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 - 343 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:
  • 1556 HEATHER WAY, KISSIMMEE, FL 34744

    $320,00029 Days on yellowkey   MLS ID: O6404040

    REDUCED by $20,000 (5.9%) on 05/30/2026

    For Sale O6404040 - 1556 HEATHER WAY, KISSIMMEE, FL 34744 5 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1577
       Built: 1976   Tax: $3,121 (2025)
    Community: Heather Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,013 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($260)


    Taxes:$3,121

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2733 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744

    $392,01060 Days on yellowkey   MLS ID: O6395315

    For Sale O6395315 - 2733 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744 33 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 2025
    Monthly Fee: $136
       Tax: $3,086 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,541 (change assumption)
    Mortgage ($2,148) + Fees ($136) + Taxes in 2025 ($257)


    Taxes:$3,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2035 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $424,390135 Days on yellowkey   MLS ID: O6374311

    REDUCED by $26,150 (5.8%) on 04/08/2026

    For Sale O6374311 - 2035 SPRING SHOWER CIR, KISSIMMEE, FL 34744 23 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2018
       Built: 2026
    Monthly Fee: $128
       Tax: $3,007 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,704 (change assumption)
    Mortgage ($2,325) + Fees ($128) + Taxes in 2025 ($251)


    Taxes:$3,007

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2015 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $412,000324 Days on yellowkey   MLS ID: S5130256

    For Sale S5130256 - 2015 SPRING SHOWER CIR, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2054
       Built: 2022
    Monthly Fee: $128
       Tax: $7,088 (2024)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $2,976 (change assumption)
    Mortgage ($2,257) + Fees ($128) + Taxes in 2024 ($591)


    Taxes:$7,088

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2824 NOBLE CROW DR, KISSIMMEE, FL 34744

    $580,00023 Days on yellowkey   MLS ID: S5149494

    For Sale S5149494 - 2824 NOBLE CROW DR, KISSIMMEE, FL 34744 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2676
       Built: 2020
    Monthly Fee: $93
       Tax: $6,717 (2025)
    Community: Marbella Ph 1
    Single Family


    Estimated Monthly Payment: $3,831 (change assumption)
    Mortgage ($3,178) + Fees ($93) + Taxes in 2025 ($560)


    Taxes:$6,717

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744

    $650,00064 Days on yellowkey   MLS ID: O6393234

    REDUCED by $25,000 (3.7%) on 05/11/2026

    For Sale O6393234 - 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744 47 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3267
       Built: 2014
    Monthly Fee: $111
       Tax: $4,883 (2025)
    Community: North Point Ph Ic
    Single Family


    Estimated Monthly Payment: $4,079 (change assumption)
    Mortgage ($3,562) + Fees ($111) + Taxes in 2025 ($407)


    Taxes:$4,883

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2661 AMES HAVEN RD, KISSIMMEE, FL 34744

    $425,83087 Days on yellowkey   MLS ID: S5145125

    REDUCED by $13,170 (3.0%) on 05/28/2026

    For Sale S5145125 - 2661 AMES HAVEN RD, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1866
       Built: 1984   Tax: $4,502 (2025)
    Community: Emerald Lake Colony Unit 1
    Single Family


    Estimated Monthly Payment: $2,708 (change assumption)
    Mortgage ($2,333) + Taxes in 2025 ($375)


    Taxes:$4,502

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2540 WINNERS CIR, KISSIMMEE, FL 34744

    $699,000100 Days on yellowkey   MLS ID: O6382446

    REDUCED by $26,000 (3.6%) on 05/28/2026

    For Sale O6382446 - 2540 WINNERS CIR, KISSIMMEE, FL 34744 54 photos

    Bed: 4   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 3246
       Built: 2000   Tax: $3,688 (2025)
    Community: Winners Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,137 (change assumption)
    Mortgage ($3,830) + Taxes in 2025 ($307)


    Taxes:$3,688

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 831 NEPTUNE POINTE LN, KISSIMMEE, FL 34744

    $585,00019 Days on yellowkey   MLS ID: S5149687

    For Sale S5149687 - 831 NEPTUNE POINTE LN, KISSIMMEE, FL 34744 45 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3609
       Built: 2005
    Monthly Fee: $79
       Tax: $2,354 (2025)
    Community: Neptune Pointe
    Single Family


    Estimated Monthly Payment: $3,481 (change assumption)
    Mortgage ($3,205) + Fees ($79) + Taxes in 2025 ($196)


    Taxes:$2,354

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 237 STRATHMORE CIR, KISSIMMEE, FL 34744

    $435,00026 Days on yellowkey   MLS ID: O6403214

    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: $2,787 (change assumption)
    Mortgage ($2,384) + Fees ($18) + Taxes in 2025 ($386)


    Taxes:$4,632

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1720 FULFILLMENT DR, KISSIMMEE, FL 34744

    $400,00037 Days on yellowkey   MLS ID: O6401021

    REDUCED by $20,000 (4.8%) on 05/27/2026

    For Sale O6401021 - 1720 FULFILLMENT DR, KISSIMMEE, FL 34744 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2044
       Built: 2022
    Monthly Fee: $10
       Tax: $7,447 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,822 (change assumption)
    Mortgage ($2,192) + Fees ($10) + Taxes in 2025 ($621)


    Taxes:$7,447

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $440,00058 Days on yellowkey   MLS ID: O6395467

    For Sale O6395467 - 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 32 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


  • 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744

    $474,999333 Days on yellowkey   MLS ID: S5130069

    REDUCED by $14,001 (2.9%) on 05/26/2026

    For Sale S5130069 - 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2251
       Built: 2012
    Monthly Fee: $112
       Tax: $4,907 (2024)
    Community: North Point Ph 1A
    Single Family


    Estimated Monthly Payment: $3,124 (change assumption)
    Mortgage ($2,603) + Fees ($112) + Taxes in 2024 ($409)


    Taxes:$4,907

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 1632 REGAL COVE CT, KISSIMMEE, FL 34744

    $1,099,000262 Days on yellowkey   MLS ID: S5134100

    REDUCED by $500 (0.0%) on 05/27/2026

    For Sale S5134100 - 1632 REGAL COVE CT, KISSIMMEE, FL 34744 76 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4621
       Built: 1993
    Monthly Fee: $100
       Tax: $10,804 (2024)
    Community: Regal Cove
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,022 (change assumption)
    Mortgage ($6,022) + Fees ($100) + Taxes in 2024 ($900)


    Taxes:$10,804

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2273 SOUTHBURY DRIVE, KISSIMMEE, FL 34744

    $376,490Listed 05/30/2026 12:20PM   MLS ID: O6412192

    For Sale O6412192 - 2273 SOUTHBURY DRIVE, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $161
       Tax: $1,920 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,384 (change assumption)
    Mortgage ($2,063) + Fees ($161) + Taxes in 2025 ($160)


    Taxes:$1,920

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2810 HILLIARD ISLE RD, KISSIMMEE, FL 34744

    $509,0009 Days on yellowkey   MLS ID: O6409970

    For Sale O6409970 - 2810 HILLIARD ISLE RD, KISSIMMEE, FL 34744 55 photos

    Bed: 3   Bath: 2.0   Gar: 4
    Liv Area Sq Ft: 1396
       Built: 1983   Tax: $6,645 (2025)
    Community: Valencia Woods
    Single Family


    Estimated Monthly Payment: $3,343 (change assumption)
    Mortgage ($2,789) + Taxes in 2025 ($554)


    Taxes:$6,645

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 3078 SANGRIA ST, KISSIMMEE, FL 34744

    $390,00028 Days on yellowkey   MLS ID: O6404323

    1 Days Off yellowkey (back on 5/30/2026)

    For Sale O6404323 - 3078 SANGRIA ST, KISSIMMEE, FL 34744 10 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2017
    Monthly Fee: $160
       Tax: $7,059 (2025)
    Community: Villa Sol Village 4 Rep
    Single Family


    Estimated Monthly Payment: $2,885 (change assumption)
    Mortgage ($2,137) + Fees ($160) + Taxes in 2025 ($588)


    Taxes:$7,059

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744

    $627,110Listed 05/29/2026 9:28PM   MLS ID: O6412075

    For Sale O6412075 - 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744 30 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)


  • 2747 CALLAWAY LN, KISSIMMEE, FL 34744

    $400,0001 Day on yellowkey   MLS ID: O6411888

    For Sale O6411888 - 2747 CALLAWAY LN, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1639
       Built: 2005
    Monthly Fee: $78
       Tax: $3,420 (2025)
    Community: Remington Prcl M1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,555 (change assumption)
    Mortgage ($2,192) + Fees ($78) + Taxes in 2025 ($285)


    Taxes:$3,420

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 3013 MANDOLIN DR, KISSIMMEE, FL 34744

    $439,0001 Day on yellowkey   MLS ID: O6411560

    For Sale O6411560 - 3013 MANDOLIN DR, KISSIMMEE, FL 34744 58 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2005
    Monthly Fee: $76
       Tax: $5,071 (2025)
    Community: Turnberry Reserve Unit 1
    Single Family


    Estimated Monthly Payment: $2,904 (change assumption)
    Mortgage ($2,405) + Fees ($76) + Taxes in 2025 ($423)


    Taxes:$5,071

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle




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.