Kissimmee Homes with Two Story Style

Kissimmee Homes with Two Story Style

Welcome to Kissimmee, a vibrant city located in Osceola County, Florida. Known for its proximity to world-famous attractions like Walt Disney World Resort and Universal Studios, Kissimmee offers a perfect blend of entertainment and relaxation.

If you're looking for a home with a two-story style in Kissimmee, you're in luck! The city boasts a variety of properties that cater to different tastes and preferences. Two-story homes are popular among families and individuals looking for spacious living areas and distinct separation between living and sleeping quarters.

Whether you're interested in a modern two-story townhouse in a gated community or a charming traditional home with a backyard, Kissimmee has options to suit every lifestyle. Enjoy the Florida sunshine from your second-floor balcony or host gatherings in your open-concept living space.

With a bustling downtown area, top-rated schools, and easy access to major highways, Kissimmee is a sought-after destination for homebuyers. Explore the diverse neighborhoods and discover the perfect two-story home that meets your needs and exceeds your expectations.

Experience the best of Florida living in Kissimmee – where two-story homes offer style, comfort, and endless possibilities. Let us help you find your dream home in this dynamic city!

Newest Kissimmee Homes with Two Story Style

4 Beds ⋅ 3 Baths ⋅ S5155807 MLS

Welcome to **4385 Twisted Twig Bnd**, a spacious **4-bedroom, 2.5-bath home located in the desirable Storey Creek community of Kissimmee**. Built in 2024 and offering approximately **2,357 square feet of living space**, this home combines comfort, functionality, abundant natural light, and one of its most attractive features: **no rear neighbors and peaceful views of a natural area**, creating added privacy and a relaxing setting. The main living area features an appealing **open-concept layout** that seamlessly connects the family room, dining area, and modern kitchen, creating an ideal space for everyday living and entertaining. The kitchen includes **quartz countertops, stainless steel appliances, shaker-style cabinetry, an undermount sink, LED lighting, and a large center island**. Upstairs, the spacious **owner’s suite** features a **private en-suite bathroom and a large walk-in closet**. Three additional bedrooms, a **versatile loft**, and a conveniently located laundry room provide flexible space for family, guests, a home office, or additional living areas. The property also features a **2-car garage plus a driveway with space for 2 additional vehicles**, adding convenience and functionality for everyday living. Storey Creek enhances the lifestyle with excellent community amenities including a **resort-style swimming pool, clubhouse, fitness center, playground, dog park, and basketball court**. Its convenient location provides easy access to **shopping, dining, schools, medical services, major roadways, and Central Florida’s renowned attractions**. **Schedule your private showing today and experience the spacious layout, natural light, added privacy with no rear neighbors, and the Storey Creek lifestyle that make this home stand out.**

4385 Twisted Twig Bend, Kissimmee

4 Beds ⋅ 3 Baths ⋅ O6434314 MLS ⋅ 8217 BLDG.

Welcome to 8217 Surf St, a beautifully furnished 4-bedroom, 3-full-bath corner townhome located in the highly sought-after Margaritaville Resort Orlando. This spacious two-story home offers an open-concept living and dining area filled with natural light, stylish wood-look tile flooring, and a modern kitchen featuring quartz countertops, stainless steel appliances, ample cabinetry, and everything needed for a fully equipped vacation rental. The flexible floor plan includes a queen bedroom and full bathroom downstairs, while upstairs features three additional bedrooms: a spacious king bedroom, a queen bedroom, and a bunk room with two twin beds. Offered completely turnkey, the property includes all appliances, furniture, TVs, décor, artwork, housewares, kitchen necessities, dishware, linens, and furnishings, allowing the next owner to begin enjoying or renting the property right away. Whether you're looking for an income-producing short-term rental, a second home, or your own Florida vacation retreat, this property offers incredible flexibility. Margaritaville Resort Orlando offers a true resort lifestyle with multiple pools, fitness amenities, Island H2O Water Park, and convenient access to the restaurants, shopping, entertainment, and live music at Sunset Walk. Best of all, you're just minutes from Walt Disney World and Orlando's world-famous attractions. With its desirable corner location, spacious 4-bedroom layout, and complete turnkey setup, 8217 Surf St is an exceptional opportunity to own in one of Central Florida's most unique vacation resort communities—where every day can feel like a vacation.

8217 Surf Street, Kissimmee

4 Beds ⋅ 4 Baths ⋅ S5155606 MLS

NEWER ONE OWNER HOME, WELL LOCATED IN THE FANTASIC SUBDIVISION OF BELLALOGO, TO MANY FEATURES TO LIST, LAKE FRONT COMMUNITY, PARKS, PLAYGROUNDS, DOG PARK, COMMUNITY POOL, ETC. HOME FEATURES AN OPEN LAYOUT FOR FAMILY AND GREAT GET TOGETHERS, BIG REAR YARD TO ALLOW EXTENDED LIVING OUTSIDE WITH FRIENDS FAMILY AND NEIGHBORS. 4 LARGE BEDROOM AND 3.5 BATHS, GAME ROOM, ETC . CHIEF STYLE KITCHEN WITH ALL THE FEATURES YOU WOULD EXPECT. WELL APPOINTED FEATURES THROUHTOUT THE HOME. ALSO INCLUDES THE EXTRA LARGE AND VERY MUCH DESIRED 3 CAR GARAGE, PROVIDING BOTH CONVENYENCE AND MULITPLE STORAGE OPTIONS. THIS HOME HAS IT ALL AND IS PRICED TO MOVE.

2931 Agostino Terrace, Kissimmee

3 Beds ⋅ 3 Baths ⋅ S5155515 MLS ⋅ Na BLDG.

Welcome to 2039 Cypress Bay Blvd, a well-maintained 3-bedroom, 2.5-bath townhome offering a comfortable living space in a convenient Kissimmee location. This home features an open and functional floor plan with tile and laminated flooring throughout the house. A screened rear porch—perfect for relaxing outdoors. Upstairs you'll find all three bedrooms, including the primary suite, along with two full bathrooms. Additional features include an attached 1-car garage and an oversized paver driveway providing plenty of additional parking. Conveniently located near shopping, dining, schools and major roadways, with easy access to the Florida Turnpike, Orlando International Airport, Lake Nona/Medical City and Central Florida's attractions. Whether you're looking for a primary residence or an investment property, this townhome offers an excellent combination of space, location and value.

2039 Cypress Bay Boulevard, Kissimmee

5 Beds ⋅ 6 Baths ⋅ O6434248 MLS

Welcome to your private resort retreat at Encore Club at Reunion! A stunning five-bedroom, five-and-a-half-bath residence built in 2020, offering 2,945 square feet of beautifully designed living space and an exceptional opportunity to own a turnkey vacation home in one of Central Florida’s most sought-after resort communities. From the moment you arrive, the elegant driveway and impressive curb appeal set the stage for the experience inside. The bright, open-concept floor plan was thoughtfully designed for comfort, style, and effortless entertaining. At the heart of the home, the gourmet kitchen seamlessly connects to the spacious living and dining areas and features beautiful California-style countertops, contemporary finishes, and an inviting layout ideal for entertaining family, friends, or vacation guests. Fully furnished and professionally decorated, this home is truly turnkey. Every detail has been carefully selected to create an upscale yet welcoming atmosphere while maximizing its appeal as a vacation rental. Each of the five generously sized bedrooms features a private en-suite bathroom, offering guests the comfort, privacy, and convenience expected from a luxury resort home. Step outside and discover your own private oasis. The sparkling private pool and spa create the perfect backdrop for relaxing under the Florida sun, enjoying an evening cocktail, or creating unforgettable vacation memories with family and friends. The spacious outdoor living area seamlessly extends the home's entertaining space and delivers the quintessential Florida resort lifestyle. And the resort experience doesn't stop at your doorstep. Located just steps from Encore's spectacular water park and clubhouse, residents and guests enjoy an impressive collection of resort-style amenities, including on-site restaurants, tennis courts, a state-of-the-art fitness center, basketball courts, playgrounds, and more—all within the security of a gated, professionally managed community. Whether you're looking for a luxury vacation home, a personal Florida getaway, or a high-performing short-term rental investment, this exceptional property offers the perfect combination of comfort, amenities, location, and investment potential. Ideally located just minutes from Walt Disney World, Universal Studios, championship golf, world-class shopping, and exceptional dining, this home places you at the center of Orlando's world-renowned vacation destination. Experience the best of resort living and investment opportunity at Encore Club at Reunion.

267 Southfield Street, Kissimmee

5 Beds ⋅ 5 Baths ⋅ O6434299 MLS ⋅ 8907 BLDG.

Turnkey 5-Bedroom Townhome – Short-Term Rental Approved! Welcome to this beautifully furnished 5-bedroom, 4.5-bathroom townhome, thoughtfully designed with fun Mickey Mouse and Harry Potter-themed bedroom, perfect for vacationers and investors alike. This move-in-ready property comfortably accommodates up to 12 guests and offers the ideal combination of space, comfort, and entertainment. The open-concept main living area features a modern kitchen with granite countertops, stainless steel appliances, ample cabinetry, and a spacious island perfect for gathering and entertaining. Step outside to your private screened-in pool and patio, an inviting space to relax and unwind after a day at the theme parks. Upstairs, a versatile loft provides additional room for entertainment, lounging, or family time. Guests can enjoy Windsor at Westside’s impressive resort-style amenities, including a clubhouse, resort pool, lazy river, water slide, fitness center, sports courts, game room, and playground—bringing the full vacation-resort experience right to the community.

8907 Sydney Avenue, Kissimmee

4 Beds ⋅ 3 Baths ⋅ O6434257 MLS

'PIRATES IN PARROTDISE' Cottage at Margaritaville Resort Orlando! Spacious Model 1384-C with 3 Bedrooms, 3 Bathrooms and an ADDITIONAL BONUS BEDROOM, BACK PATIO RETRACTABLE AWNING and a HOT TUB! Premium Location Near the Pedestrian Bridge! Spacious Living Room has a HUGE 75-INCH TV. IMMACULATE CONDITION ~ WELL MAINTAINED HOME. This home has NEVER been an STR and has been used as a SECOND HOME and LONG-TERM RENTAL most recently. First Floor Bedroom has En-Suite Bathroom and French Doors Leading to Spacious Backyard Patio with a Gorgeous GRASSY Backyard and TIKI HUTS. Second Floor has Primary En-Suite Bedroom with Front Balcony Access. Bonus Room has been Converted to a Bunk Room. The Kitchen features Upgraded Appliances, and Quartz Countertops. This Home also features Tile Flooring, Ceiling Fans Throughout, Washer and Dryer, Landscaping has Beautiful Foliage! All Furniture, Linens, Housewares and Decor INCLUDED IN LIST PRICE! Includes HIGH END ETHAN ALLEN FURNISHINGS, 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 and More! This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! LOCATED MINUTES FROM DISNEY PARKS! Come Enjoy the Margaritaville Lifestyle in Paradise!

8036 Surf Street, Kissimmee

4 Beds ⋅ 4 Baths ⋅ O6434147 MLS

Beautiful MAIN VILLAGE home overlooking PRESERVE, POND and GOLF COURSE! This exquisite floor plan features 4 bedrooms and 3.5 baths plus office/ den (potential guest bedroom first floor)! Spacious foyer upon entry, and lots of windows, beautiful plantation shutters, and crown molding throughout. Features include hardwood flooring, charming wood burning fireplace, and detailed custom shelving. The Den/Office features a newly installed California Closets shelving unit. Light and bright Kitchen featuring recently updated quartz countertops and a beautifully coordinating backsplash. Enjoy the breakfast nook area with serene views of pond and golf course. Kitchen opens to family room, providing plenty of space to gather family and friends. Spacious bedrooms upstairs include 4 bedrooms and 3 bathrooms. The primary bedroom features a walk- in closet. New Water Heater 2025, AC 2020, Roof 2017 You'll love the long driveway and very Private lot! 2 CAR GARAGE w/storage and new epoxy flooring. This home is located on a beautiful tree lined street in fantastic conservation setting in Celebration's Main Village. The large backyard offers plenty of room for a pool! Walk to schools, downtown shops, restaurants, library and Golf Course. Hurry, this home won't last. You can't beat this location!

915 Jasmine Street, Kissimmee

5 Beds ⋅ 3 Baths ⋅ S5155785 MLS

2025-BUILT 5-BEDROOM HOME – ONLY $369,000 – JUST 19 MILES FROM MAGIC KINGDOM! Exceptional value! Offered at $369,000, this beautiful 2024-built, 5-bedroom, 3-bathroom home with a 2-car garage is one of the lowest-priced homes of its size and age in the area. The spacious open-concept floor plan features a modern kitchen with quartz countertops, stainless steel appliances, a large center island, and a great room ideal for everyday living and entertaining. A first-floor bedroom with a full bathroom provides excellent flexibility for guests, extended family, or a home office. Enjoy a private backyard overlooking lake and conservation views with no rear neighbors. Energy-efficient construction provides additional comfort and potential savings on utility costs. Community amenities currently include a pool, playground, and dog park, with additional resort-style amenities planned, including a clubhouse, fitness center, café, sports courts, rock-climbing wall, and lap pool. Conveniently located approximately 19 miles from Magic Kingdom, with easy access to shopping, dining, schools, major highways, and Central Florida attractions. 5 Bedrooms | 3 Full Bathrooms | 2-Car Garage | Built in 2024 | Lake & Conservation Views | No Rear Neighbors | $369,000 Excellent opportunity for buyers looking for space, newer construction, location, and exceptional value in Central Florida.

5618 Gingham Drive, Kissimmee

3 Beds ⋅ 2 Baths ⋅ O6433300 MLS ⋅ 2952 BLDG.

Welcome to Lucaya Village! This charming 3-bedroom, 2-bathroom home offers approximately 1,300 sq. ft. of living space in a gated community ideally located in the heart of Kissimmee. The functional two-story floor plan features a bedroom and full bathroom on the first floor, providing added convenience and flexibility, while two additional bedrooms and a second bathroom are located upstairs. Enjoy the comfort of central air conditioning and a well-equipped kitchen featuring a refrigerator, range, microwave, and dishwasher. The community offers a swimming pool and additional amenities, while the HOA includes services such as cable TV, internet, exterior maintenance, pest control, and 24-hour guard service. Conveniently located near US-192 with easy access to shopping, dining, entertainment, and Central Florida's world-famous attractions. Whether you're looking for a primary residence or an investment property, this home offers an excellent opportunity in one of Kissimmee's most convenient locations. Schedule your private showing today!

2952 Lucayan Harbour Circle Unit 103, Kissimmee

2 Beds ⋅ 3 Baths ⋅ O6434097 MLS ⋅ 2702 BLDG.

Enjoy resort style Florida living in this fully furnished 2 bedroom, 2 bathroom lakefront townhome, just minutes from Disney World and Central Florida’s top attractions. The open floor plan offers a comfortable living room, dining area, and kitchen with no carpet throughout. The primary bedroom features a private balcony overlooking the beautiful pond and fountain. Step outside to the screened-in, enclosed patio with a hot tub perfect for relaxing and enjoying the Florida weather. The community offers fantastic resort style amenities including a restaurant, clubhouse, pool, gym and water slide, making this an ideal vacation home or investment property. With its lakefront setting, prime location, full furnishings and potential rental income, this townhome offers the perfect combination of comfort, convenience and Florida resort living. Call now for your private tour.

2702 Corvette Lane, Kissimmee

4 Beds ⋅ 4 Baths ⋅ O6434044 MLS ⋅ Na BLDG.

Turnkey 4BR/3.5BA End-Unit Villa in Regal Oaks Resort — Miles to Disney Renovated and carpet-free throughout, this 4-bedroom, 3.5-bath end-unit townhome in the gated Regal Oaks Resort offers sleeping capacity for up to 10 — an ideal short-term rental investment, second home, etc, just miles from the Walt Disney World entrance and walking distance to Old Town and Fun Spot. The home is currently operating as a successful short-term rental and conveys fully furnished — a true turnkey opportunity for a buyer to assume operations at closing. Each bedroom is fully furnished with a flat-screen TV, dresser, and closet. The home includes a spacious living area, fully equipped kitchen, and full-size washer/dryer. Dual master suites provide flexibility and privacy: a first-floor master with a Disney Mickey Mouse theme, queen bed plus extra-long twin, and full en-suite bath; and a second-floor master with a king bed, en-suite bath, walk-in closet, and private balcony. Two additional upstairs bedrooms share a third full bath. A half bath completes the main floor. Ownership includes access to Regal Oaks' resort-style clubhouse amenities: pools with water slides, spa, fitness center, tiki bar, on-site restaurant, game room, tennis courts, convenience shop, etc. Unbeatable location: several miles to Disney, 8.5 to SeaWorld, 12.3 to Universal. Old Town and Fun Spot are walkable; Celebration Town Center is 3 miles; Publix is 1.2 miles and Super Target 3 miles. Multiple golf courses and dinner shows are within 3–12 miles. Sold as-is with right to inspect. Buyer and buyer's agent to verify all room dimensions, square footage, HOA fees, lease restrictions, HOA regulation, etc

2700 Camaro Drive, Kissimmee

Start Your Search