REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Homes For Sale in Kissimmee 34744 - 338 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

Sort:
  • 1425 RIVIERA DR, KISSIMMEE, FL 34744

    $944,90089 Days on yellowkey   MLS ID: O6386384

    For Sale O6386384 - 1425 RIVIERA DR, KISSIMMEE, FL 34744 82 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4654
       Built: 2002
    Monthly Fee: $183
       Tax: $7,220 (2025)
    Community: Regal Bay
    Single Family


    Estimated Monthly Payment: $5,962 (change assumption)
    Mortgage ($5,177) + Fees ($183) + Taxes in 2025 ($602)


    Taxes:$7,220

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1350 ROCKY RD, KISSIMMEE, FL 34744

    $325,00025 Days on yellowkey   MLS ID: O6405639

    For Sale O6405639 - 1350 ROCKY RD, KISSIMMEE, FL 34744 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1108
       Built: 1983   Tax: $4,613 (2025)
    Community: Pebble Creek
    Single Family


    Estimated Monthly Payment: $2,165 (change assumption)
    Mortgage ($1,781) + Taxes in 2025 ($384)


    Taxes:$4,613

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1636 BARBERRY DR, KISSIMMEE, FL 34744

    $560,00099 Days on yellowkey   MLS ID: S5144068

    For Sale S5144068 - 1636 BARBERRY DR, KISSIMMEE, FL 34744 65 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2851
       Built: 2023
    Monthly Fee: $11
       Tax: $7,432 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,699 (change assumption)
    Mortgage ($3,068) + Fees ($11) + Taxes in 2025 ($619)


    Taxes:$7,432

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744

    $627,1104 Days on yellowkey   MLS ID: O6412075

    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: $3,589 (change assumption)
    Mortgage ($3,436) + 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)


  • 1767 SMARTS RULE ST, KISSIMMEE, FL 34744

    $509,90023 Days on yellowkey   MLS ID: S5149626

    For Sale S5149626 - 1767 SMARTS RULE ST, KISSIMMEE, FL 34744 38 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2764
       Built: 2022
    Monthly Fee: $1
       Tax: $7,949 (2024)
    Community: Tohoqua Ph 1B
    Single Family


    Estimated Monthly Payment: $3,457 (change assumption)
    Mortgage ($2,794) + Fees ($1) + Taxes in 2024 ($662)


    Taxes:$7,949

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2093 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $398,99085 Days on yellowkey   MLS ID: O6389078

    REDUCED by $3,000 (0.7%) on 05/28/2026

    For Sale O6389078 - 2093 WALNUT CREEK DR, KISSIMMEE, FL 34744 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1614
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,504 (change assumption)
    Mortgage ($2,186) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2609 MILL RUN BLVD, KISSIMMEE, FL 34744

    $394,990Listed 06/02/2026 10:08AM   MLS ID: S5150924

    For Sale S5150924 - 2609 MILL RUN BLVD, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1280
       Built: 1986   Tax: $5,034 (2024)
    Community: Mill Run Unit 5
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,584 (change assumption)
    Mortgage ($2,164) + Taxes in 2024 ($420)


    Taxes:$5,034

    Elementary School: Michigan Avenue Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 162 HARWOOD CIR, KISSIMMEE, FL 34744

    $463,5001 Day on yellowkey   MLS ID: O6412762

    FORECLOSURE O6412762 - 162 HARWOOD CIR, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2516
       Built: 1998
    Monthly Fee: $14
       Tax: $6,859 (2025)
    Community: Remington Ph 1 Tr D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,125 (change assumption)
    Mortgage ($2,540) + Fees ($14) + Taxes in 2025 ($572)


    Taxes:$6,859

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2604 SUMMER CLOUDS WAY, KISSIMMEE, FL 34744

    $429,99039 Days on yellowkey   MLS ID: O6401673

    REDUCED by $5,010 (1.2%) on 05/29/2026

    For Sale O6401673 - 2604 SUMMER CLOUDS WAY, KISSIMMEE, FL 34744 75 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2214
       Built: 2022
    Monthly Fee: $10
       Tax: $7,753 (2025)
    Community: Tohoqua Ph 4A
    Single Family


    Estimated Monthly Payment: $3,012 (change assumption)
    Mortgage ($2,356) + Fees ($10) + Taxes in 2025 ($646)


    Taxes:$7,753

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3824 BLUE DASHER DR, KISSIMMEE, FL 34744

    $499,990365 Days on yellowkey   MLS ID: O6314514

    For Sale O6314514 - 3824 BLUE DASHER DR, KISSIMMEE, FL 34744 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3783
       Built: 2004
    Monthly Fee: $106
       Tax: $6,729 (2024)
    Community: Springlake Village Ph 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,406 (change assumption)
    Mortgage ($2,740) + Fees ($106) + Taxes in 2024 ($561)


    Taxes:$6,729

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 636 ADRIANE PARK CIR, KISSIMMEE, FL 34744

    $474,9008 Days on yellowkey   MLS ID: S5150339

    0 Days Off yellowkey (back on 5/27/2026)

    For Sale S5150339 - 636 ADRIANE PARK CIR, KISSIMMEE, FL 34744 49 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2444
       Built: 1992
    Monthly Fee: $37
       Tax: $3,345 (2025)
    Community: Adriane Park
    Single Family


    Estimated Monthly Payment: $2,918 (change assumption)
    Mortgage ($2,602) + Fees ($37) + Taxes in 2025 ($279)


    Taxes:$3,345

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2356 VALLEY AVE, KISSIMMEE, FL 34744

    $360,00081 Days on yellowkey   MLS ID: O6390430

    4 Days Off yellowkey (back on 6/2/2026)

    REDUCED by $5,000 (1.4%) on 05/05/2026

    For Sale O6390430 - 2356 VALLEY AVE, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1855
       Built: 1973   Tax: $671 (2025)
    Community: Town & Country Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,028 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($56)


    Taxes:$671

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2305 JESSICA LN, KISSIMMEE, FL 34744

    $465,00019 Days on yellowkey   MLS ID: O6407917

    For Sale O6407917 - 2305 JESSICA LN, KISSIMMEE, FL 34744 46 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1820
       Built: 2000
    Monthly Fee: $14
       Tax: $4,461 (2025)
    Community: Woods At Kings Crest The Ph 4
    Single Family


    Estimated Monthly Payment: $2,934 (change assumption)
    Mortgage ($2,548) + Fees ($14) + Taxes in 2025 ($372)


    Taxes:$4,461

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 302 E DRURY AVE, KISSIMMEE, FL 34744

    $368,000Listed 06/02/2026 11:19AM   MLS ID: O6411839

    For Sale O6411839 - 302 E DRURY AVE, KISSIMMEE, FL 34744 41 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1528
       Built: 1950   Tax: $778 (2025)
    Community: Cape Breeze
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,081 (change assumption)
    Mortgage ($2,016) + Taxes in 2025 ($65)


    Taxes:$778

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3210 QUEEN ALEXANDRIA DR, KISSIMMEE, FL 34744

    $369,90081 Days on yellowkey   MLS ID: O6389027

    REDUCED by $12,100 (3.2%) on 06/01/2026

    For Sale O6389027 - 3210 QUEEN ALEXANDRIA DR, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1541
       Built: 2011
    Monthly Fee: $136
       Tax: $4,861 (2025)
    Community: Raintree At Springlake Village Ph 2
    Single Family


    Estimated Monthly Payment: $2,568 (change assumption)
    Mortgage ($2,027) + Fees ($136) + Taxes in 2025 ($405)


    Taxes:$4,861

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744

    $515,00050 Days on yellowkey   MLS ID: S5147642

    REDUCED by $15,000 (2.8%) on 05/20/2026

    For Sale S5147642 - 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744 41 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2930
       Built: 1996
    Monthly Fee: $13
       Tax: $6,439 (2025)
    Community: Remington Ph 1 Tr E
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,371 (change assumption)
    Mortgage ($2,822) + Fees ($13) + Taxes in 2025 ($537)


    Taxes:$6,439

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 429 JANICE KAY PL, KISSIMMEE, FL 34744

    $450,00085 Days on yellowkey   MLS ID: S5145448

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

    For Sale S5145448 - 429 JANICE KAY PL, KISSIMMEE, FL 34744 20 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2906
       Built: 2004
    Monthly Fee: $14
       Tax: $2,737 (2024)
    Community: Eagle Point
    Single Family


    Estimated Monthly Payment: $2,708 (change assumption)
    Mortgage ($2,466) + Fees ($14) + Taxes in 2024 ($228)


    Taxes:$2,737

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1816 HOWARD MESA DR, KISSIMMEE, FL 34744

    $472,99029 Days on yellowkey   MLS ID: O6404697

    2 Days Off yellowkey (back on 6/2/2026)

    INCREASED by $2,000 (0.4%) on 05/12/2026

    For Sale O6404697 - 1816 HOWARD MESA 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: $2,910 (change assumption)
    Mortgage ($2,592) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1800 HOWARD MESA DR, KISSIMMEE, FL 34744

    $421,99029 Days on yellowkey   MLS ID: O6404555

    2 Days Off yellowkey (back on 6/2/2026)

    INCREASED by $2,000 (0.5%) on 05/12/2026

    For Sale O6404555 - 1800 HOWARD MESA DR, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,630 (change assumption)
    Mortgage ($2,312) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744

    $139,0001 Day on yellowkey   MLS ID: S5150908

    For Sale S5150908 - 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744 9 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1118
       Built: 1973
    Monthly Fee: $345
       Tax: $2,118 (2025)
    Community: Essex Park Villas Condo
    Condo


    Estimated Monthly Payment: $1,283 (change assumption)
    Mortgage ($762) + Fees ($345) + Taxes in 2025 ($176)


    Taxes:$2,118

    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.