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Homes For Sale in Kissimmee 34744 - 288 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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  • 1340 SAWDUST TRL, KISSIMMEE, FL 34744

    $239,90090 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


  • 1874 HICKORY BLUFF RD, KISSIMMEE, FL 34744

    $550,0003 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


  • 2045 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $456,9903 Days on yellowkey   MLS ID: O6398932

    For Sale O6398932 - 2045 WALNUT CREEK DR, KISSIMMEE, FL 34744 47 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2447
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,822 (change assumption)
    Mortgage ($2,504) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3824 BLUE DASHER DR, KISSIMMEE, FL 34744

    $499,990319 Days on yellowkey   MLS ID: O6314514

    For Sale O6314514 - 3824 BLUE DASHER DR, KISSIMMEE, FL 34744 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3783
       Built: 2004
    Monthly Fee: $106
       Tax: $6,729 (2024)
    Community: Springlake Village Ph 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,406 (change assumption)
    Mortgage ($2,740) + Fees ($106) + Taxes in 2024 ($561)


    Taxes:$6,729

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2743 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $699,00044 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)


  • 1503 OAK RESERVE DR, KISSIMMEE, FL 34744

    $445,00057 Days on yellowkey   MLS ID: S5144250

    REDUCED by $5,000 (1.1%) on 04/08/2026

    For Sale S5144250 - 1503 OAK RESERVE DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022   Tax: $7,738 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,083 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($645)


    Taxes:$7,738

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: St. Cloud Middle (6-8)


  • 1764 STAMEN DR, KISSIMMEE, FL 34744

    $447,99030 Days on yellowkey   MLS ID: O6391946

    REDUCED by $2,010 (0.4%) on 04/14/2026

    For Sale O6391946 - 1764 STAMEN DR, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1985
       Built: 2023
    Monthly Fee: $160
       Tax: $4,505 (2025)
    Community: Pennyroyal
    Single Family


    Estimated Monthly Payment: $2,990 (change assumption)
    Mortgage ($2,455) + Fees ($160) + Taxes in 2025 ($375)


    Taxes:$4,505

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744

    $489,000290 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


  • 2540 BLOWING BREEZE AVE, KISSIMMEE, FL 34744

    $370,00099 Days on yellowkey   MLS ID: S5141277

    For Sale S5141277 - 2540 BLOWING BREEZE AVE, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1700
       Built: 2021
    Monthly Fee: $154
       Tax: $6,407 (2025)
    Community: Tohoqua Ph 1B
    Townhouse


    Estimated Monthly Payment: $2,715 (change assumption)
    Mortgage ($2,027) + Fees ($154) + Taxes in 2025 ($534)


    Taxes:$6,407

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1590 BARBERRY DR, KISSIMMEE, FL 34744

    $459,900239 Days on yellowkey   MLS ID: S5133065

    REDUCED by $30,000 (6.1%) on 04/14/2026

    For Sale S5133065 - 1590 BARBERRY DR, KISSIMMEE, FL 34744 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2142
       Built: 2023
    Monthly Fee: $15
       Tax: $8,284 (2024)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,225 (change assumption)
    Mortgage ($2,520) + Fees ($15) + Taxes in 2024 ($690)


    Taxes:$8,284

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: None


  • 1540 GRANDVIEW BLVD, KISSIMMEE, FL 34744

    $949,90063 Days on yellowkey   MLS ID: S5143565

    REDUCED by $50,000 (5.0%) on 04/14/2026

    For Sale S5143565 - 1540 GRANDVIEW BLVD, KISSIMMEE, FL 34744 56 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5207
       Built: 1981   Tax: $7,032 (2025)
    Community: Regal Oak Shores Unit 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,791 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($586)


    Taxes:$7,032

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2518 BOWMER DR, KISSIMMEE, FL 34744

    $359,900619 Days on yellowkey   MLS ID: S5109889

    For Sale S5109889 - 2518 BOWMER DR, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1523
       Built: 1982   Tax: $1,246 (2025)
    Community: Mill Run Unit 3
    Single Family


    Estimated Monthly Payment: $2,076 (change assumption)
    Mortgage ($1,972) + Taxes in 2025 ($104)


    Taxes:$1,246

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2728 PORTCHESTER CT, KISSIMMEE, FL 34744

    $399,900338 Days on yellowkey   MLS ID: S5126915

    For Sale S5126915 - 2728 PORTCHESTER CT, KISSIMMEE, FL 34744 14 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2005
    Monthly Fee: $7
       Tax: $6,060 (2024)
    Community: Somerset
    Single Family


    Estimated Monthly Payment: $2,703 (change assumption)
    Mortgage ($2,191) + Fees ($7) + Taxes in 2024 ($505)


    Taxes:$6,060

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2761 MICHIGAN AVE, KISSIMMEE, FL 34744

    $459,00085 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


  • 1705 BRIDGETS CT, KISSIMMEE, FL 34744

    $565,00039 Days on yellowkey   MLS ID: S5145159

    REDUCED by $10,000 (1.7%) on 04/14/2026

    For Sale S5145159 - 1705 BRIDGETS CT, KISSIMMEE, FL 34744 57 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2994
       Built: 2004
    Monthly Fee: $190
       Tax: $5,502 (2025)
    Community: M3 At Kissimmee Bay
    Single Family


    Estimated Monthly Payment: $3,744 (change assumption)
    Mortgage ($3,096) + Fees ($190) + Taxes in 2025 ($459)


    Taxes:$5,502

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2963 SERA BELLA WAY, KISSIMMEE, FL 34744

    $515,00039 Days on yellowkey   MLS ID: S5144389

    For Sale S5144389 - 2963 SERA BELLA WAY, KISSIMMEE, FL 34744 74 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2416
       Built: 2016
    Monthly Fee: $120
       Tax: $5,072 (2025)
    Community: Sera Bella
    Single Family


    Estimated Monthly Payment: $3,365 (change assumption)
    Mortgage ($2,822) + Fees ($120) + Taxes in 2025 ($423)


    Taxes:$5,072

    Elementary School: Ventura Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Parkway Middle


  • 1737 KATO WAY, KISSIMMEE, FL 34744

    $355,00016 Days on yellowkey   MLS ID: TB8492414

    For Sale TB8492414 - 1737 KATO WAY, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1935
       Built: 2018
    Monthly Fee: $168
       Tax: $4,031 (2025)
    Community: Heritage Run
    Townhouse


    Estimated Monthly Payment: $2,449 (change assumption)
    Mortgage ($1,945) + Fees ($168) + Taxes in 2025 ($336)


    Taxes:$4,031

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2061 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $458,99010 Days on yellowkey   MLS ID: O6396945

    2 Days Off yellowkey (back on 4/14/2026)

    For Sale O6396945 - 2061 WALNUT CREEK DR, KISSIMMEE, FL 34744 50 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2447
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,833 (change assumption)
    Mortgage ($2,515) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1904 TOHOQUA BLVD, KISSIMMEE, FL 34744

    $365,00043 Days on yellowkey   MLS ID: O6387203

    REDUCED by $10,000 (2.7%) on 04/14/2026

    SHORT SALE O6387203 - 1904 TOHOQUA BLVD, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2023
    Monthly Fee: $140
       Tax: $6,407 (2025)
    Community: Tohoqua Ph 6
    Townhouse


    Estimated Monthly Payment: $2,674 (change assumption)
    Mortgage ($2,000) + Fees ($140) + Taxes in 2025 ($534)


    Taxes:$6,407

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Harmony Middle


  • 2362 SOUTHBURY DR, KISSIMMEE, FL 34744

    $394,490158 Days on yellowkey   MLS ID: O6359381

    6 Days Off yellowkey (back on 1/12/2026)

    For Sale O6359381 - 2362 SOUTHBURY DR, KISSIMMEE, FL 34744 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $130
       Tax: $2,384 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,490 (change assumption)
    Mortgage ($2,162) + Fees ($130) + Taxes in 2025 ($199)


    Taxes:$2,384

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)




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.