10

Downtown Kissimmee Houses for Sale

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  • /32

    $434,990

    • 3 Beds
    • 2 Baths
    • 1,614 Sq Ft

    1792 Bull Hill Rd, Kindred, FL 34744

    COMPLETE WITH FURNITURE!! Welcome to your dream home in a resort-style community! This beautiful, brand-new 3-bedroom, 2-bathroom residence is move-in ready and fully equipped for comfort and style. Enjoy a modern open-concept layout with new stainless steel appliances, elegant finishes, and completely new furniture—all thoughtfully selected for luxury and functionality.Located in a sought-after

    Idejair Pereira EMPIRE NETWORK REALTY

    1792 Bull Hill Rd, Kindred, FL 34744
  • /23

    $369,900

    • 3 Beds
    • 2 Baths
    • 1,685 Sq Ft

    1211 Lehigh St, Kissimmee, FL 34744

    Welcome to this beautifully updated and upgraded pool home in Kissimmee! This spacious residence features an upgraded kitchen with elegant gold fixtures and stainless steel appliances, including a range, refrigerator, dishwasher, and microwave. The home offers multiple living spaces, including a living room, family room, and dining room, providing plenty of room to relax and entertain. With no

    Elizabeth Santiago ALLEGIANT MANAGEMENT GROUP INC

    1211 Lehigh St, Kissimmee, FL 34744
  • /23

    $344,900

    • 4 Beds
    • 3 Baths
    • 1,438 Sq Ft

    1209 Marygon St, Kissimmee, FL 34744

    Welcome to 1209 Marygon Street – where comfort, convenience, and character come together! This beautifully maintained 4-bedroom, 3 bathroom home features two spacious master suites, ideal for multi-generational living or guest privacy.Enjoy hurricane-rated impact windows and a whole-house water filtration system, offering peace of mind and everyday comfort. The bright and open layout

    Yeni Castellanos LA ROSA REALTY ORLANDO LLC

    1209 Marygon St, Kissimmee, FL 34744
  • /29

    $339,000

    • 4 Beds
    • 2 Baths
    • 1,554 Sq Ft

    308 E Orange St, Kissimmee, FL 34744

    This property has undergone a complete renovation from top to bottom, offering a fully updated interior. It features a NEW ROOF installed in 2024, along with brand-new energy-efficient WINDOWS, doors, blinds, stainless steel appliances, NEW AC, Updated Electrical and plumbing, Water heater, LUXURY VINYL PLANK throughout the home. Freshly painted on the exterior and interior. Home features 4

    Darshani Lokhnath KELLER WILLIAMS ADVANTAGE III

    308 E Orange St, Kissimmee, FL 34744
  • /25

    $445,000

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    1312 Axel Graeson Ave, Kissimmee, FL 34744

    Welcome to this stunning 3-bedroom, 2-bathroom single-family home located in one of South Florida’s most desirable communities — Weston. This move-in ready home features a bright, open-concept layout, vaulted ceilings, and elegant finishes throughout. The spacious kitchen offers ample cabinetry and overlooks a cozy family area, perfect for gatherings. Step outside to a private, beautifully

    Alejandro Rodriguez AROD PARTNERS REALTY

    1312 Axel Graeson Ave, Kissimmee, FL 34744
  • /69

    $449,900

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft

    302 E Drury Ave, Kissimmee, FL 34744

    Just Updated! Welcome To 302 E Drury Avenue – A One-Of-A-Kind Lakefront Property Featuring A Beautiful 3-Bedroom, 2-Bath Home Paired With An Impressive 1,000+ Sqft Detached Structure, Complete With Water And Electric Connections. Perfect For A Home Office, Guest Suite, Studio, Or Future Income Potential. Enjoy Peaceful Waterfront Living In An Established Neighborhood, With An Open Interior

    Chas Barboza RADIUS REALTY GROUP LLC

    302 E Drury Ave, Kissimmee, FL 34744
  • /24

    $390,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,516 Sq Ft

    1982 King Ranch St, Kindred, FL 34744

    This 2023-built 3-bed, 2-bath home with a 2-car garage offers stylish upgrades and flexible living. Features include luxury vinyl flooring, new kitchen and bathroom countertops, updated faucets, and a mini-split AC in the garage? Ideal for a gym or workspace.Located in a resort-style community with a clubhouse, fitness center, pool, tennis courts, park, and playground.Currently leased

    Christopher Dasilva DALTON WADE INC

    1982 King Ranch St, Kindred, FL 34744
  • /30

    $239,900

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft

    207 E Orange St, Kissimmee, FL 34744

    Come check out this historic mature home in the downtown Kissimmee area. House sits on one of the larger lots in this neighborhood. Property features a front and back porch, large backyard including an oversize shed among large mature trees. Newer Lennox A/C unit, Rheem Performance line water heater, city water line replaced 2 years ago. Fixer upper opportunity.

    Danny Ramos ONE FAMILY REALTY

    207 E Orange St, Kissimmee, FL 34744
  • /32

    $220,000

    • 3 Beds
    • 2 Baths
    • 1,048 Sq Ft

    211 N Randolph Ave, Kissimmee, FL 34741

    **PRICE ADJUSTMENT** An "oldie but a goodie"! This 1936 house has great bones and has withstood MANY storms over the years. Previously on a parcel with an adjacent home which has now been separated and is PRICED TO SELL. It is in a great location convenient to the Osceola County Courthouse and historic and quaint downtown Kissimmee. Just a short drive to the Florida Turnpike and central Florida

    Dawn Grigsby EXP REALTY LLC

    211 N Randolph Ave, Kissimmee, FL 34741
  • /34

    $310,000

    • 3 Beds
    • 2 Baths
    • 1,064 Sq Ft

    1006 Penfield St, Kissimmee, FL 34741

    One of a kind property, recently remodel Historical home in the heart of downtown Kissimmee. Lovely and cozy 3 bedrooms, 2 bathrooms with a light full open plan from livingroom to kitchen. This property offers 1/3 of an acre with no HOA, the backyard is fully fenced and clear for any project you have in mind, from a shed to a storage or even a mothers in law. Only one neighbor on the right side,

    Lorena Castillo LPT REALTY, LLC

    1006 Penfield St, Kissimmee, FL 34741

Why Live in Downtown Kissimmee

Downtown Kissimmee, known for its historic charm and proximity to Walt Disney World Resorts, offers a suburban lifestyle with a city-like feel. The neighborhood is bustling with foot traffic, featuring a variety of shops and restaurants. Notable dining options include Willy's Wieners, Abracadabra Ice Cream Factory, and Three Sisters Speakeasy. The area is home to the largest independently owned restaurant district in Central Florida. Residents enjoy walking past vintage buildings, colorful murals, and landmarks like the Monument of States and the Osceola County Historical Courthouse. For shopping, Lanier's Historic Downtown Marketplace and Casa Del Artesano are popular spots. Outdoor enthusiasts frequent Lakefront Park for recreation, Brinson Park for fishing, and Oak Street Park & Community Center for gym and tennis facilities. Shingle Creek Regional Park offers natural beauty and hosts many city festivals, including the Taste of Kissimmee and the Festival of Lights parade. Homes range from contemporary bungalows to midsized multi-story houses, with newer condos also available. Traffic congestion is common, but improvements are planned, and a parking garage near the lakefront aids commuters. Kissimmee Gateway Airport is nearby, and Orlando International Airport is 15 miles away.

Home Trends in Downtown Kissimmee, FL

Housing Trends

Median Sale Price
$345,445
Median Single Family Sale Price
$320,990
Median Townhouse Sale Price
$379,990
Average Price Per Sq Ft
$163
Number of Homes for Sale
1
Last 12 months Home Sales
18
Months of Supply
0.70
Median List Price
$362,745
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
31%
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