34744 Homes under $500,000

34744 Homes under $500,000

Welcome to the enchanting world of Kissimmee, Florida, where the zip code 34744 is your gateway to a vibrant community filled with charm and opportunity. Nestled in the heart of Osceola County, this area is renowned for its family-friendly atmosphere, rich history, and proximity to some of Florida's most popular attractions.

Kissimmee offers a delightful blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and young professionals alike. You'll find a variety of parks, recreational facilities, and shopping centers that cater to every lifestyle. The stunning natural beauty of nearby lakes and nature reserves provides endless opportunities for outdoor adventures, from fishing and boating to hiking and picnicking.

One of the most appealing aspects of the 34744 area is the availability of homes priced under $500,000. This makes it an excellent choice for first-time homebuyers and those looking to invest in a growing market. Whether you’re searching for a cozy single-family home, a modern townhouse, or a spacious condo, Kissimmee has something to suit every taste and budget. Many homes in this price range boast contemporary designs, updated amenities, and inviting outdoor spaces perfect for entertaining or relaxing.

Living in Kissimmee means enjoying a warm, sunny climate year-round and easy access to world-famous attractions like Walt Disney World and Universal Studios. With its rich cultural heritage and diverse community, the 34744 zip code is not just a place to live—it's a place to thrive. Come discover your dream home in Kissimmee today!

Newest 34744 Homes under $500,000

2502 Crown Ridge Circle, Kissimmee
$375,000
4 Beds ⋅ 2 Baths ⋅ Remington Prcl H Ph 1 SubDv. ⋅ 34744 Zip Code
THIS 4 BED 2 BATH HOME IN THE GATED GOLF COMMUNITY OF REMINGTON IS LOOKING FOR A NEW OWNER. SITUATED IN A QUIET CIRCLE OF THE MAIN REMINGTOM BLVD THE HOUSE COMES WITH NO REAR NEIGHBOURS. THIS IS AN OPEN SPLIT FLOORPLAN WITH A LANAI AND FLORIDA ROOM TO THE REAR. THE HOUSE COMES WITH CERMAMIC TILE THROUGHOUT THE HOUSE TO HELP COOL AND FOR EASY CLEANING. THE CURRENT OWNER REPLACED THE HOTWATER TANK WITH A TANKLESS SYSTEM GIVING HOT WATER ON DEMAND THUS REDUCING YOUR ELECTRIC BILL. THE A/C HAS BEEN REPLACED WITH AN UPGRADED SYSTEM BOTH INSIDE AND OUT. THE DRIVE WAY IS ONE OF THE FEW ON THE ROAD WITH BRICK PAVERS WHICH ADDS TO THE CURB APPEAL. WITH A LITTLE TLC THIS HOUSE COULD BE A PALACE IN THE MAKING. SCHEDULE A VIEWING AND LET YOUR IMAGINATION RUN RIOT.

2502 Crown Ridge Circle, Kissimmee
2963 Sera Bella Way, Kissimmee
$500,000
3 Beds ⋅ 3 Baths ⋅ Sera Bella SubDv. ⋅ 34744 Zip Code
A 3-bed single family residence in Sera Bella with water views, a private entrance in-law suite, and potential 4th bedroom flexibility is hard to find in Kissimmee. This 2-story home offers 2,416 heated square feet, 2.5 baths, a 2-car garage, pond views with fountains and lights, and access to Sera Bella community amenities. This beautifully maintained home in Kissimmee’s 34744 area delivers the space, layout, and location buyers want. The inviting exterior features a brick paver driveway, covered entry, landscaped curb appeal, sidewalks, and an attached 2-car garage. Inside, the bright floor plan offers ceramic tile flooring, formal dining, a spacious living room, and a comfortable family room that flows naturally into the kitchen. The kitchen features granite counters, stainless steel appliances, a center island, closet pantry, stone counters, and generous workspace for everyday meals or entertaining. One of the home’s most valuable features is the attached in-law suite with a kitchenette, studio layout, and private entrance, creating added flexibility for guests, extended stay needs, a work-from-home setup, or a private retreat. Upstairs, the primary suite offers tray ceilings, a walk-in closet, dual sinks, granite counters, a garden bath, and a separate shower. Two additional bedrooms, an upstairs laundry room, and a spacious loft complete the second floor. The loft has excellent potential to become a 4th bedroom, with an existing built-in area intended for a closet. The covered, enclosed, screened rear porch overlooks the pond, where fountains and evening lights create a peaceful backdrop for relaxing or entertaining. Convenient to Lake Nona, Medical City, shopping, dining, major roads, Orlando International Airport, and Central Florida attractions.

2963 Sera Bella Way, Kissimmee
1516 Kelby Road, Kissimmee
$289,900
3 Beds ⋅ 2 Baths ⋅ Shenandoah SubDv. ⋅ 34744 Zip Code
Welcome to 1516 Kelby Road in Kissimmee! This 3-bedroom, 1.5-bathroom single-family home offers approximately 1,321 square feet of living space on a 5,227-square-foot lot in the established Shenandoah community. The home features a functional layout, central air conditioning, ceiling fans and a combination of carpet, tile and laminate flooring. The property also offers a converted garage for additional flexible space and a paved road for convenient access. With no HOA, this home provides added flexibility for its next owner. Conveniently located near US-192, major roadways, shopping, dining and everyday conveniences. Schedule your showing today!

1516 Kelby Road, Kissimmee
1437 Tawny Ridge Road, Kissimmee
$414,900
4 Beds ⋅ 2 Baths ⋅ Kindred Ph 1fa SubDv. ⋅ 34744 Zip Code
SOLAR PANELS TO BE PAID OFF AT CLOSING BY SELLER + WHOLE-HOUSE WATER FILTRATION SYSTEM INCLUDED! Welcome to this spacious 4-bedroom, 2-bath single-story home in the desirable Kindred community. Designed for comfortable everyday living, the home features a bright open-concept floor plan, tile flooring throughout the main living areas, and a modern kitchen with stainless steel appliances, ample cabinetry, and generous space for cooking, gathering, and entertaining. A major added benefit: the solar panel system will be paid off by the seller at closing, allowing the buyer to enjoy the system without assuming the seller's solar loan. The home also includes a whole-house water filtration system. Property is currently listed for both sale and lease. Seller intends to proceed with whichever transaction is secured first. Please contact listing agent for current availability prior to submitting an proposal. Step outside to a fully fenced backyard offering privacy and plenty of space to relax, entertain, or enjoy the Florida lifestyle. Kindred offers resort-style amenities including community pools, fitness center, clubhouse, tennis and pickleball courts, playgrounds, dog park, and scenic walking trails. Conveniently located with easy access to the Florida Turnpike, Orlando International Airport, Lake Nona, shopping, dining, schools, major employment areas, and Central Florida attractions. A wonderful combination of space, energy-conscious features, outdoor privacy, and resort-style community living—ready for its next owner!

1437 Tawny Ridge Road, Kissimmee
1512 Fernmeadow Street, Kissimmee
$360,000
3 Beds ⋅ 2 Baths ⋅ Kindred Ph 2c & 2d SubDv. ⋅ 34744 Zip Code
Welcome to 1512 Fernmeadow Street in the desirable Kindred community. This nearly new DR Horton Jemison floorplan features an open layout with a bright great room, stainless steel appliances, an oversized walk-in pantry, and smart home features. The private primary suite offers an ensuite bath with double vanity and walk-in closet, while two additional bedrooms provide space for guests, an office, or flexible living. Kindred offers resort-style amenities including pools, clubhouses, a fitness center, playgrounds, sports fields, a dog park, picnic areas, and walking and biking trails. Conveniently located near US-192 and Florida’s Turnpike, with easy access to NeoCity, Lake Nona, Orlando International Airport, Disney, shopping, dining, and downtown Kissimmee. Enjoy low-maintenance living with great amenities and convenient access to everything Central Florida has to offer.

1512 Fernmeadow Street, Kissimmee
1733 Felicity Lane, Kissimmee
$419,900
4 Beds ⋅ 3 Baths ⋅ Tohoqua Ph 1 SubDv. ⋅ 34744 Zip Code
Welcome to 1733 Felicity Ln, a beautifully designed single-story Mattamy Homes residence located on a desirable corner lot in Tohoqua, one of Kissimmee’s sought-after master-planned communities. With approximately 2,740 total building sq ft, this home combines space, flexibility, energy-conscious features, and an excellent Central Florida location. The thoughtfully designed floor plan features 4 bedrooms and 3 full bathrooms, including a private guest suite configuration with its own full bath—an excellent option for overnight guests, multigenerational living, a private workspace, or added everyday flexibility. The open-concept kitchen, dining, and gathering areas create a natural flow for daily living and entertaining, while the extended screened lanai expands the living experience outdoors. A welcoming covered front porch and the additional privacy and presence of a corner lot further enhance the home’s appeal. Additional features include a solar energy system and whole-house water filtration system, adding practical value for buyers looking for efficiency-focused home features. The spacious layout, guest suite, outdoor living area, and corner-lot setting also make this property attractive to buyers and investors seeking a versatile single-family home in the growing Kissimmee–St. Cloud corridor. Tohoqua residents enjoy resort-style community amenities including a zero-entry pool, clubhouse, fitness center, playground, lighted tennis courts, basketball court, sidewalks, outdoor gathering areas, and an extensive network of walking and biking trails. The community also provides convenient access to Florida’s Turnpike, shopping, dining, NeoCity, Lake Nona, Orlando International Airport, and the many employment, recreation, and entertainment destinations throughout Central Florida. **The property has an existing mortgage that may be assumable by a qualified buyer, subject to lender approval, underwriting, existing loan terms, and all applicable requirements..** Discover the combination of space, location, lifestyle, and flexibility that makes 1733 Felicity Ln stand out. Schedule your private showing today and see how this home can fit your next chapter.

1733 Felicity Lane, Kissimmee
1112 Ocean Street, Kissimmee
$425,000
6 Beds ⋅ 4 Baths ⋅ Kissimmee Heights SubDv. ⋅ 34744 Zip Code
Exceptional Investment Opportunity! NO HOA! This turnkey investment offers immediate cash flow with excellent long-term appreciation potential. Both units are occupied by the great tenants; they stay there more than 5 years and would like to stay longer. 2 bedroom (the garage was upgraded to the 3rd bed) 2 bath, ceramic tile through the whole house with easy maintenance,2024 new roof…An outstanding opportunity to add a well-maintained, income-generating asset to your investment portfolio, offering stable rental income, a prime location, and excellent potential for future value appreciation in one of Florida's fastest-growing real estate markets.

1112 Ocean Street, Kissimmee
1852 Summer Serenity Drive, Kissimmee
$350,000
3 Beds ⋅ 3 Baths ⋅ Tohoqua Ph 4a SubDv. ⋅ 34744 Zip Code
Short Sale. Welcome home to this 3 bedroom, 2.5 bathroom home located in the desirable Tohoqua community in Kissimmee! Offering a functional two story layout, beautiful pond views, and comfortable living spaces, this home is designed for both everyday living and entertaining. The main level features tile flooring throughout the living areas and an open, welcoming layout. The kitchen is equipped with granite countertops, stainless steel appliances, ample cabinet space, and a large pantry for additional storage. A convenient half bathroom is located downstairs for guests. Sliding glass doors extend the living space outdoors to a covered paver patio overlooking the pond, creating a relaxing spot to unwind and enjoy the peaceful water views. Upstairs, a landing at the top of the stairs provides additional space along with a convenient storage closet. All three bedrooms are located on the second floor, including the spacious primary suite featuring a walk in closet and an en suite bathroom with a dual sink vanity and stand up shower. The two additional bedrooms share the hall bathroom, which features a large vanity and tub/shower combination. An indoor laundry room with a utility sink is also conveniently located upstairs near the bedrooms. Additional features include a two car garage and a Rain Bird irrigation system. Located in the sought after Tohoqua community with convenient access to shopping, dining, schools, major roadways, and all that the Kissimmee area has to offer. Schedule your private showing today!

1852 Summer Serenity Drive, Kissimmee
2578 Autumn Peace Drive, Kissimmee
$469,500
3 Beds ⋅ 2 Baths ⋅ Tohoqua SubDv. ⋅ 34744 Zip Code
Welcome to this beautiful single-family home in the desirable Tohoqua community, built by Pulte in 2022. This modern home offers 3 bedrooms, 2 bathrooms, and a versatile flex room that can be used as a home office, den, playroom, or additional living space. The home features a modern look and thoughtfully designed layout, with an open-concept living area that creates a comfortable flow for everyday living and entertaining. Step outside to enjoy the fenced backyard and screened-in lanai, providing a comfortable outdoor space to relax, enjoy the Florida weather, or entertain guests. Built with modern construction and contemporary design, this home provides the benefits of newer construction in a desirable community. Tohoqua offers a variety of amenities and a convenient location with easy access to shopping, dining, major roads, and the surrounding Central Florida area. Don't miss the opportunity to make this beautiful home your own!

2578 Autumn Peace Drive, Kissimmee
4580 Gadwall Drive, Kissimmee
$355,000
3 Beds ⋅ 2 Baths ⋅ Osprey Ridge SubDv. ⋅ 34744 Zip Code
Welcome to 4580 Gadwall Dr, a beautifully maintained 3-bedroom, 2-bathroom single-story home in the desirable Osprey Ridge community of Kissimmee! Built in 2018, this 1,651-square-foot home is a functional open layout, spacious living areas, a well-appointed kitchen with granite countertops, and a comfortable primary suite featuring a generous bedroom and walk-in closet. The home also offers a 2-car garage, interior laundry room, and a layout designed for easy everyday living. The private primary suite provides a comfortable retreat, while two additional bedrooms provide flexibility for family, guests, a home office, or personal space. All bedrooms are beautifully tiled. A 2-car garage provides convenient parking and additional storage. Beyond the home, enjoy the convenience of a location that puts you close to everything Central Florida provides. Osprey Ridge is located near Boggy Creek Road and Narcoossee Road, providing convenient access to SR 417 and the Florida Turnpike. Lake Nona’s restaurants, shopping, Medical City and major medical facilities are just minutes away, while Orlando International Airport is also conveniently accessible. Nearby recreational opportunities include East Lake Tohopekaliga, local parks, trails and the Austin-Tindall Regional Sports Complex. Move-in ready, well located, and offering the space and functionality today’s buyers are looking for — don’t miss your opportunity to make 4580 Gadwall Dr your new home! This home is priced well below market so it will go fast!

4580 Gadwall Drive, Kissimmee
1560 Gladewater Road, Kissimmee
$405,000
3 Beds ⋅ 2 Baths ⋅ Kindred Ph 2c & 2d SubDv. ⋅ 34744 Zip Code
Welcome to 1560 Gladewater Rd, a beautiful single-story home located in the desirable Kindred community of Kissimmee. Built in 2022, this well-designed residence offers 3 bedrooms, 2 bathrooms, approximately 1,614 square feet of comfortable living space, and a convenient 2-car garage. The open and inviting floor plan creates a seamless connection between the main living, dining, and kitchen areas, making the home ideal for everyday living and entertaining. The spacious primary suite provides a comfortable retreat, while the additional bedrooms offer flexibility for guests, a home office, or additional living needs. Enjoy all that the Kindred community has to offer, including a community pool, fitness center, playgrounds, parks, tennis courts, sidewalks, and recreational areas. Conveniently located near shopping, dining, schools, and major Central Florida roadways, this home provides easy access to Kissimmee, Orlando, Lake Nona, and surrounding attractions. Don't miss the opportunity to make this newer Kissimmee home your own. Schedule your private showing today! Some photos have been stage.

1560 Gladewater Road, Kissimmee
2352 Ross Street, Kissimmee
$315,000
3 Beds ⋅ 2 Baths ⋅ Gilchrist Add To Kissimmee SubDv. ⋅ 34744 Zip Code
ew Construction Home! AFFORDABLE NEW CONSTRUCTION with NO HOA. With 1330sq ft+, ALL ON ONE FLOOR, this model offers an open floor plan that is perfect for daily living or entertaining your loved ones. The Kitchen is FULLY EQUIPPED w/ black sparkling Granite Counters and a COMPLETE stainless steel appliance package are standard. The 1-Car-Garage & Lanai are an added plus. This residence offers the perfect blend of sophistication, comfort, and convenience. Located in the vibrant city of Kissimmee, this home offers easy access to world-class attractions, shopping, dining, and entertainment options. Enjoy proximity to major highways, top-rated schools, and scenic parks, making it the perfect place to call home. Schedule your private tour today and experience Central Florida at its finest.

2352 Ross Street, Kissimmee
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