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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2532 Archfeld Boulevard, KISSIMMEE

New Photo of Listing #S5068303

$760,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.33 Acres

Single Family Residence

Windsor Hills Ph 7

Amazing Fully Furnished Turn Key Property, Less Than 10 Miles Away From Disney Theme Parks, In The Highly Sought After, Gated, Resort Community Of Windsor Hills, Don't Let This Fantastic Opportunity Pass, Be The Owner Of A Fantastic Primary Residence, Vacation Home Or Investment Rental, This Beautiful 6 Bedroom, 4 Bathroom, Game Room Set Up In The Garage, And Enjoyable Heated Pool And Spa With No Rear Neighbors. Windsor Hills Is Kissimmee's Premier Resort Community, Featuring A 24 Hour Manned Gate, A Resort Style Swimming Pool, Water Sli...

7755 Hockendale Street, KISSIMMEE

New Photo of Listing #O6013903

$723,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

Windsor Hills Ph 06

It's Hard To Get Any Closer To Disney Than Windsor Hills Resort! Windsor Hills Is One Of The Closest Short-term Vacation Rental Resorts To The Entrance Of Walt Disney World, Only Two Miles To World Drive. This Home Can Be Your Next Second Home, Short Term Vacation Rental, Or Primary Residence. Currently The Home Has A Great Management Company In Place And The Calendar Is Packed With Future Bookings. Details Happily Provided Upon Request. The Home Has Been Well Maintained And Is Being Sold Fully Furnished And Turn-key. Windsor Hills R...

2627 Daulby Street, KISSIMMEE

New Photo of Listing #S5070023

$670,000

  • 5 Beds
  • 5 Baths

  • 2,342 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 02

Dont Miss This Beautiful 5 Bed/ 5 Bath Home On The Lake In Top Rated Windsor Hills Resort! Only 2 Miles From Disneyworld! Fully Furnished, Best Location In Community On Lake With Pool Not Directly Overlooked From Patio Providing Privacy And Covered Screened Lanai To Relax And Enjoy Your Leisure! Very Close Also To The Full Amenity Center. Newer Game Room And Furnishings With Disney Themed Rooms! It's Hard To Get Any Closer To Disney Than Windsor Hills Resort! The Closest Short-term Vacation Rental Resort To The Entrance Of Walt Disney World...

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

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 Guests Every Year. Upon Entering The Home You Will See An Open Floo...

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 ...

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...

7683 Fitzclarence Street, KISSIMMEE

New Photo of Listing #O6038856

$503,333

  • 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...

7673 Otterspool Street, KISSIMMEE

New Photo of Listing #O6022519

$499,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 02

**2 Miles From Disney Theme Parks** Beautiful 3-bedroom 3-bathroom Townhome In Highly Desirable Windsor Hills Resort. Amazing Income Potential For Investors! Property Produced Over $50,000.00 In Gross Rental Income Since June Of 2021! This Townhome Is Just Steps From The Community Resort Style Pool And All The Incredible Amenities Which Include A Clubhouse, Fitness Center, Tennis Courts, Game Room, And Dog Park. This Fantastic Fully Furnished Townhome Features An Open Concept Kitchen, Dining & Living Room Combination Ideal For Entertaining W...

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 ...

7690 Sir Kaufmann Court, KISSIMMEE

New Photo of Listing #O6019773

$475,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 02

Fully Furnished 3bed 3bath In One Of The Most Popular Gated Resort Communities In Addition To Your Own Private Pool!! This Beautiful Townhome Is Only Minutes From Disney, Other Theme Parks, Shopping, And Many Great Restaurants That Make It The Perfect Home For Full-time Owners, Tenants, Or Short Term Rentals. As You Enter The Home, You're Greeted With An Open Concept Kitchen, Dining, And Living Room With A View Of The Private Pool Creating The Perfect Entertainment Space. As You Make Your Way Upstairs You Will Find A Spacious Master Suite Fe...

2515 Maneshaw Lane, KISSIMMEE

New Photo of Listing #O6027814

$469,900

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 4

*only 4 Miles To Walt Disney World - One Of Closest Communities* Ready To Own The Perfect Investment Property? This Fully-furnished Windsor Hills Townhome Is Newly-updated And Ready For You! Walk Into The Refreshed Kitchen With Granite Countertops, Stainless Steel Appliances, And Spacious Breakfast Bar. 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 ...

2785 Almaton Loop 103, KISSIMMEE

New Photo of Listing #S5067941

$384,999

  • 3 Beds
  • 2 Baths

  • 1,246 SqFt

Condominium

Ventura At Windsor Hills...

First Floor End Unit! Fully Furnished 3 Bedroom 2 Bath Condo In Windsor Hills. The Cozy Guest Bedrooms Have Been Tastefully Decorated And There Is An Additional Laundry Room For Your Convenience. This 24 Hour Guard Gated Community Is In The Perfect Location, Use As A Vacation, Short-term Or Long Term Rental Home. Olympic Sized Communal Heated Pool, Water Slide/park, Toddler Pool, Fountains, Lagoon And Jacuzzi Spa. Huge Clubhouse With Billiard Room, Video Arcade, Wi Fi Hot Spot, Business Center, Convenience Store & Bar, Casual Dining Terrace,...

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 June 30th, 2022 at 9:49pm EDT.