Osceola Homes with Gated Community Features

Osceola Homes with Gated Community Features

Welcome to Osceola County, Florida – a vibrant and diverse region that perfectly blends natural beauty with modern conveniences. Nestled in the heart of Central Florida, Osceola County is renowned for its picturesque landscapes, including lush wetlands, serene lakes, and an abundance of parks. This idyllic locale is not only home to the world-famous Walt Disney World Resort but also offers a rich tapestry of cultural experiences, recreational opportunities, and a warm sense of community.

For those seeking an elevated lifestyle, Osceola County boasts a selection of exquisite homes within gated communities. These exclusive neighborhoods provide a sanctuary of privacy and security, allowing residents to enjoy a tranquil living experience while being just moments away from the excitement of Orlando. With meticulously landscaped grounds, luxurious amenities, and a strong sense of community, these gated enclaves offer the perfect balance of comfort and sophistication.

Whether you’re looking for a spacious family home or a cozy retreat, the properties in Osceola’s gated communities cater to a variety of tastes and lifestyles. Residents can take advantage of resort-style amenities, including sparkling swimming pools, fitness centers, and clubhouse facilities, all while enjoying the peace of mind that comes with living in a secure environment.

Experience the charm of Osceola County, where every day feels like a vacation. Discover your dream home in one of our beautiful gated communities and embrace a lifestyle defined by luxury, comfort, and community spirit. Your perfect oasis awaits!

Newest Osceola Homes with Gated Community Features

$165,000
2 Beds ⋅ 1 Baths ⋅ B26074617 MLS
Well-maintained property located in the Michigan Court community in Saint Cloud, Florida. This unit features 2 bedrooms, 1 bathroom, and 856 square feet of living space. Recent updates include a new roof and new windows. The property is tenant-occupied with a lease in place through January 31, 2027, generating a monthly rent of $1,350. Conveniently located near major highways, shopping, dining, and entertainment options. An excellent option for buyers seeking a property with an active lease in place. Showings subject to tenant occupancy.

694 MICHIGAN Court Unit 1, St Cloud
$450,000
6 Beds ⋅ 5 Baths ⋅ B26071968 MLS
Beautifully maintained and fully furnished pool home located in the gated Trafalgar Village Resort community. This spacious home features 6 bedrooms and 5 bathrooms, offering a flexible floor plan ideal for families, multi-generational living, a second home, or a vacation property. The private, screened-in heated pool and spa provide the perfect outdoor retreat for relaxing and entertaining year-round, with a removable child safety fence for added peace of mind. Recent updates include a Refrigerator, Dishwash, Microwave, Wash and Dryer. All furnishings are included. Trafalgar Village Resort offers an exceptional array of resort-style amenities, including a clubhouse, fitness center, community pool with spa and beach area, basketball and sand volleyball courts, pickleball courts, playground, private movie theater, game room, fishing pier with BBQ area, and walking trails. The community features a secure gated entrance with 24-hour guard service. HOA fees include gated security, landscaping, pool maintenance, and daily trash service. Conveniently located near shopping, dining, major highways, Walt Disney World, and Central Florida's many attractions. A great opportunity to own a well-maintained, fully furnished home in a desirable resort community.

2642 MARG Lane, Kissimmee
$375,000
3 Beds ⋅ 3 Baths ⋅ B26064796 MLS ⋅ Margaritaville Dpr Construction BLDG.
**Charming 2-Bedroom Townhouse with Versatile Loft in The Margaritaville Community**.Step into this brand-new, fully furnished, upgraded 2-bedroom, 2.5-bath townhouse, featuring an upstairs bonus room area that can easily serve as a third bedroom. Perfectly positioned within the desirable Margaritaville Community, this property is currently operating as a successful Airbnb, with continuous bookings that provide an exceptional investment opportunity. Annual ROI details are available upon request. Designed for comfort and relaxation, this home offers a spacious open-concept living and dining area, a modern full kitchen, and spa-style bathrooms that make every day feel like a vacation. Enjoy your morning coffee/evening cocktail from your private outdoor terrace, surrounded by a lush scenery.

8174 Coconut Place, Kissimmee
$75,000
B26060146 MLS
3.75 acres in Holopaw with owner financing. Split it up and flip or keep it all for yourself.

Holopaw Groves Road, St Cloud
$490,900
5 Beds ⋅ 5 Baths ⋅ B26058583 MLS ⋅ Windsor At Westside BLDG.
This stunning 5-bedroom 4.5-bath townhouse is designed for both guests and owners: a full bedroom and bath downstairs, a private cabana bath, a spacious upstairs loft and thoughtful storage throughout. Neighbor privacy adds an extra layer of comfort rarely found in resort communities. Over $50K in design upgrades elevate the space, including a smart pool control system and noise monitoring for peace of mind. The property is fully turnkey with cleaning and pool teams already in place. This home is ready to go live from day one. Located in a true short-term rental community (28-day max stay, no residential mail), this is a rare opportunity to own in a zone built exclusively for vacation rental performance.

2431 Dubai Street, Kissimmee
$595,000
4 Beds ⋅ 4 Baths ⋅ B26053363 MLS
Welcome to this stunning 4-bedroom, 3-bathroom residence in Brighton Lakes Ph 1 Parcel C, Kissimmee. This two-story home boasts 3,387 square feet of finished living space, offering generous room for comfortable everyday living. The three-car garage provides convenient vehicle storage and additional space for your needs. Whether you're seeking a spacious residence with well-appointed rooms or appreciate the thoughtful layout of a single-family home, this property delivers on both counts. Located in the Brighton Lakes community, this home presents an excellent opportunity for those looking to establish their residence in​​‌​​​​‌​‌​​​​‌‌​​‌‌​‌‌​​‌​​​‌​‌ Kissimmee.

3607 Kariba Court, Kissimmee
$12,500
B26051426 MLS
Own in Holopaw! Camp, ride and hunt. Owner financing availble

Holopaw Groves Road, St Cloud
$12,500
B26051233 MLS

Holopaw Groves Road, St Cloud
$12,500
B26051228 MLS
camp, ride and hunt in Holopaw. Owner financing

Holopaw Groves Road, St Cloud
$12,500
B26051225 MLS
Holopaw campsite with owner financing. Camp, ride and hunt!

Holopaw Groves Road, St Cloud
$699,999
5 Beds ⋅ 5 Baths ⋅ B26047618 MLS ⋅ Sonoma Resort At Tapestry By Park Square BLDG.
MOTIVATED SELLER — ALL REASONABLE OFFERS WILL BE CONSIDERED! Welcome to 3870 Oakville Avenue, a turnkey, fully furnished resort home in the gated Sonoma Resort at Tapestry. Offering 5 bedrooms, 5 full bathrooms, and 3,067 square feet of living space, this property combines comfortable living with exceptional entertainment features. Enjoy a private home theater with two rows of reclining seats and ambient lighting. The garage is currently configured as a themed game room equipped with a pool table and air hockey, creating an additional space for fun and entertainment rather than vehicle parking. The open-concept living area features a contemporary fireplace wall and connects naturally to the kitchen, dining space, and outdoor living area. Two main-level bedrooms provide added convenience, while the remaining bedrooms offer privacy and flexibility for guests. Outside, enjoy a private screened pool and in-ground spa with covered patio space for relaxing after a day at the attractions. Furniture, décor, appliances, theater seating, and game-room equipment shown in the MLS photos are included. Owner occupancy and short-term rental use are permitted, subject to current HOA and governmental requirements. Conveniently located near Walt Disney World, Central Florida attractions, shopping, dining, and major roadways.

3870 Oakville Avenue, Kissimmee
$739,899
5 Beds ⋅ 5 Baths ⋅ B26047625 MLS ⋅ Park Square BLDG.
MOTIVATED SELLER — BRING YOUR OFFER! A generous 12,198-square-foot lot sets the stage for this fully furnished vacation home at 2676 Calistoga Avenue in gated Sonoma Resort at Tapestry. With approximately 0.28 acres, a private screened pool, and an in-ground spa, this property pairs a spacious setting with the convenience of resort living. Offering 5 bedrooms, 5 full bathrooms, and 3,067 square feet of living space, the home features themed bedrooms, an open living and dining area, and a kitchen island perfect for gathering. Two main-level bedrooms provide added flexibility, while an attached two-car garage adds convenience. Relax by the pool, unwind in the spa, or enjoy outdoor dining on the patio. All furniture, décor, and appliances shown in the MLS photos are included, making your transition to vacation-home ownership easier. Sonoma's community amenities include a clubhouse, fitness center, and resort-style pool, complemented by convenient access to Central Florida attractions, shopping, dining, and major roadways. Owner occupancy and short-term rentals are permitted subject to current HOA rules and applicable requirements. A spacious lot, a furnished retreat, and a motivated seller—schedule your showing and bring your offer!

2676 Calistoga Avenue, Kissimmee
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