Kissimmee Single Family Homes For Sale - 2020 homes

Remarks: EXTENSIVELY AND BEAUTIFULLY REMODELED! Step into this fully furnished 4-bedroom pool home and experience the perfect blend of modern luxury and Florida living. Situated on a 0.23-acre lot with no HOA, this home has been completely renovated from top to bottom, featuring soaring cathedral ceilings, a brand-new chef-inspired kitchen, state-of-the-art bathrooms, and updated flooring throughout. Major systems, including the roof, HVAC, and water heater, have been upgraded for added peace of mind. Outside, enjoy your private pool and expansive deck, perfect for relaxing or entertaining under the Florida sun. Ideally located just minutes from top schools, parks, shopping, and dining, this home delivers the perfect combination of location, comfort, and long-term value. Don’t miss this rare opportunity, schedule your visit today!

Listing is courtesy of: EXP REALTY LLC (407-706-5000)

Listing Agent: Daniel Betancourt (407-375-9142)

Remarks: Under contract-accepting backup offers. Short Sale. Bank-Approved Short Sale – Price Approved! Single-story 3BR/2BA home in Poinciana with Spanish-style details and a comfortable layout. Fully fenced backyard and 2-car garage with washer/dryer space. Conveniently close to shopping, restaurants, schools, medical centers, golf, and more. Includes solar panels – buyer responsible for paying off or refinancing the balance prior to or at closing. Bank-approved at the listed price – move-in ready and well-maintained!

Listing is courtesy of: EXP REALTY LLC (407-674-7777)

Listing Agent: Walter Parraga (407-764-0245)

Remarks: Welcome to this beautiful 3-bedroom, 2-bathroom pool home located in the heart of Kissimmee! This well-maintained property offers a spacious and functional layout perfect for families, first-time buyers, or investors. Enjoy Florida living at its finest with your own private screened-in pool, ideal for relaxing weekends, entertaining guests, or soaking up the sunshine year-round. The home features an open living and dining area filled with natural light, a comfortable primary suite with private bath, and generously sized secondary bedrooms. The backyard provides privacy and plenty of space to enjoy outdoor living. Conveniently located near shopping, schools, restaurants, medical facilities, and major roadways for easy access to Orlando and theme parks. Don’t miss this opportunity to own a pool home in a prime location!

Listing is courtesy of: DEAL MAKERS REALTY TEAM CORP (407-288-0260)

Listing Agent: Maria Pagan (407-288-0260)

Remarks: Short Sale. Short sale, Bank approved price. Welcome to this charming two-story home in Kissimmee FL. Featuring two master suites one on the main floor and another upstairs each with updated private bathrooms. Two additional bedrooms share a beautifully updated third bathroom. Downstairs, the open-concept layout connects the kitchen, dining, and family room, creating an ideal space for everyday living. Enjoy cozy evenings by the fireplace or cook with ease in the well-appointed kitchen that overlooks the main living areas. Step outside to a spacious, fully fenced backyard, perfect for pets, play, or weekend gatherings. Recent upgrades include a new roof (2022) and A/C system (2019). Community amenities include Lake Marion Community Park, basketball court, and sports field, free cable, fitness center, meeting rooms, & community pool. Close to Disney, shopping, and dining, this home is perfect for you. There is a 15,000-dollar US Federal Bankruptcy Estate Fee to be paid by the buyer at closing.

Listing is courtesy of: CENTURY 21 CARIOTI (407-770-0322)

Listing Agent: Kavita Uttamchandani (239-691-2289)

Remarks: This is the listing with the most value for your money! Compare this home to all other active listings in this zip code and you'll see why. Charming 3-Bed, 2-Bath Home in the Heart of Kissimmee with NO HOA FEES. Beautifully maintained home with 3 bedrooms, 2 bathrooms, and unbeatable solid bones. With a roof, electrical, and plumbing system all updated just 2 years ago, this property is move-in ready and built to last and guaranteed to hit all your checkmarks. Nestled in the heart of Kissimmee (34743), this home offers unparalleled convenience. Located just 2 minutes from the Walmart Supercenter and steps away from the Turnpike North/South exit, you'll enjoy seamless access to major routes. The 417 Expressway is less than 5 minutes away, and Osceola Parkway leads you straight to The Loop shopping plaza, filled with restaurants and retail options. For entertainment lovers, Disney World and other world-class theme parks are just a quick 15-minute drive. Whether you're looking for a family home or an investment property, this gem combines comfort, location, and lifestyle. Don't miss your chance to own this Kissimmee treasure—schedule your showing today! IMPORTANT MESSAGE: NO SITE UNSEEN OFFERS.

Listing is courtesy of: LA REALTY SERVICES LLC (407-870-3519)

Listing Agent: Charles Maligaya (407-870-3519)

Remarks: STOP SCROLLING — THIS IS THE ONE. Welcome to 1665 Barberry Dr, Kissimmee, FL 34744, located in the sought-after Kindred Community! This massive 5-bedroom, 3-bathroom home offers 2,601 SQFT of beautifully designed living space — and here’s the rare bonus: Block construction on BOTH the first AND second floors for superior durability and strength! Open-concept layout perfect for entertaining - Spacious bedrooms for the whole family - Full bathroom & bedroom downstairs – ideal for guests or in-laws - Fully fenced backyard for privacy, pets & gatherings -Located in one of Kissimmee’s fastest-growing communities The Kindred Community offers incredible amenities including resort-style pool, fitness center, clubhouse, playgrounds & walking trails. Space. Strength. Location. Lifestyle. This home has it ALL. ?? Schedule your private showing before it’s gone!

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

Listing Agent: Kerlin Torre Wesson (407-686-0130)

Remarks: Under contract-accepting backup offers. Short Sale. SHORT SALE. BACK ON THE MARKET FINANCING FELL THROUGH. Send your highest and best offer. This one won't last long. Come see this incredible home located in the lovely Poinciana community. This gorgeous one-story, home features an open floor plan, 3 bedrooms and 2 baths complete with an array of upgrades such as energy-efficient appliances, countertops, beautiful wood cabinets, and attached 2 cars garage. Spacious Master bedroom and a large family room. Additional features include a covered lanai and front yard landscaping. This is a premier location with easy access to amenity-packed parks, sports courts, conservation areas and so much more. All information submitted on this property is intended to be accurate; however, it can't be guaranteed, buyers are advised to verify.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Oskar Murillo (407-460-3839)

Remarks: This charming updated home is move-in ready! NEW ROOF just completed 4/28. The welcoming front entry features an open porch. This is the perfect spot to sit and sip your morning coffee as you watch the sunrise. Open the front door, and enter the spacious living room, featuring a picture window and vaulted ceiling that flows directly into the tiled dining room. The space is great for entertaining. The updated kitchen has fresh white cabinets, and stainless steel appliances. The kitchen is open to the dining room. It features a bar where guests can sit and eat or simply use it as a buffet as you take meals at the dining table. Outdoor entertaining is easy as you pass through the sliding doors from the dining room to the outdoor space. The large screened in porch provides another great option for dining or simply another living space. Just add a comfy chair and curl up with a good book. The yard already has beautiful foliage, including flowering and fruit trees. If you enjoy gardening, this nice sized yard has plenty of potential! Back inside the home, you will find a split floor plan. The split plan provides privacy for the primary bedroom suite which includes a separate entrance and bathroom as well as a large walk-in closet. On the other side of the home, there are two additional bedrooms and a guest bath. The Sellers are in the process of putting on a new roof that will be completed prior to closing.This property is close to Central Florida attractions. Come see this sweet home today!

Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY (833-765-3244)

Listing Agent: Mary-Kim Shurina (407-580-6224)

Remarks: Nestled on a quiet cul de sac in the heart of Kissimmee, this inviting residence offers the perfect blend of comfort, convenience, and Florida lifestyle living. Surrounded by mature landscaping and a peaceful neighborhood setting, this home is ideal for those seeking a place to relax and recharge while remaining close to it all. Inside, the home offers a well designed layout filled with natural light and flexible living spaces perfect for everyday living or entertaining. It is a split plan with the primary suite on the opposite side of the house from the rest of the bedrooms which is great for privacy! The garage has been converted to an air conditioned bonus room which would make an amazing office or game room. Step outside and enjoy the outdoor space on your huge ½ acre lot. There is a large Florida room in the back with plexiglass windows that is perfect for enjoying your peaceful backyard view in any Florida weather. There is also a large open patio just outside of it that, perfect for morning coffee, weekend barbecues, or simply soaking up the Central Florida sunshine. The driveway is large enough to fit your boat or RV. Bring all the toys! There is a massive 24’x12’ workshop/storage shed with electricity in the backyard, too! This home has been completely replumbed and extra insulation has been blown into the attic throughout making it super efficient! The roof was replaced in 2018 and gutters were added to it and the shed. Laminate flooring was installed in 2020. The washer and dryer are included and have also been recently replaced. Whether you’re enjoying a quiet evening at home or hosting friends and family, this home adapts effortlessly to your lifestyle. If you’re looking for a home that combines tranquility, accessibility, and strong long term appeal, you found it! Call now to schedule a showing!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Eric Roman, Pa (407-342-5594)

Remarks: Under contract-accepting backup offers. Beautifully updated 4-bedroom, 2.5-bath home offering comfort, style, and plenty of space, conveniently located near Poinciana Parkway, the hospital, and Valencia College. Enjoy over 2,800 square feet of living space in this move-in-ready home that truly shows pride of ownership. The fully remodeled kitchen is designed to impress, featuring custom cherry cabinets, gorgeous granite countertops, a built-in oven and microwave, range hood, dishwasher, and a wonderful cooking range—perfect for any home chef. The spacious master suite provides a relaxing retreat with two walk-in closets and beautiful views, while the secondary bedrooms also enjoy peaceful scenery and generous space. Both the master and secondary bathrooms showcase elegant granite countertops for a touch of luxury. Major upgrades include newer windows, roof, A/C system, and hot water heater within the last 10 years, providing added peace of mind. Additional features include hurricane shutters, a water softener system, and a garage with a sliding screen enclosure for added comfort and versatility. Step outside to your screened-in patio and unwind while enjoying a tranquil water view—the perfect setting for relaxing evenings, entertaining guests, or simply enjoying Florida living at its best.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: One or more photo(s) has been virtually staged. SELLER MOTIVATED! Welcome to 2638 Eagle Canyon Drive N, a beautifully updated home in one of Kissimmee’s most desirable communities. From the moment you arrive, the pavered driveway and striking imported front door create a warm and stylish first impression. Inside, soaring cathedral ceilings and open living spaces are enhanced by upgraded light fixtures and modern finishes, giving the home a fresh and inviting feel. The kitchen and bathrooms have been thoughtfully updated to blend style and functionality, while the spacious primary suite offers hardwood flooring and a walk-in closet with a dedicated vanity and makeup area. Additional bedrooms feature cozy carpeting, creating comfort and charm throughout. The main living areas are finished with plank tile flooring, seamlessly tying together the formal and casual living spaces. Cooking is a delight with a gas range powered by a propane tank, and the large covered and screened porch provides the perfect space for relaxation and entertaining. The expansive fenced backyard is adorned with mature, fruit-bearing trees and includes a storage shed, offering both beauty and practicality. Solar panels are currently installed and may be negotiated with the sale or removed at the buyer’s preference. This home combines modern updates with everyday comfort in a prime location close to shopping, dining, and major highways.

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

Listing Agent: Steven Mason (813-863-3152)

Remarks: Step into comfort and style with this beautifully maintained 3-bedroom, 2-bath pool home that checks all the boxes. From the moment you arrive, you’ll notice the oversized brick-paver driveway and the cohesive paver design that wraps around the entire home, continuing seamlessly to the expansive pool deck—perfect for both everyday living and entertaining. Inside, the home features ceramic tile flooring throughout, offering a clean, modern look with easy maintenance—no carpet anywhere. The kitchen is a standout with granite countertops, solid wood cabinetry, and plenty of space for cooking and gathering. Step outside to your private backyard retreat, fully enclosed with a white vinyl privacy fence. The screened-in pool area provides the ideal setting to relax or host guests year-round, combining comfort with Florida outdoor living at its best. Whether you’re looking for a primary residence or a move-in-ready investment, this home offers a blend of quality finishes, thoughtful upgrades, and inviting indoor-outdoor living.

Listing is courtesy of: HONEST EXPERTS REAL ESTATE LLC (407-697-6611)

Listing Agent: Robert Kenon, Ii (407-697-6611)

Remarks: Discover modern Florida living in this nearly new, waterfront residence located in the desirable community of Sky Bend in Kissimmee. Built just one year ago, this expansive 5-bedroom, 3-bath home with a 2-car garage offers a thoughtfully designed floor plan ideal for growing families, multigenerational living, or long-term investment potential. The welcoming entry sets the tone with a bright foyer that flows seamlessly into the main living areas. A full bathroom and a first-floor bedroom provide flexibility for guests, a private home office, or a game room. The heart of the home features a modern kitchen, showcasing 42-inch white cabinetry, sleek quartz countertops, an elegant backsplash, and an oversized island perfect for entertaining. The open-concept design connects the kitchen to the dining area and the spacious living room, all overlooking the covered outdoor living space and water views. Upstairs, the primary suite serves as a private retreat, featuring a generous walk-in closet and a well-appointed bathroom with dual sinks and a walk-in shower. Three additional bedrooms, a full bath with a modern frameless glass shower, and a versatile loft-style family room complete the second level. The laundry room is conveniently located upstairs and adds everyday ease. Ceramic tile flooring enhances durability and style throughout the first floor, while plush carpeting provides comfort on the stairs and upper level. Outdoor living truly shines through four-panel sliding glass doors that open to a covered and screened enclosed porch, leading to a fully fenced backyard with tranquil pond views—an ideal setting for relaxation or entertaining. Residents of Sky Bend enjoy a low HOA fee and access to community amenities including a pool, playground, and green spaces, all just this just steps from Highway 192, shopping, dining, and major attractions. Combining space, modern design, energy efficiency, and an exceptional location, this home represents outstanding value. Schedule your private showing today and experience everything this exceptional waterfront property has to offer.

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

Listing Agent: Angela Garcera (601-214-3311)

Remarks: HUGE PRICE REDUCTION! Welcome to this inviting and well-maintained home located in the heart of Kissimmee. Offering a functional layout with spacious living areas, this property blends comfort, convenience, and everyday practicality. Natural light flows through the home, creating a warm and welcoming atmosphere perfect for both relaxing and entertaining. The generous backyard provides endless possibilities — ideal for gatherings, gardening, or creating your own outdoor retreat. With no HOA, you’ll enjoy flexibility and freedom rarely found in today’s market. Centrally located near shopping, dining, schools, and major highways, this home offers easy access to everything Kissimmee has to offer while still providing a sense of privacy and calm. Whether you’re a first-time buyer, growing household, or investor, this property represents a solid opportunity and a place ready to create new memories. Schedule your private showing today — homes like this don’t last.

Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)

Listing Agent: Paola Almonte (407-968-7511)

Remarks: **7 Bedrooms | 8.5 Bathrooms | Waterfront Living at Its Finest** ENJOY DISNEY MAGIC KINGDOM AND EPCOT FIREWORKS FROM THE TOP DECK. Welcome to your dream home on the lake! This stunning 7-bedroom, 8.5-bathroom house just hit the market and it's everything you've been looking for. Sitting right on the water, you'll enjoy gorgeous sunsets from your backyard every single evening. No hauling suitcases up the stairs here — this home comes with its own elevator! Three balconies give you plenty of outdoor space to relax, and one of the balconies even has a TV and overlooks the lake. Talk about the perfect spot to unwind. Inside, you'll find beautiful tile flooring throughout, quartz countertops, solid wood cabinets, and stainless steel appliances in the kitchen. Every bedroom is generously sized with a private bath, giving everyone plenty of room to spread out. The large game room with a wet bar with a pool table is ideal for entertaining guests. Step outside to your private pool and spa, where lakefront views make every swim feel like a vacation. The sunsets from this property are truly something special. Location is a huge bonus here. You're just minutes from Walt Disney World, Island H2O Waterpark, Sunset Walk, and plenty of shopping — including Target Grocery just down the road on Rolling Oaks Boulevard. Here's the best part — live here full-time as your forever home or rent it out on Airbnb for excellent rental income. Either way, this lakefront gem is a smart investment you don't want to miss!

Listing is courtesy of: LUXE PROPERTIES LLC (305-809-7650)

Listing Agent: Deanna Meredith (407-331-6542)

Remarks: Currently leased. Discover this beautiful new listing at 4432 Desert Rose Ave in the desirable Sedona community of Kissimmee, FL. This spacious 1,960 sq ft home offers four comfortable bedrooms, three stylish bathrooms, and an open floor plan that blends functionality with modern charm. The sleek kitchen features granite countertops and stainless steel appliances, while elegant light fixtures and ceiling fans add both comfort and character. The primary suite is a relaxing retreat with an extended walk-in closet for ample storage. A Tesla charging station is conveniently installed in the garage, perfect for electric vehicle owners. Ideally located near parks, shopping, and major highways, this move-in-ready home combines convenience, comfort, and a vibrant lifestyle—making it the perfect place to start your next chapter. Don’t miss your chance to make it yours!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: David Berlant (407-564-8950)

Remarks: Under contract-accepting backup offers. Welcome to this rare-to-find, fully furnished vacation villa in the sought-after Bella Vida Resort, just minutes from Disney! This home is not only beautifully designed but also a ready-to-operate short-term rental business — perfect for investors or families looking for a vacation home with great returns. Step inside and experience pure fun and comfort! The home features a Spider-Man arcade, an immersive Harry Potter movie theater, and themed bedrooms including Frozen, Star Wars, and Minions — delighting all aged alike. Enjoy the Florida sunshine in your private screened pool, or gather in the spacious open-concept living and dining area, ideal for entertaining family and guests. Whether you’re looking for a turnkey vacation home or a profitable short-term rental investment, this property checks every box — location, design, and income potential! Don’t miss this incredible opportunity — schedule your private showing today!

Listing is courtesy of: RC GROUP REALTY LLC (407-492-6778)

Listing Agent: Erika Gao (407-808-6966)

Remarks: Vacation living at its finest! Tucked behind the private gates of Wyndham Pointe, this turn-key, FULLY FURNISHED 2-story 7-bedroom, 6.5-bath pool home. The thoughtfully designed floor plan features impressive vaulted ceilings, tile flooring throughout, and an expansive open-concept living and kitchen area. The kitchen offers a breakfast bar, additional dining space, and stainless-steel appliances—perfect for entertaining. The home boasts two master suites (one on each level), two first-floor en-suite bedrooms, an upstairs en-suite, and two additional adjoining bedrooms with spacious bath, providing ample accommodations for guests or large families. French doors line the back of the home, opening to serene pool views and an extended lanai with a resort-style heated pool and spa, separate splash pad, outdoor shower, and convenient half bath. The two-car garage has been transformed into a home theater and billiard room, creating the ultimate entertainment space for family and friends to enjoy. ***UPGRADES include: ROOF (2023), HVAC (2025), and POOL PUMP (2024). *** Whether you’re seeking a primary residence, second home, or income-producing short-term rental, this property truly has it all!!!!! Located just minutes from Disney and Universal theme parks, H2O Water Park, premier dining, shopping, and entertainment, with easy access to SR 429 and the Florida Turnpike, offering quick routes to Central Florida beaches. Don’t miss this incredible opportunity!

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Erica Sadelfeld (407-427-0398)

Remarks: Welcome to 3549 Somerset Circle in Kissimmee—a beautifully furnished 4-bedroom, 3-bathroom waterfront pool home offering the perfect blend of comfort, style, and Florida living. This move-in-ready residence features brand-new flooring throughout, double-pane (double glass) windows for added efficiency and comfort, and a **new pool heater**, allowing you to enjoy the pool year-round. The home comes fully furnished, making it an excellent opportunity for buyers seeking a second home, vacation retreat, or turnkey investment property. The spacious, open-concept layout is ideal for both relaxing and entertaining, with large windows that fill the home with natural light. Step outside to your private backyard oasis, where stunning waterfront views create the perfect setting for peaceful mornings or sunset evenings. One of the standout features is the private boat dock, offering direct lake access for boating, fishing, or simply enjoying the tranquil surroundings. Located in the gated community of Bellalago, this home is just minutes from shopping, dining, and world-famous attractions like Walt Disney World. With its prime location, thoughtful upgrades, and fully furnished convenience, this property is a rare opportunity in Central Florida—especially for those looking for the perfect second home. Contact us for more information or to schedule your private showing.

Listing is courtesy of: KAT REALTY & PROPERTY MANAGEME (407-201-1712)

Listing Agent: Michiel Groenendijk (407-750-2669)

Remarks: RARE 9 BEDROOM ***Only 4 years Old. Luxury, Legacy and Lifestyle greet you at the private “Bears Den” gate at Reunion Resort. Once inside you will be met by this stunning 9 bedroom 8 ½ bath Reunion Resort Membership property that is equally inviting and LARGE enough to accommodate families with forever stays or maybe just a long weekend. The home is one of just a few in the exclusive community that is an exclusive corner lot. The home is being offered fully furnished including all GAMING SYSTEMS AND ARCADES. All the upgrades have been completed including theming, design extras, and enhanced gathering spaces. The LARGE open main level of the home entices everyone to discover more of what the property has to offer. Starting in the kitchen area you find dual refrigerators, and dual dishwashers behind a nicely appointed island accompanied by a large pantry. The living room seating can accommodate up to 12 and overlooks the massive back yard, pool, lounge, and exterior kitchen space through a wall of windows that let in the natural Florida Sunshine! Once outside notice the OVERSIZED patio space that not every home can offer. This is a game changer for the perfect pool day. The newly added putting green only enhances the outdoor time experience. This truly makes this home feel like its own resort. The first floor of the home also features a re-imagined garage space that will keep residents and guests alike busy for hours. No quarters needed! Upstairs you will find a custom loft area that is the focal point for families to gather and enjoy a comfortable and relaxing entertaining space. The theater/loft space is enough for 8 and marqueed by an 86-inch television. You will also discover the two additional themed rooms that are classics and translate to multiple generations. A home filled with extras, charm and endless memory making possibilities. HUGE RENTAL AND MEMORY MAKING POTENTIAL. Reunion Resort has everything you want in a community including 3 signature golf courses, world class dining, waterparks, lazy river, water slides, firework viewing areas, tree lined streets, dog park, playground, driving range, golf simulator, member events, in-resort shuttle service, and event space. Live the resort lifestyle like a VIP. NO OTHER RESORT IN THE AREA HAS THIS!!!! Minutes to Disney and close to Beaches, Universal, Legoland and Sea World. Schedule a tour today. 80 million visitors are estimated to visit Orlando in 2026. Current reservations for 2026 are available to convey to new owner when choosing to maintain relationship with current property manager.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Derrick Mnick (407-408-4676)