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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64 Properties Found. Showing Page 1 of 6
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7812 Beechfield Street, KISSIMMEE

New Photo of Listing #O5872569

$499,500

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 05

Beautiful 6 Bedroom Home In Windsor Hills Resort. A Gorgeous Resort Just 2 Miles To Disney World That Has Been A Popular Vacation Rental Destination For The Last 15 Years. New Fresh Paint On The Whole Exterior Of The House. Upstair New Carpet All Round.downstair Tile Floor Recently Installed. Brand New A/c Unit Just Installed.this Home Features Upgraded Cabinetry, Tile Roof, Granite Counter Tops And Stainless Steel Appliances. Screened In Pool And Spa With Shaded Lanai With Brick Paved Patio. Sparkling Pool Is South Facing And Receives Maxi...

2625 Daulby Street, KISSIMMEE

New Photo of Listing #S5034216

$479,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 02

Very Close To Disney Entrance, Approximately 2 Miles Away Or 10 Min Away, This State-of-the-art Disney-themed 6 Bedroom 4 Bath Lakefront Pool Home Located On One Of The Best Lots In The Highly-sought After Resort Community Of Windsor Hills! The House Is Modelled After Disney Movies Immersing Families Into The Disney Magical Experience. Rooms Are Beautifully Appointed With New Furniture Galore And 2 New Acs. Relax By The Sparkling Heated Pool With Brick Paver Deck And Inviting Spa By Day And Enjoy The View Of Reedy Lake And The Conservation A...

7733 Teascone Boulevard, KISSIMMEE

New Photo of Listing #S5035944

$450,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills

An Investors Dream! This Beautiful Turnkey 5 Bedroom 5 Bathroom Home With A Converted Garage And Two Complete Themed Bedrooms, Comes With Bookings! Walking Distance To The New Water Park And Clubhouse! Only A Few Steps Away From The Playground Area! Already Managed By The Top Producing Company For Vacation Rentals, High End Rental Rates And Has Future Bookings!

2692 Manesty Lane, KISSIMMEE

New Photo of Listing #S5037763

$440,000

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills

Huge Price Improvement: Attention Investors! You Now Have The Opportunity To Own One Of The Top Producing Homes In Windsor Hills. This 5 Bed 5 Bath Home Is Designed For Performance From Top To Bottom. Gorgeous Furnishings. En Suite Bathrooms. Themed Bedrooms. Fully Converted Air Conditioned Garage With Arcade Games And Projection Tv! Your Guests Will Enjoy The Beautiful Florida Sun With This West Facing Pool And Hot Tub. Already Managed By The Top Producing Company For Vacation Rentals, High End Rental Rates And Has Future Bookings! Did I Me...

2589 Archfeld Boulevard, KISSIMMEE

New Photo of Listing #O5880757

$427,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 7

Attention!! Beautiful 6br/4ba Home Is Now For Sale. Located Only Minutes From The Main Orlando Attractions, This Home Is A Perfect Escape From The Routine Of Daily Life. Home Is Located In State-of-the-art Vacation Community Of Windsor Hills Resort And Is A Piece Of Paradise That You, Yes, You Can Now Own. Six Gorgeous And Modern-designed Bedrooms Are Ready To Accommodate Any Family. The Princess And Spider-man Themed Bedrooms Will Be A Huge Hit With Families. There Is Also A 42-in. Flat Screen Tv, Ideal For Family Movie Time. The Poo...

7751 Tosteth Street, KISSIMMEE

New
& Featured
Photo of Listing #S5040298

$419,950

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.20 Acres

Single Family Residence

Windsor Hills

Wonderful 6 Bedroom 4 Bath Home In The Gated Windsor Hills Resort. This Home Provides A Large Corner Lot For The Enjoyment Of Your Pool, Spa, Covered Seating Area With Plenty Of Furniture And Outdoor Lawn Activities. An Open And Spacious Floor Plan For The Living Room, Kitchen, Dining Room And Family Room Provides Plenty Of Space For Entertaining. This Fully Furnished Home Features One Bedroom Downstairs With All Remaining Themed Bedrooms, Including The Master Bedroom With An Ensuite Bathroom Featuring Dual Sinks, Tub And Separate Shower A...

7768 Tosteth Street, KISSIMMEE

New
& Featured
Photo of Listing #S5038340

$419,950

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills

Newly Renovated Impressive 6 Bedroom 4 Bath Home In The Gated Windsor Hills Resort. This Two-story Fully Furnished Home Features One Bedroom Downstairs, An Open And Spacious Floor Plan For The Living Room, Kitchen, Dining Room And Family Room. The Kitchen Area Provides Plenty Of Seating For Everyone For Entertaining. All Remaining Themed Bedrooms, Including The Master Bedroom With An Ensuite Bathroom Featuring Dual Sinks, Tub And Separate Shower Are Upstairs. Step Out Onto Your Covered Porch And Enjoy Your Heated Sparkling Pool And Spa. This...

7753 Hockendale Street, KISSIMMEE

New Photo of Listing #S5031358

$417,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 06

This Beautiful Fully Furnished 6 Bedroom, 4 Bath Home With Heated Pool/spa Is Located In A Gated Resort Community Windsor Hills It Can Fit Your Whole Family Or Be Used As Short Term Rental! Tiled Entry Leads Into Living Room As Well As Access To Stairway. Kitchen Has Pass Through To Dining Room And Offers Breakfast Bar And Dinette Area With Sliding Glass Doors. Master Bed Room Offers Walk-in Closet, Private Bath With Dual Sinks, Garden Tub And Separate Shower. Covered Patio Overlooks In-ground Screened Pool. Community Club House Comes With ...

7785 Basnett Circle, KISSIMMEE

New Photo of Listing #S5013210

$409,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 03

Spacious 6 Bedroom With 2 Master Suites And 4 Full Bathrooms! **furnished!** New Roof!** Lovely Vacation Home In Windsor Hills Close To Disney And Major Theme Parks. Think About It You Can Live In The Home Full Time Or Rent Out To Vacationers. Folks Love Windsor Hills For The Location! The Community Is Guard Gated And Has Amenities Such As A Lagoon Style Pool With Hot Tub, Club House, Large Water Slides, Game Room, Movie Theater, Café, Fitness Center, Bar And Convenient Store, Tennis Courts, Volleyball Courts, Huge Playground, Putting Green ...

7737 Teascone Boulevard, KISSIMMEE

New Photo of Listing #S5034276

$409,000

  • 4 Beds
  • 4 Baths

  • 1,878 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 05

Near Disney, Just Under 2 Miles From The Exit, This Beautiful Home Is As Close As You Can Get To Brand New! Everything About This House Is Super New And Unused. To Start With, This Gorgeous 4 Bedrooms/4 Bath Home Is Located In The Gated Community Of Windsor Hills And Exudes The Disney Experience As The Rooms Have Disney Theme. From Top To Bottom, Everything Has Been Replaced In March 2020 With Brand New Roof, New Porcelain Tile Floor Throughout, New Interior And Exterior Paint, New Kitchen Including New Granite Countertops And New Backsplash...

7753 Grassendale Street, KISSIMMEE

New Photo of Listing #O5841926

$408,775

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 06

Come See This Well Kept 5 Bed 5 Bath Pool Villa That's Only Minutes Away From Disney. This Home Has 2 Master Suites With Walk In Closets Located On The First Floor Overlooking The Pool And Spa Area. This Lovely Windsor Hill Villa Is A Fantastic Short Term Rental Home That Also Includes A Games Room, Granite Counter Tops And Stainless Steel Appliances In The Kitchen And A South Facing Pool. The Community Has An Amazing Array Of Amenities On Offer For Everyone, Water Park, Tennis Courts, Fitness Center, Movie Theatre And Much More! This Beauti...

2621 Archfeld Boulevard, KISSIMMEE

New Photo of Listing #O5870736

$399,999

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.21 Acres

Single Family Residence

Windsor Hills Ph 06

Welcome To This Stunning Rental Home Located In The Resort Community Of Windsor Hills. This Beautifully Decorated Home Is Perfect For A Weekend Getaway Or Long Stay Here In Central Florida. To Begin, This Spectacular Open Floor Plan Home Features 5 Spacious Bedrooms With Plenty Of Space For You And Your Guests. The Bedroom Configurations Consist Of Two King Bedrooms, One Queen Bedroom, One Full Bedroom And One Bedroom Featuring Two Twin Beds. In Total, This Large House Can Sleep Up To 10 Guests. The Wonderful Home Also Features A Kitchen Tha...

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 DBA Stellar MLS.

Listing information last updated on October 28th, 2020 at 12:20pm EDT.