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Homes For Sale in Kissimmee 34744 - 360 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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  • 1502 JADEWOOD WAY, KISSIMMEE, FL 34744

    $350,000671 Days on yellowkey   MLS ID: O6233314

    0 Days Off yellowkey (back on 6/18/2026)

    SHORT SALE O6233314 - 1502 JADEWOOD WAY, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022
    Monthly Fee: $11
       Tax: $7,144 (2025)
    Community: Kindred Ph 2C & 2D Pb 30 Pgs 74-80 Lot 323
    Single Family


    Estimated Monthly Payment: $2,524 (change assumption)
    Mortgage ($1,918) + Fees ($11) + Taxes in 2025 ($595)


    Taxes:$7,144

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2345 SOUTHBURY, KISSIMMEE, FL 34744

    $369,0009 Days on yellowkey   MLS ID: S5151680

    For Sale S5151680 - 2345 SOUTHBURY, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.5   Gar: 4
    Liv Area Sq Ft: 1553
       Built: 2025
    Monthly Fee: $127
       Tax: $2,000 (2025)
    Community: Tohoqua Phase 1
    Townhouse


    Estimated Monthly Payment: $2,316 (change assumption)
    Mortgage ($2,022) + Fees ($127) + Taxes in 2025 ($167)


    Taxes:$2,000

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1380 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $649,900639 Days on yellowkey   MLS ID: S5112666

    REDUCED by $20,000 (3.0%) on 06/20/2026

    For Sale S5112666 - 1380 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 99 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3637
       Built: 2006   Tax: $4,833 (2023)
    Community: East Lake Shores
    Single Family


    Estimated Monthly Payment: $3,964 (change assumption)
    Mortgage ($3,561) + Taxes in 2023 ($403)


    Taxes:$4,833

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 1890 HICKORY BLUFF RD, KISSIMMEE, FL 34744

    $398,5004 Days on yellowkey   MLS ID: S5151971

    1 Days Off yellowkey (back on 6/20/2026)

    For Sale S5151971 - 1890 HICKORY BLUFF RD, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2018
    Monthly Fee: $10
       Tax: $8,279 (2025)
    Community: Kindred
    Single Family


    Estimated Monthly Payment: $2,883 (change assumption)
    Mortgage ($2,184) + Fees ($10) + Taxes in 2025 ($690)


    Taxes:$8,279

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2905 SUMMER GREEN TRL, KISSIMMEE, FL 34744

    $456,50018 Days on yellowkey   MLS ID: O6413243

    REDUCED by $13,400 (2.9%) on 06/19/2026

    For Sale O6413243 - 2905 SUMMER GREEN TRL, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2344
       Built: 2021
    Monthly Fee: $93
       Tax: $4,418 (2025)
    Community: Marbella Ph 2
    Single Family


    Estimated Monthly Payment: $2,962 (change assumption)
    Mortgage ($2,501) + Fees ($93) + Taxes in 2025 ($368)


    Taxes:$4,418

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $239,00010 Days on yellowkey   MLS ID: S5150953

    1 Days Off yellowkey (back on 6/19/2026)

    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)


  • 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744

    $499,900214 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)


  • 1610 MOHEGAN BLVD, KISSIMMEE, FL 34744

    $355,90038 Days on yellowkey   MLS ID: O6408062

    REDUCED by $4,000 (1.1%) on 06/19/2026

    For Sale O6408062 - 1610 MOHEGAN BLVD, KISSIMMEE, FL 34744 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2167
       Built: 2014
    Monthly Fee: $164
       Tax: $4,753 (2025)
    Community: Heritage Run
    Townhouse


    Estimated Monthly Payment: $2,510 (change assumption)
    Mortgage ($1,950) + Fees ($164) + Taxes in 2025 ($396)


    Taxes:$4,753

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744

    $650,00086 Days on yellowkey   MLS ID: O6393234

    REDUCED by $25,000 (3.7%) on 05/11/2026

    For Sale O6393234 - 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744 47 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3267
       Built: 2014
    Monthly Fee: $111
       Tax: $4,883 (2025)
    Community: North Point Ph Ic
    Single Family


    Estimated Monthly Payment: $4,079 (change assumption)
    Mortgage ($3,562) + Fees ($111) + Taxes in 2025 ($407)


    Taxes:$4,883

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2747 CALLAWAY LN, KISSIMMEE, FL 34744

    $385,00023 Days on yellowkey   MLS ID: O6411888

    REDUCED by $15,000 (3.8%) on 06/19/2026

    For Sale O6411888 - 2747 CALLAWAY LN, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1639
       Built: 2005
    Monthly Fee: $78
       Tax: $3,420 (2025)
    Community: Remington Prcl M1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,473 (change assumption)
    Mortgage ($2,110) + Fees ($78) + Taxes in 2025 ($285)


    Taxes:$3,420

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 3058 BAY LAUREL CIR N, KISSIMMEE, FL 34744

    $394,0008 Days on yellowkey   MLS ID: S5151672

    For Sale S5151672 - 3058 BAY LAUREL CIR N, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2059
       Built: 2002
    Monthly Fee: $132
       Tax: $3,608 (2025)
    Community: Springlake Village Ph 2B
    Single Family


    Estimated Monthly Payment: $2,592 (change assumption)
    Mortgage ($2,159) + Fees ($132) + Taxes in 2025 ($301)


    Taxes:$3,608

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 3824 BLUE DASHER DR, KISSIMMEE, FL 34744

    $499,990384 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

    $649,900109 Days on yellowkey   MLS ID: O6386876

    0 Days Off yellowkey (back on 6/19/2026)

    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)


  • 2050 E IRLO BRONSON MEMORIAL HWY #108, KISSIMMEE, FL 34744

    $33,000192 Days on yellowkey   MLS ID: O6366840

    REDUCED by $16,000 (32.7%) on 06/19/2026

    For Sale O6366840 - 2050 E IRLO BRONSON MEMORIAL HWY #108, KISSIMMEE, FL 34744 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 324
       Built: 1973
    Monthly Fee: $500
       Tax: $846 (2025)
    Community: Heritage Park In
    Condo


    Estimated Monthly Payment: $751 (change assumption)
    Mortgage ($181) + Fees ($500) + Taxes in 2025 ($71)


    Taxes:$846

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola County School for Arts

    Tax Year: 2025

    Middle School: Denn John Middle


  • 202 WOODSON CT, KISSIMMEE, FL 34744

    $623,00013 Days on yellowkey   MLS ID: O6414003

    For Sale O6414003 - 202 WOODSON CT, KISSIMMEE, FL 34744 72 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3744
       Built: 2000
    Monthly Fee: $92
       Tax: $4,485 (2025)
    Community: Remington Ph 01 Tr C
    Single Family


    Estimated Monthly Payment: $3,879 (change assumption)
    Mortgage ($3,414) + Fees ($92) + Taxes in 2025 ($374)


    Taxes:$4,485

    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

    $500,000104 Days on yellowkey   MLS ID: S5144389

    REDUCED by $15,000 (2.9%) on 06/05/2026

    For Sale S5144389 - 2963 SERA BELLA WAY, KISSIMMEE, FL 34744 68 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: $3,282 (change assumption)
    Mortgage ($2,740) + 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


  • 145 THORNBURY DR, KISSIMMEE, FL 34744

    $379,9003 Days on yellowkey   MLS ID: S5152081

    For Sale S5152081 - 145 THORNBURY DR, KISSIMMEE, FL 34744 3 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 2002
    Monthly Fee: $14
       Tax: $4,226 (2025)
    Community: Remington Prcl H Ph 2
    Single Family


    Estimated Monthly Payment: $2,448 (change assumption)
    Mortgage ($2,082) + Fees ($14) + Taxes in 2025 ($352)


    Taxes:$4,226

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1782 HIDEOUT ST, KISSIMMEE, FL 34744

    $454,9993 Days on yellowkey   MLS ID: S5152167

    For Sale S5152167 - 1782 HIDEOUT ST, KISSIMMEE, FL 34744 17 photos

    Bed: 4   Bath: 2.0   Gar: 4
    Liv Area Sq Ft: 1846
       Built: 2024
    Monthly Fee: $11
       Tax: $7,778 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $3,152 (change assumption)
    Mortgage ($2,493) + Fees ($11) + Taxes in 2025 ($648)


    Taxes:$7,778

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2000 RANKIN ST, KISSIMMEE, FL 34744

    $319,0003 Days on yellowkey   MLS ID: S5151625

    SHORT SALE S5151625 - 2000 RANKIN ST, KISSIMMEE, FL 34744 6 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1814
       Built: 2024
    Monthly Fee: $89
       Tax: $5,659 (2025)
    Community: Kindred Ph 3A
    Townhouse


    Estimated Monthly Payment: $2,308 (change assumption)
    Mortgage ($1,748) + Fees ($89) + Taxes in 2025 ($472)


    Taxes:$5,659

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1556 HEATHER WAY, KISSIMMEE, FL 34744

    $320,00051 Days on yellowkey   MLS ID: O6404040

    REDUCED by $20,000 (5.9%) on 05/30/2026

    For Sale O6404040 - 1556 HEATHER WAY, KISSIMMEE, FL 34744 5 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1577
       Built: 1976   Tax: $3,121 (2025)
    Community: Heather Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,013 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($260)


    Taxes:$3,121

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle




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.