Kissimmee Single Family Homes For Sale - 2020 homes

Remarks: Welcome to 4261 Twilight Trail, a stunning custom-built estate nestled on 5 private acres in the heart of Kissimmee. This property was thoughtfully designed with comfort, quality, and style in mind, featuring numerous upgrades throughout the home. Enjoy the perfect balance of space and privacy while still being close to shopping, dining, schools, and major highways. With its open layout, modern finishes, and expansive outdoor space, this home is ideal for families, entertaining, or those who simply want to enjoy the beauty of Florida living.

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Ralph Carrion (407-572-1266)

Remarks: Under contract-accepting backup offers. Beautifully maintained home in the heart of Kissimmee featuring a roof replaced approximately 2 years ago, fresh exterior paint, new water heater, and new refrigerator with transferable 1-year warranty. Property also includes hurricane shutter panels for added convenience and peace of mind. Ideally located near supermarkets, shopping, dining, Starbucks, major highways, Orlando International Airport, and just minutes from Lake Nona. A great opportunity to own a move-in ready home in a convenient Central Florida location!

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

Listing Agent: Antonio Fuentes, Jr (407-288-5182)

Remarks: Welcome to this stylishly decorated home located at 2358 Salty Winds Way in the sought-after Solara Resort community of Kissimmee. This spacious residence offers six bedrooms and four and a half bathrooms, thoughtfully designed with both comfort and entertainment in mind. The open layout features a modern kitchen with granite countertops, stainless steel appliances, and a pantry, flowing seamlessly into the gathering room and breakfast nook. The first-floor owner’s suite provides a private retreat with a double vanity and large walk-in closet. Upstairs, a versatile loft, a private cinema, and a game room create additional space for fun and relaxation. The home also showcases beautifully themed childrens bedroom with Disney-inspired décor, alongside elegant and stylish design throughout. Outdoors, a covered lanai and private pool offer the perfect setting for entertaining or unwinding. Located in the gated Solara Resort, residents and guests enjoy access to resort-style amenities including a clubhouse, fitness center, and recreational facilities, all just minutes from Disney and Orlando’s top attractions.

Listing is courtesy of: PRISTINE INTERNATIONAL REALTY LLC (407-286-3846)

Listing Agent: Juliana Garcia Moraes (407-721-2442)

Remarks: Turnkey Disney-Area Pool Home with Solar Savings perfect for a primary residence or investment property! Ideally positioned in the heart of Kissimmee, this beautifully maintained 3-bedroom, 2-bathroom pool residence offers a premier investment opportunity just minutes from Central Florida’s major attractions. Currently operating as a highly successful vacation rental, the property boasts immediate income potential. Guests can relax in the private, screened-in pool enclosure, while owners benefit from advanced solar technology that significantly lowers operational utility costs. Situated in a desirable community with No CDD fees. The Association of Poinciana includes an expansive resort style pool, fitness center, Ball room spaces, Dog park, Youth and community programming, memberships are optional for available social activities throughout the community.

Listing is courtesy of: FLORIDA HOMES REALTY & MORTGAGE (904-996-9144)

Listing Agent: Rose Mandes (813-334-4710)

Remarks: You know that feeling of finally exhaling after a long day? That’s exactly what this home feels like the moment you walk through the door. While most Florida backyards look directly into a neighbor’s window, yours looks out over a glassy pond and lush conservation. This is a rare find in a newer community, giving you a quiet sanctuary to watch the sunset while the rest of the world stays on the other side of the fence. Built in 2023, this 4-bedroom, 2.5-bathroom home feels brand new but comes with the upgrades you usually have to wait months for. The first thing you’ll notice is the luxury vinyl plank LVP flooring—it’s stylish, incredibly durable, and covers the main living areas, making cleanup a breeze. The open-concept floor plan is perfect for entertaining guests or enjoying a quiet movie night in. But the real "hidden" feature? A fully paid-off solar system. In Florida, that means you can blast the A/C all summer long while your neighbors worry about their power bills. You’ll enjoy immediate energy savings from day one. Forget looking into someone else’s kitchen. This fully fenced yard opens directly to a peaceful pond and conservation view. It’s the perfect spot for pets to run or for you to unwind while watching the sunset. The standout feature of this backyard is the extended paver patio. Unlike a standard small concrete slab, this professionally laid space acts as a true extension of your home. It’s the perfect spot for a full dining set, grilling, or fire pit area. Imagine hosting Saturday BBQs or enjoying a quiet glass of wine in total privacy. Plus, pavers stay significantly cooler in the Florida sun, making it much friendlier for bare feet and pets. Living in Kindred means you’re part of a community designed for connection. You’re just a half-mile from the brand-new K-8 school—no more long car lines! Perfectly positioned between two amenity centers, whether you want to hit the fitness center, splash in one of the resort-style pools, take a stroll on one of the walking paths, everything is just a short walk or bike ride away. Additional amenities include: soccer field, recreation fields, outdoor exercise stations, pet park, beach volleyball, tennis courts, and pickleball courts. Commuting is a breeze with quick access to the Turnpike and Hwy 192. You’re minutes from the growth of Lake Nona, the Orlando International Airport (MCO), and all the shopping and dining Kissimmee provides. Skip the construction dust and move into a home that’s already been perfected! Schedule your private tour today and see why everyone is falling in love with Kindred!

Listing is courtesy of: RE/MAX TITANIUM GROUP (352-241-6363)

Listing Agent: Lauren Deem (352-275-7155)

Remarks: Location, location! The seller is motivated to assist with some closing costs, which can be used to lower the interest rate or pay for closing expenses. Don't miss this opportunity to live in Tapestry community First time buyers ,investors Spectacular 4/3 with a beautiful landscaping exclusively designed for the property, it is located in one of the best areas of Kissimmee, with good access to I4, Osceola pkwy, 417, 528 and turnpike, access to everything you need for your daily living. It is a 24 hour guarded gate community with excellent amenities In addition, the house has a covered and completely fenced patio to generate privacy in your patio and your parties. Don't miss out on this opportunity.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Juan Oberto (407-810-3694)

Remarks: Welcome to 9039 Pelican Cove Trace — a fully furnished, turnkey 7-bedroom, 6.5-bathroom luxury vacation home located in the coveted gated community of Solara Resort, just minutes from Walt Disney World. This spacious 3,533 sq ft property is designed for optimal short-term rental performance and guest satisfaction, offering themed bedrooms, a private screened pool and spa, and full access to resort-style amenities. The home features an open-concept main level with a gourmet kitchen, oversized island with seating for 8, dining area, cozy sitting space, and a bright living room anchored by a wall-mounted TV and built-in electric fireplace. Sliding glass doors lead directly to your private outdoor oasis — perfect for soaking up the Florida sun or enjoying poolside evenings. Investor highlights include three king suites, two themed rooms (Mickey & Harry Potter), multiple entertainment zones, and no required updates. Solara Resort’s clubhouse includes a surf simulator, water slides, zero-entry pool, splash pad, restaurant/bar, fitness center, sports courts, and more — all included with HOA access. Whether you're building your portfolio or entering the short-term rental market, this income-producing, guest-ready property delivers exceptional return potential, resort-level amenities, and the ultimate Florida experience.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Danilo Aquino (689-243-6300)

Remarks: Under contract-accepting backup offers. Move-in ready home ideally located near shopping and dining. This well-maintained property features an open-concept split floor plan with 3 bedrooms, 2 bathrooms, and a 3-car garage, designed for both privacy and entertaining. Recently painted on the interior, the home offers a spacious kitchen with granite countertops, birch wood cabinets with crown molding, a large island, tile backsplash, pantry, and exterior venting for the microwave. All appliances are included. The primary suite provides ample space and includes an owner’s retreat measuring approximately 11 x 9.8, ideal for a sitting area, office, or flex space. Additional features include a Ring security system and alarm system, as well as 9 exterior security cameras surrounding the property. Enjoy outdoor living with a fully covered and screened lanai, paved driveway, and a spacious backyard with water views and no rear neighbors. The yard is partially fenced with a combination of metal fencing to preserve the lake view and vinyl fencing for added privacy. Turnkey and ready for its next owner.

Listing is courtesy of: INNOVATION GROUP REALTY LLC (407-272-9999)

Listing Agent: Madeline Rivera (407-757-8544)

Remarks: Under contract-accepting backup offers. Welcome to a GREAT OPPORTUNITY! Either to own a FULLY FURNISHED ready-to-go vacation home or a place to call your very own AND WITH A NEW ROOF BY CLOSING. The highly sought-after resort community of TERRA VERDE is perfect for either. A 24 hour guard gated community with resort amenities, Terra Verde is the ideal destination for vacationers as it is only minutes to Disney and easy access to anywhere in Central Florida! A spacious 4 bedroom 3 bathroom split plan layout with 2 BEDS and BATHS EN SUITE. Large, single floor square footage well utilized with two living areas. Relax in the beautiful screened pool and spa or just lounge and enjoy the privacy from NO REAR NEIGHBORS. Add this one to your showing list today! You'll be glad you did!

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

Listing Agent: Mark Colvin (407-637-7301)

Remarks: One or more photo(s) has been virtually staged. Beautiful single-story (ground floor) home located in a quiet, well-located, and peaceful community in Kissimmee, where short-term rentals are allowed — making it an excellent opportunity for a primary residence, vacation home, or short-term rental investment. This property features a 2-car garage, a spacious corner lot, and a screened private pool with solar heating, perfect for enjoying the Florida lifestyle year-round. The main living area (great room) opens directly to the pool through large glass sliding doors, creating a seamless indoor–outdoor flow ideal for entertaining and relaxing. The home includes a roof replacement completed in 2018, and bedrooms feature new vinyl flooring, offering added peace of mind. The backyard provides walkable access to a nearby lake, perfect for scenic walks and enjoying nature. Conveniently located near shopping, dining, major highways, and Central Florida attractions, while still maintaining a calm and residential atmosphere.

Listing is courtesy of: GARCIA REALTY GROUP (407-920-3616)

Listing Agent: Jessica Sato (407-914-3157)

Remarks: This 3 bedroom, 2 bath ranch style home offers 1,493 sq ft of living space, built in 2012 with durable block construction and tile flooring throughout. This property backs to a permanent wooded easement that provides long term privacy and a natural, undevelopable buffer. The interior is freshly painted and features a functional split bedroom layout, spacious living areas, and an air conditioning system replaced within the last 5 years for improved efficiency and comfort. The single story design offers easy accessibility and low maintenance living. This home combines privacy, solid construction, and a rare backyard oasis. An excellent opportunity for buyers with long term appeal.

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

Listing Agent: Monica Dalton (407-207-2220)

Remarks: WOW! BEST DEAL on the Market!! Own a Meticulously Maintained, move-in ready 4 BED + 2 BATH + 2-Car-Garage + Fully-Fenced Backyard Home in a Beautiful Neighborhood at the INCREDIBLE price of $300K!!! Exciting updates that bring peace of mind (& discounted homeowner's insurance rates) are: NEW ROOF (2023), NEW HVAC (2025) AND a New Water Heater (2025)! NO Flood Zone (Flood Zone X), Brand New Interior Paint throughout (2026), an Entire Home Water Filtration System, All Kitchen Appliances, and Washer/Dryer are INCLUDED!!! Enjoy a smart and welcoming floorplan where 3 bedrooms and a separate indoor laundry room greet you at the front of the home, while the entryway opens effortlessly into a spacious living room, dining room, and kitchen complete with a large island that’s perfect for gathering, entertaining, or extra seating. Tucked away in the back of the home for added privacy, the primary suite feels like your own retreat with a large walk-in closet, relaxing soaking garden tub, and a separate oversized standing shower. The charming backyard is made for anyone who appreciates privacy and low-maintenance living — fully fenced and filled with mature landscaping and beautiful fruit-producing trees — creating the perfect spot to unwind with a glass of wine and enjoy your own peaceful Florida oasis at the end of the day. Located in Kissimmee’s Hammock Trails neighborhood where you can truly live where the magic happens! Just minutes from Walt Disney World, Disney Springs, Celebration and Historic Downtown Kissimmee. Enjoy a community pool, soccer field, and playground with an easy commute to local schools, shopping, and everything Central Florida has to offer!

Listing is courtesy of: CENTURY 21 MCBRIDE REALTY GROUP (386-866-1007)

Listing Agent: Janissa Soto (386-882-1430)

Remarks: BIG PRICED REDUCTION!! CHECK OUT THE VIRTUAL TOUR!!! The buyer will need to assume the Solar Loan at approximately $86K. Easily Assumable. Come see this Amazing Fully Furnished single family POOL home in the gated Windsor Palms resort community with 24 hour security. Windsor Palms is just minutes from Walt Disney World, Sea World, Universal and provides an amazing Vacation for both you and your guests. This home has a New Roof and Solar Panels installed. The Buyer to assume the Solar Loan, and still take advantage of the great electrical rates!! Carpet has been replaced with beautiful Laminate thru all the bedrooms. Centrally located close to area attractions, dining and shopping. The community facilities include on-site convenience store, large community pool with tiki bar, whirlpool spa, clubhouse with fitness room, game room, tennis, movie theater, basketball and volleyball courts and playground.

Listing is courtesy of: EPIC FLORIDA REALTY LLC (407-553-3313)

Listing Agent: Harold Olson (407-738-6600)

Remarks: Just Listed in Solivita! Rare opportunity to own one of the few 3-bedroom, 2-bath homes available in this sought-after 55+ community. This beautifully fully renovated home is currently one of the lowest-priced remodeled 3-bedroom properties on the market. Every detail has been thoughtfully updated with high-end finishes and modern design throughout. Features include luxury waterproof white oak LVP flooring, a stunning chef’s kitchen with white cabinetry, gold hardware, Calacatta Storm Gold quartz countertops, and brand-new stainless steel appliances. The spa-inspired bathrooms showcase elegant white and gold finishes, frameless glass showers, and premium rain shower fixtures. Fresh interior paint and exceptional craftsmanship make this home truly move-in ready. Enjoy relaxing water views from the screened Florida room — perfect for entertaining or outdoor dining. Homes like this rarely become available and won’t last long! Solivita is a vibrant 55+ resort-style community featuring exceptional amenities, including fitness centers, heated pools, tennis and pickleball courts, golf courses, on-site dining, and a full calendar of activities and events. The community also features two championship 18-hole golf courses. Conveniently located near shopping, hospitals, and medical offices, it offers the perfect blend of active living and everyday convenience.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Roberta Soares Reis (407-985-6957)

Remarks: Under contract-accepting backup offers. Rare Find in Adriane Park! Located in highly sought-after community of only 55 homes, known for its peaceful setting, spacious lots, and convenient location. This beautifully maintained 4-bedroom, 3 full bathroom home offers 2,444 heated square feet with a functional 3-way split floor plan. As you enter, you are welcomed by a spacious living and dining room featuring crown molding, chair rail accents, custom drapes, soaring 10-foot ceilings, and an abundance of natural light from four skylights throughout the home. The dining room connects conveniently to the kitchen through a charming swinging door. The spacious kitchen features granite countertops, a breakfast bar, dinette area, skylight, and plenty of storage space. Matching GE Stainless appliances. The kitchen opens to the inviting family room with a cozy wood-burning fireplace and French doors leading to the oversized screened lanai. Privately situated off the family room, the primary suite offers French door access, a walk-in closet, and an ensuite bathroom complete with a jacuzzi tub, separate shower stall, and private water closet. Bedrooms two and three are located on the opposite side of the home and share a spacious hall bath with dual sinks and a tub/shower combination with direct access to the lanai — already perfectly set up for adding a future pool. The 4th bedroom is conveniently located near the kitchen and offers ensuite access to the 3rd full bathroom, making it an ideal setup for guests, extended family, or a private home office. Step outside and enjoy the impressive 10x40 screened lanai overlooking the spacious backyard and peaceful pond view. Part of the lanai is covered, creating the perfect relaxing space, while the screened area offers an ideal setup for grilling and enjoying beautiful evening sunsets. Additional updates and features include: • Replumbed in 2023 • New toilets in 2023 • Interior painted with Sherwin-Williams Super Paint • Roof replaced in 2015 • Water heater replaced in 2017 • Sprinkler system • Intercom system • 1-year home buyer’s warranty included for added peace of mind. Corrugated metal storm panels included with the home. Equip with flood lights on all 4 corners. Low HOA fees of only $220 semiannually and NO CDD. Conveniently located near Osceola Hospital, Downtown Kissimmee, and the Florida's Turnpike. Ready to call this your new home? Call today to schedule your private showing!

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

Listing Agent: Janet Mcquagge (407-927-7399)

Remarks: Welcome home to this beautifully renovated 3 bedroom, 2 bath Savoy model in the highly sought after GATED and GUARDED Solivita community. Designed with a desirable split floor plan, this home showcases thoughtful upgrades and modern finishes throughout. Step inside to find luxury vinyl flooring flowing seamlessly through the main living areas, complemented by stylish tile in the kitchen and bathrooms. Fresh paint and trendy light fixtures add a bright, contemporary feel, while a BRAND NEW 2024 ROOF offers peace of mind. The stunning kitchen is truly the heart of the home, featuring all NEW stainless steel appliances, sleek QUARTZ countertops, and an ample amount of NEW cabinetry. A spacious breakfast bar opens to the living area, creating the perfect setting for entertaining family and friends. The primary suite includes a private adjoining sitting room for an added touch of luxury. Beyond the home, Solivita offers an unmatched lifestyle in a vibrant 55+ active adult community. Residents enjoy access to over 40 exceptional amenities, including 14 heated pools, multiple spas and hot tubs, pickleball and tennis courts, two golf courses with a driving range, an indoor walking trail with air conditioning, on site dining, a spa, dog parks, and even a farmers market, just to name a few. Experience resort tyle living every day in this move in ready gem.

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

Listing Agent: Natalie Feldman (407-574-1915)

Remarks: Short Sale. AMAZING COTTAGE FOR SALE AT MARGARITAVILLE RESORT ORLANDO. This Cottage has 3 Bedrooms, 3 Baths, High-End Quartz Countertops, Upgraded "Wood" Tile Flooring and Appliances, High Capacity Washer and Dryer. Kitchen has Large Counter Space and Windows with Lots of Natural Light. The Door from the Kitchen Leads you to a Beautiful Patio with Lounge Chairs and Tropical Landscaping with Shell Pathways, Palm Trees and Tropical Foliage. Primary Bedroom Located Upstairs has En Suite Bathroom. One Bathroom has a Shower/Tub Combo. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES ALL Furniture and Housewares, Also Includes Blinds, Drapes, TVs, Artwork, Linens, and So MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice for Living or a Great Investment Property For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

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

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

Remarks: 3-bedroom, 2-bath home with a screened-in pool and pond view. No HOA. Conveniently located near shopping, Florida’s Turnpike, theme parks, and about 30 minutes to downtown Orlando.

Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)

Listing Agent: Troy Funk (941-241-3850)

Remarks: One or more photo(s) has been virtually staged. Discover the perfect blend of modern elegance and convenience in this meticulously updated 5-bedroom, 3.5-bath home nestled in the tranquil Rolling Hills neighborhood. Featuring stunning vaulted ceilings, durable Pergo engineering flooring, and an open-concept living area bathed in natural light. The designer kitchen boasts quartz countertops, a stylish backsplash, and stainless steel appliances. Relax in the refined comfort of remodeled limestone bathrooms. The main floor features a private primary suite, a second bedroom, and a full laundry room. Step outside to your private screened-in oasis—perfect for entertaining. Whether you are looking for a stunning primary residence, a relaxing vacation home, or a high-yield investment, this home offers it all.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Manuel Hernandez Pacheco (407-686-7686)

Remarks: Now Offered at an Improved Price! Welcome to this stunning, newly renovated, TURN-KEY Themed Vacation Home situated within the gated community of Reunion Resort. Over 40K in future bookings already reserved through the end of 2026. This exquisite property boasts a private pool and spa, as well as an array of incredible features and themes that will transport you to a world of adventure and imagination. As you enter the home, you are greeted by an open and bright living room area with a Pirates of the Caribbean theme throughout the first floor. The living room is complete with an HD TV and overlooks the fully equipped kitchen, featuring solid stone countertops and stainless-steel appliances. The dining area with seating for 8 completes the open concept layout. On the main floor, you will also find the large master bedroom with a king-size bed, en-suite bathroom with double sinks, a soaking tub, and a walk-in shower. Prior to making your way up the stairs, there is a fully converted state-of-the-art movie & arcade bonus room. This impressive space includes 8 theater-style chairs, a 120-inch projection TV, 2 Batman driving gaming consoles, a Terminator shooting game, and an Xbox gaming area. Upstairs, you will find the pub loft area, complete with a pool table, an oversized bar area, a large TV with neon lights, and another full-size gaming console for playing Golden Tee Golf and other classic games before hitting the course. The second floor features two professionally themed kid sanctuaries. The first is a Harry Potter World of Wizardry room with two full-sized bunk beds and a hidden slide that leads to the second theme bedroom. The second bedroom is a Star Wars inspired room with amazingly realistic armored transport décor and a bunk bed. Additionally, there are two more king suites, one of which has a walk-out balcony overlooking the stunning views of the golf course. Enjoy the resort lifestyle within the gated community of Reunion Resort, just minutes away from Walt Disney Parks, other major Orlando attractions, and some of the best beaches in the world. The resort itself offers 12 community pools, 3 signature golf courses (Palmer, Watson, Nicklaus), a multimillion dollar water park, several onsite restaurants, 2 golf pro shops, six hydro-grid clay tennis courts, a full-service spa, and a brand new miniature golf course. Financials are available upon request to anyone looking to make this an investment property. There are many options for rental management companies that we can provide more information on.

Listing is courtesy of: XCELLENCE (866-595-6025)

Listing Agent: Dan Dinozzi (203-982-7164)