Osceola, FL Homes

• 

  

  

  /40

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,342 Sq Ft

  305 E Jackson St, Kissimmee, FL 34744

  Looking for a home centrally located near all major shopping, employers, and attractions that Kissimmee has to offer — with NO HOA? Here’s your chance to own a fully renovated, turn-key 3-bedroom, 2-bath home on an oversized lot! From the moment you arrive, you’ll picture yourself relaxing on the charming front porch, surrounded by mature oak trees and soaking in the beautiful Florida weather.

  Jonathan Ortiz LPT REALTY, LLC

  305 E Jackson St, Kissimmee, FL 34744
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• 

  

  

  /19

  $1,575 per month

  • 2 Beds
  • 1.5 Baths
  • 975 Sq Ft
  • Townhouse for Rent

  2017 Kelley Ave, Kissimmee, FL 34744

  Step into this recently updated two-story, two-bedroom, one-and-a-half-bathroom rental unit nestled in the heart of Kissimmee. With 975 square feet of living space, this charming property is ready for its new occupants. Upon entering, you'll be greeted by an inviting open-concept living area and a remodeled fully equipped kitchen. The kitchen features beautiful cabinets, countertops, and

  Alison Ashby CORCORAN PREMIER REALTY

  2017 Kelley Ave, Kissimmee, FL 34744
• 

  

  /2

  $354,000 Sold Jul 31, 2025

  • 1,400 Sq Ft
  • $253/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  2681 Debany Rd, Kissimmee, FL 34744

  Welcome to this beautifully maintained and thoughtfully upgraded home, offering comfort, style, and a prime location. Major systems have been updated for peace of mind, including a new roof in 2018, A/C in 2019, energy-efficient windows installed in 2019 with a transferrable lifetime warranty, and a hot water heater added in 2023. The bathroom features quartzite countertops, MIB cabinetry

  Nick Nastase THE PROPERTY PROS REAL ESTATE, INC

  2681 Debany Rd, Kissimmee, FL 34744
• 

  

  

  /9

  Est $259,716 Not Listed For Sale

  • 2 Beds

  2901 Florida Ave Unit 8, Kissimmee, FL 34744

  2901 Florida Ave Unit 8, Kissimmee, FL 34744
• 

  

  

  /18

  $365,999

  • 4 Beds
  • 2 Baths
  • 1,442 Sq Ft

  Unlisted Address

  A MUST SEE, whether you're commuting to Orlando or exploring the charm of historic downtown Kissimmee, this location puts you a the center of it all. If you are searching for a home with lots of space a peaceful setting and a convenient location, then look no further. This is more than just a home it's a place where your next chapter begins. New roof installed in 2023, remodeled kitchen,

  Jorge Espinosa THE REAL ESTATE GALLERY LLC

  Unlisted Address
• 

  

  /20

  $2,280 per month

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • House for Rent

  2344 Valley Ave, Kissimmee, FL 34744

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2424.90. That covers your base rent, $2280.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  2344 Valley Ave, Kissimmee, FL 34744
• 

  /2

  $310,000 Sold Jul 28, 2025

  • 1,001 Sq Ft
  • $310/SF
  • 98 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  1211 Shawnee Dr, Kissimmee, FL 34744

  Great home for 1st time buyer or investors. Remodeled home with all new flooring in bedrooms. Roof was installed in March of 2018, Airconditioning in 2009, Hot Water heater 2021 and the septic was serviced this month. All appliances including washer and dryer are included. Relax in your tropical oasis with beautiful new wood deck on the front with pressure treated wood. The back screen porch is

  Mary Clevenger WEICHERT REALTORS HALLMARK PRO

  1211 Shawnee Dr, Kissimmee, FL 34744
• 

  

  /20

  Est $423,238 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,395 Sq Ft

  2960 On the Rocks Point, Kissimmee, FL 34747

  2960 On the Rocks Point, Kissimmee, FL 34747
• 

  

  /41

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft

  2666 Capp Cir, Kissimmee, FL 34744

  2666 Capp Circle in Kissimmee, Florida is a charming single-family 3 bedrooms and 2 bathrooms home nestled in the Oak Run neighborhood.New Tile Roof in 2025. New A.C installed in 2018.The property sits on a 0.26-acre lot. Large backyard—great for outdoor activities or future landscaping ideas. Located within easy access to major roads, minutes from the Florida Turnpike, 25 minutes to Walt

  Richie O'Dea BRIGHT TRUST REALTY LLC

  2666 Capp Cir, Kissimmee, FL 34744
• 

  

  /21

  $1,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,425 Sq Ft
  • Townhouse for Rent

  1659 Windsor Oak Ct, Kissimmee, FL 34744

  FOR RENT: Spacious 3 Bedrooms, 2 1⁄2 Bathrooms Townhome centrally located in the gated Windsor Oaks community in Kissimmee. Kitchen is well-equipped with all appliances and a breakfast bar located on the first floor and opens up to the bright family room and screened-in porch. You will be delighted by ALL NEWLY RENOVATED luxurious BATHROOMS installed with modern fixtures. Stairs leading to second

  Mark Peters LA ROSA REALTY LLC

  1659 Windsor Oak Ct, Kissimmee, FL 34744
• 

  /2

  $65,000 Sold Jul 22, 2025

  • Land
  • 0.51 Acre
  • $127,451 per Acre

  • 108 Days On Market

  0 Bay Ave, Kissimmee, FL 34744

  Don’t miss this beautiful half acre lot located off of Michigan Avenue in Kissimmee. Currently zoned for mobile home use, this is a great opportunity! This picturesque lot is mostly cleared and has numerous large oak trees that offer plenty of shade. Schedule your showing today!

  Steven Durrance FLORIDA PINES REALTY, LLC

  0 Bay Ave, Kissimmee, FL 34744
• 

  

  /10

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  402 E Martin St, Kissimmee, FL 34744

  402 E Martin St, Kissimmee, FL 34744
• 

  

  /21

  $379,000

  • 3 Beds
  • 2 Baths
  • 1,281 Sq Ft

  2444 Oak Mill Dr, Kissimmee, FL 34744

  Strategically located and thoughtfully updated, this 3 Bedroom, 2 Bathroom, 2-Car Garage home with NO HOA delivers turnkey value with major system upgrades: Roof, A/C, and Water Heater all replaced in 2023—a forward-thinking investment with long-term peace of mind.The interior boasts an open-concept layout with ceramic tile flooring in the main living areas and stainless steel appliances

  Daniel Fernandez LA ROSA REALTY KISSIMMEE

  2444 Oak Mill Dr, Kissimmee, FL 34744
• 

  

  /20

  $2,215 per month

  • 4 Beds
  • 2 Baths
  • 1,752 Sq Ft
  • House for Rent

  1923 N Brack St, Kissimmee, FL 34744

  ASK ABOUT OUR ALTERNATIVE SECURITY DEPOSIT OPTIONS!Gorgeous home in a beautiful neighborhood! This spacious 4 bedroom, 2 bathroom single-family home in Kissimmee features: Keyless Locks, Smart Thermostat, Primary Suite, Hardwood Floors, Open Concept Layout, Washer/Dryer Hook-Ups, Backyard Patio, Fenced-In Backyard, and Private Driveway. Stainless steel appliances installed upon move-in.

  1923 N Brack St, Kissimmee, FL 34744
• 

  /2

  $298,700 Sold Jul 18, 2025

  • 1,096 Sq Ft
  • $273/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1982

  2527 Christine Dr, Kissimmee, FL 34744

  Welcome to this cozy, well-maintained home with no HOA—enjoy the freedom and flexibility you deserve! Featuring a brand-new A/C (2024) and a roof less than 10 years old, this property offers peace of mind and comfort. Inside, you’ll find tile flooring throughout, enhanced by elegant crown molding and 6-inch baseboards, adding a touch of sophistication to every room. Step outside to a screened-in

  Ronny Desir UNITED SHARES REAL ESTATE LLC

  2527 Christine Dr, Kissimmee, FL 34744
• 

  

  /52

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,890 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /18

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,393 Sq Ft

  2626 Gentre St, Kissimmee, FL 34744

  Discover this charming gem nestled in the heart of Mill Run! This well-maintained 3-bedroom, 2-bath home features a convenient half-circle driveway—perfect for extra parking or even a basketball hoop, all without disturbing your neighbors. Situated on a spacious 0.21-acre lot, there's plenty of room to relax and unwind. Enjoy peaceful evenings in the enclosed lanai as you watch the sunset after

  Daisy Cid REMAX PREMIER PROPERTIES

  2626 Gentre St, Kissimmee, FL 34744
• 

  

  /15

  $1,375 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Townhouse for Rent

  805 Ocean St, Kissimmee, FL 34744

  Welcome to this recently updated 2 bedroom, 1 bath rental unit located in the heart of Kissimmee. With 800 sq ft of living space, this charming property is ready for its newest residents. As you enter the home, you'll immediately notice the open concept living area and remodeled kitchen that give this property a modern touch. The kitchen features updated cabinets, countertops, and new appliances,

  Alison Ashby CORCORAN PREMIER REALTY

  805 Ocean St, Kissimmee, FL 34744
• 

  /2

  $260,000 Sold Jul 18, 2025

  • 1,217 Sq Ft
  • $214/SF
  • 79 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  1304 Mill Creek Place, Kissimmee, FL 34744

  Introducing the charming Kissimmee Home, located in the heart of Kissimmee, FL. This cozy house features 2 bedrooms and 2 bathrooms, perfect for those seeking a comfortable living space. The fenced back yard provides privacy and security, while the screen porch offers a lovely outdoor area to relax and unwind. Centrally located, this home is conveniently situated near shopping, dining, and

  Mary Clevenger WEICHERT REALTORS HALLMARK PRO

  1304 Mill Creek Place, Kissimmee, FL 34744
• 

  

  /13

  Not Listed For Sale

  0 Woodberry Creek Ln Unit O5980804, Kissimmee, FL 34744

  0 Woodberry Creek Ln Unit O5980804, Kissimmee, FL 34744
• 

  

  /51

  $379,900

  • 4 Beds
  • 2 Baths
  • 1,571 Sq Ft

  2637 Debany Rd, Kissimmee, FL 34744

  WELCOME TO THIS BEAUTIFULLY MAINTAINED 4-BEDROOM, 2-BATHROOM HOME LOCATED ON A LARGE CORNER LOT IN THE CONVENIENT LOCATION OF MILL RUN COMMUNITY IN KISSIMMEE. FROM THE MOMENT YOU STEP INSIDE, YOU'LL APPRECIATE THE CERAMIC TILE FLOORING THROUGHOUT, OFFERING A CLEAN, MODERN LOOK AND EASY MAINTENANCE. THE PRIMARY BATHROOM HAS SOME UPDATES, AND THE SPACIOUS KITCHEN PROVIDES PLENTY OF ROOM FOR

  Linda Goodwin-Nichols GOODWIN REALTY & ASSOCIATES, INC

  2637 Debany Rd, Kissimmee, FL 34744
• 

  

  /20

  $2,400 per month

  • 3 Beds
  • 2.5 Baths
  • 1,420 Sq Ft
  • House for Rent

  2614 Quail Run Blvd N, Kissimmee, FL 34744

  Property Id: 2081558Experience comfort and convenience in this charming two-story home, perfectly located in a community with no HOA—just 20 minutes from both Disney World and Orlando International Airport (MCO).This rental features three bedrooms and two and a half bathrooms, offering plenty of space for comfortable living. Please note: the garage has been converted into a

  2614 Quail Run Blvd N, Kissimmee, FL 34744
• 

  /2

  $350,000 Sold Jul 08, 2025

  • 1,172 Sq Ft
  • $299/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  2454 Quail Run Blvd N, Kissimmee, FL 34744

  This beautifully renovated and move-in ready gem offers almost 1,200 sq ft of thoughtfully designed living space under heat and air WITH a Florida room! From the moment you arrive, you’ll appreciate the fully fenced-in yard which is perfect for pets, play, or private outdoor gatherings. Step inside and fall in love with the gourmet-inspired kitchen, featuring rich wood cabinetry, gleaming

  Tiffany Licata IRON VALLEY REAL ESTATE OSCEOL

  2454 Quail Run Blvd N, Kissimmee, FL 34744
• 

  

  /37

  Est $339,346 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,644 Sq Ft

  2295 Softwind Ct, Kissimmee, FL 34744

  2295 Softwind Ct, Kissimmee, FL 34744
• 

  

  /32

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft

  1375 Springfield St, Kissimmee, FL 34744

  This beautifully updated 3-bedroom, 2-bath home in Jacaranda Estates features a private screened-in pool, pergola, wood-burning fireplace, and ceramic tile throughout. Recent upgrades include a new roof (3 years old), A/C (2020), and water heater. The kitchen comes with nearly-new appliances under warranty, and a backyard with Yoga deck, shed adds storage space. Enjoy the freedom of no HOA or

  Lanamara Xavier FIDELITY REALTY GROUP LLC

  1375 Springfield St, Kissimmee, FL 34744
• 

  

  /9

  $2,300 per month

  • 3 Beds
  • 1 Bath
  • 1,574 Sq Ft
  • House for Rent

  613 Carol Terrace Unit Main, Kissimmee, FL 34744

  Spacious and well-maintained 3-bedroom, 1-bath home located in a desirable area of Kissimmee, offering a convenient location close to schools, shopping, and major highways—an excellent opportunity for families seeking comfort and value in a thriving community. Water, Electricity and Internet are Included with the Rent.

  Perry Taveras FLEURYS INVESTMENTS LLC

  613 Carol Terrace Unit Main, Kissimmee, FL 34744
• 

  /2

  $385,000 Sold Jul 08, 2025

  • 1,585 Sq Ft
  • $243/SF
  • 184 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2000

  2460 Oak Mill Dr, Kissimmee, FL 34744

  Located in the Kissimmee subdivision of Oakbrook Estates, where you’ll enjoy HOA-free living, this 3 bedroom, 2 bathroom split plan, pool home offers loads of added space for you to live comfortably. Stepping through the front door you find yourself in a large open concept dining room and living room combo featuring vaulted ceilings, with a massive kitchen to your right. The kitchen with its

  Bethanne Baer BEAR TEAM REAL ESTATE

  2460 Oak Mill Dr, Kissimmee, FL 34744
• 

  

  /20

  Est $336,429 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,393 Sq Ft

  1522 Wyman Cir, Kissimmee, FL 34744

  1522 Wyman Cir, Kissimmee, FL 34744
• 

  

  /14

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft

  2779 Theresa Dr, Kissimmee, FL 34744

  No HOA and two-year old roof! Run if you want a centrally located home with a large vinyl fenced yard and Florida Room located within a cul-de-sac. These are just a few characteristic highlights of this Kissimmee home which is also a short ten minutes away the Amtrak Train Station providing access to other major Florida cities. This home is not only affordable, but also checks all the boxes with

  Kelvis Melo THE EXPERTS TEAM REALTY INC

  2779 Theresa Dr, Kissimmee, FL 34744
• 

  

  /16

  $2,110 per month

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft
  • House for Rent

  1340 Sierra Cir, Kissimmee, FL 34744

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  1340 Sierra Cir, Kissimmee, FL 34744
• 

  /2

  $306,000 Sold Jul 08, 2025

  • 1,195 Sq Ft
  • $256/SF
  • 366 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  2912 Willow Oak Ct, Kissimmee, FL 34744

  Perfect starter home in a quiet Cul-De-Sac. This 3 bedroom, 2 bathroom, open concept living and dining area home Centrally located near Osceola Parkway, Florida Turnpike, I-4, and 417. Also, close to all the theme parks and you have all kinds of convenient shopping nearby. All the majors are solid. Roof was replaced in 2017. A/C unit installed in 2018. Water heater replaced in 2021. Solar Panels

  Sawrys Paulino CHARLES RUTENBERG REALTY ORLANDO

  2912 Willow Oak Ct, Kissimmee, FL 34744
• 

  

  /16

  Est $364,865 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft

  2650 Capp Cir, Kissimmee, FL 34744

  2650 Capp Cir, Kissimmee, FL 34744
• 

  

  /6

  $357,000

  • 3 Beds
  • 2 Baths
  • 1,185 Sq Ft

  1542 Colony Ave, Kissimmee, FL 34744

  Welcome to your dream home! A charming property with no HOA. This home features 3 bedroom and 2 full bathrooms. Open floor plan. As you enter the home it opens up to a warming atmosphere, leading to the living room and dining room area. The kitchen window looks out to your pool where you can entertain family and friends, perfect for enjoying the outdoors. This home also has a large private fenced

  Veronica Bagunas CHARLES RUTENBERG REALTY ORLANDO

  1542 Colony Ave, Kissimmee, FL 34744
• 

  

  /16

  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft
  • House for Rent

  1547 Elmwood Ave, Kissimmee, FL 34744

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  1547 Elmwood Ave, Kissimmee, FL 34744
• 

  /2

  $375,000 Sold Jul 02, 2025

  • 1,603 Sq Ft
  • $234/SF
  • 10 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1987

  1449 Amanda Rd, Kissimmee, FL 34744

  Beautiful and Spacious Home on large Corner Lot in Mill Run subdivision. Excellent location near Osceola Parkway, Osceola Loop Mall, major stores, restaurants, Turnpike exit, etcNO Home Owners Association, no CDD, 4 spacious bedrooms, 2 Baths, with family room, dining room,and living room, all interior with convenient ceramic tiles throughout, High CeilingsNew Roof 2023, new garage door

  Gilda Santacana CHARLES RUTENBERG REALTY ORLANDO

  1449 Amanda Rd, Kissimmee, FL 34744
• 

  

  /34

  Est $336,169 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,896 Sq Ft

  1912 Seminole Ave, Kissimmee, FL 34744

  1912 Seminole Ave, Kissimmee, FL 34744
• 

  

  /28

  $420,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,610 Sq Ft

  1458 Heather Way, Kissimmee, FL 34744

  Under contract-accepting backup offers. ***MOTIVATED SELLER!***Modern Renovation + Co-Living Potential Near Valencia College listed UNDER appraised value!This stylishly renovated 4-bedroom, 3-bath home sits on a large corner lot in the heart of Kissimmee—just minutes from Valencia College, making it an ideal opportunity for homeowners or savvy investors. With new roof and piping (2024), and a

  Zasquia Villegas MY REALTY GROUP, LLC.

  1458 Heather Way, Kissimmee, FL 34744
• 

  

  /15

  $2,670 per month

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • House for Rent

  2429 Franklin Dr, Kissimmee, FL 34744

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

  2429 Franklin Dr, Kissimmee, FL 34744
• 

  /2

  $320,000 Sold Jun 27, 2025

  • 971 Sq Ft
  • $330/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1954

  2704 Sample St, Kissimmee, FL 34744

  Don’t miss this fantastic investment opportunity located on the corner of Carroll Street and Sample Street in a thriving area of Kissimmee. The property is currently zoned Residential (RS-3) but with a Future Land Use of Medium Density/Intensity, there are multiple options available to re-zone the property for commercial usage, including Commercial Office (CO) or Residential Professional Business

  Steven Durrance FLORIDA PINES REALTY, LLC

  2704 Sample St, Kissimmee, FL 34744
• 

  

  /33

  Est $365,051 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft

  1533 Amherst Ln, Kissimmee, FL 34744

  1533 Amherst Ln, Kissimmee, FL 34744

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