Windsor Hills Resort Vacation Homes for Sale

2623 Pawnall Street, Kissimmee image
2623 Pawnall Street, Kissimmee $700,000 ▲

Busy rental: Next available to view is July 26! Minutes to Animal Kingdom! Guest friendly, fun, and full of upgrades! This vacation home has been thoughtfully improved w...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 6 SubDv.
  • 34747 Zip Code
7765 Tosteth Street, Kissimmee image
7765 Tosteth Street, Kissimmee $699,000

Welcome to 7765 Tosteth Street, a beautifully appointed vacation home in the heart of Windsor Hills Resort — Orlando's premier gated short-term rental community, just min...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 3 SubDv.
  • 34747 Zip Code
7805 Beechfield Street, Kissimmee image
7805 Beechfield Street, Kissimmee $695,000

Beautifully professionally decorated and totally renovated, this exceptional vacation home is truly turnkey and designed to impress both owners and guests alike. The spac...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 5 SubDv.
  • 34747 Zip Code
7788 Basnett Circle, Kissimmee image
7788 Basnett Circle, Kissimmee $649,000 ▼

Strong booking activity through the end of 2026!! Welcome to your ultimate vacation getaway—fully renovated in 2025 and featuring a brand-new roof (2025), all on a prime ...

  • 5 Beds
  • 5 Baths
  • Windsor Hills Ph 3 SubDv.
  • 34747 Zip Code
7759 Tosteth Street, Kissimmee image
7759 Tosteth Street, Kissimmee $630,000 ▼

Welcome to this beautifully maintained 6-bedroom, 4-bathroom fully furnished home located in the highly sought-after Windsor Hills Resort in Kissimmee. Designed for comfo...

  • 6 Beds
  • 4 Baths
  • Windsor Hills Ph 3 SubDv.
  • 34747 Zip Code
2648 Dinville Street, Kissimmee image
2648 Dinville Street, Kissimmee $625,000 ▼

Welcome to this beautifully updated beach-themed oasis, a fully renovated and furnished STR home located in the heart of Kissimmee. This property underwent a complete ...

  • 5 Beds
  • 5 Baths
  • Windsor Hills Ph 3 SubDv.
  • 34747 Zip Code
2648 Daulby Street, Kissimmee image
2648 Daulby Street, Kissimmee $615,000

Welcome to your dream Florida oasis at 2648 DAULBY ST, nestled in the highly sought-after, guard-gated Windsor Hills Resort. This fully furnished 6-bedroom, 3.5-bathroom ...

  • 6 Beds
  • 4 Baths
  • Windsor Hills SubDv.
  • 34747 Zip Code
7743 Comrow Street, Kissimmee image
7743 Comrow Street, Kissimmee $615,000

Welcome to this exceptional turnkey vacation rental opportunity in the highly sought-after Windsor Hills Resort! This fully furnished 4 bedroom, 4 bath home is designed t...

  • 4 Beds
  • 4 Baths
  • Windsor Hills Ph 1 SubDv.
  • 34747 Zip Code
Kissimmee image
Kissimmee $610,000

This beautifully maintained 5-bedroom, 5-bath home in the 5-Star Windsor Hills Resort is an income-producing short-term vacation rental located just minutes from Walt Dis...

  • 5 Beds
  • 5 Baths
  • Windsor Hills Ph 3 SubDv.
  • 34747 Zip Code
7755 Grassendale Street, Kissimmee image
7755 Grassendale Street, Kissimmee $599,900 ▼

Welcome to 7755 Grassendale Street! This TURNKEY, well-maintained 4-bedroom, 4-bath home is move-in ready and ideal as a primary residence or short-term vacation rental....

  • 4 Beds
  • 4 Baths
  • Windsor Hills Ph 6 SubDv.
  • 34747 Zip Code
2615 Pawnall Street, Kissimmee image
2615 Pawnall Street, Kissimmee $589,999 ▼

Highly Desirable Windsor Hills Subdivision – Just 4.5 Miles from Disney! Welcome to Windsor Hills, a premier guard-gated community built by Pulte, known for its luxury...

  • 5 Beds
  • 5 Baths
  • Windsor Hills Ph 06 SubDv.
  • 34747 Zip Code
7750 Teascone Boulevard, Kissimmee image
7750 Teascone Boulevard, Kissimmee $549,000 ▼

Here is your opportunity to own one of the small number of single story 4 bedroom 4 bathroom homes that were built in the gated resort of Windsor Hills. The turnkey home ...

  • 4 Beds
  • 4 Baths
  • Windsor Hills Ph 6 SubDv.
  • 34747 Zip Code
7739 Teascone Boulevard, Kissimmee image
7739 Teascone Boulevard, Kissimmee $540,000 ▼

LOCATION! LOCATION! Turnkey 4-Bed, 4-Bath Home in Windsor Hills Resort – Minutes from Disney! Step into this fully furnished, move-in ready home featuring 1,878 sq ft of...

  • 4 Beds
  • 4 Baths
  • Windsor Hills Ph 5 SubDv.
  • 34747 Zip Code
2500 Renshaw Street, Kissimmee image
2500 Renshaw Street, Kissimmee — 2500 $455,000

Turnkey Vacation Rental Investment in Windsor Hills Resort – Minutes from Disney World Exceptional opportunity to own a fully furnished, turnkey vacation rental in Win...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 2 SubDv.
  • 34747 Zip Code
7667 Otterspool Street, Kissimmee image
7667 Otterspool Street, Kissimmee — 7667 $449,000

Beautifully End-Unit Townhome in Windsor Hills! In a premier 24-hour guard-gated community! Perfect for year-round living, a vacation retreat, or a profitable short-term ...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 2 SubDv.
  • 34747 Zip Code
7674 Otterspool Street, Kissimmee image
7674 Otterspool Street, Kissimmee — 7674 $425,000

Welcome to this beautifully maintained and upgraded 3-bedroom, 3-bathroom pool townhome located in the highly sought-after Windsor Hills Resort, just minutes from Walt Di...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 2 SubDv.
  • 34747 Zip Code
7677 Fitzclarence Street, Kissimmee image
7677 Fitzclarence Street, Kissimmee $420,000

Welcome to 7677 Fitzclarence St, a beautifully maintained and fully furnished townhome located in the highly desirable, guard-gated community of Windsor Hills Resort just...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 2 SubDv.
  • 34747 Zip Code
2530 Maneshaw Lane, Kissimmee image
2530 Maneshaw Lane, Kissimmee — N/A $419,000

Welcome to Windsor Hills, one of Central Florida's premier resort-style gated communities, where comfort, convenience, and investment potential come together in this beau...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 4 SubDv.
  • 34747 Zip Code
2545 Renshaw Street, Kissimmee image
2545 Renshaw Street, Kissimmee — Na $419,000

ANOTHER EPIC LISTING!!! Welcome to this beautiful appointed 3 bedroom - 3 bath townhome in in beautiful Windsor Hills. This is your chance to own a vacation property with...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 2 SubDv.
  • 34747 Zip Code
7681 Sir Kaufmann Court, Kissimmee image
7681 Sir Kaufmann Court, Kissimmee — 7681 $410,000 ▼

Welcome to this beautifully maintained 3-bedroom, 3-bath end-unit townhome featuring a private splash pool, located in the highly desirable Windsor Hills Resort, a premie...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 4 SubDv.
  • 34747 Zip Code
7654 Otterspool Street, Kissimmee image
7654 Otterspool Street, Kissimmee — 7654 $409,000 ▼

SOUTH-FACING POOL! Welcome to a standout vacation home in the popular Windsor Hills Resort, just minutes from the magic of Disney! This beautifully furnished 3-bedroom, ...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 2 SubDv.
  • 34747 Zip Code
2556 Renshaw Street, Kissimmee image
2556 Renshaw Street, Kissimmee — Windsor Hills $405,000 ▼

NEW ROOF 2026 PRIVATE YARD VIEWS! Pool heater 2022,Very close to the waterpark! Welcome to your dream townhouse featuring three bedrooms and three bathrooms in a vibrant ...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 2 SubDv.
  • 34747 Zip Code
7683 Fitzclarence Street, Kissimmee image
7683 Fitzclarence Street, Kissimmee — 7683 $399,000

TURNKEY WINDSOR HILLS END-UNIT TOWNHOME! This beautifully furnished 3 bedroom, 3 bathroom vacation home is located in one of the most established short-term rental resort...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 02 SubDv.
  • 34747 Zip Code
2534 Maneshaw Lane, Kissimmee image
2534 Maneshaw Lane, Kissimmee — 2534 $394,000 ▼

Prime Location! Just minutes from Central Florida’s top attractions, with easy access to shopping, restaurants, entertainment, and local theme parks. Enjoy resort-style a...

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 4 SubDv.
  • 34747 Zip Code
7663 Sir Kaufmann Court, Kissimmee image
7663 Sir Kaufmann Court, Kissimmee — - $380,000 ▼

Beautiful community Windsor Hills, located only 2 miles from Disney, tons of amenities, private screened heated splash pool!

  • 3 Beds
  • 3 Baths
  • Windsor Hills Ph 4 SubDv.
  • 34747 Zip Code
2774 Almaton Loop Unit 105, Kissimmee image
2774 Almaton Loop Unit 105, Kissimmee — 2774 $379,500 ▼

This stunning turnkey short term rental is fully furnished, beautifully themed, and ready to enjoy from day one. Located in the highly sought after Windsor Hills Resort,...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 3 SubDv.
  • 34747 Zip Code
2778 Almaton Loop Unit 303, Kissimmee image
2778 Almaton Loop Unit 303, Kissimmee — 2778 $350,000

Welcome to an exceptional opportunity in the highly sought-after Windsor Hills Resort, one of Central Florida's premier vacation destinations. Perfectly positioned just m...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 3 SubDv.
  • 34747 Zip Code
2821 Almaton Loop Unit 203, Kissimmee image
2821 Almaton Loop Unit 203, Kissimmee — 2821 $349,900

Welcome to your dream vacation retreat or high-performing investment property at 2821 Almaton Loop, Unit 203. Just a few steps from the Club House and Pool area. This met...

  • 3 Beds
  • 2 Baths
  • Windsor Hills, Ventura At Windsor Hills SubDv.
  • 34747 Zip Code
2821 E Almaton Loop Unit 401, Kissimmee image
2821 E Almaton Loop Unit 401, Kissimmee — Building 2821 $345,000

Experience resort-style living in this beautiful furnished 3-bedroom, 2 bathroom top-floor corner condo located at Windsor Hills, just minutes from Wall Disney World. Th...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 6 SubDv.
  • 34747 Zip Code
2813 Almaton Loop Unit 301, Kissimmee image
2813 Almaton Loop Unit 301, Kissimmee — 2813 $340,000

Well-maintained 3-bedroom, 2-bath condo located in the desirable Windsor Hills Resort. This unit features an open-concept living and dining area with a functional layout ...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 4 SubDv.
  • 34747 Zip Code
2821 Almaton Loop Unit 301, Kissimmee image
2821 Almaton Loop Unit 301, Kissimmee — 2821 $340,000 ▼

Beautifully renovated 3 bedroom, 2 bath condo located in the highly desirable Windsor Hills Resort, just 2.5 miles from Walt Disney World. This spacious vacation home is ...

  • 3 Beds
  • 2 Baths
  • Ventura Windsor Hls P6 SubDv.
  • 34747 Zip Code
7675 Comrow Street Unit 405, Kissimmee image
7675 Comrow Street Unit 405, Kissimmee — 7675 $339,000

Top-floor 3BR/2BA condo located in the highly sought-after Windsor Hills Resort—just minutes from Walt Disney World. This well-maintained property features ceramic tile t...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 5 SubDv.
  • 34747 Zip Code
2778 Almaton Loop Unit 203, Kissimmee image
2778 Almaton Loop Unit 203, Kissimmee — 3 $329,900 ▼

Welcome to 2778 Almaton Loop #203 – a beautifully updated 3-bedroom, 2-bathroom condo located in the sought-after gated community of Windsor Hills in Kissimmee. This turn...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 3 SubDv.
  • 34747 Zip Code
7664 Comrow Street Unit 204, Kissimmee image
7664 Comrow Street Unit 204, Kissimmee — 7664 $329,000

Windsor Hills Resort! One of best resort Minutes to Disney, Fully Furnished and updated 3bed 2bath, quiet, gorgeous and space, Located just a few steps to Clubhouse with ...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 7 SubDv.
  • 34747 Zip Code
2821 Almaton Loop Unit 205, Kissimmee image
2821 Almaton Loop Unit 205, Kissimmee — 2821 $329,000

Windsor Hills Resort! One of best resort Minutes to Disney, Fully Furnished and updated 3bed 2bath, quiet, gorgeous and space, Located just a few steps to Clubhouse with ...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 6 SubDv.
  • 34747 Zip Code
2817 Almaton Loop Unit 304, Kissimmee image
2817 Almaton Loop Unit 304, Kissimmee — 2817 $328,000 ▼

A beautiful 3-bedroom, 2-bathroom condo located in the highly sought-after gated community of Windsor Hills Resort in Kissimmee. This turnkey property is not only a fanta...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 6 SubDv.
  • 34747 Zip Code
2788 Almaton Loop Unit 404, Kissimmee image
2788 Almaton Loop Unit 404, Kissimmee — 2788 $325,000

Experience the best of Central Florida living in this beautifully maintained and fully furnished 3-bedroom, 2-bath condominium located within the highly sought-after Wind...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 1 SubDv.
  • 34747 Zip Code
7664 Comrow Street Unit 101, Kissimmee image
7664 Comrow Street Unit 101, Kissimmee — 7664 $319,000 ▼

SHORT WALK TO WINDSOR HILLS CLUBHOUSE, POOL, & WATERPARK! Ground Level!! This amazing 3 bedroom 2 bathroom ground-level condo is sold fully furnished and zoned for short-...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 7 SubDv.
  • 34747 Zip Code
2784 Almaton Loop Unit 301, Kissimmee image
2784 Almaton Loop Unit 301, Kissimmee $308,000 ▲

Mins to Disney! Magical 3BR + FREE Waterpark | 200Mbps WiFi | Elevator Access | Walk to Pool The Experience Step into your family’s fairytale! Our beautifully updated 3BR...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 1 SubDv.
  • 34747 Zip Code
7664 Comrow Street Unit 304, Kissimmee image
7664 Comrow Street Unit 304, Kissimmee — 7 $305,000 ▼

MOTIVATED SELLER! HUGE PRICE REDUCTION FOR A QUICK SALE! Don't miss this incredible opportunity to own a proven, income-producing vacation home in the highly sought-after...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo SubDv.
  • 34747 Zip Code
7671 Comrow Street Unit 202, Kissimmee image
7671 Comrow Street Unit 202, Kissimmee — 7671 $289,950 ▼

Step into a world of luxury and convenience with this beautifully fully furnished 2nd-floor condo at 7671 Comrow Street Unit 202 in the highly desirable Windsor Hills Res...

  • 2 Beds
  • 2 Baths
  • Windsor Hills, Ventura At Windsor Hills SubDv.
  • 34747 Zip Code
2781 Almaton Loop Unit 401, Kissimmee image
2781 Almaton Loop Unit 401, Kissimmee — 2781 $289,500 ▼

Priced to sell! This beautifully maintained 3-bedroom, 2-bathroom top-floor condo is offered fully furnished and zoned for short-term rental, making it an ideal investmen...

  • 3 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 2 SubDv.
  • 34747 Zip Code
7671 Comrow Street Unit 302, Kissimmee image
7671 Comrow Street Unit 302, Kissimmee — 7675 $288,000

Windsor Hills Resort! One of best resort Minutes to Disney, Fully Furnished and updated 2bed 2bath, quiet, gorgeous and space, Located just a few steps to Clubhouse with ...

  • 2 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 5 SubDv.
  • 34747 Zip Code
2788 Almaton Loop Unit 202, Kissimmee image
2788 Almaton Loop Unit 202, Kissimmee — Ventura $275,000

Located in the beautiful resort community of Windsor Hills just minutes from Disney. This spacious 2-bedroom, 2-bathroom condo comes fully furnished and is currently bein...

  • 2 Beds
  • 2 Baths
  • Windsor Hills P1 SubDv.
  • 34747 Zip Code
7675 Comrow Street Unit 402, Kissimmee image
7675 Comrow Street Unit 402, Kissimmee — Building 5 $249,900 ▼

Motivated seller who will consider reasonable offers upon showing! This open-palette, Windsor Hills Resort top-floor condo offers exceptional privacy on all sides with co...

  • 2 Beds
  • 2 Baths
  • Ventura At Windsor Hills Condo Ph 5 SubDv.
  • 34747 Zip Code

Windsor Hills Resort - West Hwy 192

Orlando Vacation Homes › West Hwy 192 Resort Area › Windsor Hills Resort

Owning a Vacation Home at Windsor Hills Resort

Windsor Hills Resort near Disney WorldWindsor Hills Resort is a gated resort of Single/Multi Family Homes and Townhomes in the West Hwy 192 Resort Area of Orlando. Windsor Hills is an older but still extremely popular resort loaded with amenities, home style options and in a fantastic location near Disney.

Whether it is the 80 foot water slide or the arcade loaded with modern and classic games, every guest is sure to find an amusement to entertain them at Windsor Hills.

Located just off Hwy, 192, Walt Disney World is just a couple of miles away, and you have plenty of dining, shopping and entertainment options in any direction you go from the resort.

Where is Windsor Hills Resort?

Windsor Hills Resort is located off N Old Lake Wilson Road in the West Hwy 192 resort area near Disney World.

The resort is South of Hwy 192 and East of the 429 Expressway and is found in the 34747 zip code in Osceola County.

How Far from Windsor Hills Resort to...

Windsor Hills Resort Owner Usage & Property Management

Windsor Hills Resort ClubhouseWindsor Hills Resort owners my use their property up to 365 days per year if they so choose. Owners may also rent their unit out for any length of time when not in use to generate income and/or to cover part or all of the owner fees.

There is on site property management at Windsor Hills Resort. Owners may use 3rd Party rental management or self manage. to handle to reservations and management of their unit at Windsor Hills Resort.

Windsor Hills Resort AmenitiesWindsor Hills Resort Amenities

The resort clubhouse features a movie theater, state of the art gym, huge game room with billiards and video games, sundries shop and tiki bar & grill. The clubhouse pool area features a large, palm tree shaded, beach entry pool, separate splash zone area with two water slides. There is also a hot tub and arbors and umbrellas for shading.

In a separate area of the resort there is a sportsplex area with sand volleyball court, tennis courts, basketball court and golf putting green.

Windsor Hills Resort Amenities in Orlando near Disney

Windsor Hills Resort Amenities include:

  • Resort Clubhouse Area with Fitness Center
  • Game Room
  • Movie Theater
  • Restaurant
  • Bar
  • Waterpark Pool Area with Slides
  • Spa/Hot Tubs
  • Tennis
  • Basketball
  • Sand Volleyball Courts

Vacation Homes Available in Windsor Hills Resort

Windsor Hills Resort Homes for SaleThe majority of the homes in Windsor Hills Resort were built 2005-2008 by Pulte Homes. There are 3 to 6 bedrooms, a similar number of bathrooms, and between 1246 to 2800 square feet of living space in each of the houses.

Vacation home options at Windsor Hills include 2 or 3 bedroom condos, 3 bedroom townhomes or 4 to 6 bedroom villa homes.

The townhomes and condos feature full kitchens and family room/dining room combos as well a laundry closed with washer and dryer.

The homes offer the same options as the townhomes and condos but with more space. Many of the homes come with private swimming pools. Owners may decorate their properties any way they see fit. There is no restriction on interior decor.

Windsor Hills Resort Homes

Typical Windsor Hills Resort Home Features Include:

  • Architectural Style(s): Spanish/Mediterranean, Contemporary and Florida
  • Number of Bedrooms: 3 to 6
  • Garage Spaces: 0 to 2
  • Approx Sq Ft under AC: 1246 to 2800
  • Interior Rooms: Family Room, Inside Utility
  • Construction Material: Block, Brick, Stucco and Wood Frame
  • Roof: Shingle and Tile

Windsor Hills Resort Video Tour Courtesy of Global Vacation Rentals

Call Us Now at 407-801-3286 and schedule your viewing of vacation homes for sale in Windsor Hills Resort today!

Photo Credit: Above images by Reunion Vacation Homes.

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Realtor David MyersDavid Myers 407-801-3286
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