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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23 Properties Found. Showing Page 1 of 2
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2692 Manesty Ln, Kissimmee

Photo of Listing #S5029616

$499,999

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.16 Acres

Single Family / Villa

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...

2635 Daulby St, Kissimmee

Featured Photo of Listing #S5024341

$499,950

  • 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...

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...

2560 Archfeld Blvd, Kissimmee

Photo of Listing #O5840994

$469,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 07

Looking For The Perfect Windsor Hills Home? This Is The One. This Home Features 6 Bedrooms, 4 Full Bathrooms, A Family Lounge, A Dining Area, A Private Pool In A Screened In Lanai And A Deluxe Game Room. This Is The Largest Floor Plan Offered In Windsor Hills. This Home Has Been Recently Updated And Meticulously Maintained. All Hallways And Bedroom Carpet Has Been Replaced With “renter Proof” Vinyl Plank Wood Floors That Are Water And Scratch Resistant. The Adult Bedrooms Are Spa Inspired And The Kid’s Rooms Feature Décor Based On Popular...

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...

7810 Beechfield St, Kissimmee

New Photo of Listing #S5030778

$425,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.20 Acres

Single Family / Villa

Windsor Hills Ph 05

Make An Appointment Today To View This 6 Bedroom/4 Bathroom Fully Furnished Single Family Home On A Corner Lot That Is South Facing In The Well Known Vacation Resort Community Of Windsor Hills. Walking In Is Your Formal Living And Dining Rooms. Kitchen Features Granite And Stainless Steel Refrigerator, Range, Microwave And Dishwasher And This Opens Up To Your Living Room. To Complete The Downstairs You Also Have One Full Bed And Bath And Laundry Room. Enjoy The Covered Patio With Pool And Spa And Brand New Pool Heater For You And Your Guests...

7779 Basnett Cir, Kissimmee

Photo of Listing #G5025535

$425,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 03

Beautiful 6 Bedroom 4 Bathroom Brentwood Model Home In The Sort After Gated Community Of Windsor Hills. Interior Features Includes A Spacious Formal Living And Dining Area; Family Room/kitchen/dinette Combo With Sliding Doors Leading Out To Heated Pool And Spa Area With Covered Lanai. This Home Is Not Overlooked To The Rear And Has Privacy Fence Around The Lower Panels Of The Screened Area. The Bedrooms Comprise Of 2 Large Master Bedrooms Upstairs With King Beds, 1 Queen Bedroom And 2 Twin Bedrooms Share The Upstairs Family Bathroom With Sho...

7753 Grassendale St, Kissimmee

Photo of Listing #O5841926

$415,000

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.16 Acres

Single Family / Villa

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...

2636 Dinville St, Kissimmee

Price
Reduced
Photo of Listing #O5820414

$399,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.17 Acres

Single Family / Villa

Windsor Hills Ph 03

**price Reduced** 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...

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 ...

7783 Teascone Blvd, Kissimmee

Photo of Listing #O5832194

$395,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.21 Acres

Single Family / Villa

Windsor Hills Ph 06

This Beautiful Vacation Home Is Located Only 3 Miles From Disney On An Elevated Lot At The Highest Point Of Windsor Hills. It Is Close To All Of The Attractions And Fun Orlando Has To Offer. The Security Gated Front Entrance Allows Secure Passage Into The Community. Five 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. Tv's In Every Bedroom Provides Plenty Of Entertainment For All When They Are Not Enjoyin...

2631 Archfeld Blvd, Kissimmee

Price
Reduced
Photo of Listing #O5820582

$389,900

  • 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...

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 February 26th, 2020 at 6:15am EST.