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Homes For Sale in Kissimmee 34744 - 290 homes

34744 zip code is located in Osceola County, Florida. Find homes for sale in Kissimmee 34744 from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Kissimmee 34744 homes for sale.

Location: Kissimmee , 34744

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  • 3104 MANDOLIN DR, KISSIMMEE, FL 34744

    $465,0005 Days on yellowkey   MLS ID: S5147810

    For Sale S5147810 - 3104 MANDOLIN DR, KISSIMMEE, FL 34744 76 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 2007
    Monthly Fee: $83
       Tax: $3,388 (2025)
    Community: Turnberry Resv U2
    Single Family


    Estimated Monthly Payment: $2,913 (change assumption)
    Mortgage ($2,548) + Fees ($83) + Taxes in 2025 ($282)


    Taxes:$3,388

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 2661 ELLEN AVE, KISSIMMEE, FL 34744

    $450,0003 Days on yellowkey   MLS ID: O6399716

    For Sale O6399716 - 2661 ELLEN AVE, KISSIMMEE, FL 34744 25 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1864
       Built: 1972   Tax: $5,005 (2025)
    Community: Emerald Lake Colony Unit 3
    Single Family


    Estimated Monthly Payment: $2,883 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($417)


    Taxes:$5,005

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2776 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $794,900130 Days on yellowkey   MLS ID: S5139337

    REDUCED by $24,100 (2.9%) on 04/17/2026

    For Sale S5139337 - 2776 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744 52 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3340
       Built: 2018
    Monthly Fee: $190
       Tax: $5,827 (2025)
    Community: Kissimmee Bay Rep 7
    Single Family


    Estimated Monthly Payment: $5,031 (change assumption)
    Mortgage ($4,356) + Fees ($190) + Taxes in 2025 ($486)


    Taxes:$5,827

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2761 MICHIGAN AVE, KISSIMMEE, FL 34744

    $459,00087 Days on yellowkey   MLS ID: O6375128

    REDUCED by $10,000 (2.1%) on 04/06/2026

    For Sale O6375128 - 2761 MICHIGAN AVE, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 1869
       Built: 1979   Tax: $7,282 (2025)
    Community: Lee Bel Park
    Apartment


    Estimated Monthly Payment: $3,122 (change assumption)
    Mortgage ($2,515) + Taxes in 2025 ($607)


    Taxes:$7,282

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2835 NOBLE CROW DR, KISSIMMEE, FL 34744

    $479,90041 Days on yellowkey   MLS ID: S5145312

    For Sale S5145312 - 2835 NOBLE CROW DR, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2676
       Built: 2020
    Monthly Fee: $93
       Tax: $5,079 (2025)
    Community: Marbella Ph 1
    Single Family


    Estimated Monthly Payment: $3,146 (change assumption)
    Mortgage ($2,630) + Fees ($93) + Taxes in 2025 ($423)


    Taxes:$5,079

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1719 FLOURISH AVE, KISSIMMEE, FL 34744

    $459,99963 Days on yellowkey   MLS ID: O6382782

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale O6382782 - 1719 FLOURISH AVE, KISSIMMEE, FL 34744 5 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2450
       Built: 2021
    Monthly Fee: $80
       Tax: $5,605 (2025)
    Community: Tohoqua Ph 1
    Single Family


    Estimated Monthly Payment: $3,068 (change assumption)
    Mortgage ($2,520) + Fees ($80) + Taxes in 2025 ($467)


    Taxes:$5,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744

    $489,000292 Days on yellowkey   MLS ID: S5130069

    For Sale S5130069 - 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2251
       Built: 2012
    Monthly Fee: $112
       Tax: $4,907 (2024)
    Community: North Point Ph 1A
    Single Family


    Estimated Monthly Payment: $3,200 (change assumption)
    Mortgage ($2,679) + Fees ($112) + Taxes in 2024 ($409)


    Taxes:$4,907

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 1325 CYPRESS ARBOR, KISSIMMEE, FL 34744

    $275,0004 Days on yellowkey   MLS ID: O6398060

    For Sale O6398060 - 1325 CYPRESS ARBOR, KISSIMMEE, FL 34744 15 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 957
       Built: 1986   Tax: $806 (2025)
    Community: Cypress Arbor
    Single Family


    Estimated Monthly Payment: $1,574 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($67)


    Taxes:$806

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744

    $519,90064 Days on yellowkey   MLS ID: S5143801

    For Sale S5143801 - 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2727
       Built: 2023
    Monthly Fee: $130
       Tax: $7,208 (2025)
    Community: Creekside At Boggy Creek Ph 3
    Single Family


    Estimated Monthly Payment: $3,579 (change assumption)
    Mortgage ($2,849) + Fees ($130) + Taxes in 2025 ($601)


    Taxes:$7,208

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2507 WINNERS CIR, KISSIMMEE, FL 34744

    $549,00010 Days on yellowkey   MLS ID: S5147254

    1 Days Off yellowkey (back on 4/18/2026)

    For Sale S5147254 - 2507 WINNERS CIR, KISSIMMEE, FL 34744 98 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1914
       Built: 1999   Tax: $2,483 (2025)
    Community: D S Estates
    Single Family


    Estimated Monthly Payment: $3,215 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($207)


    Taxes:$2,483

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1516 PINE ISLAND RD, KISSIMMEE, FL 34744

    $875,00024 Days on yellowkey   MLS ID: S5145674

    For Sale S5145674 - 1516 PINE ISLAND RD, KISSIMMEE, FL 34744 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2613
       Built: 2026   Tax: $1,385 (2025)
    Community: Regal Point Estates Unit 1
    Single Family


    Estimated Monthly Payment: $4,910 (change assumption)
    Mortgage ($4,794) + Taxes in 2025 ($115)


    Taxes:$1,385

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 216 MAGICAL WAY, KISSIMMEE, FL 34744

    $359,0001 Day on yellowkey   MLS ID: O6396457

    For Sale O6396457 - 216 MAGICAL WAY, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1832
       Built: 2005
    Monthly Fee: $127
       Tax: $4,782 (2025)
    Community: Magic Landings
    Single Family


    Estimated Monthly Payment: $2,493 (change assumption)
    Mortgage ($1,967) + Fees ($127) + Taxes in 2025 ($399)


    Taxes:$4,782

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1823 SUMMER SERENITY DR, KISSIMMEE, FL 34744

    $395,0002 Days on yellowkey   MLS ID: O6400356

    For Sale O6400356 - 1823 SUMMER SERENITY DR, KISSIMMEE, FL 34744 66 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1900
       Built: 2022
    Monthly Fee: $26
       Tax: $6,999 (2024)
    Community: Tohoqua Ph 4A
    Single Family


    Estimated Monthly Payment: $2,774 (change assumption)
    Mortgage ($2,164) + Fees ($26) + Taxes in 2024 ($583)


    Taxes:$6,999

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1631 BITTEROOT ST, KISSIMMEE, FL 34744

    $369,9901 Day on yellowkey   MLS ID: S5147958

    For Sale S5147958 - 1631 BITTEROOT ST, KISSIMMEE, FL 34744 59 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1814
       Built: 2024
    Monthly Fee: $11
       Tax: $5,432 (2025)
    Community: Kindred
    Townhouse


    Estimated Monthly Payment: $2,491 (change assumption)
    Mortgage ($2,027) + Fees ($11) + Taxes in 2025 ($453)


    Taxes:$5,432

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4416 SILVER CREEK ST, KISSIMMEE, FL 34744

    $400,0002 Days on yellowkey   MLS ID: O6398907

    For Sale O6398907 - 4416 SILVER CREEK ST, KISSIMMEE, FL 34744 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2019
    Monthly Fee: $130
       Tax: $4,679 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,712 (change assumption)
    Mortgage ($2,192) + Fees ($130) + Taxes in 2025 ($390)


    Taxes:$4,679

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1874 KATZ CROSSING DR, KISSIMMEE, FL 34744

    $339,9002 Days on yellowkey   MLS ID: S5147573

    For Sale S5147573 - 1874 KATZ CROSSING DR, KISSIMMEE, FL 34744 51 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1870
       Built: 2019
    Monthly Fee: $95
       Tax: $3,374 (2025)
    Community: Kindred Ph 1E
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,239 (change assumption)
    Mortgage ($1,862) + Fees ($95) + Taxes in 2025 ($281)


    Taxes:$3,374

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1895 HICKORY BLUFF RD, KISSIMMEE, FL 34744

    $349,90089 Days on yellowkey   MLS ID: S5142089

    For Sale S5142089 - 1895 HICKORY BLUFF RD, KISSIMMEE, FL 34744 17 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 2017
    Monthly Fee: $11
       Tax: $6,019 (2025)
    Community: Kindred Ph 1C Pb 25 Pgs 127-134 Lot 373
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,430 (change assumption)
    Mortgage ($1,917) + Fees ($11) + Taxes in 2025 ($502)


    Taxes:$6,019

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2718 LUCAS LAKES LN, KISSIMMEE, FL 34744

    $410,00089 Days on yellowkey   MLS ID: O6374248

    For Sale O6374248 - 2718 LUCAS LAKES LN, KISSIMMEE, FL 34744 21 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2407
       Built: 2006
    Monthly Fee: $13
       Tax: $6,877 (2025)
    Community: Remington Prcl O
    Single Family


    Estimated Monthly Payment: $2,833 (change assumption)
    Mortgage ($2,247) + Fees ($13) + Taxes in 2025 ($573)


    Taxes:$6,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 429 JANICE KAY PL, KISSIMMEE, FL 34744

    $450,00041 Days on yellowkey   MLS ID: S5145448

    For Sale S5145448 - 429 JANICE KAY PL, KISSIMMEE, FL 34744 20 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2906
       Built: 2004
    Monthly Fee: $14
       Tax: $2,737 (2024)
    Community: Eagle Point
    Single Family


    Estimated Monthly Payment: $2,708 (change assumption)
    Mortgage ($2,466) + Fees ($14) + Taxes in 2024 ($228)


    Taxes:$2,737

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1752 LEE JANZEN DR, KISSIMMEE, FL 34744

    $599,90015 Days on yellowkey   MLS ID: S5145877

    For Sale S5145877 - 1752 LEE JANZEN DR, KISSIMMEE, FL 34744 57 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3376
       Built: 2005
    Monthly Fee: $190
       Tax: $8,834 (2025)
    Community: Kissimmee Bay
    Single Family


    Estimated Monthly Payment: $4,213 (change assumption)
    Mortgage ($3,287) + Fees ($190) + Taxes in 2025 ($736)


    Taxes:$8,834

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




Why Bother Searching Elsewhere for 34744 Homes for Sale and Other Kissimmee Real Estate?

34744, Kissimmee home, townhome, condo, villa, and other listing rental data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in the 34744 zip code. You can use our website to view Multiple Listing Service (MLS) data on 34744, Kissimmee real estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our 34744, Kissimmee listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.