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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17 Properties Found. Showing Page 1 of 2
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7812 Beechfield Street, KISSIMMEE

New Photo of Listing #O5975508

$689,000

  • 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. Upstairs New Carpet All Round. Downstairs 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 M...

2626 Dinville Street, KISSIMMEE

New Photo of Listing #O5955407

$679,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 3

Mint Condition, Fully Furnished, 6 Bedrooms With 2 Master Suites And 4 Bathrooms, Luxury Pool Home Only 3 Miles From Disney. This Amazing Home Is Located In The Highly Sought-after Windsor Hills Resort And Is Your Ideal Home, Vacation Getaway, Or Short-term Rental. This Home Has It All Including South-facing Pool, Oversized Pool Deck Under A Huge Covered Lanai, Open Kitchen, Game Room, Spa, Etc. This Home Is Perfect For Making Memories That Will Last A Lifetime! This Stunning Vacation Home Is Being Sold Fully Furnished Including Many Rece...

2579 Archfeld Boulevard, KISSIMMEE

New Photo of Listing #G5045788

$650,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.17 Acres

Single Family Residence

Windsor Hills Ph 07

Location, Location, Location !! This 6 Bedroom 4 Bathroom Pool & Spa Home Is Somewhere You Can Relax And Unwind From Busy Days Out At The Parks Or Shopping Sprees At The Outlets. Take A Swim In The South East Facing Pool, Spend Some Time In The Spa Or Enjoy Lovely Conversation Under The Private Lanai. The Kitchen Is Welcoming, Allowing The Entire Family To Gather For Delicious Home Cooked Meals. Stainless Steel Appliances. The Game Room Is Supplied With A Pool Table And Air Hockey Table So Everyone Can Join In On The Fun! There Are 5 Bedr...

2634 Dinville Street, KISSIMMEE

New Photo of Listing #O5965488

$650,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.24 Acres

Single Family Residence

Windsor Hills Ph 03

Absolutely Stunning, Turn Key, 5 Bed, 5 Bath Home In The Premier Vacation/holiday Rental Community Of Windsor Hills Resort, Located Within 2 Miles Of The Walt Disney Resort. Upon Entering This Beautifully Maintaining Home, The Open Floor Plan Will Allow You To View The Refreshing Pool & Hot Tub Through The Very Welcoming Entry, Dining Room And Living Room. To Your Right, You Will See The Wide Open, Dine-in, Kitchen. The First Floor Also Includes 2 Master Bedrooms, A Third Bedroom With Adjacent Bathroom And Large Arcade With A Pool Table, ...

2581 Archfeld Boulevard, KISSIMMEE

New Photo of Listing #O5957953

$649,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 07

4.5 Miles To Disney’s Doorstep, This Is As Close As You Can Get Without Being On The Property. Open To View On 7/15/2021 From 11 Am Till 2pm. Guest Checking Out And New One Checking In. Windsor Hills Is An Upscale – 24-hour Guard Gated Community With Impeccable Landscaping Maintained By The Hoa. This Home Has A South-facing Saltwater Pool And Spa Completed In June Of 2021. It Comes Furnished As A Turn-key Home Ready To Go As An Investment Or Simply Move In. My Sellers Have One Of The Top Managers In Place To Assist You With Bookings And Mai...

2640 Dinville St, KISSIMMEE

New Photo of Listing #O5965120

$639,900

  • 6 Beds
  • 3 Baths
  • 1 Half

  • 2,469 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 03

Your Florida Home Awaits!!! This Turn Key Vacation Home Has 6 Bedrooms And 3 1/2 Baths And Is Located In The Popular Resort Community Of Windsor Hills. On The First Floor In This Wonderful Home You Will Find 3 Bedrooms And 2 1/2 Baths Including The Master Suite And Living Room Which Both Have Access To The Covered Lanai And Pool With Spa. There Is Also The Convenience Of A Half Pool Bath Off Of The Kitchen/dining Room. The Master Bath Features Double Sinks A Soaker Tub And Walk In Shower. Upstairs You Will Find 3 More Well Appointed Bedrooms...

2715 Manesty Lane, KISSIMMEE

New Photo of Listing #T3329726

$622,715

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.27 Acres

Single Family Residence

Windsor Hills Ph 05a

Rare Find...high Grossing Rental Opportunity In Windsor Hills! This Spectacular ‘one Of A Kind’ Income Producing Vacation Home Is Situated On One Of The Largest Lots In Highly Sought After Windsor Hills Resort, Just Less Than 3 Miles To Disney World. There Is A Beautiful Open Aspect To The Rear With No Rear Neighbor And Only One Side Single Story Neighbor, Offering Complete Privacy For You And Your Guests. This Private Location Has Been A Major Reason For Its Excellent Rental History For 11+ Years Averaging Over 300+ Days Per Annum. This Mov...

2649 Dinville Street, KISSIMMEE

New Photo of Listing #O5966409

$609,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.13 Acres

Single Family Residence

Windsor Hills Ph 03

Price Reduced: Matterport Tour Available At Https://my.matterport.com/show/?m=ef91tvgx1q3&mls=1. Welcome Home To This Wonderful Family Retreat In Windsor Hills. Boasting 6 Bedrooms And 4 Bathrooms, This Property Is Full Of Upgrades And Tlc Complimentary Of Its Loving Owners. Younger Guests Will Enjoy The Themed Bedrooms And The Grown Ups In Us All Will No Doubt Relax On The Pool/spa Deck, Or In Any Of The Massively Upgraded Living Areas. The Property Is Turnkey And Ready To Be Your Second Home Or A Vacation Rental In A Community Which Is Wel...

7759 Basnett Circle, KISSIMMEE

New Photo of Listing #S5054697

$595,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.19 Acres

Single Family Residence

Windsor Hills Ph 03

Space 6/bed 4/bath,. Fully Furnished And Tastefully Decorated.one Brand New Air Conditioner, Newer Appliance, New Pool Heater....great Condition, 2 Miles To Disney, Amazing Resort Amenities … Great For Residence, Vacation Home Or Short Rental, Currently It Is Used As Short Rental Property, Which Have A Good Rental Record, Thousands Future Booking Can Transfer To Buyer For Free.

7783 Basnett Circle, KISSIMMEE

New Photo of Listing #O5972724

$590,000

  • 6 Beds
  • 3 Baths
  • 1 Half

  • 2,469 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 3

Fantastic Fully Furnished Turn Key Home In The Highly Sought After, Gated, Resort Community Of Windsor Hills! Don't Miss Out On This Rare Opportunity To Own A Fantastic Primary Residence, Investment, Or Vacation Home. This Beautiful 6 Bedroom, 3.5 Bathroom Features A Downstairs Master Bedroom, 2 Additional Downstairs Bedrooms, A Game Room In The Garage, And Beautiful Heated Pool And Spa With No Rear Neighbors. Windsor Hills Is Kissimmee's Premier Resort Community, Featuring A 24 Hour Manned Gate, A Resort Style Swimming Pool, Water Slides...

2520 Archfeld Boulevard, KISSIMMEE

New Photo of Listing #G5044516

$590,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.22 Acres

Single Family Residence

Windsor Hills Ph 07

Location, Location, Location!! Ever Popular Windsor Hills Gated Community, This 2800 Sq Ft 6 Bedroom 4 Bathroom Pool/spa Home Is Offered Furnished. As You Enter The Home You Have The Formal Living And Dining Area With An Open Arch Looking Into The Kitchen And Pool Area. Downstairs The High Ceilings And Open Floor Plan Make This Home Feel Bright And Spacious, The Kitchen Comes With Granite Counter Tops, Stainless Steel Appliances. There Is Eating Space In The Kitchen At The Breakfast Bar And A Large Table In The Nook Area Also Which Leads O...

2634 Daulby Street, KISSIMMEE

New Photo of Listing #S5053551

$579,990

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.30 Acres

Single Family Residence

Windsor Hills Ph 02

Stunning 6-bedroom Windsor Hills Resort Vacation Home With 2 Suites, 3 Themed Custom Designed Bedrooms, Game Room And Luxury Screened Private Pool (southwest Facing) & Spa With Safety Fence, Furnished Patio With Extra Large Lanai, Fine Furniture Throughout The House, Ceiling Fan In Every Room, Central Air Conditioning, Fully Equipped Eat-in Kitchen, Laundry Area With Washer And Dryer, Iron And Board, Baby Crib, Playpen, Highchair And Strollers, Tv/dvd Combo In Living Room And Every Bedroom...other Special Features Are: Extra Large Pool Deck ...

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 September 27th, 2021 at 5:19am EDT.