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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46 Properties Found. Showing Page 1 of 4
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2625 Daulby Street, KISSIMMEE

New Photo of Listing #S5034216

$489,000

  • 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...

7812 Beechfield Street, KISSIMMEE

New Photo of Listing #O5872569

$479,500

  • 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 Street, KISSIMMEE

New Photo of Listing #T3274560

$479,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family Residence

Windsor Hills Ph 02

Windsor Hills, Orlando's 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 Begi...

7751 Hockendale Street, KISSIMMEE

New Photo of Listing #O5916442

$460,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.28 Acres

Single Family Residence

Windsor Hills Ph 06

Highly Desirable Brentwood Model, 6 Bedroom, 4 Full Bath, Is Being Sold Fully Furnished And Rental Ready!! Located In The Gated, Resort Of Windsor Hills (only 2 Miles To Disney) This Property Is On An Oversized, Corner Lot...room For Soccer Play And Space Galore! Open Floor Plan Makes Entertaining Spectaluar With Combined Living/dining And Kitchen/family Room Spaces, Along With Good Sized Bedroom And Full Bath On Main Level. The Kitchen Has Granite Counters And Opens To The Spacious Grand Lanai, With Heated Pool And Spa. Situated In The Las...

7733 Teascone Boulevard, KISSIMMEE

New 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 Bookings! Walking Distance To The New Water Park And Clubhouse! Only A Few Steps Away From The Playground Area! Already Managed By The Top Producing Company For Vacation Rentals, High End Rental Rates And Has Future Bookings!

7755 Hockendale Street, KISSIMMEE

New Photo of Listing #O5909451

$430,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 06

Turn-key Property, Ready To Move In Or To Rent It As A Vacation Home. It The Perfect Investment Property. It’s Tastefully Decorated With All The Comforts Of A Home Away From Home. Fully Furnished. The Resort Has Excellent Amenities: Heated Community Pool And Spa, Game Room, Clubhouse, Fitness Room, Playground, Picnic Area, And Bbq Area, Tennis, Basketball, Volleyball. It Also Has A Convenience Store In The Resort. Even More, Cyber Center, Putting Green, Movie Theater, And An Atm. Water Park Exclusive For Residents And Guests In Windsor...

2589 Archfeld Boulevard, KISSIMMEE

New 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...

7753 Hockendale Street, KISSIMMEE

New 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 ...

7758 Hockendale Street, KISSIMMEE

New Photo of Listing #O5909692

$395,000

  • 4 Beds
  • 4 Baths

  • 1,824 SqFt
  • 0.19 Acres

Single Family Residence

Windsor Hills Ph 06

Must Have It! This 4 Bedroom/4 Bathroom Fully Furnished Has A Great Area With A Pool. Located In A Great Community Very Well Located. Its A Great Community To Vacation Home Rentals. Good Decoration And All Appliances Included! All Of The Bedrooms Are Ensuite Which Is A Great Plus For Multiple Families And A Rental Property. The 2 Master Suites Are Of A Great Size. There Is Tile Located Throughout All Of The Main Living Areas And Bathrooms And Carpets In The Bedrooms. The Home Has A Great Open Floor Plan With Plenty Of Space For Dining. ...

2671 Manesty Lane, KISSIMMEE

New Photo of Listing #S5041801

$395,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 03

Space 6/bed 4/bath Plus A Separate Flex Room Which Can Be Used Office Or 7th Bedroom. Fully Furnished And Tastefully Decorated. 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.

7776 Basnett Circle, KISSIMMEE

New Photo of Listing #O5911674

$390,000

  • 5 Beds
  • 5 Baths

  • 2,342 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 03

Attention!!! Beautiful 5 Bedroom 5 Baths Can Now Be Yours! Sold Fully Furnished And Ready For Vacation. The Home Features Beautiful 5 Bedrooms With Modern Decor, A Game Room With A Pool Table, And An Air Hockey Table, And A Spacious Kitchen-dinning Room Area. Enjoy Florida Scenery While Having Your Morning Coffee At The Patio Area Or Indulge Yourself In The Hot Steaming Spa After A Full Day At The Parks. The Home Is Located Inside Windsor Hills Gated Community. The Resort Features A Heated Pool And Spa, Slides, Clubhouse, Game Room, Theat...

2675 Manesty Lane, KISSIMMEE

New Photo of Listing #O5881871

$389,900

  • 5 Beds
  • 5 Baths

  • 2,342 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 03

This Beautiful, Well Maintained, 5 Bed/5 Bath, 2,342 Sq.ft. Home Is Fully Furnished And Features A Private Pool And Spa With Brick Paver Deck And Screen Enclosure. Additional Features Include Downstairs Primary Bedroom And Bathroom And Huge Game Room/movie Theater. The Windsor Hills Resort Is One Of Central Florida's Premier Vacation Rental Communities With Outstanding Amenities That Include A Huge Swimming Pool, Water Splash Park, Fitness Center, Tennis, Basketball & Volleyball Courts, Ping Pong, Tot Lot, Recreation Park, Clubhouse With G...

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 January 22nd, 2021 at 7:29pm EST.