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Winter Park Homes For Sale & Real Estate - 447 homes

Winter Park homes for sale are located in Seminole County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 1920 HEATHWOOD DR, WINTER PARK, FL 32792

    $370,00080 Days on yellowkey   MLS ID: O6393303

    For Sale O6393303 - 1920 HEATHWOOD DR, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1978
       Built: 1980   Tax: $4,895 (2025)
    Community: Cedar Ridge Unit 1
    Single Family


    Estimated Monthly Payment: $2,435 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($408)


    Taxes:$4,895

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 106 S INTERLACHEN AVE #518, WINTER PARK, FL 32789

    $1,899,90053 Days on yellowkey   MLS ID: O6400228

    REDUCED by $50,100 (2.6%) on 06/03/2026

    For Sale O6400228 - 106 S INTERLACHEN AVE #518, WINTER PARK, FL 32789 58 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1807
       Built: 1971   Tax: $14,974 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $11,658 (change assumption)
    Mortgage ($10,410) + Taxes in 2025 ($1,248)


    Taxes:$14,974

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1351 MAGNOLIA AVE, WINTER PARK, FL 32789

    $3,100,00043 Days on yellowkey   MLS ID: O6404105

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

    For Sale O6404105 - 1351 MAGNOLIA AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2026   Tax: $9,720 (2025)
    Community: Lake Knowles Terrace Add 02
    Single Family


    Estimated Monthly Payment: $17,796 (change assumption)
    Mortgage ($16,986) + Taxes in 2025 ($810)


    Taxes:$9,720

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $479,900310 Days on yellowkey   MLS ID: O6330690

    REDUCED by $100 (0.0%) on 06/03/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,147 (change assumption)
    Mortgage ($2,630) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 1618 INDIANA AVE, WINTER PARK, FL 32789

    $675,00061 Days on yellowkey   MLS ID: O6398673

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

    REDUCED by $10,000 (1.5%) on 05/08/2026

    For Sale O6398673 - 1618 INDIANA AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 1604
       Built: 1963   Tax: $5,477 (2025)
    Community: Lawndale
    Apartment


    Estimated Monthly Payment: $4,155 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($456)


    Taxes:$5,477

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1437 MILLER AVE, WINTER PARK, FL 32789

    $750,00044 Days on yellowkey   MLS ID: O6403858

    1 Days Off yellowkey (back on 5/3/2026)

    For Sale O6403858 - 1437 MILLER AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 2150
       Built: 1932   Tax: $6,987 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $4,692 (change assumption)
    Mortgage ($4,109) + Taxes in 2025 ($582)


    Taxes:$6,987

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1850 ASTER DR, WINTER PARK, FL 32792

    $500,00011 Days on yellowkey   MLS ID: TB8513990

    For Sale TB8513990 - 1850 ASTER DR, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1978   Tax: $1,584 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,872 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($132)


    Taxes:$1,584

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3114 HEARTLEAF PL, WINTER PARK, FL 32792

    $685,00084 Days on yellowkey   MLS ID: S5146048

    REDUCED by $14,900 (2.1%) on 06/02/2026

    For Sale S5146048 - 3114 HEARTLEAF PL, WINTER PARK, FL 32792 71 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2702
       Built: 1999
    Monthly Fee: $18
       Tax: $6,737 (2024)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,333 (change assumption)
    Mortgage ($3,753) + Fees ($18) + Taxes in 2024 ($561)


    Taxes:$6,737

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2529 WINDWARD WAY, WINTER PARK, FL 32792

    $299,00016 Days on yellowkey   MLS ID: S5150790

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

    For Sale S5150790 - 2529 WINDWARD WAY, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1977
    Monthly Fee: $99
       Tax: $332 (2025)
    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,765 (change assumption)
    Mortgage ($1,638) + Fees ($99) + Taxes in 2025 ($28)


    Taxes:$332

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1130 PARK NORTH PLACE, WINTER PARK, FL 32789

    $2,495,00079 Days on yellowkey   MLS ID: O6392394

    REDUCED by $155,000 (5.8%) on 04/22/2026

    For Sale O6392394 - 1130 PARK NORTH PLACE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4011
       Built: 1968   Tax: $9,744 (2025)
    Community: Park North
    Single Family


    Estimated Monthly Payment: $14,483 (change assumption)
    Mortgage ($13,671) + Taxes in 2025 ($812)


    Taxes:$9,744

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 610 ELLENDALE DR, WINTER PARK, FL 32792

    $399,00015 Days on yellowkey   MLS ID: O6411325

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

    For Sale O6411325 - 610 ELLENDALE DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1359
       Built: 1957   Tax: $2,321 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($193)


    Taxes:$2,321

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 126 SCOTTSDALE SQ #126, WINTER PARK, FL 32792

    $150,000176 Days on yellowkey   MLS ID: S5140472

    For Sale S5140472 - 126 SCOTTSDALE SQ #126, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1085
       Built: 1974
    Monthly Fee: $950
       Tax: $1,660 (2024)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $1,910 (change assumption)
    Mortgage ($822) + Fees ($950) + Taxes in 2024 ($138)


    Taxes:$1,660

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7001 JACKMAN BLVD, WINTER PARK, FL 32792

    $450,00029 Days on yellowkey   MLS ID: O6408371

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

    For Sale O6408371 - 7001 JACKMAN BLVD, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1482
       Built: 1977   Tax: $4,421 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,834 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($368)


    Taxes:$4,421

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792

    $1,199,00017 Days on yellowkey   MLS ID: O6411164

    For Sale O6411164 - 1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792 51 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3652
       Built: 2018
    Monthly Fee: $186
       Tax: $7,277 (2025)
    Community: Lake Florence Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,362 (change assumption)
    Mortgage ($6,570) + Fees ($186) + Taxes in 2025 ($606)


    Taxes:$7,277

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2482 ROXBURY RD, WINTER PARK, FL 32789

    $375,00036 Days on yellowkey   MLS ID: O6406443

    REDUCED by $25,000 (6.3%) on 06/02/2026

    For Sale O6406443 - 2482 ROXBURY RD, WINTER PARK, FL 32789 20 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 913
       Built: 1948   Tax: $5,020 (2025)
    Community: Glencoe
    Single Family


    Estimated Monthly Payment: $2,473 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($418)


    Taxes:$5,020

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1516 MILLER AVE, WINTER PARK, FL 32789

    $1,549,90012 Days on yellowkey   MLS ID: O6412745

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

    For Sale O6412745 - 1516 MILLER AVE, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3144
       Built: 2026   Tax: $4,868 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,898 (change assumption)
    Mortgage ($8,492) + Taxes in 2025 ($406)


    Taxes:$4,868

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7485 ALOMA PINES CT, WINTER PARK, FL 32792

    $375,00064 Days on yellowkey   MLS ID: O6398259

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

    REDUCED by $15,000 (3.8%) on 05/23/2026

    For Sale O6398259 - 7485 ALOMA PINES CT, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1787
       Built: 2017
    Monthly Fee: $407
       Tax: $4,585 (2025)
    Community: Aloma Trails
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,844 (change assumption)
    Mortgage ($2,055) + Fees ($407) + Taxes in 2025 ($382)


    Taxes:$4,585

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792

    $148,500295 Days on yellowkey   MLS ID: O6337083

    REDUCED by $500 (0.3%) on 06/01/2026

    For Sale O6337083 - 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 749
       Built: 1984
    Monthly Fee: $300
       Tax: $2,050 (2024)
    Community: Parkview Village
    Spa: No

    Condo


    Estimated Monthly Payment: $1,284 (change assumption)
    Mortgage ($814) + Fees ($300) + Taxes in 2024 ($171)


    Taxes:$2,050

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 150 KILLARNEY BAY CT #5, WINTER PARK, FL 32789

    $315,000330 Days on yellowkey   MLS ID: O6328063

    For Sale O6328063 - 150 KILLARNEY BAY CT #5, WINTER PARK, FL 32789 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1140
       Built: 1986
    Monthly Fee: $460
       Tax: $2,100 (2024)
    Community: Killarney Bay Condo
    Condo


    Estimated Monthly Payment: $2,361 (change assumption)
    Mortgage ($1,726) + Fees ($460) + Taxes in 2024 ($175)


    Taxes:$2,100

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1627 MIZELL AVE, WINTER PARK, FL 32789

    $3,300,00027 Days on yellowkey   MLS ID: O6406300

    For Sale O6406300 - 1627 MIZELL AVE, WINTER PARK, FL 32789 24 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3421
       Built: 2026   Tax: $11,211 (2025)
    Community: Sylvan Lake Shores
    Single Family


    Estimated Monthly Payment: $19,016 (change assumption)
    Mortgage ($18,082) + Taxes in 2025 ($934)


    Taxes:$11,211

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales 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 Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park 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 Winter Park 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.