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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22 Properties Found. Showing Page 1 of 2
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2621 Dinville Street, KISSIMMEE

New Photo of Listing #S5071702

$675,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 03

Welcome To Windsor Hills One Of The Most Premiere Resorts In The Area Due To Its Proximity To Disney Theme Parks, Not To Mention The Wealth Of Amenities Within The Community. The Community Is Zoned For Short Term Rental And Is A Vacation Goers Paradise Which Is Why These Homes Rent So Well. This 6 Bedroom 4 Bath Home Is Among The Models Of Home That Rent The Best. Complete With A Heated Pool & Spa And A Garage /game Room Boasting A Pool Table And Foosball. The Screened In Lanai Affords Plenty Of Covered Area To Lounge By The Pool. There I...

7820 Beechfield Street, KISSIMMEE

New Photo of Listing #O6042940

$654,000

  • 5 Beds
  • 5 Baths

  • 2,342 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 5

Come See This Spectacular 5 Bedrooms, 5 Bath, Fully Furnished Vacation Home In Gated Community Of Windsor Hills! Conveniently Located! With Easy Access To Highways, Near All The Theme Parks, Shopping, Restaurants! The Resort Has Amazing Amenities: Gym, Movie Theater, Game Room, Tennis Court, Volleyball. When You Are Ready To Relax Make Your Way From Family Room Through The Sliding Glass Doors Into The Screened Patio/lanai With A Beautiful Pool! Florida Living At Its Best! Schedule Your Showing Today!

7767 Tosteth Street, KISSIMMEE

New Photo of Listing #S5072623

$650,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 03

The Gorgeous Fully Furnished Home Offers 6 Bedrooms And 4 Bathrooms. Has One Guest Room On The First Floor With A Spacious Bathroom Right Next To It. Has A Large Kitchen With Breakfast Bar With A View To The Family Room And Also The Formal Dinning Area. The Formal Dining Room And Living Room Combo Are Located At The Entrance Of The Home. The Extra Large Master Bedroom Is Situated On The Second Floor With A Walk-in Closet, Shower, Bathtub And Double Vanity. There Is Also A Junior Master With The 3 Other Bedrooms On The Second Floor. House Was...

7724 Comrow Street, KISSIMMEE

New Photo of Listing #S5068050

$650,000

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.20 Acres

Single Family Residence

Windsor Hills Ph 1

Back To The Market Due To Buyer Finance, Can Be Shown 7/28-8/2. See Full Video Walk Through Tour In The Link Above*** Simply Stunning Conservation View Home! One Of The Nicest Lots In Windsor Hills! This Tastefully Decorated, Very Well Kept Home Has A Great View Onto A Large Conservation Area, So No Rear Neighbors And Peaceful Ambience. Location! Windsor Hills Resort Is A 24-hour Guard Gated Resort Community, Located Just A Short Drive From Disney World. The Community Has An Excellent Reputation As A Rental Community Attracting Returning Gue...

7822 Beechfield Street, KISSIMMEE

New Photo of Listing #S5064471

$649,995

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 5

Nice Tiled Roof Home With South Facing Private Pool In The Prestiage 24/7 Man Guarded Community Windsor Hills! This Fully Furnished Home Is 2,382 Sq. Ft And Features Five Bedrooms And Five Baths With An Open Dining Area, Spacious Living Room, And Cozy Breakfast Nook, Master Bedroom Is Located On The First Floor Plus Two Extra Bedrooms, Two Additional Bedrooms On The Second Floor. The Attached 2-car Garage Has Been Converted Into A Game Room. Beautiful Landscaping Surrounds The Home, And A Scenic Park Sits Directly Across The Street. Windsor ...

7750 Grassendale Street, KISSIMMEE

New Photo of Listing #S5072921

$649,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.19 Acres

Single Family Residence

Windsor Hills Ph 06

This Popular Rental Home Is Located In The Gated Resort Of Windsor Hills Only A Short Distance From Walt Disney World And All Of Central Floridas' Attractions. This Home Proudly Sits On A Large Corner Lot With No Rear Neighbor's, Mature Landscaping And A South Facing Pool Giving You Plenty Of Sunshine All Day Long. This Fully Furnished Home Has Been A Very Popular Rental Home. As You Enter You Will Love This 5 Bedroom 5 Bathroom Home With A Private Pool And Spa And A Huge Deck With Screened In Patio. There Are 2 Bedrooms And 2 Bathrooms Ups...

2700 Manesty Lane, KISSIMMEE

New Photo of Listing #O6045569

$637,500

  • 6 Beds
  • 3 Baths
  • 1 Half

  • 2,469 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 03

New Photos! Home Away From Home In The Popular Vacation Destination Of Windsor Hills, Located Minutes From Walt Disney World And Other Top Vacation Attractions! Large, Gated Community With A Water Park, Water Slides, Resort Style Pool, Fitness Center, Playground, Recreation Park, Movie Theatre, Windsor Marketplace & Grill, Game Room, Cyber Cafe, Ping Pong, Tennis, 7 Hole Putting Green, Basketball, Dvd Rentals, Atm And So Much More, You Can Stay In The Resort And Have Fun Or, Go To The Nearby Local Top Attractions And Parks, Restaurants, Shop...

7742 Comrow Street, KISSIMMEE

New Photo of Listing #S5072608

$630,000

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 01

Investment Opportunity!! House Fully Furnished. Entering The Home You Will Be Welcomed Into The Foyer With A High Ceiling. On Your Left Is The Very Spacious And Well-lit Kitchen With Three Large Windows Giving You Plenty Of Natural Light. Along With An Area To Accommodate A Table . Upon Entering To The Right Of The House You Will Find The Guest Bathroom That Has Access To A Comfortable Bedroom On The First Floor. The 2 Car Garage Is Being Used As A Game Room With A Washer And Dryer Included. This Home Has A Beautiful Formal Dining Room Whe...

2519 Maneshaw Lane, KISSIMMEE

New Photo of Listing #O6010229

$510,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 04

Upgrades Galore! An Updated And Turnkey 3 Bed 3 Bath Townhome In The Popular Community Of Windsor Hills Resort Can Now Be Your Vacation Home, Primary Home, Or Short-term Rental Investment. This Amazing Rental Is In Spectacular Condition And Very Well Taken Care Of With Many Recent Updates Such As New Flooring And Kitchen Counters. Pool Resurfaced In 2021. Newer Ac, Pool Heater, And Water Heater. Windsor Hills Is An Excellent Resort With World-class Amenities That Offers: 24-hour Gated Community Security, Water Park, Gym, Parks, Tenni...

2592 Maneshaw Lane, KISSIMMEE

New Photo of Listing #O6039658

$505,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.04 Acres

Townhouse

Windsor Hills Ph 02

Location Location Location!! Closest Community To Disney World!! This Fully-furnished Windsor Hills Townhome Is Recently Renovated And Ready For You! This Is A Beautiful Corner Townhome, Walking Distance From The Club House. The Living And Dining Area Has Plenty Of Room For Guests And Features A Large Sliding Glass Door With Views To The Pool Area! You Have One Guest Bedroom Downstairs Which Connects To A Downstairs Bathroom, Allowing For Added Privacy. Upstairs You Have A Guest Suite, Complete With Its Own Adjoining Bathroom And Large Stora...

7661 Fitzclarence Street, KISSIMMEE

New Photo of Listing #O6035129

$479,900

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills

This Fully-furnished, Well Maintained Townhome Offers 3 Bedroom En-suites Spread Over A Spacious 1440 Square Feet. It Is A Perfect Layout With One Bedroom Suite On The First Floor, And The Two Other Bedroom En-suite's Upstairs Providing Maximum Privacy. The Open Living Room, Dining Area, And Kitchen Combination Is At The Heart Of The Home Which Is Filled With Natural Light Thanks To A Wall Of 3 Glass Sliding Doors That Accordion Open When Enjoying The Beautiful Weather And Views Of Lake Reedy. The Courtyard-style, Brick Paver Patio Boasts A ...

7683 Fitzclarence Street, KISSIMMEE

New Photo of Listing #O6038856

$473,333

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.04 Acres

Townhouse

Windsor Hills Ph 02

***turnkey Rental Townhome*** Come See This Tastefully Furnished End-unit Townhome In Beautiful Windsor Hills Resort! This Townhome Has Been Renovated By The Current Owners To Standout On The Short-term Rental Market And Is Ready To Hit The Ground Running For The New Owner And Even Comes With Future Bookings All The Way Into 2023! Windsor Hills Is Known As Arguably The Best Short Term Rental Resort In The Entire Disney Corridor! Location Is Unbeatable Being A Short 5 Min Drive To Disney & Close To Other Major Attractions Such As Universal, S...

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 August 19th, 2022 at 12:03am EDT.