Kissimmee Single Family Homes For Sale - 1550 homes

Remarks: Experience refined resort-style living in this fully remodeled six-bedroom, four-bath luxury pool home located within the exclusive gated community of Windsor Resort. This exceptional residence features a new roof, modern contemporary design, high-end finishes, spacious open interiors, and brand-new premium appliances throughout. Offered fully furnished, this property provides a true turnkey opportunity. Currently operating as a successful short-term rental across multiple platforms, it offers outstanding income potential with no rental restrictions. Ideally situated just 2.5 miles from Walt Disney World and minutes from world-class dining, shopping, and entertainment. Perfect for use as a primary residence, vacation retreat, or investment property.

Listing is courtesy of: MALIBU BAY REALTY (786-601-7928)

Listing Agent: Lisbey Tamayo Pa (786-514-9356)

Remarks: TRANSFERABLE REUNION MEMBERSHIP AVAILABLE! Make sure to check out the Virtual Tours and 3D Videos Come experience this beautifully updated, fully furnished 4-bedroom home located in the highly desirable Patriots Landing neighborhood of Reunion Resort. Professionally decorated with thoughtful details throughout, this property is turn-key and ready for short-term rental, a private vacation retreat, or full-time living. As you approach the home, you'll immediately notice the spacious corner lot and charming wraparound porch, perfect for enjoying the Florida lifestyle. Inside, the main floor features a large bedroom that can serve as a primary suite, making it ideal for guests or anyone who prefers to avoid stairs. The open-concept kitchen overlooks the expansive living and dining area, creating the perfect space for entertaining. The kitchen has been updated with new appliances and is designed for both style and functionality. Upstairs, you’ll find newly updated flooring throughout the second level, along with two guest bedrooms, including one featuring professionally designed beach-themed bunk beds that guests will love. The spacious primary suite is also located on the second floor and includes a private ensuite bathroom with a relaxing soaking tub and a separate large shower. Step outside through the French doors on the main level to your private pool and spa oasis, the perfect place to relax, entertain, and soak up the Florida sunshine. This home has numerous updates throughout and is a must-see in person. Reunion Resort, a prestigious 2,300-acre luxury community, offers an incredible array of amenities for every lifestyle. Residents and guests enjoy three signature golf courses designed by Arnold Palmer, Tom Watson, and Jack Nicklaus, along with the world headquarters of the Leadbetter Golf Academy, making it a true golfer’s paradise. Located just minutes from Walt Disney World and Orlando’s world-famous attractions, and within easy driving distance of Florida’s beautiful beaches, Reunion offers the perfect blend of luxury, entertainment, and relaxation. The resort also features a water park, 12 community pools, two golf pro shops, hydro-grid clay tennis courts, pickleball courts, and miniature golf. Experience the luxury resort lifestyle you’ve been searching for at this exceptional Reunion property. Schedule your private tour today—this opportunity won’t last long!

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

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

Remarks: Under contract-accepting backup offers. Welcome to this beautiful turn-key 8 bedroom, 6 bathroom home. This home comes fully furnished and qualifies as a SHORT-TERM RENTAL. Inside, the home has been completely remodeled. Each bedroom, the kitchen, family room, and game room are uniquely themed for a fun, immersive experience. The converted garage functions as a custom game room, featuring a full-size commercial air hockey table, slate pool table, foosball, sofa set, toys, TV, and a durable epoxy floor. The updated kitchen features stainless steel appliances, granite countertops, a stylish tile backsplash, and comes fully stocked with dishes, cookware, and small appliances. This incredible home provides equal 4/3, bed/bath accommodations downstairs and upstairs, along with two living areas including a formal front living room and a comfortable family room set towards the rear. The laundry room is equipped with a washer and dryer, plus an additional dryer in the converted garage. Flooring includes travertine downstairs and newly installed vinyl plank upstairs, creating both elegance and durability. The roof was installed in 2017, water heater 2022, pool heater 2021, and pool salt cell 2024. Throughout the home, you'll find WiFi keyless entry, plantation shutters, crown molding, modern lighting, and ceiling fans. Every bedroom is stocked with backup sheets and comforters, and all mattresses and pillows are protected with high-quality covers for added comfort and cleanliness. This exceptional property sits on a spacious .287-acre cul-de-sac lot and is designed for both relaxation and entertainment. The highlight is the massive 20' x 40' screen enclosed private pool paired with an oversized spa. Surrounding the pool, you'll find a generous patio with two dining tables, five lounge chairs for sunbathing, and a covered lanai complete with a TV and refrigerator. The pool has been resurfaced with elegant Pebble Tec finishing, while the patio was recently repainted for a fresh look. Step outside the screen enclosure to enjoy a covered grilling area with picnic table, outdoor ping pong table, cornhole set, and a huge Little Tikes playground all set on low-maintenance artificial turf. The backyard is fully private, enclosed by fencing, hedges, and a rear brick wall, with a charming wrought-iron section offering a picturesque pond and fountain view. Conveniently located in close proximity to I-4 and SR 429, this home is 5-10 minutes from world-class dining, shopping, theme parks, mini golf and Sunset Walk at Margaritaville (bars, shops, movie theater, water park). It is one of the closest communities to Disney. With over $50K in upgrades and an unbeatable location, don't miss this rare opportunity to be the next owner of this immaculate home!

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Nicholas Giovanetti (321-239-7622)

Remarks: Luxury pool home less than 10 miles from Walt Disney World. Make this your new fulltime residence, or earn money on short-term vacation rentals. Top features include a heated pool and spa for year-round enjoyment, private water and conservation view from the pool deck/lanai, 4 full bathrooms with convenient bathroom access from the pool deck, single-story construction, all tile floors, modern open floor plan and split bedroom plan, and low HOA fee. Located within the high-demand Disney "Golden Triangle" resort area, this home is less than 15 minutes door-to-door to the Magic Kingdom and convenient to the extensive amenities right outside the Disney resort without the high resort fees at other properties. Five bedrooms and four bathrooms easily accommodate 10 people. The home works as a vacation rental or as a fulltime residence within easy reach of tens of thousands of Disney and tourism jobs.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Barbara Liston (407-739-7182)

Remarks: Do not waste time to see this 3 bedroom 2 bath home, located in the lovely neighborhood of Renee Terrace. It is Close to the Loop shopping center, Turnpike, about 20 minutes to Orlando International Airport. Advent Health Hospital and ORMC are very close. It is located about 25 minutes to Walt Disney World and 30 minutes to Universal Studio and SeaWorld. The Roof is just 3 year old. It has new kitchen, ceiling fan, and the property is fully fenced. It has a huge back yard available for your needs. This home is ready for you to move in. Don't miss this opportunity.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Frisnel Senevil (407-272-3174)

Remarks: One or more photo(s) has been virtually staged. Beautifully maintained 4-bedroom home in desirable Heron’s Landing, ideally located near Loop West in the City of Kissimmee, on the border of Osceola and Orange County. This spacious single-story residence offers 2,059 square feet with a popular split floor plan and open, airy layout. Recent upgrades include fresh interior and exterior paint (2026) and new vinyl flooring (2025), newer roof (2018) and newer HVAC (2017). A formal living and dining area welcomes you at the foyer. The updated kitchen is ideal for cooking and entertaining, featuring ample counter space and newer appliances. The kitchen and breakfast nook open to a spacious family room with high ceilings, creating an inviting setting for gatherings. Both the sliding glass doors and breakfast nook french doors extend your living space to a gorgeous screened-in lanai, perfect for relaxing or entertaining. The primary suite overlooks a large backyard with lush fruit trees and features private lanai access. The en-suite bathroom offers a garden tub, separate shower, dual-sink vanity, and an oversized walk-in closet. Three additional bedrooms provide generous closet space, excellent natural light, and share a full bathroom. Additional highlights include newer laminate flooring in main living areas (no carpet at all), an indoor laundry room with extra storage, a 2-car garage with attic access, professionally cleaned HVAC system and whole-house ducts (2025), home security system, and irrigation system. Heron’s Landing is part of a well-maintained Eagles Reserve community, offering low HOA fees and amenities such as a community pool, playground, park areas, and fitness trails. Enjoy the convenience of being very close to The Loop, a sprawling outdoor mall with department stores, specialty shops, and casual dining. Close to Disney attractions, hospitals, Florida Turnpike, and SR-417. Move-in ready with major updates (see attached lists) —don’t miss this exceptional opportunity!

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Sherry Wang (484-744-4586)

Remarks: Seller is motivated and willing to provide a credit toward a new roof, offering a valuable opportunity for the buyer to complete improvements while securing ownership as we approach the busy spring market. Located within the gated community of Cumbrian Lakes, this fully furnished home offers flexibility for use as a primary residence, second home, or short-term rental (buyer to verify all rental restrictions, licensing, and HOA requirements). The community is known for its well-maintained streets, mature landscaping, tranquil ponds, and gated access. Upon arrival, the home welcomes you with attractive curb appeal, mature trees, and a private driveway setting. Inside, a bright foyer opens to an expansive great room filled with natural light from large windows and sliding glass doors. Tile and laminate flooring extend throughout the main living areas, providing durability and easy maintenance suited for Florida living and rental use. The open floor plan connects the great room, dining area, and kitchen—ideal for entertaining or accommodating guests. The centrally located kitchen features ample cabinetry, modern appliances, and a breakfast bar overlooking the living space. The adjacent dining area flows seamlessly to the lanai and pool area, offering private conservation views that enhance everyday living and guest appeal. Sliding glass doors lead to a screened lanai and private pool within a fully fenced backyard. Beyond the fence, a lush conservation buffer provides added privacy and a peaceful backdrop—perfect for outdoor relaxation. The primary suite offers a quiet retreat with a large walk-in closet and an en-suite bath featuring dual sinks, a soaking tub, and a separate shower. Three additional bedrooms are generously sized and adaptable for guest accommodations, home office space, or flexible living arrangements. Indoor laundry and ample storage contribute to the home’s functional layout. Recent improvements include a new air condenser (approximately 2 years old), hot water heater (approximately 1 month old), and pool pump (approximately 2 months old), reflecting ongoing maintenance and reduced near-term capital needs. Community amenities include walking paths, lakes, playground areas, and the added security of gated entry. Conveniently located near major highways, shopping, dining, golf courses, and world-famous Central Florida attractions—including Walt Disney World—this property presents a strong opportunity for homeowners and investors alike.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Simi Lakhani (407-408-7393)

Remarks: LOCATION! LOCATION! Turnkey 4-Bed, 4-Bath Home in Windsor Hills Resort – Minutes from Disney! Step into this fully furnished, move-in ready home featuring 1,878 sq ft of open-concept living space. The spacious layout flows seamlessly from the bright living areas to a private screened-in pool and spa—perfect for relaxing or entertaining. The chef’s kitchen, plush bedrooms, and tile flooring throughout common areas provide both comfort and style. Recent upgrade includes new water heater (2025), and the roof will be replaced with an accepted offer, giving you peace of mind for years to come. Enjoy resort-style amenities just steps from your door: a clubhouse with movie theater, fitness center, sundry shop, and arcade game room; a water park with zero-entry pool, slides, and hot tub; plus, tennis, basketball, volleyball courts, putting green, and a playground. Whether you’re looking for a vacation home, short-term rental, or full-time residence, this property combines luxury, convenience, and value in one of Kissimmee’s most desirable communities. Schedule your private tour today!

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Valeria De Alvarenga Godofredo (689-276-3391)

Remarks: A phenomenal vacation rental investment opportunity with great income potential! Discover this prime lot in the vibrant Windsor at Westside, perfectly nestled across from the clubhouse with stunning lake view. This impeccably maintained vacation home is fully furnished with upgraded furniture, including three lavish primary suites and fun themed bedrooms, perfect for large vacation groups. The home boasts newly upgraded luxury vinyl flooring in all bedrooms (NO carpet), sleek granite counter tops in the kitchen and bathrooms, premium stainless steel appliances, and stylish tiles. Dive into relaxation with a private screened pool, paver deck, and covered lanai, backing to a natural pond and conservation area. Energy-smart features like two high-efficiency AC units, LOW-E dual-pane windows, and modern appliances keep it eco-friendly and cost-effective. This guard-gated community dazzles with a 10,000-square-foot resort-style clubhouse with arcade game room, a sparkling heated pool and spa, a meandering lazy river, a thrilling mini water park, a cutting-edge fitness center, a lively tiki bar, and all sorts of sports fields. Landscaping, internet, cable, and daily valet garbage collection are included in the HOA fee. Just minutes from Walt Disney World, premier golf courses, vibrant shopping, the airport, and major attractions, this is your chance to own a slice of paradise for investment or 2nd home! Schedule your exclusive private tour today!

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Sherry Wang (484-744-4586)

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: Under contract-accepting backup offers. Welcome to 2331 W Oak St in the heart of Kissimmee! This charming 3-bedroom, 1-bath home plus a separate 1/1 unit offers fantastic flexibility—perfect for extended family, guests, or potential rental income. Enjoy peace of mind with impact windows, a 2020 roof, and a whole-home water softener. The updated kitchen features modern finishes and a bright, functional layout. Outside, the property boasts a spacious backyard and covered areas ideal for gatherings, cookouts, and outdoor entertainment. Located just minutes from world-famous Disney parks, major roads, shopping, dining, and all that Central Florida has. Don’t miss this versatile and move-in ready opportunity!

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

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

Remarks: Beautifully furnished home is located on a Coner lot & conservation area in Storey Lake resort. Community offers amenities include Tiki Bar/Grille, Canoe/Kayak Rental, Lazy River, Fitness Center, Miniature Golf, Quiet Pool, Splash Pad, Double Slide, Volleyball Court & Sports Court. Short/term rental

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

Listing Agent: Aria Pedroso (321-284-9197)

Remarks: Charming Investment Opportunity – Cash Only – Over 2 Acres with Endless Potential Unlock the possibilities with this charming investment property situated on over 2 acres of land, offering incredible potential for the right buyer. This cash-only opportunity is perfect for investors, builders, or anyone looking to create their vision from the ground up. Nestled in a convenient location close to schools, grocery stores, and a variety of everyday amenities, this property combines space, location, and opportunity. Whether you're considering renovation, expansion, or redevelopment, the generous lot size provides plenty of room to bring your ideas to life. With its desirable setting and strong upside potential, this property is a rare find for those seeking value and long-term growth. Don’t miss your chance to transform this hidden gem into something truly special!

Listing is courtesy of: HOMETRUST REALTY GROUP (813-444-5777)

Listing Agent: Diana Quintana (706-461-2854)

Remarks: "LAZY PARROT" is a Charming Cottage at Margaritaville Resort Orlando. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Located in PREMIUM RESORT LOCATION Just a Short Walk to All the Amenities! MRO Approved City Furniture "SAIL AWAY" Furniture/Housewares Package Included in List Price. Beautiful 1539-C Model, 3 Bedrooms, 3 Bathrooms with BONUSROOM and CUSTOM PARROT DESIGN SHUTTERS. Master Suites on BOTH First and Second Floors. Downstairs Suite has French Doors Leading to Tranquil Backyard with Paved Patio, Beautiful Tropical Foliage and Shell Pathways. All Three Bedrooms have KING BEDS! The Furniture is the Original City Furniture MRO Approved Package and Some Items are No Longer Available to Purchase. Home Features High Capacity Washer and Dryer, "SON OF A SAILOR" Interior Upgrade Package with "WOOD" Tile Flooring, Upgraded Appliances, QUARTZ Countertops, Ceiling Fans and TANKLESS WATER HEATER. There is an Additional Bonus Room Upstairs with a BUILT IN TWIN BED and TV. Furniture/Housewares Package Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishwasher, Linens, and so MUCH MORE! This Unique First of its Kind Resort has Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! LOCATED MINUTES FROM DISNEY PARKS!, All While Being Conveniently Close To The Best Shopping, Dining, and Entertainment Options In Florida. This Home Is Not Just A Residence; It's A Lifestyle Choice 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: Great 4 bedroom 3 bath home in a gated community. lose to the schools. Split floorplan, built-in entertainment center.

Listing is courtesy of: MBT HOMES (407-569-5884)

Listing Agent: Pascale Trosch (407-791-6319)

Remarks: Completely renovated and move-in ready! This home showcases stunning polished porcelain ceramic floors 24' x 48' throughout, an open floor plan with a fully remodeled kitchen equipped with all-new stainless steel appliances, modern cabinetry, and countertops. Bright, bright floorplan and contemporary finishes for effortless, low-maintenance living. Upgraded fixtures and thoughtful design deliver modern comfort and style. Home features an above-ground pool with a deck, ideal for outdoor entertaining and relaxation. Great potential for gatherings and enjoying the Florida lifestyle, and easy to maintain. Ideal for buyers seeking a turnkey condition in a convenient neighborhood.

Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)

Listing Agent: Miguel Osorio (321-240-5554)

Remarks: Welcome to 1673 Barberry Lane, a beautifully upgraded Cali model located in the heart of Kissimmee, FL, offering over $80,000 in thoughtful upgrades and designed for both comfortable living and income-producing potential. This home stands out from the moment you arrive, combining modern enhancements, functional design, and premium features throughout. Whether you’re looking for a primary residence, second home, or Airbnb opportunity, this property checks all the boxes. Step inside to a well-maintained and inviting interior featuring ceiling fans in every room with independent controls, upgraded chandelier lighting in the kitchen and dining areas, and an expanded pantry with added shelving for extra storage and convenience. The kitchen is equipped with a newer dishwasher that includes a transferable warranty, adding peace of mind for the next owner. One of the most unique features of this home is the upgraded garage space, which has been transformed into a versatile and functional area. It includes its own independently controlled HVAC system (2024), epoxy-coated flooring, added storage shelving, and a custom sliding privacy screen—perfect for a home gym, workspace, or additional flex space. The home’s HVAC system has been recently serviced (March 2026) and includes an extended transferable warranty with approximately 7 years remaining, along with a built-in UV air purification system designed to help reduce bacteria, mold, and airborne contaminants—an incredible value and added comfort feature. Step outside to your private outdoor retreat, where attention to detail continues. The property features a fully fenced yard, a complete gutter system, and a full concrete walkway surrounding the home. The highlight is the extended screened-in lanai with pavers (16’ x 20’), completed in 2024, featuring an insulated covered roof, ceiling fans, motion-detection lighting, and a dedicated outlet for outdoor cooking or entertaining. A translucent Florida glass enclosure adds additional weather protection while still allowing natural light to flow through. Located in a growing area of Kissimmee with convenient access to shopping, dining, schools, and major roadways, this home offers both lifestyle and long-term value. If you’re looking for a move-in-ready property with extensive upgrades, flexible living space, and strong potential, 1673 Barberry Lane is a must-see. Schedule your private showing today and experience the difference for yourself.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Rafael Ortiz Pena (407-371-8773)

Remarks: A rare opportunity to own a fully furnished turnkey pool home in one of Orlando’s most desirable resort communities, perfectly positioned for personal use, vacation living, or exceptional short-term rental income. This beautifully appointed 5-bedroom, 5-bathroom home offers the ideal blend of comfort, style, and versatility. The spacious open-concept layout features a modern kitchen, elegant finishes, and inviting living and dining areas designed for both entertaining and everyday enjoyment. Each bedroom is tastefully furnished to provide a comfortable and relaxing retreat for owners and guests alike. Step outside to your own private screened-in pool, perfect for enjoying the Florida sunshine after a day at the parks or hosting family and friends. Located in a short-term rental approved resort-style community, residents and guests enjoy access to outstanding amenities and a prime Central Florida location just 21 minutes from Walt Disney World and only 30 minutes from Universal Studios. Whether you are seeking a primary residence, vacation getaway, or turnkey income-producing investment, this property is ready to impress. Offered fully furnished and move-in/rent-ready, it presents an exceptional opportunity in one of Orlando’s strongest and most sought-after vacation rental markets.

Listing is courtesy of: ALVES AND HOWELL REALTY (407-750-2171)

Listing Agent: Laercio Xavier (321-353-4477)

Remarks: Welcome to this massive two-story pool home situated on a premium corner lot of over a quarter acre in Kissimmee! Boasting over 3,500 square feet of living space, this home offers the perfect blend of comfort, functionality, and entertainment. As you step inside, you're greeted by soaring high ceilings and an open layout, complemented by brand new interior paint (upstairs) and newer flooring throughout the main level. The spacious first-floor primary suite provides convenience and privacy, while the upstairs features an extra-large bonus room and a dedicated theater room, ideal for movie nights, a game room, or additional living space. The heart of the home flows seamlessly into the outdoor oasis, where you'll find a private pool with newly added pavers and an in-ground hot tub, perfect for relaxing or entertaining guests year-round. Additional upgrades include a brand new washer, dryer, and refrigerator, making this home truly move-in ready. The oversized lot offers plenty of outdoor space, while the corner positioning adds both privacy and curb appeal. Conveniently located near shopping, dining, and major roadways, this home checks all the boxes for space, upgrades, and lifestyle.

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Naf Zaman (407-580-5483)

Remarks: 5 Bedroom 4 Bath Vacation Dream home in Indian Creek. A MUST SEE!! Close to the parks and shopping. Can be used for your vacations and also be rented out Short Term. Fully equipped for your Vacation Rentals Home some recent updates Exterior Paint 11/2025, New pool Heater 2/2024, Dishwasher & pool Pump 10/2023, Garbage disposal 7/2022, new roof 1/2022, New AC 11/2019 All furnishings included, Flat screened TV's Stove, Refrigerator, Washer & Dryer and Landscaping. any bookings available will convey!! Be sure to put this on your list to view!

Listing is courtesy of: ROYAL REALTY PROPERTIES (407-595-7306)

Listing Agent: Steve Farah (407-595-7306)