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Homes For Sale in Kissimmee 34744 - 355 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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  • 2273 SOUTHBURY DRIVE, KISSIMMEE, FL 34744

    $374,49014 Days on yellowkey   MLS ID: O6412192

    1 Days Off yellowkey (back on 6/11/2026)

    REDUCED by $2,000 (0.5%) on 06/08/2026

    For Sale O6412192 - 2273 SOUTHBURY DRIVE, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $161
       Tax: $1,920 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,373 (change assumption)
    Mortgage ($2,052) + Fees ($161) + Taxes in 2025 ($160)


    Taxes:$1,920

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1740 NEPTUNE RD, KISSIMMEE, FL 34744

    $435,000129 Days on yellowkey   MLS ID: O6379685

    For Sale O6379685 - 1740 NEPTUNE RD, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2013
       Built: 1966   Tax: $1,925 (2025)
    Community: Neptune Shores 1
    Single Family


    Estimated Monthly Payment: $2,544 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($160)


    Taxes:$1,925

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 339 MAGICAL WAY, KISSIMMEE, FL 34744

    $370,0003 Days on yellowkey   MLS ID: TB8517566

    0 Days Off yellowkey (back on 6/11/2026)

    SHORT SALE TB8517566 - 339 MAGICAL WAY, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1797
       Built: 2006
    Monthly Fee: $50
       Tax: $4,257 (2024)
    Community: Magic Landings Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,432 (change assumption)
    Mortgage ($2,027) + Fees ($50) + Taxes in 2024 ($355)


    Taxes:$4,257

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2640 SERENITY GARDEN DRIVE, KISSIMMEE, FL 34744

    $549,14074 Days on yellowkey   MLS ID: O6393207

    0 Days Off yellowkey (back on 4/10/2026)

    For Sale O6393207 - 2640 SERENITY GARDEN DRIVE, KISSIMMEE, FL 34744 32 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2894
       Built: 2025
    Monthly Fee: $7
       Tax: $1,329 (2025)
    Community: Tohoqua
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,127 (change assumption)
    Mortgage ($3,009) + Fees ($7) + Taxes in 2025 ($111)


    Taxes:$1,329

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2743 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $649,900101 Days on yellowkey   MLS ID: O6386876

    REDUCED by $15,100 (2.3%) on 06/11/2026

    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: $4,345 (change assumption)
    Mortgage ($3,561) + 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)


  • 237 STRATHMORE CIR, KISSIMMEE, FL 34744

    $424,90040 Days on yellowkey   MLS ID: O6403214

    REDUCED by $10,100 (2.3%) on 06/11/2026

    For Sale O6403214 - 237 STRATHMORE CIR, KISSIMMEE, FL 34744 55 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2278
       Built: 1999
    Monthly Fee: $18
       Tax: $4,632 (2025)
    Community: Remington Ph 1 Tr B
    Single Family


    Estimated Monthly Payment: $2,732 (change assumption)
    Mortgage ($2,328) + Fees ($18) + Taxes in 2025 ($386)


    Taxes:$4,632

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1453 TAOS AVE, KISSIMMEE, FL 34744

    $445,0009 Days on yellowkey   MLS ID: S5151107

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale S5151107 - 1453 TAOS AVE, KISSIMMEE, FL 34744 47 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2601
       Built: 2018
    Monthly Fee: $11
       Tax: $6,956 (2025)
    Community: Kindred
    Single Family


    Estimated Monthly Payment: $3,029 (change assumption)
    Mortgage ($2,438) + Fees ($11) + Taxes in 2025 ($580)


    Taxes:$6,956

    Elementary School: Neptune Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 302 E DRURY AVE, KISSIMMEE, FL 34744

    $368,00011 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


  • 2015 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $412,000338 Days on yellowkey   MLS ID: S5130256

    For Sale S5130256 - 2015 SPRING SHOWER CIR, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2054
       Built: 2022
    Monthly Fee: $128
       Tax: $7,088 (2024)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $2,976 (change assumption)
    Mortgage ($2,257) + Fees ($128) + Taxes in 2024 ($591)


    Taxes:$7,088

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 930 SHORE DR, KISSIMMEE, FL 34744

    $644,90025 Days on yellowkey   MLS ID: TB8510529

    REDUCED by $30,000 (4.4%) on 06/11/2026

    For Sale TB8510529 - 930 SHORE DR, KISSIMMEE, FL 34744 23 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3269
       Built: 1958   Tax: $3,326 (2025)
    Community: Cypress Shores Rep
    Single Family


    Estimated Monthly Payment: $3,811 (change assumption)
    Mortgage ($3,534) + Taxes in 2025 ($277)


    Taxes:$3,326

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3014 SERA BELLA WAY, KISSIMMEE, FL 34744

    $515,00012 Days on yellowkey   MLS ID: S5150837

    For Sale S5150837 - 3014 SERA BELLA WAY, KISSIMMEE, FL 34744 41 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2529
       Built: 2016
    Monthly Fee: $113
       Tax: $713 (2025)
    Community: Sera Bella
    Single Family


    Estimated Monthly Payment: $2,994 (change assumption)
    Mortgage ($2,822) + Fees ($113) + Taxes in 2025 ($59)


    Taxes:$713

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1420 EMERALD DR, KISSIMMEE, FL 34744

    $489,000100 Days on yellowkey   MLS ID: O6386884

    1 Days Off yellowkey (back on 6/11/2026)

    REDUCED by $10,000 (2.0%) on 06/06/2026

    For Sale O6386884 - 1420 EMERALD DR, KISSIMMEE, FL 34744 58 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1857
       Built: 1973   Tax: $3,310 (2025)
    Community: Emerald Lake Colony Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,955 (change assumption)
    Mortgage ($2,679) + Taxes in 2025 ($276)


    Taxes:$3,310

    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

    $944,900100 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


  • 498 MARLLO RD, KISSIMMEE, FL 34744

    $640,00047 Days on yellowkey   MLS ID: S5147436

    For Sale S5147436 - 498 MARLLO RD, KISSIMMEE, FL 34744 22 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1956
       Built: 2026   Tax: $434 (2025)
    Community: Florida Fruit Belt Sales Company No 1
    Single Family


    Estimated Monthly Payment: $3,543 (change assumption)
    Mortgage ($3,507) + Taxes in 2025 ($36)


    Taxes:$434

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3824 BLUE DASHER DR, KISSIMMEE, FL 34744

    $499,990376 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


  • 109 THORNBURY DR, KISSIMMEE, FL 34744

    $349,90071 Days on yellowkey   MLS ID: O6395896

    2 Days Off yellowkey (back on 5/13/2026)

    REDUCED by $10,100 (2.8%) on 05/05/2026

    For Sale O6395896 - 109 THORNBURY DR, KISSIMMEE, FL 34744 18 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1622
       Built: 2003
    Monthly Fee: $14
       Tax: $6,074 (2025)
    Community: Remington Prcl H Ph 1
    Single Family


    Estimated Monthly Payment: $2,437 (change assumption)
    Mortgage ($1,917) + Fees ($14) + Taxes in 2025 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2664 EMERALD LAKE CT #2664, KISSIMMEE, FL 34744

    $239,0002 Days on yellowkey   MLS ID: S5150953

    For Sale S5150953 - 2664 EMERALD LAKE CT #2664, KISSIMMEE, FL 34744 74 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 999
       Built: 1987
    Monthly Fee: $330
       Tax: $616 (2025)
    Community: Villas Of Emerald Lake
    Condo


    Estimated Monthly Payment: $1,691 (change assumption)
    Mortgage ($1,310) + Fees ($330) + Taxes in 2025 ($51)


    Taxes:$616

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2713 BARNSLEY LN, KISSIMMEE, FL 34744

    $415,0003 Days on yellowkey   MLS ID: S5151648

    For Sale S5151648 - 2713 BARNSLEY LN, KISSIMMEE, FL 34744 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1993
       Built: 1998
    Monthly Fee: $14
       Tax: $6,501 (2025)
    Community: Remington Ph 1 Tr F
    Single Family


    Estimated Monthly Payment: $2,830 (change assumption)
    Mortgage ($2,274) + Fees ($14) + Taxes in 2025 ($542)


    Taxes:$6,501

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2356 ROYALE OAKS BLVD, KISSIMMEE, FL 34744

    $425,0003 Days on yellowkey   MLS ID: S5151604

    For Sale S5151604 - 2356 ROYALE OAKS BLVD, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1714
       Built: 1989   Tax: $4,158 (2025)
    Community: Royale Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $2,675 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($347)


    Taxes:$4,158

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1850 CHAUCER WAY, KISSIMMEE, FL 34744

    $405,0004 Days on yellowkey   MLS ID: S5151405

    For Sale S5151405 - 1850 CHAUCER WAY, KISSIMMEE, FL 34744 19 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1828
       Built: 1988
    Monthly Fee: $13
       Tax: $5,352 (2025)
    Community: Brighton Place
    Single Family


    Estimated Monthly Payment: $2,678 (change assumption)
    Mortgage ($2,219) + Fees ($13) + Taxes in 2025 ($446)


    Taxes:$5,352

    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.