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Homes For Sale in Kissimmee 34744 - 272 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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  • 2761 MICHIGAN AVE, KISSIMMEE, FL 34744

    $459,00082 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

    $565,00036 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)


  • 1874 HICKORY BLUFF RD, KISSIMMEE, FL 34744

    $550,000Listed 04/14/2026 10:39AM   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


  • 2963 SERA BELLA WAY, KISSIMMEE, FL 34744

    $515,00036 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


  • 2045 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $456,990Listed 04/14/2026 10:35AM   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


  • 1737 KATO WAY, KISSIMMEE, FL 34744

    $355,00013 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


  • 1568 E OAK LEAF LN, KISSIMMEE, FL 34744

    $464,00078 Days on yellowkey   MLS ID: O6376960

    For Sale O6376960 - 1568 E OAK LEAF LN, KISSIMMEE, FL 34744 32 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1845
       Built: 1975   Tax: $4,836 (2025)
    Community: Heather Oaks
    Single Family


    Estimated Monthly Payment: $2,945 (change assumption)
    Mortgage ($2,542) + Taxes in 2025 ($403)


    Taxes:$4,836

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2061 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $458,9907 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

    $365,00040 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

    $394,490155 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)


  • 1870 KING EDWARD DR, KISSIMMEE, FL 34744

    $599,90050 Days on yellowkey   MLS ID: O6384598

    1 Days Off yellowkey (back on 3/8/2026)

    For Sale O6384598 - 1870 KING EDWARD DR, KISSIMMEE, FL 34744 38 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2760
       Built: 1988   Tax: $3,177 (2025)
    Community: Kings Point
    Single Family


    Estimated Monthly Payment: $3,552 (change assumption)
    Mortgage ($3,287) + Taxes in 2025 ($265)


    Taxes:$3,177

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1378 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $585,0001 Day on yellowkey   MLS ID: R4911041

    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


  • 1563 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $360,000Listed 04/13/2026 10:19PM   MLS ID: S5147463

    SHORT SALE S5147463 - 1563 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1802
       Built: 2023
    Monthly Fee: $10
       Tax: $7,403 (2025)
    Community: Tohoqua Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,599 (change assumption)
    Mortgage ($1,973) + Fees ($10) + Taxes in 2025 ($617)


    Taxes:$7,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2538 CROWN RIDGE CIR, KISSIMMEE, FL 34744

    $365,000163 Days on yellowkey   MLS ID: O6357310

    REDUCED by $5,900 (1.6%) on 04/14/2026

    For Sale O6357310 - 2538 CROWN RIDGE CIR, KISSIMMEE, FL 34744 15 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 2001
    Monthly Fee: $14
       Tax: $2,928 (2024)
    Community: Remington Prcl H Ph 1
    Single Family


    Estimated Monthly Payment: $2,258 (change assumption)
    Mortgage ($2,000) + Fees ($14) + Taxes in 2024 ($244)


    Taxes:$2,928

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2958 SERA BELLA WAY, KISSIMMEE, FL 34744

    $525,000165 Days on yellowkey   MLS ID: OM712701

    For Sale OM712701 - 2958 SERA BELLA WAY, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2280
       Built: 2016
    Monthly Fee: $84
       Tax: $3,670 (2024)
    Community: Sera Bella
    Single Family


    Estimated Monthly Payment: $3,266 (change assumption)
    Mortgage ($2,877) + Fees ($84) + Taxes in 2024 ($306)


    Taxes:$3,670

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2619 PEACE OF MIND AVE, KISSIMMEE, FL 34744

    $483,00067 Days on yellowkey   MLS ID: O6380357

    REDUCED by $6,000 (1.2%) on 04/13/2026

    For Sale O6380357 - 2619 PEACE OF MIND AVE, KISSIMMEE, FL 34744 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2025
    Monthly Fee: $10
       Tax: $3,729 (2025)
    Community: Tohoqua 50S
    Single Family


    Estimated Monthly Payment: $2,967 (change assumption)
    Mortgage ($2,647) + Fees ($10) + Taxes in 2025 ($311)


    Taxes:$3,729

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1909 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $318,00092 Days on yellowkey   MLS ID: O6372925

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale O6372925 - 1909 SPRING SHOWER CIR, KISSIMMEE, FL 34744 32 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1545
       Built: 2024
    Monthly Fee: $220
       Tax: $4,300 (2025)
    Community: Tohoqua Ph 5B
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $2,321 (change assumption)
    Mortgage ($1,742) + Fees ($220) + Taxes in 2025 ($358)


    Taxes:$4,300

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $457,00047 Days on yellowkey   MLS ID: S5144261

    For Sale S5144261 - 1595 SHADY OAK DR, KISSIMMEE, FL 34744 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2116
       Built: 1981   Tax: $4,757 (2025)
    Community: Regal Oak Shores Unit 6
    Single Family


    Estimated Monthly Payment: $2,900 (change assumption)
    Mortgage ($2,504) + Taxes in 2025 ($396)


    Taxes:$4,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1459 OAK LEAF LN, KISSIMMEE, FL 34744

    $347,7375 Days on yellowkey   MLS ID: O6397026

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale O6397026 - 1459 OAK LEAF LN, KISSIMMEE, FL 34744 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1242
       Built: 1979   Tax: $4,859 (2025)
    Community: Heather Oaks Unit 4
    Single Family


    Estimated Monthly Payment: $2,310 (change assumption)
    Mortgage ($1,905) + Taxes in 2025 ($405)


    Taxes:$4,859

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 429 JANICE KAY PL, KISSIMMEE, FL 34744

    $450,00036 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)




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.