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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32 Properties Found. Showing Page 1 of 3
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7812 Beechfield St, Kissimmee

New Photo of Listing #O5770561

$459,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

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. 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 Maximum Sun All Day, Perfect For Tanning And Keeping The Water Warm. This H...

2505 Archfeld Blvd, Kissimmee

Photo of Listing #O5742332

$439,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 07

Fantastic South Facing Vacation Rental Property With High End Furniture, Extended Pool Deck, Heated Pool With New Pump, Tile Roof, New Carpet, Nice Game Room With Newly Added Games And Ac In Garage. Excellent Rental Income History In Safe Guard Gated Community If Windsor Hills. Community Offers Fantastic Water Park With Grocery Store And Game House As Well As Huge Additional Pool Besides Own Private Heated Pool .just 12 Minutes To Disney. Home Is In Very Good Condition.

7737 Comrow St, Kissimmee

Photo of Listing #O5705412

$420,000

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 1

Perfect Vacation Getaway Home! This 5 Bedroom, 5 Bathroom Pool Home, Features A Custom Kitchen With 42-inch Cognac Color Cabinetry, Stainless Steel Appliances And Granite Counter Top. With Close To 2,500 Square Feet Of Elegant Living Space, This Well-design Floor Plan Features Spacious Bedrooms Suites, Each Bedroom With Their Own Private Bath. The Two-story Floor Plan Will Bring A Blend Of Contemporary Design And Comfort. Professionally Decorated, This Stylish Interior Home Will Amaze You With Every Single Detail. Built On A Premium Lot, No ...

2536 Archfeld Blvd, Kissimmee

Photo of Listing #O5765291

$416,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.17 Acres

Single Family / Villa

Windsor Hills Ph 07

South Facing Pool With Privacy. These Owners Have Maintained This Home To The Same High Standard As When They Had It Built. Located In The Last Phase Of Windsor Hills. Interior Designer Touches Throughout With Custom Window Treatments, Fans Throughout All The Main Rooms Including Pool Area, Neutral Colors Throughout, Pictures Of Legend Movie Stars, Back Splash Walls, Themed Children’s Rooms. Granite Counter Tops Though Out The Kitchen And Bathrooms. Upgraded Kitchen Cabinets, Fully Stocked For Your Guest. Custom Bar In The Formal Dining/liv...

7809 Beechfield St, Kissimmee

Price
Reduced
Photo of Listing #O5768750

$404,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 05

This Gorgeous 6-bedroom & 4 Bath Pool Home Is Located On A Fabulous Private Conservation Lot In The Premier Gated Resort Community Of Windsor Hills. You Will Love To Relax And Enjoy Your Private Deck Under The Huge Covered Lanai, Or To Bask In The Sun By The Large Heated Pool. This Stunning Vacation Home Is Being Sold Fully Furnished; In Excellent Condition, And Decorated In High Quality Furnishings And Decor. This Complete Resort Feel Home Features A Main Floor Bedroom And Full Bathroom, Five Bedrooms Upstairs; With A Master Bedroom And A H...

7805 Beechfield St, Kissimmee

New Photo of Listing #O5771467

$399,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 05

Welcome Home To Windsor Hills-the Gated, Oasis Resort-where You Can Live And Vacation-located Only 2 Miles From Walt Disney World! Now Available Is This Bright, Brentwood Model Offering 6 Bedrooms, 4 Full Baths, Heated Pool/spa And Over 2800 Sq Ft Of Spacious Living. The Open Floor Plan Includes A Family/great Room, Large Kitchen With Granite Countertops, Lots Of Cabinet Space, Panty And Blended Formal Living/dining Provide Additional Entertaining Space. The Sliders Off The Kitchen Open To The Large, Covered/screened Lanai, No Rear Neighbo...

2616 Daulby St, Kissimmee

Photo of Listing #O5741890

$399,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 02

Brand New Artisan Shingle Roof Just Installed. New Carpet Installed In 2017. 100% Owner Bookings Can Convey With Sale! This Spacious, Well Maintained And Updated 6 Bed Is Located In The Area's Most Sought After Rental Community In The Disney Area. Decorated And Equipped To Attract Premium Rentals, This Home Features 3 King Bedrooms (2 Are Ensuites), A Queen And 2 Themed Twin Rooms. The Garage Is A Game Room Conversion With Pool Table, Foosball And Tv And Game Counsel With Seating. This Home Has Upgraded Cabinets And New Granite In The Kitch...

7785 Basnett Cir, Kissimmee

Photo of Listing #S5013210

$398,500

  • 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!** 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 And Barbecue...

7817 Beechfield St, Kissimmee

Price
Reduced
Photo of Listing #O5768274

$390,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 05

Live-play-work Or Vaca In This Very Safe And Easy Community Close To Disney. Very Well Maintained Vacation Community With A "feels Like Home" Neighborhood. The Community Is Complete With -waterpark, Slides, Game Room, Fitness, Walking Trails And Small Grocery Store For Snacks And More. The Property Has A Resort Feel And This Bright Beauty Has Room To Accommodate The Whole Team, Family Or Group In A Spacious 6 Bedroom Fully Furnished And Super Well-maintained Property. From Tvs, Towels, Beach Balls, And More This Turn Key Property Is A High...

7801 Basnett Cir, Kissimmee

Featured Photo of Listing #S5012816

$385,950

  • 7 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills

This Outstanding 7 Bedrooms 4 Bathrooms Single Family Home Is Located In Windsor Hills And Is The Ultimate Orlando Area Vacation Home And Short Term Rental Property. Fully Furnished With An Open Style Floor Plan That Is Ideal For Entertaining And Spending Time With Family And Friends. The Lovely Kitchen Has A Breakfast Area And Breakfast Nook Ideal For Informal Meals. The Large Master Bedroom Has An Ensuite Bathroom That Features A Garden Tub Standing Shower And Dual Sinks. This Property Features A Game Room In The Garage In Addition To The ...

2616 Bowring St, Kissimmee

Price
Reduced
Photo of Listing #O5758823

$384,900

  • 5 Beds
  • 5 Baths

  • 2,342 SqFt
  • 0.18 Acres

Single Family / Villa

Windsor Hills

Largest 5 Bed In "the Reserve", Located On One Of The Most Private Streets In The Community, Overlooking A Beautiful Landscaped Park And Playground Area. This Executive Style Vacation Home Boasts Double Master Suites With 3 Other Bedrooms, All With Private Baths, Upgraded Furniture, Ceramic Tile In All Living Area's, Kitchen, And Bathrooms, Ceiling Fans Throughout, Games Room In Garage, Professionally Decorated Themed Bedrooms, Private Heated Pool & Spa Backing Onto Stone Wall, And Much More ! Located In One Of The Most Sought After Privac...

2613 Dinville St, Kissimmee

Photo of Listing #S5013827

$379,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.19 Acres

Single Family / Villa

Windsor Hills Ph 3

Fantastic 6 Bedroom 4 Bath Furnished Home In The 24 Hour Guard Gated Windsor Hills Community. Great Floorplan With A Living/dining Room Combo Which Leads To The Eat-in Kitchen And Family Room. One Bedroom And Full Bath On The First Floor. Enjoy Florida Living While Relaxing On The Covered Brick Patio Or Enjoying The Screened-in Pool And Spa. Continue Upstairs To Find A Large Master And Master Bathroom With A Tub, Shower And Dual Sinks. A Second Mini-master And Ensuite Bath Is Also Located On The Second Level. Three Additional Bedrooms And Ba...

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.

Listing information last updated on March 25th, 2019 at 1:45am EDT.