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!

Search Windsor Hills Resort Real Estate Listings

67 Properties Found. Showing Page 1 of 6
View As: Map
Sort by:

2692 Manesty Ln, Kissimmee

Photo of Listing #S5037763

$499,999

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills

Attention Investors! You Now Have The Opportunity To Own One Of The Top Producing Homes In Windsor Hills. This 5 Bed 5 Bath Home Is Designed For Performance From Top To Bottom. Gorgeous Furnishings. En Suite Bathrooms. Themed Bedrooms. Fully Converted Air Conditioned Garage With Arcade Games And Projection Tv! Your Guests Will Enjoy The Beautiful Florida Sun With This West Facing Pool And Hot Tub. Already Managed By The Top Producing Company For Vacation Rentals, High End Rental Rates And All Future Bookings Convey! Did I Mention That Windso...

7812 Beechfield St, Kissimmee

Photo of Listing #O5872569

$499,500

  • 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. Upstair New Carpet All Round.downstair 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 Maxi...

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...

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 And 2 New Acs. 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 A...

7733 Teascone Blvd, Kissimmee

Photo of Listing #S5035944

$450,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills

An Investors Dream! This Beautiful Turnkey 5 Bedroom 5 Bathroom Home With A Converted Garage And Two Complete Themed Bedrooms, Comes With Great Bookings! Walking Distance To The New Water Park And Clubhouse! Only A Few Steps Away From The Playground Area! It Has Full Bookings So That Makes It Difficult To View In Person So Check Out The Incredible Pictures Provided By The Management Company But Absolutely Check The Calendar For Dates!

2546 Archfeld Blvd, Kissimmee

Price
Reduced
Photo of Listing #O5850449

$429,000

  • 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...

2589 Archfeld Blvd, Kissimmee

Photo of Listing #O5880757

$427,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 7

Attention!! Beautiful 6br/4ba Home Is Now For Sale. Located Only Minutes From The Main Orlando Attractions, This Home Is A Perfect Escape From The Routine Of Daily Life. Home Is Located In State-of-the-art Vacation Community Of Windsor Hills Resort And Is A Piece Of Paradise That You, Yes, You Can Now Own. Six Gorgeous And Modern-designed Bedrooms 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-in. Flat Screen Tv, Ideal For Family Movie Time. The Poo...

2674 Manesty Ln, Kissimmee

Photo of Listing #O5880798

$419,900

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.20 Acres

Single Family Residence

Windsor Hills Ph 3

**just Renovated In May 2020** Come See This Stunning Windsor Hills Vacation Rental For Yourself! This Fantastic 5 Bedroom / 5 Bathroom Windsor Hills Villa Has Been Beautifully Renovated Just This Spring. Dual First Floor Master Suites With En-suite Bathrooms. Third Bedroom And Bath Are Also Located On The First Floor. Remaining Two Bedrooms And Bathrooms Are Located Upstairs Giving Plenty Of Room For Everyone To Have Their Own Space To Relax After A Long Day Enjoying All Central Florida Has To Offer. The Pool Heater Was Also Replaced In Fal...

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 ...

2709 Manesty Ln, Kissimmee

Featured Photo of Listing #S5035100

$415,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.24 Acres

Single Family Residence

Windsor Hills

Outstanding Views Await You At This Fully Furnished 6 Bedroom 4 Bath Home In The Fantastic Gated Community Of Windsor Hills Resort. This Two-story Home Features One Bedroom Downstairs, An Open And Spacious Floor Plan For The Living Room, Kitchen, Dining Room And Family Room. The Kitchen Area Provides Plenty Of Seating For Everyone For Entertaining. All Remaining Bedrooms, Including The Master Bedroom With An Ensuite Bathroom Featuring Dual Sinks, Tub And Separate Shower Are Upstairs. Step Out Onto Your Covered Porch And Enjoy The Private An...

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...

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.

^ Back to: Windsor Hills Homes

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 August 11th, 2020 at 2:00pm EDT.