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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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  • 237 STRATHMORE CIR, KISSIMMEE, FL 34744

    $424,90071 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


  • 1941 PARTIN TERRACE RD, KISSIMMEE, FL 34744

    $514,400137 Days on yellowkey   MLS ID: O6386096

    REDUCED by $5,000 (1.0%) on 07/09/2026

    For Sale O6386096 - 1941 PARTIN TERRACE RD, KISSIMMEE, FL 34744 37 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2787
       Built: 2019
    Monthly Fee: $11
       Tax: $3,624 (2025)
    Community: Kindred 100 Rep
    Single Family


    Estimated Monthly Payment: $3,132 (change assumption)
    Mortgage ($2,819) + Fees ($11) + Taxes in 2025 ($302)


    Taxes:$3,624

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1115 PROSPERITY AVE, KISSIMMEE, FL 34744

    $469,000116 Days on yellowkey   MLS ID: S5146235

    REDUCED by $5,000 (1.1%) on 06/29/2026

    For Sale S5146235 - 1115 PROSPERITY AVE, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2085
       Built: 2003
    Monthly Fee: $46
       Tax: $2,454 (2025)
    Community: Fortune Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,820 (change assumption)
    Mortgage ($2,570) + Fees ($46) + Taxes in 2025 ($205)


    Taxes:$2,454

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1989 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $400,000180 Days on yellowkey   MLS ID: O6371277

    REDUCED by $15,000 (3.6%) on 07/09/2026

    For Sale O6371277 - 1989 SPRING SHOWER CIR, KISSIMMEE, FL 34744 63 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2087
       Built: 2023
    Monthly Fee: $136
       Tax: $7,473 (2025)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $2,950 (change assumption)
    Mortgage ($2,192) + Fees ($136) + Taxes in 2025 ($623)


    Taxes:$7,473

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1810 N BRACK ST, KISSIMMEE, FL 34744

    $250,0008 Days on yellowkey   MLS ID: O6422750

    For Sale O6422750 - 1810 N BRACK ST, KISSIMMEE, FL 34744 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 816
       Built: 1962   Tax: $1,589 (2024)
    Community: Robert Bass Add
    Single Family


    Estimated Monthly Payment: $1,502 (change assumption)
    Mortgage ($1,370) + Taxes in 2024 ($132)


    Taxes:$1,589

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 1869 KINGS POINT BLVD, KISSIMMEE, FL 34744

    $410,0004 Days on yellowkey   MLS ID: O6424293

    For Sale O6424293 - 1869 KINGS POINT BLVD, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1704
       Built: 1983   Tax: $2,073 (2025)
    Community: Kings Point
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,419 (change assumption)
    Mortgage ($2,247) + Taxes in 2025 ($173)


    Taxes:$2,073

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 192 WESTMORELAND CIR, KISSIMMEE, FL 34744

    $430,0004 Days on yellowkey   MLS ID: S5153506

    0 Days Off yellowkey (back on 7/10/2026)

    For Sale S5153506 - 192 WESTMORELAND CIR, KISSIMMEE, FL 34744 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2285
       Built: 1997
    Monthly Fee: $14
       Tax: $3,379 (2025)
    Community: Remington Ph 1 Tr F
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,356) + Fees ($14) + Taxes in 2025 ($282)


    Taxes:$3,379

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 28 LINDA LN, KISSIMMEE, FL 34744

    $470,0004 Days on yellowkey   MLS ID: O6422948

    For Sale O6422948 - 28 LINDA LN, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1745
       Built: 1973   Tax: $4,300 (2025)
    Community: Cadillac Homes
    Single Family


    Estimated Monthly Payment: $2,934 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($358)


    Taxes:$4,300

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2994 BIG SKY BLVD, KISSIMMEE, FL 34744

    $450,0004 Days on yellowkey   MLS ID: S5153486

    For Sale S5153486 - 2994 BIG SKY BLVD, KISSIMMEE, FL 34744 34 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2700
       Built: 1982   Tax: $4,341 (2025)
    Community: Acreage & Unrec
    Single Family


    Estimated Monthly Payment: $2,827 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($362)


    Taxes:$4,341

    Elementary School: East Lake Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 988 PINEWOOD ST, KISSIMMEE, FL 34744

    $343,9904 Days on yellowkey   MLS ID: O6424143

    For Sale O6424143 - 988 PINEWOOD ST, KISSIMMEE, FL 34744 15 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1489
       Built: 2025
    Monthly Fee: $86
       Tax: $2,304 (2025)
    Community: Fish Lake Cove
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,163 (change assumption)
    Mortgage ($1,885) + Fees ($86) + Taxes in 2025 ($192)


    Taxes:$2,304

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2275 SOUTHBURY DR, KISSIMMEE, FL 34744

    $346,790134 Days on yellowkey   MLS ID: O6386802

    4 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $2,000 (0.6%) on 06/08/2026

    For Sale O6386802 - 2275 SOUTHBURY DR, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1553
       Built: 2026
    Monthly Fee: $130
       Tax: $1,610 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,164 (change assumption)
    Mortgage ($1,900) + Fees ($130) + Taxes in 2025 ($134)


    Taxes:$1,610

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1895 HICKORY BLUFF RD, KISSIMMEE, FL 34744

    $349,900175 Days on yellowkey   MLS ID: S5142089

    3 Days Off yellowkey (back on 6/16/2026)

    For Sale S5142089 - 1895 HICKORY BLUFF RD, KISSIMMEE, FL 34744 17 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 2017
    Monthly Fee: $11
       Tax: $6,019 (2025)
    Community: Kindred Ph 1C Pb 25 Pgs 127-134 Lot 373
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,430 (change assumption)
    Mortgage ($1,917) + Fees ($11) + Taxes in 2025 ($502)


    Taxes:$6,019

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1959 SUMMER SERENITY DR, KISSIMMEE, FL 34744

    $390,00025 Days on yellowkey   MLS ID: S5151902

    For Sale S5151902 - 1959 SUMMER SERENITY DR, KISSIMMEE, FL 34744 34 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2072
       Built: 2023
    Monthly Fee: $7
       Tax: $6,594 (2025)
    Community: Tohoqua Ph 4B
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,693 (change assumption)
    Mortgage ($2,137) + Fees ($7) + Taxes in 2025 ($550)


    Taxes:$6,594

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1610 MOHEGAN BLVD, KISSIMMEE, FL 34744

    $339,90061 Days on yellowkey   MLS ID: O6408062

    REDUCED by $16,000 (4.5%) on 07/10/2026

    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: $2,422 (change assumption)
    Mortgage ($1,862) + Fees ($164) + Taxes in 2025 ($396)


    Taxes:$4,753

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2540 WINNERS CIR, KISSIMMEE, FL 34744

    $650,000145 Days on yellowkey   MLS ID: O6382446

    0 Days Off yellowkey (back on 7/6/2026)

    REDUCED by $39,000 (5.7%) on 07/03/2026

    For Sale O6382446 - 2540 WINNERS CIR, KISSIMMEE, FL 34744 52 photos

    Bed: 4   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 3246
       Built: 2000   Tax: $3,688 (2025)
    Community: Winners Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,869 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($307)


    Taxes:$3,688

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1757 QUAIL RIDGE LOOP, KISSIMMEE, FL 34744

    $344,999106 Days on yellowkey   MLS ID: O6391222

    For Sale O6391222 - 1757 QUAIL RIDGE LOOP, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1109
       Built: 1992   Tax: $4,829 (2025)
    Community: Quail Hollow Ph 1
    Single Family


    Estimated Monthly Payment: $2,293 (change assumption)
    Mortgage ($1,890) + Taxes in 2025 ($402)


    Taxes:$4,829

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 930 SHORE DR, KISSIMMEE, FL 34744

    $598,50056 Days on yellowkey   MLS ID: TB8510529

    REDUCED by $16,500 (2.7%) on 07/10/2026

    For Sale TB8510529 - 930 SHORE DR, KISSIMMEE, FL 34744 25 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: $3,557 (change assumption)
    Mortgage ($3,279) + Taxes in 2025 ($277)


    Taxes:$3,326

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2780 VICKIE CT, KISSIMMEE, FL 34744

    $3,499,000171 Days on yellowkey   MLS ID: O6376322

    For Sale O6376322 - 2780 VICKIE CT, KISSIMMEE, FL 34744 94 photos

    Bed: 10   Bath: 7.5   Gar: 4
    Liv Area Sq Ft: 9881
       Built: 2008   Tax: $15,347 (2025)
    Community: Florida Fruit Belt Sales Co 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $20,451 (change assumption)
    Mortgage ($19,172) + Taxes in 2025 ($1,279)


    Taxes:$15,347

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 4405 BISCAYNE BREEZE WAY, KISSIMMEE, FL 34744

    $460,00094 Days on yellowkey   MLS ID: O6398072

    4 Days Off yellowkey (back on 7/10/2026)

    REDUCED by $15,000 (3.2%) on 06/04/2026

    For Sale O6398072 - 4405 BISCAYNE BREEZE WAY, KISSIMMEE, FL 34744 24 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2601
       Built: 2011
    Monthly Fee: $111
       Tax: $4,260 (2025)
    Community: North Point Ph 1A
    Single Family


    Estimated Monthly Payment: $2,986 (change assumption)
    Mortgage ($2,520) + Fees ($111) + Taxes in 2025 ($355)


    Taxes:$4,260

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 700 ADRIANE PARK CIR, KISSIMMEE, FL 34744

    $589,90027 Days on yellowkey   MLS ID: S5152087

    0 Days Off yellowkey (back on 7/10/2026)

    For Sale S5152087 - 700 ADRIANE PARK CIR, KISSIMMEE, FL 34744 45 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2948
       Built: 1992
    Monthly Fee: $37
       Tax: $6,962 (2025)
    Community: Adriane Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,849 (change assumption)
    Mortgage ($3,232) + Fees ($37) + Taxes in 2025 ($580)


    Taxes:$6,962

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    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.