Kissimmee Homes with HOA Yes/No

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

$420,000

2 Beds ⋅ 2 Baths ⋅ Four Seasons At Orlando Ph 2 SubDv. ⋅ 34747 Zip Code

Welcome to the Four Seasons of Orlando's 55+ Community in Kissimmee, Florida just minutes from the Disney Theme Parks. This is a "Sandpiper" Villa with two bedrooms and two full baths plus a bonus room that can be an office or third bedroom. You will enjoy the spacious open concept living with sliders out to your own private heated pool. The caged lanai is extended with plenty of sunshine coming in. The Four Seasons is intertwined within Mystic Dunes Golf Course which makes for an interesting property lay-outs. We have a gate access over to the golf course and can enjoy lunch or dinner at the restaurant. You will also enjoy the two heated pools with a lap lane and hot tub. The clubhouse features a large ballroom, kitchen, game rooms, meeting rooms, gym and excercise room. Come join our community, it sure is a special place to live and minutes to the Disney Parks.

1896 Flora Pass Place, Kissimmee

$339,000

3 Beds ⋅ 2 Baths ⋅ Cypress Reserve Ph 02 SubDv. ⋅ 34741 Zip Code

Price to sell fast! Not a short sale or bank owned. Highest and best due by 5:00 pm August 23rd, 2026 Tucked inside the gated Cypress Reserve community, this home is truly move-in ready. The major items are already done: brand-new impact windows, a 2022 roof, and a 2020 A/C — so you can settle in and skip the projects. Inside, tall ceilings and natural light open up the living areas, making the whole home feel bigger than the square footage suggests. Granite countertops in the kitchen, a built-in desk nook that's perfect for working from home, and a two-car garage with a finished floor. Out back is where this one really shines. Double sliding glass doors open to a fully covered, screened-in porch with a ceiling fan — the kind of spot you'll use year-round, morning coffee through evening sunsets. It overlooks a large pond with open water views! Community amenities include a pool and maintained common grounds. Major roads, shopping, and dining are all just minutes away. Highest and best due by 5:00 pm August 23rd, 2026

2848 Oconnell Drive, Kissimmee

$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

$179,900

3 Beds ⋅ 2 Baths ⋅ Shadow Bay Villas Ph 06 SubDv. ⋅ 34741 Zip Code

EXCELLENT LOCATION AND NEIGHBORHOOD CLOSE TO LOOP SHOPPING MALL AND NEW DEVELOPMENT. 30 MINUTES FROM ALL CENTRAL FLORIDA'S MAJOR ATTRACTIONS, DISNEY WORLD, SEA WORLD, UNIVERSAL STUDIOS . NEW ROOF AND NEW TILES INSTALLED ONE YEAR AGO . WALKING DISTANCE TO ELEMENTARY SCHOOL AND MIDDLE SCHOOL.

2718 Rio Grande Trail Unit 2718, 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

$324,990

3 Beds ⋅ 3 Baths ⋅ Evergreen Park SubDv. ⋅ 34746 Zip Code

Under Construction. Evergreen Park presents the Pearson. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen, dining area and a living room overlooking a covered patio. The well-appointed kitchen features an island with bar seating, plentiful cabinets, counter space and stainless steel appliances, making entertaining a breeze. As we head upstairs, you are greeted with a landing area and linen closet. Bedroom one is located just off the landing area and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. This popular townhome features a single car garage at the front of the home. Like all homes in Evergreen Park, the Pearson includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1808 Bryant Street, Kissimmee

$275,000

3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 2 SubDv. ⋅ 34747 Zip Code

Fully Furnished First Floor Condo Near Disney! This beautifully maintained 3 bedroom, 2 bathroom FIRST FLOOR condo in the gated Wyndham Palms Resort Community offers exactly that lifestyle, with the added benefit of being FULLY FURNISHED and APPROVED for SHORT TERM RENTALS and AIRBNB. Whether you are searching for a vacation home, an income producing investment, or a primary residence close to the parks, this property is ready to deliver from day one. The open concept layout centers around a kitchen with STAINLESS STEEL APPLIANCES (2025), flowing easily into the living and dining spaces. NEW LUXURY VINYL PLANK FLOORING, FRESH PAINT, and REPLACED WINDOWS throughout give the home a clean, updated feel, while BRAND NEW LIVING ROOM FURNITURE means it is truly move in ready. The split bedroom design offers privacy for owners and guests alike, and a dedicated office space adds flexibility for remote work or managing your rental. Both bathrooms feature new shower doors for a fresh, modern touch. Imagine mornings on your private patio with coffee in hand, evenings by the resort pool, and easy access to Walt Disney World whenever the mood strikes. Step outside and you are directly across from the clubhouse, where residents enjoy 24 hour guard gated security, a resort style pool, splash pad, jacuzzi, sand volleyball, tennis and basketball courts, a movie theater, game room, and more. Location is everything here. You are minutes from Walt Disney World, Margaritaville Resort Orlando, Island H2O Water Park, Sunset Walk, Celebration, Old Town, championship golf, and Orlando International Airport, with quick access to US 192, SR 429, I 4, and Osceola Parkway. This is more than a condo. It is a chance to own a piece of the Central Florida lifestyle, fully turnkey and ready for you to enjoy

2307 Butterfly Palm Way Unit 104, Kissimmee

$324,990

3 Beds ⋅ 3 Baths ⋅ Evergreen Park SubDv. ⋅ 34746 Zip Code

Under Construction. Evergreen Park presents the Pearson. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen, dining area and a living room overlooking a covered patio. The well-appointed kitchen features an island with bar seating, plentiful cabinets, counter space and stainless steel appliances, making entertaining a breeze. As we head upstairs, you are greeted with a landing area and linen closet. Bedroom one is located just off the landing area and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. This popular townhome features a single car garage at the front of the home. Like all homes in Evergreen Park, the Pearson includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1804 Bryant Street, Kissimmee

$324,990

3 Beds ⋅ 3 Baths ⋅ Evergreen Park SubDv. ⋅ 34746 Zip Code

Under Construction. Evergreen Park presents the Pearson. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen, dining area and a living room overlooking a covered patio. The well-appointed kitchen features an island with bar seating, plentiful cabinets, counter space and stainless steel appliances, making entertaining a breeze. As we head upstairs, you are greeted with a landing area and linen closet. Bedroom one is located just off the landing area and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. This popular townhome features a single car garage at the front of the home. Like all homes in Evergreen Park, the Pearson includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1800 Bryant Street, Kissimmee

$331,990

3 Beds ⋅ 3 Baths ⋅ Evergreen Park SubDv. ⋅ 34746 Zip Code

Evergreen Park presents the Pearson. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen, dining area and a living room overlooking a covered patio. The well-appointed kitchen features an island with bar seating, plentiful cabinets, counter space and stainless steel appliances, making entertaining a breeze. As we head upstairs, you are greeted with a landing area and linen closet. Bedroom one is located just off the landing area and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. This popular townhome features a single car garage at the front of the home. Like all homes in Evergreen Park, the Pearson includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1795 Lindens Street, Kissimmee

$474,000

4 Beds ⋅ 3 Baths ⋅ Solivita Ph 5-A SubDv. ⋅ 34759 Zip Code

Virtually Staged. Like-New Calabria Model with Water & Conservation Views and Private In-Law Suite! Welcome to this beautifully maintained 2019 Calabria model featuring 4 bedrooms, 3 bathrooms, a private in-law suite with separate entry, and stunning water and conservation views on a . Ideally located just minutes from the Village Amenities Center, this home offers the perfect combination of comfort, privacy, and convenience. Enter through the screened-in front walkway, where you’ll find the private entrance to the in-law suite as well as the impressive leaded-glass front door. Inside, you’ll discover a spacious open-concept living, dining, and kitchen area designed to take full advantage of the beautiful water and conservation views. The large kitchen features a generous eat-at island/bar, abundant cabinetry with convenient pull-out drawers, beautiful quartz countertops, and a walk-in pantry. The adjoining dining area provides a wonderful view of the screened lanai, water, and conservation area. The spacious primary bedroom offers a tray ceiling, ceiling fan, and a peaceful private view of the water and conservation area. The luxurious primary bath features dual sinks, a large custom walk-in shower, and an enormous walk-in closet with enough room to feel like a small bedroom. Two additional guest bedrooms are located on the opposite side of the home, providing privacy for family or guests. These rooms can also easily be used as den, office, or flex spaces, with a conveniently located bathroom between them. The private in-law suite is accessed through its own separate entrance from the screened front walkway and includes a full bathroom, making it ideal for extended family, overnight guests, or a private retreat. Step outside to the screened and covered lanai, where you can relax and enjoy peaceful water and conservation views. It’s the perfect spot for morning coffee, entertaining, or simply enjoying the Florida lifestyle. The spacious two-car garage provides plenty of storage, along with a golf cart hookup and attic storage space. Additional benefits include windows, doors, and construction features designed to meet current hurricane-code standards, which will qualify the home for available new-home and hurricane-protection insurance discounts. The property is also NOT in a flood zone (Zone X). This exceptional Calabria model combines a desirable floor plan, private in-law suite, beautiful views, abundant storage, and a fantastic location near the Village Amenities Center. A must-see home that truly feels like new! The HOA provides exceptional value by covering landscaping maintenance, irrigation, cable TV, and high-speed Internet, allowing you to enjoy a low-maintenance lifestyle in this desirable community. Solivita is a premier 55+ community, offering residents an exceptional lifestyle with state-of-the-art amenities. Enjoy a fully 2 equipped fitness centers, dance and aerobics studios, and an impressive array of recreational options including 14 heated swimming pools, two heated spas, tennis courts, pickleball courts, shuffleboard, bocce ball, billiards, and an art gallery. The community also features three on-site restaurants and two championship 18-hole golf courses. With a full calendar of activities and events, there’s always something new to explore and enjoy. This home is conveniently located near a hospital and medical office complex, and shopping center.

163 Olympus Way, Kissimmee

Kissimmee Homes with HOA Yes/No

Newest Kissimmee Homes with HOA Yes/No