133,962

Osceola, FL Homes

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  • /26

    $263,000 Pending

    • 2 Beds
    • 2.5 Baths
    • 1,161 Sq Ft

    3069 White Orchid Rd, Kissimmee, FL 34747

    Under contract-accepting backup offers. Tucked away on the most secluded road within the beautiful gated resort community of Encantada, this 2-bedroom, 2.5-bath townhome offers a peaceful retreat with a private lanai and jacuzzi. Stylishly updated over the past several years with attention to detail, this property stands out the moment you step inside. It’s that unmistakable feeling—when a home

    Agent Photo

    Dave Zembala

    ZEMBALA GROUP

    (321) 850-4692

    3069 White Orchid Rd, Kissimmee, FL 34747
  • /20

    $2,550 per month

    • 4 Beds
    • 2.5 Baths
    • 1,868 Sq Ft
    • Condo for Rent

    1179 Woody Cypress Dr Unit 1, Kissimmee, FL 34746

    Move-In Ready... Pretty much NEW!!! Outstanding Community amenities include a resort-style pool, splash pad, fenced playground, multi-sports field, picnic area, BBQ grills, and scenic walking trails. Just about 18-20 minutes to Disney!

    Agent Photo

    Mesner Belidor

    KELLER WILLIAMS LEGACY REALTY

    (321) 252-6505

    1179 Woody Cypress Dr Unit 1, Kissimmee, FL 34746
  • /15

    $408,878 Sold Aug 29, 2025

    • 1,755 Sq Ft
    • $233/SF
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    1909 Fulfillment Dr, Kissimmee, FL 34744

    This spacious two-story townhome features a formal dining room and living room at the front of the home, followed by the modern kitchen and family room. Ideal for outdoor living and entertaining is an open walkway which extends into the lanai. On the second floor are all three bedrooms, including the tranquil owner’s suite with an adjoining bathroom and walk-in closet.

    Lennar

    1909 Fulfillment Dr, Kissimmee, FL 34744
    • /2

      Not Listed For Sale

      • 9 Beds
      • 5 Baths
      • 4,289 Sq Ft

      2959 Fable St, Kissimmee, FL 34746

      2959 Fable St, Kissimmee, FL 34746
  • /55

    $339,500 Pending

    • 3 Beds
    • 2 Baths
    • 1,640 Sq Ft

    1042 Waterside Dr, Kissimmee, FL 34747

    Under contract-accepting backup offers. $10,000 Closing Cost Credit! Priced to Sell! Welcome to Siena at Celebration, your chance to own the best-priced three-bedroom townhome in all of Celebration, now with an incredible $10,000 credit towards your closing costs.This three-story residence boasts sweeping golf course and water views, an attached two-car garage, and endless potential for

    Agent Photo

    Lisa Grinceri

    KELLER WILLIAMS REALTY AT THE LAKES

    (321) 472-5152

    1042 Waterside Dr, Kissimmee, FL 34747
  • /15

    $3,200 per month

    • 3 Beds
    • 2.5 Baths
    • 1,704 Sq Ft
    • Townhouse for Rent

    788 Driving Range Ct, Kissimmee, FL 34747

    SEASONAL, LONG TERM AND SHORT TERM RENTALS! Sought after Golf community in Reunion Resort. Tastefully decorated, just bring your toothbrush and personal belongings. Access to 10 pool in the resort, dog parks, golf carts allowed. Three guarded gates for security. conveniently located near the 429 and I-4. Ready for your client to occupy. Please use this link to apply. (copy and paste

    Agent Photo

    Consuelo Vilar

    WELCOME HOME REALTY GROUP LLC

    (321) 621-8970

    788 Driving Range Ct, Kissimmee, FL 34747
  • /16

    $267,990 Sold Aug 29, 2025

    • 1,562 Sq Ft
    • $172/SF
    • 2 Beds
    • Built 2025

    4293 Curacao Place, Kissimmee, FL 34758

    This new duplex-style home offers convenient single-floor living for simple entertaining and multitasking. An inviting open-concept floorplan maximizes space and features direct access to the lanai for outdoor entertainment and leisure. A secluded study, ready to be used a movie room or guest suite, shares a hallway with a bedroom and full bathroom, and the lavish owner’s suite is tucked into a

    Lennar

    4293 Curacao Place, Kissimmee, FL 34758
    • /2

      Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,180 Sq Ft

      3217 Slyline Loop, Kissimmee, FL 34758

      3217 Slyline Loop, Kissimmee, FL 34758
  • /48

    $445,000 Pending

    • 6 Beds
    • 2.5 Baths
    • 2,646 Sq Ft

    8812 Kensington Ct, Kissimmee, FL 34747

    One or more photo(s) has been virtually staged. Experience Florida living in this spacious 6-bedroom, 2.5-bathroom home located at 8812 Kensington Ct, Kissimmee, just minutes from Disney, shopping, and dining. Nestled in the established community of Lindfields with no HOA, this 2,646 sq.ft. home features an open-concept main level with tile flooring that seamlessly connects the kitchen, dining,

    Agent Photo

    Carlos German

    EXP REALTY LLC

    (321) 386-2227

    8812 Kensington Ct, Kissimmee, FL 34747
  • /23

    $2,400 per month

    • 3 Beds
    • 2.5 Baths
    • 1,556 Sq Ft
    • Townhouse for Rent

    1163 Boardwalk Place, Kissimmee, FL 34747

    YOU ARE THE FIRST TENANT! BRAND NEW CONSTRUCTION, GREAT LOCATION in Kissimmee!!! The Florence floor plan offers plenty of space to both relax and socialize! Having a SPACIOUS great room, dining room and kitchen COMBINED with a breakfast bar creates a FANTASTIC ENVIRONMENT for cooking, enjoying meals and spending quality time together. KITCHEN with BRAND NEW APPLIANCES, a spacious pantry and

    Agent Photo

    Francine Arroyo Santowski

    BHHS FLORIDA REALTY

    (321) 450-7594

    1163 Boardwalk Place, Kissimmee, FL 34747
  • /16

    $279,990 Sold Aug 29, 2025

    • 1,562 Sq Ft
    • $179/SF
    • 2 Beds
    • Built 2025

    4325 Curacao Place, Kissimmee, FL 34758

    This new duplex-style home offers convenient single-floor living for simple entertaining and multitasking. An inviting open-concept floorplan maximizes space and features direct access to the lanai for outdoor entertainment and leisure. A secluded study, ready to be used a movie room or guest suite, shares a hallway with a bedroom and full bathroom, and the lavish owner’s suite is tucked into a

    Lennar

    4325 Curacao Place, Kissimmee, FL 34758
    • /2

      Not Listed For Sale

      7982 Magnolia Bend Ct, Kissimmee, FL 34747

      7982 Magnolia Bend Ct, Kissimmee, FL 34747
  • /29

    $292,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,081 Sq Ft

    2778 Almaton Loop Unit 402, Kissimmee, FL 34747

    Under contract-accepting backup offers. Discover this updated 2-bedroom, 2-bathroom condo located on the 4th floor in Windsor Hills. This unit features luxury vinyl flooring throughout and offers great views with no units above, ensuring a quieter living experience.The property is situated in the desirable Windsor Hills community, known for its excellent rental potential. This condo has a

    Agent Photo

    Deanna Meredith

    LUXE PROPERTIES LLC

    (321) 273-8224

    2778 Almaton Loop Unit 402, Kissimmee, FL 34747
  • /8

    $800 per month

    • 1.5 Baths
    • 13,520 Sq Ft
    • Apartment for Rent

    2295 E Irlo Bronson Memorial Hwy Unit 100, Kissimmee, FL 34744

    Robert Beyer

    Robert Beyer

    (321) 204-6205

    2295 E Irlo Bronson Memorial Hwy Unit 100, Kissimmee, FL 34744
  • /22

    $439,990 Sold Aug 29, 2025

    • 1,828 Sq Ft
    • $241/SF
    • 4 Beds
    • 2 Baths
    • Built 2025

    1898 Walnut Creek Dr, Kissimmee, FL 34744

    The property is located at 1898 Walnut Creek Drive KISSIMMEE FL 34744 priced at 439990, the square foot and stories are 1828, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

    D.R. Horton

    1898 Walnut Creek Dr, Kissimmee, FL 34744
    • /2

      Est $441,117 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,805 Sq Ft

      3131 Armstrong Spring Dr, Kissimmee, FL 34744

      3131 Armstrong Spring Dr, Kissimmee, FL 34744
  • /37

    $299,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 1,969 Sq Ft

    1303 Congo Ct, Kissimmee, FL 34759

    One or more photo(s) has been virtually staged. Step into modern living at 1303 Congo Court, Kissimmee, where this 2022-built home offers the benefits of a like-new residence with thoughtful design and functionality throughout. Featuring four bedrooms and two and a half baths across 1,969 square feet, the layout is designed for comfort and ease, with all bedrooms conveniently located upstairs and

    Agent Photo

    Carlos German

    EXP REALTY LLC

    (321) 382-5619

    1303 Congo Ct, Kissimmee, FL 34759
  • /7

    $850 per month

    • 1 Bath
    • 300 Sq Ft
    • Apartment for Rent

    5399 W Irlo Bronson Memorial Hwy Unit 101, Kissimmee, FL 34746

    Robert Beyer

    Robert Beyer

    (702) 283-1987

    5399 W Irlo Bronson Memorial Hwy Unit 101, Kissimmee, FL 34746
  • 1769 Bryant St, Kissimmee, FL 34746

    $337,990 Sold Aug 29, 2025

    • 1,614 Sq Ft
    • $209/SF
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    1769 Bryant St, Kissimmee, FL 34746

    The property is located at 1769 Bryant Street KISSIMMEE FL 34746 priced at 337990, the square foot and stories are 1614, 2.The number of bath is 2, halfbath is 1 there are 3 bedrooms and 2 garages. For more details please, call or email.

    D.R. Horton

    1769 Bryant St, Kissimmee, FL 34746
    • /18

      Est $432,186 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,431 Sq Ft

      3817 Golden Knot Dr, Kissimmee, FL 34746

      3817 Golden Knot Dr, Kissimmee, FL 34746
  • /49

    $269,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,875 Sq Ft

    1457 Teal Dr, Kissimmee, FL 34759

    Under contract-accepting backup offers. Welcome to this charming and meticulously maintained 3 bedroom, 2 bath home located in the highly sought-after Poinciana Villages community, abundant with amenities. Step inside to the combination formal living and dining room, illuminated by the natural light. The spacious kitchen is equipped with a skylight above, and ample space for meal prep & storage

    Agent Photo

    Jay Patterson

    KELLER WILLIAMS ADVANTAGE REALTY

    (321) 463-7710

    1457 Teal Dr, Kissimmee, FL 34759
  • /21

    $1,800 per month

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft
    • Condo for Rent

    2212 Grand Cayman Ct Unit 1617, Kissimmee, FL 34741

    This beautifully maintained 2-bedroom, 2-bathroom condo offers a spacious first-floor layout with all-tile flooring for easy maintenance and a modern touch. The highlight? A SEPARATE OFFICE SPACE!, perfect for working from home, studying, or creating your own private retreat! Located in a gated, resort-style community, you’ll enjoy amenities designed for comfort and leisure, all while being close

    Agent Photo

    Kriselys Tapia

    SERHANT

    (321) 321-1973

    2212 Grand Cayman Ct Unit 1617, Kissimmee, FL 34741
  • /11

    $399,990 Sold Aug 29, 2025

    • 1,589 Sq Ft
    • $252/SF
    • 3 Beds
    • 2 Baths
    • Built 2025

    4576 Noble St, Kissimmee, FL 34746

    Step into the foyer, where two bedrooms with a shared bath are located at the front of the home. As you continue down the hallway, you’ll pass the laundry room and access to the two-car garage before entering the open-concept kitchen, family room, and dining area. A covered patio sits just off the dining space, and tucked away on the opposite side of the family room is the primary bedroom,

    Starlight Homes

    4576 Noble St, Kissimmee, FL 34746
    • /19

      Est $311,098 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,035 Sq Ft

      3375 Bellezza Ct, Kissimmee, FL 34746

      3375 Bellezza Ct, Kissimmee, FL 34746
  • /30

    $354,000

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    165 Citrine Loop, Kissimmee, FL 34758

    Short Sale. Welcome to this stunning property with 4 bedroom, 2-bathroom home features an open concept layout perfect for modern living. The spacious kitchen is a chef’s dream with stainless steel appliances, granite counte4rtops, a large island, and spacious pantry. The owner’s suite offers a peaceful retreat with a walk-in closet and shower. Enjoy the energy efficiency in mind, this home

    Agent Photo

    Maria Baez

    EMPIRE NETWORK REALTY

    (321) 449-2843

    165 Citrine Loop, Kissimmee, FL 34758
  • /18

    $2,150 per month

    • 3 Beds
    • 2.5 Baths
    • 1,557 Sq Ft
    • Townhouse for Rent

    9377 Westside Hills Dr, Kissimmee, FL 34747

    Ready for your family to move into this beautiful townhome in the Champions Gate area. Fully equipped with state-of-the-art stainless steel appliances, all with a warranty. The kitchen features 36" cabinets, granite countertops, and an open concept, making it spacious and perfect for family entertaining. This townhome features 3 bedrooms, 2 full bathrooms, and 1 half bathroom, plus a one-car

    Agent Photo

    Sonia Chacon

    AGENT TRUST REALTY CORPORATION

    (321) 442-7643

    9377 Westside Hills Dr, Kissimmee, FL 34747
  • /2

    $475,000 Sold Aug 29, 2025

    • 2,808 Sq Ft
    • $169/SF
    • 0 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2000

    1942 Willow Wood Dr, Kissimmee, FL 34746

    " PRICE IMPROVEMENT " EMBRACE THE SUNSHINE LIFESTYLE IN YOUR EXQUISITE FLORIDA HOME" NEW ROOF 2019 NEW HVAC 2017 Located in The Oaks, a pristine golf course community in Southwest Kissimmee, situated near conservation areas, major destination attractions, and the historic downtown center. Live the premiere golf and country club lifestyle without the high dues and mandatory investments! This

    Janet Yee EXP REALTY LLC

    1942 Willow Wood Dr, Kissimmee, FL 34746
    • /15

      Est $322,185 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,043 Sq Ft

      3351 Bellezza Ct, Kissimmee, FL 34746

      3351 Bellezza Ct, Kissimmee, FL 34746
  • /47

    $625,000

    • 4 Beds
    • 3 Baths
    • 2,768 Sq Ft

    3427 Harborside Ct, Kissimmee, FL 34746

    Welcome to 3427 Harborside Ct - a beautifully updated residence nestled on an oversized conservation lot with no rear neighbors and tranquil partial views of Lake Tohopekaliga. Located in the prestigious, guard-gated Bellalago community, this home offers the perfect blend of privacy, luxury, and natural beauty. This spacious home features 4 bedrooms, 3 full bathrooms, a dedicated office, and a

    Agent Photo

    Mabel Vega Negron

    La Rosa Realty Llc

    (321) 499-2098

    3427 Harborside Ct, Kissimmee, FL 34746
  • /51

    $4,150 per month

    • 8 Beds
    • 6 Baths
    • 4,041 Sq Ft
    • House for Rent

    1650 Lima Ave, Kissimmee, FL 34747

    Fully furnished and move-in ready, this expansive 9BR/6BA pool home delivers long-term luxury living just minutes from Disney. The open great room flows to a state-of-the-art kitchen (breakfast bar) and an elegant 12-seat dining area. Main level includes two en-suite bedrooms; upstairs offers a spacious loft/second living room plus seven additional bedrooms (several tastefully themed) and

    Agent Photo

    Cui Li

    RATIO REAL ESTATE, LLC

    (321) 517-2267

    1650 Lima Ave, Kissimmee, FL 34747
  • /2

    $390,000 Sold Aug 29, 2025

    • 1,596 Sq Ft
    • $244/SF
    • 3 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2004

    8541 Sunrise Key Dr, Kissimmee, FL 34747

    Fantastic fully furnished single family home located in a popular community of Emerald Island Resort. Both primary bedrooms had the floors changed to Laminate in 2023. The roof was also replaced in 2023. This exclusive resort called EMERALD ISLAND is located in Kissimmee Florida just 5 minutes from Disney World. The community has a dramatic palm tree lined boulevard, passing lakes with fountains

    Bernard Scarpa AMERICAN IDEAL HOMES, LLC

    8541 Sunrise Key Dr, Kissimmee, FL 34747
    • /67

      Est $375,003 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,705 Sq Ft

      549 San Joaquin Rd, Kissimmee, FL 34759

      549 San Joaquin Rd, Kissimmee, FL 34759
  • /51

    $384,990

    • 3 Beds
    • 2 Baths
    • 1,186 Sq Ft

    3111 Paradox Cir Unit 406, Kissimmee, FL 34746

    Welcome to this beautiful 3 bedroom / 2 bathroom fully furnished LUXURY condo in Storey Lake NEAR DISNEY! Located on the fourth floor with easy elevator access! Perfect for SHORT TERM RENTAL INCOME or to have as a vacation home, you'll fall in love with what this unit offers! Some of the features include a spacious great room, generously sized bedrooms, an oversized kitchen island, tons of

    Agent Photo

    Andrew Kincaid

    BHHS FLORIDA REALTY

    (321) 461-2870

    3111 Paradox Cir Unit 406, Kissimmee, FL 34746
  • /20

    $2,500 per month

    • 4 Beds
    • 2 Baths
    • 2,198 Sq Ft
    • House for Rent

    923 Tramells Trail, Kissimmee, FL 34744

    Welcome to 923 Tramells Trail, a charming and spacious **single-family home for rent in Kissimmee**. This beautifully maintained residence offers **4 bedrooms and 2 bathrooms** with an open and inviting floor plan designed for comfort and convenience. The bright living area flows seamlessly into the dining space and kitchen, which is equipped with modern appliances and plenty of cabinetry. The

    Agent Photo

    Lorena Cabal Ospina

    AGENT TRUST REALTY CORPORATION

    (321) 449-2161

    923 Tramells Trail, Kissimmee, FL 34744
  • /2

    $725,000 Sold Aug 29, 2025

    • 2,451 Sq Ft
    • $296/SF
    • 4 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1995

    3051 Granada Blvd, Kissimmee, FL 34746

    This beautiful and majestic property sits on approximately 2.4 acres in the highly desirable Estates of Toho community. NO HOA. IT HAS THREE (3) SPACIOUS BEDROOMS AND THREE LARGE AND RENOVATED BATHROOMS. This property is surrounded by beautiful oak and palm trees. AND WITH ENOUGH LAND TO ENJOY THE COUNTRY IN THE CITY AND PLANTING MANY TREES AND FRUITS THAT YOU HAVE WANTED OR PLANNED.This real

    Byron Barguil LA ROSA REALTY INTERNACIONAL LLC

    3051 Granada Blvd, Kissimmee, FL 34746
    • /29

      Est $310,588 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,530 Sq Ft

      9041 Carlotta Way, Kissimmee, FL 34747

      9041 Carlotta Way, Kissimmee, FL 34747
  • /71

    $699,000

    • 6 Beds
    • 4.5 Baths
    • 2,874 Sq Ft

    2632 Tranquility Way, Kissimmee, FL 34746

    Beautiful 6 bedroom home in a calm gated community, Veranda Palms. Has its own private pool and hot tub as well as the association pool and gym available to use.

    Agent Photo

    Ada Rinaudo

    GREEN LIFE PROJECTS LLC

    (321) 483-8911

    2632 Tranquility Way, Kissimmee, FL 34746
  • /8

    $1,700 per month

    • 3 Beds
    • 2 Baths
    • 1,177 Sq Ft
    • House for Rent

    2333 Water View Loop, Kissimmee, FL 34743

    Discover this charming 3-bedroom, 2-bath townhouse, nestled in the highly sought-after Lake Side subdivision in Kissimmee. Just minutes away from major highways, schools, parks, and restaurants, this location is incredibly desirable. The townhouse offers a stunning water view. Act quickly this home won't last long!

    Agent Photo

    Jose De Jesus

    RELIABLE PROPERTY MGMT & SALES

    (321) 475-8496

    2333 Water View Loop, Kissimmee, FL 34743
  • /2

    $665,000 Sold Aug 29, 2025

    • 2,468 Sq Ft
    • $269/SF
    • 3 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2013

    2601 Swoop Cir, Kissimmee, FL 34741

    Welcome to the gated community of Avilla, where this stunning 4-bedroom, 3-bathroom pond-front residence offers resort-style living and timeless design. Built in 2013, this move-in ready home boasts a spacious 3-car garage and features a heated, screened pool with spa, surrounded by lush tropical landscaping and a covered rear porch that offers scenic pond views from the backyard oasis—perfect

    Robyn Richards NEXTHOME LUXE COASTAL

    2601 Swoop Cir, Kissimmee, FL 34741
    • /40

      Est $369,798 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,133 Sq Ft

      366 Blue Lake Cir, Kissimmee, FL 34758

      366 Blue Lake Cir, Kissimmee, FL 34758

Showing Results 1 - 40, Page 1 of 18

Home Trends in Kissimmee, FL

Housing Trends

Median Sale Price
$376,995
Median Single Family Sale Price
$400,000
Median Townhouse Sale Price
$368,990
Median 2 Bedroom Sale Price
$229,000
Median 1 Bedroom Sale Price
$165,000
Average Price Per Sq Ft
$216
Number of Homes for Sale
3,071
Last 12 months Home Sales
5,161
Months of Supply
7.10
Median List Price
$399,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
1%
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