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Homes For Sale in Kissimmee 34744 - 290 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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  • 2678 FOREST VIEW LN, KISSIMMEE, FL 34744

    $348,99034 Days on yellowkey   MLS ID: O6391606

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

    For Sale O6391606 - 2678 FOREST VIEW LN, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1194
       Built: 1990   Tax: $1,689 (2025)
    Community: Oak Run Unit 7
    Single Family


    Estimated Monthly Payment: $2,053 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($141)


    Taxes:$1,689

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 229 STRATHMORE CIR, KISSIMMEE, FL 34744

    $489,900131 Days on yellowkey   MLS ID: O6367119

    0 Days Off yellowkey (back on 4/21/2026)

    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


  • 2539 CHRISTINE DR, KISSIMMEE, FL 34744

    $379,998235 Days on yellowkey   MLS ID: O6340298

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

    For Sale O6340298 - 2539 CHRISTINE DR, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1500
       Built: 1981   Tax: $1,084 (2024)
    Community: Mill Run Unit 3
    Single Family


    Estimated Monthly Payment: $2,172 (change assumption)
    Mortgage ($2,082) + Taxes in 2024 ($90)


    Taxes:$1,084

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3012 VILLA PRECIOSA DR, KISSIMMEE, FL 34744

    $434,900262 Days on yellowkey   MLS ID: O6310848

    For Sale O6310848 - 3012 VILLA PRECIOSA DR, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2074
       Built: 2004
    Monthly Fee: $160
       Tax: $4,927 (2024)
    Community: Villa Sol Ph 1 Village 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,954 (change assumption)
    Mortgage ($2,383) + Fees ($160) + Taxes in 2024 ($411)


    Taxes:$4,927

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1325 CYPRESS ARBOR, KISSIMMEE, FL 34744

    $275,0007 Days on yellowkey   MLS ID: O6398060

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6398060 - 1325 CYPRESS ARBOR, KISSIMMEE, FL 34744 15 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 957
       Built: 1986   Tax: $806 (2025)
    Community: Cypress Arbor
    Single Family


    Estimated Monthly Payment: $1,574 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($67)


    Taxes:$806

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 106 BURRELL CIR, KISSIMMEE, FL 34744

    $525,00040 Days on yellowkey   MLS ID: S5145477

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

    Bed: 5   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


  • 1502 JADEWOOD WAY, KISSIMMEE, FL 34744

    $350,000611 Days on yellowkey   MLS ID: O6233314

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

    SHORT SALE O6233314 - 1502 JADEWOOD WAY, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022
    Monthly Fee: $11
       Tax: $7,144 (2025)
    Community: Kindred Ph 2C & 2D Pb 30 Pgs 74-80 Lot 323
    Single Family


    Estimated Monthly Payment: $2,524 (change assumption)
    Mortgage ($1,918) + Fees ($11) + Taxes in 2025 ($595)


    Taxes:$7,144

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2045 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $456,9908 Days on yellowkey   MLS ID: O6398932

    2 Days Off yellowkey (back on 4/21/2026)

    For Sale O6398932 - 2045 WALNUT CREEK DR, KISSIMMEE, FL 34744 47 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2447
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,822 (change assumption)
    Mortgage ($2,504) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1709 MICHIGAN AVE #C, KISSIMMEE, FL 34744

    $145,0002 Days on yellowkey   MLS ID: S5148282

    For Sale S5148282 - 1709 MICHIGAN AVE #C, KISSIMMEE, FL 34744 14 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1118
       Built: 1973
    Monthly Fee: $298
       Tax: $2,400 (2025)
    Community: Essex Park Villas
    Condo


    Estimated Monthly Payment: $1,293 (change assumption)
    Mortgage ($795) + Fees ($298) + Taxes in 2025 ($200)


    Taxes:$2,400

    Elementary School: Deerwood Elem (Osceola Cty)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2057 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $456,9902 Days on yellowkey   MLS ID: O6400629

    For Sale O6400629 - 2057 WALNUT CREEK DR, KISSIMMEE, FL 34744 51 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2447
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,822 (change assumption)
    Mortgage ($2,504) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2362 SOUTHBURY DR, KISSIMMEE, FL 34744

    $394,490163 Days on yellowkey   MLS ID: O6359381

    6 Days Off yellowkey (back on 1/12/2026)

    For Sale O6359381 - 2362 SOUTHBURY DR, KISSIMMEE, FL 34744 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $130
       Tax: $2,384 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,490 (change assumption)
    Mortgage ($2,162) + Fees ($130) + Taxes in 2025 ($199)


    Taxes:$2,384

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $457,00055 Days on yellowkey   MLS ID: S5144261

    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: $2,900 (change assumption)
    Mortgage ($2,504) + Taxes in 2025 ($396)


    Taxes:$4,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 103 DELLWOOD DR, KISSIMMEE, FL 34744

    $329,00072 Days on yellowkey   MLS ID: S5143443

    For Sale S5143443 - 103 DELLWOOD DR, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1368
       Built: 1955   Tax: $5,415 (2025)
    Community: Dellwood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,254 (change assumption)
    Mortgage ($1,803) + Taxes in 2025 ($451)


    Taxes:$5,415

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2723 CALLAWAY LN, KISSIMMEE, FL 34744

    $435,00010 Days on yellowkey   MLS ID: O6397750

    For Sale O6397750 - 2723 CALLAWAY LN, KISSIMMEE, FL 34744 56 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 2005
    Monthly Fee: $78
       Tax: $6,939 (2024)
    Community: Remington Prcl M1
    Single Family


    Estimated Monthly Payment: $3,040 (change assumption)
    Mortgage ($2,384) + Fees ($78) + Taxes in 2024 ($578)


    Taxes:$6,939

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1519 JADEWOOD WAY, KISSIMMEE, FL 34744

    $549,00012 Days on yellowkey   MLS ID: S5147592

    INCREASED by $10,000 (1.9%) on 04/20/2026

    For Sale S5147592 - 1519 JADEWOOD WAY, KISSIMMEE, FL 34744 27 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2601
       Built: 2022
    Monthly Fee: $10
       Tax: $7,660 (2025)
    Community: Kindred Ph 1
    Single Family


    Estimated Monthly Payment: $3,656 (change assumption)
    Mortgage ($3,008) + Fees ($10) + Taxes in 2025 ($638)


    Taxes:$7,660

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 4424 SILVER CREEK ST, KISSIMMEE, FL 34744

    $484,90089 Days on yellowkey   MLS ID: L4958851

    REDUCED by $10,000 (2.0%) on 04/20/2026

    For Sale L4958851 - 4424 SILVER CREEK ST, KISSIMMEE, FL 34744 28 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2370
       Built: 2019
    Monthly Fee: $123
       Tax: $6,332 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Single Family


    Estimated Monthly Payment: $3,308 (change assumption)
    Mortgage ($2,657) + Fees ($123) + Taxes in 2025 ($528)


    Taxes:$6,332

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2695 HOLIDAY WOODS DR, KISSIMMEE, FL 34744

    $299,5006 Days on yellowkey   MLS ID: S5147602

    0 Days Off yellowkey (back on 4/19/2026)

    For Sale S5147602 - 2695 HOLIDAY WOODS DR, KISSIMMEE, FL 34744 53 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1100
       Built: 1981   Tax: $1,429 (2025)
    Community: Holiday Woods
    Single Family


    Estimated Monthly Payment: $1,760 (change assumption)
    Mortgage ($1,641) + Taxes in 2025 ($119)


    Taxes:$1,429

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $440,00020 Days on yellowkey   MLS ID: O6395467

    For Sale O6395467 - 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 2022
    Monthly Fee: $30
       Tax: $1,907 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,600 (change assumption)
    Mortgage ($2,411) + Fees ($30) + Taxes in 2025 ($159)


    Taxes:$1,907

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: None


  • 1756 STAMEN DR, KISSIMMEE, FL 34744

    $449,90063 Days on yellowkey   MLS ID: TB8475839

    SHORT SALE TB8475839 - 1756 STAMEN DR, KISSIMMEE, FL 34744 32 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: $3,135 (change assumption)
    Mortgage ($2,465) + 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)


  • 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $449,90030 Days on yellowkey   MLS ID: O6390965

    REDUCED by $9,100 (2.0%) on 04/20/2026

    For Sale O6390965 - 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744 73 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2339
       Built: 2023
    Monthly Fee: $11
       Tax: $3,358 (2025)
    Community: Kindred Ph 3A
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,756 (change assumption)
    Mortgage ($2,465) + Fees ($11) + Taxes in 2025 ($280)


    Taxes:$3,358

    Elementary School: None

    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.