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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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 ...

2700 Manesty Lane, KISSIMMEE

New Photo of Listing #O6025323

$640,000

  • 6 Beds
  • 3 Baths
  • 1 Half

  • 2,469 SqFt
  • 0.16 Acres

Single Family Residence

Windsor Hills Ph 03

This This Beautiful Turnkey 6 Bed/3.5 (recently Updated All Tvs, Refrigerator, And Much More - Like New!) Themed Windsor Hills Luxury 2 Story Home Is Located Just Minutes From Walt Disney World And Other Top Vacation Attractions. Located Just 2 Miles From Our Front Gate To Disney's. This Is The Premier Vacation Home Area For Those Looking To Have More Space, The Comforts Of Home, And Still Be Close To All That The Area Has To Offer. This House Has Its Own Pool, Hot Tub, And Game Room! Join Us In World Famous Windsor Hills Community That Has ...

2655 Dinville Street, KISSIMMEE

New Photo of Listing #O6020812

$639,999

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.17 Acres

Single Family Residence

Windsor Hills Ph 03

Fantastic 5 Bedroom Vacation Home In One Of Orlando's Most Popular Resorts! This Spacious 2,382 Sq Ft, 5 Bedroom And 5 Full Bath Open Concept Pool Home In The Windsor Hills Resort Offers Plenty Of Room For A Large Family Or Group. Able To Sleep 12 Comfortably, This Home Features A Princess Themed Room As Well As A Lego Themed Room And A Master Suite Down. There Are A Total Of Three Bedrooms Down And Two Up. The Large Kitchen Includes Stainless Steel Appliances, New Cabinetry, Granite Counter Tops And Offers Plenty Of Cooking And Serving S...

2519 Maneshaw Lane, KISSIMMEE

New Photo of Listing #O6010229

$529,000

  • 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...

7690 Sir Kaufmann Court, KISSIMMEE

New Photo of Listing #O6019773

$494,000

  • 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...

2784 Almaton Loop 404, KISSIMMEE

New Photo of Listing #O6024207

$399,000

  • 3 Beds
  • 2 Baths

  • 1,450 SqFt

Condominium

Windsor Hills

Beautiful 3 Bedroom 2 Bath Fully Furnished Condo In Windsor Hills! This Unit Is On The Top Floor And Is The Largest 3-bedroom Unit In The Community With 9-foot Ceilings Instead Of The Standard Ceilings In Floors 1-3. You Can Use This Unit As A Short-term Rental/vacation Home Or A Long-term Rental Or Live In The Home Permanently. Enjoy Disney Fireworks Every Night From Your Screened In Balcony. Amenities Include Olympic Sized Community Heated Pool, Water Slide/park, Toddler Pool, Fountains, Hot Tub, Huge Clubhouse With Billiard Room, Video Ar...

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,...

2788 Almaton Loop 301, KISSIMMEE

New Photo of Listing #T3369023

$376,000

  • 3 Beds
  • 2 Baths

  • 1,246 SqFt
  • 0.34 Acres

Condominium

Ventura Windsor Hills P1

Lovely Windsor Hills Newly Updated 3 Bedroom 2 Bath Condo. Turn Key And Ready To Go With New Quartz Counters In Kitchen And Both Baths, As Well As Many Updates Tastefully Done As Nice As Can Be. The Original Condos Had Brown Cabinets And Beige Tile Throughout, So This Baby Has Been Very Modernized With A Neutral, Relaxing, And Stylish Gray And White Color Palate. Both Bathrooms Are Updated With New Flooring, White Quartz Counters, And Tasteful Modern Design. This One Is Ready For Vacation Or Rental, Fully Furnished With Everything You Need A...

2784 Almaton Loop 401, KISSIMMEE

New Photo of Listing #S5058783

$369,900

  • 3 Beds
  • 2 Baths

  • 1,246 SqFt

Condominium

Ventura At Windsor Hills P1

Welcome To Windsor Hills, Specifically The Ventura At Windsor Hills, An Enclave Of Condominiums Within The World-famous Windsor Hills Resort! This Condo Is Located On The Top Floor Of The Building (the Building Has Elevators), And The Rear Of This Building Backs Up To One Of The Recreation Centers That The Community Has To Offer (putting Green, Tennis Courts, And Overflow Parking). See The Magic! Pandora, The Dolphin Hotel, Blizzard Beach, And Everest Are All Visible From The Balcony! Step Through The Front Door Into The Open Living Space, W...

7664 Comrow Street 403, KISSIMMEE

New Photo of Listing #S5067360

$359,000

  • 3 Beds
  • 2 Baths

  • 1,246 SqFt

Condominium

Ventura At Windsor Hills...

Amazing 3 Bed 2 Bath Condo On The Fourth (top) Floor. This Great Investment Opportunity Will Convey Fully Furnished And Is A Located In The Desirable Community Of Windsor Hills, Just 2.8 Miles To Disney And Animal Kingdom. The Open Plan Area Boasts A Screened In Balcony Overlooking Reedy Lake With Spectacular Views. Within A Very Short Walk Of Resort Center. The Community Amenities Include A Resort Pool & Hot Tub, Cyber Café Business Center, A Movie Theatre, Game Room, And Restaurant And 24/7 Guard. There Are A Variety Of Themed Play...

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 May 22nd, 2022 at 9:03am EDT.