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

2623 Archfeld Blvd, Kissimmee

New Photo of Listing #O5733175

$420,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.27 Acres

Single Family / Villa

Windsor Hills Ph 06

Stunning 6/4 Pool Home In Windsor Hills! Fabulous Gated Community With Tremendous Amenities! Huge Open Floor Plan With Soaring Ceilings! Neutral Décor Throughout With Tasteful Décor! Separate Formals Great For Entertaining! Gourmet Kitchen With Solid Surface Counter, Wood Cabinets, Ample Counter And Storage Space...all Appliances Stay! Inviting Family Room With Glass Sliders To Sparkling Pool! With 6 Spacious Bedrooms And 4 Baths There Are Plenty Of Opportunities! Home Also Boasts A Generous Size Yard, Charming Curb Appeal And 2-car Ga...

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...

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...

2601 Archfeld Blvd, Kissimmee

Price
Reduced
Photo of Listing #O5550297

$399,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.17 Acres

Single Family / Villa

Windsor Hills Ph 06

Just Reduced For Quick Sale! 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. Yo...

2635 Daulby St, Kissimmee

Price
Reduced
Photo of Listing #O5490124

$399,000

  • 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 ...

2624 Bowring St, Kissimmee

Price
Reduced
Photo of Listing #O5424177

$399,000

  • 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 ...

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...

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...

7809 Basnett Cir, Kissimmee

Photo of Listing #S5006281

$378,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 03

Fully Furnished Luxurious Pool Home In One Of Orlando's Top Gated Vacation Rental Resort Destinations. Featuring Functional Brentwood Floor Plan, This Residence Showcase Prime Location With Spectacular Private Green Views Within Just A Short Commute To Fabulous Club House And Resort Amenities. Fully Equipped Kitchen Is Featuring Ample Counter Top Space And Is Complemented With Upgraded Stainless Steel Appliances (august 2018), Including Brand New Samsung French Door Refrigerator, Electric Range/owen, Microwave, Dishwasher And All Major Kitch...

2633 Pawnall St, Kissimmee

Photo of Listing #O5722639

$375,000

  • 3 Beds
  • 4 Baths

  • 2,966 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 05

This Renovated Custom Redesigned Windsor Hills Family Vacation Home Was Created Specifically With The Perfect Vacation Experience In Mind. Two Bedrooms From The Original Five Were Converted Into A Magnificent Video Arcade And Movie Theatre. The Pool And Spa Face Directly Towards Disney And The Home Has A Fantastic View Of The Nightly Fireworks. Call Today For Your Private Showing. This Is The Special One You Are Looking For....

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 September 18th, 2018 at 11:30am EDT.