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Homes For Sale in Kissimmee 34744 - 257 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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  • 2394 OLD DIXIE HWY, KISSIMMEE, FL 34744

    $289,99927 Days on yellowkey   MLS ID: O6366826

    0 Days Off yellowkey (back on 3/12/2026)

    For Sale O6366826 - 2394 OLD DIXIE HWY, KISSIMMEE, FL 34744 3 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1567
       Built: 1958   Tax: $3,253 (2024)
    Community: Colonial Estates
    Single Family


    Estimated Monthly Payment: $1,860 (change assumption)
    Mortgage ($1,589) + Taxes in 2024 ($271)


    Taxes:$3,253

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 229 STRATHMORE CIR, KISSIMMEE, FL 34744

    $489,900117 Days on yellowkey   MLS ID: O6367119

    REDUCED by $10,000 (2.0%) on 04/08/2026

    For Sale O6367119 - 229 STRATHMORE CIR, KISSIMMEE, FL 34744 74 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2606
       Built: 1996
    Monthly Fee: $14
       Tax: $4,408 (2024)
    Community: Remington Ph 1 Tr B
    Single Family


    Estimated Monthly Payment: $3,066 (change assumption)
    Mortgage ($2,684) + Fees ($14) + Taxes in 2024 ($367)


    Taxes:$4,408

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2035 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $424,39083 Days on yellowkey   MLS ID: O6374311

    REDUCED by $26,150 (5.8%) on 04/08/2026

    For Sale O6374311 - 2035 SPRING SHOWER CIR, KISSIMMEE, FL 34744 23 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2018
       Built: 2026
    Monthly Fee: $128
       Tax: $3,007 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,704 (change assumption)
    Mortgage ($2,325) + Fees ($128) + Taxes in 2025 ($251)


    Taxes:$3,007

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4436 AZURE ISLE WAY, KISSIMMEE, FL 34744

    $499,00062 Days on yellowkey   MLS ID: O6379702

    For Sale O6379702 - 4436 AZURE ISLE WAY, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2251
       Built: 2013
    Monthly Fee: $108
       Tax: $3,771 (2025)
    Community: North Point Ph 1B
    Single Family


    Estimated Monthly Payment: $3,156 (change assumption)
    Mortgage ($2,734) + Fees ($108) + Taxes in 2025 ($314)


    Taxes:$3,771

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2705 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $390,00071 Days on yellowkey   MLS ID: G5107373

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale G5107373 - 2705 WILLOW GLEN CIR, KISSIMMEE, FL 34744 14 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1679
       Built: 2001
    Monthly Fee: $19
       Tax: $6,110 (2025)
    Community: Gleneagles
    Single Family


    Estimated Monthly Payment: $2,665 (change assumption)
    Mortgage ($2,137) + Fees ($19) + Taxes in 2025 ($509)


    Taxes:$6,110

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1503 OAK RESERVE DR, KISSIMMEE, FL 34744

    $445,00048 Days on yellowkey   MLS ID: S5144250

    REDUCED by $5,000 (1.1%) on 04/08/2026

    For Sale S5144250 - 1503 OAK RESERVE DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022   Tax: $7,738 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,083 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($645)


    Taxes:$7,738

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: St. Cloud Middle (6-8)


  • 305 POINCIANA CIR, KISSIMMEE, FL 34744

    $360,00072 Days on yellowkey   MLS ID: S5142338

    0 Days Off yellowkey (back on 1/26/2026)

    For Sale S5142338 - 305 POINCIANA CIR, KISSIMMEE, FL 34744 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1361
       Built: 1955   Tax: $521 (2025)
    Community: Dellwood Park
    Single Family


    Estimated Monthly Payment: $2,016 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($43)


    Taxes:$521

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2571 AMES HAVEN RD, KISSIMMEE, FL 34744

    $749,900292 Days on yellowkey   MLS ID: S5129375

    4 Days Off yellowkey (back on 2/18/2026)

    For Sale S5129375 - 2571 AMES HAVEN RD, KISSIMMEE, FL 34744 86 photos

    Bed: 4   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 2556
       Built: 1920   Tax: $4,045 (2024)
    Community: None
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,446 (change assumption)
    Mortgage ($4,109) + Taxes in 2024 ($337)


    Taxes:$4,045

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15 ADAMS AVE, KISSIMMEE, FL 34744

    $440,000169 Days on yellowkey   MLS ID: OM711923

    For Sale OM711923 - 15 ADAMS AVE, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1682
       Built: 1972   Tax: $2,767 (2024)
    Community: Idora Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,642 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($231)


    Taxes:$2,767

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2661 AMES HAVEN RD, KISSIMMEE, FL 34744

    $439,00035 Days on yellowkey   MLS ID: S5145125

    REDUCED by $6,000 (1.3%) on 03/31/2026

    For Sale S5145125 - 2661 AMES HAVEN RD, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1666
       Built: 1984   Tax: $4,502 (2025)
    Community: Emerald Lake Colony Unit 1
    Single Family


    Estimated Monthly Payment: $2,781 (change assumption)
    Mortgage ($2,405) + Taxes in 2025 ($375)


    Taxes:$4,502

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2670 REAGAN LN, KISSIMMEE, FL 34744

    $370,00041 Days on yellowkey   MLS ID: O6385604

    For Sale O6385604 - 2670 REAGAN LN, KISSIMMEE, FL 34744 65 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1294
       Built: 1981   Tax: $1,125 (2025)
    Community: Gehrett Gardens
    Single Family


    Estimated Monthly Payment: $2,121 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($94)


    Taxes:$1,125

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2352 ROSS ST, KISSIMMEE, FL 34744

    $315,000293 Days on yellowkey   MLS ID: O6320029

    For Sale O6320029 - 2352 ROSS ST, KISSIMMEE, FL 34744 5 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1330
       Built: 2025   Tax: $608 (2024)
    Community: Gilchrist Add To Kissimmee
    Single Family


    Estimated Monthly Payment: $1,777 (change assumption)
    Mortgage ($1,726) + Taxes in 2024 ($51)


    Taxes:$608

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 627 WOODLAND CREEK BLVD, KISSIMMEE, FL 34744

    $459,90020 Days on yellowkey   MLS ID: O6392189

    REDUCED by $10,000 (2.1%) on 04/08/2026

    For Sale O6392189 - 627 WOODLAND CREEK BLVD, KISSIMMEE, FL 34744 47 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2846
       Built: 2005
    Monthly Fee: $41
       Tax: $3,538 (2025)
    Community: Woodland Creek
    Single Family


    Estimated Monthly Payment: $2,856 (change assumption)
    Mortgage ($2,520) + Fees ($41) + Taxes in 2025 ($295)


    Taxes:$3,538

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 106 BURRELL CIR, KISSIMMEE, FL 34744

    $525,00026 Days on yellowkey   MLS ID: S5145477

    For Sale S5145477 - 106 BURRELL CIR, KISSIMMEE, FL 34744 49 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3173
       Built: 1999
    Monthly Fee: $14
       Tax: $8,142 (2025)
    Community: Remington Ph 1 Tr C
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,569 (change assumption)
    Mortgage ($2,877) + Fees ($14) + Taxes in 2025 ($679)


    Taxes:$8,142

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2921 PUERTA DEL SOL BLVD, KISSIMMEE, FL 34744

    $257,800384 Days on yellowkey   MLS ID: S5123068

    REDUCED by $9,199 (3.4%) on 04/08/2026

    For Sale S5123068 - 2921 PUERTA DEL SOL BLVD, KISSIMMEE, FL 34744 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1274
       Built: 2014
    Monthly Fee: $362
       Tax: $5,527 (2024)
    Community: Villa Sol
    Townhouse


    Estimated Monthly Payment: $2,235 (change assumption)
    Mortgage ($1,413) + Fees ($362) + Taxes in 2024 ($461)


    Taxes:$5,527

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744

    $560,00014 Days on yellowkey   MLS ID: O6390966

    For Sale O6390966 - 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744 77 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: $3,668 (change assumption)
    Mortgage ($3,068) + Fees ($11) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744

    $675,00012 Days on yellowkey   MLS ID: O6393234

    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: $4,216 (change assumption)
    Mortgage ($3,699) + Fees ($111) + Taxes in 2025 ($407)


    Taxes:$4,883

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2716 WORTHAM LN, KISSIMMEE, FL 34744

    $417,50040 Days on yellowkey   MLS ID: O6385986

    REDUCED by $2,500 (0.6%) on 04/08/2026

    For Sale O6385986 - 2716 WORTHAM LN, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2341
       Built: 1998
    Monthly Fee: $13
       Tax: $6,364 (2025)
    Community: Remington Ph 1 Tr E
    Single Family


    Estimated Monthly Payment: $2,831 (change assumption)
    Mortgage ($2,288) + Fees ($13) + Taxes in 2025 ($530)


    Taxes:$6,364

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 429 JANICE KAY PL, KISSIMMEE, FL 34744

    $450,00030 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)


  • 2601 GOLD DUST CIR, KISSIMMEE, FL 34744

    $495,00013 Days on yellowkey   MLS ID: S5146084

    REDUCED by $15,000 (2.9%) on 04/08/2026

    For Sale S5146084 - 2601 GOLD DUST CIR, KISSIMMEE, FL 34744 23 photos

    Bed: 4   Bath: 3.5   Gar: 18
    Liv Area Sq Ft: 2691
       Built: 2001
    Monthly Fee: $47
       Tax: $4,131 (2025)
    Community: Fortune Lakes
    Single Family


    Estimated Monthly Payment: $3,104 (change assumption)
    Mortgage ($2,712) + Fees ($47) + Taxes in 2025 ($344)


    Taxes:$4,131

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    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.