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!

Search Windsor Hills Resort Real Estate Listings

10 Properties Found. Showing Page 1 of 1
View As: Map
Sort by:

2714 Manesty Lane, KISSIMMEE

New Photo of Listing #S5048882

$599,777

  • 7 Beds
  • 4 Baths

  • 3,232 SqFt
  • 0.24 Acres

Single Family Residence

Windsor Hills Ph 05a

Rare Find...high Grossing True Turn-key Opportunity In Windsor Hills! This Spectacular ‘one Of A Kind’ Income Producing Vacation Home Is Situated On An Attractive Oversized Corner Lot With No Rear Neighbors. The Home Was Extensively Renovated In 2020 And Is Arguably The Best Vacation Rental Home In Windsor Hills. Owners Are Currently Liquidating Their Real-estate Portfolio. This Is Your Chance! This Home Offers An Amazing Vacation Rental Income History Despite The Pandemic And All Its Challenges - (march 2021 = 84% Occupancy And Approx. ...

7812 Beechfield Street, KISSIMMEE

New Photo of Listing #O5872569

$519,500

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family Residence

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. Upstair New Carpet All Round.downstair Tile Floor Recently Installed. 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 Maxi...

2677 Manesty Lane, KISSIMMEE

New Photo of Listing #O5926643

$499,700

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 03

Your Dream Home In Windsor Hills, The Closest Five Star Community To Disney (only 2 Miles)! This 6 Bed/4 Bath Home Is Elegantly Renovated Inside And Outside, And Well-maintained! Home Is Located At Highland With An Open And Spacious Backyard View And Enjoying Perfect Privacy Without Rear Neighbors. We Are One Of The Closest Homes To The Amazing Windsor Hills Clubhouse - About 5 Minute Stroll Away. It Is With Year-proving Strong Income Generating Short-term Rental (zoned)! Top Rated On Vrbo Out Of 51,000 Properties In Central Florida. Start Y...

7648 Sir Kaufmann Court, KISSIMMEE

New Photo of Listing #O5934812

$295,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 4

Located In The Thriving Resort Community Of Windsor Hills, This 3/3 Town Home Blends The Perfect Balance Of Privacy And Proximity Being Located Just Minutes Away From Central Florida's Major Highways And Attractions. The Property Is Tastefully Decorated, Well Appointed And Suits Ideally Parties Of Six, Used For Short Term Rental Or As A Second Home. With Its Own Splashpool And Expansive Range Of Community Amenities, This Is An Investment That Can Suit All Types Of Travelers Whether It Be For Relaxation Or Business. Call Us To Schedule Your V...

7650 Comrow Street 303, KISSIMMEE

New Photo of Listing #S5040259

$289,900

  • 3 Beds
  • 2 Baths

  • 1,246 SqFt

Condominium

Windsor Hills Condo / Th...

This Must One Of The Very Best Positioned Condos Available Anywhere Directly Overlooking The Incredible Windsor Hills Water Park. A Luxuriously Furnished And Immaculately Maintained Move-in Ready Home In Coveted Windsor Hills. This Five Star Resort Community Only Minutes From Central Florida's World Renowned Walt Disney World Theme Parks, Universal Studios, Sea World Water Adventure Parks, Numerous Golf Courses, A Vast Array Of Restaurants And Shopping. Ease Of Access To Major Routes Reduces Travel Times To Gulf And Space Coast Beaches. The ...

7673 Otterspool Street, KISSIMMEE

New Photo of Listing #O5938004

$289,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 02

Fantastic Renovated 3 Bed 3 Bath Townhome With Own Private Mini Pool And One Bedroom Downstairs!! This Unit Has Been Completely Renovated In 2017 And Has 4.8 Rating . Shows So Nice And Clean. Nice Location And Walking Distance To Ammenitites. Excellent Booking Throughout The Year Can Be Taken Over. One Of The Best 24 Hour Guard Gated Communities By Disney With Its Own Water Park And Tons Of Recreation Walking Distance!

2550 Maneshaw Lane, KISSIMMEE

New Photo of Listing #O5937904

$285,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 04

Looking For An Immaculate West Facing, Garden View Townhome In Windsor Hills? Look No Further. Schedule A Tour To View This Lovely Townhome. Immaculate, Fully Equipped, Fully Furnished Townhome Located In Windsor Hills, Kissimmee, Just 2.5 Miles From Disney World Resort And Convenient For Other Attractions! Windsor Hills Is Regarded As One Of The Best Vacation Resorts In Central Florida. This Superbly Equipped Two-story Town Home With Private Pool Is Spacious With Over 1440 Sq.ft. Of Living Space. Features Living/dining/kitchen Combo Open Sp...

2809 Almaton Loop 203, KISSIMMEE

New Photo of Listing #O5934524

$267,900

  • 3 Beds
  • 2 Baths

  • 1,246 SqFt
  • 10.00 Acres

Condominium

Ventura At Windsor Hills...

Fully Furnished And Professionally Remodeled. This Condominium Is Used As A Vacation Home. Located In Windsor Hills. This Premier Property Includes Extensive Bookings. This Property Has Everything Requested By The Experienced Traveler. The Community Pool And Clubhouse Are At A Walking Distance. Additionally There Are Two Play Areas Close By. Windsor Hills Features A Resort Style Heated Community Pool, Clubhouse, Game Room, Movie Theater, Sundry Shop, Tennis Courts, Basketball Courts, Putting Green, Sand Volley Ball And More. Hoa Includes Cab...

7650 Comrow Street 402, KISSIMMEE

New Photo of Listing #S5040293

$239,900

  • 2 Beds
  • 2 Baths

  • 1,081 SqFt

Condominium

Ventura At Windsor Hills...

Disney's Nightly Fireworks Display Can Be Enjoyed From The Balcony Of This Great Home Located In The Fabulous Windsor Hills Resort Just Minutes From Walt Disney World & Other Top Vacation Attractions! Windsor Hills Resort Is One Of The Most Popular Short Term Rental Community Next To Disney. This Condos Is Situated Adjacent To The Amazing Windsor Hills Clubhouse And The Beach Style Pool, Water Slide And Spa. There Are A Number Of Additional Amenities At The Clubhouse Including State Of The Art Fitness Center With A Variety Of Weight Training...

7675 Comrow Street 302, KISSIMMEE

New Photo of Listing #S5038826

$219,000

  • 2 Beds
  • 2 Baths

  • 1,081 SqFt

Condominium

Windsor Hills, Ventura A...

Must See This Beautifully Fully Upgraded & Fully Furnished Condo Is Just What You've Been Looking For. West Facing 2 Bedroom 2 Bathroom Third Floor Unit, Excellent For Those Beautiful Evening Sunsets On Your Private Screened In Balcony. Tile Flooring Throughout The Living Room, Dining Room, Wet Areas And Laminate Rooms. 2019 New Inside And Outside A/c Unit! Re-painted In 2019! Windsor Hills Is The Premiere Resort For Disney Vacationers! 15 Minutes To All 4 Parks. Windsor Hills Is One Of The Most Popular And On Of The Closest Vacation Ren...

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.

^ Back to: Windsor Hills Homes

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 April 19th, 2021 at 4:07am EDT.