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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17 Properties Found. Showing Page 1 of 2
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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.

2545 Archfeld Blvd, Kissimmee

New Photo of Listing #O5798867

$430,000

  • 5 Beds
  • 5 Baths

  • 2,480 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills

Spectacular 5 Bed 5 Bath Fully Furnished Home In The Reserve At Windsor Hills. It Doesn't Not Get Any Better Than This. This Is An Absolutely Gorgeous Home Located 5 Minutes From Disney In A 24 Hour Guard Gated Resort Community! Beautiful Upscale Furnishings, Game Room, Tiled Roof, Granite Counter Tops, Stainless Steel Appliances, Tile Throughout, Screened Heated Pool And Spa With Covered Lanai And Much More. Amenities Within The Community Include: Clubhouse, Movie Theater, Game Room, Fitness Center, On-site Store, Snack Bar, Community Lagoo...

2595 Archfeld Blvd, Kissimmee

New Photo of Listing #O5796780

$419,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.19 Acres

Single Family / Villa

Windsor Hills

Located In "the Reserve" Of Windsor Hills, Backing Onto An Open Landscaped/treed Area Offering Pool/spa Privacy. This Well Maintained Home Has Not Been Rented During The Current Ownership. This Fully Furnished Vacation Home Offers Two Master Suites With 4 Other Bedrooms, With One Of The Bedrooms And Adjacent Bathroom Located On The First Floor, Colorful Key West Decor Painting Throughout, Upgraded Furnishings, Ceramic Tile In All Living Area's, Kitchen, And Bathrooms, Granite Kitchen Countertops, Upgraded Kitchen Cabinets, Ceiling Fans Throu...

2714 Manesty, Kissimmee

Photo of Listing #S5020564

$409,000

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 2,398.00 Acres

Single Family / Villa

Windsor Hills Ph 1-4 & 5...

This Is The One This Gorgeous Two Story Home With Its 6 Bedroom 4 Bath Is Waiting For You. With Its Private Pool You're Going To Enjoy The Florida Lifestyle Sit Back And Relax With All The Amenities That Come With This Gorgeous House A Definite Must-see To Appreciate. Centrally Located To All The Shopping Entertainment Restaurants And Of Course Disney All This House Needs Is A Family To Enjoy It .

7785 Basnett Cir, Kissimmee

Photo of Listing #S5013210

$398,500

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.14 Acres

Single Family / Villa

Windsor Hills Ph 03

Spacious 6 Bedroom With 2 Master Suites And 4 Full Bathrooms! **furnished!** Lovely Vacation Home In Windsor Hills Close To Disney And Major Theme Parks. Think About It You Can Live In The Home Full Time Or Rent Out To Vacationers. Folks Love Windsor Hills For The Location! The Community Is Guard Gated And Has Amenities Such As A Lagoon Style Pool With Hot Tub, Club House, Large Water Slides, Game Room, Movie Theater, Café, Fitness Center, Bar And Convenient Store, Tennis Courts, Volleyball Courts, Huge Playground, Putting Green And Barbecue...

2698 Manesty Ln, Kissimmee

New Photo of Listing #O5800026

$389,000

  • 5 Beds
  • 5 Baths

  • 2,297 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 03

New Roof July 2019, New Exterior Paint July 2019. West Facing Pool With Privacy. Neutral Colors Throughout This Well-maintained Home. Only 4.5 Miles To Disney’s Gate. This Home Offers One Of The Most Desirable Floor Plans In Windsor Hills With 5 Beds And 5 Baths, This Well- Kept Home Has A Private Back With No Rear Neighbors. It Is Walking Distance To Tennis Courts And The Clubhouse. Tastefully Decorated & Furnished With Neutral Colors Throughout And Offered As A Turnkey Property. Boasting 2 Master Suites With King Sized Beds On The First Fl...

7817 Beechfield St, Kissimmee

Price
Reduced
Photo of Listing #O5768274

$374,900

  • 6 Beds
  • 4 Baths

  • 2,812 SqFt
  • 0.15 Acres

Single Family / Villa

Windsor Hills Ph 05

Live-play-work Or Vaca In This Very Safe And Easy Community Close To Disney. Very Well Maintained Vacation Community With A "feels Like Home" Neighborhood. The Community Is Complete With -waterpark, Slides, Game Room, Fitness, Walking Trails And Small Grocery Store For Snacks And More. The Property Has A Resort Feel And This Bright Beauty Has Room To Accommodate The Whole Team, Family Or Group In A Spacious 6 Bedroom Fully Furnished And Super Well-maintained Property. From Tvs, Towels, Beach Balls, And More This Turn Key Property Is A High...

7827 Beechfield St, Kissimmee

Photo of Listing #S5019519

$359,000

  • 4 Beds
  • 4 Baths

  • 1,824 SqFt
  • 0.19 Acres

Single Family / Villa

Windsor Hills Ph 05

Just Listed - At The Time Of Listing, This Property Is Currently The One And Only 4 Bedroom Single Story Home Available For Sale On The Most Desirable, Gated Resort Of Windsor Hills Community. The Community Is One Of The Closest Locations To Disney And It Has Easy Access To Highway 192 & I4. This Unique Property Stands At What Is Almost The Summit Of This Beautiful Community And It Has Outstanding High Elevation Views To The North From The Rear Of The Property. Relax At Your Very Own Private Swimming Pool And Deck Area With No Rear Neighbors...

2640 Dinville St, Kissimmee

Photo of Listing #S5016564

$349,950

  • 6 Beds
  • 3 Baths
  • 1 Half

  • 2,469 SqFt
  • 0.16 Acres

Single Family / Villa

Windsor Hills Ph 03

Short Sale. This 6 Bedroom, 3 And Half Bathroom Home, Is Located In One Of The Finest Vacation Rental Communities Near Disney. Windsor Hills Is Located Just Minutes To The Disney Property And Features A Clubhouse, Pool With A Fabulous Slide And Hot Tub, Sundry Shop, 24-hour Guard Gated Community, Fountains, Movie Theater, Fitness Center, Games Room, Tennis, Basketball & Volleyball Courts, Putting Green, Barbecue Area, Giant Playground And Much More. This Home Is Sold Unfurnished. The Owner Is A Reservation Agent Is Willing To Continue To P...

7642 Sir Kaufmann Ct, Kissimmee

Photo of Listing #S5017688

$280,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 04

By Far This Home Is The Loaded With The Most Upgrades And Shows Like A Model. Granite Counter Tops In The Kitchen And The Bathrooms, Hard Wood Floors, Stainless Steele Appliances, Crown Molding, And So Much More!! Don’t Believe It….see It For Yourself. Very Attention To Detail And The Number Of Upgrades Are Countless. This Immaculate Townhome Is Graced With 3 Bedrooms, 3 Baths And A Sparkling Pool. This Exquisite 2 Story Home Has Everything To Offer In The Beautiful And Popular Community Of Winsor Hills. The Spacious Living Room Area Is Abs...

2516 Renshaw St, Kissimmee

Photo of Listing #O5795237

$269,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.04 Acres

Townhouse

Windsor Hills Ph 2

Immaculate Turn Key End Unit Townhome In The Popular Windsor Hills Vacation Community. Spacious Kitchen Features Plenty Of Cabinets, Breakfast Bar, And Opens To The Living/dining Combination. Carpet Was Replaced Mid 2018 With High Quality Option, The Washer And Dryer Were Also Replaced 2018 And Are High Efficiency. The Ac Unit Was Completely Replaced June 2018. The Furniture In This Home Is In Excellent Condition. Just A Short Walk To Windsor Hills Clubhouse Offering Movie Theater, Game Room, Fitness Center, Huge Heated Swimming Pool With...

7665 Fitzclarence St, Kissimmee

Photo of Listing #O5768250

$265,000

  • 3 Beds
  • 3 Baths

  • 1,440 SqFt
  • 0.03 Acres

Townhouse

Windsor Hills Ph 02

Located In The Sought-after Windsor Hills Gated Community. 2-story Townhome With Lake View And Private Pool. Beautifully Decorated 3-bedroom, 3 Bath Property With Living/dining Combo. Kitchen Has Breakfast Bar & Closet Pantry. One Bedroom Is Downstairs. Master Is Upstairs & Has Walk-in Closet. Screen Enclosed Pool With Paver Deck. This Property Is Very Close To The Clubhouse With Its Own Lagoon Style Pool And Brand New Waterpark, Gym, Tennis, Theatre And Far More!! Perfect As A Vacation Rental Or Second Home. Don’t Miss This One, All Yo...

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 July 21st, 2019 at 5:15pm EDT.