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Kissimmee Villas For Sale - 47 villas

Kissimmee villas for sale are located in Osceola County, Florida. Find villas in Kissimmee for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Kissimmee villas.

Location: Kissimmee

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  • 1691 KEY BAY TRL, KISSIMMEE, FL 34747

    $355,00013 Days on yellowkey   MLS ID: S5149880

    For Sale S5149880 - 1691 KEY BAY TRL, KISSIMMEE, FL 34747 14 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1557
       Built: 2021
    Monthly Fee: $480
       Tax: $8,793 (2025)
    Community: Four Seasons At Orlando Ph 3B
    Villa


    Estimated Monthly Payment: $3,158 (change assumption)
    Mortgage ($1,945) + Fees ($480) + Taxes in 2025 ($733)


    Taxes:$8,793

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 40 E COUNTRY COVE WAY, KISSIMMEE, FL 34743

    $215,000126 Days on yellowkey   MLS ID: S5142234

    For Sale S5142234 - 40 E COUNTRY COVE WAY, KISSIMMEE, FL 34743 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 960
       Built: 1983
    Monthly Fee: $110
       Tax: $3,180 (2025)
    Community: Country Cove Villas
    Villa


    Estimated Monthly Payment: $1,553 (change assumption)
    Mortgage ($1,178) + Fees ($110) + Taxes in 2025 ($265)


    Taxes:$3,180

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1999 KEY BAY TRL, KISSIMMEE, FL 34747

    $419,00049 Days on yellowkey   MLS ID: O6396388

    REDUCED by $10,980 (2.6%) on 05/11/2026

    For Sale O6396388 - 1999 KEY BAY TRL, KISSIMMEE, FL 34747 35 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1557
       Built: 2023
    Monthly Fee: $480
       Tax: $6,794 (2025)
    Community: Four Seasons At Orlando Ph 4B
    Villa


    Estimated Monthly Payment: $3,342 (change assumption)
    Mortgage ($2,296) + Fees ($480) + Taxes in 2025 ($566)


    Taxes:$6,794

    Elementary School: Island Village Elementary School

    High School: Poinciana High School

    Tax Year: 2025

    Middle School: Horizon Middle


  • 1998 KEY BAY TRL #524, KISSIMMEE, FL 34747

    $395,000134 Days on yellowkey   MLS ID: G5106590

    For Sale G5106590 - 1998 KEY BAY TRL #524, KISSIMMEE, FL 34747 48 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1583
       Built: 2022
    Monthly Fee: $480
       Tax: $7,954 (2025)
    Community: Four Seasons At Orlando Ph 4B
    Spa: No

    Villa


    Estimated Monthly Payment: $3,307 (change assumption)
    Mortgage ($2,164) + Fees ($480) + Taxes in 2025 ($663)


    Taxes:$7,954

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1621 CUMIN DR, KISSIMMEE, FL 34759

    $189,50086 Days on yellowkey   MLS ID: S5144944

    REDUCED by $7,000 (3.6%) on 05/13/2026

    For Sale S5144944 - 1621 CUMIN DR, KISSIMMEE, FL 34759 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1067
       Built: 2025
    Monthly Fee: $270
       Tax: $676 (2025)
    Community: Tuscany Preserve Ph 03
    Villa


    Estimated Monthly Payment: $1,365 (change assumption)
    Mortgage ($1,038) + Fees ($270) + Taxes in 2025 ($56)


    Taxes:$676

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4249 CURACAO PL, KISSIMMEE, FL 34758

    $271,540204 Days on yellowkey   MLS ID: O6358206

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

    INCREASED by $2,000 (0.7%) on 04/09/2026

    For Sale O6358206 - 4249 CURACAO PL, KISSIMMEE, FL 34758 30 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1562
       Built: 2025
    Monthly Fee: $465

    Community: Westview 27 Villas
    Villa


    Estimated Monthly Payment: $1,953 (change assumption)
    Mortgage ($1,488) + Fees ($465) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4254 ST THOMAS WAY, KISSIMMEE, FL 34758

    $270,540113 Days on yellowkey   MLS ID: O6379850

    0 Days Off yellowkey (back on 5/4/2026)

    REDUCED by $5,000 (1.8%) on 04/29/2026

    For Sale O6379850 - 4254 ST THOMAS WAY, KISSIMMEE, FL 34758 30 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1562
       Built: 2026
    Monthly Fee: $429

    Community: Westview 27 Villas
    Villa


    Estimated Monthly Payment: $1,911 (change assumption)
    Mortgage ($1,482) + Fees ($429) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4244 ST THOMAS WAY, KISSIMMEE, FL 34758

    $243,540132 Days on yellowkey   MLS ID: O6374376

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

    For Sale O6374376 - 4244 ST THOMAS WAY, KISSIMMEE, FL 34758 30 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1562
       Built: 2026
    Monthly Fee: $429

    Community: Westview 27 Villas
    Villa


    Estimated Monthly Payment: $1,763 (change assumption)
    Mortgage ($1,334) + Fees ($429) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4246 ST THOMAS WAY, KISSIMMEE, FL 34758

    $243,540132 Days on yellowkey   MLS ID: O6374377

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

    For Sale O6374377 - 4246 ST THOMAS WAY, KISSIMMEE, FL 34758 30 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1562
       Built: 2026
    Monthly Fee: $429

    Community: Westview 27 Villas
    Villa


    Estimated Monthly Payment: $1,763 (change assumption)
    Mortgage ($1,334) + Fees ($429) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1487 AXEL GRAESON AVE, KISSIMMEE, FL 34744

    $387,00028 Days on yellowkey   MLS ID: S5148628

    For Sale S5148628 - 1487 AXEL GRAESON AVE, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1509
       Built: 2024
    Monthly Fee: $280
       Tax: $4,534 (2025)
    Community: Seasons At Big Sky Ph 1
    Villa


    Estimated Monthly Payment: $2,778 (change assumption)
    Mortgage ($2,120) + Fees ($280) + Taxes in 2025 ($378)


    Taxes:$4,534

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 498 PRESTWICK PL, KISSIMMEE, FL 34759

    $149,00042 Days on yellowkey   MLS ID: O6399966

    1 Days Off yellowkey (back on 5/9/2026)

    For Sale O6399966 - 498 PRESTWICK PL, KISSIMMEE, FL 34759 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1104
       Built: 1987
    Monthly Fee: $400
       Tax: $519 (2025)
    Community: Golf Villas 02 At Poinciana Rep 01
    Villa


    Estimated Monthly Payment: $1,260 (change assumption)
    Mortgage ($816) + Fees ($400) + Taxes in 2025 ($43)


    Taxes:$519

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1822 CORIANDER DR, KISSIMMEE, FL 34759

    $225,00028 Days on yellowkey   MLS ID: O6403359

    For Sale O6403359 - 1822 CORIANDER DR, KISSIMMEE, FL 34759 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1056
       Built: 2026
    Monthly Fee: $198
       Tax: $330 (2025)
    Community: Tuscany Preserve Ph 03
    Villa


    Estimated Monthly Payment: $1,458 (change assumption)
    Mortgage ($1,233) + Fees ($198) + Taxes in 2025 ($28)


    Taxes:$330

    Elementary School: Laurel Elementary

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Lake Marion Creek Middle


  • 1826 CORIANDER DR, KISSIMMEE, FL 34759

    $225,00028 Days on yellowkey   MLS ID: O6403416

    For Sale O6403416 - 1826 CORIANDER DR, KISSIMMEE, FL 34759 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1056
       Built: 2026
    Monthly Fee: $198
       Tax: $330 (2025)
    Community: Tuscany Preserve Ph 03
    Villa


    Estimated Monthly Payment: $1,458 (change assumption)
    Mortgage ($1,233) + Fees ($198) + Taxes in 2025 ($28)


    Taxes:$330

    Elementary School: Laurel Elementary

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Lake Marion Creek Middle


  • 1824 CORIANDER DR, KISSIMMEE, FL 34759

    $215,00028 Days on yellowkey   MLS ID: O6403384

    For Sale O6403384 - 1824 CORIANDER DR, KISSIMMEE, FL 34759 28 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1056
       Built: 2026
    Monthly Fee: $198
       Tax: $212 (2025)
    Community: Tuscany Preserve Ph 03
    Villa


    Estimated Monthly Payment: $1,394 (change assumption)
    Mortgage ($1,178) + Fees ($198) + Taxes in 2025 ($18)


    Taxes:$212

    Elementary School: Laurel Elementary

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Lake Marion Creek Middle


  • 1828 CORIANDER DR, KISSIMMEE, FL 34759

    $215,00028 Days on yellowkey   MLS ID: O6401533

    For Sale O6401533 - 1828 CORIANDER DR, KISSIMMEE, FL 34759 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1056
       Built: 2026
    Monthly Fee: $198
       Tax: $212 (2025)
    Community: Tuscany Preserve Ph 03
    Villa


    Estimated Monthly Payment: $1,394 (change assumption)
    Mortgage ($1,178) + Fees ($198) + Taxes in 2025 ($18)


    Taxes:$212

    Elementary School: Laurel Elementary

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Lake Marion Creek Middle


  • KISSIMMEE, FL 34759

    $199,00027 Days on yellowkey   MLS ID: S5148291

    For Sale S5148291 - KISSIMMEE, FL 34759 1 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1104
       Built: 1987
    Monthly Fee: $400
       Tax: $2,350 (2025)
    Community: Golf Villas 02 At Poinciana
    Villa


    Estimated Monthly Payment: $1,686 (change assumption)
    Mortgage ($1,090) + Fees ($400) + Taxes in 2025 ($196)


    Taxes:$2,350

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 116 OCEAN BLUFF DR, KISSIMMEE, FL 34759

    $200,000136 Days on yellowkey   MLS ID: L4958493

    For Sale L4958493 - 116 OCEAN BLUFF DR, KISSIMMEE, FL 34759 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1249
       Built: 2002
    Monthly Fee: $135
       Tax: $2,463 (2025)
    Community: Lake Marion Golf Resort Ph 02
    Villa


    Estimated Monthly Payment: $1,436 (change assumption)
    Mortgage ($1,096) + Fees ($135) + Taxes in 2025 ($205)


    Taxes:$2,463

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2342 BARBADOS CT, KISSIMMEE, FL 34741

    $240,00072 Days on yellowkey   MLS ID: S5145920

    REDUCED by $12,000 (4.8%) on 05/01/2026

    For Sale S5145920 - 2342 BARBADOS CT, KISSIMMEE, FL 34741 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 991
       Built: 1984
    Monthly Fee: $251
       Tax: $2,956 (2025)
    Community: Caribbean Villas Condo Ph A-F
    Villa


    Estimated Monthly Payment: $1,812 (change assumption)
    Mortgage ($1,315) + Fees ($251) + Taxes in 2025 ($246)


    Taxes:$2,956

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2123 ST MARTEEN CT, KISSIMMEE, FL 34741

    $205,00082 Days on yellowkey   MLS ID: O6387879

    For Sale O6387879 - 2123 ST MARTEEN CT, KISSIMMEE, FL 34741 14 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 991
       Built: 1989
    Monthly Fee: $278
       Tax: $312 (2025)
    Community: Caribbean Villas Condo Ph A-F
    Villa


    Estimated Monthly Payment: $1,427 (change assumption)
    Mortgage ($1,123) + Fees ($278) + Taxes in 2025 ($26)


    Taxes:$312

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1987 KEY BAY TRL, KISSIMMEE, FL 34747

    $339,000496 Days on yellowkey   MLS ID: O6270026

    For Sale O6270026 - 1987 KEY BAY TRL, KISSIMMEE, FL 34747 48 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1437
       Built: 2023
    Monthly Fee: $455
       Tax: $7,125 (2024)
    Community: Four Seasons At Orlando Ph 4B
    Villa


    Estimated Monthly Payment: $2,906 (change assumption)
    Mortgage ($1,857) + Fees ($455) + Taxes in 2024 ($594)


    Taxes:$7,125

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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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.