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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33 Properties Found. Showing Page 1 of 3
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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...

2515 Archfeld Blvd, Kissimmee

Photo of Listing #O5554570

$420,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.23 Acres

Single Family / Villa

Windsor Hills Ph 07

Immaculate Six Bedrooms, Four-baths On Beautiful And Popular Vacation Resort Community Of Windsor Hills. Located Only Three Miles From The Entrance Of Disney. This Was Truly A Vacation Home For Its Original Owners. House Is Sitting On A Big Corner Lot, Where Your Guests Can Enjoy A Refreshing Pool And Hot Tub. Six Generous Bedrooms, Large Kitchen And An Open Floor Living Space Makes Perfect For Multi-family Vacations Rental Secure With A 24-hour Guard Gate. Clubhouse Includes A Movie Theater, Fitness Center, Game Room With Arcade Games, Ping...

2601 Archfeld Blvd, Kissimmee

Photo of Listing #O5550297

$419,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.17 Acres

Single Family / Villa

Windsor Hills Ph 06

Must See! Stunning 6br/4ba Home With An Open Floor Plan In Highly Sought-after Windsor Hills. Professionally Decorated And Top Of The Line Luxury. 55" Tv In Family Room, Granite Counter Tops, Upgraded Appliances, Dark Wood Cabinetry And A 4-person Breakfast Bar In The Expansive Kitchen. Dining Room Also Seats 8. The 2-car Garage Has Been Converted Into A Game Room With Foosball And Billiard Table. Upstairs Has 1 King Bedroom, 2 Queen Bedrooms, And 3 Bedrooms With Twin Beds. Home Can Easily Accommodate 14 Guests. You Also Have Access ...

2642 Archfeld Blvd, Kissimmee

Featured Photo of Listing #S4857898

$419,500

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills

This Sensational 6 Bedroom 4 Bathroom Property In Windsor Hills Is The Ultimate Orlando Area Vacation Home And Rental Property. Fully Furnished And Decorated To Only The Highest Standards. Tiles Throughout The High Traffic Areas And Featuring An Open Style Floor Plan Ideal For Entertaining And Spending Time With Family And Friends. The Home Has A Combined Living And Dining Space As Well As A Separate Formal Living Area. The Kitchen Is Spacious And Features A Lovely Eating Space Near The Sliding Glass Doors Providing Plenty Of Natural Light. ...

2624 Bowring St, Kissimmee

Price
Reduced
Photo of Listing #O5424177

$400,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.23 Acres

Single Family / Villa

Windsor Hills Ph 06

Price Reduction And Seller Financing Available! 25% Down, 20 Years, 6.5% Interest. This Is One Of The Classiest And Most Beautiful Homes In Windsor Hills. Known As "parkside Palace", The Home Features 6 Very Spacious Bedrooms, An Amazing Family Room And Breakfast Nook, A Formal Dining Room, A Great Living Room And Off Course, A Very Relaxing Pool Deck. The Pool Features A Fantastic Spa And It Is A Salt Water System. All Appliances Are Stainless Steel And Th Kitchen Features Granite Countertops. The Garage Has Been Converted Into A Game Room ...

2709 Manesty Ln, Kissimmee

Photo of Listing #O5573873

$399,999

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.24 Acres

Single Family / Villa

Windsor Hills Ph 03

This Turnkey, Guard Gated Home Is A Must See With No Rear Neighbors. If You Are Looking For A Primary Residence, Vacation/second Home Or Income Producing Property This Home Is For You. This Home Has Everything For You And Your Guests For A Perfect Vacation Or Getaway With 6 Bedrooms 4 Baths Which Include Upgraded Furnishings Throughout And A Home Theater In The Garage Conversion. The Little Ones And Adults Alike Will Love The Disney Themed Bedroom That Sleeps 4-5 Youngsters. The Home Includes A Pool Table, Game Room, Bedroom/bath On 1st Floo...

2551 Archfeld Blvd, Kissimmee

Photo of Listing #O5706057

$399,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.23 Acres

Single Family / Villa

Windsor Hills Ph 07

Corner Homesite And One Of The Largest Pools And Lanai’s In Windsor Hills. This Home Checks All The Boxes And More. A House That Stands Out In The Area's Most Popular Rental Community, Windsor Hills Resort Just 2 Miles From Disney World. Look At This Huge Corner Lot With Exceptional Landscaping And A Large Addition To Rear Of The Pool Area. Its A Unique House That Stands Out From The Rest. Privacy Bushes Surround The Large Pool Deck Which Features Seating For 10 And With 5 Loungers And Still Room To Spare! Highly Desirable 6-bedroom Home In ...

7809 Beechfield St, Kissimmee

Photo of Listing #O5705931

$399,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 05

Location, Location, Location…act Quickly For This Well Maintained, Highly Desirable 6-bedroom Home Located In The 24-hour Guard Gated Luxury Windsor Hills Resort, Location Just 2 Miles To Disney World. This Stunning Home Offers Everything You’re Seeking In A Luxury Vacation Home. Future Bookings In Place Up To The End Of 2019, Rental History, No Rear Neighbors, Privacy, Excellent Quality Turn Key Furniture Package, Game Room In The Garage, Upgraded Tile Roof And Granite Counter Tops. New Resort Water Park Amenity Just Added To The Already Po...

7803 Beechfield St, Kissimmee

Photo of Listing #O5545652

$389,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 05

Windsor Hills Reserve Home For Sale. No Rear Neighbors! Lots Of Future Bookings Are Ready To Convey! This Amazing/ Spotless, 6 Bedroom Home (3 King, 1 Queen And 4 Twin Beds) Can Accommodate 12 Guests In Absolute Comfort, 4 Bathrooms (2 En-suite). There Have Been Over 15 Five Star Reviews On Flipkey Based On Recent Guest Stays Regarding This Beautiful And Luxuriously Furnished Home. Every Bedroom Enjoys A Wall Mounted Flat Screen Lcd Tv With Built In Dvd. Fully Equipped Kitchen And Laundry Room. Large Private Heated Pool With Raised Spa. N...

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...

2635 Daulby St, Kissimmee

Price
Reduced
Photo of Listing #O5490124

$389,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills

This Beautiful 6 Bedroom Vacation Home Is Located Only 3 Miles From Disney And Is Close To All Of The Attractions And Fun Orlando Has To Offer. Located Within Windsor Hills Resort Community, This Home Has Features Like No Other, A Private Newly Remodeled Aruba Twinkling Pool And Spa With Panoramic Views Over Lake Reedy And A Conservation Area, A Whole House Audio System With Ceiling Speakers, Proliphix Home Automation System Controlling The Ac And Pool Heat, New Flat Screen Tvs In All Rooms, A Fully Equipped Gourmet Kitchen With New Samsung ...

2625 Daulby St, Kissimmee

Price
Reduced
Photo of Listing #S4850994

$385,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 02

Spectacular 6 Bedroom Lakefront Pool Home Located On One Of The Best Lots In The Highly Sought After 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 All 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 Every Night.....

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.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on May 25th, 2018 at 10:30am EDT.