Kissimmee Single Family Homes For Sale - 2020 homes

Remarks: MOST SOUGHT AFTER FLOOR PLAN IN ALL OF MARGARITAVILLE RESORT ORLANDO! THESE RARELY COME UP AND THIS IS THE ONLY ONE OF IT'S KIND ON MARKET! Beautifully furnished corner-lot 1818-A cottage featuring 3 bedrooms and 3.5 bathrooms in one of Central Florida’s premier resort communities. Ideal as a full-time residence, second home, or income-producing vacation rental. Each bedroom offers a private EN-SUITE BATH with DUAL SINKS, providing comfort and privacy for owners and guests alike. The SPACIOUS second-floor loft creates an additional living area with access to a private balcony overlooking the lush tropical backyard and patio. The open-concept kitchen is appointed with upgraded appliances, quartz countertops, and an ISLAND with seating, flowing seamlessly into the bright dining area surrounded by windows. French doors from the living room lead to a charming paver patio and beautifully landscaped yard with winding sand and shell pathways through tropical foliage. Additional highlights include wood-look tile flooring throughout, ceiling fans in all rooms, side-by-side washer and dryer, and an upgraded TILE ROOF. Furniture and Housewares are included in the list price, along with blinds, drapery, TVs, artwork, kitchenware, dishware, linens, and décor. Located within the one-of-a-kind Margaritaville Resort Orlando with resort pools, fitness center, spa, water park, dining, shopping, entertainment, and the vibrant Promenade at Sunset Walk, all just minutes from Walt Disney World and Orlando’s top attractions. This is more than a home, it’s a vacation-inspired lifestyle where every day feels like a getaway.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: LOCATION, LOCATION! OPPORTUNITY! Amazing home at STOREY LAKE, with 5 bedrooms and 5 bathrooms, FULLY FURNISHED, with screen covered pool and heated spa. With an investment of $2500, the garage has been transformed in an amazing game room. This house stays 15 minutes from Disney's Parks, 10 minutes from Walmart, close to many restaurants, Outlets, and 30 min from the airport. INVESTORS, it has already many bookings for the next two months!

Listing is courtesy of: THE FLORIDA LOUNGE REALTY LLC (786-241-7619)

Listing Agent: Glauco Pochine (407-600-8766)

Remarks: BACK TO MARKET! MUST SELL! Palatial Estate on 35 Acres w/ Massive Warehouse & Development Approval! A once-in-a-lifetime offering! This is not just land; it's a magnificent 5-bedroom, 5.5-bathroom mansion situated on a massive 35 acre compound, complete with a commercial warehouse. Experience unparalleled luxury, privacy, and limitless potential. The Luxurious Residence: Boasting a commanding 5,044 sq ft under air, this home is designed for grand-scale living and entertaining. With 5 bedrooms and 5.5 bathrooms, it offers ample space for family and guests. Modern Comfort & Style: While details are to be discovered, homes of this caliber often feature gourmet kitchens, expansive living areas, home theaters, game rooms, and resort-style pools—all possible in this incredible setting. Ultimate Privacy & Legacy Living: Enjoy the rare combination of a luxurious, move-in ready estate with the privacy and scale of your own 35-acre kingdom. The Income & Development. Assets: Colossal Commercial Warehouse (~8,000 sq ft): A business owner's dream. This clear-span facility with high ceilings, phase power is perfect for any enterprise, storage, or as a world-class private workshop. Generate significant income or pursue your passion project. Unrivaled Scale & Flexibility: With 35 acres, the options are endless. Keep it as a legendary private compound, develop a portion, or build a mixed-use legacy project. Short-term rentals are approved for future builds. Prime Location & No HOA: Total freedom just minutes from Disney, major highways, and all Kissimmee amenities. The property is paved, fenced, and has multiple access points. This is more than a property; it's a legacy. A statement. A universe of possibilities. Contact us for a private showing of the estate and full development portfolio. Confidentiality assured. Currently use as Airbnb, all furnitures are included. Please schedule a showing with listing agent.

Listing is courtesy of: U KEY REALTY (407-937-8888)

Listing Agent: Yukey Hoo (407-937-8888)

Remarks: One or more photo(s) has been virtually staged. Spacious 4-Bedroom Retreat on a Quiet Cul-de-Sac – Your Kissimmee Dream Home Awaits! Welcome to 248 Cheshire Court, a beautifully maintained home nestled on a peaceful cul-de-sac in the heart of Kissimmee. This charming 4-bedroom, 2-bathroom property offers a spacious open layout with plenty of natural light, perfect for comfortable family living and entertaining. Enjoy a modern kitchen with ample cabinetry, a generous master suite with a private bath, and a large backyard — ideal for outdoor relaxation or weekend BBQs. Conveniently located near schools, shopping, dining, and major roadways for an easy commute to Orlando and nearby attractions. Don’t miss your chance to own this move-in-ready gem — schedule your private tour today! Photos are of a model home that is very similar. Not actual home.

Listing is courtesy of: TRANSCEND REALTY (407-518-7653)

Listing Agent: Jacob Hara (407-933-5478)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Seller relocating—bring your offers! Welcome to 2631 Captains Ct, a beautifully maintained 4-bedroom, 3.5-bath waterfront home tucked away on a quiet cul-de-sac in the highly desirable gated community of Bellalago. With a brand new tile roof (2023), private boat dock (2021), and sweeping lake views, this home is a standout for anyone seeking true Florida waterfront living. Step inside through updated double glass entry doors (2022) and you’re greeted by a bright, open layout that effortlessly blends formal and casual living spaces—perfect for both entertaining and everyday comfort. The chef’s kitchen features Samsung stainless steel appliances, quartz countertops, a large island with bar seating, a walk-in pantry, and ample cabinetry. The first-floor primary suite offers a private retreat with dual walk-in closets and a spa-like bathroom complete with double vanities, a soaking tub, and a tiled shower. A secondary bedroom with its own en-suite bath on the main level is ideal for guests or multi-generational living. Upstairs, you’ll find a spacious bonus/media room, two additional bedrooms, a full bath, and a convenient laundry chute—giving you flexibility for work, play, or hosting. Enjoy peaceful mornings and relaxing evenings on the covered, screened lanai overlooking the water. Additional updates include two new A/C units and a full exterior repaint (2025). The 3-car garage with built-in storage, extended paver driveway, and manicured landscaping add to the home’s strong curb appeal. Living in Bellalago means enjoying a true resort-style lifestyle along the shores of Lake Tohopekaliga, just about 21 miles from Walt Disney World. Residents have access to three pools, scenic walking trails, two fitness centers, a fishing pier, and an on-site restaurant, Flip Flops Restaurant. The community also features pickleball, tennis, basketball, beach volleyball, a kids’ water park, dog park, and picnic areas. Boating enthusiasts will appreciate the private boat launch and lift, offering direct access to Lake Toho. This is your opportunity to enjoy peaceful waterfront living with luxury amenities and everyday convenience. Schedule your private showing today and see why Bellalago continues to be one of Central Florida’s most sought-after communities.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: David Hartigan (407-955-1156)

Remarks: PRICE IMPROVEMENT. Welcome to this beautiful 2-story home in Stepping Stone, where you and your family will enjoy one of the best communities in Kissimmee. This home features 5 spacious bedrooms, 3 bathrooms, and a stunning lake view. This 5-year-new property is perfect for families, investors, or Disney enthusiasts. The first-floor features one bedroom, one bathroom, bonus/ flex room, living area, combined kitchen, and dining. On the second floor are the other four bedrooms, a small loft, laundry room, and two bathrooms. There is a community pool, playground, and walking trails. This home is in close proximity to Disney, shopping, and dining. It is a very peaceful and quiet place. You will feel like you are the only one living there because it's very quiet. This home has it all, plus beautiful views from both upstairs and downstairs of the lake. Home has a bonus- SOLAR PANELS. The only thing missing is YOU! What are you waiting for? Call for a showing today!!

Listing is courtesy of: PREMIUM PROPERTIES REAL ESTATE (407-380-2800)

Listing Agent: Carbeth Golding (407-729-9103)

Remarks: Discover this beautifully renovated home, perfect for living or investing, 2 Bedrooms | 1 Bath, Spacious Living & Dining Room. Brand-new kitchen with granite countertops, Fresh interior & exterior paint. Charming front & Back porch to enjoy your mornings. Elegant pavers! New metal roof! NO HOA! Prime opportunity in Kissimmee? Ideal for first-time buyers or investors. Schedule your private showing today! Wheel Chair Ramp, Dead-End. Community Allow 1 RV at the property!

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

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

Remarks: TURNKEY SHORT-TERM RENTAL with lucrative income record! RARE, PREMIUM Cul-de-Sac Gem: 3BR/2BA, 1,550 sq ft home in Reunion Village. Neighborhood amenities include 2 fabulous water parks, 3 championship golf courses, fitness centers, arcade game room, 7 pools, and 7 on-site restaurants. Your private Encore Club boasts world-class luxury resort amenities, including a spectacular 10-acre water park with thrilling water slides, a massive community pool with private cabanas, a state-of-the-art fitness center, tennis and basketball courts, and on-site dining options like Finns Restaurant and the Shark Lounge. Located just minutes from Walt Disney World, Universal Orlando, and SeaWorld, this property offers complimentary resort shuttle service to the major theme parks, plus seamless access to premier dining, championship golf, and endless shopping. This home sits on a premium, 6,057 sqf lot at the end of a private cul-de-sac with only two other neighbors and a yard that backs onto a protected conservation area—excellent for building your dream outdoor paradise. No rear neighbors, no thru-traffic, just pure relaxation. There is no yard work to worry about; landscaping and lawn care are done for you so you have time to enjoy the nearby activities. This upgraded home features quartz on all surfaces; white 42” kitchen cabinets; a beautiful island; walk-in pantry, GE kitchen appliances; and includes a washer and dryer. The property is fully furnished with HD TVs in every room, making it turn-key ready or available for immediate short-term rentals. Two of the backyard photos are staged, to show the potential of landscaping.

Listing is courtesy of: HOMECOIN.COM (888-400-2513)

Listing Agent: Jonathan Minerick (888-400-2513)

Remarks: This charming single-family home is in a peaceful neighborhood, perfect for those seeking a comfortable and inviting living space. This well-maintained residence features 3 bedrooms and 2 bathrooms, offering ample space for family and guests. The interior boasts a spacious open floor plan with plenty of natural light, creating a warm and welcoming atmosphere. The living and dining areas flow seamlessly, providing a versatile space for various activities. Outside, the property offers a well-manicured yard with a screened front porch to sit and relax and watch the morning sun rise. Located in Kissimmee, this home is conveniently situated near schools, shopping centers, parks, and other local attractions, providing a perfect blend of suburban tranquility and accessibility to urban amenities. Whether you are a growing family or someone looking to settle in a friendly community, 2419 Willow Tree Ln is a wonderful place to call home.

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Stephanie Florez (407-810-5874)

Remarks: 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: Turnkey and ready to move in! This 2023 single-family home sits on a quiet cul-de-sac in Poinciana, offering 3 bedrooms, 2 bathrooms, and 1,248 sq ft of living space on a 0.22-acre lot (9,736 sq ft / 905 sq m) with no rear neighbors. The open floor plan features a modern kitchen with stainless steel appliances, spacious living and dining areas, and a split layout for privacy. The primary suite includes a walk-in closet and private bath. Additional highlights include a 2-car garage with storage cabinets and leased solar panels for energy efficiency. The Poinciana HOA is just $90/month and covers Spectrum high-speed internet. Only about 30 minutes from Disney theme parks, with easy access to US-17/92, Poinciana Parkway, and I-4 for a convenient commute to Orlando, Kissimmee, and major attractions.

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

Listing Agent: Alexa Monasterio Flores (786-915-9294)

Remarks: Under contract-accepting backup offers. Welcome to Preserve at Tapestry, one of Kissimmee’s most sought-after communities, where lifestyle, location, and convenience come together. This beautifully maintained Somerset Model by Beazer Homes (2014) offers 4 bedrooms, 2.5 bathrooms, and 2,338 sq ft of thoughtfully designed living space—perfect for both everyday living and entertaining. From the moment you arrive, you’ll notice the attention to detail with a freshly painted exterior (2026), a newly painted and sealed paver driveway and entryway, and the added peace of mind of a brand-new roof (2026)—a major upgrade that adds both value and longevity. Step inside to an inviting open-concept floor plan featuring tile flooring throughout the entire first level, offering a clean, modern flow. The layout is both functional and versatile, highlighted by a separate formal dining room and a spacious living area that seamlessly connects to the kitchen. The kitchen is designed for both daily living and entertaining, featuring: Granite countertops Stainless steel appliances Ample cabinetry and storage Generous counter space for meal prep Side buffet area Large corner pantry Upstairs, you’ll find luxury plank wood vinyl flooring throughout, enhancing both durability and style. The second floor offers three well-sized secondary bedrooms and a full bath, while the owner’s suite is privately positioned in the corner for added comfort. The owner’s retreat features: Spacious layout Dual sink vanity Garden tub Separate walk-in shower And one of the standout features of this model: a HUGE walk-in closet, among the largest in Beazer’s floor plans Additional upgrades include an extra-large water heater, providing enhanced capacity and efficiency for a growing household. Step outside and start envisioning your future outdoor oasis. The backyard offers endless possibilities: Expand the existing covered lanai Design your own custom pool retreat Enjoy evenings around the existing fire pit Mature fruit trees and bamboo create a private and serene atmosphere Located just minutes from The Loop Shopping District, Walt Disney World, major restaurants and entertainment, as well as convenient access to Osceola Pkwy, SR 417, Florida’s Turnpike, and Orlando International Airport (MCO)—this home offers the perfect blend of accessibility and lifestyle. Residents of Preserve at Tapestry enjoy resort-style amenities, including a clubhouse, pool, walking trails, park and playground. This is a rare opportunity to own a move-in ready home with major upgrades already completed, in one of Kissimmee’s most desirable communities.

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

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

Remarks: Under contract-accepting backup offers. Fully remodeled and move-in ready! This beautiful 4 bedroom, 3 bathroom home features a private mother-in-law suite — perfect for extended family, guests, or rental income. The home has been completely updated with brand-new quartz countertops, modern shaker cabinets, and fully renovated bathrooms throughout, offering a fresh and contemporary feel. Enjoy an open and functional layout with stylish finishes, upgraded kitchen, and spacious living areas designed for comfort and convenience. The separate in-law suite provides flexibility and privacy, making this property ideal for multi-generational living or investment opportunities. Conveniently located near major highways, shopping, dining, and just a short drive to world-famous theme parks, Orlando International Airport, and top Central Florida attractions. Don’t miss this beautifully upgraded home in a prime Kissimmee location — schedule your showing today!

Listing is courtesy of: VITA LUXURY REALTY LLC (813-412-9468)

Listing Agent: Annay Hernandez (727-777-4222)

Remarks: MODEL HOME! Welcome to Hawks Run, a quiet St. Cloud community featuring a beautifully designed home inspired by the Noir Collection. This residence offers a covered patio, creating the perfect backdrop for relaxing mornings and evenings. Inside, the open-concept layout showcases quartz countertops, 42" kitchen cabinets, and luxury vinyl plank flooring throughout the main living areas, blending style with everyday functionality. Thoughtful finishes and natural light enhance the home’s warm, inviting feel. Conveniently located just 37 minutes from Orlando International Airport, 33 minutes from world-famous theme parks, and 30 minutes from Celebration, Hawks Run provides easy access to top destinations while remaining tucked away in a serene community served by great schools. This home delivers the ideal balance of comfort, convenience, and tranquil Florida living.

Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)

Listing Agent: Reed Williams (813-918-4491)

Remarks: Positioned on a canal-front lot in Kissimmee, this 3-bedroom, 2-bathroom home blends modern updates and waterfront living into one impressive package. From the moment you step inside, you’ll notice the abundance of natural light and open-concept layout designed for both everyday living and entertaining. The spacious living room centers around a stunning fireplace feature wall and flows seamlessly into the dining area and beautifully updated kitchen. The kitchen showcases white shaker cabinetry, stone countertops, stainless steel appliances, sleek modern fixtures, tile backsplash, and a wraparound bar-style counter with seating and built-in microwave storage. Oversized windows and glass doors throughout the home frame peaceful water views and create a bright, airy atmosphere. The primary suite offers spacious proportions and an updated ensuite bathroom featuring dual vanities, stone counters, and a large glass-enclosed walk-in shower. Additional bedrooms are generously sized and continue the home’s clean, modern aesthetic with consistent tile flooring throughout. Stepping outside, you’ll appreciate the oversized screened-in patio overlooking the backyard and canal — the perfect setup for relaxing, entertaining, or enjoying Florida outdoor living year-round. The property also features direct canal access with a private boat dock structure, offering endless potential for waterfront enjoyment. Situated on nearly a quarter-acre lot with mature trees and a 2-car garage, this property combines privacy, functionality, and location just minutes from shopping, dining, major roadways, golf, and Central Florida attractions including Disney. No HOA.

Listing is courtesy of: EXP REALTY LLC (407-846-0940)

Listing Agent: Steve Pugh (407-846-0940)

Remarks: The Crescent at Reunion Village is the perfect floor plan for residents seeking comfort and style in the place they call home! Three bedrooms, two bathrooms, great entertainment space and convenient access to resort amenities are what make this home a must-see. Continue reading to learn more about the space and features offered in this one-story retreat. The open-concept layout and wide-stretched entertainment space are what make the Crescent unique. Connected to the family room, the spacious kitchen features a walk-in pantry, stunning quartz countertops and a kitchen island. Plenty of natural light enters through the home’s many windows and through the sliding doors that lead to the covered patio, where outdoor entertainment awaits! All who enter will fall in love with the eye-catching details found in this dream home. As part of our CompleteHome Plus™ package, included features come with the home at no extra cost to you! Stainless steel Whirlpool® appliances, including the refrigerator, stove, microwave and dishwasher come installed and are ready for immediate use in the chef-ready kitchen.

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: $$$$$$ SELLER IS WILLING TO CONTRIBUITE WITH YOUR CLOSING COST $$$$$$$ Discover this beautifully maintained 3-bedroom, 2-bath residence situated on a premium fenced lot with no rear neighbors—the perfect blend of privacy and comfort. Nestled within a peaceful conservation area, this home offers exceptional outdoor space and serene views. Inside, you’ll find an upgraded kitchen with elegant cabinetry, modern flooring, and fresh interior paint that gives the home a move-in-ready appeal. The owner’s suite features a private bathroom and walk-in closet, while the additional bedrooms provide versatile space for family, guests, or a home office. Roof and A/C 2017, ensuring comfort and efficiency for years to come. The spacious two-car garage with its own exterior access and its large driveway adds convenience and functionality. Homes like this—offering space, upgrades, and location—are perfects for a first-time homebuyer or Investor. Don’t miss your chance! Schedule your private showing today before this opportunity is gone!

Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)

Listing Agent: Luis Perez (689-465-5870)

Remarks: Brand New Interior Paint--Move in Ready! Welcome to the beautifully maintained 3 Bedroom 2-Bathroom home located in the desirable gated community of Cypress Reserve! Featuring an open concept layout with wood flooring throughout, crown molding and window treatments! This home offers both style and comfort on a gorgeous, oversized lot! The kitchen is fully equipped with a refrigerator, dishwasher, oven and microwave and showcases Corian countertops, tiled backsplash, maple cabinetry, and a closet pantry. An eat-in area just off of the family room creates the perfect space for casual dining and everyday living. The spacious primary suite and secondary bedrooms offer a functional split floor plan. A 2023 AC and 2018 ROOF provides a peace of mind. Washer and dryer convey with the sale. Step outside and enjoy a large, enclosed lanai overlooking an expansive backyard--ideal for entertaining or relaxing year-round. Move in ready and conveniently located near shopping (The Loop), dining, and major roadways. Come and see this home today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Catherine Lambert Pa (407-908-2525)

Remarks: Under Construction. Kindred presents the Robie. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a nice sized living/foyer space to utilize for work or play. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Kindred, the Robie 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.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Stephen Cline (407-250-7299)

Remarks: Under contract-accepting backup offers. A rare opportunity part of historic Downtown Kissimmee with NO HOA. This charming well kept 2 bedroom 2 bath property is on a fully fenced lot with a huge extended Driveway that easily fits multiple vehicles meaning bring your boat, trailer, or work trucks with no restrictions. NO HOA! Great starter home that checks all the boxes. Roof was replaced in 2019 and air conditioning unit was replaced in 2025. Location is everything, and this one is unbeatable. Just a few blocks from Downtown Kissimmee, you’re minutes from Lake Toho's scenic waterfront, Kissimmee Lakefront Park, restaurants, Broadway Pizza, boutiques, the Kissimmee Valley Farmers Market, year-round community events, seasonal festivities, bus depot and Sun Rail access for easy commuting. Easy access to Disney, major roads and highways, the Turnpike and the hospital is just a few block away. Opportunities like this in Downtown Kissimmee don’t come around often so HURRY before it's gone!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Lucy Rivera (407-922-1953)