Osceola, FL Homes

• 

  

  

  /27

  $485,500

  • 4 Beds
  • 3 Baths
  • 1,914 Sq Ft

  432 Ocean Course Ave, Kissimmee, FL 34747

  Investor’s Dream in Davenport’s Premier Resort Community – Turnkey Luxury & Location!Welcome to a rare opportunity to own a fully furnished 4-bedroom, 3-bathroom townhome in one of Davenport’s most coveted resort destinations. Thoughtfully designed for both personal enjoyment and income generation, this elegant residence offers a seamless combination of space, style, and

  

  Yadira Bello

  COLDWELL BANKER REALTY

  (321) 215-7621

  432 Ocean Course Ave, Kissimmee, FL 34747
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  Explore Mill Slough

• 

  

  

  /98

  $1,785 - $2,658 per month

  Aston Square Apartments

  1 - 3 Beds

  1387 E Vine St, Kissimmee, FL 34744

  Experience modern living like never before at Aston Square. Our luxury apartments located in the highly desirable Kissimmee area offer keyless entry, custom designer closets, and chef-inspired kitchens that together, creates a luxury home that is yours to personalize.

  1387 E Vine St, 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
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  /49

  Est $439,354 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,873 Sq Ft

  908 Lacey Oaks Ct, Kissimmee, FL 34744

  908 Lacey Oaks Ct, Kissimmee, FL 34744
• 

  

  

  /25

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  1621 Emily Ct, Kissimmee, FL 34744

  Welcome Home! Move-In Ready 3-Bedroom Villa with Investment Potential – Motivated SellerStep into comfort, style, and smart opportunity with this charming one-story town villa boasting 3 spacious bedrooms and 2 full bathrooms in an unbeatable location. Whether you're a first-time buyer, growing family, or savvy investor, this property is a standout choice in today's market. High ceilings and

  

  Yadira Bello

  COLDWELL BANKER REALTY

  (321) 353-6737

  1621 Emily Ct, Kissimmee, FL 34744
• 

  

  /16

  $2,070 per month

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • House for Rent

  2409 Oak Hollow Dr, 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

  2409 Oak Hollow Dr, 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
• 

  

  /27

  Est $419,430 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,196 Sq Ft

  707 E Jackson St, Kissimmee, FL 34744

  707 E Jackson St, Kissimmee, FL 34744
• 

  

  /21

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,523 Sq Ft

  2518 Bowmer Dr, Kissimmee, FL 34744

  Move-in ready, completely remodeled. Single family home featuring 3 bedrms., 2 baths, 2 car garage. The welcoming great room offers plenty of space to entertain family and friends. The fully equipped kitchen has plenty of cabinets, storage space, and granite countertops (2023). Relax in the privacy and comfort of the spacious Florida room. Bathrooms, granite countertops, roof, and fence were

  

  Michael Solomon

  COLDWELL BANKER SOLOMON

  (321) 449-8065

  2518 Bowmer Dr, Kissimmee, FL 34744
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  /56

  $1,371 - $4,401 per month

  19 South Apartments

  Studio - 3 Beds

  3050 Station Square, Kissimmee, FL 34744

  Sunny Summer Savings! Half Off Rent for 2 Months! Plus, Look and Lease for Waived Fees! Now leasing spacious one-, two-, and three-bedroom apartments for rent in Kissimmee, FL. 19 South, upscale apartment living is a beautifully planned and award-winning luxury community ideally located in Kissimmee, FL! 19 South is perfectly located right off the Florida Turnpike on Osceola Parkway perfectly

  3050 Station Square, 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
• 

  

  /7

  Not Listed For Sale

  0 Barn St Unit 2009177, Kissimmee, FL 34744

  0 Barn St Unit 2009177, Kissimmee, FL 34744
• 

  

  /24

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  1603 Emily Ct, Kissimmee, FL 34744

  Charming 3-bedroom, 2-bath home located in Kissimmee, near Hunters Creek and Buenaventura Lakes, across the street from Valencia Community College This well-kept property features a bright living and dining area, and a functional kitchen with plenty of storage. The primary bedroom includes a private bath and walk-in closet. Located in a quiet community with easy access to major roads like 417 and

  

  Yadira Bello

  COLDWELL BANKER REALTY

  (321) 382-1298

  1603 Emily Ct, Kissimmee, FL 34744
• 

  

  /19

  $1,600 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

  $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
• 

  

  /7

  Not Listed For Sale

  0 Barn St Unit 107245, Kissimmee, FL 34744

  0 Barn St Unit 107245, Kissimmee, FL 34744
• 

  

  /31

  $274,500

  • 3 Beds
  • 3 Baths
  • 1,406 Sq Ft

  1642 Windsor Oak Ct, Kissimmee, FL 34744

  One-of-a-Kind 3 Bed, 3 Bath Townhome in Kissimmee! This is the best value for square footage in all of Windsor Oaks! This rare gem stands out with three full bathrooms, including a custom-tiled shower with bench, perfect for guests or multi-gen living! Enjoy soaring vaulted ceilings, spacious rooms, and wood laminate flooring throughout. Skylights flood the home with natural light, and no direct

  Tara Cadman IRON VALLEY REAL ESTATE CENTRAL FLORIDA

  1642 Windsor Oak Ct, Kissimmee, FL 34744
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  /16

  $1,980 per month

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft
  • House for Rent

  1357 Boulder Dr, 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 $2124.90. That covers your base rent, $1980.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1357 Boulder Dr, 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
• 

  

  /7

  Not Listed For Sale

  0 Barn St Unit MFRO6139040, Kissimmee, FL 34744

  0 Barn St Unit MFRO6139040, Kissimmee, FL 34744
• 

  

  /53

  $425,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft

  2336 Meadow Ct, Kissimmee, FL 34744

  Under contract-accepting backup offers. Take advantage of this great property in an amazing location! This stunning home has everything one would want! Plenty of space with four bedrooms and two bathrooms, amazing upgrades such as solar panels and a pool, and located near several shopping centers and Valencia College, a fantastic community college! However, that is not all. This charming home

  Blanca Armada REMAX PREMIER PROPERTIES

  2336 Meadow Ct, Kissimmee, FL 34744
• 

  

  /9

  $1,275 per month

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

  2005 Kelley Ave, Kissimmee, FL 34744

  Cozy 2 bedrooms 1 bath condo home located in Kissimmee FL! You will be surprised by the space that this villa home has. All appliances included! Washer and dryer hookups inside the unit! Conveniently located close to downtown Kissimmee, with quick access to 192, the FL Turnpike and Osceola Parkway.Pets Not Allowed$1,275.00 Monthly Rent$1,912.50 Security Deposit$95.00

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  2005 Kelley Ave, 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
• 

  

  /26

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,012 Sq Ft

  2744 Burrows Ave, Kissimmee, FL 34744

  2744 Burrows Ave, Kissimmee, FL 34744
• 

  

  /28

  $379,900

  • 3 Beds
  • 2 Baths
  • 1,679 Sq Ft

  1562 Jason St, Kissimmee, FL 34744

  This well-maintained single-family home offers 3 spacious bedrooms, 2 full bathrooms, and a private screened-in pool, perfect for enjoying Florida living year-round. Located on a corner lot, the home features excellent curb appeal and added privacy. Step inside to a bright and open layout, with tile and laminate flooring, an upgraded kitchen, and comfortable living spaces. The home is equipped

  Maria Pagan DEAL MAKERS REALTY TEAM CORP

  1562 Jason St, Kissimmee, FL 34744
• 

  

  /17

  $2,199 per month

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • House for Rent

  1481 Harbin Dr, Kissimmee, FL 34744

  Welcome to 1481 Harbin Dr, a move-in-ready 3-bedroom, 2-bathroom smart home offering 1,113 sq ft of thoughtfully designed living space. Inside, you’ll find a bright and open floor plan with tile flooring throughout, a spacious living room with vaulted ceilings, and a fully equipped kitchen featuring stainless steel appliances, a dishwasher, refrigerator, microwave, and a serving window perfect

  1481 Harbin Dr, 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
• 

  

  /7

  Not Listed For Sale

  0 Boyd St, Kissimmee, FL 34744

  0 Boyd St, Kissimmee, FL 34744
• 

  

  /68

  $439,000

  • 4 Beds
  • 2 Baths
  • 1,679 Sq Ft

  1545 Trumbull St, Kissimmee, FL 34744

  Welcome to 1545 Trumbull Street. This beautiful home with Great Curb Appeal is in one of the most desirable and Peaceful Neighborhoods in Kissimmee, Florida. This beautifully well-maintained single-story home blends comfort, style, and functionality. This 4-bedroom, 2-bathroom residence features a warm and inviting exterior with brick and wood siding accents, a covered entryway, and a spacious

  Nil Mendez CHARLES RUTENBERG REALTY ORLANDO

  1545 Trumbull St, Kissimmee, FL 34744
• 

  

  /21

  $1,900 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

  $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
• 

  

  /3

  Not Listed For Sale

  0 W Carroll St Unit O6095181, Kissimmee, FL 34744

  0 W Carroll St Unit O6095181, Kissimmee, FL 34744
• 

  

  /31

  $365,000 Open Sat 12AM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,189 Sq Ft

  2335 Butternut Ct, Kissimmee, FL 34744

  Charming Pool Home in Heather Oaks – Kissimmee – NO HOA! Located on a quiet cul-de-sac in the highly desirable Heather Oaks community, in the heart of Kissimmee, this beautiful property offers a prime location just minutes from Mill Creek Elementary, Denn John Middle School, Valencia College, shopping, dining, entertainment, and major local attractions. From the moment you arrive, you’ll

  Paola Ramirez ROBERT SLACK LLC

  2335 Butternut Ct, Kissimmee, FL 34744
• 

  

  /15

  $1,830 per month

  • 4 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • House for Rent

  2225 N Seminole St, Kissimmee, FL 34744

  Please note that the advertised price may exclude additional fees. These include a mandatory $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; fees for amenities like smart home or internet service; and optional conditional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99), pet fees/rent, or pool

  2225 N Seminole St, 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
• 

  

  /26

  Est $299,308 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  2119 N Seminole St, Kissimmee, FL 34744

  2119 N Seminole St, Kissimmee, FL 34744
• 

  

  /40

  $359,900

  • 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
• 

  

  /15

  $1,400 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

  $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
• 

  

  /3

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  2808 Jessup Ave, Kissimmee, FL 34744

  2808 Jessup Ave, Kissimmee, FL 34744

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