Kissimmee Homes For Sale & Real Estate - 3379 homes

Remarks: Under contract-accepting backup offers. Seller may consider buyer concessions if made in an offer ~ Welcome to opportunity in the GUARD GATED ~ RESORT COMMUNITY of Windsor at Westside – a FULLY FURNISHED ~ TURN KEY 5-bedroom, 4.5-bath PRIVATE POOL townhome that books well as a short-term rental and is ready to generate income from day one! Thoughtfully designed and tastefully decorated, this home feels light, bright, fresh, and truly move-in ready. TILE FLOORS flow throughout the main living areas, complemented by crown molding that elevates the OPEN CONCEPT living and dining spaces. The modern kitchen is both functional and stylish, featuring STAINLESS STEEL APPLIANCES, a tiled backsplash, ample cabinet and counter space, recessed lighting, pantry storage, and a large ISLAND with bar seating under pendant lighting – perfectly positioned to overlook the living and dining areas, making staying connected and entertaining effortless. A built-in drop zone at the foyer adds convenience for guests arriving and departing, while the covered front entry enhances curb appeal. The flexible floor plan includes a MAIN FLOOR BEDROOM & FULL BATH – ideal for multi-generational stays or guests who prefer first-floor accommodations. Upstairs, you will find the generous PRIMARY SUITE, a secondary en-suite bedroom with its own private bath, and additional well-appointed bedrooms and bathrooms designed with comfort and functionality in mind. Step outside to your COVERED PAVER LANAI and PRIVATE SCREENED POOL – a must-have for today’s vacation rental guests – complete with a convenient poolside half bath. Whether guests are soaking up the Florida sunshine poolside or floating the lazy river at the clubhouse, this property delivers the FULL RESORT EXPERIENCE. In addition to your private pool, Windsor at Westside offers a stunning community pool, clubhouse, fitness center, restaurant, game room, and one of the area’s most sought-after lazy rivers – amenities that consistently attract repeat bookings. The 1-car garage adds storage and owner convenience, while the LOW MAINTENANCE townhome lifestyle makes this an easy choice for investors or vacation home/second-home buyers alike. Located just minutes from world-famous theme parks, championship golf courses, premier shopping and dining, and with easy access to US-27 and 192, Windsor at Westside remains one of Kissimmee’s sought-after short-term rental communities. If you have been searching for a well-performing, fully furnished, income-producing vacation home in a true resort-style community – this is the one! Call today for more information and schedule a tour!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Short Sale. Short Sale. Third Party approval is needed. Take advantage of this incredible opportunity to own a 3-bedroom home offering immediate energy savings for the new owner. Located directly across from the community amenities, you’ll enjoy easy access to the resort-style pool, splash pad, playground, and beautiful water views just steps away. This home features great curb appeal with a two-car garage and paver patio. Inside, you’ll find a bright, open layout with tile flooring, neutral tones, and plenty of natural light. The kitchen offers shaker cabinets, stainless steel appliances, decorative backsplash, recessed lighting, a pantry closet, and a center island with bar seating, all overlooking the spacious living and dining areas. Sliding glass doors lead to a large backyard with a fire pit and convenient access to the community pool. The primary suite includes dual vanities, a walk-in closet, private water closet, and a glass-enclosed shower with floor-to-ceiling tile and rainfall shower head. The guest bathroom also features dual sinks and a private tub/shower combo. A dedicated laundry room with shelving and a GE washer and dryer adds convenience.Conveniently located off South Poinciana Blvd near Valencia College, Publix, Walmart, dining, and entertainment. With an improved price, paid-off solar, and a prime location, this home is ready for its next owner. Schedule your showing today.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Florentino Beltran (407-729-5577)

Remarks: Step into this stunning and beautifully furnished 5-bedroom, 4-bathroom townhome nestled within an exclusive resort-style community. Designed with comfort and style in mind, this spacious home offers a modern layout perfect for families. Enjoy your own private pool, ideal for relaxing afternoons or entertaining in the Florida sun. The community itself is rich with amenities, including clubhouse access, fitness facilities, resort-style pools, sports courts, playgrounds, and more—ensuring there’s something for everyone to enjoy. Don't miss out on this great opportunitiy! Tour this amazing property today!

Listing is courtesy of: GOLDEN KEY REAL ESTATE SOLUTIONS LLC (407-801-8283)

Listing Agent: Gleyson Silva (407-575-7332)

Remarks: Excellent investment opportunity. Located in the exclusive gated community of Compass Bay, one of the few communities in Kissimmee that permits short-term rentals (Airbnb/VRBO). The property is currently tenant-occupied, providing immediate rental income from day one. This well-maintained residence features 3 bedrooms, 2.5 bathrooms, and 1,882 square feet of living space, along with high-quality upgrades, including Luxury Vinyl Plank (LVP) flooring throughout with no carpet. The garage has been professionally converted into a fourth bedroom, complete with its own independent air-conditioning unit and upgraded flooring, offering a versatile space that can be used as a bedroom, home office, gym, or game room, while still retaining the option to function as a garage. Its prime location makes this property an outstanding investment, situated approximately 7–10 minutes from Walt Disney World, 15 minutes from SeaWorld Orlando, 18–22 minutes from Universal Orlando Resort, 8 minutes from The Loop Shopping Center, and 20–25 minutes from Orlando International Airport (MCO). It also offers convenient access to US-192, Osceola Parkway, and SR-417, providing easy connectivity to Central Florida's major attractions, shopping, dining, and entertainment. An ideal opportunity for investors seeking immediate cash flow, a property in a high-demand location for both tourists and residents, and the flexibility to continue as a long-term rental or potentially transition to the vacation rental market in the future, subject to community regulations and the terms of the existing lease

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Marjorie Mojica Paz (407-272-0179)

Remarks: Under contract-accepting backup offers. Welcome to your own private retreat in the heart of Poinciana! Located in the growing Polk County side of Poinciana, this spacious 2-story home at 2074 Rio Grande Canyon Loop offers the perfect combination of functionality, comfort, and outdoor living that is hard to find at this price point. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,154 square feet of living space, this home was designed with family living and entertaining in mind. The first floor offers a formal living room and formal dining room that are ideal for holidays, gatherings, and special occasions. The oversized kitchen provides abundant cabinet and counter space, a breakfast bar, and an additional dinette area, all overlooking the large family room to create an open and inviting atmosphere. A downstairs laundry room and convenient half bath complete the first floor layout. While the interior is in very good condition, the home also presents an excellent opportunity for the next owner to add their own modern touches and upgrades over time. To help make that transition even easier, the seller is willing to offer a flooring credit with a reasonable accepted offer so the new owner can personalize the flooring to their own taste and style. But the TRUE SHOWSTOPPER of this property is the incredible backyard oasis. Step outside and prepare to fall in love with a resort-style outdoor retreat featuring an estimated $70,000 custom pool and spa package designed for year-round Florida living. Whether you are entertaining guests or simply relaxing after a long day, this backyard was built to impress. The outdoor space includes a beautiful pergola, outdoor seating area, grilling station, electric fireplace, and even a pop-up TV — all of which convey with the property. This outdoor paradise creates the perfect setting for family gatherings, game days, weekend BBQs, or peaceful evenings under the stars. Additional upgrades and features include: Recently replaced AC system Pre-wire and electric capability for a generator Spacious floorplan with multiple living areas Large backyard entertainment space Pool and spa retreat perfect for Florida living This is more than just a house — it is an opportunity to own a home with incredible outdoor living potential, solid major upgrades already completed, and the ability to customize the interior to your own personal style.

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Alex Vazquez (407-270-6841)

Remarks: Located in the gated community of Cumbrian Lakes, close to shops restaurants and all Central Florida attractions, this house is in exceptional condition and has only been used exclusively as a vacation home by its owners from new. Upon entering through the double front doors, you'll be greeted by a bright and airy open-plan design, perfectly complemented by the TWO expansive patio doors that lead out to a spacious pool and deck with spa and pool bath, boasting one of the community's most coveted views. The split-bedroom layout provides added privacy; the generous master bedroom with pool access features an en-suite with dual vanities, a soaking tub and separate shower along with a walk in closet. Three additional bedrooms provide plenty of space for family, guests, or a home office. Recent upgrades include a new roof (October 2022), resurfaced pool, complete re-screen and deck painted (2023), as well as the replacement of the refrigerator and dishwasher within the last two years. The property also features a remote 5.1 surround sound system, extending onto the pool deck. Offered fully furnished, this turn-key property is ideal for short-term rental investment opportunities or as a luxurious retreat to call home. Don't miss this incredible opportunity and schedule your showing today.

Listing is courtesy of: SOUTH ORANGE PROPERTY & REAL ESTATE SERVICES INC (407-851-7002)

Listing Agent: Deborah Mansell (407-668-7918)

Remarks: Under contract-accepting backup offers. Property to be sold AS-Is only. Owner motivated.

Listing is courtesy of: KELLY RIGHT REAL ESTATE (813-321-2282)

Listing Agent: Mara Rodriguez (407-556-4315)

Remarks: Fully renovated 3 bed 2 bath home. The property has been tastefully renovated for comfort and a timeless appeal. The heart of the home is the delighful kitchen with granite work sufaces and stainless steel appliances giving the room a modern clean appearance.The bathrooms have also been updated. The property exterior itself has great curb appeal and will delight the most demanding buyer. The home is convenaintly located near to downtown Poinciana where you can choose various shops and restaurants to your own personal choice and will provide easy access to you and your familys needs. Seller financing available. Seller has active real estate license Listing Broker has financial interest in the property

Listing is courtesy of: CAVENDISH REALTY (407-791-8372)

Listing Agent: Lesley Price (407-791-8372)

Remarks: Welcome to your perfect Florida retreat! This attractively priced, two-bedroom, two-bathroom corner-unit condominium offers exceptional value and flexibility in a beautifully maintained gated community. Whether you're searching for a primary residence, a vacation getaway, or an investment opportunity, this property checks all the boxes. The community allows both short-term and long-term rentals, making it ideal for homeowners and investors alike. Step inside and discover a comfortable, inviting space designed to feel like a true home away from home. The desirable corner-unit location provides added privacy, abundant natural light, and a spacious feel throughout. For added convenience, the existing furnishings are negotiable, offering the potential for a seamless move-in or turnkey rental opportunity. Beyond your front door, you'll enjoy an impressive selection of community amenities, including a clubhouse, tennis courts, a sparkling community pool, and additional recreational features for residents and guests to enjoy. From the moment you enter this charming gated community, you'll be pleasantly surprised by its welcoming atmosphere, attractive surroundings, and resort-style appeal. Conveniently located near shopping, dining, golf courses, and Central Florida attractions, this condo offers the perfect combination of comfort, convenience, and investment potential. Don't miss this opportunity to own an affordable piece of paradise in one of Kissimmee's hidden gems. Schedule your private showing today and experience all that this wonderful community has to show!

Listing is courtesy of: CENTURY 21 ALL HOMES & PROPERT (407-343-1300)

Listing Agent: Kish Munjal (407-922-2100)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully FULLY FURNISHED 5-bedroom, 4 full bathroom, and 1 half bathroom townhouse located in the highly sought-after SOLARA RESORT. Designed with both comfort and style in mind, this spacious home features an open floor plan with a modern kitchen complete with a large island, stainless steel appliances, and seamless flow into the living and dining areas—perfect for entertaining. One of the most unique and desirable features of this property is its UNBEATABLE LOCATION DIRECTLY NEXT TO THE CLUB HOUSE—just steps away and significantly closer than most other units in the community, offering unmatched convenience for you and your guests. This highly desirable proximity is a major advantage for guest convenience and booking appeal, giving vacationers quick and easy access to all resort amenities without the need to drive or walk long distances—making it an exceptional choice for maximizing short-term rental demand and occupancy. The home is filled with natural light thanks to large sliding glass doors that lead to your PRIAVTE HEATED POOL, enclosed within a screened lanai for year-round enjoyment. The first-floor primary suite provides privacy and convenience, while upstairs you'll find a versatile loft area ideal for relaxation or additional entertainment space. Each bedroom is thoughtfully designed, including a fun and immersive Harry Potter–themed room and a charming Mickey Mouse–themed room, making this home especially appealing for vacation guests. The remaining bedrooms are tastefully and elegantly decorated, and the property is being sold fully furnished and turnkey. Located just minutes from Walt Disney World and other world-famous attractions, Solara Resort is a guard-gated, resort-style community offering exceptional amenities, including a grand clubhouse with a resort-style pool, FlowRider® SURF SIMULATOR, splash park, fitness center, poolside bar, retail options, and recreational courts for volleyball and basketball. With strong rental history and high occupancy potential, this property presents an outstanding opportunity for short-term rental investors or those seeking a vacation home with excellent income potential. Don’t miss your chance to own a prime-location property in one of Central Florida’s premier resort communities.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Hector Leon (407-227-4568)

Remarks: *NEW ROOF INSTALLED*Great location with convenient access to the Florida Turnpike, SR-417, and major roadways, and approximately 20 minutes from Disney and other popular attractions — all with NO HOA. This 3-bedroom, 2-bath home offers an open-concept living area plus an all-weather Florida room for flexible extra space. One bedroom features a private entrance and bathroom, ideal for guests or extended living arrangements. Enjoy a large fenced backyard with plenty of room for RV or boat parking. Major updates within the past two years include windows, HVAC system, ductwork, and plumbing. Move-in ready and seller motivated — a great opportunity in a highly convenient area.

Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)

Listing Agent: Neerupa Sahai (352-978-9165)

Remarks: Beautifull Home 3/2 close to schools Osceola County District, all floors ceramic tile, all pluming pipes was changed las year 2025, roof 2016, good for investment and primary buyers. The owner very motived, can rent with option to buy at expiration contract at year or before. close at shopping new shopping center Poinciana and Hospital, close at new express way Poinciana. The Hoa include cable and internet. Please send As Is Contract with pre-approval letter and proof of founds.

Listing is courtesy of: PROPERTY OUTLET INTERNATIONAL (407-723-7000)

Listing Agent: Jose Lozada (407-744-2904)

Remarks: Under contract-accepting backup offers. Turnkey, fully furnished 3-bedroom, 2.5-bathroom end-unit townhome in the gated Regal Oaks Resort community just minutes from Disney. This two-story property features an open-concept living and dining area on the first floor, with all bedrooms located upstairs. Tile and laminate flooring run throughout the entire home. The spacious primary suite offers a private ensuite bathroom and balcony. Enjoy relaxing water views from the screened private lanai. Regal Oaks offers resort-style amenities including a large community pool, water slide, clubhouse, game room, restaurant, and tiki bar. Conveniently located near Walt Disney World, major attractions, shopping, dining, and within walk distance to the popular Old Town entertainment district. Zoned for both short-term and long-term rentals, making it an excellent vacation home, income-producing investment property, or primary residence. Some furniture may have been updated. Room measurements are approximate. The buyer or buyer agent are responsible to verify dimensions, measurements, and Contact HOA to verify HOA fees, restrictions, access and all other information. The home is currently under contract but accept backup offer.

Listing is courtesy of: CORNERSTONE INTERNATIONAL PROPERTY GROUP LLC (407-334-7497)

Listing Agent: Helen Lei (407-371-1225)

Remarks: Under contract-accepting backup offers. Fully renovated 2-bedroom, 2-bathroom investment opportunity in the heart of Kissimmee with short-term rentals and Airbnb allowed. Prime location offering immediate income potential for investors, second-home buyers, or owner occupants seeking flexibility. This move-in-ready property features a brand new 2025 roof, updated flooring, a fully remodeled white designer kitchen with granite countertops, accent walls, contemporary lighting throughout the entire property, and beautifully updated bathrooms including a modern walk-in shower. Enjoy the enclosed screened porch along with a privately fenced and freshly paved backyard area, creating the perfect space for relaxing or entertaining guests. For those who choose to participate in the optional HOA, enjoy community amenities including a resort-style pool, tennis courts, basketball courts, and a playground. Conveniently located near Walt Disney World, SeaWorld, Universal Studios, ICON Park, the Orange County Convention Center, premium outlets, restaurants, shopping, and major highways, this prime location supports strong rental demand and long-term value. Whether you are expanding your investment portfolio or searching for a turnkey Florida vacation property near Orlando’s top attractions, this home checks all the boxes.

Listing is courtesy of: RE/MAX DOWNTOWN (407-770-2050)

Listing Agent: Jessie Nemeh (407-739-3661)

Remarks: Welcome to this beautifully renovated first-floor condo located in the desirable gated community of Kissimmee! This move-in ready unit features brand-new flooring throughout, fresh modern paint, and a bright open layout perfect for comfortable Florida living. Enjoy the convenience of a first-floor location with a private patio ideal for relaxing mornings or entertaining guests. The community offers a secure gated entrance and a great location close to shopping, dining, major highways, attractions, and everything Central Florida has to offer. Whether you are looking for a primary residence, vacation home, or investment opportunity, this condo is ready for its new family to call it home!

Listing is courtesy of: REAL ESTATE COMPASS, LLC (407-402-0232)

Listing Agent: Marilia Neri (407-952-7551)

Remarks: Under contract-accepting backup offers. Exquisite Lakefront Luxury Estate in Formosa Gardens on Star Lake Welcome to an extraordinary, turnkey Mediterranean estate perfectly positioned on the shores of Star Lake in the Formosa Gardens community. Just minutes from Walt Disney World, Universal Studios Florida, and SeaWorld Orlando, this remarkable residence offers the ultimate blend of luxury, comfort, and convenience. This custom-built, high performance vacation rental has been the center showcase for many stunning weddings and corporate retreats, is lavishly furnished home features 9 spacious bedrooms and 10 bathrooms, each bedroom designed as a private suite with its own beautifully appointed bath. From the moment you enter, you are greeted by a grand staircase and elegant architectural details that set the tone for this impressive estate—perfectly suited for luxury living, corporate retreats, or large family gatherings. At the heart of the home is a chef-inspired gourmet kitchen complete with a gas stove, granite countertops, and custom cabinetry, seamlessly flowing into expansive living and entertaining spaces. The home is thoughtfully equipped with high-end amenities including a baby grand piano, upgraded smart TVs, a private fitness area, arcade game, slate pool table, projection theater setup, and a dedicated wine room. Step outside to your private resort-style oasis where an infinity-edge pool appears to merge into the tranquil waters of Star Lake. The screened lanai and second-floor deck provide breathtaking, unobstructed views—perfect for enjoying Florida sunsets and even Disney fireworks in the distance. Outdoor living is elevated with a fully equipped summer kitchen, gas grill, bar area, and lounge spaces designed for entertaining day or night. With its unmatched location, exceptional design, and extensive amenities, this one-of-a-kind lakefront estate offers a rare opportunity to own a true Central Florida luxury retreat. Experience it in person—this is a home that must be seen to be fully appreciated

Listing is courtesy of: FLORIDA IN MOTION REALTY INC (407-947-2757)

Listing Agent: Eugene Petriella (321-299-8766)

Remarks: Welcome to this well-maintained Eastham II floor plan located in the gated community of Storey Lake. This 4-bedroom residence offers a functional split-bedroom layout with spacious living areas and multiple full bathrooms designed for privacy and convenience. The main living area features an open-concept kitchen, dining, and living room combination with abundant natural light. The kitchen includes professionally painted cabinetry with soft-close upgrades, stainless steel appliances, a custom pantry, granite countertops, and a large quartz center island with seating for up to 4 individuals. The adjacent dining area offers flexible use as a formal dining space, home office, or additional living area. The primary suite is privately positioned toward the rear of the home and features luxury vinyl flooring, a tray ceiling, walk-in closet, and an en-suite bathroom with dual vanities, garden tub, and separate walk-in shower. A secondary access point to the laundry room adds practical functionality. Outdoor features include a covered patio area overlooking a fenced backyard with no rear neighbors. The extended brick paver patio includes a motorized retractable awning and vertical screen, providing additional usable outdoor living space. Please note, there is no screened patio/enclosure. Additional features include a 2-car garage with ceiling-mounted storage, whole-house water filtration system, and HVAC updates, with the interior unit replaced in 2023 and exterior unit replaced in 2020. Storey Lake offers gated access and community amenities including a pool, fitness center, parks, and recreational areas. The property is conveniently located near major highways, shopping, dining, and Central Florida attractions.

Listing is courtesy of: NORKIS & CO REALTY (407-506-7070)

Listing Agent: Jose Santana Feliciano (407-760-9090)

Remarks: Welcome to 1229 Bermuda Lakes Lane, Unit 208, a spacious 2-bedroom, 2-bathroom condominium offering 1,103 square feet of comfortable living in the highly desirable Gables at Lakeside community. Whether you're searching for your first home, a seasonal retreat, or an excellent investment opportunity, this property offers the perfect combination of comfort, convenience, and value. Step inside to discover a bright, open floor plan with generous living and dining spaces designed for both everyday living and entertaining. The split-bedroom layout provides added privacy, while the spacious primary suite features its own private bathroom and ample closet space. A private balcony offers the perfect place to enjoy your morning coffee or unwind after a long day. Residents of The Gables at Lakeside enjoy an impressive selection of resort-style amenities, including a community pool, fitness center, clubhouse, tennis courts, basketball court, playground, walking paths, picnic and grilling areas, and beautifully maintained grounds. Ideally located in the heart of Kissimmee, you'll be just minutes from The Loop shopping district, restaurants, entertainment, major highways, Orlando International Airport, and Central Florida's world-famous attractions. Whether you're looking for a place to call home or a property with excellent rental potential, this condo checks all the boxes. Don't miss your opportunity to own in one of Kissimmee's most sought-after condominium communities—schedule your private showing today!

Listing is courtesy of: FLORIDA REAL ESTATE CENTER LLC (352-241-7000)

Listing Agent: Dj Wilson, Jr. (352-241-7000)

Remarks: Welcome to the Caladesi floor plan in the beautiful community of Poinciana, just minutes from the Orlando area This single-story home offers the perfect mix of modern style and everyday comfort with an open-concept layout that’s ideal for entertaining and relaxing. The kitchen is truly the heart of the home, featuring a stunning granite island, 36” upper cabinets with crown molding, brushed nickel hardware, USB outlets, and a full set of stainless steel Whirlpool appliances all included. The split-bedroom design gives you the privacy you need, with a spacious master suite that includes a large walk-in closet and private bathroom. Plus, you have two additional bedrooms and a second full bathroom, perfect for family, guests, or even a home office You’ll also love the added value with a landscaped front yard, WiFi-enabled garage door opener, and a spacious two-car garage. This home is move-in ready and comes with a structural warranty for peace of mind. Living in Poinciana means enjoying amazing amenities like a pool, sports courts, dog park, playground, and scenic walking trails With low to no down payment options, builder will assist closing costs, this is an incredible opportunity you don’t want to miss. Schedule your private tour today!

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Kennia Lozada Rivera (407-259-9096)

Remarks: Back on the market due to the previous buyers' backed out, at absolutely no fault of the sellers. This is your second chance to own this exceptional Next Gen® home. Experience refined, single-story living in this thoughtfully designed home that perfectly blends privacy, flexibility, and modern comfort. One of its standout features is the highly sought-after Next Gen® private apartment, ideal for multigenerational living, extended family, long-term guests, or a private home office. Complete with its own separate front entrance, living room, kitchenette, bedroom, and full bath, this private suite offers the perfect balance of independence while remaining connected to the main home. Inside the main residence, an open-concept layout seamlessly connects the kitchen, dining area, and family room, creating an inviting space for everyday living and entertaining. The kitchen features stainless steel appliances, abundant cabinetry, and generous counter space to accommodate any home chef. Privately situated at the rear of the home, the spacious owner's suite provides a peaceful retreat, while the additional bedrooms offer versatility for guests, a home office, or hobby space. The covered lanai overlooks a tranquil conservation area with **no rear neighbors**, providing exceptional privacy and a peaceful natural backdrop that is increasingly hard to find.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)