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 407-477-6586.

23 Results

Windsor Hills Kissimmee Florida Homes For Sale

Windsor Hills For Sale $710,000

Close up of front door featuring well-kept lawn, neat shrubs and a two-car garage at 7761 Tosteth St, Kissimmee, FL 34747
Cozy living room boasts tile flooring, a comfortable sectional sofa and stylish decor at 7761 Tosteth St, Kissimmee, FL 34747
Bright living room with a large sectional sofa, entertainment center, and open layout at 7761 Tosteth St, Kissimmee, FL 34747
On Market For 5 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2005

  • $/SqFt

    $252

This property is currently used for short-term rentals. EMPIRE NETWORK REALTY.

Windsor Hills For Sale $545,000

Aerial view of the house showcasing its location within a neighborhood with manicured lawns and mature trees at 7735 Teascone Blvd, Kissimmee, FL 34747
Neighborhood aerial view with house location pin, showcasing community layout and proximity to local amenities at 7735 Teascone Blvd, Kissimmee, FL 34747
Scenic aerial of the neighborhood's houses and street layout with nearby lake and water park at 7735 Teascone Blvd, Kissimmee, FL 34747
On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1878

  • Year Built

    2006

  • $/SqFt

    $290

Don’t miss this incredible investment and lifestyle opportunity—schedule your showing today! META ONE REALTY GROUP LLC.

Windsor Hills For Sale $639,000

Two-story home features a spacious two car garage and a manicured front lawn with mature tree at 2621 Archfeld Blvd, Kissimmee, FL 34747
Bright foyer features a console table with decorative artwork and offers a welcoming entrance at 2621 Archfeld Blvd, Kissimmee, FL 34747
Open-concept living area includes modern furnishings and seamless flow to the eat-in kitchen at 2621 Archfeld Blvd, Kissimmee, FL 34747
On Market For 10 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2297

  • Year Built

    2007

  • $/SqFt

    $278

Recent upgrades include new vinyl flooring (2022), a new AC unit on the second floor (2022), and a new pool pump (2024). RATIO REAL ESTATE, LLC.

Windsor Hills Pended $589,000

Aerial view showcasing the home's location near a lake and community amenities at 2641 Daulby St, Kissimmee, FL 34747
Welcoming entryway with stylish decor, storage, and tile flooring at 2641 Daulby St, Kissimmee, FL 34747
Stylish entryway featuring chic decor, storage, and a bright, airy ambiance at 2641 Daulby St, Kissimmee, FL 34747
On Market For 10 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1824

  • Year Built

    2005

  • $/SqFt

    $323

Don't miss your chance to own a piece of the magic—schedule your showing today! LA ROSA REALTY LLC.

Windsor Hills For Sale $455,000

View of townhouse showcasing blue exterior, individual parking spots, and tidy landscaping at 7671 Otterspool St, Kissimmee, FL 34747
Bright living room with sliding glass doors to the pool, neutral flooring, and comfortable seating at 7671 Otterspool St, Kissimmee, FL 34747
Open-concept living area with kitchen bar, modern lighting, and comfortable furnishings at 7671 Otterspool St, Kissimmee, FL 34747
On Market For 12 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2005

  • $/SqFt

    $316

Don't miss your chance to own a piece of the magic—schedule your showing today! LA ROSA REALTY LLC.

Windsor Hills For Sale $650,000

Bright and spacious entryway with tile floors and views to the living and dining areas at 2615 Pawnall St, Kissimmee, FL 34747
Living room with leather furniture, a large window and access to the pool area at 2615 Pawnall St, Kissimmee, FL 34747
Dining room with a large wood table and access to kitchen at 2615 Pawnall St, Kissimmee, FL 34747
On Market For 32 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2494

  • Year Built

    2007

  • $/SqFt

    $261

Don’t miss this incredible opportunity to own a home in one of the most sought-after vacation communities in Central Florida! THE PROPERTY FIRM.

Windsor Hills Pended $635,000

House in a residential neighborhood with a view of other homes and pools at 7733 Teascone Blvd, Kissimmee, FL 34747
Bright entryway with wood-look floors and a console table at 7733 Teascone Blvd, Kissimmee, FL 34747
Dining room with a glass-top table and modern chandelier at 7733 Teascone Blvd, Kissimmee, FL 34747
On Market For 27 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2297

  • Year Built

    2006

  • $/SqFt

    $276

Call today for a home Preview! PREFERRED REAL ESTATE.

Windsor Hills Pended $395,950

Two-story light blue townhome with landscaping and driveway at 2538 Renshaw St, Kissimmee, FL 34747
Private screened pool and patio area at 2538 Renshaw St, Kissimmee, FL 34747
Private screened pool and patio with access from sliding doors at 2538 Renshaw St, Kissimmee, FL 34747
On Market For 37 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 37 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 41 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 $640,000

Reduced By $10,000

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 41 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2009

  • $/SqFt

    $273

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 42 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 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 87 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 Pended $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 116 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 94 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 $655,000

Reduced By $5,000

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 112 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2008

  • $/SqFt

    $233

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 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 143 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 191 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 Pended $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 156 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 210 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 216 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 $595,000

Reduced By $20,000

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 305 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2005

  • $/SqFt

    $254

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 318 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.

  • 1

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 407-477-6586 and speak with one of our real estate consultants.

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