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

5 Beds ⋅ 4 Baths ⋅ O6435109 MLS

Virtually Staged. Welcome to 2049 Rock Maple Bend, located in the desirable Storey Creek community of Kissimmee. This impressive Exbury Executive model by Landsea Homes offers 3,802 square feet of living space with 5 bedrooms, 3.5 bathrooms, and a 3-car garage, combining generous living space with over $100,000 in thoughtfully selected upgrades and designer details . From the moment you enter, the home showcases elevated finishes including custom ceiling wood beams and wall trim accents, beautiful pendant lighting, and wrought iron railing. The gourmet-style kitchen features quartz countertops, 42-inch cabinetry, large center island, stainless steel range hood, and plenty of space for gathering and entertaining. The primary suite is on the first floor complete with his and her walk in closets and a spa like primary bathroom. Separate vanities surround a walk through tiled shower with glass window and stand alone tub. Upgraded wrought iron railings surround the top floor balcony overlooking the downstairs living space. At the top of the stairs there is a large loft surrounded on both sides by two bedrooms and baths. Additional upgrades include an EV car charger outlet 240V, whole-home water filtration system, reverse osmosis water treatment, epoxy garage floor, garage storage racks, pavered driveway, security system, and smart-home features. The 3-car garage offers additional room for vehicles and storage. Storey Creek residents enjoy an impressive collection of community amenities, including a resort-style community pool, clubhouse, tennis and basketball courts, walking trails, dog park, and playground. Built with space, style, and functionality in mind, this executive home offers the opportunity to enjoy modern living in one of Kissimmee's amenity-rich communities. Schedule your private showing today!

2049 Rock Maple Bend, Kissimmee

6 Beds ⋅ 5 Baths ⋅ O6436601 MLS

Pack your bags! Your vaction home is ready with everything you need. This 6/5 home offers to luxurious suites one upstairs and one downstairs. Cooking and meals will be fun and easy with this beautiful and well equipped kitchen. The spacious family roomand dining combo offers a comfortable and relaxing place to wind down after enjoying all the nearby parks and recreation. The screened pool and patio is the perfect place to cool off. Paradise palms is close to Disney, Universal, restaurants, shopping, and highways. Schedule your tour today.

8935 Cuban Palm Road, Kissimmee

3 Beds ⋅ 3 Baths ⋅ S5155946 MLS ⋅ 0149 BLDG.

Short Sale. Beautiful, nearly-new townhome built in 2024 in the desirable Osceola Village Center community in Kissimmee! This 3-bedroom, 2.5-bath home offers modern finishes and a low-maintenance, move-in-ready layout — perfect for first-time buyers or investors. Conveniently located with easy access to major highways, shopping, dining, and Central Florida's world-famous attractions. Priced to sell as a short sale, subject to third-party lender approval. Buyer/buyer's agent to submit proof of funds or a pre-approval letter with all offers. Don't miss this opportunity to own an almost-new home at a great price — schedule your showing today!

1485 Isleta Loop, Kissimmee

4 Beds ⋅ 3 Baths ⋅ O6436558 MLS

Short Sale. Experience resort-style living in this fully furnished 4-bedroom, 3-bathroom vacation home located in the highly desirable Solara Resort. Designed with short-term rentals in mind, this property is ready for its next owner to enjoy personally or add to their investment portfolio. The home features an open and spacious layout, stylish professionally selected furnishings, a fully equipped kitchen, and a private heated pool and spa perfect for relaxing after a day at the parks. Solara Resort offers an exceptional lineup of amenities, including a grand clubhouse, heated resort-style pool, FlowRider Surf Simulator (*additional fee required), fitness center, on-site bar and grill, coffee bar, sundries store, basketball, soccer and sand volleyball courts, playground, poolside cabanas, indoor and outdoor lounge areas, and a game room with a sports simulator featuring golf, football, soccer and more. Conveniently located near Walt Disney World, Disney Springs, Universal Studios, SeaWorld, International Drive, dining, shopping and entertainment. Fully furnished and ready to go, this is a great opportunity to own a vacation home with short-term rental potential in one of Central Florida’s popular resort communities.

1841 Sawyer Palm Place, Kissimmee

5 Beds ⋅ 5 Baths ⋅ O6436144 MLS ⋅ N/A BLDG.

Privacy, flexibility, and vacation-ready living come together at 2147 Cooper Bell Place. This furnished 5-bedroom, 4.5-bath end-unit townhome offers 2,294 square feet in the gated Solara Resort community. One of the home’s most appealing features is its open rear setting, where the screened private pool and covered lanai are not positioned directly behind another row of townhomes, creating a more relaxed and private outdoor experience. Inside, the spacious kitchen island anchors an open gathering area connecting the kitchen, dining space, and living room. A first-floor primary suite provides convenience and separation, while the second floor features 4 additional bedrooms, including 2 creatively themed rooms, plus a loft that can serve as another entertainment or relaxation area. Offered furnished and located in a community that permits short-term rentals, the property provides options for use as a personal getaway, vacation rental, or combination of both. Solara Resort features a resort-style pool, clubhouse, fitness center, sports courts, playground, lounges, dining options, and other recreational amenities. Walt Disney World, shopping, restaurants, and many of Central Florida’s most popular attractions are all within convenient reach.

2147 Cooper Bell Place, Kissimmee

5 Beds ⋅ 4 Baths ⋅ O6436518 MLS

fFexible and highly desirable 5 bedroom property with pool and spa located just 10 minutes from Walt Disney World. This home can be used for many purposes: primary residence, seasonal retreat, or income-producing investment. Home may be sold fully furnished. The community allows short-term rentals, making it ideal for Airbnb or vacation rental use. Enjoy living in the home full-time, or use it seasonally and rent it out when you’re not there to offset expenses or generate income. Its prime location near Disney, shopping, dining, and entertainment makes it especially attractive to guests and long-term residents alike. A rare opportunity to own a property that offers lifestyle flexibility, strong rental potential, and proximity to Central Florida’s top attractions.

2915 Blooming Alamanda Loop, Kissimmee

6 Beds ⋅ 3 Baths ⋅ O6436142 MLS

Welcome to this impressive two-story single-family home in the highly sought-after Lake Berkley Resort, a gated community in Kissimmee, FL. This spacious 6-bedroom, 3-bath property features a 2-car garage, an inviting screened-in pool and lanai, and has become a STR favorite with strong booking history and future reservations already in place. The home is TURN KEY, offering versatility for both personal use and continued investment. Recent improvements include kitchen appliances, exterior paint, flooring, refinished pool, pool pump and heater with remote access. Additional upgrades include Wi-Fi enabled remote access to the front door and HVAC. The washer and dryer were replaced in 2022, and the roof was replaced in 2019. The first floor offers a comfortable family room, eat-in kitchen, primary bedroom with en-suite, two additional bedrooms, a full bath, and a dedicated laundry room. Sliding glass doors from both the kitchen and living room lead to the screened pool area—perfect for entertaining or enjoying Florida sunshine. The second floor features three additional bedrooms and a full bath with tub, providing ample space for guests. All bedrooms have generous closet storage. The primary suite includes a large walk-in closet, a locked owner’s closet, and a spacious en-suite bathroom with dual sinks, soaking tub, and separate shower. Lake Berkley Resort residents and guests enjoy a wide range of amenities including a clubhouse, community pool, tennis courts, fitness center, jogging trail, and fishing pier. The community’s prime location places you less than 15 miles from all Disney Parks and Universal Studios, with convenient access to major highways, shopping, dining, and entertainment. Whether you’re seeking a vacation home, a full-time residence, or a proven income-producing rental, this exceptional property offers unmatched flexibility and value.

4613 Formby Court, Kissimmee

3 Beds ⋅ 3 Baths ⋅ O6434733 MLS

Enjoy the convenience of being located in the heart of Kissimmee, with everyday shopping, dining, recreation and entertainment all within easy reach. The surrounding Buenaventura Lakes area offers a variety of neighborhood shops, restaurants, grocery options and local services, making errands and dining out simple and convenient. Nearby parks and recreational facilities provide opportunities to enjoy Florida's year-round outdoor lifestyle, while Kissimmee Lakefront Park and Lake Tohopekaliga offer scenic waterfront views, walking areas, fishing and family-friendly recreation. The location also puts you within convenient reach of Historic Downtown Kissimmee, where locally owned restaurants, shops, community events and the lakefront create a welcoming local atmosphere. For entertainment and weekend outings, the area's popular attractions, theme parks, shopping destinations and dining districts are all accessible from this Central Florida location. With major roadways nearby, this is a convenient place to enjoy everything Kissimmee and the surrounding Orlando area have to offer.

2830 Paynes Prairie Circle, Kissimmee

3 Beds ⋅ 3 Baths ⋅ S5156269 MLS ⋅ Building BLDG.

SHORT-TERM RENTALS, LONG-TERM RENTALS OR PRIMARY RESIDENCE ALLOWED! An exceptional opportunity for investors, vacation-home buyers, or anyone looking for a beautiful low-maintenance home in Central Florida. This like-new townhome was built just 5 years ago and still has select builder warranties active, providing additional peace of mind to its next owner. One of the biggest advantages of this property is its outstanding flexibility — use it as a short-term vacation rental, long-term investment property, second home, or primary residence. An excellent opportunity for buyers looking to generate rental income and maximize their return on investment. Enjoy a low HOA of only $290 monthly, which includes maintenance and replacement of the roof, as well as exterior/building maintenance, helping reduce the owner’s individual maintenance responsibilities and potentially helping with insurance-related ownership costs. The community also offers resort-style amenities, including a swimming pool, fitness center, tennis courts, playground, and clubhouse. LOCATION, LOCATION, LOCATION! Conveniently located near Central Florida’s world-famous attractions, including approximately 15–20 minutes from Walt Disney World, 10–15 minutes from Old Town and Fun Spot Kissimmee, 20–25 minutes from SeaWorld, 25–30 minutes from Universal Orlando, and approximately 40–45 minutes from LEGOLAND Florida. Shopping, dining and everyday conveniences such as Publix, Walmart, restaurants and major roadways are also just minutes away.

4814 Coral Castle Drive, Kissimmee

8 Beds ⋅ 6 Baths ⋅ O6436405 MLS

Beautifully decorated and Spacious 8-bedroom, 6-bathroom vacation home just minutes from Disney and major attractions. Ideal for short-term rental, investment, or personal use. This well-maintained, fully furnished corner lot property features an open floor plan, fully equipped kitchen, large living and dining areas, and generously sized bedrooms with excellent decoration. Enjoy a private pool and spa, along with outdoor space perfect for relaxation and entertainment. Located in the desirable Windsor at Westside community, offering resort-style amenities including clubhouse, fitness center, and community pool. Zoned for short-term rentals with strong income potential. Conveniently located near shopping, dining, and major highways. Schedule your private showing today.

1599 Lima Avenue, Kissimmee

8 Beds ⋅ 6 Baths ⋅ O6436398 MLS

Turnkey 8-bedroom, 6-bath fully furnished pool home located in the highly desirable Windsor at Westside Resort. This well-maintained property offers over 4,000 sq ft of living space with a functional and spacious layout ideal for short-term rental use. The home features an open-concept main floor with a large kitchen, breakfast bar, formal dining area, and expansive living room. A first-floor bedroom and full bath provide convenience, along with a rear primary suite offering direct pool access and functioning as a pool bath. The covered lanai overlooks a private setting with no rear neighbors and a pond to the side. Upstairs includes a large loft/game area with projector and gaming stations. The second floor consists of 6 bedrooms and 4 bathrooms, including multiple themed rooms, a Jack-and-Jill bathroom with dual vanities, and additional ensuite configurations. In total, the property offers 3 ensuite bedrooms. The garage has been converted into a game room, enhancing rental appeal. Located just minutes from major theme parks, shopping, and dining. Windsor at Westside offers resort-style amenities including a 10,000 sq ft clubhouse, pool, lazy river, restaurant/bar, fitness center, sports courts, and more. HOA includes gated access, lawn care, daily valet trash service, cable, internet, and full access to amenities. Property has strong rental potential and is being sold fully furnished and ready for immediate use or income production.

1690 Lima Avenue, Kissimmee

4 Beds ⋅ 3 Baths ⋅ S5155625 MLS

Welcome to a spacious and inviting 2-story, 4-bedroom, 2.5-bathroom home offering comfort, functionality, and plenty of room for everyday living. Step inside to a welcoming formal living room and dining room, perfect for entertaining guests or enjoying special family gatherings. The heart of the home features an open kitchen and family room combination, creating a comfortable space where everyone can gather, relax, and enjoy time together. Upstairs, you'll find generously sized bedrooms, including a large primary suite designed for comfort and privacy. The primary bedroom features a private en-suite bathroom and two walk-in closets, providing an abundance of storage and a spacious retreat at the end of the day. This home also offers valuable recent updates, including a new A/C system, new garage door opener, and new dishwasher. The roof was replaced in 2016, adding additional peace of mind for its next owner. You'll enjoy convenient access to shopping, dining, entertainment, major highways, and Central Florida's world-famous attractions, making this an ideal place to call home.

905 Gloucester Court, Kissimmee

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