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Homes For Sale in Kissimmee 34744 - 376 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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  • 1804 HOWARD MESA DR, KISSIMMEE, FL 34744

    $389,99056 Days on yellowkey   MLS ID: O6409252

    REDUCED by $5,000 (1.3%) on 07/02/2026

    For Sale O6409252 - 1804 HOWARD MESA DR, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,455 (change assumption)
    Mortgage ($2,137) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1687 PARK SIDE AVE, KISSIMMEE, FL 34744

    $436,99033 Days on yellowkey   MLS ID: S5151674

    REDUCED by $10 (0.0%) on 07/05/2026

    For Sale S5151674 - 1687 PARK SIDE AVE, KISSIMMEE, FL 34744 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022
    Monthly Fee: $11
       Tax: $7,143 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,001 (change assumption)
    Mortgage ($2,394) + Fees ($11) + Taxes in 2025 ($595)


    Taxes:$7,143

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1425 RIVIERA DR, KISSIMMEE, FL 34744

    $944,900131 Days on yellowkey   MLS ID: O6386384

    For Sale O6386384 - 1425 RIVIERA DR, KISSIMMEE, FL 34744 82 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4654
       Built: 2002
    Monthly Fee: $183
       Tax: $7,220 (2025)
    Community: Regal Bay
    Single Family


    Estimated Monthly Payment: $5,962 (change assumption)
    Mortgage ($5,177) + Fees ($183) + Taxes in 2025 ($602)


    Taxes:$7,220

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1933 BELLKNOLL LN, KISSIMMEE, FL 34744

    $415,00043 Days on yellowkey   MLS ID: O6411567

    REDUCED by $14,000 (3.3%) on 07/02/2026

    For Sale O6411567 - 1933 BELLKNOLL LN, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2020
    Monthly Fee: $11
       Tax: $6,080 (2025)
    Community: Kindred
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,792 (change assumption)
    Mortgage ($2,274) + Fees ($11) + Taxes in 2025 ($507)


    Taxes:$6,080

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: None


  • 4406 SILVER CREEK ST, KISSIMMEE, FL 34744

    $448,00017 Days on yellowkey   MLS ID: O6418739

    For Sale O6418739 - 4406 SILVER CREEK ST, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1878
       Built: 2019
    Monthly Fee: $94
       Tax: $4,072 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Single Family


    Estimated Monthly Payment: $2,888 (change assumption)
    Mortgage ($2,455) + Fees ($94) + Taxes in 2025 ($339)


    Taxes:$4,072

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2708 PRESTWICK LN, KISSIMMEE, FL 34744

    $387,00064 Days on yellowkey   MLS ID: S5149647

    2 Days Off yellowkey (back on 6/3/2026)

    INCREASED by $7,000 (1.8%) on 05/22/2026

    For Sale S5149647 - 2708 PRESTWICK LN, KISSIMMEE, FL 34744 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 2004
    Monthly Fee: $92
       Tax: $7,102 (2025)
    Community: Remington Prcl M1
    Single Family


    Estimated Monthly Payment: $2,804 (change assumption)
    Mortgage ($2,120) + Fees ($92) + Taxes in 2025 ($592)


    Taxes:$7,102

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1009 CHALCEDONY ST, KISSIMMEE, FL 34744

    $315,00038 Days on yellowkey   MLS ID: O6412394

    REDUCED by $10,000 (3.1%) on 07/03/2026

    For Sale O6412394 - 1009 CHALCEDONY ST, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1683
       Built: 2010
    Monthly Fee: $170
       Tax: $3,128 (2025)
    Community: Amber Pointe
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,157 (change assumption)
    Mortgage ($1,726) + Fees ($170) + Taxes in 2025 ($261)


    Taxes:$3,128

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744

    $499,900237 Days on yellowkey   MLS ID: S5138827

    REDUCED by $15,100 (2.9%) on 06/14/2026

    For Sale S5138827 - 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3099
       Built: 2017
    Monthly Fee: $11
       Tax: $5,957 (2024)
    Community: Kindred Ph 1C
    Single Family


    Estimated Monthly Payment: $3,246 (change assumption)
    Mortgage ($2,739) + Fees ($11) + Taxes in 2024 ($496)


    Taxes:$5,957

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2743 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $635,000132 Days on yellowkey   MLS ID: O6386876

    1 Days Off yellowkey (back on 7/3/2026)

    REDUCED by $14,900 (2.3%) on 06/26/2026

    For Sale O6386876 - 2743 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744 56 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: $4,263 (change assumption)
    Mortgage ($3,479) + 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)


  • 302 E DRURY AVE, KISSIMMEE, FL 34744

    $368,00042 Days on yellowkey   MLS ID: O6411839

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6411839 - 302 E DRURY AVE, KISSIMMEE, FL 34744 42 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1528
       Built: 1950   Tax: $778 (2025)
    Community: Cape Breeze
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,081 (change assumption)
    Mortgage ($2,016) + Taxes in 2025 ($65)


    Taxes:$778

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1802 BLISSFUL DR, KISSIMMEE, FL 34744

    $639,90033 Days on yellowkey   MLS ID: O6415660

    1 Days Off yellowkey (back on 6/15/2026)

    For Sale O6415660 - 1802 BLISSFUL DR, KISSIMMEE, FL 34744 61 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3407
       Built: 2021
    Monthly Fee: $7
       Tax: $10,565 (2025)
    Community: Tohoqua Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,394 (change assumption)
    Mortgage ($3,506) + Fees ($7) + Taxes in 2025 ($880)


    Taxes:$10,565

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1959 CACUTTA WAY, KISSIMMEE, FL 34744

    $387,00039 Days on yellowkey   MLS ID: S5151373

    REDUCED by $13,000 (3.3%) on 07/03/2026

    SHORT SALE S5151373 - 1959 CACUTTA WAY, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2023
    Monthly Fee: $11
       Tax: $7,033 (2025)
    Community: Kindred
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,120) + Fees ($11) + Taxes in 2025 ($586)


    Taxes:$7,033

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Harmony Middle


  • 1010 VAN LIEU ST, KISSIMMEE, FL 34744

    $318,50055 Days on yellowkey   MLS ID: O6409485

    REDUCED by $6,000 (1.8%) on 07/03/2026

    For Sale O6409485 - 1010 VAN LIEU ST, KISSIMMEE, FL 34744 12 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1062
       Built: 1986   Tax: $3,618 (2025)
    Community: Kissimmee Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,047 (change assumption)
    Mortgage ($1,745) + Taxes in 2025 ($302)


    Taxes:$3,618

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1540 GRANDVIEW BLVD, KISSIMMEE, FL 34744

    $899,000151 Days on yellowkey   MLS ID: S5143565

    0 Days Off yellowkey (back on 6/15/2026)

    REDUCED by $25,900 (2.8%) on 06/01/2026

    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: $5,512 (change assumption)
    Mortgage ($4,926) + Taxes in 2025 ($586)


    Taxes:$7,032

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744

    $539,900111 Days on yellowkey   MLS ID: O6390966

    0 Days Off yellowkey (back on 6/6/2026)

    REDUCED by $5,000 (0.9%) on 05/23/2026

    For Sale O6390966 - 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744 78 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 2017
    Monthly Fee: $11
       Tax: $7,067 (2025)
    Community: Kindred Ph 1A & 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,558 (change assumption)
    Mortgage ($2,958) + Fees ($11) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2590 BORINQUEN DR, KISSIMMEE, FL 34744

    $560,00012 Days on yellowkey   MLS ID: O6422091

    For Sale O6422091 - 2590 BORINQUEN DR, KISSIMMEE, FL 34744 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2118
       Built: 1978   Tax: $5,211 (2025)
    Community: Greenville Estates
    Single Family


    Estimated Monthly Payment: $3,503 (change assumption)
    Mortgage ($3,068) + Taxes in 2025 ($434)


    Taxes:$5,211

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1860 SAHA CT, KISSIMMEE, FL 34744

    $653,40012 Days on yellowkey   MLS ID: R4911559

    For Sale R4911559 - 1860 SAHA CT, KISSIMMEE, FL 34744 1 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2869
       Built: 1980   Tax: $3,676 (2025)
    Community: Regal Oak Shores Unit 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,887 (change assumption)
    Mortgage ($3,580) + Taxes in 2025 ($306)


    Taxes:$3,676

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2668 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $395,00050 Days on yellowkey   MLS ID: S5150227

    0 Days Off yellowkey (back on 7/2/2026)

    For Sale S5150227 - 2668 WILLOW GLEN CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 2003
    Monthly Fee: $23
       Tax: $6,164 (2025)
    Community: Gleneagles
    Single Family


    Estimated Monthly Payment: $2,701 (change assumption)
    Mortgage ($2,164) + Fees ($23) + Taxes in 2025 ($514)


    Taxes:$6,164

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1001 LA MIRADA CT, KISSIMMEE, FL 34744

    $355,000120 Days on yellowkey   MLS ID: O6391089

    REDUCED by $8,000 (2.2%) on 06/26/2026

    For Sale O6391089 - 1001 LA MIRADA CT, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1626
       Built: 2021   Tax: $3,315 (2025)
    Community: Lago Buendia Ph 1
    Townhouse


    Estimated Monthly Payment: $2,221 (change assumption)
    Mortgage ($1,945) + Taxes in 2025 ($276)


    Taxes:$3,315

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1872 HOWARD MESA DR, KISSIMMEE, FL 34744

    $409,99033 Days on yellowkey   MLS ID: O6416128

    REDUCED by $6,000 (1.4%) on 07/02/2026

    For Sale O6416128 - 1872 HOWARD MESA DR, KISSIMMEE, FL 34744 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,564 (change assumption)
    Mortgage ($2,246) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    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.