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Kissimmee Short Sales - 84 homes

Kissimmee Short Sale Homes are located in Osceola County, Florida. Find short sale homes for sale in Miami with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Kissimmee short sale houses.

Location: Kissimmee

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  • 41 DORSET DR, KISSIMMEE, FL 34758

    $350,00090 Days on yellowkey   MLS ID: O6386472

    0 Days Off yellowkey (back on 5/8/2026)

    REDUCED by $14,990 (4.1%) on 04/07/2026

    SHORT SALE O6386472 - 41 DORSET DR, KISSIMMEE, FL 34758 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 2024
    Monthly Fee: $90
       Tax: $4,842 (2025)
    Community: Poinciana Village 2 Nbhd 1
    Single Family


    Estimated Monthly Payment: $2,411 (change assumption)
    Mortgage ($1,918) + Fees ($90) + Taxes in 2025 ($403)


    Taxes:$4,842

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17 TROTTERS CIR, KISSIMMEE, FL 34743

    $230,00021 Days on yellowkey   MLS ID: S5149373

    0 Days Off yellowkey (back on 5/8/2026)

    SHORT SALE S5149373 - 17 TROTTERS CIR, KISSIMMEE, FL 34743 3 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1120
       Built: 1984   Tax: $4,313 (2025)
    Community: Bvl Unit 11 1St Add
    Single Family


    Estimated Monthly Payment: $1,620 (change assumption)
    Mortgage ($1,260) + Taxes in 2025 ($359)


    Taxes:$4,313

    Elementary School: Boggy Creek Elem (K 5)

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Parkway Middle


  • 305 CHELMSFORD CT, KISSIMMEE, FL 34758

    $275,000162 Days on yellowkey   MLS ID: O6367634

    1 Days Off yellowkey (back on 12/22/2025)

    SHORT SALE O6367634 - 305 CHELMSFORD CT, KISSIMMEE, FL 34758 19 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 2017
    Monthly Fee: $90
       Tax: $3,916 (2024)
    Community: Poinciana Village 2 Nbhd 1
    Single Family


    Estimated Monthly Payment: $1,923 (change assumption)
    Mortgage ($1,507) + Fees ($90) + Taxes in 2024 ($326)


    Taxes:$3,916

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4557 TEOLI CT, KISSIMMEE, FL 34746

    $249,99045 Days on yellowkey   MLS ID: S5147626

    REDUCED by $56,010 (18.3%) on 05/08/2026

    SHORT SALE S5147626 - 4557 TEOLI CT, KISSIMMEE, FL 34746 29 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1552
       Built: 2023
    Monthly Fee: $216
       Tax: $4,715 (2025)
    Community: Reedy Reserve Ph 3
    Townhouse


    Estimated Monthly Payment: $1,979 (change assumption)
    Mortgage ($1,370) + Fees ($216) + Taxes in 2025 ($393)


    Taxes:$4,715

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8824 BENGAL CT, KISSIMMEE, FL 34747

    $670,900223 Days on yellowkey   MLS ID: O6353390

    SHORT SALE O6353390 - 8824 BENGAL CT, KISSIMMEE, FL 34747 51 photos

    Bed: 8   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4041
       Built: 2019
    Monthly Fee: $550
       Tax: $12,811 (2024)
    Community: Windsor At Westside Ph 2B-1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,294 (change assumption)
    Mortgage ($3,676) + Fees ($550) + Taxes in 2024 ($1,068)


    Taxes:$12,811

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 932 ALBERTVILLE CT, KISSIMMEE, FL 34759

    $289,00030 Days on yellowkey   MLS ID: S5148781

    1 Days Off yellowkey (back on 5/8/2026)

    SHORT SALE S5148781 - 932 ALBERTVILLE CT, KISSIMMEE, FL 34759 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1684
       Built: 2022
    Monthly Fee: $85
       Tax: $4,182 (2025)
    Community: Poinciana Village 5 Nbhd 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,017 (change assumption)
    Mortgage ($1,584) + Fees ($85) + Taxes in 2025 ($349)


    Taxes:$4,182

    Elementary School: Chestnut Elem

    High School: Liberty High

    Tax Year: 2025

    Middle School: Discovery Intermediate


  • 710 BLUEBILL PL, KISSIMMEE, FL 34759

    $210,00084 Days on yellowkey   MLS ID: O6383958

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

    REDUCED by $15,000 (6.7%) on 04/29/2026

    SHORT SALE O6383958 - 710 BLUEBILL PL, KISSIMMEE, FL 34759 9 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1252
       Built: 2001
    Monthly Fee: $90
       Tax: $761 (2025)
    Community: Poinciana Nbrhd 05 North Village 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,304 (change assumption)
    Mortgage ($1,151) + Fees ($90) + Taxes in 2025 ($63)


    Taxes:$761

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 531 GLADE CT, KISSIMMEE, FL 34758

    $299,00039 Days on yellowkey   MLS ID: L4961195

    SHORT SALE L4961195 - 531 GLADE CT, KISSIMMEE, FL 34758 22 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1872
       Built: 2022
    Monthly Fee: $81
       Tax: $3,897 (2025)
    Community: Poinciana Village 1 Nbhd 1 South
    Single Family


    Estimated Monthly Payment: $2,044 (change assumption)
    Mortgage ($1,638) + Fees ($81) + Taxes in 2025 ($325)


    Taxes:$3,897

    Elementary School: Highlands Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Horizon Middle


  • 3058 PIRATE WAY, KISSIMMEE, FL 34747

    $375,00057 Days on yellowkey   MLS ID: O6394128

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

    SHORT SALE O6394128 - 3058 PIRATE WAY, KISSIMMEE, FL 34747 61 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1305
       Built: 2018
    Monthly Fee: $468
       Tax: $9,460 (2025)
    Community: Rolling Oaks Ph 5
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,311 (change assumption)
    Mortgage ($2,055) + Fees ($468) + Taxes in 2025 ($788)


    Taxes:$9,460

    Elementary School: Westside K-8

    High School: Celebration High

    Tax Year: 2025

    Middle School: West Side


  • 3557 VALLEYVIEW DR, KISSIMMEE, FL 34746

    $350,00024 Days on yellowkey   MLS ID: S5148852

    SHORT SALE S5148852 - 3557 VALLEYVIEW DR, KISSIMMEE, FL 34746 11 photos

    Bed: 4   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 3123
       Built: 2006
    Monthly Fee: $700
       Tax: $7,257 (2025)
    Community: Bellalago Ph 3M
    Single Family


    Estimated Monthly Payment: $3,223 (change assumption)
    Mortgage ($1,918) + Fees ($700) + Taxes in 2025 ($605)


    Taxes:$7,257

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1904 TOHOQUA BLVD, KISSIMMEE, FL 34744

    $340,00084 Days on yellowkey   MLS ID: O6387203

    REDUCED by $10,000 (2.9%) on 05/04/2026

    SHORT SALE O6387203 - 1904 TOHOQUA BLVD, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2023
    Monthly Fee: $140
       Tax: $6,407 (2025)
    Community: Tohoqua Ph 6
    Townhouse


    Estimated Monthly Payment: $2,537 (change assumption)
    Mortgage ($1,863) + Fees ($140) + Taxes in 2025 ($534)


    Taxes:$6,407

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Harmony Middle


  • 683 BAY LEAF DR, KISSIMMEE, FL 34759

    $199,000286 Days on yellowkey   MLS ID: S5132837

    2 Days Off yellowkey (back on 2/11/2026)

    SHORT SALE S5132837 - 683 BAY LEAF DR, KISSIMMEE, FL 34759 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1635
       Built: 2023
    Monthly Fee: $216
       Tax: $3,777 (2024)
    Community: Tuscany Preserve Ph 4 North
    Spa: No

    Townhouse


    Estimated Monthly Payment: $1,621 (change assumption)
    Mortgage ($1,090) + Fees ($216) + Taxes in 2024 ($315)


    Taxes:$3,777

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 209 CIMARRON DR, KISSIMMEE, FL 34759

    $295,00057 Days on yellowkey   MLS ID: O6395162

    REDUCED by $20,000 (6.3%) on 05/04/2026

    SHORT SALE O6395162 - 209 CIMARRON DR, KISSIMMEE, FL 34759 54 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1684
       Built: 2022
    Monthly Fee: $100
       Tax: $3,380 (2025)
    Community: Poinciana Nbrhd 06 Village 07
    Single Family


    Estimated Monthly Payment: $1,998 (change assumption)
    Mortgage ($1,616) + Fees ($100) + Taxes in 2025 ($282)


    Taxes:$3,380

    Elementary School: Sandhill Elem

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Lake Marion Creek Middle


  • 3504 SHOREWOOD DR, KISSIMMEE, FL 34746

    $307,000326 Days on yellowkey   MLS ID: O6319449

    0 Days Off yellowkey (back on 5/3/2026)

    SHORT SALE O6319449 - 3504 SHOREWOOD DR, KISSIMMEE, FL 34746 66 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2390
       Built: 2003
    Monthly Fee: $159
       Tax: $4,024 (2024)
    Community: Bellalago
    Single Family


    Estimated Monthly Payment: $2,176 (change assumption)
    Mortgage ($1,682) + Fees ($159) + Taxes in 2024 ($335)


    Taxes:$4,024

    Elementary School: Bellalago Charter Academy (K-8)

    High School: Liberty High

    Tax Year: 2024

    Middle School: Bellalago Charter Academy (K-8)


  • 2239 SANTA LUCIA ST, KISSIMMEE, FL 34743

    $320,497266 Days on yellowkey   MLS ID: O6337080

    REDUCED by $1,000 (0.3%) on 04/02/2026

    SHORT SALE O6337080 - 2239 SANTA LUCIA ST, KISSIMMEE, FL 34743 16 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1059
       Built: 1999
    Monthly Fee: $27
       Tax: $3,914 (2024)
    Community: Marisol Ph 2
    Single Family


    Estimated Monthly Payment: $2,109 (change assumption)
    Mortgage ($1,756) + Fees ($27) + Taxes in 2024 ($326)


    Taxes:$3,914

    Elementary School: Cypress Elem (K 6)

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 119 ANZIO DR, KISSIMMEE, FL 34758

    $215,000225 Days on yellowkey   MLS ID: O6352855

    SHORT SALE O6352855 - 119 ANZIO DR, KISSIMMEE, FL 34758 33 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1137
       Built: 2004
    Monthly Fee: $90
       Tax: $2,925 (2024)
    Community: Poinciana Village 1 Nbhd 2
    Single Family


    Estimated Monthly Payment: $1,512 (change assumption)
    Mortgage ($1,178) + Fees ($90) + Taxes in 2024 ($244)


    Taxes:$2,925

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 426 CARDINAL CT, KISSIMMEE, FL 34759

    $247,00072 Days on yellowkey   MLS ID: S5145991

    1 Days Off yellowkey (back on 5/2/2026)

    SHORT SALE S5145991 - 426 CARDINAL CT, KISSIMMEE, FL 34759 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 2001
    Monthly Fee: $100
       Tax: $4,023 (2025)
    Community: Poinciana Nbrhd 05 North Village 03
    Single Family


    Estimated Monthly Payment: $1,789 (change assumption)
    Mortgage ($1,353) + Fees ($100) + Taxes in 2025 ($335)


    Taxes:$4,023

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 667 BAY LEAF DR, KISSIMMEE, FL 34759

    $190,000111 Days on yellowkey   MLS ID: O6380636

    1 Days Off yellowkey (back on 2/15/2026)

    SHORT SALE O6380636 - 667 BAY LEAF DR, KISSIMMEE, FL 34759 13 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1635
       Built: 2023
    Monthly Fee: $270
       Tax: $3,736 (2025)
    Community: Tuscany Preservie Ph 4
    Townhouse


    Estimated Monthly Payment: $1,622 (change assumption)
    Mortgage ($1,041) + Fees ($270) + Taxes in 2025 ($311)


    Taxes:$3,736

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2626 ANDROS LN, KISSIMMEE, FL 34747

    $240,000215 Days on yellowkey   MLS ID: S5137340

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

    SHORT SALE | FORECLOSURE S5137340 - 2626 ANDROS LN, KISSIMMEE, FL 34747 25 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1362
       Built: 2007
    Monthly Fee: $327
       Tax: $3,086 (2024)
    Community: Crestwynd Bay
    Townhouse


    Estimated Monthly Payment: $1,899 (change assumption)
    Mortgage ($1,315) + Fees ($327) + Taxes in 2024 ($257)


    Taxes:$3,086

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4366 SUNNY CREEK PL, KISSIMMEE, FL 34746

    $325,00028 Days on yellowkey   MLS ID: O6402833

    SHORT SALE O6402833 - 4366 SUNNY CREEK PL, KISSIMMEE, FL 34746 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1263
       Built: 2020
    Monthly Fee: $155
       Tax: $5,146 (2025)
    Community: Storey Creek 40S
    Single Family


    Estimated Monthly Payment: $2,365 (change assumption)
    Mortgage ($1,781) + Fees ($155) + Taxes in 2025 ($429)


    Taxes:$5,146

    Elementary School: Pleasant Hill Elem

    High School: Poinciana High School

    Tax Year: 2025

    Middle School: Horizon Middle




Why Bother Searching Elsewhere for Kissimmee Short Sale Homes?

Kissimmee home, townhome, and condo, villa, and other listing sales 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 short sale homes in Kissimmee . You can use our website to view Multiple Listing Service (MLS) data on Kissimmee short sale properties. 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 Kissimmee short sale 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.