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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66 Properties Found. Showing Page 1 of 6
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2709 Manesty Ln, Kissimmee

Price
Reduced
Photo of Listing #S4841540

$434,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.24 Acres

Single Family / Villa

Windsor Hills Ph 03

This Beautiful 6 Bedroom Vacation Home Is Located Only 3 Miles To Disney Property And Is Close To All Of The Attractions. Located Within Windsor Hills Resort Community, This Home Features 3 Master Suites, A Private Pool And Spa, A Fully Equipped Kitchen, And A Living Area. This Home Also Offers A Disney’s “mickey Mouse” Themed Twin-bunk Bedroom With A Private Play Area, A Formal Dining Area, A Billiard Area And A Game Room With A Foosball Table And An Arcade Machine As Well As A Home Theater Complete With Theater Seating. With No Rear Neighb...

2635 Daulby St, Kissimmee

Price
Reduced
Photo of Listing #O5490124

$430,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills

This Beautiful 6 Bedroom Vacation Home Is Located Only 3 Miles From Disney And Is Close To All Of The Attractions And Fun Orlando Has To Offer. Located Within Windsor Hills Resort Community, This Home Has Features Like No Other, A Private Newly Remodeled Aruba Twinkling Pool And Spa With Panoramic Views Over Lake Reedy And A Conservation Area, A Whole House Audio System With Ceiling Speakers, Proliphix Home Automation System Controlling The Ac And Pool Heat, New Flat Screen Tvs In All Rooms, A Fully Equipped Gourmet Kitchen With New Samsung ...

2624 Bowring St, Kissimmee

Price
Reduced
Photo of Listing #O5424177

$419,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.23 Acres

Single Family / Villa

Windsor Hills Ph 06

Price Reduction And Seller Financing Available! 25% Down, 15 Years, 6.5% Interest. This Is One Of The Classiest And Most Beautiful Homes In Windsor Hills. Known As "parkside Palace", The Home Features 6 Very Spacious Bedrooms, An Amazing Family Room And Breakfast Nook, A Formal Dining Room, A Great Living Room And Off Course, A Very Relaxing Pool Deck. The Pool Features A Fantastic Spa And It Is A Salt Water System. All Appliances Are Stainless Steel And Th Kitchen Features Granite Countertops. The Garage Has Been Converted Into A Game Room ...

7761 Teascone Blvd, Kissimmee

Photo of Listing #S4849506

$405,000

  • 5 Beds
  • 5 Baths

  • 2,342 SqFt
  • 0.29 Acres

Single Family / Villa

Windsor Hills Ph 06

Investor's Paradise!! Or Dream Home!! Fully Furnished! Corner Lot! Home Is Located In The Most Desired Premier Resort Community Close To It All!! Community Has It All, Community Pool, Tennis Courts, Fitness Center, Hd Movie Theater, Ping Pong Table, Billiard Table, Gated, Shop. Community Offers Shuttle Service To The Parks, Added Bonus!! Make This Home Your Home Away From Home!! Call Me Today!!

7762 Teascone Blvd, Kissimmee

Photo of Listing #S4850739

$400,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 09

One Of The Best Lots In All Of Windsor Hills Resort With No Rear Neighbors And A Beautiful Rare Green Belt View. This Magnificent Home Comes Fully Furnished With 6 Bedrooms, 4 Bathrooms And 2,812 Square Feet Of Spacious Living. A Fully Equipped Kitchen With Granite Counters, 42 Inch Wood Cabinets And Ss Appliances. Open Plan Floor With Family Room, Living Room, Dining Room, Kitchen And 1 Bedroom Downstairs. The Garage Is Converted To A Games Room. Plenty Of Room For Everyone, Whether You Entertain Inside Or Outside. Enjoy The Florida Sun Rel...

7743 Teascone Blvd, Kissimmee

Price
Reduced
Photo of Listing #O5507796

$399,999

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 06

*full 3d Matterport Walkthrough Available - Please Check The Listing For Link* Welcome Home To This Superbly Appointed 6 Bed/4 Bath Pool And Spa Property Located In Windsor Hills. Boasting A Number Of Upgrades And A Fully Equipped Games Room, This Fully Furnished Retreat Suits All Guests And Families In All Shapes And Sizes; Reunions, Family Getaways And Professional Travelers Can Enjoy The Comfort, Tranquility And Proximity To Attractions And Highways That Windsor Hills Brings And At A Very Affordable Price. The Strength Of This Property Is...

2625 Daulby St, Kissimmee

Photo of Listing #S4850994

$399,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 02

Spectacular 6 Bedroom Lakefront Pool Home Located On One Of The Best Lots In The Highly Sought After Community Of Windsor Hills! You And Your Guests Will Love To Relax By The Sparkling Heated Pool With Its Brick Paver Deck And Inviting Spa All Day And Enjoy The View Of Reedy Lake And The Conservation Area. And When You Want To Get Out Of The Sun For A Bit There's Plenty Of Room On The Huge Covered Lanai To Sit Back And Sip A Cold Drink. When The Sun Sets You Can Go Back Out And You'll Be Treated To The Disney Fireworks Each And Every Night.....

7753 Grassendale St, Kissimmee

Price
Reduced
Photo of Listing #S4839868

$398,950

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 06

Are You An Investor Looking For The Ultimate Orlando Rental Property? Windsor Hills Is The Perfect Investment For You! Located Just 3 Miles From Disney, Windsor Hills Is A Popular Choice For Families Looking For A Cheaper Alternative Than Staying On Disney Property. This Turn Key Property Features The Oversized Seville Floor Plan Boasting An Expansive 5 Bedroom/5 Bathroom Layout. At Just Under 2,500 Sqft This Stunning Home Comes Fully Furnished With Beautiful Furniture In Airy Brown, Aqua, And Hues. Within The First Floor Tenants Will Find A...

2616 Daulby St, Kissimmee

Price
Reduced
Photo of Listing #O5468210

$395,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills

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 Kitchen As Well As Brand New Carpet Installed This Summer. This Property Also Features Newly Installed Gutters. Patio...

2551 Archfeld Blvd, Kissimmee

Price
Reduced
Photo of Listing #O5491453

$390,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.23 Acres

Single Family / Villa

Windsor Hills Ph 07

A House That Stands Out In The Area's Most Popular Rental Community. Look At This Huge Corner Lot With Exceptional Landscaping And A Large Addition To Rear Of The Pool Area. Its A Unique House That Stands Out From The Rest. Privacy Bushes Surround The Large Pool Deck Which Features Seating For 10 And With 5 Loungers Still Room To Spare! Professionally Decorated Including Window Treatments, Themed Twin Rooms And A Murals In The Garage Game Room Which Also Includes An Extra Full Size Refrigerator. This Vacation Home Is Turn Key And ...

2698 Manesty Ln, Kissimmee

Price
Reduced
Photo of Listing #O5504764

$389,790

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 03

Only 4.5 Miles To Disney’s Gate. This Home Offers One Of The Most Desirable Floor Plans In Windsor Hills With 5 Beds And 5 Baths, This Well- Kept Home Is Located On A Conservation Lot. It Is Walking Distance To Tennis Courts And The Clubhouse. Tastefully Decorated & Furnished With Neutral Colors Throughout And Offered As A Turn Key Property. Boasting 2 Master Suites With King Sized Beds On The First Floor, One Queen Master Suite On The First Floor And Twin Beds On The Second Floor. Fully Stocked Kitchen And Ready To Go Overlooking The Fami...

7809 Beechfield St, Kissimmee

Photo of Listing #O5500860

$389,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 05

Priced To Sell! Stunning.....6 Bedroom 4 Bath Turnkey Vacation Home In Windsor Hills. You Can Also Use This Home As A Permanent Residence, Rent It Short Term Or Rent It Long Term. Beautiful 6 Bedroom 4 Bath Fully Furnished Home Located In The Reserve At Windsor Hills. No Rear Neighbors! Watch The Disney Fireworks Every Evening While Relaxing In Your Pool. This Home Is Completely Turn Key With Bookings In Place. Windsor Hills Is A 24 Hour Guard Gated Community 5 Minutes From Disney. This Home Has An Upgraded Luxury Furniture Package, Tile Thr...

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 October 20th, 2017 at 11:03pm EDT.