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.

30 Results

Windsor Hills Kissimmee Florida Homes For Sale

Windsor Hills For Sale $405,000

Two-story townhome with light blue facade, dark shutters, and palm trees at 7666 Sir Kaufmann Ct, Kissimmee, FL 34747
Aerial view showcasing a property's roof, screened-in pools, and lush backyard at 7666 Sir Kaufmann Ct, Kissimmee, FL 34747
Bright foyer with tile flooring, staircase, and wall decor leading to the living spaces at 7666 Sir Kaufmann Ct, Kissimmee, FL 34747
On Market Today
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2005

  • $/SqFt

    $281

This turnkey property presents an excellent opportunity for vacation rental income or a personal Florida retreat! LUXE PROPERTIES LLC.

Windsor Hills For Sale $400,000

Charming townhome featuring light blue paint, and neatly trimmed landscaping at 2546 Maneshaw Ln, Kissimmee, FL 34747
Inviting townhome front entrance with blue door, lush shrubs, and covered entryway at 2546 Maneshaw Ln, Kissimmee, FL 34747
Bright, cozy kitchen with wood cabinets, tile floors, and eat-in bar area at 2546 Maneshaw Ln, Kissimmee, FL 34747
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2005

  • $/SqFt

    $278

Whether you're seeking a dream vacation home or a lucrative investment property, our home offers an unparalleled opportunity in the heart of Kissimmee's magic. Don't miss out! BEYCOME OF FLORIDA LLC.

Windsor Hills For Sale $439,999

A close-up view of the front door, showing its design and the surrounding exterior details of the home at 2537 Renshaw St, Kissimmee, FL 34747
A modern kitchen features stainless steel appliances, granite countertops, and dark cabinetry that enhances the space at 2537 Renshaw St, Kissimmee, FL 34747
A stylish kitchen with stainless steel appliances, granite countertops, and a sleek design at 2537 Renshaw St, Kissimmee, FL 34747
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2004

  • $/SqFt

    $306

Don't miss out—schedule your private showing today! STOCKWORTH REALTY GROUP.

Windsor Hills For Sale $639,900

Beautiful home featuring a two-car garage, well-manicured lawn, and mature trees enhancing curb appeal at 2631 Archfeld Blvd, Kissimmee, FL 34747
Inviting home exterior featuring a two-car garage, complemented by lush landscaping and a warm entryway at 2631 Archfeld Blvd, Kissimmee, FL 34747
Refreshing screened-in pool area with comfortable lounge chairs, perfect for relaxation and outdoor enjoyment at 2631 Archfeld Blvd, Kissimmee, FL 34747
On Market For 12 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2007

  • $/SqFt

    $273

All this and only 1 mile to HWY 192 for easy access to shopping, restaurants and I-4, and only just a few miles to all the theme parks.Don't miss out on this great income producing property!! ! NEXTHOME LOCATION.

Windsor Hills For Sale $400,000

Townhome featuring blue shutters, neutral paint, manicured landscaping, and driveway at 7682 Fitzclarence St, Kissimmee, FL 34747
Two-story townhome featuring a well-maintained front yard and ample parking at 7682 Fitzclarence St, Kissimmee, FL 34747
Community of townhomes with mature trees and sidewalks in a desirable location at 7682 Fitzclarence St, Kissimmee, FL 34747
On Market For 18 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2004

  • $/SqFt

    $278

The resort also has several playgrounds, tennis courts, a basketball court, a putting green, a BBQ area, and an oversized vehicle parking area. CENTURY 21 EDGE.

Windsor Hills For Sale $685,000

Stunning two-story home boasting a barrel tile roof, manicured landscaping, and a welcoming front entrance at 2508 Archfeld Blvd, Kissimmee, FL 34747
Bright living room showcasing tile floors, comfortable leather seating, staircase, and a media center at 2508 Archfeld Blvd, Kissimmee, FL 34747
Relaxing living room featuring a large window, leather seating, entertainment center, and neutral decor at 2508 Archfeld Blvd, Kissimmee, FL 34747
On Market For 19 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2008

  • $/SqFt

    $244

The well known and respected community of Windsor Hills has a great selection of facilities such as a fitness center, large community pool with a slide, water play area, tennis and basketball courts and more… Call today to arrange your private viewing. CGY REALTY.

Windsor Hills For Sale $670,000

Charming two-story house featuring a red tile roof, two-car garage and mature landscaping at 2548 Archfeld Blvd, Kissimmee, FL 34747
Close-up of the front door with decorative sidelights and a welcome mat at 2548 Archfeld Blvd, Kissimmee, FL 34747
Foyer entrance featuring a white door with sidelights and decorative curtains at 2548 Archfeld Blvd, Kissimmee, FL 34747
On Market For 19 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2010

  • $/SqFt

    $238

Windsor Hills is a beautiful resort with world-class amenities that offers: 24-Hour gated community security, water slides with splash pad and lagoon pool, gym, basketball and tennis courts, putting golf, community clubhouse, and on-site entertainment are just some of the reasons to choose this wonderful resort. LA ROSA REALTY LLC.

Windsor Hills For Sale $467,000

Modern living room featuring a stylish blue velvet sectional sofa at 7660 Otterspool St, Kissimmee, FL 34747
Open-concept living area with a kitchen island and comfortable seating at 7660 Otterspool St, Kissimmee, FL 34747
Spacious living room with a modern blue velvet sofa and bright, natural light at 7660 Otterspool St, Kissimmee, FL 34747
On Market For 25 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2005

  • $/SqFt

    $324

Currently used as a short term rental. EMPIRE NETWORK REALTY.

Windsor Hills For Sale $640,000

Relaxing screened-in pool area with a spa, lounge chairs, and covered patio, perfect for outdoor entertainment at 2683 Manesty Ln, Kissimmee, FL 34747
Bright kitchen with white cabinetry, modern appliances, and a cozy breakfast bar with seating at 2683 Manesty Ln, Kissimmee, FL 34747
Spacious living room featuring tile floors, a ceiling fan, and a comfortable sofa at 2683 Manesty Ln, Kissimmee, FL 34747
On Market For 26 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2297

  • Year Built

    2006

  • $/SqFt

    $279

With high demand for vacation rentals in this community, this home provides the perfect blend of relaxation and investment potential. GLOBAL REAL ESTATE SERVICES IN.

Windsor Hills Pended $624,999

Inviting home exterior featuring a well-maintained lawn, mature tree, and a two-car garage for convenience at 7759 Basnett Cir, Kissimmee, FL 34747
Enjoy the screened-in pool and spa area, perfect for relaxation and entertainment at 7759 Basnett Cir, Kissimmee, FL 34747
Aerial view of house with screened in pool in a neighborhood; your dream vacation home at 7759 Basnett Cir, Kissimmee, FL 34747
On Market For 27 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2005

  • $/SqFt

    $222

Brand-new flooring 2-year Roof Two Well Maintained AC units (Upstairs AC is only 2 years old) KELLER WILLIAMS REALTY SMART 1.

Windsor Hills For Sale $390,000

Aerial view of townhomes showcasing a well-maintained community with landscaping and ample parking at 7659 Sir Kaufmann Ct, Kissimmee, FL 34747
Wide aerial shot of a townhome community displaying well-kept landscaping, roofs, and ample parking at 7659 Sir Kaufmann Ct, Kissimmee, FL 34747
Community aerial showcasing rooflines, landscaping, and parking with cityscape views in the distance at 7659 Sir Kaufmann Ct, Kissimmee, FL 34747
On Market For 28 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2005

  • $/SqFt

    $271

Experience the magic of Central Florida in a home that truly has it all! TOP FLORIDA HOMES.

Windsor Hills For Sale $669,000

Aerial view of the property showing proximity to the Windsor Hills Clubhouse and Reedy Lake at 7709 Comrow St, Kissimmee, FL 34747
Aerial view shows the property's proximity to the community's basketball, tennis, and BBQ areas at 7709 Comrow St, Kissimmee, FL 34747
Bright foyer with high ceilings, colorful walls, wood-look flooring, and a staircase leading to the upper level at 7709 Comrow St, Kissimmee, FL 34747
On Market For 29 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2004

  • $/SqFt

    $286

Windsor Hills has everything you’re looking for in a resort with a superb location and world-class amenities including a lagoon-style community pool, water park, movie theater, bar, onsite convenience store, water slides, fitness center, game room, and much more. LA ROSA REALTY LLC.

Windsor Hills For Sale $462,000

Inviting open-concept living and dining area featuring modern decor, stylish furniture, and natural light at 7670 Otterspool St, Kissimmee, FL 34747
Open-concept living space with modern furniture, a large TV, and sleek finishes at 7670 Otterspool St, Kissimmee, FL 34747
Bright living room with comfortable seating, dining table, a large window with sheer curtains, and TV at 7670 Otterspool St, Kissimmee, FL 34747
On Market For 31 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    2005

  • $/SqFt

    $321

Act now and make it yours! Currently used for short-term rentals. EMPIRE NETWORK REALTY.

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 35 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 39 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 40 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 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 42 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 $649,999

Reduced By $1

Side view of a two-story home with a well-manicured lawn and a two-car garage at 2615 Pawnall St, Kissimmee, FL 34747
Inviting foyer featuring neutral tile floors, and a stylish wooden console table with decorative mirror at 2615 Pawnall St, Kissimmee, FL 34747
Spacious kitchen featuring stainless steel appliances, granite countertops, and ample cabinet space at 2615 Pawnall St, Kissimmee, FL 34747
On Market For 62 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 28 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 68 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 Pended $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 51 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 71 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 $629,999

Reduced By $20,001

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 70 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2342

  • Year Built

    2009

  • $/SqFt

    $269

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

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 117 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 $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 143 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 169 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 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 187 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 240 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 $745,000

Reduced By $24,900

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 239 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2812

  • Year Built

    2008

  • $/SqFt

    $265

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 335 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.

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