Location: Kissimmee
Keyword(s): Osceola County School For Arts
Keyword(s) High School: Osceola County School For Arts
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1214 CHEROKEE CT, KISSIMMEE, FL 34744
$289,00052 Days on yellowkey MLS ID: O6390987
1 Days Off yellowkey (back on 4/13/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1600 Built: 1976 Tax: $3,877 (2025)Community: Oak Grove EastSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,877
Elementary School: Mill Creek Elem (K 5)
High School: Osceola County School for Arts
Tax Year: 2025
Middle School: Denn John Middle
Remarks: Discover the opportunity at 1214 Cherokee Court in the heart of Kissimmee! Tucked away on a quiet cul-de-sac, this property offers the perfect blend of privacy, flexibility, and location — just minutes from world-famous attractions including Walt Disney World, Universal Orlando Resort, and SeaWorld Orlando. This home is ideal for homeowners and investors alike, featuring NO HOA and NO RENTAL RESTRICTIONS, giving you the freedom to live in it full-time, use it as a vacation home, or maximize income potential with short-term or long-term rentals. Enjoy convenient access to major roadways, shopping, dining, schools, and Orlando International Airport, all while being just a short drive to Central Florida’s top entertainment destinations. Whether you're looking for a primary residence, second home, or income-producing property, this location delivers unmatched versatility and value. Don’t miss your chance to own a property with flexibility, freedom, and a prime location close to everything buyers and guests are looking for!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Jessica Brown (407-452-7700)
1030 PLANTATION DR #C7, KISSIMMEE, FL 34741
$175,00083 Days on yellowkey MLS ID: O6388527
0 Days Off yellowkey (back on 5/25/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 970 Built: 1970 Tax: $316 (2024)Community: Terra CondoCondo
Taxes:$316
Elementary School: Thacker Avenue Elem (K 5)
Tax Year: 2024
Middle School: Kissimmee Middle
Remarks: Welcome Home to Comfort and Convenience in Terra Condo! Step inside this beautifully updated 2-bedroom, 2-bathroom condo nestled in the gated Terra Condo community, where comfort meets low-maintenance living! From the moment you enter, you’ll love the stylish tile flooring that flows seamlessly throughout, giving the home a clean and modern touch. The charming kitchen features beautiful countertops, stainless steel appliances, and plenty of space to whip up your favorite meals. The spacious primary bedroom offers dual closets—perfect for keeping everything neatly organized. Unwind after a long day on your screened-in porch, ideal for enjoying peaceful evenings or your morning coffee. Additional highlights include a tankless water heater, low HOA fees, and a prime Kissimmee location—just 15 minutes from The Loop, 25 minutes from world-famous theme parks, and 30 minutes from Orlando International Airport. This move-in-ready gem has everything you need for easy Florida living—schedule your showing today before it’s gone!
Listing Agent: Jessica Collins (386-564-0120)
3051 GREYSTONE LOOP #302, KISSIMMEE, FL 34741
$235,00038 Days on yellowkey MLS ID: O6400559
2 Days Off yellowkey (back on 5/24/2026)
REDUCED by $5,000 (2.1%) on 05/11/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1634 Built: 2006Monthly Fee: $390 Tax: $2,534 (2025)Community: Flora Ridge Condo Ph 2 Bldg 5Condo
Taxes:$2,534
Elementary School: Floral Ridge Elementary
Remarks: Under contract-accepting backup offers. One of the largest floorplans in Flora Ridge, offering over 1,600 sq ft of flexible living space in a gated community just minutes from The Loop, Osceola Parkway, and under 10 miles to Disney. This 3-bedroom, 2-bath condo is ideally positioned on the 3rd floor with elevator access and features a versatile bonus space off the primary suite—perfect for a home office, nursery, or potential 4th bedroom. The split floorplan creates privacy while still feeling open and functional. Inside, the home has been thoughtfully upgraded with modern finishes throughout. The kitchen stands out with upgraded cabinetry, stainless steel appliances, stone countertops, recessed lighting, and a custom Ambrosia Maple butcher block. Additional upgrades include a remodeled walk-in pantry, laminate flooring throughout, Alexa-enabled smart lighting and thermostat, USB outlets, and a sleek floating entertainment system in the living room. Custom Elfa closet systems and built-in dining banquette seating add both style and storage. Updated with high-performance vinyl replacement windows, featuring durable double-pane glass for improved energy efficiency, insulation, and noise reduction. Standard double-hung design allows for easy operation and maintenance. Step outside to a screened-in balcony, ideal for enjoying fresh air year-round. The unit also includes a ventless washer and dryer, allowing flexibility in placement, along with ceiling fans in every room. The exterior of this community was renovated with new balcony, paint and screens added. Additional highlights include a newer AC, covered parking spaces, and ample guest parking. Offsite security guard access.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Meagan Waddell (321-945-0008)
2925 WILLOW CREEK LN, KISSIMMEE, FL 34741
$415,00041 Days on yellowkey MLS ID: C7525014
REDUCED by $10,000 (2.4%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1797 Built: 2004Monthly Fee: $80 Tax: $6,773 (2025)Community: Windsor Point Ph 2Single Family
Taxes:$6,773
Remarks: Welcome home to this well-maintained single-family residence offering a bright and functional layout. The interior features spacious living and dining areas with tile flooring throughout the main living spaces and an open flow ideal for everyday living and entertaining. Comfortable bedrooms offer carpeting and ceiling fans, while the master bedroom has sliding doors leading to your rear screened-in lanai. Additional features include a two-car garage and a clean, neutral interior ready for its next owner. Easy to show!
Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)
Listing Agent: William Figueroa (305-662-1502)
2331 W OAK ST, KISSIMMEE, FL 34741
$335,00029 Days on yellowkey MLS ID: O6403087
0 Days Off yellowkey (back on 5/16/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1335 Built: 1956 Tax: $4,265 (2025)Community: Orange Gardens Sec 1Single Family
Taxes:$4,265
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. NO HOA, a NEWER ROOF and UPDATED WINDOWS, EFFICIENCY/Mother in law Suite – this versatile single story Orange Gardens home is an opportunity you don’t want to miss! The flexible layout of 4-bedrooms and 2-baths opens the door to multi-generational living, rental income, or a private work-from-home setup. Set on a spacious .19 ACRE LOT in an established community just off US-192, this home delivers easy access to shopping, dining, area lakes, resort destinations, and is just minutes to Walt Disney World Resort. Front and rear porches overlook generous yard space with plenty of room to relax, entertain, or expand. Inside, you will find TERRAZZO FLOORING throughout and a light-filled layout featuring OPEN LIVING & DINING spaces that flow easily into a galley-style kitchen complete with a fresh neutral palette, solid surface countertops, and ample cabinet storage. Just off the main living area is a light filled FLEX/OFFICE space, ideal for remote work, hobbies, or additional living space. The main portion of the home offers three bedrooms situated on one side, sharing a full bath for a functional and traditional layout. What truly sets this home apart is the BONUS/EFFICIENCY/IN-LAW SUITE with a PRIVATE ENTRANCE off the kitchen, WALK-IN CLOSET, and FULL BATH – perfect for extended family, guests, or income-producing potential. Whether you are looking for a first home to make your own or a smart investment property in a high-demand location near Disney and Central Florida attractions, this home checks all the boxes with space, flexibility, and location. Call today to schedule a tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
2664 HORSESHOE BAY DR, KISSIMMEE, FL 34741
$392,500183 Days on yellowkey MLS ID: O6363343
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1959 Built: 1988Monthly Fee: $75 Tax: $4,773 (2024)Community: Bermuda BaySingle Family
Taxes:$4,773
Elementary School: Highlands Elem
Remarks: This stunning home offers an exceptional blend of modern comfort and convenience. The primary suite (including updated bathroom) is conveniently located on the main floor, providing privacy and ease of access. The well-equipped GOURMET KITCHEN is perfect for cooking and entertaining, and flows seamlessly into the OPEN-CONCEPT living and dining areas. Ample natural light enhances the home's spacious feel. Outside, enjoy a FENCED-IN BACKYARD with a large wrap around SCREENED-IN PATIO, ideal for relaxation or gatherings. Recent upgrades include a NEWER ROOF (2020), HVAC (2022), and UPDATED ELECTRICAL PANEL and WATER HEATER (2023) bring lasting peace of mind. Storage is plentiful with generously sized closets throughout. Located across the street from the community pool, this home is also close to parks and major highways, ensuring easy access to recreation and commuting. Solar panels provide eco-friendly energy efficiency, making this a perfect move-in-ready home.
Listing Agent: Mark Vescio (678-895-2631)
1730 NEPTUNE RD, KISSIMMEE, FL 34744
$490,000129 Days on yellowkey MLS ID: S5141897
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2178 Built: 1964 Tax: $713 (2025)Community: Neptune Shores 1Single Family
Taxes:$713
Elementary School: Partin Settlement Elem
Middle School: Neptune Middle (6-8)
Remarks: This property is a unique find for a buyer with a vision, offering a rare blend of convenience and botanical charm. Built in 1964 and situated on just over 0.98 acres, this home is perfectly positioned on Neptune Road—placing you right between the hearts of Saint Cloud and Kissimmee. Commuters will love being just two miles from the Florida Turnpike, providing easy access to Orlando and the coast. The lot itself is a private sanctuary, featuring a convenient looped driveway with two entrances and a lush landscape teeming with life. From the beauty of Golden Chain trees and Rain Lilies to a literal "food forest" of avocado, pineapple, guava, and papaya, the outdoor space is an incredible canvas for gardeners or those seeking a peaceful retreat. Inside, the home offers a spacious layout that is ready for your personal touch. Entry begins through a screened front porch leading into a massive living and dining combo that offers access to the enclosed area that was once a green house through multiple sliding glass doors. The kitchen features newer Ikea cabinets, and solid counter tops. Beyond the main living area, you'll find a family room that opens to an enclosed lanai and a bonus room and access the backyard. The main floor hosts the primary suite featuring a private bathroom en-suite with walk-in shower, as well as 2 additional bedrooms and another full bathroom with shower/tub combo. Adding to the property's potential is a separate upstairs area with its own private entrance, featuring a large living area and its own full bathroom. While the home requires some TLC and updates, the "bones" of the property—including the one-car garage with ample storage and an additional room with two access doors to the front and side yards - allows for endless possibilities. If you are looking for a project with great "roots" in a prime location, come take a look and imagine the potential this mini-estate holds!
Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)
Listing Agent: Kristin Bearce (407-361-6853)
2920 ASHLAND LN S, KISSIMMEE, FL 34741
$330,00037 Days on yellowkey MLS ID: O6400955
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1957 Built: 2005Monthly Fee: $240 Tax: $4,098 (2025)Community: Townhomes Of Flora RidgeTownhouse
Taxes:$4,098
Remarks: Welcome to this exceptional townhome located in the desirable Townhomes of Flora Ridge community of Kissimmee, Florida. The interior features beautiful tile flooring throughout and is designed for easy, low-maintenance living. The open floor plan is well planned out and feels larger than it is. The first floor includes a spacious kitchen that perfectly blends comfort and style. The primary bedroom is on the second floor, serving as a relaxing retreat highlighted by a spacious bathroom and a walk in closet. For your comfort in any season, the home is equipped with central air conditioning and ceiling fans. The staircase comes with a handicap accessible elevator. Outside, this residence boasts stucco construction and includes a one-car attached garage for added convenience and security. Residents will benefit from the well-maintained nature of the community. The property is near Flora Ridge Elementary, Kissimmee Middle, and the Osceola County School for the Arts. The community has a pool as well as a walking path around a beautiful lake.
Listing Agent: Nicholas Feinsod (407-607-7485)
2050 E IRLO BRONSON MEMORIAL HWY #108, KISSIMMEE, FL 34744
$49,000168 Days on yellowkey MLS ID: O6366840
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 324 Built: 1973Monthly Fee: $500 Tax: $846 (2025)Community: Heritage Park InCondo
Taxes:$846
Remarks: Welcome to your magical home base in the heart of Orlando! This stylish, fully equipped condo hotel is located just minutes from the Disney parks, making it the ideal spot for families, couples, and park-hoppers looking for comfort, convenience, and great value. This condo at Heritage Park In is zoned for short term rentals only. Seller is financing with 1/2 down + 24 x with low APR. Features: Bright, modern studio with a cozy bed. Kitchenette with microwave, mini-fridge, coffee maker, and essentials; Smart TV with streaming apps; Fast Wi-Fi for work or entertainment Amenities: Free parking, outdoor pool and on-site laundry facility. Utilities, internet, cable Tv and maintenance are included with HOA fee.
Listing is courtesy of: ALLIANCE REAL ESTATE GROUP (407-375-8680)
Listing Agent: Marcia Abe (973-342-4491)
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