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Homes For Sale in Kissimmee 34744 - 354 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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  • 231 STRATHMORE CIR, KISSIMMEE, FL 34744

    $459,900123 Days on yellowkey   MLS ID: S5145096

    For Sale S5145096 - 231 STRATHMORE CIR, KISSIMMEE, FL 34744 49 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2262
       Built: 1996
    Monthly Fee: $18
       Tax: $5,082 (2025)
    Community: C
    Single Family


    Estimated Monthly Payment: $2,961 (change assumption)
    Mortgage ($2,520) + Fees ($18) + Taxes in 2025 ($424)


    Taxes:$5,082

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2491 HASSONITE ST, KISSIMMEE, FL 34744

    $289,00056 Days on yellowkey   MLS ID: O6407957

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

    REDUCED by $10,000 (3.3%) on 06/10/2026

    For Sale O6407957 - 2491 HASSONITE ST, KISSIMMEE, FL 34744 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1734
       Built: 2007
    Monthly Fee: $170
       Tax: $3,846 (2025)
    Community: Amber Pointe
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,074 (change assumption)
    Mortgage ($1,584) + Fees ($170) + Taxes in 2025 ($320)


    Taxes:$3,846

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1652 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $399,900344 Days on yellowkey   MLS ID: O6326699

    For Sale O6326699 - 1652 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2537
       Built: 2022
    Monthly Fee: $10
       Tax: $7,997 (2024)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,868 (change assumption)
    Mortgage ($2,191) + Fees ($10) + Taxes in 2024 ($666)


    Taxes:$7,997

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1320 MILL CREEK PL, KISSIMMEE, FL 34744

    $349,00018 Days on yellowkey   MLS ID: O6419178

    For Sale O6419178 - 1320 MILL CREEK PL, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1363
       Built: 1979   Tax: $1,731 (2025)
    Community: Sweetwood Cove
    Single Family


    Estimated Monthly Payment: $2,057 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($144)


    Taxes:$1,731

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1804 HOWARD MESA DR, KISSIMMEE, FL 34744

    $389,99053 Days on yellowkey   MLS ID: O6409252

    REDUCED by $5,000 (1.3%) on 07/02/2026

    For Sale O6409252 - 1804 HOWARD MESA DR, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,455 (change assumption)
    Mortgage ($2,137) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 237 STRATHMORE CIR, KISSIMMEE, FL 34744

    $424,90068 Days on yellowkey   MLS ID: O6403214

    REDUCED by $10,100 (2.3%) on 06/11/2026

    For Sale O6403214 - 237 STRATHMORE CIR, KISSIMMEE, FL 34744 55 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2278
       Built: 1999
    Monthly Fee: $18
       Tax: $4,632 (2025)
    Community: Remington Ph 1 Tr B
    Single Family


    Estimated Monthly Payment: $2,732 (change assumption)
    Mortgage ($2,328) + Fees ($18) + Taxes in 2025 ($386)


    Taxes:$4,632

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1687 PARK SIDE AVE, KISSIMMEE, FL 34744

    $436,99030 Days on yellowkey   MLS ID: S5151674

    REDUCED by $10 (0.0%) on 07/05/2026

    For Sale S5151674 - 1687 PARK SIDE AVE, KISSIMMEE, FL 34744 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022
    Monthly Fee: $11
       Tax: $7,143 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,001 (change assumption)
    Mortgage ($2,394) + Fees ($11) + Taxes in 2025 ($595)


    Taxes:$7,143

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2356 ROYALE OAKS BLVD, KISSIMMEE, FL 34744

    $415,00031 Days on yellowkey   MLS ID: S5151604

    REDUCED by $10,000 (2.4%) on 07/05/2026

    For Sale S5151604 - 2356 ROYALE OAKS BLVD, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2079
       Built: 1989   Tax: $4,158 (2025)
    Community: Royale Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $2,620 (change assumption)
    Mortgage ($2,274) + Taxes in 2025 ($347)


    Taxes:$4,158

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1425 RIVIERA DR, KISSIMMEE, FL 34744

    $944,900128 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


  • 1933 BELLKNOLL LN, KISSIMMEE, FL 34744

    $415,00040 Days on yellowkey   MLS ID: O6411567

    REDUCED by $14,000 (3.3%) on 07/02/2026

    For Sale O6411567 - 1933 BELLKNOLL LN, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2020
    Monthly Fee: $11
       Tax: $6,080 (2025)
    Community: Kindred
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,792 (change assumption)
    Mortgage ($2,274) + Fees ($11) + Taxes in 2025 ($507)


    Taxes:$6,080

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: None


  • 4406 SILVER CREEK ST, KISSIMMEE, FL 34744

    $448,00014 Days on yellowkey   MLS ID: O6418739

    For Sale O6418739 - 4406 SILVER CREEK ST, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1878
       Built: 2019
    Monthly Fee: $94
       Tax: $4,072 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Single Family


    Estimated Monthly Payment: $2,888 (change assumption)
    Mortgage ($2,455) + Fees ($94) + Taxes in 2025 ($339)


    Taxes:$4,072

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2708 PRESTWICK LN, KISSIMMEE, FL 34744

    $387,00061 Days on yellowkey   MLS ID: S5149647

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

    INCREASED by $7,000 (1.8%) on 05/22/2026

    For Sale S5149647 - 2708 PRESTWICK LN, KISSIMMEE, FL 34744 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 2004
    Monthly Fee: $92
       Tax: $7,102 (2025)
    Community: Remington Prcl M1
    Single Family


    Estimated Monthly Payment: $2,804 (change assumption)
    Mortgage ($2,120) + Fees ($92) + Taxes in 2025 ($592)


    Taxes:$7,102

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1009 CHALCEDONY ST, KISSIMMEE, FL 34744

    $315,00035 Days on yellowkey   MLS ID: O6412394

    REDUCED by $10,000 (3.1%) on 07/03/2026

    For Sale O6412394 - 1009 CHALCEDONY ST, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1683
       Built: 2010
    Monthly Fee: $170
       Tax: $3,128 (2025)
    Community: Amber Pointe
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,157 (change assumption)
    Mortgage ($1,726) + Fees ($170) + Taxes in 2025 ($261)


    Taxes:$3,128

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744

    $499,900234 Days on yellowkey   MLS ID: S5138827

    REDUCED by $15,100 (2.9%) on 06/14/2026

    For Sale S5138827 - 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3099
       Built: 2017
    Monthly Fee: $11
       Tax: $5,957 (2024)
    Community: Kindred Ph 1C
    Single Family


    Estimated Monthly Payment: $3,246 (change assumption)
    Mortgage ($2,739) + Fees ($11) + Taxes in 2024 ($496)


    Taxes:$5,957

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1740 SAINT TROPEZ CT, KISSIMMEE, FL 34744

    $320,00052 Days on yellowkey   MLS ID: O6409575

    REDUCED by $15,000 (4.5%) on 06/29/2026

    For Sale O6409575 - 1740 SAINT TROPEZ CT, KISSIMMEE, FL 34744 32 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2104
       Built: 1991
    Monthly Fee: $180
       Tax: $2,753 (2025)
    Community: Monaco Villas Ph 2
    Townhouse


    Estimated Monthly Payment: $2,163 (change assumption)
    Mortgage ($1,753) + Fees ($180) + Taxes in 2025 ($229)


    Taxes:$2,753

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2743 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $635,000129 Days on yellowkey   MLS ID: O6386876

    1 Days Off yellowkey (back on 7/3/2026)

    REDUCED by $14,900 (2.3%) on 06/26/2026

    For Sale O6386876 - 2743 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744 56 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2856
       Built: 2005
    Monthly Fee: $195
       Tax: $7,062 (2025)
    Community: Kissimmee Bay
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,263 (change assumption)
    Mortgage ($3,479) + Fees ($195) + Taxes in 2025 ($589)


    Taxes:$7,062

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 302 E DRURY AVE, KISSIMMEE, FL 34744

    $368,00039 Days on yellowkey   MLS ID: O6411839

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

    For Sale O6411839 - 302 E DRURY AVE, KISSIMMEE, FL 34744 42 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


  • 1802 BLISSFUL DR, KISSIMMEE, FL 34744

    $639,90030 Days on yellowkey   MLS ID: O6415660

    1 Days Off yellowkey (back on 6/15/2026)

    For Sale O6415660 - 1802 BLISSFUL DR, KISSIMMEE, FL 34744 61 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3407
       Built: 2021
    Monthly Fee: $7
       Tax: $10,565 (2025)
    Community: Tohoqua Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,394 (change assumption)
    Mortgage ($3,506) + Fees ($7) + Taxes in 2025 ($880)


    Taxes:$10,565

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1959 CACUTTA WAY, KISSIMMEE, FL 34744

    $387,00036 Days on yellowkey   MLS ID: S5151373

    REDUCED by $13,000 (3.3%) on 07/03/2026

    SHORT SALE S5151373 - 1959 CACUTTA WAY, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2023
    Monthly Fee: $11
       Tax: $7,033 (2025)
    Community: Kindred
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,120) + Fees ($11) + Taxes in 2025 ($586)


    Taxes:$7,033

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Harmony Middle


  • 1010 VAN LIEU ST, KISSIMMEE, FL 34744

    $318,50052 Days on yellowkey   MLS ID: O6409485

    REDUCED by $6,000 (1.8%) on 07/03/2026

    For Sale O6409485 - 1010 VAN LIEU ST, KISSIMMEE, FL 34744 12 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1062
       Built: 1986   Tax: $3,618 (2025)
    Community: Kissimmee Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,047 (change assumption)
    Mortgage ($1,745) + Taxes in 2025 ($302)


    Taxes:$3,618

    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.