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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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  • 1980 SUMMER CT, KISSIMMEE, FL 34744

    $549,00028 Days on yellowkey   MLS ID: O6392643

    For Sale O6392643 - 1980 SUMMER CT, KISSIMMEE, FL 34744 40 photos

    Bed: 3   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 2687
       Built: 2005   Tax: $6,583 (2025)
    Community: Meadow Spgs
    Single Family


    Estimated Monthly Payment: $3,557 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($549)


    Taxes:$6,583

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2743 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $699,00049 Days on yellowkey   MLS ID: O6386876

    REDUCED by $16,000 (2.2%) on 04/14/2026

    For Sale O6386876 - 2743 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744 54 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2856
       Built: 2005
    Monthly Fee: $195
       Tax: $7,062 (2025)
    Community: Kissimmee Bay
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,614 (change assumption)
    Mortgage ($3,830) + Fees ($195) + Taxes in 2025 ($589)


    Taxes:$7,062

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1994 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $474,00056 Days on yellowkey   MLS ID: S5144463

    For Sale S5144463 - 1994 SPRING SHOWER CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2056
       Built: 2022
    Monthly Fee: $128
       Tax: $7,519 (2025)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $3,352 (change assumption)
    Mortgage ($2,597) + Fees ($128) + Taxes in 2025 ($627)


    Taxes:$7,519

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1874 HICKORY BLUFF RD, KISSIMMEE, FL 34744

    $550,0008 Days on yellowkey   MLS ID: O6398896

    For Sale O6398896 - 1874 HICKORY BLUFF RD, KISSIMMEE, FL 34744 20 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 2017
    Monthly Fee: $12
       Tax: $15,385 (2025)
    Community: Kindred
    Single Family


    Estimated Monthly Payment: $4,308 (change assumption)
    Mortgage ($3,014) + Fees ($12) + Taxes in 2025 ($1,282)


    Taxes:$15,385

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1340 SAWDUST TRL, KISSIMMEE, FL 34744

    $239,90095 Days on yellowkey   MLS ID: G5106887

    For Sale G5106887 - 1340 SAWDUST TRL, KISSIMMEE, FL 34744 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 924
       Built: 1996   Tax: $2,377 (2025)
    Community: Marydia
    Manufactured Home


    Estimated Monthly Payment: $1,513 (change assumption)
    Mortgage ($1,314) + Taxes in 2025 ($198)


    Taxes:$2,377

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2503 HASSONITE ST, KISSIMMEE, FL 34744

    $345,000170 Days on yellowkey   MLS ID: S5137504

    For Sale S5137504 - 2503 HASSONITE ST, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2018
       Built: 2007
    Monthly Fee: $170
       Tax: $1,559 (2024)
    Community: Amber Pointe
    Townhouse


    Estimated Monthly Payment: $2,190 (change assumption)
    Mortgage ($1,890) + Fees ($170) + Taxes in 2024 ($130)


    Taxes:$1,559

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 1378 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $585,0009 Days on yellowkey   MLS ID: R4911041

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

    For Sale R4911041 - 1378 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2147
       Built: 1997   Tax: $3,637 (2025)
    Community: East Lake Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,508 (change assumption)
    Mortgage ($3,205) + Taxes in 2025 ($303)


    Taxes:$3,637

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1135 CHEROKEE DR, KISSIMMEE, FL 34744

    $375,99051 Days on yellowkey   MLS ID: S5144943

    For Sale S5144943 - 1135 CHEROKEE DR, KISSIMMEE, FL 34744 12 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1358
       Built: 1964   Tax: $1,014 (2025)
    Community: Osceola Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($2,060) + Taxes in 2025 ($85)


    Taxes:$1,014

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2776 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $794,900133 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

    $459,00090 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


  • 1719 FLOURISH AVE, KISSIMMEE, FL 34744

    $459,99966 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

    $489,000295 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


  • 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744

    $519,90067 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

    $549,00013 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

    $875,00027 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

    $359,0005 Days 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

    $395,0005 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

    $369,9905 Days 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

    $400,0005 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

    $339,9005 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




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.