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Homes For Sale in Kissimmee 34744 - 343 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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  • 2705 PRESTWICK LN, KISSIMMEE, FL 34744

    $410,00094 Days on yellowkey   MLS ID: O6384546

    For Sale O6384546 - 2705 PRESTWICK LN, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1719
       Built: 2005
    Monthly Fee: $73
       Tax: $6,174 (2025)
    Community: Remington Prcl M1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,834 (change assumption)
    Mortgage ($2,247) + Fees ($73) + Taxes in 2025 ($515)


    Taxes:$6,174

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744

    $650,00063 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


  • 1956 EGRET MEADOWS AVE, KISSIMMEE, FL 34744

    $394,9908 Days on yellowkey   MLS ID: O6409425

    For Sale O6409425 - 1956 EGRET MEADOWS AVE, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1516
       Built: 2020
    Monthly Fee: $11
       Tax: $6,661 (2025)
    Community: Kindred Ph 2A
    Single Family


    Estimated Monthly Payment: $2,730 (change assumption)
    Mortgage ($2,164) + Fees ($11) + Taxes in 2025 ($555)


    Taxes:$6,661

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1550 REGAL OAK DR, KISSIMMEE, FL 34744

    $480,00014 Days on yellowkey   MLS ID: S5150034

    For Sale S5150034 - 1550 REGAL OAK DR, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2312
       Built: 1983   Tax: $3,426 (2025)
    Community: Regal Oak Shores Unit 4
    Single Family


    Estimated Monthly Payment: $2,916 (change assumption)
    Mortgage ($2,630) + Taxes in 2025 ($286)


    Taxes:$3,426

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744

    $515,00046 Days on yellowkey   MLS ID: S5147642

    REDUCED by $15,000 (2.8%) on 05/20/2026

    For Sale S5147642 - 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744 41 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2930
       Built: 1996
    Monthly Fee: $13
       Tax: $6,439 (2025)
    Community: Remington Ph 1 Tr E
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,371 (change assumption)
    Mortgage ($2,822) + Fees ($13) + Taxes in 2025 ($537)


    Taxes:$6,439

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1737 KATO WAY, KISSIMMEE, FL 34744

    $345,00058 Days on yellowkey   MLS ID: TB8492414

    REDUCED by $10,000 (2.8%) on 05/19/2026

    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: $2,394 (change assumption)
    Mortgage ($1,890) + 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


  • 1892 BRIGHT SKY DR, KISSIMMEE, FL 34744

    $468,000106 Days on yellowkey   MLS ID: S5143785

    For Sale S5143785 - 1892 BRIGHT SKY DR, KISSIMMEE, FL 34744 12 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2522
       Built: 2025
    Monthly Fee: $7
       Tax: $2,686 (2025)
    Community: Tohoqua Ph 7
    Single Family


    Estimated Monthly Payment: $2,795 (change assumption)
    Mortgage ($2,564) + Fees ($7) + Taxes in 2025 ($224)


    Taxes:$2,686

    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

    $515,000191 Days on yellowkey   MLS ID: S5138827

    REDUCED by $10,000 (1.9%) on 04/22/2026

    For Sale S5138827 - 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744 63 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: $3,329 (change assumption)
    Mortgage ($2,822) + 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)


  • 1666 MARINA LAKE DR, KISSIMMEE, FL 34744

    $899,99029 Days on yellowkey   MLS ID: O6401678

    REDUCED by $75,010 (7.7%) on 05/21/2026

    For Sale O6401678 - 1666 MARINA LAKE DR, KISSIMMEE, FL 34744 48 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3721
       Built: 2000
    Monthly Fee: $75
       Tax: $9,365 (2025)
    Community: Ashley Cove Unit 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,787 (change assumption)
    Mortgage ($4,931) + Fees ($75) + Taxes in 2025 ($780)


    Taxes:$9,365

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1828 PARTIN TERRACE RD, KISSIMMEE, FL 34744

    $414,900114 Days on yellowkey   MLS ID: S5143083

    For Sale S5143083 - 1828 PARTIN TERRACE RD, KISSIMMEE, FL 34744 47 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2017
    Monthly Fee: $10
       Tax: $8,257 (2025)
    Community: Kindred Ph 1C
    Single Family


    Estimated Monthly Payment: $2,971 (change assumption)
    Mortgage ($2,273) + Fees ($10) + Taxes in 2025 ($688)


    Taxes:$8,257

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1740 SAINT TROPEZ CT, KISSIMMEE, FL 34744

    $335,0009 Days on yellowkey   MLS ID: O6409575

    For Sale O6409575 - 1740 SAINT TROPEZ CT, KISSIMMEE, FL 34744 32 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2104
       Built: 1991
    Monthly Fee: $150
       Tax: $2,753 (2025)
    Community: Monaco Villas Ph 2
    Townhouse


    Estimated Monthly Payment: $2,215 (change assumption)
    Mortgage ($1,836) + Fees ($150) + Taxes in 2025 ($229)


    Taxes:$2,753

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $450,00092 Days on yellowkey   MLS ID: S5144261

    REDUCED by $7,000 (1.5%) on 04/30/2026

    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: $2,862 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($396)


    Taxes:$4,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3215 STRATTON CIR, KISSIMMEE, FL 34744

    $460,0007 Days on yellowkey   MLS ID: S5150428

    For Sale S5150428 - 3215 STRATTON CIR, KISSIMMEE, FL 34744 23 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2432
       Built: 2018
    Monthly Fee: $80
       Tax: $4,244 (2025)
    Community: South Pointe
    Single Family


    Estimated Monthly Payment: $2,954 (change assumption)
    Mortgage ($2,520) + Fees ($80) + Taxes in 2025 ($354)


    Taxes:$4,244

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1756 STAMEN DR, KISSIMMEE, FL 34744

    $399,000100 Days on yellowkey   MLS ID: TB8475839

    0 Days Off yellowkey (back on 5/7/2026)

    REDUCED by $50,900 (11.3%) on 05/05/2026

    SHORT SALE TB8475839 - 1756 STAMEN DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2272
       Built: 2023
    Monthly Fee: $160
       Tax: $6,118 (2025)
    Community: Pennyroyal
    Single Family


    Estimated Monthly Payment: $2,856 (change assumption)
    Mortgage ($2,186) + Fees ($160) + Taxes in 2025 ($510)


    Taxes:$6,118

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1890 SAHA CT, KISSIMMEE, FL 34744

    $2,500,0007 Days on yellowkey   MLS ID: O6410092

    For Sale O6410092 - 1890 SAHA CT, KISSIMMEE, FL 34744 32 photos

    Bed: 7   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 7247
       Built: 1978   Tax: $14,882 (2025)
    Community: Regal Oak Shores Unit 3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,938 (change assumption)
    Mortgage ($13,698) + Taxes in 2025 ($1,240)


    Taxes:$14,882

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1150 STROUPE RD, KISSIMMEE, FL 34744

    $450,00013 Days on yellowkey   MLS ID: S5149769

    1 Days Off yellowkey (back on 5/22/2026)

    For Sale S5149769 - 1150 STROUPE RD, KISSIMMEE, FL 34744 65 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2128
       Built: 1973   Tax: $2,257 (2025)
    Community: Midway City Townsite
    Single Family


    Estimated Monthly Payment: $2,654 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($188)


    Taxes:$2,257

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1769 LEE JANZEN DR, KISSIMMEE, FL 34744

    $649,90014 Days on yellowkey   MLS ID: S5149658

    0 Days Off yellowkey (back on 5/22/2026)

    For Sale S5149658 - 1769 LEE JANZEN DR, KISSIMMEE, FL 34744 47 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2834
       Built: 1999
    Monthly Fee: $195
       Tax: $5,365 (2025)
    Community: Kissimmee Bay
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,203 (change assumption)
    Mortgage ($3,561) + Fees ($195) + Taxes in 2025 ($447)


    Taxes:$5,365

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2542 CAMPHORWOOD CIR, KISSIMMEE, FL 34744

    $359,900225 Days on yellowkey   MLS ID: S5136753

    For Sale S5136753 - 2542 CAMPHORWOOD CIR, KISSIMMEE, FL 34744 12 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1406
       Built: 1987   Tax: $846 (2024)
    Community: Oak Hollow Ph 3
    Single Family


    Estimated Monthly Payment: $2,043 (change assumption)
    Mortgage ($1,972) + Taxes in 2024 ($71)


    Taxes:$846

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 1980 SUMMER CT, KISSIMMEE, FL 34744

    $529,00065 Days on yellowkey   MLS ID: O6392643

    REDUCED by $6,000 (1.1%) on 05/22/2026

    For Sale O6392643 - 1980 SUMMER CT, KISSIMMEE, FL 34744 38 photos

    Bed: 3   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 2687
       Built: 2005   Tax: $6,583 (2025)
    Community: Meadow Spgs
    Single Family


    Estimated Monthly Payment: $3,447 (change assumption)
    Mortgage ($2,899) + Taxes in 2025 ($549)


    Taxes:$6,583

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2601 GOLD DUST CIR, KISSIMMEE, FL 34744

    $485,00064 Days on yellowkey   MLS ID: S5146084

    REDUCED by $10,000 (2.0%) on 05/09/2026

    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: $3,049 (change assumption)
    Mortgage ($2,657) + 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.