Osceola Homes with Private Entrance Exterior Features

Osceola Homes with Private Entrance Exterior Features

Welcome to Osceola County, Florida, a vibrant and diverse region that seamlessly blends natural beauty with modern living. Nestled in the heart of Central Florida, Osceola County is renowned for its picturesque landscapes, rich cultural heritage, and proximity to world-famous attractions, including Walt Disney World and Universal Studios. With charming communities like Kissimmee, St. Cloud, and Poinciana, residents enjoy a unique lifestyle that balances tranquility with excitement.

One of the standout features of homes in this delightful county is the availability of properties with private entrance exterior features. Imagine coming home to your own serene oasis, where you can unwind in peace after a busy day. Homes with private entrances offer a sense of exclusivity and security, making them ideal for families, professionals, or anyone seeking a little extra privacy. These distinctive properties often come with beautifully landscaped gardens, spacious patios, and inviting outdoor spaces that are perfect for entertaining or enjoying a quiet evening under the stars.

Osceola County's real estate market is thriving, with a variety of options to suit every taste and budget. Whether you’re looking for a cozy bungalow, a sprawling family home, or a luxurious estate, you’ll find it all here. With a strong sense of community, excellent schools, and abundant recreational activities, Osceola County is not just a place to live; it’s a place to thrive. Come explore the charm and allure of Osceola County today, and discover the perfect home with a private entrance that suits your lifestyle!

Newest Osceola Homes with Private Entrance Exterior Features

$299,000
3 Beds ⋅ 3 Baths ⋅ Poinciana Village 1 Nbhd 3 West SubDv. ⋅ 34758 Zip Code
Welcome to this spacious one-story pool home offering exceptional flexibility, generous living spaces, and three bedrooms, each with its own ensuite bathroom. From the moment you arrive, you’ll appreciate the extra-wide driveway providing an abundance of parking for family, guests, or recreational vehicles. Step inside to a welcoming main living area featuring a living room, dining room, and kitchen. To the right of the home, the primary suite offers a walk-in closet and private primary bathroom. Toward the back of the home, a second living room provides additional space for entertaining, relaxing, or creating a separate family gathering area. Beyond the second living room is an oversized guest bedroom with its own ensuite bathroom. This exceptionally large room offers the unique possibility of being divided into two separate rooms, depending on your needs. Off the second living room is a large Florida room that offers endless possibilities. Use it as a game room, home office, hobby space, fitness room, entertainment area, or simply an additional place to enjoy the Florida lifestyle. The home also features a large ADA-accessible bedroom and bathroom located to the left upon entering. This versatile space has its own private entrance from the left side of the home, providing added privacy and flexibility for guests or extended family. A ramp leads from the left-side fenced entrance directly to the private entry door, offering convenient accessibility. Step outside to a fully privacy-fenced backyard designed for enjoying the Florida lifestyle. The screened-in lanai features a pool, creating a wonderful space for swimming, relaxing, and entertaining year-round. The pool was resurfaced in 2021 and features a new pool pump installed in 2023. A backyard shed provides additional storage for tools, pool equipment, and outdoor belongings. Major updates provide added peace of mind, including a NEW roof and NEW AC system, both installed in 2024, a new privacy fence installed in 2026, and updated bathrooms throughout the home. With multiple living areas, three ensuite bedrooms, an oversized flexible guest suite, a large Florida room, an ADA-accessible private-entry suite, abundant parking, and a private pool, this home offers an impressive combination of space, versatility, and functionality. Whether you’re looking for room for a large family, multigenerational living, space for guests, or simply a home with plenty of options, this property is ready to accommodate a variety of lifestyles.

664 Madrid Drive, Kissimmee
$474,900
4 Beds ⋅ 3 Baths ⋅ Reunion Village Ph 4 & 5 SubDv. ⋅ 34747 Zip Code
TURNKEY short-term rental business for sale or lovely winter home. YOU CHOOSE!! Sale of the property will come with all future bookings for this property! 1st floor features a deep and open 1st floor floorplan tastefully staged for your imagination. A chef-ready kitchen awaits with a nice sized pantry and defined dining area. 1st floor master suite removes w/ laundry facilities for your visitors/in-laws. Home has been tastefully staged to spark you imagination. 2nd floor features an upstairs bonus loft w/ it's own walk-in closet can customize into a game room, home office or an extra sitting space for guests! All other bdrms are upstairs including another master bedroom. Community has resort style amenities including a waterpark/pools, Tennis Courts, Playground, restaurants, and much MUCH MORE!! Close to all major theme parks, championship golf courses, shopping, downtown Orlando areas, and dining. ????Also eligible for the GOVERNMENT BACKED Rent to own program???? Easy to Show!! Call now to book your appt!

7745 Somersworth Drive, Kissimmee
$249,000
2 Beds ⋅ 2 Baths ⋅ Stoneybrook South North Prcl Ph 2 SubDv. ⋅ 33896 Zip Code
FULL GOLF AND TENNIS MEMBERSHIP INCLUDED!!! Beautifully maintained and thoughtfully designed, this open-concept 2-bedroom, 2-bathroom villa is the perfect blend of luxury and comfort. IMMACULATE! LIGHT AND BRIGHT! Conveniently located just a short stroll from the neighborhood pool. The kitchen showcases elegant quartz countertops, slate-finish appliances, and a spacious breakfast bar, ideal for casual dining and entertaining. The primary suite offers a large, custom walk-in closet, dual sinks, and a walk-in shower. A generously sized secondary bedroom is ideal as an office or den. Additionally, a versatile flex room provides the option a separate Dining Room. This villa features high-end flooring, screened lanai, epoxy garage floor, and separate laundry room. Enjoy the ease of golf cart access throughout the entire community! This gated, resort-style community offers an unparalleled lifestyle centered around three exclusive clubhouses. The Oasis Club features a 14,000 sq ft clubhouse with a full-service restaurant, movie theater, fitness center, game room, tiki bar, lazy river, cabanas, and more. The private, resident-only Plaza clubhouse offers a second restaurant and bar, fitness center, game room, two pools, and pickleball courts—perfect for an active and social lifestyle. Now open, The Retreat Club features an exciting waterpark that brings even more fun for residents and guests. The HOA includes full access to all three clubhouses and their amenities, a complete golf and tennis membership, food and beverage credit, gated entry, full lawn maintenance, security monitoring, cable, phone, and internet. CDD and trash services are included in the property taxes. ChampionsGate Country Club offers the ultimate Florida lifestyle—whether you’re enjoying a round of golf, relaxing poolside, or dining with friends at one of the three clubhouses. All of this, just minutes from world-renowned theme parks, championship golf, premier shopping, and endless dining options in the Orlando area!

1064 Blackwolf Run Road, Davenport
$379,700
3 Beds ⋅ 3 Baths ⋅ Pinewood Gardens SubDv. ⋅ 34769 Zip Code
Welcome home to a lifestyle designed for comfort, space, and everyday enjoyment! Built in 2019, this beautiful two-story home offers 3 bedrooms, 2.5 bathrooms, a spacious den, and a 2-car garage, combining modern features with a warm and inviting feel. The open-concept living area flows seamlessly into a stylish kitchen featuring a large center island with seating, granite countertops, stainless steel appliances, and plenty of cabinetry—perfect for casual mornings, entertaining friends, or gathering with family. Step outside and enjoy a generous private, fully fenced backyard with an extended paver patio, offering plenty of room for outdoor dining, entertaining, pets, play, or simply relaxing and enjoying the Florida lifestyle. Inside, crown molding throughout the home adds an elegant finishing touch, while a smart home system with Alexa brings convenience to your daily routine. The home is also equipped with a water softener/filtration system for added comfort. The spacious den provides the flexibility today's lifestyle demands—ideal for a home office, media room, playroom, or additional living space. Upstairs, the bedrooms offer a comfortable retreat from the main living areas. Modern, spacious, move-in ready, and designed for both entertaining and everyday living—this is a home where you can truly settle in and enjoy the Florida lifestyle. Schedule your private showing today!

3821 Pinewood Gardens Boulevard, St Cloud
$650,000
2 Beds ⋅ 2 Baths ⋅ S L & I C SubDv. ⋅ 34772 Zip Code
Welcome to 4465 Story Road, where peaceful country living meets endless opportunity on 9+ acres in one of St. Cloud's fastest-growing corridors. Whether you're dreaming of building a private family compound, expanding your investment portfolio, or simply escaping the pace of the city, this exceptional property offers the rare combination of privacy, acreage, and convenience. The charming 2-bedroom, 2-bath residence features a warm, open-concept floor plan filled with rustic character. The inviting farmhouse-inspired kitchen showcases vintage charm and serves as the heart of the home, flowing seamlessly into the spacious living area—perfect for entertaining or enjoying quiet evenings overlooking your own slice of Old Florida. Both bedrooms are generously sized, including an oversized primary suite designed for comfort and relaxation. Step outside and experience what makes this property truly special. Surrounded by wide-open skies, mature trees, and friendly neighbors, you'll enjoy the serenity of country living while remaining close to everything Central Florida has to offer. The property is located near Lake Gentry, offering easy access to boating, fishing, horseback riding, and outdoor recreation, and sits adjacent to the private Gentry Airport, making it especially appealing for aviation enthusiasts. Despite its peaceful setting, you're only: Approximately 30 minutes to Lake Nona Medical City, Lake Nona Town Center, Boxi Park, Drive Shack, premier dining, shopping, and entertainment. Approximately 30 minutes to Orlando International Airport (MCO). Approximately 20 minutes to Florida's Turnpike, providing convenient access to Orlando, Kissimmee, and Central Florida's world-famous attractions. Within easy driving distance of Historic Downtown St. Cloud, East Lake Tohopekaliga, restaurants, shopping, golf, and everyday conveniences. For developers and land investors, the location is equally compelling. The surrounding Lake Gentry and Hickory Tree Road corridor continues to experience significant residential growth with nearby master-planned communities, expanding infrastructure, and new home construction. This area sits within the path of continued east Osceola County expansion, driven by the ongoing growth of Lake Nona, Medical City, and the southeastern Orlando corridor. New residential communities such as Estates at Hickory Cove are bringing additional amenities and housing to the immediate area, while continued investment throughout the Lake Gentry corridor reinforces the area's long-term appreciation potential. Properties offering this much land, privacy, and proximity to Central Florida's fastest-growing employment and lifestyle hubs are becoming increasingly difficult to find. Whether you're looking for a forever home, an equestrian retreat, a custom estate site, or a long-term investment opportunity, 4465 Story Road offers the space, location, and lifestyle to make it happen.

4465 Story Road, St Cloud
$695,000
6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code
TURNKEY VACATION RENTAL INVESTMENT MINUTES FROM DISNEY WORLD! This beautifully decorated and totally renovated 6-bedroom, 3.5-bath single-family home is located in the highly desirable Windsor Hills Resort—one of the closest vacation home communities to Walt Disney World. Designed to stand out in the competitive vacation rental market, this home is being offered turnkey and is ready for its next owner and guests. The updated interior features stylish décor, granite countertops in the kitchen and bathrooms, and fun Star Wars-themed bedrooms that are sure to be a hit with younger guests. Outside, enjoy a south-facing private pool with no rear neighbors, providing excellent sun exposure and added privacy. One of the home's standout features is the poolside theater, allowing guests to watch movies, sports and TV while relaxing in or around the pool. The converted garage has been transformed into a fun, air-conditioned game room, adding another guest-favorite amenity and entertainment space. Location within the resort is another major advantage. The home is just a short 3-block walk to the Windsor Hills clubhouse, resort pool and water park. With its combination of location, renovations, privacy, themed bedrooms and guest-focused amenities, this property offers an outstanding opportunity for buyers seeking a turnkey Disney-area vacation home and short-term rental investment.

2630 Dinville Street, Kissimmee
$1,050,000
5 Beds ⋅ 4 Baths ⋅ S L & I C SubDv. ⋅ 34772 Zip Code
A ONE OF A KIND CUSTOM ESTATE, BUILT LIKE NO OTHER. Sitting on 2.72 PRIVATE ACRES w/ NO HOA, this custom Colonial was built by a now retired developer for HIS OWN FAMILY, exceeding many modern building codes w/ a level of craftsmanship you simply cannot find anymore. MASSIVE Doric columns & timeless Chicago Brick create a BREATHTAKING entrance. Step inside to a 2 STORY FOYER w/ a radius staircase, SOLID walnut, oak, & mahogany trim, CUSTOM crown molding throughout, pocket sliding doors, 2 fireplaces, granite & marble counters, & IMMENSE closets. The main home offers 4 beds/3.5 baths, w/ all bdrms & laundry (w/ sink) upstairs, plus a private office/den w/ its own fireplace. Outside, enjoy a covered lanai w/ summer kitchen overlooking a screened pool & spa. BRAND NEW SINCE LAST ON MARKET... a stunning IN LAW SUITE w/ its own private entrance, private pool access, walk in closet, full bath, & kitchenette, bringing this home to 5 BEDROOMS TOTAL. Peace of mind included... ROOF & AC BOTH UPDATED/NEW IN 2022, keeping major systems young. Fully TILED garage. Washer, dryer, fixed cameras, in law suite fridge & microwave, ALL STAY w/ the home, plus a private well already equipped w/ water filtration. Homes of this caliber and character do not come around twice. Schedule your showing today.

4657 Hickory Tree Road, St Cloud
$349,900
4 Beds ⋅ 2 Baths ⋅ Haf Hop Unit 2 SubDv. ⋅ 34739 Zip Code
Virtually Staged. 100% financing available through a USDA loan! Experience the perfect blend of modern comfort and peaceful country living in this brand-new 2025 construction home located in charming Kenansville—with NO HOA, no rear neighbors, and no immediate side neighbors. Situated on nearly a quarter-acre, this property offers wide-open surroundings, an expansive driveway, and plenty of room for your boat, RV, jet skis, and other outdoor toys! Step inside and be welcomed by abundant natural light, an open-concept layout, impressive 15-foot vaulted ceilings, recessed lighting, and durable tile flooring throughout for easy maintenance. The modern kitchen features quartz countertops, new stainless steel appliances, generous cabinetry and pantry space, plus breakfast-bar seating for casual dining. A separate dining area provides additional space for everyday meals and entertaining. The split-bedroom floor plan offers added privacy, with the secondary bedrooms located on the opposite side of the home from the primary suite. The spacious primary retreat also showcases soaring vaulted ceilings, a walk-in closet, and a private en-suite bathroom complete with dual vanities, a soaking tub, and a separate glass-enclosed walk-in shower. Additional highlights include a private well with an advanced water-filtration system and a new septic tank. Enjoy peaceful mornings, open skies, natural surroundings, and the freedom of country living without sacrificing modern finishes. Outdoor adventure is always nearby! Explore Lake Marian, a 6,000-acre spring-fed lake known for fishing, boating, kayaking, wildlife, and beautiful sunsets. A public boat ramp, fishing pier, and Lake Marian Restaurant are just minutes away. Wild Florida’s Drive-Thru Safari Park, Gator Park, animal encounters, and airboat adventures are also within easy reach. Enjoy convenient access to St. Cloud and approximately an hour to Orlando-area conveniences. If you have been dreaming of a new modern home with privacy, open space, outdoor recreation, and no HOA, this is the one!

121 S Canoe Creek Road, Kenansville
$1,100,000
2 Beds ⋅ 2 Baths ⋅ S L & I C SubDv. ⋅ 34769 Zip Code
THERE ARE SEVERAL OUTBUILDINGS ON THE PROPERTY FOR STORAGE PURPOSES. THE INTERIOR OF THE HOME IS VERY WELL KEPT. THE PROPERTY HAS LONG BEEN THE HOME OF THE OWNER'S AGRICULTURAL AND RECREATIONAL HOBBIES. IT IS AN AGRICULTURAL SETTING WITH GAME HENS/ROOSTERS, DOG KENNELS, AND SECURITY GATES THROUGHOUT THE PROPERTY. INCLUDED IS A 4 STALL BARN WITH TACKROOM, AN R/V SLAB WITH UTILITIES & A NEWLY BUILT WOOD GAZEBO. THE PROPERTY IS LOCATED OFF OF A PAVED ROAD (CHAPLAIN) AND IS BESIDE FUTURE GROWTH AREAS DESIGNATED ON FUTURE USE MAPS AS TOWNHOMES, HOMES, AND SCHOOLS. PLEASE CHECK WITH THE COUNTY AS TO CURRENT DRAWINGS OF FUTURE USES. IF YOU LIKE A TRUE, COUNTRY ATMOSPHERE WITH AN ABUNDANCE OF PRIVACY ON THE PROPERTY, THIS IS YOUR SHANGRI LA... GIVE US A CALL. EASY TO SHOW.

3845 Chaplain Road, St Cloud
$332,000
4 Beds ⋅ 2 Baths ⋅ Poinc Vlg 1 Nbd 1 S SubDv. ⋅ 34758 Zip Code
Virtually Staged. Welcome to this beautifully maintained 2023-built D.R. Horton Cali model featuring 4 bedrooms, 2 bathrooms, and 1,872 sq. ft. of thoughtfully designed living space. The open-concept layout offers a spacious kitchen with a large island overlooking the living and dining areas, perfect for everyday living and entertaining. The private primary suite features a walk-in closet and en-suite bath with dual vanities. Enjoy the covered lanai, a 2-car garage, and smart home features. Conveniently located just 20 minutes from ChampionsGate and 30 minutes from Walt Disney World, with easy access to shopping, dining, schools, and major highways. Schedule your private showing today!

658 Cotulla Drive, Kissimmee
$275,000
3 Beds ⋅ 3 Baths ⋅ Turtle Creek Ph 1a SubDv. ⋅ 34771 Zip Code
Discover this spacious 3-bedroom, 2.5-bath townhome in the desirable Turtle Creek community of Saint Cloud. Designed for comfort and functionality, the home features an open family and dining area with a mix of tile and carpet flooring. The modern kitchen offers stainless steel appliances, ample counter space, and a pantry, making everyday living and entertaining easy. The spacious primary suite includes a walk-in closet and a private en-suite bath with dual sinks and a walk-in shower. Two additional bedrooms provide flexibility for family, guests, or a home office. Enjoy your private back patio, perfect for relaxing or entertaining. Additional features include a two-car garage and an in-unit washer and dryer. Conveniently located near local schools with easy access to Highway 192, US-441, Florida's Turnpike, and Lake Nona Medical City via Narcoossee Road, this home offers the perfect blend of comfort, convenience, and location Conveniently located near local schools with easy access to Highway 192, US-441, Florida's Turnpike, and Lake Nona Medical City via Narcoossee Road, this home offers the perfect blend of comfort, convenience, and location.

1570 Softshell Street, St Cloud
$529,990
4 Beds ⋅ 4 Baths ⋅ Waters At Center Lake Ranch Ph 1a SubDv. ⋅ 34771 Zip Code
Virtually Staged. **Move-in ready with over $65,000 in builder upgrades and a transferable builder warranty!** This beautifully maintained 4-bedroom, 3.5-bath home with a dedicated office offers 2,597 square feet of thoughtfully designed living space in the desirable Waters at Center Lake Ranch community. Features include an open-concept layout, a gourmet kitchen with quartz countertops and natural gas appliances, a screened-in lanai, fully fenced backyard, and an insulated, climate controlled garage with epoxy flooring and a Level 2 EV charger. Conveniently located just minutes from Lake Nona, Medical City, Orlando International Airport, shopping, dining, and major highways, this exceptional home combines comfort, style, and convenience. Schedule your private showing today!

5268 Kildare Place, St Cloud
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