Kissimmee/Celebration Homes with Two Story Property Description

Kissimmee/Celebration Homes with Two Story Property Description

Welcome to Kissimmee and Celebration, two enchanting communities nestled in the heart of Osceola County, Florida. Known for their vibrant atmosphere and proximity to world-renowned attractions, these areas offer a unique blend of suburban charm and urban convenience. Kissimmee, with its rich history and diverse culture, boasts an array of recreational activities, shopping destinations, and dining options that cater to every palate. Just a stone's throw away, Celebration, designed by The Walt Disney Company, exudes a picturesque small-town vibe with its tree-lined streets, stunning parks, and delightful community events.

In this idyllic region, you’ll find a variety of stunning homes, particularly those with two-story layouts that provide ample space for families and individuals alike. These properties often feature open-concept designs, allowing for seamless transitions between living, dining, and kitchen areas, perfect for entertaining guests or enjoying cozy family evenings. With generous square footage, two-story homes offer multiple bedrooms and bathrooms, ensuring comfort and privacy for everyone.

Many of these residences come with modern amenities, including gourmet kitchens, spacious master suites, and outdoor living spaces that invite you to bask in the Florida sunshine. Whether you’re looking for a home with a view of serene lakes or one nestled in a vibrant community, Kissimmee and Celebration have it all. Experience the magic of Florida living in a two-story home that perfectly complements your lifestyle. Embrace the charm, community spirit, and endless opportunities that await you in this beautiful region!

Newest Kissimmee/Celebration Homes with Two Story Property Description

$580,000
4 Beds ⋅ 5 Baths ⋅ Magic Village Resort 2 SubDv. ⋅ 34747 Zip Code
Located in the exclusive Magic Village Yards, a luxury gated resort community just minutes from Walt Disney World®, this stunning 4-bedroom, 4-bathroom residence offers the perfect combination of comfort, sophistication, and excellent investment potential. Designed for short-term rentals, this property is ideal as a vacation home or income-producing asset in one of Central Florida’s most desirable areas. The residence features a spacious open-concept floor plan, abundant natural light, a fully equipped modern kitchen with stainless steel appliances, and elegant living and dining areas designed for both relaxation and entertaining. Each bedroom includes its own private bathroom, providing comfort and privacy for both owners and guests. The property also features a private patio, perfect for enjoying Florida’s outdoor lifestyle. Sold fully furnished and professionally decorated, the home is ready for immediate use or rental income generation. Interior features include upscale finishes, an in-unit washer and dryer, high-speed internet, and flat-screen TVs throughout the property, ensuring a premium experience for guests. Magic Village Yards offers resort-style amenities, including 24-hour gated security, concierge services, a clubhouse, heated swimming pool and spa, fitness center, on-site restaurant, housekeeping services, and professional property management options. Its prime location places the community just minutes from Disney parks, major attractions, shopping, dining, and entertainment, with convenient access to major highways and Orlando International Airport. With strong year-round demand for short-term rentals, this property represents an excellent opportunity for investors seeking high occupancy potential in an established vacation rental market, as well as for buyers looking for a luxurious second home near Orlando’s world-famous attractions.

3065 Rockefeller Way, Kissimmee
$698,000
6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 7 SubDv. ⋅ 34747 Zip Code
Welcome to your ultimate vacation retreat, ideally located just 5 miles from Walt Disney World in the highly sought-after Windsor Hills Resort! This beautifully maintained 6-bedroom, 4-bathroom pool home offers the perfect combination of comfort, entertainment, and resort-style living, making it an excellent choice as a second home or high-performing short-term rental investment. The property has been meticulously cared for and features numerous significant upgrades, including luxury vinyl plank flooring throughout (2022), upstairs A/C (2020), downstairs A/C (2022), pool heater (2021), pool motor/pump (2023), pool safety fence (2023), and dishwasher (2026). The home also features a durable tile roof, offering added longevity and value. The main level includes a bedroom and full bathroom, ideal for guests or multi-generational living. Upstairs, you'll find two spacious suites plus three themed guest bedrooms, providing plenty of room for family and vacation guests. The garage has been converted into a fun-filled game room, creating additional entertainment space for all ages. Step outside to your private screened-in pool, the perfect place to relax and enjoy the Florida sunshine. The HOA fee includes lawn service, daily valet trash pickup, internet, and basic cable. Windsor Hills offers outstanding resort amenities, including 24/7 manned gated entry, a resort-style clubhouse and community pool, sports courts, putting green, and more. Conveniently located just minutes from Disney theme parks, major Central Florida attractions, dining, shopping, championship golf courses, airports, and Florida's famous beaches, this is an exceptional opportunity to own a turn-key vacation home in one of Central Florida's most desirable resort communities.

2536 Holtrock Street, Kissimmee
$299,900
3 Beds ⋅ 2 Baths ⋅ Oakwater Condo Ph 11-14 SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bathroom fully furnished condo located in the desirable gated Oakwater community, just minutes from Walt Disney World and Central Florida’s most popular attractions. Whether you're searching for a primary residence, second home, or investment opportunity, this inviting condo offers the perfect combination of comfort, convenience, and location. Inside, you’ll find a bright and spacious open-concept living and dining area, a well-equipped kitchen with generous cabinet and counter space, and comfortable bedrooms with plenty of room to unwind. One of the highlights of the home is the private screened balcony overlooking lush tropical landscaping, creating the perfect setting for morning coffee or relaxing in the Florida sunshine. Oakwater offers an impressive collection of resort-style amenities, including a gated entrance, community pool, clubhouse, fitness center, tennis courts, and playground. With shopping, dining, major roadways, and world-famous attractions just minutes away, this condo offers an incredible opportunity to enjoy the best of the Central Florida lifestyle.

2742 Oakwater Drive Unit 104, Kissimmee
$655,000
8 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2b SubDv. ⋅ 34747 Zip Code
Imagine pulling into a community where every day feels like you're on vacation. Located in the 24/7 guard-gated community of Windsor at Westside, this sprawling 8-bedroom, 6-bathroom home spans over 4,000 square feet of space designed for bringing loved ones together. Best of all, it comes fully furnished and turnkey, making it completely move-in or rental-ready from day one. Whether you are looking for a short-term rental investment or a primary residence where family and friends can spread out, this property delivers comfort, luxury, and convenience. From the moment you walk through the front door, the open-concept layout feels welcoming and effortless. The main floor features durable tile flooring throughout the main living areas, centered around a kitchen with rich cabinetry, stone countertops, and a large island where everyone naturally gathers. Just off the main space, slide open the glass doors to your private, screened outdoor oasis, featuring a crystal-clear pool, relaxing spa, and covered brick-paver lanai perfect for outdoor dining and evening relaxation. Thoughtful main-floor planning sets this home apart. The main level includes a private primary bedroom suite, as well as a second full bedroom and guest bathroom—ideal for guests who prefer to avoid stairs or for multi-generational living arrangements. Upstairs and across all bedrooms, you will find newly updated low-maintenance LVP flooring. For added entertainment, the full garage game room comes ready for fun with billiards and air hockey. Beyond the home, the neighborhood offers a complete resort lifestyle. The community amenities include a zero-entry pool with a water slide, lazy river, clubhouse, fitness center, bar and lounge, convenience store, tennis courts, playground, private rentable cabanas and more. The HOA fee simplifies daily living by covering high-speed internet, cable TV, daily trash pick-up, and full lawn maintenance. The location places you close to Central Florida's top attractions. You are approximately 25 minutes from Walt Disney World, minutes from shopping and dining at Posner Park, and close to the dining, shopping, and entertainment options at the Promenade at Sunset Walk, as well as nearby championship golf at ChampionsGate and major roadways like I-4 and US-27. Opportunities like this don't wait long—reach out now to claim your piece of Central Florida resort living today!

1610 Lima Avenue, Kissimmee
$315,000
2 Beds ⋅ 3 Baths ⋅ Margaritaville, Rolling Oaks SubDv. ⋅ 34747 Zip Code
Welcome to paradise at 8201 Surf St, a beautifully appointed, fully furnished 2-bedroom, 2.5-bathroom townhome offering the ultimate turn-key resort lifestyle. Nestled in the heart of the world-class Margaritaville Resort Orlando, this property boasts a prime location on the same street as the signature cottages and stands as one of the closest units to the main hotel building and its sprawling resort-style pool complex. Step inside to an inviting, open-concept floor plan filled with tropical charm and modern finishes, seamlessly extending out to a private patio area perfect for enjoying warm Florida sunshine, morning coffee, or evening relaxation. Positioned for exceptional investment potential, this home generated $45,587.00 in rental revenue for 2025, making it a proven performer for savvy real estate investors or buyers seeking an income-producing personal vacation getaway. Owners and guests enjoy top-tier resort amenities, including the zero-entry pools at Fins Up Beach Club, the tranquil St. Somewhere Spa, poolside dining at Salty Rim Bar & Grill, a state-of-the-art fitness center, and access to the adjacent Promenade at Sunset Walk and Island H2O Water Park. Located just minutes from Walt Disney World, Universal Orlando, premier shopping, and world-class dining, this move-in-ready property delivers effortless island living and lucrative return potential in Central Florida’s premier destination.

8201 Surf Street, 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
$560,000
6 Beds ⋅ 5 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
THE SELLER IS VERY MOTIVATED TO SELL!!!! Exceptional Vacation Home in Solara Resort – Private Pool, Short-Term Rental Approved & Minutes from Walt Disney World®! Welcome to this stunning fully furnished vacation home located in the highly sought-after Solara Resort, one of Central Florida's premier resort communities for short-term rentals. Whether you're looking for a profitable investment property, a vacation retreat, or a second home, this property offers the perfect combination of luxury, comfort, and location. From the moment you arrive, you'll be welcomed by a charming covered front porch and an inviting entryway leading into a bright, open-concept living area. Large sliding glass doors fill the home with natural light and open to a covered lanai overlooking the private screened-in pool, creating the perfect indoor-outdoor living space for relaxing or entertaining. The spacious kitchen is designed for both functionality and style, featuring solid wood cabinetry, a large breakfast bar, generous counter space, and a full set of appliances, making meal preparation effortless. This beautiful home offers 6 spacious bedrooms, 4 full bathrooms, and 1 half bath, plus a versatile upstairs loft ideal as a second family room or game area. The primary suite is conveniently located on the first floor and features a large walk-in closet and an elegant en-suite bathroom with dual vanities and plenty of space. Several bedrooms are professionally decorated with themed designs, creating an unforgettable experience for guests of all ages. The home also includes a 1-car garage. As part of the renowned Solara Resort, owners and guests enjoy access to world-class resort amenities, including a spectacular resort-style pool, FlowRider® surf simulator, clubhouse, fitness center, restaurant and poolside bar, splash pad, water slides, sports simulator, basketball court, beach volleyball court, soccer field, playground, game room, walking areas, and a gated entrance with resort-style security. Ideally located just minutes from Walt Disney World® Resort, Disney's Animal Kingdom, shopping, restaurants, golf courses, major highways, Island H2O Water Park, Sunset Walk, and other world-famous Orlando attractions, this home offers exceptional convenience for both owners and vacation guests. Don't miss this incredible opportunity to own a high-demand vacation home in one of Kissimmee's most desirable resort communities. Schedule your private showing today!

9012 Egret Mills Terrace, Kissimmee
$740,000
4 Beds ⋅ 3 Baths ⋅ Celebration South Village Unit 4 Rep 2 SubDv. ⋅ 34747 Zip Code
Welcome to 1425 Resolute Street, a beautifully designed David Weekley "Alameda" home nestled along the tree-lined streets of Spring Lake in Celebration. Charming Craftsman-inspired details and a picturesque covered front porch create an inviting first impression, while inside, a bright and spacious open floor plan was designed for comfortable everyday living and effortless entertaining. Beautiful wood flooring, crown molding, recessed lighting, updated fixtures, ceiling fans, and Hunter Douglas window treatments add warmth and character throughout. The kitchen is truly the heart of the home, featuring light cabinetry with glass-front accents and a built-in wine rack, granite countertops, stainless steel appliances, undermount sinks, a closet pantry, and a generous center island with additional storage and breakfast-bar seating. Open to the dining and family rooms, this welcoming space makes it easy to gather with family and friends. Wood stairs lead to the second floor, where you'll find three generously sized secondary bedrooms and a versatile loft featuring beautiful wood flooring. Ideal for today's flexible lifestyles, the loft offers wonderful additional living space for a home office, media room, playroom, or reading retreat. The oversized primary suite is filled with natural light and offers plenty of room for substantial furnishings plus a sitting area, reading nook, or workspace. The spacious primary bath features dual sinks, a garden tub, and separate shower. A large laundry room with tile flooring and additional storage adds everyday convenience. Built by David Weekley Homes, the residence also incorporates energy-efficient building features designed to enhance comfort and help reduce heating and cooling demands. Spring Lake residents enjoy their own neighborhood pool, fitness center, parks, green spaces, and access to Celebration's extensive network of scenic walking and biking trails. Follow the trails toward downtown Celebration, where lakeside views, restaurants, shops, community events, and charming Market Street create the distinctive small-town atmosphere Celebration is known for. Throughout the community, picturesque lakes, neighborhood parks, playgrounds, recreation facilities, and miles of trails offer endless opportunities to enjoy the Florida lifestyle. Spring Lake's convenient location near World Drive and I-4 also provides easy access to Walt Disney World Resort, Orlando's world-famous attractions, shopping, dining, entertainment, and major employment centers. AdventHealth Celebration and everyday conveniences are also nearby. With its welcoming front porch, spacious and flexible floor plan, beautiful interior details, energy-efficient construction, and wonderful Spring Lake location, 1425 Resolute Street is ready to welcome you home to the Celebration lifestyle.

1425 Resolute Street, Celebration
$648,000
7 Beds ⋅ 7 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Step into your next high-performing investment at 1633 Nassau Point Trail! This breathtaking, fully furnished 7-bedroom, 6.5-bathroom retreat in the premier gated Solara Resort is a proven revenue generator built for ultimate guest satisfaction. Perfectly positioned just steps from the clubhouse and adjacent to convenient extra guest parking, this turnkey powerhouse delivers high-yield performance alongside effortless vacation living. Guests can cool off in the private screened-in pool and spa, catch the big game on multiple outdoor TV setups, or unwind in the air-conditioned, tiki-themed garage lounge—a massive hit for both adults and teens. Inside, custom hand-painted murals and immersive themed bedrooms elevate the guest experience, driving stellar reviews and consistent bookings. The numbers speak for themselves: this top-performing property boasts an impressive 70% overall occupancy rate over the last 12 months, surging to an incredible 82% occupancy so far in 2026. For savvy investors or vacation home buyers, Solara Resort offers unmatched marketing power, attracting global travelers directly and through travel agency networks, as well as major booking platforms. The resort itself is a major draw, featuring world-class amenities, including the famous FlowRider® surf simulator, a zero-entry pool, a splash pad, a fitness center, a bar and grill, and sports courts. Located just minutes from Orlando’s world-renowned theme parks, premier dining, and top shopping destinations, this income-generating asset is completely plug-and-play and ready to start delivering returns from day one.

1633 Nassau Point Trail, Kissimmee
$875,000
4 Beds ⋅ 4 Baths ⋅ Celebration Area 5 SubDv. ⋅ 34747 Zip Code
First floor primary bedroom plus upstairs ensuite in desirable Artisan Park. This charming 4-bedroom, 3.5-bath Coastal-style with 2,587 square feet of living space, this home features double front porches and a floor plan designed for comfortable everyday living. The primary suite is conveniently located downstairs, while three additional bedrooms are upstairs, including one with a private bathroom. As you enter the home, you're greeted by a separate dining room and living room, creating a welcoming and traditional entry space. As you continue toward the back of the home, the layout opens into the kitchen and family room, creating a comfortable gathering space for everyday living. The backyard patio provides a great spot for outdoor dining and entertaining, or simply relaxing and enjoying the Florida weather. The home also features fully owned solar panels and a new roof was installed in 2022. Residents of Artisan Park have exclusive access to the private clubhouse, featuring a restaurant and bar, fitness center, and resort-style pool, along with a variety of social events held throughout the month.

1114 Tapestry Drive, Celebration
$450,000
4 Beds ⋅ 3 Baths ⋅ Lindfields Unit 4 SubDv. ⋅ 34747 Zip Code
Welcome to 2791 Picadilly Circle, Kissimmee, FL — a beautifully updated 4-bedroom, 2.5-bath pool home offering the perfect combination of modern upgrades, generous living space, privacy, and the Florida lifestyle. From the moment you step inside, you’ll appreciate the bright, open floor plan and thoughtfully upgraded interior. At the heart of the home is the updated gourmet kitchen, designed to impress with stylish finishes and an inviting layout perfect for everything from everyday meals to entertaining family and friends. The bathrooms have also been tastefully updated and upgraded, giving the home a fresh, modern feel throughout. With four spacious bedrooms and 2.5 baths, there’s plenty of room to spread out. The versatile living areas provide flexibility for entertaining, working from home, family gatherings, or simply relaxing at the end of the day. Step outside and discover your own private Florida retreat. The fully fenced backyard features a sparkling swimming pool and plenty of space to relax, entertain, barbecue, or soak up the Florida sunshine. Whether hosting weekend gatherings or enjoying a quiet afternoon poolside, this outdoor space is designed to be enjoyed year-round. Conveniently located in the heart of Kissimmee, 2791 Picadilly Circle puts you just minutes from shopping, dining, schools, major roadways, Orlando-area attractions, and everything Central Florida has to offer. Updated gourmet kitchen. Upgraded bathrooms. Four spacious bedrooms. Private fenced backyard. Sparkling pool. Prime Kissimmee location. This home checks all the boxes and is ready for its next owner. Schedule your private showing today and experience everything 2791 Picadilly Circle has to offer!

2791 Picadilly Circle, Kissimmee
$679,000
5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 06 SubDv. ⋅ 34747 Zip Code
This well-maintained 5 bedroom, 5 bath home in the 5-Star Windsor Hills Resort offers buyers a rare opportunity to acquire a proven, income-producing short-term rental just minutes from Walt Disney World—one of the strongest and most reliable vacation-rental corridors in the United States. Designed with the resort’s most desirable 5-bedroom open floorplan, the home consistently attracts large families and multi-generational groups, maximizing both occupancy and nightly rate potential. For buyers seeking immediate continuity of income, the seller is willing to transfer future bookings, allowing a seamless transition with no downtime. Interior Features for High-Demand Guest Use Multiple dining areas and a spacious main living room built to accommodate high guest volume Stainless steel appliances in the kitchen Two ground floor ensuites plus an additional twin bedroom—ideal for multi-family bookings Two junior suites upstairs, each with a private bath, supporting strong guest satisfaction and repeat stays Converted garage game room with foosball and pool tables—an amenity that significantly boosts rental performance Outdoor & Resort Amenities The screened lanai features a private heated pool, a top-performing feature for year-round bookings. Windsor Hills remains one of Central Florida’s top-performing vacation rental communities, offering: Lagoon-style resort pool Clubhouse, fitness center, and marketplace Tennis, racquetball, basketball, and volleyball Theater, arcade, playgrounds, and putting greens 24-hour guarded security Its unmatched proximity to Disney drives consistent occupancy, premium nightly rates, and strong year-round demand. Investment Highlights This property represents a rare chance to acquire a low-maintenance, high-demand, income-generating asset in one of the region’s most reliable STR markets. Windsor Hills is a purpose-built resort community offering amenities for all ages while remaining less than five minutes from Walt Disney World—making it an ideal choice for families and groups seeking affordable luxury in a prime location.

7777 Teascone Boulevard, Kissimmee
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