is located in the ever-popular Windsor Hills resort community and comes fully furnished with management and bookings in p...

  • 3 Beds
  • 2 Baths
  • Windsor Hills, The Ventura At Windsor Hills SubDv.
  • 34747 Zip Code
2788 Almaton Loop Unit 101, Kissimmee image
2788 Almaton Loop Unit 101, Kissimmee — 2788 $349,000 ▼

Ground Level! This amazing 3 bedroom 2 bathroom ground-level condo is sold fully furnished and zoned for short-term rental. Schedule a showing today! This condo is truly...

  • 3 Beds
  • 2 Baths
  • Ventura Windsor Hills P1 SubDv.
  • 34747 Zip Code
2821 Almaton Loop Unit 403, Kissimmee image
2821 Almaton Loop Unit 403, Kissimmee — 2821 $346,000

Discover this exquisite fourth-floor end unit condominium boasting 3 bedrooms and 2 bathrooms, nestled within the secure confines of the guard-gated Windsor Hills Resort ...

  • 3 Beds
  • 2 Baths
  • Windsor Hills Resort SubDv.
  • 34747 Zip Code
2785 Almaton Loop Unit 203, Kissimmee image
2785 Almaton Loop Unit 203, Kissimmee — 2785 $310,000 ▼

Priced to SELL! This amazing 3 bedroom 2 bathroom second floor condo is sold fully furnished and zoned for short-term rental. Schedule a showing today! This condo is trul...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
2778 Almaton Loop Unit 102, Kissimmee image
2778 Almaton Loop Unit 102, Kissimmee — 2778 Almaton $299,900

Welcome to Paradise! Located just minutes from Walt Disney World and Margaritaville, this popular Ground Floor 2 Bedroom Condo inside the desirable resort community of Wi...

  • 2 Beds
  • 2 Baths
  • Ventura At Windsor Hills Ph 03 SubDv.
  • 34747 Zip Code
2774 Almaton Loop Unit 202, Kissimmee image
2774 Almaton Loop Unit 202, Kissimmee — 2774 $298,000

Feast your eyes on this THEMED 2 bedroom 2 bathroom fully furnished condo in the popular short-term rental community of Windsor Hills Resort. Tastefully decorated, them...

  • 2 Beds
  • 2 Baths
  • Ventura At Windsor Hills Ph 03 SubDv.
  • 34747 Zip Code

Windsor Hills Resort - West Hwy 192

Orlando Vacation Homes › West Hwy 192 Resort Area › Windsor Hills Resort

Owning a Vacation Home at Windsor Hills Resort

Windsor Hills Resort near Disney WorldWindsor Hills Resort is a gated resort of Single/Multi Family Homes and Townhomes in the West Hwy 192 Resort Area of Orlando. Windsor Hills is an older but still extremely popular resort loaded with amenities, home style options and in a fantastic location near Disney.

Whether it is the 80 foot water slide or the arcade loaded with modern and classic games, every guest is sure to find an amusement to entertain them at Windsor Hills.

Located just off Hwy, 192, Walt Disney World is just a couple of miles away, and you have plenty of dining, shopping and entertainment options in any direction you go from the resort.

Where is Windsor Hills Resort?

Windsor Hills Resort is located off N Old Lake Wilson Road in the West Hwy 192 resort area near Disney World.

The resort is South of Hwy 192 and East of the 429 Expressway and is found in the 34747 zip code in Osceola County.

How Far from Windsor Hills Resort to...

  • Walt Disney World: 3 miles
  • Universal Studios:16 miles
  • Sea World: 12 miles
  • Busch Gardens Tampa: 63 miles
  • Kennedy Space Center: 66 miles
  • Cocoa Beach: 74 miles
  • Daytona Beach: 78 miles
  • Clearwater Beach: 88 miles
  • Orlando International Airport: 24 miles
  • Port Canaveral Cruise Ships: 68 miles

Windsor Hills Resort Owner Usage & Property Management

Windsor Hills Resort ClubhouseWindsor Hills 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 Hills Resort. Owners may use 3rd Party rental management or self manage. to handle to reservations and management of their unit at Windsor Hills Resort.

Windsor Hills Resort AmenitiesWindsor Hills Resort Amenities

The resort clubhouse features a movie theater, state of the art gym, huge game room with billiards and video games, sundries shop and tiki bar & grill. The clubhouse pool area features a large, palm tree shaded, beach entry pool, separate splash zone area with two water slides. There is also a hot tub and arbors and umbrellas for shading.

In a separate area of the resort there is a sportsplex area with sand volleyball court, tennis courts, basketball court and golf putting green.

Windsor Hills Resort Amenities in Orlando near Disney

Windsor Hills Resort Amenities include:

  • Resort Clubhouse Area with Fitness Center
  • Game Room
  • Movie Theater
  • Restaurant
  • Bar
  • Waterpark Pool Area with Slides
  • Spa/Hot Tubs
  • Tennis
  • Basketball
  • Sand Volleyball Courts

Vacation Homes Available in Windsor Hills Resort

Windsor Hills Resort Homes for SaleThe majority of the homes in Windsor Hills Resort were built 2005-2008 by Pulte Homes. There are 3 to 6 bedrooms, a similar number of bathrooms, and between 1246 to 2800 square feet of living space in each of the houses.

Vacation home options at Windsor Hills include 2 or 3 bedroom condos, 3 bedroom townhomes or 4 to 6 bedroom villa homes.

The townhomes and condos feature full kitchens and family room/dining room combos as well a laundry closed with washer and dryer.

The homes offer the same options as the townhomes and condos but with more space. Many of the homes come with private swimming pools. Owners may decorate their properties any way they see fit. There is no restriction on interior decor.

Windsor Hills Resort Homes

Typical Windsor Hills Resort Home Features Include:

  • Architectural Style(s): Spanish/Mediterranean, Contemporary and Florida
  • Number of Bedrooms: 3 to 6
  • Garage Spaces: 0 to 2
  • Approx Sq Ft under AC: 1246 to 2800
  • Interior Rooms: Family Room, Inside Utility
  • Construction Material: Block, Brick, Stucco and Wood Frame
  • Roof: Shingle and Tile

Windsor Hills Resort Video Tour Courtesy of Global Vacation Rentals

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

Photo Credit: Above images by Reunion Vacation Homes.

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Realtor David MyersDavid Myers 407-801-3286
Your Orlando Vacation Home Expert

Orlando Vacation Properties Buyers Guide

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David Myers - Broker Associate
MyOrlandoVacationHome.com Team
Ziro Realty, LLC
619 Celebration Ave 
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407-801-3286

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