Below you can view all the homes for sale in the Windsor Hills subdivision located in Kissimmee Florida. Listings in Windsor Hills are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Windsor Hills, give us a call at 407-485-1814.

20 Results

Windsor Hills Kissimmee Florida Homes For Sale

Windsor Hills For Sale $395,950

View of a green backyard with a lush hedge and homes in the background at 2538 Renshaw St, Kissimmee, FL 34747
Private screened-in pool with a light-tan deck at 2538 Renshaw St, Kissimmee, FL 34747
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2004

  • $/SqFt

    $275

Don't miss out on this amazing opportunity to own a piece of paradise just minutes from Disney World. SELECT ESTATES, LLC.

Windsor Hills For Sale $424,900

Two-story light blue house with navy blue shutters and landscaped front yard at 2546 Renshaw St, Kissimmee, FL 34747
Two story house with driveway and landscaping, aerial view at 2546 Renshaw St, Kissimmee, FL 34747
Townhouses in a community setting with green space at 2546 Renshaw St, Kissimmee, FL 34747
On Market For 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2004

  • $/SqFt

    $295

Schedule your showing today and secure your place in Orlando’s most sought-after vacation community—before it’s gone! COMPASS FLORIDA, LLC.

Windsor Hills For Sale $750,000

Tan two-story house with a two-car garage and lush landscaping at 2715 Manesty Ln, Kissimmee, FL 34747
Open living room and dining area with tile floors and neutral colors at 2715 Manesty Ln, Kissimmee, FL 34747
Spacious living room with tile floors, neutral decor, and a view of the dining area at 2715 Manesty Ln, Kissimmee, FL 34747
On Market For 6 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2006

  • $/SqFt

    $267

This home has an excellent property management company in place to help with the continue rentals. TOP NATION REALTY ADVISORS.

Windsor Hills For Sale $650,000

Two-story house with beige exterior, double garage, and landscaping at 2549 Archfeld Blvd, Kissimmee, FL 34747
Bird's eye view of house with pool and surrounding homes at 2549 Archfeld Blvd, Kissimmee, FL 34747
Aerial view of residential neighborhood with similar houses at 2549 Archfeld Blvd, Kissimmee, FL 34747
On Market For 6 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2009

  • $/SqFt

    $278

Convenient location, easy access to major highway I4, US 27, and US 192. Give yourself a tour! ALLIANCE REAL ESTATE GROUP.

Windsor Hills Pended $705,000

Spacious living room with gray sofas, patterned rug, and large windows at 2659 Dinville St, Kissimmee, FL 34747
Modern kitchen featuring stainless steel appliances and granite countertops at 2659 Dinville St, Kissimmee, FL 34747
Eat-in kitchen with white cabinets, granite counters, and view to living area at 2659 Dinville St, Kissimmee, FL 34747
On Market For 7 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2006

  • $/SqFt

    $251

Conveniently located just 1 mile from HWY 192, this home provides easy access to shopping, dining, I-4, and all the nearby theme parks. LA ROSA REALTY LLC.

Windsor Hills Pended $384,000

Townhome community view showing location and pool at 2545 Renshaw St, Kissimmee, FL 34747
Galley kitchen with stainless steel appliances and dark cabinets at 2545 Renshaw St, Kissimmee, FL 34747
Kitchen features stainless steel appliances and wood cabinets at 2545 Renshaw St, Kissimmee, FL 34747
On Market For 44 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2004

  • $/SqFt

    $267

Schedule your showing today and make this Central Florida gem yours! LA ROSA REALTY LLC.

Windsor Hills For Sale $645,000

Bright and airy foyer with tile floors, stylish decor, and view to staircase and dining area at 7731 Comrow St, Kissimmee, FL 34747
Elegant staircase with dark wood railings leading to the upper level at 7731 Comrow St, Kissimmee, FL 34747
Spacious living room with white sectional sofa, large windows, and view of the pool at 7731 Comrow St, Kissimmee, FL 34747
On Market For 52 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    2342

  • Year Built

    2004

  • $/SqFt

    $275

Windsor Hills is considered the most popular private rental community in Orlando. CINO INTERNATIONAL INC.

Windsor Hills For Sale $599,950

Reduced By $9,550

Two-story house with a two-car garage and landscaped yard at 2619 Archfeld Blvd, Kissimmee, FL 34747
Front entry with a gray door and a bench at 2619 Archfeld Blvd, Kissimmee, FL 34747
Bright and spacious entryway with staircase at 2619 Archfeld Blvd, Kissimmee, FL 34747
On Market For 81 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2297

  • Year Built

    2007

  • $/SqFt

    $261

Don't miss out on this chance to own your slice of paradise! TEAM DONOVAN.

Windsor Hills Pended $779,000

Inviting, Mickey Mouse themed pool and spa at 2616 Daulby St, Kissimmee, FL 34746
Basement game room with pool table, arcade games, and Star Wars decor at 2616 Daulby St, Kissimmee, FL 34746
Two-story house with gray siding, two-car garage, and landscaping at 2616 Daulby St, Kissimmee, FL 34746
On Market For 59 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2005

  • $/SqFt

    $277

3D Matterport Video available https://my.matterport.com/show/?m=Ck37ovKqtUR&mls=1 NEXTHOME LOCATION.

Windsor Hills For Sale $668,000

Two-story house with tile roof, gray siding, and a two-car garage at 2615 Archfeld Blvd, Kissimmee, FL 34747
Two-story house with tile roof, gray siding, and a two-car garage at 2615 Archfeld Blvd, Kissimmee, FL 34747
Gray front door entrance with lush landscaping at 2615 Archfeld Blvd, Kissimmee, FL 34747
On Market For 78 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2008

  • $/SqFt

    $238

This home is perfect for those seeking a blend of style, comfort, and relaxation in a highly desirable neighborhood—ready to enjoy from day one, as it comes fully furnished. EXP REALTY LLC.

Windsor Hills Pended $409,999

Two-story townhome with light blue exterior, landscaping, and palm trees at 7655 Sir Kaufmann Ct, Kissimmee, FL 34747
Living room features leather couches, a coffee table, and access to a pool at 7655 Sir Kaufmann Ct, Kissimmee, FL 34747
Open living and kitchen area with a contemporary design at 7655 Sir Kaufmann Ct, Kissimmee, FL 34747
On Market For 96 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2005

  • $/SqFt

    $285

Currently in a short-term rental program, this home is turn-key for whatever you're looking to do! Schedule your showing today! EXP REALTY LLC.

Windsor Hills For Sale $629,500

Reduced By $10,000

Spacious living room with sectional sofa, large windows, and access to patio at 2616 Bowring St, Kissimmee, FL 34747
Inviting pool area with covered patio and lounge chairs at 2616 Bowring St, Kissimmee, FL 34747
Two-story house with a two-car garage and well-manicured lawn at 2616 Bowring St, Kissimmee, FL 34747
On Market For 107 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2007

  • $/SqFt

    $269

Future bookings can convey to new owner if desired. NEXTHOME LOCATION.

Windsor Hills For Sale $415,000

Reduced By $20,000

Evening view of light blue townhouses with palm trees and landscaped yards at 7663 Fitzclarence St, Kissimmee, FL 34747
Aerial view of light blue townhouses with palm trees and parking at 7663 Fitzclarence St, Kissimmee, FL 34747
Living room with dark leather couches, a coffee table, and tile floors at 7663 Fitzclarence St, Kissimmee, FL 34747
On Market For 156 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2005

  • $/SqFt

    $288

Schedule a tour today and take the first step toward making your vacation dreams a reality! CREEGAN GROUP.

Windsor Hills For Sale $639,950

Reduced By $35,050

Front entrance with two-car garage and landscaping at 7724 Comrow St, Kissimmee, FL 34747
Two-story house with two-car garage and landscaping at 7724 Comrow St, Kissimmee, FL 34747
Bright and spacious entryway with tile flooring at 7724 Comrow St, Kissimmee, FL 34747
On Market For 123 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2004

  • $/SqFt

    $273

5 bedrooms and 5 bathrooms Updated in 2023 New Roof 2024 HVAC in 2023 Private Pool & Spa Closed neighborhood to Disney property Gated Community Short Term Rental Revenue: 2023 Revenue 104k YTD 2024 $64,207, Same YTD 2023 $56,607. 11.8% increase in 2024 YTD. HOMECOIN.COM.

Windsor Hills For Sale $390,000

Relaxing pool area with pergola, lounge chairs, and umbrellas at 7663 Sir Kaufmann Ct, Kissimmee, FL 34747
Large resort-style pool with plenty of surrounding lounge chairs at 7663 Sir Kaufmann Ct, Kissimmee, FL 34747
Colorful waterpark with slides and splash features for  at 7663 Sir Kaufmann Ct, Kissimmee, FL 34747
On Market For 175 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2005

  • $/SqFt

    $271

Don’t miss this opportunity to own a piece of Central Florida’s vacation lifestyle. HOMECOIN.COM.

Windsor Hills For Sale $757,400

Reduced By $12,500

Peaceful location in the Windsor Hills Resort Community at 2609 Archfeld Blvd, Kissimmee, FL 34747
Southeast-facing heated pool and hot tub at 2609 Archfeld Blvd, Kissimmee, FL 34747
Star Wars themed bedroom with four built-in bunk beds at 2609 Archfeld Blvd, Kissimmee, FL 34747
On Market For 181 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2008

  • $/SqFt

    $269

Schedule you’re showing today before it's too late! REAL BROKER, LLC.

Windsor Hills For Sale $610,000

Reduced By $49,000

Two-story house with a two-car garage and manicured lawn at 2710 Manesty Ln, Kissimmee, FL 34747
Two-story house with a two-car garage and lush landscaping at 2710 Manesty Ln, Kissimmee, FL 34747
Two-car garage and front entry with lush landscaping at 2710 Manesty Ln, Kissimmee, FL 34747
On Market For 214 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2006

  • $/SqFt

    $260

With golf, restaurants, and grocery stores just a stone's throw away, experience the epitome of Florida living in this remarkable abode. REDFIN CORPORATION.

Windsor Hills For Sale $599,900

Reduced By $15,100

Two-story house with a two-car garage, surrounded by lush greenery at 7722 Teascone Blvd, Kissimmee, FL 34747
Two-story house with a two-car garage and a well-maintained yard at 7722 Teascone Blvd, Kissimmee, FL 34747
Bright kitchen with stainless steel appliances and light wood cabinets at 7722 Teascone Blvd, Kissimmee, FL 34747
On Market For 270 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2005

  • $/SqFt

    $256

Don't miss your chance to own a piece of paradise in Windsor Hills! GLOBAL REAL ESTATE SERVICES IN.

Windsor Hills For Sale $464,000

Reduced By $21,000

Bright entryway with stairs, bench, and artwork leading to kitchen at 2547 Renshaw St, Kissimmee, FL 34747
Modern kitchen with white cabinets, stainless steel appliances, and an island at 2547 Renshaw St, Kissimmee, FL 34747
Convenient coffee bar with Keurig, mugs, and ample counter space at 2547 Renshaw St, Kissimmee, FL 34747
On Market For 283 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2004

  • $/SqFt

    $322

Come see this one of a kind, incoming producing property! EXP REALTY LLC.

Windsor Hills For Sale $819,000

Living room with themed mural and staircase at 7822 Beechfield St, Kissimmee, FL 34747
Spacious living room with themed decor at 7822 Beechfield St, Kissimmee, FL 34747
Dining room with themed wall and kitchen view at 7822 Beechfield St, Kissimmee, FL 34747
On Market For 478 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2006

  • $/SqFt

    $350

• New HVAC units (2 for house, plus mini split) • New fully stocked kitchen cupboards, granite, faucet and stainless steel appliances • New LVT flooring on main and bathrooms & carpet in bedrooms and stairway • New bathroom vanities, granite, faucets, and toilets • New showers with barn doors in both master bathrooms • New basketball and iceball in arcade, with refurbished pool table, buck hunter & driving games • New wall mounted smart televisions in living room and all bedrooms (1-75", 2-65", 3-55") • New ceiling fans in all bedrooms • New furniture inside and out with protective glass furniture tops and new décor throughout • New pool alarms and new screens on entire enclosure • New linens and towels, ready for rent! SUNSHINE FLORIDA REALTY, INC.

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Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-485-1814 and speak with one of our real estate consultants.

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