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Kissimmee Short Sales - 99 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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  • 667 HERALDO CT, KISSIMMEE, FL 34758

    $236,000502 Days on yellowkey   MLS ID: S5118760

    3 Days Off yellowkey (back on 2/16/2026)

    SHORT SALE S5118760 - 667 HERALDO CT, KISSIMMEE, FL 34758 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1372
       Built: 1988
    Monthly Fee: $15
       Tax: $622 (2023)
    Community: Poinciana Village 1 Nbhd 3 West
    Single Family


    Estimated Monthly Payment: $1,360 (change assumption)
    Mortgage ($1,293) + Fees ($15) + Taxes in 2023 ($52)


    Taxes:$622

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 3504 SHOREWOOD DR, KISSIMMEE, FL 34746

    $307,000350 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)


  • 1563 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $349,90069 Days on yellowkey   MLS ID: S5147463

    REDUCED by $10,100 (2.8%) on 05/28/2026

    SHORT SALE S5147463 - 1563 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1802
       Built: 2023
    Monthly Fee: $10
       Tax: $7,403 (2025)
    Community: Tohoqua Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,544 (change assumption)
    Mortgage ($1,917) + Fees ($10) + Taxes in 2025 ($617)


    Taxes:$7,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1285 S SOUTH BEACH CIRCLE CIR, KISSIMMEE, FL 34746

    $215,000463 Days on yellowkey   MLS ID: O6289956

    REDUCED by $15,000 (6.5%) on 05/28/2026

    SHORT SALE O6289956 - 1285 S SOUTH BEACH CIRCLE CIR, KISSIMMEE, FL 34746 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1468
       Built: 2005
    Monthly Fee: $289
       Tax: $4,047 (2024)
    Community: Fiesta Key
    Spa: No

    Townhouse


    Estimated Monthly Payment: $1,804 (change assumption)
    Mortgage ($1,178) + Fees ($289) + Taxes in 2024 ($337)


    Taxes:$4,047

    Elementary School: Sunrise Elementary

    High School: Poinciana High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 1286 WISPY CYPRESS DR, KISSIMMEE, FL 34746

    $286,000241 Days on yellowkey   MLS ID: O6354485

    2 Days Off yellowkey (back on 5/28/2026)

    REDUCED by $3,000 (1.0%) on 05/16/2026

    SHORT SALE O6354485 - 1286 WISPY CYPRESS DR, KISSIMMEE, FL 34746 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1918
       Built: 2022
    Monthly Fee: $318
       Tax: $4,565 (2025)
    Community: Cypress Hammock Ph 1
    Townhouse


    Estimated Monthly Payment: $2,266 (change assumption)
    Mortgage ($1,567) + Fees ($318) + Taxes in 2025 ($380)


    Taxes:$4,565

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 189 GRAND CANAL DR, KISSIMMEE, FL 34759

    $240,000269 Days on yellowkey   MLS ID: O6347415

    0 Days Off yellowkey (back on 5/26/2026)

    SHORT SALE O6347415 - 189 GRAND CANAL DR, KISSIMMEE, FL 34759 27 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1240
       Built: 2005
    Monthly Fee: $263
       Tax: $4,308 (2024)
    Community: Solivita Ph 03A
    Single Family


    Estimated Monthly Payment: $1,937 (change assumption)
    Mortgage ($1,315) + Fees ($263) + Taxes in 2024 ($359)


    Taxes:$4,308

    Elementary School: Palmetto Elementary

    High School: Haines City Senior High

    Tax Year: 2024

    Middle School: Lake Marion Creek Middle


  • 534 EAGLE POINTE S, KISSIMMEE, FL 34746

    $300,90056 Days on yellowkey   MLS ID: S5148539

    REDUCED by $25,000 (7.7%) on 05/27/2026

    SHORT SALE S5148539 - 534 EAGLE POINTE S, KISSIMMEE, FL 34746 23 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1975
       Built: 2003
    Monthly Fee: $25
       Tax: $2,011 (2025)
    Community: Eagle Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $1,841 (change assumption)
    Mortgage ($1,649) + Fees ($25) + Taxes in 2025 ($168)


    Taxes:$2,011

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1157 SEASIDE MIST TRL, KISSIMMEE, FL 34747

    $275,00048 Days on yellowkey   MLS ID: O6404561

    3 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $10,000 (3.5%) on 05/18/2026

    SHORT SALE O6404561 - 1157 SEASIDE MIST TRL, KISSIMMEE, FL 34747 18 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1585
       Built: 2023
    Monthly Fee: $257
       Tax: $5,320 (2025)
    Community: Soleil At Westside
    Townhouse


    Estimated Monthly Payment: $2,207 (change assumption)
    Mortgage ($1,507) + Fees ($257) + Taxes in 2025 ($443)


    Taxes:$5,320

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 112 OCEAN BLUFF DR, KISSIMMEE, FL 34759

    $190,000159 Days on yellowkey   MLS ID: O6373558

    1 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $20,000 (9.5%) on 04/18/2026

    SHORT SALE O6373558 - 112 OCEAN BLUFF DR, KISSIMMEE, FL 34759 16 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1616
       Built: 2003
    Monthly Fee: $360
       Tax: $3,271 (2025)
    Community: Lake Marion Golf Resort Ph 02
    Townhouse


    Estimated Monthly Payment: $1,674 (change assumption)
    Mortgage ($1,041) + Fees ($360) + Taxes in 2025 ($273)


    Taxes:$3,271

    Elementary School: Dundee Elem

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Lake Marion Creek Middle


  • 1756 STAMEN DR, KISSIMMEE, FL 34744

    $399,000123 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)


  • 2615 PALISADE BLVD, KISSIMMEE, FL 34741

    $410,000125 Days on yellowkey   MLS ID: O6383132

    REDUCED by $40,000 (8.9%) on 05/22/2026

    SHORT SALE O6383132 - 2615 PALISADE BLVD, KISSIMMEE, FL 34741 20 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2320
       Built: 2017
    Monthly Fee: $170
       Tax: $8,793 (2025)
    Community: Tapestry Ph 2
    Single Family


    Estimated Monthly Payment: $3,149 (change assumption)
    Mortgage ($2,247) + Fees ($170) + Taxes in 2025 ($733)


    Taxes:$8,793

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1153 PERPIGNAN CT, KISSIMMEE, FL 34759

    $249,00031 Days on yellowkey   MLS ID: O6409679

    SHORT SALE O6409679 - 1153 PERPIGNAN CT, KISSIMMEE, FL 34759 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1236
       Built: 1996   Tax: $3,356 (2025)
    Community: Poinciana Village 5 Nbhd 1
    Single Family


    Estimated Monthly Payment: $1,644 (change assumption)
    Mortgage ($1,364) + Taxes in 2025 ($280)


    Taxes:$3,356

    Elementary School: Chestnut Elem

    High School: Liberty High

    Tax Year: 2025

    Middle School: Discovery Intermediate


  • 442 CARAWAY DR, KISSIMMEE, FL 34759

    $227,00081 Days on yellowkey   MLS ID: S5146971

    INCREASED by $17,000 (8.1%) on 05/20/2026

    SHORT SALE S5146971 - 442 CARAWAY DR, KISSIMMEE, FL 34759 18 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1794
       Built: 2007
    Monthly Fee: $317
       Tax: $3,176 (2025)
    Community: Poinciana Nbrhd 03 South Village 07
    Single Family


    Estimated Monthly Payment: $1,825 (change assumption)
    Mortgage ($1,244) + Fees ($317) + Taxes in 2025 ($265)


    Taxes:$3,176

    Elementary School: Laurel Elementary

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Lake Marion Creek Middle


  • 1021 CANNES DR, KISSIMMEE, FL 34759

    $309,999296 Days on yellowkey   MLS ID: P4935645

    0 Days Off yellowkey (back on 11/20/2025)

    SHORT SALE P4935645 - 1021 CANNES DR, KISSIMMEE, FL 34759 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2204
       Built: 2005
    Monthly Fee: $99
       Tax: $4,414 (2024)
    Community: Poinciana Village 5 Nbhd 1
    Single Family


    Estimated Monthly Payment: $2,165 (change assumption)
    Mortgage ($1,699) + Fees ($99) + Taxes in 2024 ($368)


    Taxes:$4,414

    Elementary School: Chestnut Elem

    High School: Liberty High

    Tax Year: 2024

    Middle School: Discovery Intermediate


  • 1406 KISSIMMEE CT, KISSIMMEE, FL 34759

    $200,000362 Days on yellowkey   MLS ID: O6320413

    0 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $29,000 (12.7%) on 05/13/2026

    SHORT SALE O6320413 - 1406 KISSIMMEE CT, KISSIMMEE, FL 34759 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1819
       Built: 2005
    Monthly Fee: $90
       Tax: $3,689 (2024)
    Community: Poinciana Nbrhd 02 West Village 07
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $1,493 (change assumption)
    Mortgage ($1,096) + Fees ($90) + Taxes in 2024 ($307)


    Taxes:$3,689

    Elementary School: Laurel Elementary

    High School: Haines City Senior High

    Tax Year: 2024

    Middle School: Lake Marion Creek Middle


  • 3133 YELLOW LANTANA LN, KISSIMMEE, FL 34747

    $309,500478 Days on yellowkey   MLS ID: O6285491

    2 Days Off yellowkey (back on 3/2/2026)

    SHORT SALE O6285491 - 3133 YELLOW LANTANA LN, KISSIMMEE, FL 34747 27 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1295
       Built: 2006
    Monthly Fee: $594
       Tax: $3,853 (2024)
    Community: Encantada Ph 01
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,611 (change assumption)
    Mortgage ($1,696) + Fees ($594) + Taxes in 2024 ($321)


    Taxes:$3,853

    Elementary School: Westside Elem

    High School: Celebration High

    Tax Year: 2024

    Middle School: West Side


  • 2958 CASTAWAY LN, KISSIMMEE, FL 34747

    $379,000193 Days on yellowkey   MLS ID: O6366361

    0 Days Off yellowkey (back on 5/18/2026)

    SHORT SALE O6366361 - 2958 CASTAWAY LN, KISSIMMEE, FL 34747 27 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1712
       Built: 2023
    Monthly Fee: $474
       Tax: $9,813 (2024)
    Community: Rolling Oaks Ph 7
    Townhouse


    Estimated Monthly Payment: $3,368 (change assumption)
    Mortgage ($2,077) + Fees ($474) + Taxes in 2024 ($818)


    Taxes:$9,813

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1191 SABINE LN, KISSIMMEE, FL 34759

    $229,000291 Days on yellowkey   MLS ID: S5133881

    SHORT SALE S5133881 - 1191 SABINE LN, KISSIMMEE, FL 34759 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1328
       Built: 2015
    Monthly Fee: $90
       Tax: $3,410 (2024)
    Community: Poinciana Nbrhd 06 Village 07
    Single Family


    Estimated Monthly Payment: $1,629 (change assumption)
    Mortgage ($1,255) + Fees ($90) + Taxes in 2024 ($284)


    Taxes:$3,410

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 165 CITRINE LOOP, KISSIMMEE, FL 34758

    $324,000403 Days on yellowkey   MLS ID: S5126819

    SHORT SALE S5126819 - 165 CITRINE LOOP, KISSIMMEE, FL 34758 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1510
       Built: 2023
    Monthly Fee: $85
       Tax: $4,597 (2024)
    Community: Stepping Stone Pod A Ph 2
    Single Family


    Estimated Monthly Payment: $2,243 (change assumption)
    Mortgage ($1,775) + Fees ($85) + Taxes in 2024 ($383)


    Taxes:$4,597

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3111 TURNBERRY BLVD, KISSIMMEE, FL 34744

    $350,000216 Days on yellowkey   MLS ID: S5138322

    129 Days Off yellowkey (back on 5/18/2026)

    SHORT SALE S5138322 - 3111 TURNBERRY BLVD, KISSIMMEE, FL 34744 51 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1400
       Built: 2007
    Monthly Fee: $76
       Tax: $4,633 (2024)
    Community: Turnberry Reserve Unit 2
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($1,918) + Fees ($76) + Taxes in 2024 ($386)


    Taxes:$4,633

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee 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.