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Homes For Sale in Kissimmee 34744 - 358 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 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $434,99914 Days on yellowkey   MLS ID: G5113160

    For Sale G5113160 - 2705 WILLOW GLEN CIR, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1679
       Built: 2001
    Monthly Fee: $23
       Tax: $6,110 (2025)
    Community: Gleneagles
    Single Family


    Estimated Monthly Payment: $2,916 (change assumption)
    Mortgage ($2,383) + Fees ($23) + Taxes in 2025 ($509)


    Taxes:$6,110

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1211 LEHIGH ST, KISSIMMEE, FL 34744

    $359,00073 Days on yellowkey   MLS ID: S5147242

    REDUCED by $5,900 (1.6%) on 06/09/2026

    For Sale S5147242 - 1211 LEHIGH ST, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1685
       Built: 1960   Tax: $5,105 (2025)
    Community: Johnston Park Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,392 (change assumption)
    Mortgage ($1,967) + Taxes in 2025 ($425)


    Taxes:$5,105

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Parkway Middle


  • 1819 WILD RYE WAY, KISSIMMEE, FL 34744

    $379,00010 Days on yellowkey   MLS ID: S5151456

    SHORT SALE S5151456 - 1819 WILD RYE WAY, KISSIMMEE, FL 34744 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2022
    Monthly Fee: $11
       Tax: $6,436 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,624 (change assumption)
    Mortgage ($2,077) + Fees ($11) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1660 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $445,00015 Days on yellowkey   MLS ID: R4911380

    REDUCED by $5,000 (1.1%) on 06/09/2026

    For Sale R4911380 - 1660 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1802
       Built: 2022
    Monthly Fee: $20
       Tax: $6,147 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,971 (change assumption)
    Mortgage ($2,438) + Fees ($20) + Taxes in 2025 ($512)


    Taxes:$6,147

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1686 CONTENTMENT LOOP, KISSIMMEE, FL 34744

    $369,990254 Days on yellowkey   MLS ID: S5136114

    For Sale S5136114 - 1686 CONTENTMENT LOOP, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1755
       Built: 2024
    Monthly Fee: $137
       Tax: $1,351 (2024)
    Community: Tohoqua Ph 3
    Townhouse


    Estimated Monthly Payment: $2,277 (change assumption)
    Mortgage ($2,027) + Fees ($137) + Taxes in 2024 ($113)


    Taxes:$1,351

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2955 RED OAK DR, KISSIMMEE, FL 34744

    $375,00049 Days on yellowkey   MLS ID: O6401588

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6401588 - 2955 RED OAK DR, KISSIMMEE, FL 34744 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1365
       Built: 1996   Tax: $1,310 (2025)
    Community: Westwood Forest
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,164 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($109)


    Taxes:$1,310

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1384 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $939,900490 Days on yellowkey   MLS ID: O6278826

    3 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $15,100 (1.6%) on 04/23/2026

    For Sale O6278826 - 1384 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3606
       Built: 2008   Tax: $4,881 (2023)
    Community: East Lake Shores
    Single Family


    Estimated Monthly Payment: $5,557 (change assumption)
    Mortgage ($5,150) + Taxes in 2023 ($407)


    Taxes:$4,881

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2023

    Middle School: Neptune Middle (6-8)


  • 1763 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744

    $559,500158 Days on yellowkey   MLS ID: O6372301

    4 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $5,400 (1.0%) on 05/26/2026

    For Sale O6372301 - 1763 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2851
       Built: 2018
    Monthly Fee: $11
       Tax: $8,343 (2025)
    Community: Kindred Ph 1D
    Single Family


    Estimated Monthly Payment: $3,772 (change assumption)
    Mortgage ($3,066) + Fees ($11) + Taxes in 2025 ($695)


    Taxes:$8,343

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1670 TAYLOR RIDGE LOOP, KISSIMMEE, FL 34744

    $633,500260 Days on yellowkey   MLS ID: S5135712

    REDUCED by $3,500 (0.5%) on 05/31/2026

    For Sale S5135712 - 1670 TAYLOR RIDGE LOOP, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2359
       Built: 2004
    Monthly Fee: $150
       Tax: $4,749 (2025)
    Community: Taylor Ridge
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,017 (change assumption)
    Mortgage ($3,471) + Fees ($150) + Taxes in 2025 ($396)


    Taxes:$4,749

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744

    $646,11020 Days on yellowkey   MLS ID: O6412075

    INCREASED by $19,000 (3.0%) on 06/08/2026

    For Sale O6412075 - 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744 43 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3598
       Built: 2026
    Monthly Fee: $42
       Tax: $1,329 (2025)
    Community: Tohoqua
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,693 (change assumption)
    Mortgage ($3,540) + Fees ($42) + Taxes in 2025 ($111)


    Taxes:$1,329

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2275 SOUTHBURY DR, KISSIMMEE, FL 34744

    $346,790108 Days on yellowkey   MLS ID: O6386802

    REDUCED by $2,000 (0.6%) on 06/08/2026

    For Sale O6386802 - 2275 SOUTHBURY DR, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1553
       Built: 2026
    Monthly Fee: $130
       Tax: $1,610 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,164 (change assumption)
    Mortgage ($1,900) + Fees ($130) + Taxes in 2025 ($134)


    Taxes:$1,610

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2675 CANDIED APPLE ALY, KISSIMMEE, FL 34744

    $339,00055 Days on yellowkey   MLS ID: O6401700

    REDUCED by $10,000 (2.9%) on 06/08/2026

    For Sale O6401700 - 2675 CANDIED APPLE ALY, KISSIMMEE, FL 34744 53 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1615
       Built: 2025
    Monthly Fee: $142
       Tax: $2,218 (2025)
    Community: Tohoqua Ph 7
    Townhouse


    Estimated Monthly Payment: $2,184 (change assumption)
    Mortgage ($1,857) + Fees ($142) + Taxes in 2025 ($185)


    Taxes:$2,218

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1371 FAIR OAKS AVE, KISSIMMEE, FL 34744

    $370,00017 Days on yellowkey   MLS ID: S5150771

    0 Days Off yellowkey (back on 6/7/2026)

    For Sale S5150771 - 1371 FAIR OAKS AVE, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1771
       Built: 1967   Tax: $1,767 (2025)
    Community: Cadillac Homes
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,175 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($147)


    Taxes:$1,767

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3202 SURFBIRD ST, KISSIMMEE, FL 34744

    $495,00063 Days on yellowkey   MLS ID: O6399070

    For Sale O6399070 - 3202 SURFBIRD ST, KISSIMMEE, FL 34744 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2280
       Built: 2019
    Monthly Fee: $95
       Tax: $4,159 (2025)
    Community: Osprey Ridge
    Single Family


    Estimated Monthly Payment: $3,154 (change assumption)
    Mortgage ($2,712) + Fees ($95) + Taxes in 2025 ($347)


    Taxes:$4,159

    Elementary School: Boggy Creek Elem (K 5)

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1508 JENNI LEE CT, KISSIMMEE, FL 34744

    $459,90033 Days on yellowkey   MLS ID: TB8508177

    REDUCED by $15,000 (3.2%) on 06/08/2026

    For Sale TB8508177 - 1508 JENNI LEE CT, KISSIMMEE, FL 34744 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2077
       Built: 1996
    Monthly Fee: $21
       Tax: $1,877 (2025)
    Community: Woods At Kings Crest The Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,697 (change assumption)
    Mortgage ($2,520) + Fees ($21) + Taxes in 2025 ($156)


    Taxes:$1,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4306 BISCAYNE COVE CT, KISSIMMEE, FL 34744

    $700,000163 Days on yellowkey   MLS ID: O6370990

    REDUCED by $25,000 (3.4%) on 04/21/2026

    For Sale O6370990 - 4306 BISCAYNE COVE CT, KISSIMMEE, FL 34744 54 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3828
       Built: 2015
    Monthly Fee: $108
       Tax: $5,600 (2025)
    Community: North Point Ph 2B-2C
    Single Family


    Estimated Monthly Payment: $4,410 (change assumption)
    Mortgage ($3,836) + Fees ($108) + Taxes in 2025 ($467)


    Taxes:$5,600

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1205 TETON DR, KISSIMMEE, FL 34744

    $342,99036 Days on yellowkey   MLS ID: S5148840

    REDUCED by $11,000 (3.1%) on 05/29/2026

    For Sale S5148840 - 1205 TETON DR, KISSIMMEE, FL 34744 69 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1935
       Built: 2018
    Monthly Fee: $158
       Tax: $3,699 (2025)
    Community: Heritage Run
    Townhouse


    Estimated Monthly Payment: $2,346 (change assumption)
    Mortgage ($1,879) + Fees ($158) + Taxes in 2025 ($308)


    Taxes:$3,699

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2670 REAGAN LN, KISSIMMEE, FL 34744

    $363,000112 Days on yellowkey   MLS ID: O6385604

    REDUCED by $7,000 (1.9%) on 06/01/2026

    For Sale O6385604 - 2670 REAGAN LN, KISSIMMEE, FL 34744 65 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1294
       Built: 1981   Tax: $1,125 (2025)
    Community: Gehrett Gardens
    Single Family


    Estimated Monthly Payment: $2,083 (change assumption)
    Mortgage ($1,989) + Taxes in 2025 ($94)


    Taxes:$1,125

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1527 GANTS CIR, KISSIMMEE, FL 34744

    $589,00034 Days on yellowkey   MLS ID: O6407722

    REDUCED by $10,000 (1.7%) on 06/07/2026

    For Sale O6407722 - 1527 GANTS CIR, KISSIMMEE, FL 34744 44 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2871
       Built: 2002
    Monthly Fee: $75
       Tax: $4,456 (2025)
    Community: Ashley Cove Unit 3
    Single Family


    Estimated Monthly Payment: $3,674 (change assumption)
    Mortgage ($3,227) + Fees ($75) + Taxes in 2025 ($371)


    Taxes:$4,456

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 205 OWENSHIRE CIR, KISSIMMEE, FL 34744

    $359,90014 Days on yellowkey   MLS ID: S5151174

    For Sale S5151174 - 205 OWENSHIRE CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 2003
    Monthly Fee: $23
       Tax: $5,644 (2025)
    Community: Remington Prcl K Ph 3
    Single Family


    Estimated Monthly Payment: $2,465 (change assumption)
    Mortgage ($1,972) + Fees ($23) + Taxes in 2025 ($470)


    Taxes:$5,644

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.