Location: Kissimmee , 34744
Do Not Show Listings
1135 CHEROKEE DR, KISSIMMEE, FL 34744
$368,90052 Days on yellowkey MLS ID: S5144943
REDUCED by $7,090 (1.9%) on 04/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1358 Built: 1964 Tax: $1,014 (2025)Community: Osceola AcresSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,014
Elementary School: Mill Creek Elem (K 5)
High School: Osceola High School
Tax Year: 2025
Middle School: Denn John Middle
Remarks: FULLY RENOVATED HOME on an oversized 0.40-acre corner lot in Kissimmee with NO HOA! Major 2025 upgrades include a new roof, new A/C, all new windows, updated electrical and plumbing systems — offering true peace of mind. Features include an open-concept layout, luxury vinyl flooring, fully remodeled bathrooms, blinds, and a modern kitchen with quartz countertops and a large island. The fully fenced yard provides incredible space to build a pool, expand, or park your RV and boat with no restrictions. Prime central location near major highways, shopping, dining, and schools. Move-in ready with space, upgrades, and freedom — a rare find.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Arlenys Oviedo (786-803-4342)
14 GLENDALE DR, KISSIMMEE, FL 34744
$528,90041 Days on yellowkey MLS ID: S5145799
REDUCED by $6,000 (1.1%) on 04/23/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2510 Built: 1970 Tax: $5,664 (2025)Community: Fairlawn ManorSingle Family
Taxes:$5,664
Elementary School: None
High School: None
Middle School: None
Remarks: Stunning fully remodeled home located in a premium Kissimmee location near Downtown Kissimmee, just minutes from the beautiful Kissimmee Lakefront Park, restaurants, shops, and local attractions. This move-in ready property features a modern contemporary design with luxury finishes throughout. Enjoy a bright open layout, spacious living areas, and a kitchen with quartz countertops and stainless steel appliances. The home offers waterproof vinyl flooring, and a private balcony off the primary bedroom. Conveniently located near major highways, Orlando International Airport, theme parks, shopping, dining, and schools, this home offers the perfect combination of style, space, and location.
2220 EMPEROR DR, KISSIMMEE, FL 34744
$624,9002 Days on yellowkey MLS ID: S5148275
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2502 Built: 1991 Tax: $3,970 (2025)Community: Cane Brake Ph 2Spa: NoSingle Family
Taxes:$3,970
Remarks: Welcome to Paradise! This beautifully upgraded solid brick residence offers over $100,000 in premium improvements and the rare luxury of NO HOA, complete with conservation area privacy and no rear neighbors. Featuring an elegant open floor plan with a marble foyer, new windows and doors, a 2022 roof, and 2017 A/C, serviced yearly, this home blends timeless quality with modern comfort. French doors open to a newly finished 24’ x 13’ climate-controlled addition, while the expansive primary suite includes a dedicated office area ideal for remote work. All three bedrooms are a great size, and each one has a king bed. Huge 26 ' x 16' Living room/great room is large enough to hold a large bar and full sized pool table. Enjoy resort-style outdoor living with a sparkling 15' x 30' private pool, newly rescreened enclosure with privacy 36" kick plates, new outdoor lighting, low-maintenance stone landscaping, and a new 25' x 30' concrete pad with a 10' x 20' custom shed. Additional upgrades include new carpeting, Levolor blinds, custom color seamless gutters, underground drainage, tinted windows, hurricane shutters, and a hurricane-rated garage door. The large backyard is perfect for family gatherings, with plenty of room for pets to run. Enjoy peaceful privacy with woods behind you, beautiful sunsets, and ample space for a gazebo or tent. There’s even room to play volleyball, baseball, wiffle ball, run the bases, throw a football, work on your tan, and host a barbecue or pool party. In the peaceful Cane Brake community—known for its quiet, one-entrance design and long-term residents—this home offers exceptional comfort, privacy, and a serene atmosphere that feels like a private retreat. Schedule your showing today.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Todd Krentzel (407-279-9899)
1709 MICHIGAN AVE #C, KISSIMMEE, FL 34744
$134,9003 Days on yellowkey MLS ID: S5148282
REDUCED by $10,100 (7.0%) on 04/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1118 Built: 1973Monthly Fee: $298 Tax: $2,400 (2025)Community: Essex Park VillasCondo
Taxes:$2,400
Elementary School: Deerwood Elem (Osceola Cty)
High School: Gateway High School (9 12)
Remarks: Excellent opportunity to own a 2-bedroom, 2-bath condominium in the heart of Kissimmee. This property offers approximately 1,118 square feet of living space with a functional layout that includes a combined living and dining area, kitchen, and well-sized bedrooms with natural light throughout.Located within an established community with convenient access to the Florida Turnpike and major roadways, and just minutes from shopping centers, restaurants, supermarkets, and essential services. Additionally, the property is a short driving distance to Orlando’s major theme parks and the Orlando International Airport, making it an ideal option for both primary residence and investment. Seller is open to considering offers. Don’t miss this opportunity.
Listing is courtesy of: GPS PROPERTY GROUP INC. (407-439-2527)
Listing Agent: Abel Jimenez (407-452-4119)
1489 TWIN VALLEY TER, KISSIMMEE, FL 34744
$549,90029 Days on yellowkey MLS ID: O6390966
REDUCED by $10,100 (1.8%) on 04/18/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2674 Built: 2017Monthly Fee: $11 Tax: $7,067 (2025)Community: Kindred Ph 1A & 1BSpa: NoSingle Family
Taxes:$7,067
Remarks: Step into a home that feels like a fresh start! Located in the highly sought-after Kindred community, this expansive 5-bedroom, 3-bathroom residence offers a versatile flex room down stairs plus an open loft upstairs! Thoughtfully updated to provide a true "turn-key" experience. From the moment you walk through the door, the brand-new LVP flooring creates a seamless, modern flow throughout the main living areas, leading you into a space designed for both quiet mornings and vibrant gatherings. You'll also notice brand new carpet upstairs! The heart of the home is the open kitchen and living area, but the real story unfolds in the private primary suite. The owners just completed a stunning, brand-new shower installation in the primary bath, giving you a spa-like retreat to start and end your day. If you love the Florida lifestyle, the backyard will be your favorite "room" in the house. Step outside to a fully fenced-in yard where a screened-in salt water pool awaits. Whether it's a weekend BBQ or a peaceful evening swim, this space is built for making memories. What truly sets this home apart is its placement on a premium lot. Unlike standard neighborhood footprints, this home offers an extended lot size that’s rare to find. Whether you’ve been dreaming of a lush raised-bed garden, a custom play area, or a dedicated spot for outdoor hobbyists, this oversized yard gives you the canvas to make it happen. Take peace of mind knowing that a brand new roof will be installed March 2026, HVAC & Air ducts were replaced in February 2026, pool pump was installed in 2024, AND Solar Panels will be fully paid off at closing!. Living in Kindred isn’t just about the house; it’s about the community. This master-planned neighborhood feels like a year-round vacation. You’ll have access to: Multiple Resort-Style Pools & Clubhouses, State-of-the-Art Fitness Centers, Tennis courts, multiple playgrounds, and more! Miles of scenic walking and biking trails and a dedicated dog park for your furry friends. With five true bedrooms, there is room for everyone to have their own space, while the bonus room offers the perfect flex area for a home office, gym, study, or movie room. Combined with the recent interior upgrades and the salt water pool, this home stands out as a rare find! Schedule your tour today and see why this is the one you’ve been waiting for!
Listing is courtesy of: RE/MAX TITANIUM GROUP (352-241-6363)
Listing Agent: Lauren Deem (352-275-7155)
1777 WALNUT CREEK DR, KISSIMMEE, FL 34744
$449,90031 Days on yellowkey MLS ID: O6390965
REDUCED by $9,100 (2.0%) on 04/20/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2339 Built: 2023Monthly Fee: $11 Tax: $3,358 (2025)Community: Kindred Ph 3ASpa: NoSingle Family
Taxes:$3,358
Middle School: Neptune Middle (6-8)
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!
1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744
$139,0002 Days on yellowkey MLS ID: S5148360
Bed: 2 Bath: 0.0 Liv Area Sq Ft: 1118 Built: 1973Monthly Fee: $345 Tax: $2,118 (2025)Community: Essex Park Villas CondoApartment
Taxes:$2,118
Remarks: This 2-bedroom, 2-bath home offers 1,118 square feet of comfortable living space in a highly convenient location near NeoCity and Valencia College. If you're looking for an investment opportunity, this property presents excellent potential for passive income and long-term equity growth. Inside, you'll find a spacious layout featuring two generously sized bedrooms and durable wood-look vinyl plank flooring throughout the home. The primary bathroom has been tastefully updated, adding modern appeal and functionality. The kitchen is equipped with granite countertops and stainless steel appliances, making it both stylish and practical for everyday living and entertaining. Ideally situated close to shopping, public transportation, and local schools, this home combines comfort, convenience, and value. Enjoy the balcony in the evening hours with friends and family. Don’t miss your chance to own in this desirable area.
Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)
Listing Agent: Milinda Knollinger (321-624-7384)
2988 MARBELLA DR, KISSIMMEE, FL 34744
$485,000Listed 04/23/2026 4:41PM MLS ID: S5148494
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2160 Built: 2004Monthly Fee: $167 Tax: $5,357 (2025)Community: Villa Sol Ph 2 Village 3Spa: YesSingle Family
Taxes:$5,357
Remarks: Modern finishes throughout, a fully renovated kitchen, and a resort-style pool and outdoor grill area. Located in the gated Villa Sol community and situated on over a ¼-acre lot, this beautifully maintained 4-bedroom, 2-bath home offers the perfect combination of comfort, style, and outdoor living. From the moment you arrive, you’ll appreciate the attractive landscaping, modern exterior design, and elegant double front doors with decorative glass inserts that create a warm and welcoming first impression. Step inside to a stunning dining room highlighted by gorgeous architectural columns and a striking stone accent wall that adds character and sophistication to the space. Just off the dining room, the kitchen is thoughtfully positioned for both convenience and functionality while still maintaining separation from the main entertaining areas. Designed for everyday living and hosting alike, the kitchen features all appliances included, extensive cabinet and counter space, stone countertops, tile backsplash, and a massive center island with seating—perfect for casual meals, gathering with guests, or entertaining. The living room flows seamlessly from the kitchen and is filled with natural light from oversized windows and double sliding glass doors leading directly to the pool deck, creating ideal indoor-outdoor living. Privately positioned near the front of the home, the spacious primary suite is separated from the guest bedrooms and serves as a relaxing retreat. The bedroom features abundant natural lighting, private sliding glass door access to the patio, and an en-suite bathroom complete with dual vanities, a large walk-in shower, and a garden tub perfect for unwinding at the end of the day. Additional guest bedrooms are located down a separate hallway just off the living room and offer similar layouts, comfortable sizing, and plenty of natural light throughout. Step outside to your own private backyard oasis. The oversized screened pool deck is designed for relaxation and entertaining, featuring a large in-ground pool, a separate brick paver bar area with seating, and a cozy brick fireplace accented by beautiful palm trees that create a true Florida resort-style atmosphere. The fully screened enclosure helps keep out bugs and debris while still allowing you to enjoy the sunshine and outdoor living year-round. Conveniently located near major roads, highways, shopping, dining, and attractions, residents of Villa Sol also enjoy fantastic community amenities including a clubhouse, community pool, playground, fitness center, and more—all within a private gated setting.
Listing is courtesy of: EXP REALTY LLC (407-846-0940)
Listing Agent: Steve Pugh (407-846-0940)
1720 FULFILLMENT DR, KISSIMMEE, FL 34744
$425,000Listed 04/23/2026 4:16PM MLS ID: O6401021
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2044 Built: 2022Monthly Fee: $10 Tax: $7,447 (2025)Community: Tohoqua Ph 2Single Family
Taxes:$7,447
Remarks: One or more photo(s) has been virtually staged. Welcome to this BEAUTIFULLY MAINTAINED 4-bedroom, 3-bath two-story home in the highly desirable Tohoqua community of Kissimmee, offering over 2,000 SQUARE FEET of thoughtfully designed living space. Built in 2022 and enhanced with TASTEFUL UPGRADES, this home truly FEELS LIKE NEW while offering added comfort and style throughout. From the moment you arrive, the paver walkway and CHARMING FRONT PORCH create an inviting first impression. Step inside to a spacious Living Room featuring a CUSTOM FLOOR-TO-CEILING ENTERTAINMENT CENTER (2023), providing both a stunning focal point and functional storage. The WOOD-LOOK TILE FLOORING throughout the main living areas adds durability and modern appeal, while the OPEN LAYOUT offers flexibility for both living and dining spaces. The Kitchen is bright and welcoming, featuring stainless steel appliances, a SUBWAY TILE BACKSPLASH, a closet pantry, and a breakfast bar, making it perfect for casual meals or entertaining. A MAIN-FLOOR BEDROOM and full bath provide excellent flexibility for guests, a home office, or multigenerational living. Upstairs, the Primary Suite offers a relaxing retreat, complete with a walk-in closet featuring CUSTOM STORAGE and an en suite bath with dual sinks and a step-in shower with UPGRADED SHOWERHEAD (2023). Two additional bedrooms and another full bath provide ample space for family or guests. The UPSTAIRS LAUNDRY ROOM includes a washer and upgraded dryer (2024) for added convenience. Step outside to enjoy the PRIVATE PAVER PATIO nestled between the home and detached garage, all enclosed within a NEW 6-FOOT VINYL PRIVACY FENCE (2025)—perfect for relaxing or entertaining in your own outdoor space. The garage has been upgraded with PROFESSIONAL-GRADE EPOXY FLOORING and OVERHEAD STORAGE (2022), adding both style and functionality. Additional updates include FRESH INTERIOR PAINT (2026), CEILING FANS in all bedrooms (2022), NEW EXTERIOR DOOR LOCKS (2025), and UPGRADED LED LIGHTING in all the rooms making this home truly MOVE-IN READY. Residents of Tohoqua enjoy RESORT-STYLE AMENITEIS, including a sparkling community pool, clubhouse, fitness center, tennis courts, playground, and dog park, along with scenic walking trails and green spaces throughout the neighborhood. IDEALLY LOCATED near Lake Tohopekaliga, you’ll have access to boating, fishing, and waterfront recreation, while being just a short drive from WORLD-FAMOUS ATTRACTIONS like WALT DISNEY WORLD RESORT. Shopping, dining, and everyday conveniences are close by in Kissimmee, with EASY ACCESS to major roadways such as Florida's Turnpike and U.S. Route 192 for a smooth commute throughout Central Florida. With its MODERN UPGRADES, flexible layout, and EXCEPTIONAL COMMUNITY AMENITIES, this Tohoqua home provides the perfect blend of comfort, convenience, and Florida lifestyle living. Call and schedule your showing today!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
1895 SPRING SHOWER CIR, KISSIMMEE, FL 34744
$339,0004 Days on yellowkey MLS ID: S5148149
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1559 Built: 2023Monthly Fee: $213 Tax: $1,967 (2025)Community: Tohoqua Ph 5BSpa: NoSingle Family
Taxes:$1,967
Elementary School: Neptune Elementary
High School: St. Cloud High School
Remarks: Welcome home to 1895 Spring Shower Circle where comfort meet charm. This well sought after 55+ neighborhood offers the perfect blend of modern living and timeless appeal. Features 2 bedrooms 2 full bathroom and a flex room that can be used as a third bedroom, office or den. This inviting home greets you with a beautiful yard and a warm welcoming entrance. Step inside to discover a bright open concept layout filled with natural light, a spacious living area and thoughtful finishes throughout. Whether you are entertaining in the stylish kitchen, relaxing in the cozy family room or just enjoying quiet morning on the covered patios, every space is designed for effortless living. This house was built in 2023 and the owner invested in lots of upgrades to make this home the gem it is today, such as the beautiful back splash and high cabinets in the kitchen, easy to clean diamond cut tiles for the common areas, covered patio, unique ceiling fans in every rooms, outdoor lighting, and a pest control plan than any buyer can continue if desired. The master bedroom features a spacious walk-in closet and built in shower bench in its bathroom. The bedrooms are generously sized with plenty of storage. This home is as functional as it is beautiful, not to mention the lovely pool, tennis court, dog park club house and state of the art gym. It is located within close proximity to Famous Downtown Kissimmee, access to the Turnpike, Disney and Orlando International Airport. Don't miss out on this opportunity to own a piece of this comfort and community. THE SELLER IS EXTREMELY MOTIVATED. Schedule your showing today and lets make a deal!! PLEASE NOTE , a refrigerator is included in the sale, however the refrigerator currently in the home will be replaced with a new refrigerator prior to closing. SELLER OFFERING UP TO $17,000 IN CONCESSION. ()
Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)
Listing Agent: Claudette Banton Dennis (347-876-1091)
1980 SUMMER CT, KISSIMMEE, FL 34744
$535,00029 Days on yellowkey MLS ID: O6392643
REDUCED by $14,000 (2.6%) on 04/23/2026
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 2687 Built: 2005 Tax: $6,583 (2025)Community: Meadow SpgsSingle Family
Taxes:$6,583
Elementary School: Partin Settlement Elem
Remarks: This is the kind of home multigenerational buyers wait for. Tucked at the end of a quiet cul-de-sac shared with just one other home, 1980 Summer Ct sits on over half an acre and offers a rare setup designed for living together without giving up privacy, comfort, or independence. With two full kitchens, two laundry areas, two separate two-car garages, and three full baths, this property functions beautifully for extended families, in-laws, adult children, long-term guests, or anyone needing flexible living under one roof. A spacious shared living room creates a natural central gathering space, while the home splits into two distinct wings. One side features two bedrooms, two full baths, a full kitchen, its own family room, and access to the oversized screened lanai and fully fenced backyard. The other side offers a spacious primary suite with ensuite bath, a separate family room, a second full kitchen with pantry, and its own attached two-car garage. A paid-off solar system adds even more value from day one, helping keep electric costs down. With no HOA, plenty of room to spread out, and a location near East Lake Toho, Kissimmee Lakefront Park, Shingle Creek Regional Park, Downtown Kissimmee, St. Cloud, and the theme parks, this is a rare opportunity for buyers who need space, flexibility, and a home that truly supports the way modern families live.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Shawn Layton (321-514-8055)
3589 ROCK CREEK LN, KISSIMMEE, FL 34744
$359,00079 Days on yellowkey MLS ID: S5143035
REDUCED by $5,999 (1.6%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1554 Built: 2019Monthly Fee: $138 Tax: $3,593 (2025)Community: East Lake Preserve Ph 3Single Family
Taxes:$3,593
Elementary School: East Lake Elem
High School: Tohopekaliga High School
Middle School: Narcoossee Middle
Remarks: MOVE IN READY! Welcome to this 3-bedroom, 2-bath home with a versatile flex room, located in the quiet and established community of East Lake Preserve. This inviting home offers an open-concept layout perfect for both everyday living and entertaining. Enjoy spacious living areas filled with natural light, comfortable bedrooms, and a functional floor plan that flows effortlessly throughout the home. The kitchen flows seamlessly into the living and dining spaces — ideal for gatherings, family time, and making lasting memories. The flex room provides endless possibilities — whether you need a home office, playroom, gym, or additional living space. Step outside for morning coffee, weekend barbecues, or simply soaking in Florida’s year-round sunshine. Beyond the home, enjoy resort-style community amenities including a pool, playground, walking trails, dog park, and the convenience of internet included with the HOA. This home includes a solar panel system designed to keep energy costs down while supporting a more efficient lifestyle. Conveniently located near Lake Nona, Medical City, VA Hospital, USTA National Campus, Austin-Tindall Sports Complex, Orlando International Airport, major highways, and top-rated schools. Whether you’re a first-time buyer, growing family, or looking for a smart investment, this home offers perfect combination of comfort, location, and value. SOLAR PANELS TO BE PAID IN FULL AT CLOSING— buyer will receive the system FREE AND CLEAR with no remaining balance. Buyer may also receive up to $1,500 in lender credit when using the seller’s preferred lender. Don’t miss the opportunity to make this home yours — schedule your private showing today!
Listing is courtesy of: THE DISTRICT REAL ESTATE OF FLORIDA (407-362-7738)
Listing Agent: Yesenia Vargas (407-775-9874)
1516 PINE ISLAND RD, KISSIMMEE, FL 34744
$875,00028 Days on yellowkey MLS ID: S5145674
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2613 Built: 2026 Tax: $1,385 (2025)Community: Regal Point Estates Unit 1Single Family
Taxes:$1,385
Remarks: One or more photo(s) has been virtually staged. Welcome to your private slice of Florida living—where space, style, and convenience come together on a generous .86-acre homesite. Striking contemporary elevation with clean architectural lines and elegant stone accents, creating a timeless yet modern curb appeal. Large windows enhance the exterior design while bringing in natural light, and an inviting entryway. Open-concept layout highlighted by a gourmet kitchen with quartz countertops, built-in oven, glass cooktop, plenty of room for your coffee station, and a spacious closet pantry. The living area opens through large sliding glass doors to a covered rear porch, perfect for indoor-outdoor living. Enjoy added convenience with a mudroom entry from the garage, an inside laundry room, and tile flooring throughout the entire house. Situated near Lakefront Park, Neo City, with easy access to the Florida Turnpike.
Listing is courtesy of: KEN BAKER REAL ESTATE (407-846-0063)
Listing Agent: Kenneth Baker (407-846-0063)
2540 WINNERS CIR, KISSIMMEE, FL 34744
$739,00063 Days on yellowkey MLS ID: O6382446
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 3246 Built: 2000 Tax: $3,688 (2025)Community: Winners ParkSpa: NoSingle Family
Taxes:$3,688
Remarks: **WELCOME HOME** NO HOA, HALF AN ACRE of land, a PRIVATE POOL, and a full SEPARATE APARTMENT on the main floor – welcome to your next chapter on Winners Circle in the Winners Park community of Kissimmee! EXTERIOR PAINT (2023), NEW WINDOWS (2022), DETACHED AIR CONDITIONED GARAGE (2022), septic tank serviced (2022) – big-ticket items are already started, giving you confidence and flexibility from day one. Situated on an expansive .50 ACRE LOT, this spacious two-story POOL HOME delivers over 3,000 square feet of living space, mature landscaping, a TILE ROOF, long paver driveway, and standout curb appeal. The SCREENED POOL with PAVER DECK creates a private backyard retreat with room to entertain, garden, or just spread out. Inside, the flexible layout is ideal for large households, multi-generational living, or anyone needing versatile space. The full first-floor apartment includes its own kitchen open to a living area, bedroom, and full bath – perfect for in-laws, guests, extended stays, or even creative work from home options! The main home features comfortable formal and family spaces, a well-equipped kitchen with casual dining, and an expansive FLORIDA ROOM complete with a full bath and cozy office space – offering endless possibilities for hobbies, remote work, or additional entertaining. Upstairs, a BONUS/LOFT anchors the remaining bedrooms, while the generous PRIMARY SUITE provides a peaceful escape with an updated private en-suite bath. Car enthusiasts, hobbyists, or entrepreneurs will appreciate the two-car attached garage plus the like-new detached, air-conditioned garage – currently used as a dojo, but easily transformed into a workshop, craft studio, gym, or business space. Updated yet still offering room to personalize, this home offers the rare combination of space, privacy, flexibility, and location. Perfectly situated just off Simpson Road, you will enjoy easy access to the Florida Turnpike, shopping, dining, area lakes, attractions, and world-famous theme parks – all while coming home to a quiet, established neighborhood with no HOA restrictions. Room to grow inside and out. Versatility for today and tomorrow. Schedule your tour today and be the winner on Winners Circle! **Seller may consider buyer concessions if made in an offer**
1895 HICKORY BLUFF RD, KISSIMMEE, FL 34744
$349,90093 Days on yellowkey MLS ID: S5142089
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 2017Monthly Fee: $11 Tax: $6,019 (2025)Community: Kindred Ph 1C Pb 25 Pgs 127-134 Lot 373Spa: NoSingle Family
Taxes:$6,019
Remarks: This charming 3-bedroom, 2-bath home features a spacious backyard perfect for entertaining and family gatherings. Ideally located in a central, convenient area, just steps from main avenues, shopping centers, restaurants, and gas stations, and only 1 mile from Florida Turnpike and US-192. Residents enjoy access to community amenities including swimming pools, fitness centers, walking trails, tennis courts, and social spaces, providing the perfect balance of active living and relaxation. With move-in ready comfort, style, and plenty of space, this home is perfect for embracing the Florida lifestyle. Motivated sellers—ready for you to move in today!
Listing is courtesy of: REALTY ONE GROUP MAGIC CITY (407-589-9080)
Listing Agent: Elsie Cruz (407-561-4957)
100 THORNBURY LN, KISSIMMEE, FL 34744
$440,000226 Days on yellowkey MLS ID: O6342537
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2379 Built: 2002Monthly Fee: $13 Tax: $3,689 (2024)Community: Remington Prcl H Ph 2Single Family
Taxes:$3,689
Tax Year: 2024
Remarks: Huge Price Drop! Seller is highly motivated! Welcome to this spacious and well-appointed two-story home located in the sought-after Remington Gold Club Community. Offering 4 bedrooms, 3 full bathrooms, and 2,379 sqft of living space, this property combines comfort, convenience, and style. Key features: -Versatile layout: first floor includes a private bedroom and full bath-perfect for guests or multigenerational living. -Modern upgrades: New A/C (2021) and roof (2022) for peace of mind. The updated kitchen features granite countertops. -Luxurious Master Suite: Upstairs master bedroom boasts a beautifully renovated oversized shower and upgraded flooring throughout the second level. -Outdoor Living: Fully fenced backyard and a 2-car garage provide privacy and functionality. Community Amenities: -Gated golf course community with pool, playground, and on-site daycare. -Easy access to Florida Turnpike, just minutes from Walt Disney World, East Lake Tohopekaliga, and major retail centers including Publix, Home Depot, and nearby hospitals. Don't miss this opportunity! Schedule your private showing today and discover the lifestyle that awaits in Remington!
Listing is courtesy of: DOVER INTERNATIONAL CO., INC. (407-333-0711)
Listing Agent: Armelio Fernandez Aponte, Sr (407-720-1664)
2533 OAK RUN BLVD, KISSIMMEE, FL 34744
$397,00070 Days on yellowkey MLS ID: S5143776
0 Days Off yellowkey (back on 3/16/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1661 Built: 1986 Tax: $5,386 (2025)Community: Oak Run Unit 3Spa: NoSingle Family
Taxes:$5,386
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. No HOA, Fully Renovated and Ready to Impress! This home has been extensively updated with a focus on clean design, modern finishes, and improved floor plan flow. Both the interior and exterior have been freshly painted, creating a crisp, cohesive look from the curb all the way through the interior. Inside, all flooring has been replaced with new waterproof vinyl, complemented by brand-new baseboards throughout for a sharp, finished feel. Walls were removed to open up the main living areas, allowing the front living room, dining space, and redesigned kitchen to connect seamlessly. The kitchen now features new cabinetry, new countertops, and all brand-new stainless steel appliances, giving the space a streamlined and functional layout that anchors the home. Toward the back, a separate living room offers additional flexibility and a wood-burning stone fireplace adds character and warmth. Sliding doors lead from this space to the expansive 23’ x 10’ covered and screened porch, extending the living area outdoors and providing an ideal setting for relaxing or entertaining year-round. Both bathrooms have been completely renovated with new cabinets, new countertops, updated fixtures, and modern finishes. The yard is fully fenced and the front landscaping has been refreshed following the recent freeze to enhance curb appeal. The garage features finished flooring, adding to the clean, well-maintained presentation. Major systems have been addressed as well, including a roof replaced in 2018 and an A/C system replaced in 2020. The water heater was replaced in 2012. Walking distance to many shops, schools and services this home is also located just a few minutes drive from Florida’s Turnpike, approximately 15 minutes to Orlando International Airport, and about 25 minutes to Disney parks and downtown Orlando. This home combines extensive upgrades with an exceptionally central Kissimmee location. Completely updated, thoughtfully redesigned, and on the market for the first time in four decades, 2533 Oak Run Blvd delivers modern living without HOA restrictions in a well-established neighborhood.
Listing Agent: Irena Aistrop (321-443-7535)
107 BENITA STREET, KISSIMMEE, FL 34744
$150,000533 Days on yellowkey MLS ID: O6255238
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1010 Built: 1965 Tax: $1,221 (2024)Community: Roy WellsMobile Home
Taxes:$1,221
Remarks: PRICE REDUCTION! PRICE REDUCTION! RARE FIND - YOU OWN THE LAND, NO LOT RENT, NO PARK RULES, NO HOA, JUST A SOLID MOBIL HOME ON IT'S OWN OVERSIZED LOT WITH CITY WATER AND CITY SEWER, ROOM FOR YOUR TOYS, AND PLENTY OF SPACE TO EXPAND. PRICE REDUCTION, BACK ON THE MARKET.. - CASH ONLY. - NEARLY 1/4 ACRE! 3 BEDROOMS / 1 BATHROOM, - NO WELL OR SEPTIC HASSLES. NO CARPET! - CLEAN, EASY MAINTANANCE FLOORING THROUGHOUT, BRAND NEW APPLIANCES MOVE IN READY, FULLY FENCED YARD - PERFECT FOR PETS AND PRIVACY, - YOU OWN THE LAND! CLOSE TO SHOPPING & ESSENTIALS - CONVENIENCE AT YOUR DOOR STEP! DONT MISS OUT. SCHEDULE YOUR SHOWING TODAY.
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: John Castillo (321-436-7758)
1336 E LAKE SHORE BLVD, KISSIMMEE, FL 34744
$359,999Listed 04/23/2026 9:26AM MLS ID: A4691089
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1450 Built: 1963 Tax: $2,633 (2025)Community: Ocean Gulf Estates Sec 1Single Family
Taxes:$2,633
Remarks: This 3 bed/2 bath home offers 1,400 sq ft of practical living space on a spacious 0.34-acre lot, directly across the street from Lake Toho for added lifestyle appeal. The main living areas feature durable LVT flooring, while the kitchen includes wooden cabinetry, laminated countertops, stainless steel appliances, and a granite top breakfast bar for everyday convenience. Bedrooms also feature LVT flooring and built-in double door cabinets, with both bathrooms offering tile flooring, under sink storage, and medicine cabinets. A dedicated laundry room adds functionality. Outside, the property includes a 2-car garage, front patio, and a wide, fenced backyard ideal for gardening or gatherings. Enjoy a covered swimming pool with lanai for year-round use, plus a storage shed for additional space. A well-rounded property offering solid features, outdoor space, and a prime location.
Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)
Listing Agent: Scott Fader (248-294-7850)
2605 PLAY HARD ALY, KISSIMMEE, FL 34744
$375,00066 Days on yellowkey MLS ID: S5143916
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1603 Built: 2019Monthly Fee: $154 Tax: $4,220 (2025)Community: Tohoqua Ph 1Townhouse
Taxes:$4,220
Remarks: Prepare to be impressed! Step inside and you can instantly feel the embrace of this stunning Mattamy Thownhouse. As you enter, you'll be greeted by an open floor plan, flooded with natural light, this 3 bed and 2.5 bath is been recently paint and so many upgrades that create a relaxing atmosphere. The kitchen it's a dream with stunning quartz countertops the thoughtful design continues with the backsplash adding a touch of elegance. Recessed lighting throughout the house that add more warmth. The open floor plan flows into the living area creating a perfect space to enjoy the stunning accent tv wall, designed to be the focal pointof your entertaiment area. The master suite includes a bonus loft area, perfect spot for a home office, library, or whatever suits your lifesyle. You'll have the space you need, you'll also find a clean, spacius two car garage with plenty room for storage , Ev charger installed for your electric vehicle ready to go, water softener, modern electric blinds, new laminate floor. But that is not all!! You will love living in Tohoqua, a community offering a resort style swimming pool, a club house, tenis court and beautiful walking trails. It is a lifestyle , not just a home. What are you waiting for? Call and make an appoiment today.
Listing is courtesy of: MAGIC HOMES REALTY LLC (407-436-4176)
Listing Agent: Shirley Portugal Rivera (407-247-5095)
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