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Homes for Sale Near Maitland Middle in Winter Park - 87 homes

Maitland Middle is an Middle School in Orange County. Find homes for sale close to Maitland Middle. Our REALTORS® can assist you in your search for Maitland Middle, Winter Park nearby homes.

Location: Winter Park

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  • 1830 EDWIN BLVD, WINTER PARK, FL 32789

    $639,90060 Days on yellowkey   MLS ID: O6400055

    REDUCED by $9,900 (1.5%) on 05/28/2026

    For Sale O6400055 - 1830 EDWIN BLVD, WINTER PARK, FL 32789 48 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1287
       Built: 1957   Tax: $3,955 (2025)
    Community: Campo Bello
    Single Family


    Estimated Monthly Payment: $3,836 (change assumption)
    Mortgage ($3,506) + Taxes in 2025 ($330)


    Taxes:$3,955

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1800 MAGNOLIA AVE, WINTER PARK, FL 32789

    $995,00091 Days on yellowkey   MLS ID: NS1087637

    REDUCED by $5,000 (0.5%) on 06/12/2026

    For Sale NS1087637 - 1800 MAGNOLIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2431
       Built: 1996   Tax: $11,730 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,429 (change assumption)
    Mortgage ($5,452) + Taxes in 2025 ($978)


    Taxes:$11,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2974 CHANTILLY AVE, WINTER PARK, FL 32789

    $550,0009 Days on yellowkey   MLS ID: O6412851

    For Sale O6412851 - 2974 CHANTILLY AVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1433
       Built: 1960   Tax: $1,178 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $3,112 (change assumption)
    Mortgage ($3,014) + Taxes in 2025 ($98)


    Taxes:$1,178

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $1,900,00082 Days on yellowkey   MLS ID: O6393117

    REDUCED by $89,000 (4.5%) on 06/05/2026

    For Sale O6393117 - 785 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2964
       Built: 2026   Tax: $9,172 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,175 (change assumption)
    Mortgage ($10,411) + Taxes in 2025 ($764)


    Taxes:$9,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 731 BONGART ROAD, WINTER PARK, FL 32792

    $499,00039 Days on yellowkey   MLS ID: O6406004

    For Sale O6406004 - 731 BONGART ROAD, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,227 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,00087 Days on yellowkey   MLS ID: O6391825

    For Sale O6391825 - 914 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3617
       Built: 2026
    Monthly Fee: $372
       Tax: $10,000 (2025)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,589 (change assumption)
    Mortgage ($10,383) + Fees ($372) + Taxes in 2025 ($833)


    Taxes:$10,000

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 948 POINCIANA LN, WINTER PARK, FL 32789

    $2,899,900154 Days on yellowkey   MLS ID: O6372165

    REDUCED by $274,100 (8.6%) on 06/13/2026

    For Sale O6372165 - 948 POINCIANA LN, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3676
       Built: 2001   Tax: $19,753 (2025)
    Community: Maitland Shores First Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,536 (change assumption)
    Mortgage ($15,889) + Taxes in 2025 ($1,646)


    Taxes:$19,753

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1220 WOODMERE DR, WINTER PARK, FL 32789

    $1,700,0003 Days on yellowkey   MLS ID: O6415611

    For Sale O6415611 - 1220 WOODMERE DR, WINTER PARK, FL 32789 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2815
       Built: 1996   Tax: $7,845 (2025)
    Community: Woodmere Terrace Rep
    Single Family


    Estimated Monthly Payment: $9,969 (change assumption)
    Mortgage ($9,315) + Taxes in 2025 ($654)


    Taxes:$7,845

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789

    $1,795,00014 Days on yellowkey   MLS ID: O6412554

    For Sale O6412554 - 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2023   Tax: $18,393 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $11,368 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,533)


    Taxes:$18,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1441 CARDINAL CT, WINTER PARK, FL 32789

    $4,285,00061 Days on yellowkey   MLS ID: O6399395

    For Sale O6399395 - 1441 CARDINAL CT, WINTER PARK, FL 32789 85 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4066
       Built: 2022   Tax: $47,740 (2025)
    Community: Winflor Court
    Spa: No

    Single Family


    Estimated Monthly Payment: $27,457 (change assumption)
    Mortgage ($23,479) + Taxes in 2025 ($3,978)


    Taxes:$47,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 649 N PARK AVE, WINTER PARK, FL 32789

    $3,500,00013 Days on yellowkey   MLS ID: O6411141

    For Sale O6411141 - 649 N PARK AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3180
       Built: 2019
    Monthly Fee: $948
       Tax: $22,599 (2025)
    Community: Park Hill
    Townhouse


    Estimated Monthly Payment: $22,009 (change assumption)
    Mortgage ($19,178) + Fees ($948) + Taxes in 2025 ($1,883)


    Taxes:$22,599

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,665,00032 Days on yellowkey   MLS ID: O6401352

    For Sale O6401352 - 2430 CHANTILLY AVE, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 2026   Tax: $4,730 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,517 (change assumption)
    Mortgage ($9,123) + Taxes in 2025 ($394)


    Taxes:$4,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,070,00046 Days on yellowkey   MLS ID: O6402502

    REDUCED by $30,000 (2.7%) on 06/10/2026

    For Sale O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789 45 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 1973   Tax: $3,590 (2025)
    Community: Lake Knowles Terrace
    Single Family


    Estimated Monthly Payment: $6,162 (change assumption)
    Mortgage ($5,863) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1150 VIA SALERNO, WINTER PARK, FL 32789

    $4,195,000352 Days on yellowkey   MLS ID: O6321143

    REDUCED by $555,000 (11.7%) on 04/25/2026

    For Sale O6321143 - 1150 VIA SALERNO, WINTER PARK, FL 32789 62 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3850
       Built: 2025   Tax: $10,158 (2024)
    Community: Cloister Grove Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $23,832 (change assumption)
    Mortgage ($22,986) + Taxes in 2024 ($847)


    Taxes:$10,158

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 950 ENCLAVE PL, WINTER PARK, FL 32792

    $2,125,00018 Days on yellowkey   MLS ID: O6410963

    For Sale O6410963 - 950 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3797
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,593 (change assumption)
    Mortgage ($11,644) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00026 Days on yellowkey   MLS ID: O6408090

    For Sale O6408090 - 938 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3865
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,450 (change assumption)
    Mortgage ($11,501) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 910 ENCLAVE PL, WINTER PARK, FL 32792

    $1,899,00032 Days on yellowkey   MLS ID: O6406803

    For Sale O6406803 - 910 ENCLAVE PL, WINTER PARK, FL 32792 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3620
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,354 (change assumption)
    Mortgage ($10,405) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 930 ENCLAVE PL, WINTER PARK, FL 32792

    $2,050,00032 Days on yellowkey   MLS ID: O6403032

    For Sale O6403032 - 930 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3813
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,182 (change assumption)
    Mortgage ($11,233) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 901 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00087 Days on yellowkey   MLS ID: O6383602

    For Sale O6383602 - 901 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2738
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 905 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00087 Days on yellowkey   MLS ID: O6383679

    For Sale O6383679 - 905 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle




Why Bother Searching Elsewhere for Homes For Sale and Real Estate nearby Maitland Middle?

Home, townhome, condo, villa, and other listing sales data closeby Maitland Middle is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on homes for sale nearby Maitland Middle, Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park homes near Maitland Middle. 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 listings that are close to Maitland Middle.



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.