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 - 289 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:
  • 2503 HASSONITE ST, KISSIMMEE, FL 34744

    $345,000166 Days on yellowkey   MLS ID: S5137504

    For Sale S5137504 - 2503 HASSONITE ST, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2018
       Built: 2007
    Monthly Fee: $170
       Tax: $1,559 (2024)
    Community: Amber Pointe
    Townhouse


    Estimated Monthly Payment: $2,190 (change assumption)
    Mortgage ($1,890) + Fees ($170) + Taxes in 2024 ($130)


    Taxes:$1,559

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744

    $530,0005 Days on yellowkey   MLS ID: S5147642

    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: $3,454 (change assumption)
    Mortgage ($2,904) + 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)


  • 1378 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $585,0005 Days on yellowkey   MLS ID: R4911041

    0 Days Off yellowkey (back on 4/18/2026)

    For Sale R4911041 - 1378 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2147
       Built: 1997   Tax: $3,637 (2025)
    Community: East Lake Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,508 (change assumption)
    Mortgage ($3,205) + Taxes in 2025 ($303)


    Taxes:$3,637

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1135 CHEROKEE DR, KISSIMMEE, FL 34744

    $375,99047 Days on yellowkey   MLS ID: S5144943

    For Sale S5144943 - 1135 CHEROKEE DR, KISSIMMEE, FL 34744 12 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1358
       Built: 1964   Tax: $1,014 (2025)
    Community: Osceola Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($2,060) + Taxes in 2025 ($85)


    Taxes:$1,014

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2035 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $424,39093 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


  • 1756 STAMEN DR, KISSIMMEE, FL 34744

    $449,90059 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)


  • 3104 MANDOLIN DR, KISSIMMEE, FL 34744

    $465,0004 Days on yellowkey   MLS ID: S5147810

    For Sale S5147810 - 3104 MANDOLIN DR, KISSIMMEE, FL 34744 76 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 2007
    Monthly Fee: $83
       Tax: $3,388 (2025)
    Community: Turnberry Resv U2
    Single Family


    Estimated Monthly Payment: $2,913 (change assumption)
    Mortgage ($2,548) + Fees ($83) + Taxes in 2025 ($282)


    Taxes:$3,388

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 2661 ELLEN AVE, KISSIMMEE, FL 34744

    $450,0002 Days on yellowkey   MLS ID: O6399716

    For Sale O6399716 - 2661 ELLEN AVE, KISSIMMEE, FL 34744 25 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1864
       Built: 1972   Tax: $5,005 (2025)
    Community: Emerald Lake Colony Unit 3
    Single Family


    Estimated Monthly Payment: $2,883 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($417)


    Taxes:$5,005

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2776 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $794,900129 Days on yellowkey   MLS ID: S5139337

    REDUCED by $24,100 (2.9%) on 04/17/2026

    For Sale S5139337 - 2776 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744 52 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3340
       Built: 2018
    Monthly Fee: $190
       Tax: $5,827 (2025)
    Community: Kissimmee Bay Rep 7
    Single Family


    Estimated Monthly Payment: $5,031 (change assumption)
    Mortgage ($4,356) + Fees ($190) + Taxes in 2025 ($486)


    Taxes:$5,827

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7 WESTCHESTER DR, KISSIMMEE, FL 34744

    $434,000335 Days on yellowkey   MLS ID: O6309992

    REDUCED by $5,000 (1.1%) on 04/16/2026

    For Sale O6309992 - 7 WESTCHESTER DR, KISSIMMEE, FL 34744 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1786
       Built: 1962   Tax: $1,988 (2024)
    Community: Fairlawn Manor
    Single Family


    Estimated Monthly Payment: $2,544 (change assumption)
    Mortgage ($2,378) + Taxes in 2024 ($166)


    Taxes:$1,988

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2761 MICHIGAN AVE, KISSIMMEE, FL 34744

    $459,00086 Days on yellowkey   MLS ID: O6375128

    REDUCED by $10,000 (2.1%) on 04/06/2026

    For Sale O6375128 - 2761 MICHIGAN AVE, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 1869
       Built: 1979   Tax: $7,282 (2025)
    Community: Lee Bel Park
    Apartment


    Estimated Monthly Payment: $3,122 (change assumption)
    Mortgage ($2,515) + Taxes in 2025 ($607)


    Taxes:$7,282

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2835 NOBLE CROW DR, KISSIMMEE, FL 34744

    $479,90040 Days on yellowkey   MLS ID: S5145312

    For Sale S5145312 - 2835 NOBLE CROW DR, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2676
       Built: 2020
    Monthly Fee: $93
       Tax: $5,079 (2025)
    Community: Marbella Ph 1
    Single Family


    Estimated Monthly Payment: $3,146 (change assumption)
    Mortgage ($2,630) + Fees ($93) + Taxes in 2025 ($423)


    Taxes:$5,079

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1719 FLOURISH AVE, KISSIMMEE, FL 34744

    $459,99962 Days on yellowkey   MLS ID: O6382782

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale O6382782 - 1719 FLOURISH AVE, KISSIMMEE, FL 34744 5 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2450
       Built: 2021
    Monthly Fee: $80
       Tax: $5,605 (2025)
    Community: Tohoqua Ph 1
    Single Family


    Estimated Monthly Payment: $3,068 (change assumption)
    Mortgage ($2,520) + Fees ($80) + Taxes in 2025 ($467)


    Taxes:$5,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744

    $489,000291 Days on yellowkey   MLS ID: S5130069

    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: $3,200 (change assumption)
    Mortgage ($2,679) + 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


  • 1325 CYPRESS ARBOR, KISSIMMEE, FL 34744

    $275,0003 Days on yellowkey   MLS ID: O6398060

    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


  • 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744

    $519,90063 Days on yellowkey   MLS ID: S5143801

    For Sale S5143801 - 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2727
       Built: 2023
    Monthly Fee: $130
       Tax: $7,208 (2025)
    Community: Creekside At Boggy Creek Ph 3
    Single Family


    Estimated Monthly Payment: $3,579 (change assumption)
    Mortgage ($2,849) + Fees ($130) + Taxes in 2025 ($601)


    Taxes:$7,208

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2507 WINNERS CIR, KISSIMMEE, FL 34744

    $549,0009 Days on yellowkey   MLS ID: S5147254

    1 Days Off yellowkey (back on 4/18/2026)

    For Sale S5147254 - 2507 WINNERS CIR, KISSIMMEE, FL 34744 98 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1914
       Built: 1999   Tax: $2,483 (2025)
    Community: D S Estates
    Single Family


    Estimated Monthly Payment: $3,215 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($207)


    Taxes:$2,483

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $457,00051 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


  • 1516 PINE ISLAND RD, KISSIMMEE, FL 34744

    $875,00023 Days on yellowkey   MLS ID: S5145674

    For Sale S5145674 - 1516 PINE ISLAND RD, KISSIMMEE, FL 34744 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2613
       Built: 2026   Tax: $1,385 (2025)
    Community: Regal Point Estates Unit 1
    Single Family


    Estimated Monthly Payment: $4,910 (change assumption)
    Mortgage ($4,794) + Taxes in 2025 ($115)


    Taxes:$1,385

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 216 MAGICAL WAY, KISSIMMEE, FL 34744

    $359,000Listed 04/17/2026 10:49PM   MLS ID: O6396457

    For Sale O6396457 - 216 MAGICAL WAY, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1832
       Built: 2005
    Monthly Fee: $127
       Tax: $4,782 (2025)
    Community: Magic Landings
    Single Family


    Estimated Monthly Payment: $2,493 (change assumption)
    Mortgage ($1,967) + Fees ($127) + Taxes in 2025 ($399)


    Taxes:$4,782

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John 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.