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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13 Properties Found. Showing Page 1 of 2
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7765 Teascone Boulevard, KISSIMMEE

New Photo of Listing #O6068508

$735,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 06

Welcome To Your New Home Away From Home And This Ideal **vacation Spot Or Short Term Rental** In The Sought-after Windsor Hills Community Convenient To All Central Florida Attractions! This 6bd/4ba Fully Furnished **pool Home** Has All The Space You Need For Friends And Family Including A Main Floor Bed & Bath, Two En-suites And The Garage Has Been Converted Into A Fun Game Room! Your First Floor Is Bright And Open With Formal Living And Dining Spaces In Addition To The Casual Dining And Family Room Open To The Kitchen And Pool Area. The Sun...

2538 Archfeld Boulevard, KISSIMMEE

New Photo of Listing #O6043685

$699,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family Residence

Windsor Hills Ph 07

Spectacular Pool Home With Spa Located In The Guard-gated, Resort-style Community Of Windsor Hills. This Two-story, Single-family Home Comes Fully Furnished With 6 Bedrooms And 4 Bathrooms. The Home Includes 2 Master Bedrooms, A Formal Living/dining Room, Kitchen, Nook, And Family Room Overlooking The Pool Area. The Garage Has Been Converted Into A Themed Game Room With Air Hockey And Pool Table For You And Your Guests To Enjoy. This Home Is Turn-key If You Choose To Rent It Out. Windsor Hills Is An Excellent Resort With World-class Ameniti...

7754 Tosteth Street, KISSIMMEE

New Photo of Listing #P4923552

$649,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 03

Welcome To Year Round Sunshine And Endless Florida Vacation Adventures. This Vacation Home Offers Plenty Of Space For Entertainment For One Or Multiple Families And Conveniently Located Twelve Minutes To The Disney Area. A Comfortable Open Concept Floor Plan And Large Parking Area With Attached Two Car Garage Currently Used As A Converted Game Room. The Kitchen Is Equipped With Newly Painted Wood Cabinets, Granite Countertops And A Kitchen Bar Top Counter Giving Plenty Of Room To Move Around The Kitchen Area And Eat Comfortably. Gatherings A...

7822 Beechfield Street, KISSIMMEE

New Photo of Listing #S5064471

$579,995

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 5

Nice Tiled Roof Home With South Facing Private Pool In The Prestiage 24/7 Man Guarded Community Windsor Hills! This Fully Furnished Home Is 2,382 Sq. Ft And Features Five Bedrooms And Five Baths With An Open Dining Area, Spacious Living Room, And Cozy Breakfast Nook, Master Bedroom Is Located On The First Floor Plus Two Extra Bedrooms, Two Additional Bedrooms On The Second Floor. The Attached 2-car Garage Has Been Converted Into A Game Room. Beautiful Landscaping Surrounds The Home, And A Scenic Park Sits Directly Across The Street. Windsor ...

7661 Fitzclarence Street, KISSIMMEE

New Photo of Listing #O6035129

$479,900

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills

This Fully-furnished, Well Maintained Townhome Offers 3 Bedroom En-suites Spread Over A Spacious 1440 Square Feet. It Is A Perfect Layout With One Bedroom Suite On The First Floor, And The Two Other Bedroom En-suite's Upstairs Providing Maximum Privacy. The Open Living Room, Dining Area, And Kitchen Combination Is At The Heart Of The Home Which Is Filled With Natural Light Thanks To A Wall Of 3 Glass Sliding Doors That Accordion Open When Enjoying The Beautiful Weather And Views Of Lake Reedy. The Courtyard-style, Brick Paver Patio Boasts A ...

2593 Maneshaw Lane, KISSIMMEE

New Photo of Listing #O6053830

$459,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 02

Price Reduced And Offering $5,000 Towards Closings Costs. Fully Furnished Turnkey Townhouse - Unbelievable Investment Opportunity In The Highly Sought After Windsor Hills Community!! Why Not Supplement Your Income With This Proven Income Producing Slice Of Heaven Situated Just 5 Minutes From Disney? Windsor Hills Amenities Are Hard To Beat With Their Waterpark Including A Zero Entry Pool, Splash Zone, Lazy River, Water Slides, And Cabanas, In Addition To Their Game Room, Theater Room, Fitness Center, And Restaurant / Grill Within The Club Ho...

7680 Otterspool Street, KISSIMMEE

New Photo of Listing #O6069148

$459,000

  • 3 Beds
  • 3 Baths

  • 1,416 SqFt

Townhouse

Windsor Hills Ph Two

Amazing **vacation Home/short Term Rental** Opportunity In A 24-hour Guard Gated Community With Resort-style Amenities Just Minutes From Disney!**fully Furnished**welcome To Windsor Hills! This 3 Bedroom, 3 Full Bath End Unit Townhome Has A Private Pool And Comes Fully Furnished. Step Inside This Light And Bright Open Floor Plan And Start Your Tour In The Great Room - Tile Floors Make Maintenance A Breeze And Having The Living, Dining And Kitchen All Open Is Great For Gathering With Family And Entertaining Friends. Your Kitchen Is Well Equip...

7670 Fitzclarence Street, KISSIMMEE

New Photo of Listing #O6068297

$459,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.04 Acres

Townhouse

Windsor Hills Ph 02

Short-term Rental, Windsor Hills Resort Townhome For Sale! This Is An End-unit With No Rear Facing Neighbors Welcome To This Three-bedroom, Three-bathroom, Townhouse Located In The Fabulous, 24/7 Man-gated Community Windsor Hills. This Home Features A Kitchen/dining And Living Room Combination Allowing For Easy Entertaining With Family And Friends. A Spacious Master Bedroom Is Located On The Second Floor With An Ensuite Bathroom With Custom Wood Wall Panel. You Can Find An Additional Bedroom And Guest Bathroom Upstairs With The Third Bedroom...

7680 Sir Kaufmann Court, KISSIMMEE

New Photo of Listing #U8178349

$445,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.04 Acres

Townhouse

Windsor Hills Ph 02

Perfect For Short-term Rentals! Resort-style Community! This Place Has It All With Incredible Rental Opportunities! Welcome To This Three-bedroom, Three-bathroom, Townhouse Located In The Fabulous, 24/7 Man-gated Community Of Vistas At Windsor Hills. This Home Features A Kitchen/dining And Living Room Combination Allowing For Easy Entertaining With Family And Friends. A Spacious Master Bedroom Is Located On The Second Floor With An Ensuite Bathroom. You Can Find An Additional Bedroom And Guest Bathroom Upstairs With The Third Bedroom Locate...

2813 Almaton Loop 305, KISSIMMEE

New Photo of Listing #O6072280

$375,000

  • 3 Beds
  • 2 Baths

  • 1,410 SqFt
  • 0.34 Acres

Condominium

Ventura At Windsor Hills...

This Fully Furnished, Recently Updated, Unit Has To Been Seen To Believe! This 3 Bedroom, 2 Bath Condo Boasts A Freshly Painted Interior As Well As Updated Lvp Flooring In The Bedrooms, Hallway, Dining And Living Area. The Kitchen Has Been Fully Renovated Including New Cabinets, Granite Countertops, Refrigerator, Stove/oven, And Dishwasher. The Bathrooms Have New Toilets, Shower Heads, Faucets, And Granite Countertops. All Water Shut Off Valves Have Been Replaced In The Unit And A New Hot Water Heater Was Recently Installed. Let's Not Fo...

2788 Almaton Loop 303, KISSIMMEE

New Photo of Listing #O6066202

$365,000

  • 3 Beds
  • 2 Baths

  • 1,246 SqFt

Condominium

Ventura Windsor Hills P1

Beautiful Fully Furnished 3 Bedrooms, 2 Bathrooms Condo Unit In The Gated Short Term Rental Community Of Windsor Hills. 2 Miles From Disney, At 192 Kissimmee Closed All Major Orlando Attractions. This Is Turn Key Operation, Located In 3rd Floor With Vinyl Floor Throughout. The Windsor Community Features 24 Hours Security, Resort Style Pool With Splash Pad, Movie Theater, Fitness Center, Game Room, Basketball Court, Tennis Court And Much More.

2784 Almaton Loop 403, KISSIMMEE

New Photo of Listing #S5069878

$364,900

  • 3 Beds
  • 2 Baths

  • 1,246 SqFt

Condominium

Ventura Windsor Hills P1

Welcome To Windsor Hills, Specifically The Ventura At Windsor Hills, An Enclave Of Condominiums Within The World-famous Windsor Hills Resort! This Condo Is Located On The Top Floor Of The Building (the Building Has Elevators), And Because This Unit Is In The Rear Of The Building, It Backs Up To One Of The Recreation Centers That The Community Has To Offer (putting Green, Tennis Courts, And Overflow Parking). Great View! Very Private, With Only One Unit Next Door To This One, No Buildings Directly Behind It, And Foliage Blocking The View From...

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 December 9th, 2022 at 8:04pm EST.