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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44 Properties Found. Showing Page 1 of 4
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2625 Daulby St, Kissimmee

Photo of Listing #S5034216

$479,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 02

Very Close To Disney Entrance, Approximately 2 Miles Away Or 10 Min Away, This State-of-the-art Disney-themed 6 Bedroom 4 Bath Lakefront Pool Home Located On One Of The Best Lots In The Highly-sought After Resort Community Of Windsor Hills! The House Is Modelled After Disney Movies Immersing Families Into The Disney Magical Experience. Rooms Are Beautifully Appointed With New Furniture Galore. Relax By The Sparkling Heated Pool With Brick Paver Deck And Inviting Spa By Day And Enjoy The View Of Reedy Lake And The Conservation Area Below. And...

2613 Daulby St, Kissimmee

Price
Reduced
Photo of Listing #T3203218

$479,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family Residence

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...

2600 Archfeld Blvd, Kissimmee

Photo of Listing #O5864758

$445,000

  • 5 Beds
  • 5 Baths

  • 2,342 SqFt
  • 0.17 Acres

Single Family Residence

Windsor Hills Ph 06

Windsor Hills Is One Of The Most Popular Resort Subdivision In The Orlando Kissimmee Area. You Are A Neighbor Of The Mouse (disney), It Only Takes You 5 Minutes Drive To Visit Disney. Windsor Hills Is A Gated And Guarded Community Loaded With All Kinds Of Amenities Like: A Large Clubhouse With A Large Swimming Pool, A Large Slide, Game Room, Fitness Center, Convenience Store, Bar, Sitting Area And More. Then The Playground Is Like An Adventure Land For The Young Ones, Where They Can Climb, Slide, Swing And Yell As Much As They Want To. There...

2546 Archfeld Blvd, Kissimmee

Photo of Listing #O5850449

$439,500

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family Residence

Windsor Hills Ph 07

Stunning Home Located In Highly Desirable Community Of Windsor Hills Within Close Proximity To Disney World. Property Is Turn Key And Move In Ready With Beautiful Furniture And Decoration. Community Is Very Desirable And Offers 24 Hours Security, Gated, Large Community Pool Lagoon Style, Movie Theater Club House, Fitness Center, Game Room And Much More. Home Is Tastefully Decorated With A Very Desirable Floor Plan Highly Desired Among Guests. Home Features 6 Bedrooms, 4 Baths And 2812 Sq Ft Of Space. Gorgeous Gourmet Kitchen Overlooking...

2515 Archfeld Blvd, Kissimmee

Photo of Listing #V4912808

$435,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.23 Acres

Single Family Residence

Windsor Hills Ph 07

Spectacular 6 Bed 4 Bath Fully Furnished Home In The Reserve At Windsor Hills. It Doesn't Get Any Better Than This. This Is An Absolutely Gorgeous Home Located 5 Minutes From Disney In A 24 Hour Guard Gated Resort Community! Beautiful Upscale Furnishings, Granite Counter Tops, Stainless Steel Appliances, Tile Throughout, Screened Heated Pool And Spa With Covered Lanai And Much More. Amenities Within The Community Include: Clubhouse, Movie Theater, Game Room, Fitness Center, On-site Store, Snack Bar, Community Lagoon Style Heated Pool With Ki...

2649 Dinville St, Kissimmee

Photo of Listing #O5861609

$419,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.13 Acres

Single Family Residence

Windsor Hills Ph 03

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 Well Known For ...

7753 Hockendale St, Kissimmee

Price
Reduced
Photo of Listing #S5031358

$417,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 06

This Beautiful Fully Furnished 6 Bedroom, 4 Bath Home With Heated Pool/spa Is Located In A Gated Resort Community Windsor Hills It Can Fit Your Whole Family Or Be Used As Short Term Rental! Tiled Entry Leads Into Living Room As Well As Access To Stairway. Kitchen Has Pass Through To Dining Room And Offers Breakfast Bar And Dinette Area With Sliding Glass Doors. Master Bed Room Offers Walk-in Closet, Private Bath With Dual Sinks, Garden Tub And Separate Shower. Covered Patio Overlooks In-ground Screened Pool. Community Club House Comes With ...

2583 Archfeld Blvd, Kissimmee

Photo of Listing #O5865766

$415,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.19 Acres

Single Family Residence

Windsor Hills Ph 07

What A Beautiful And Well Presented 6 Bedroom 4 Bathroom Home With Pool, Spa With Large Lanai For The Florida Lifestyle. It Was Built In The Last Phase Of The Sought After Resort Of Windsor Hills.the Gated And Guarded Community Offers A Splendid Clubhouse Which Includes A Resort Pool With Slides And Flumes, Movie Room, Gym, Games Room, Convenience Store,ping Pong, Tennis Courts Playground. The Home Includes 2 Master Bedrooms, Formal Living/dining Room, Kitchen And Nook With Stainless Appliances And Family Room Overlooking The Pool Area. The...

7753 Grassendale St, Kissimmee

Photo of Listing #O5841926

$415,000

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 06

Come See This Well Kept 5 Bed 5 Bath Pool Villa That's Only Minutes Away From Disney. This Home Has 2 Master Suites With Walk In Closets Located On The First Floor Overlooking The Pool And Spa Area. This Lovely Windsor Hill Villa Is A Fantastic Short Term Rental Home That Also Includes A Games Room, Granite Counter Tops And Stainless Steel Appliances In The Kitchen And A South Facing Pool. The Community Has An Amazing Array Of Amenities On Offer For Everyone, Water Park, Tennis Courts, Fitness Center, Movie Theatre And Much More! This Beauti...

7785 Basnett Cir, Kissimmee

Photo of Listing #S5013210

$409,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

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 ...

7737 Teascone Blvd, Kissimmee

Photo of Listing #S5034276

$409,000

  • 4 Beds
  • 4 Baths

  • 1,878 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 05

Near Disney, Just Under 2 Miles From The Exit, This Beautiful Home Is As Close As You Can Get To Brand New! Everything About This House Is Super New And Unused. To Start With, This Gorgeous 4 Bedrooms/4 Bath Home Is Located In The Gated Community Of Windsor Hills And Exudes The Disney Experience As The Rooms Have Disney Theme. From Top To Bottom, Everything Has Been Replaced In March 2020 As In Brand New Roof, New Porcelain Tile Floor Throughout, New Interior And Exterior Paint, New Kitchen Including New Granite Countertops And New Backsplas...

7716 Teascone Blvd, Kissimmee

Photo of Listing #O5865142

$400,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 03

South Facing Pool Home On The Fantastic Gated 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 Been Replaced With New Cabinets, Granite Countertops, Glass Backsplash, And Under Cabinet Lighting. There Are Two Master Bedrooms, The Main Ensuite Master Bedroom I...

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 June 1st, 2020 at 3:14am EDT.