Osceola Homes with Gated Community - Guard Community Features

Osceola Homes with Gated Community - Guard Community Features

Welcome to Osceola County, Florida, a vibrant region known for its stunning landscapes, rich culture, and family-friendly atmosphere. Nestled in the heart of Central Florida, Osceola County offers a unique blend of urban conveniences and natural beauty. From the bustling streets of Kissimmee to the serene shores of Lake Tohopekaliga, this county is a haven for outdoor enthusiasts, families, and retirees alike.

One of the standout features of Osceola County is its exceptional gated communities, offering residents the perfect balance of security and luxury. Imagine living in a beautifully designed home within a guard-gated community, where peace of mind and privacy are paramount. These exclusive neighborhoods are not just about safety; they provide an array of amenities designed to enhance your lifestyle. Enjoy resort-style pools, state-of-the-art fitness centers, and beautifully landscaped parks, all within steps of your front door.

Families will appreciate the top-rated schools and recreational facilities, while nature lovers can explore the nearby parks and lakes, perfect for fishing, hiking, and enjoying Florida's sunny weather. The proximity to major attractions like Walt Disney World and Universal Studios makes Osceola County an ideal location for both residents and investors seeking a vibrant community.

Whether you’re looking for a cozy single-family home or an elegant estate, Osceola County's gated communities offer a range of options that cater to diverse lifestyles. Experience the charm of this enchanting region and discover why so many choose to call Osceola County home!

Newest Osceola Homes with Gated Community - Guard Community Features

$525,000
4 Beds ⋅ 3 Baths ⋅ Tapestry Ph 2 SubDv. ⋅ 34741 Zip Code
Welcome to this beautifully upgraded corner-lot home in the highly sought-after 24-hour guard-gated community of Tapestry! This spacious two-story residence features 4 bedrooms, 2.5 bathrooms, plus a versatile bonus room on the first floor—ideal as a home office, gym, playroom, or guest space. All four bedrooms are privately located upstairs, creating the perfect separation between living and sleeping areas. The open-concept layout is filled with natural light and showcases elegant porcelain tile throughout the entire first floor. The modern kitchen overlooks the spacious living and dining areas, making it perfect for entertaining family and friends. Additional upgrades include a luxurious marble epoxy-coated garage floor, irrigation system, beautiful landscaping, and a partially fenced backyard. Step outside to enjoy the covered, screened lanai, perfect for relaxing year-round while overlooking the spacious corner lot. With plenty of room for children to play, pets to roam, or hosting weekend barbecues and family gatherings, the outdoor space is just as inviting as the interior. Residents enjoy resort-style amenities including a 24-hour guard-gated entrance, elegant clubhouse, state-of-the-art fitness center, resort-style lakefront pool, playgrounds, scenic walking trails, and beautiful lakes and green spaces throughout the community. Ideally located near The Loop, Orlando International Airport, major highways, shopping, dining, medical facilities, and world-famous attractions, this move-in-ready home offers the perfect combination of luxury, comfort, and convenience.

2527 Nouveau Way, Kissimmee
$469,900
3 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 6 SubDv. ⋅ 34747 Zip Code
GORGEOUS 'ONCE UPON A LIME' 3 Bed 3 Bath COTTAGE with Additional Bonus Room at Margaritaville Resort Orlando! This AMAZING Two-Floor Home features an Open Concept Living and Dining Room with Ceiling Fan, a Kitchen with QUARTZ Countertops, Stainless Steel Appliances, Side By-Side Washer and Dryer and Abundant Natural Light. Each of the Three Bedrooms and Living Room has Ceiling Fans, One Bathroom has a Shower/Tub Combo. The Door from the Kitchen Leads you to a Beautiful Patio with Lounge Chairs and Gorgeous Landscaping, Palm Trees and Tropical Foliage. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES Furniture/Housewares Package with Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

8061 Lost Shaker Lane, Kissimmee
$654,900
7 Beds ⋅ 6 Baths ⋅ Emerald Island Resort Ph 4 SubDv. ⋅ 34747 Zip Code
Turnkey short-term rental home, minutes to Disney! Discover a rare opportunity to own this stunning 7 bedroom, 6 bathroom pool home in the sought after Emerald Island Resort. Boasting the largest layout in the community at 3,667 sq. ft., this home is perfectly suited as a vacation getaway, income-generating investment, or forever family home. Enjoy unparalleled waterfront views framed by lush wooded backdrops, creating a serene and private retreat. The expansive screened lanai, which spans the length of the house, features a partially covered area ideal for year round entertaining. Relax by the sparkling South facing private pool and spa and take in the ultimate Florida lifestyle. Step inside to find a well designed floor plan with ample living space, ideal for families or hosting guests. The stylish kitchen is a chef’s dream with abundant cabinet and countertop space, a breakfast bar, and a breakfast nook overlooking the huge living room and pool, your new favorite spot for morning coffee or casual dining. The main floor also features two bedrooms, a formal dining room and the charming “Harry Potter” closet for extra fun and storage. The upper level is thoughtfully divided by two staircases. One leads to a loft sitting area and three themed bedrooms and the other leads to two additional themed bedrooms, all designed for comfort, as five of the bedrooms feature en-suite bathrooms, while the remaining two share a convenient Jack and Jill bath. The 3 car garage has been transformed into an entertainment haven with air conditioning, complete with a mini movie theatre (seating for 8) and a game room with a pool table. Updates include: A brand new roof (11/24), a new pool heater (04/24), newer exterior paint (01/22) and a newer A/C and heat pump (11/20), replumbed A/C lines (2024) and spa actuators replaced (2024). As part of this premier gated community, you’ll enjoy access to an impressive clubhouse with a resort-style pool, Tiki bar, fitness center, sauna, and sundry shop. Other amenities include tennis and pickleball courts, volleyball, basketball, bike rentals, and 11 acres of natural walking trails. The prime location is conveniently located near Orlando’s major attractions, including theme parks, outlet shopping, restaurants, Promenade at Sunset Walk, and Island H2O Live! water park. This home comes fully furnished and equipped with a strong rental history, ready to generate income as a short term rental or provide your family with a wonderful retreat. Schedule your tour today and experience the ultimate Florida lifestyle in this stunning property.

8557 La Isla Drive, Kissimmee
$455,000
3 Beds ⋅ 2 Baths ⋅ Del Webb Sunbridge Ph 2a SubDv. ⋅ 34771 Zip Code
Why wait to build when this like-new waterfront Hallmark home in Del Webb Sunbridge already offers panoramic pond views, completed upgrades and an exceptional move-in-ready Florida lifestyle? Located in St. Cloud’s premier gated 55+ active-adult community, this beautifully maintained, single-story home features the highly desirable HALLMARK FLOOR PLAN—NO LONGER OFFERED FOR NEW CONSTRUCTION in Del Webb Sunbridge. Built in 2023, it offers approximately 1,650 square feet with three bedrooms, two full bathrooms and a two-car garage—giving buyers the benefits of newer construction without the wait or added expense of completing major improvements after closing. The light-filled, open-concept floor plan seamlessly connects the kitchen, dining and gathering areas for comfortable everyday living and entertaining. The kitchen features quartz countertops, stainless-steel appliances, a natural-gas cooktop, built in oven and microwaves, pull-out cabinetry and a custom pantry with built-in shelving. Tile flooring flows throughout the entire home with no carpet, while a custom credenza and tinted-glass front door add style and functionality. Privately positioned at the rear of the home, the primary suite enjoys peaceful water views, a custom-designed walk-in closet and an upgraded walk-in shower with a built-in bench. Two secondary bedrooms are thoughtfully located away from the primary suite near the second full bathroom, creating excellent privacy and flexibility for overnight guests, hobbies or a home office. The true showpiece is the OVERSIZED SCREENED LANAI with an extended paver patio and PANORAMIC WATER VIEWS. Already PRE-PLUMBED FOR A FUTURE SUMMER KITCHEN, this exceptional outdoor living space is ready for sunset cocktails, relaxed mornings and year-round entertaining. Additional upgrades include a spacious laundry room with added cabinetry, generous storage and a utility sink; a salt-free water-softening system; natural gas servicing the tankless water heater and dryer; an epoxy-coated garage floor; and an insulated garage door. DEL WEBB SUNBRIDGE IS A GATED 55+ ACTIVE-ADULT COMMUNITY centered around the 27,000-square-foot Hammock Club, offering resort-style pools, a heated spa, fitness center, pickleball and tennis courts, walking trails, dog park, Tavern & Grille, resident clubs and a full social calendar. All outdoor yard maintenance and internet service are included for a convenient, low-maintenance lifestyle. Ideally located near Lake Nona, Orlando International Airport, Brightline and routes to Port Canaveral, this is the perfect lock-and-leave home base for enjoying Florida, traveling and staying close to family.

2499 Cliff Way, St Cloud
$929,000
7 Beds ⋅ 6 Baths ⋅ Sonoma Resort At Tapestry Ph 1 SubDv. ⋅ 34741 Zip Code
INVESTMENT & VACATION HOME OPPORTUNITY in the heart of Kissimmee! Welcome to 3841 Sonoma Blvd, an exceptional property offering the ideal combination of location, versatility, and income-producing potential in one of Central Florida’s most popular vacation destinations. Whether you’re looking to expand your investment portfolio, own a vacation rental near the theme parks, or enjoy your own Florida getaway while renting it when not in use, this property is ready to impress. The home features several customized upgrades that enhance its style, comfort, and appeal, creating an inviting retreat for both owners and vacation guests. Designed with the Orlando vacation lifestyle in mind, the property offers plenty of space to relax, entertain, and recharge after a day enjoying Central Florida’s world-famous attractions. LOCATION is a major advantage! Conveniently situated near Walt Disney World, Universal Orlando, shopping, dining, entertainment, golf, and major roadways, the property provides easy access to everything that makes the Orlando/Kissimmee area one of the most visited vacation destinations in the world. For investors, this is an opportunity to own a property in a highly recognized vacation market with strong appeal to both domestic and international travelers. For second-home buyers, enjoy your own Central Florida retreat with the added flexibility and potential of vacation-rental use. Beautifully located, upgraded, and positioned for the vacation-home market, 3841 Sonoma Blvd offers the combination investors and vacation-home buyers are looking for. Don’t miss the opportunity to add this exceptional Kissimmee property to your portfolio. Schedule your private showing today!

3841 Sonoma Boulevard, Kissimmee
$690,000
8 Beds ⋅ 6 Baths ⋅ Bellavida Resort SubDv. ⋅ 34746 Zip Code
Unlock the ultimate Florida vacation lifestyle and high-yield investment potential at 302 Marcello Blvd, a premier turn-key property nestled in the highly sought-after BellaVida Resort! This expansive, fully furnished 8-bedroom, 6-bathroom luxury residence is custom-built for epic group getaways and maximum rental performance. Step into sleek, open-concept living spaces designed to host grand gatherings, complete with a fully equipped kitchen and vast dining quarters. Step out back to your private tropical oasis featuring a pristine screened-in pool and sun-drenched patio, or head inside to the custom garage-turned-game room for non-stop, indoor entertainment. Beyond the home's incredible features, owners and guests enjoy full VIP access to BellaVida’s 24-hour gated, world-class resort amenities. The expansive 6,700-square-foot clubhouse boasts a zero-entry pool, relaxing hot tub, modern fitness center, sand volleyball, basketball courts, and scenic lakeside walking trails. Located just minutes from Walt Disney World, Universal Studios, top-tier golf, dining, and premier shopping along US-192, this income-generating powerhouse delivers unmatched location, luxury, and booking appeal for ambitious vacation home buyers and investors.

302 Marcello Boulevard, Kissimmee
$227,000
3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 6 SubDv. ⋅ 34747 Zip Code
Short Sale. SHORT-SALE OPPORTUNITY IN WINDSOR PALMS! This fully furnished 3-bedroom, 2-bath condo offers approximately 1,268 square feet in a gated resort community just minutes from Walt Disney World. Suitable for personal occupancy, a vacation home, or short- or long-term rental use, subject to applicable association rules, licensing, and governmental requirements. Documented 2023 updates include the A/C system, luxury vinyl flooring, interior paint, granite countertops, bathroom vanities and sinks, kitchen sink, dishwasher, and washer/dryer. Televisions were updated in 2025. Community amenities include gated entry, resort-style pool, clubhouse, sports courts, movie theater, arcade, and bar. Conveniently located near Disney-area attractions, shopping, dining, entertainment, major roadways, and Orlando-area airports. Sale price, terms, and closing timeline require the seller’s lender approval. Buyer must verify measurements, property condition, included furnishings, HOA fees and assessments, rental requirements, licensing, insurance, financing, and association information.

8107 Coconut Palm Way Unit 201, Kissimmee
$495,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully maintained 5-bedroom, 4.5-bathroom home located in the highly sought-after Windsor at Westside Resort in Kissimmee. Whether you're searching for a primary residence, vacation home, or investment property, this home offers the perfect blend of comfort, style, and convenience. The spacious open-concept floor plan features a modern kitchen with granite countertops, stainless steel appliances, and a large island overlooking the living and dining areas. The first-floor primary suite provides privacy and convenience, while the additional bedrooms plenty of space for family and guests. Step outside to your private screened-in pool, perfect for relaxing after a day at the theme parks. Residents and guests enjoy access to resort-style amenities including a clubhouse, fitness center, resort pool, lazy river, waterslide, sports courts, playground, and 24-hour gated security. Ideally located just minutes from Walt Disney World, shopping, dining, golf courses, and major highways, this property offers exceptional convenience for both homeowners and vacation guests. Don't miss this opportunity to own a home in one of Central Florida's premier resort communities.

2417 Dubai Street, Kissimmee
$314,900
3 Beds ⋅ 2 Baths ⋅ Remington Prcl K Ph 3 SubDv. ⋅ 34744 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the desirable gated community of Remington in Kissimmee. Offering approximately 1,560 square feet of comfortable living space, this move-in-ready residence features a bright, open floor plan with a spacious living and dining area, a well-appointed kitchen with ample cabinet and counter space, and a split-bedroom layout that provides added privacy. The primary suite includes a walk-in closet and an en-suite bathroom. Two additional bedrooms and a full guest bath provide plenty of space for family, guests, or a home office. Enjoy Florida living year-round from the rear patio overlooking the backyard—perfect for relaxing or entertaining. Remington residents enjoy access to outstanding community amenities, including a championship golf course, clubhouse, swimming pool, tennis courts, basketball courts, playgrounds, walking trails, and beautifully maintained common areas. Conveniently located near major highways, Lake Nona Medical City, Orlando International Airport, shopping, dining, schools, and world-famous attractions, this home offers the perfect combination of comfort, convenience, and lifestyle. Sold AS-IS. Seller is a corporation and has never occupied the home. Seller does not disclose. It is Buyer and Buyers brokers responsibility to verify all information, HOA fees, restrictions and approval process. Seller chooses Mainstay National Title. 5 day inspection period max. Closing date on or before 45 days from effective date. All appliances stay in home but not warranted by seller.

2413 Ruddenstone Way, Kissimmee
$299,000
3 Beds ⋅ 2 Baths ⋅ Terraces At Reunion SubDv. ⋅ 34747 Zip Code
Experience effortless resort living in this beautifully updated, fully furnished 3-bedroom, 2-bathroom condo in the gated Reunion Resort community. Thoughtfully enhanced by the current owner, the residence features luxury vinyl flooring throughout, new appliances, updated fixtures, and a wine refrigerator, creating a stylish, move-in-ready retreat. Located in an elevator building, the condo also offers a private balcony, its own one-car garage, and a private driveway. Whether you're looking for a primary residence, second home, vacation getaway, or short-term rental opportunity, this property offers exceptional flexibility in one of Central Florida's premier resort communities. The Terraces at Reunion features a community pool, barbecue area, and park, while Reunion Resort offers an impressive collection of amenities, including three signature golf courses designed by Jack Nicklaus, Arnold Palmer, and Tom Watson, a multi-level water park, miniature golf, tennis, fitness and spa facilities, multiple community pools, and a variety of restaurants and dining options. Ideally located approximately 30 minutes from Orlando International Airport and just a short drive from Central Florida's world-famous theme parks and attractions, Reunion combines convenience with a true resort-style experience. With 24-hour gated access and a golf-cart-friendly setting, this turnkey, fully furnished residence offers the perfect opportunity to enjoy the Florida resort lifestyle from day one.

7505 Mourning Dove Circle Unit 303, Reunion
$365,000
3 Beds ⋅ 2 Baths ⋅ Bellalago SubDv. ⋅ 34746 Zip Code
*PRICED TO SELL* Welcome to the resort-style community of Bellalago! This beautifully maintained 3-bedroom, 2-bath home with a 2-car garage offers the perfect combination of comfort, style, and value. The open-concept floor plan is ideal for entertaining, featuring a spacious kitchen overlooking the living and dining areas, while the private primary suite provides a relaxing retreat with a walk-in closet and en-suite bath. Located in one of Kissimmee's most desirable gated communities, Bellalago offers exceptional amenities including multiple resort-style pools, fitness centers, tennis and basketball courts, walking and biking trails, playgrounds, a private boat ramp and lift with direct access to Lake Tohopekaliga, fishing pier, clubhouse, on-site restaurant, and year-round community events. This home is an incredible opportunity for buyers looking for exceptional value in Bellalago. Don't miss your chance—schedule your private showing today!

1910 Goblet Cove Street, Kissimmee
$308,000
2 Beds ⋅ 2 Baths ⋅ Storey Lake SubDv. ⋅ 34746 Zip Code
Welcome to your dream retreat in the heart of Kissimmee! This beautifully maintained 2-bedroom, 2-bathroom condo is located in the highly desirable Storey Lake Resort, just minutes from Disney, Universal, shopping, dining, and Orlando’s top attractions. Fully furnished and tastefully decorated, this unit features a spacious open-concept layout, modern kitchen with granite countertops and stainless steel appliances, and a private balcony perfect for relaxing after a long day at the parks. The two generously sized bedrooms provide comfort and privacy, including a primary suite with an en-suite bathroom. Whether you're looking for a profitable short-term rental investment or a second home, this unit is turn- key and resort-ready! Storey Lake offers world-class amenities including a resort-style pool, lazy river, splash pad, fitness center, tiki bar, and more! Don’t miss this opportunity – schedule your showing today and own a piece of paradise in Central Florida!

3161 Paradox Circle Unit 304, Kissimmee
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