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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24 Properties Found. Showing Page 1 of 2
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2613 Daulby St, Kissimmee

Photo of Listing #T3203218

$499,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 02

Windsor Hills, Orlandos Closest Five Star Community To Walt Disney World, Invites You To See One Of Orlandos Most Sought After Vacation Rentals With $55,000 In Revenue Received For Calendar Year 2019 And $35,000 Already Booked For Upcoming Calendar Year 2020. While In This Vacation Home You Will Retain Some Of That Same Magical Disney World Feeling You Get While Inside The Theme Parks. Our Disney World Themed Rooms Along With Rare, One Of Kind, Theme Park Banners, Signs And Props That Were Once Used Inside The Disney Parks Are Just The Begin...

2589 Archfeld Blvd, Kissimmee

Photo of Listing #O5820932

$427,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 7

Attention! Beautiful 6 Bedroom 4 Bath Home Is Now For Sale. Located Minutes From The Main Orlando's Best Attractions, This Home Is A Perfect Escape From The Routine Of Daily Life. Home Is Located In The State Of Art Vacation Community Windsor Hills Resort And Is A Piece Of Paradise That You, Yes, You Can Now Own. 6 Gorgeous And Modernly Designed Rooms 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 Inch Flat-screen Tv, Ideal For Family Movie Time. The Poo...

2615 Archfeld Blvd, Kissimmee

Photo of Listing #O5814068

$420,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.21 Acres

Single Family / Villa

Windsor Hills Ph 06

This Beautiful Vacation Home Is Located Only 3 Miles From Disney And Is Close To All Of The Attractions And Fun Orlando Has To Offer. The Security Gated Front Entrance Allows Secure Passage Into The Community. Six Bedrooms Including Two Large Master Bedrooms With Private En Suite, Spacious Family And Living Room Areas, Dining Room And Breakfast Nook Ensure There Is Plenty Of Room To Eat And Relax. A Games Room Garage Convert And Flat Screen Tv's Combination Provides Plenty Of Entertainment For All When They Are Not Enjoying The Fantastic Hea...

2636 Dinville St, Kissimmee

Photo of Listing #O5820414

$409,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.17 Acres

Single Family / Villa

Windsor Hills Ph 03

A 6 Bed, 4 Bath Poolhome Located In Windsor Hills, You Are Located Minutes From All Major Highways And Attractions. Boasting A Spacious Kitchen And Living Area, This Property Comes With A Games Room In The Garage And Also A Spacious Second Sitting Area. There Is A Guest Bedroom Downstairs With All Remaining Rooms Above; All Furnished And Rental Ready For Yourself Or Your Guests. The Rear Deck Is Home To A Large Pool And Spa And As A Well Established Rental Property Can Comfortably Accommodate Up To Twelve Individuals. There Are Rentals In Pl...

2550 Archfeld Blvd, Kissimmee

Photo of Listing #S5021731

$409,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 07

This Beautiful And Immaculate Property Sits On Windsor Hills, Close To The 192, I4 And Theme Parks. The Sub-division Has A Club House With Many Amenities For Guests And Homeowners . This Home Is In Beautiful And Very Popular Windsor Hills And Is Finished With A Tile Roof. As You Enter The Home, You Will Be Greeted By Gorgeous Furnishings, Spacious Floor Plan And Fabulous Kitchen. Enjoy Preparing Feasts In The Modern Kitchen, Featuring Modern Stainless Steel Appliances And Granite Worktops. The Pool And Hot Tub Are Great For Enjoying The Perf...

2609 Dinville St, Kissimmee

Photo of Listing #O5824587

$400,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 03

Rental Ready Investment Property In The Fantastic Gated Community Of Windsor Hills. This Pool Home Has 6 Bedrooms, 4 Bathrooms, And A Game Room. There Is An Open And Spacious Floor Plan Downstairs Consisting Of The Living Room, Kitchen, Dining Room, And Family Room. There Is Also One Bedroom And One Bathroom On The Lower Level. The Remaining Bedrooms Are All Upstairs And Include The Master Bedroom With An Ensuite Bathroom Featuring Dual Sinks, Tub, And Separate Shower. The Kitchen Boasts Beautiful Wood Cabinets That Were Replaced A Few Years...

2635 Daulby St, Kissimmee

Featured Photo of Listing #S5024341

$399,950

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills

The Most Spectacular View Awaits You In This 6 Bedroom 4 Bathroom Home In The Fantastic Gated Community Of Windsor Hills. This Two-story Home Features 1 Bedroom Downstairs, An Open And Spacious Floor Plan For The Living Room, Kitchen, Dining Room And Family Room. All Remaining Bedrooms, Including The Master Bedroom With An Ensuite Bathroom Featuring Dual Sinks, Tub And Separate Shower Are Upstairs. All Rooms Are Fully Furnished And No Detail Was Left Behind. Window Treatments Dress All The Windows. The Kitchen Boasts Beautiful Wood Cabinet...

2631 Archfeld Blvd, Kissimmee

Price
Reduced
Photo of Listing #O5820582

$399,900

  • 5 Beds
  • 5 Baths

  • 2,342 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 05

Welcome To Windsor Hills, One Of Orlando's Top Rated Vacation And Resort Communities. Located Just 15 Minutes From Disney And International Drive. Here You'll Find Entertainment For All! Come Enjoy A Relaxing Poolside Escape Or A Maybe Day Of Fun At The Splash Pad.community Also Has On Site Movie Theater, Gymnasium, And Snack Shop. Tucked Away In The Back Of The Neighborhood You Will Find Your 5 Bedroom 5 Bath Home Waiting To Welcome You And Your Guest. This Home Has 2 Master Suites With Walk In Closets Located On The First Floor And 3 M...

7785 Basnett Cir, Kissimmee

Photo of Listing #S5013210

$399,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

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 ...

2538 Holtrock St, Kissimmee

New Photo of Listing #O5825410

$399,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.20 Acres

Single Family / Villa

Windsor Hills Ph 07

This 5 Bedroom, 5 Bathroom Two Story Home Is Located In The Guard Gated Windsor Hills Resort, Just A 4 Mile Drive To Walt Disney World. The Home, Which Is Currently Being Used As A Short Term Vacation Rental, Is Being Sold Fully Furnished And Turn Key. The Kitchen Is Fully Equipped With All Major Appliances And A Breakfast Nook. The Large Master Bedroom Suite With A Spacious Master Bathroom Is Conveniently Located On The First Floor. The Home Has Had Many Updates And Renovations Such As An Alarm System, Washer/dryer, New Pool Pump And Energy...

7714 Teascone Blvd, Kissimmee

New Photo of Listing #O5825201

$399,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 03

South Facing Pool Home On The Fantastic Windsor Hills Resort. With 5 Bedrooms, 5 Bathrooms, Games Room, Swimming Pool And Spa, This Home Will Make A Great Vacation Home Or Continue To Use It As An Income-producing Short Term Rental Property. There Is A Solid Rental History And All Future Bookings In Place Will Convey With The Sale, Subject To Guest Approval. The Kitchen Has Solid Countertops And Stainless Steel Appliances. There Are Two Master Bedrooms, The Main Ensuite Master Bedroom Is Downstairs And The Second Master Bedroom Is Upstairs. ...

7775 Teascone Blvd, Kissimmee

Price
Reduced
Photo of Listing #O5810219

$398,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.17 Acres

Single Family / Villa

Windsor Hills Ph 06

Fully Furnished, Spacious 6 Bedroom, 4 Bath Pool & Spa Vacation Home In One Of Orlando's Most Demanded Vacation Rental Communities. New Carpet On Second Floor And New Flooring On First Floors Well As A Brand New Pool Heater Installed Aug 2019. The First Floor Consist Of Formal Living And Dining Rooms, Spacious Kitchen With Granite Counter Tops, Breakfast Bar, Impressive Great Room And Games Room In The Garage. The Convenience Of A First Level Bedroom With Adjacent Bathroom Completes The Layout Downstairs. Upstairs You Will Find A Large Mast...

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 November 19th, 2019 at 12:16pm EST.