Windsor Hills Homes for Sale

Located in the heart of Central Florida’s major tourist attraction area is a beautiful, family-oriented gated vacation resort community known as Windsor Hills. Windsor Hills homes for sale lie in a  meticulously maintained Kissimmee community is located less than 2 miles from Walt Disney World, and offers residents and visitors all the amenities of a 5-star resort! Windsor Hills features a variety of single family / villa homes, townhomes and condos that are perfect for families, couples and retirees who want a vacation getaway with all the comforts of home.

Interested in one of the beautiful Windsor Hills homes for sale available below? Read on to learn more about this stunning Osceola County community, just minutes from Disney World, or contact Team Donovan online to reach a qualified Windsor Hills real estate agent!

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35 Properties Found. Showing Page 1 of 3
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2505 Archfeld Blvd, Kissimmee

Photo of Listing #O5742332

$439,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 07

Fantastic South Facing Vacation Rental Property With High End Furniture, Extended Pool Deck, Heated Pool With New Pump, Tile Roof, New Carpet, Nice Game Room With Newly Added Games And Ac In Garage. Excellent Rental Income History In Safe Guard Gated Community If Windsor Hills. Community Offers Fantastic Water Park With Grocery Store And Game House As Well As Huge Additional Pool Besides Own Private Heated Pool .just 12 Minutes To Disney. Home Is In Very Good Condition.

2603 Daulby St, Kissimmee

Photo of Listing #O5722693

$438,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.17 Acres

Single Family / Villa

Windsor Hills Ph 02

Windsor Hills Is A Premier Gated Community Located Just Miles From The Walt Disney World Resort. Looking For A Vacation Home Or Maybe A Short Term Rental. How About Both? This Beautiful Home Is The Coveted Brentwood, Which Features 6 Bedroom And 4 Full Bathrooms. Ideal For Entertaining And Relaxing During Vacation. You'll Love Lounging By Your Private Screened Patio Pool Overlooking Reedy Lake With Full Water View! You Can Also See The Amenities Like The Big Resort Style Community Pool With Water Slides And Splash Play Area. You Also Have Ac...

2546 Archfeld Blvd, Kissimmee

Photo of Listing #O5737630

$420,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 07

Stunning Home Located In Highly Desirable Community Of Windsor Hills Within Close Proximity To Disney World. Property Is Turn Key And Move In Ready With Beautiful Furniture And Decoration. Community Is Very Desirable And Offers 24 Hours Security, Gated, Large Community Pool Lagoon Style, Movie Theatre Club House, Fitness Center, Game Room And Much More. Home Is Tastefully Decorated With A Very Desirable Floor Plan Highly Desired Among Guests. Home Features 6 Bedrooms, 4 Baths And 2812 Sqft Of Space. Gorgeous Gourmet Kitchen Overlooking The F...

7737 Comrow St, Kissimmee

Photo of Listing #O5705412

$420,000

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 1

Sensational 5 Bedroom, 5 Bathroom Pool Home, Featuring A Custom Kitchen With 42-inch Cognac Color Cabinetry, Stainless Steel Appliances And Granite Counter Top. With 2,494 Square Feet Of Elegant Living Space, This Well-design Floor Plan Features Spacious Bedrooms Suites, Each Bedroom With Their Own Private Bath. The Two-story Floor Plan Will Bring A Blend Of Contemporary Design And Comfort. Professionally Decorated, This Stylish Interior Home Will Amaze You With Every Single Detail. Built On A Premium Lot, No Rear Neighbors, And Located In T...

2556 Archfeld Blvd, Kissimmee

Photo of Listing #O5743236

$416,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 07

This Is The One!!! South Facing Pool, Non Onlooked Immaculate Windsor Hills Home. Granite Counter Tops, Stainless Appliances And Beautifully Decorated For You To Enjoy As A Second Or Vacation Home. Bookings In Place And Can Convey With Current Property Management. The Six Bedroom, Four Bathroom Home Has Upgraded Furnishings Throughout. There Is A Game Room In The Garage, Multiple Gathering Spaces For Guests And Pool With Spa. Schedule Your Viewing Today!

2646 Dinville St, Kissimmee

New Photo of Listing #O5746028

$394,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.23 Acres

Single Family / Villa

Windsor Hills/ventura At...

Brand New Artisan Shingle Roof Just Installed. New Carpet Installed In 2017. One Of The Largest Lots And Longest Drives In Windsor Hills. 100% Owner Bookings Can Convey With Sale! This Spacious, Well Maintained And Updated 6 Bed Is Located In The Area's Most Sought After Rental Community In The Disney Area. Decorated And Equipped To Attract Premium Rentals, This Home Features 3 King Bedrooms (2 Are Ensuites), A Queen And 2 Themed Twin Rooms. The Garage Is A Game Room Conversion With Pool Table, Foosball And Tv And Game Counsel With Seati...

7760 Grassendale St, Kissimmee

Photo of Listing #O5744992

$389,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 06

*matterport Tour Available, Please Click Virtual Tour Link* This Is Is A Wonderful 6 Bedroom / 4 Bathroom Home In The Extremely Popular Windsor Hills Resort. Located Less Than A 2 Minute Drive From The Main Resort Clubhouse Area, This Outstanding Property Home Is Extremely Well Equipped As You Will See. Disney Delight Sleeps 12 Individuals Comfortably, The Bedrooms Consisting Of 2 Masters, Both With King Size Beds And Full En-suite Facilities, 1 Queen Size Bedroom Located On The First Floor, And 3 Other Bedrooms On The Second Floor. The ...

2512 Archfeld Blvd, Kissimmee

Photo of Listing #O5726916

$389,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.18 Acres

Single Family / Villa

Windsor Hills

Luxurious Executive Vacation Home, This 6 Bed/4 Bath Pool Home Offer's Professional Upgraded Furnishings And Decors Throughout, Open Floor Plan, Granite Kitchen Countertops, Upgraded Kitchen Cabinets, Ceramic Tile Flooring In All Living Area's And Bathrooms, Screened Covered Heated Pool & Spa, Brick Paver Covered Lanai, Inside Laundry Room, Game Room In The Garage, And Much More ! Excellent Rental History With Bookings In Place To Transfer. Located In The Most Popular Privacy Gated, Resort Style Community Nearest Disney World! Manned Privacy...

2698 Manesty Ln, Kissimmee

Price
Reduced
Photo of Listing #O5504764

$389,750

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 03

Only 4.5 Miles To Disney’s Gate. This Home Offers One Of The Most Desirable Floor Plans In Windsor Hills With 5 Beds And 5 Baths, This Well- Kept Home Is Located On A Conservation Lot. It Is Walking Distance To Tennis Courts And The Clubhouse. Tastefully Decorated & Furnished With Neutral Colors Throughout And Offered As A Turn Key Property. Boasting 2 Master Suites With King Sized Beds On The First Floor, One Queen Master Suite On The First Floor And Twin Beds On The Second Floor. Fully Stocked Kitchen And Ready To Go Overlooking The Fami...

2704 Manesty Ln, Kissimmee

Photo of Listing #O5741821

$385,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 03

Prepare To Step Into One Of The Most Immaculately-maintained Homes In Windsor Hills When Visiting This Listing! Pride In Ownership Is Evident Throughout The Home, From The Furniture To The Paint, Making It Truly Turn-key For A Vacation Rental Or Permanent Residence. This Luxurious Six Bedroom, Four Bathroom Villa Is Located On The 5 Star Gated Community Of Windsor Hills Resort Which Is Only Minutes Away From The Disney Theme Parks And Local Attraction That Orlando Is Famous For. The Home Has A Private West Facing Pool To Soak Up The Sun, And...

2625 Daulby St, Kissimmee

Photo of Listing #S5005391

$385,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 02

Fantastic 6 Bedroom 4 Bath Lakefront Pool Home Located On One Of The Best Lots In The Highly Sought After Resort Community Of Windsor Hills! You And Your Guests Will Love To Relax By The Sparkling Heated Pool With Its Brick Paver Deck And Inviting Spa By Day And Enjoy The View Of Reedy Lake And The Conservation Area. And When You Want To Get Out Of The Sun For A Bit There's Plenty Of Room On The Huge Covered Lanai To Sit Back And Sip A Cold Drink. When The Sun Sets You Can Go Back Out And You'll Be Treated To The Disney Fireworks Each And Ev...

2616 Daulby St, Kissimmee

Photo of Listing #O5741890

$384,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 02

Brand New Artisan Shingle Roof Just Installed. New Carpet Installed In 2017. 100% Owner Bookings Can Convey With Sale! This Spacious, Well Maintained And Updated 6 Bed Is Located In The Area's Most Sought After Rental Community In The Disney Area. Decorated And Equipped To Attract Premium Rentals, This Home Features 3 King Bedrooms (2 Are Ensuites), A Queen And 2 Themed Twin Rooms. The Garage Is A Game Room Conversion With Pool Table, Foosball And Tv And Game Counsel With Seating. This Home Has Upgraded Cabinets And New Granite In The Kitch...

The Windsor Hills Resort Community

Windsor Hills home owners and their guests can experience all the advantages resort-style living affords, including a luxurious lagoon style heated pool, 80 foot winding water slide, children’s splash area with dancing water fountains and poolside ping pong. Adults can lounge in the sun on the pool deck or relax in the steaming hot tub.

The resort clubhouse also has plenty of entertainment opportunities for young and old alike, including billiard tables, video arcade games and an Xbox Kinect. There’s also an HD movie theater and state-of-the-art fitness center with the latest workout equipment. Other amenities include picnic/BBQ areas, sundry shop, children’s playground, putting green, and tennis, basketball and volleyball courts.

Of course, there are plenty of options for dining, shopping, and first-class entertainment within a short drive of Windsor Hills real estate, including championship golf at the nearby Mystic Dunes Resort & Golf Club.

Windsor Hills Floor Plans

The Windsor Hills homes for sale offers several different floor plans for those interested in purchasing an Orlando vacation home. Buyers who prefer a vacation property that’s easy to maintain often choose a two or three bedroom condo. These beautiful condos feature spacious bedrooms, walk-in closets, appliances, balcony/sundeck and high ceilings. A few condos offer lakefront views, as well as being near the community clubhouse and pool. Some three bedroom condos also include a screened-in patio.

Another option for a vacation home is a three bedroom Windsor Hills townhome. These properties include such features as cathedral/vaulted ceilings, walk-in closets, and all kitchen appliances. Some of the townhomes come fully furnished, and include their own private screened-in swimming pool and/or hot tub for extra privacy.

If you’re looking for a luxurious single family home that can be used as a vacation home or second home, you should consider one of the amazing Windsor Hills villas. Choose between four, five or six bedroom floor plans. These thoughtfully designed homes offer plenty of space for family gatherings, as well as rental guests to enjoy. Some models include a heated pool and spa, with child safety fencing to keep little ones safe.

If you choose to rent your home to vacationers, the Windsor Hills community does allow short and long term rentals, which gives you an opportunity to recoup your investment. Or you can simply keep the property for you, your family and friends to enjoy.

Another benefit of buying a condo or home for sale in Windsor Hills is that this immaculate property is gated with 24-hour security, and features a helpful, friendly staff. As the closest vacation home community to Disney, it will appeal to buyers and renters alike, but the fabulous on-site amenities enable you to enjoy a relaxing vacation without ever leaving Windsor Hills.

If you have any questions about the properties for sale at Windsor Hills, contact a Team Donovan real estate agent online today or call 407-705-2616. We look forward to helping you find the perfect Orlando vacation home.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on November 17th, 2018 at 10:14am EST.