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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29 Properties Found. Showing Page 1 of 3
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2505 Archfeld Blvd, Kissimmee

Photo of Listing #O5742332

$439,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 07

Fantastic South Facing Vacation Rental Property With High End Furniture, Extended Pool Deck, Heated Pool With New Pump, Tile Roof, New Carpet, Nice Game Room With Newly Added Games And Ac In Garage. Excellent Rental Income History In Safe Guard Gated Community If Windsor Hills. Community Offers Fantastic Water Park With Grocery Store And Game House As Well As Huge Additional Pool Besides Own Private Heated Pool .just 12 Minutes To Disney. Home Is In Very Good Condition.

2584 Archfeld Blvd, Kissimmee

Photo of Listing #G5010484

$420,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.20 Acres

Single Family / Villa

Windsor Hills Ph 07

One Of The Rare Chances To Purchase One Of The Best Located 6 Bedroom Home In Windsor Hills Enclave. The Rear Of The Property Has Unobstructed Elevated Views And Faces West For All Day Sun And Fantastic Sunsets. The Home Has Been Decorated To A High Standard And Has Mainly Been Used For Family Vacations. Great Layout With A Queen Bedroom On The First Floor And 5 Bedrooms On The Second Floor. Open Plan Family Room And Kitchen Ideal For Family Get Togethers. The Kitchen Has Granite Countertops And Stainless Steel Appliances. Great Pool Area Wi...

2546 Archfeld Blvd, Kissimmee

Photo of Listing #O5737630

$420,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 07

Stunning Home Located In Highly Desirable Community Of Windsor Hills Within Close Proximity To Disney World. Property Is Turn Key And Move In Ready With Beautiful Furniture And Decoration. Community Is Very Desirable And Offers 24 Hours Security, Gated, Large Community Pool Lagoon Style, Movie Theatre Club House, Fitness Center, Game Room And Much More. Home Is Tastefully Decorated With A Very Desirable Floor Plan Highly Desired Among Guests. Home Features 6 Bedrooms, 4 Baths And 2812 Sqft Of Space. Gorgeous Gourmet Kitchen Overlooking The F...

7737 Comrow St, Kissimmee

Photo of Listing #O5705412

$420,000

  • 5 Beds
  • 5 Baths

  • 2,494 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 1

Perfect Vacation Getaway Home! This 5 Bedroom, 5 Bathroom Pool Home, Features A Custom Kitchen With 42-inch Cognac Color Cabinetry, Stainless Steel Appliances And Granite Counter Top. With Close To 2,500 Square Feet Of Elegant Living Space, This Well-design Floor Plan Features Spacious Bedrooms Suites, Each Bedroom With Their Own Private Bath. The Two-story Floor Plan Will Bring A Blend Of Contemporary Design And Comfort. Professionally Decorated, This Stylish Interior Home Will Amaze You With Every Single Detail. Built On A Premium Lot, No ...

2621 Archfeld Blvd, Kissimmee

Photo of Listing #O5750433

$389,900

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.21 Acres

Single Family / Villa

Windsor Hills Ph 06

Great Opportunity For Investors. Beautiful 5 Bed/ 5 Bath Single Family Home, Fully Furnished, Located In The Desirable Windsor Hills Community! This Home Features An Open Floor Plan And A Comfortable Living Room Near The Kitchen. The Master Is On The First Floor And Very Spacious. The Resort Features A Large Lagoon-style Pool, Tennis And Volleyball Courts, Fitness Center, Arcade, Putting Green And General Store. Perfectly Situated Within Minutes From Walt Disney World, Sea World And The Famous International Drive. Seller Is Motivated.

2512 Archfeld Blvd, Kissimmee

Photo of Listing #O5726916

$389,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.18 Acres

Single Family / Villa

Windsor Hills

Luxurious Executive Vacation Home, This 6 Bed/4 Bath Pool Home Offer's Professional Upgraded Furnishings And Decors Throughout, Open Floor Plan, Granite Kitchen Countertops, Upgraded Kitchen Cabinets, Ceramic Tile Flooring In All Living Area's And Bathrooms, Screened Covered Heated Pool & Spa, Brick Paver Covered Lanai, Inside Laundry Room, Game Room In The Garage, And Much More ! Excellent Rental History With Bookings In Place To Transfer. Located In The Most Popular Privacy Gated, Resort Style Community Nearest Disney World! Manned Privacy...

2616 Daulby St, Kissimmee

Photo of Listing #O5741890

$384,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 02

Brand New Artisan Shingle Roof Just Installed. New Carpet Installed In 2017. 100% Owner Bookings Can Convey With Sale! 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 Kitch...

2699 Manesty Ln, Kissimmee

Photo of Listing #O5752295

$379,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.17 Acres

Single Family / Villa

Windsor Hills Ph 03

A 6 Bed, 4 Bath Poolhome Located In Windsor Hills, You Are Located Minutes From All Major Highways And Attractions. Boasting A Spacious Kitchen And Living Area, This Property Comes With A Games Room In The Garage And Also A Spacious Second Sitting Area. There Is A Guest Bedroom Downstairs With All Remaining Rooms Above; All Furnished And Rental Ready For Yourself Or Your Guests. The Rear Deck Is Home To A Large Pool And Spa And As A Well Established Rental Property Can Comfortably Accommodate Up To Twelve Individuals. There Are Rentals In Pl...

7755 Tosteth St, Kissimmee

Photo of Listing #O5738048

$379,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 03

Turn Key, Vacation Ready, Luxury Home In The Upscale Community Of Windsor Hills Perfect To Use For Your Family Vacations, An Investment Property, Or As Your Home Sweet Home. New Roof!! Spacious 6 Bedroom With 2 Master Suites And 4 Full Bathrooms, The Location Is Ideal, Just Minutes To Disney! The Community Is 24 Hour Guard Gated And Has Amenities Such As A Water Park, Clubhouse, Game Room, Movie Theater, Fitness Center, Bar, Convenient Store, Tennis Courts, Volleyball Courts, Huge Playground, Putting Green And Barbecue Area. The Garage I...

2626 Dinville St, Kissimmee

Photo of Listing #O5735929

$375,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 3

Welcome To This Beautiful 6 Bedroom With 2 Master Suites And 4 Full Bathrooms Vacation Pool Home In The Heart Of Central Fl, Located In The Premier Guard Gated Resort Community Of Windsor Hills. You May Enjoy Relaxing On Your Over Sized Pool Deck Under The Huge Covered Lanai, Bbqing Or Entertaining Guests, Or Simply Just Basking In The Sun By The Large Heated Pool And Spa. This Stunning Vacation Home Is Being Sold Fully Furnished With Everything You See; In Excellent Condition, Has Been Recently Updated, Decorated, And Has A New Roof. This C...

2681 Manesty Ln, Kissimmee

Price
Reduced
Photo of Listing #S4857708

$365,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 03

***just Reduced*** Short Term Rental Home, Fabulous Views At The Rear Of The Property Looking Towards Disney, Set In An Elevated Position Of Windsor Hills Resort, No Direct Rear Neighbors , Located 3 Miles From Disney. Windsor Hills Is An Amazing Choice For Families Looking For A Family Home Rather Than Staying In A Hotel. This Property Is Perfect For Investors Looking For A Turn Key Property, A Superb 6 Bedroom And 4 Bathroom Open Plan Home (brentwood Model). Fully Furnished, With Upgraded Furniture. Sympathetically Laid Out Making Full Us...

7730 Teascone Blvd, Kissimmee

Photo of Listing #S5011587

$362,500

  • 6 Beds
  • 3 Baths
  • 1 Half

  • 2,469 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 03

Beautiful 6 Bedroom/3 And 1/2 Full Bathroom House With All Furniture And Decoration. Perfect Location In The Gated And Guarded Resort Community Of Windsor Hills, One Of Best Vacation Home Resort In Disney Area. It Is Only 2 Miles From Disney. Two Disney Theme Rooms: Princess Room And Cars Room. This Privately Owned Executive Features 2 Master Suites, Truly South Facing Pool & Spa. The House Is On Teascone Blvd, The Main Road In Windsor Resort And Is About 2-3 Minutes Walking To Community Clubhouse. The Castle Playground Is Right Across The 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.

Listing information last updated on January 16th, 2019 at 11:16am EST.