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Winter Park Homes For Sale & Real Estate - 438 homes

Winter Park homes for sale are located in Orange 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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  • 1741 MIZELL AVE, WINTER PARK, FL 32789

    $1,050,00053 Days on yellowkey   MLS ID: O6410059

    REDUCED by $45,000 (4.1%) on 06/26/2026

    For Sale O6410059 - 1741 MIZELL AVE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2015
       Built: 1982   Tax: $11,682 (2025)
    Community: Lake Monte Sub
    Single Family


    Estimated Monthly Payment: $6,727 (change assumption)
    Mortgage ($5,753) + Taxes in 2025 ($974)


    Taxes:$11,682

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1500 GAY RD #17D, WINTER PARK, FL 32789

    $249,90057 Days on yellowkey   MLS ID: O6408516

    REDUCED by $10,000 (3.8%) on 07/08/2026

    For Sale O6408516 - 1500 GAY RD #17D, WINTER PARK, FL 32789 38 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1972   Tax: $3,244 (2025)
    Community: Chateaux Du Lac
    Spa: No

    Condo


    Estimated Monthly Payment: $1,640 (change assumption)
    Mortgage ($1,369) + Taxes in 2025 ($270)


    Taxes:$3,244

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 446 MELROSE AVE, WINTER PARK, FL 32789

    $1,625,00078 Days on yellowkey   MLS ID: O6402113

    REDUCED by $70,000 (4.1%) on 06/18/2026

    For Sale O6402113 - 446 MELROSE AVE, WINTER PARK, FL 32789 39 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2640
       Built: 1987   Tax: $20,217 (2025)
    Community: Virginia Heights Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,589 (change assumption)
    Mortgage ($8,904) + Taxes in 2025 ($1,685)


    Taxes:$20,217

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1750 CAROLLEE LANE, WINTER PARK, FL 32789

    $1,820,000116 Days on yellowkey   MLS ID: O6391179

    REDUCED by $70,000 (3.7%) on 05/26/2026

    For Sale O6391179 - 1750 CAROLLEE LANE, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3249
       Built: 2012   Tax: $24,658 (2025)
    Community: Green Terrace V/140 Lot 3 Blk B
    Single Family


    Estimated Monthly Payment: $12,027 (change assumption)
    Mortgage ($9,972) + Taxes in 2025 ($2,055)


    Taxes:$24,658

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2625 PARK PLACE DR, WINTER PARK, FL 32789

    $1,799,00025 Days on yellowkey   MLS ID: O6413031

    REDUCED by $151,000 (7.7%) on 07/09/2026

    For Sale O6413031 - 2625 PARK PLACE DR, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2002
    Monthly Fee: $146
       Tax: $9,695 (2025)
    Community: Winter Park Place 45/148
    Single Family


    Estimated Monthly Payment: $10,811 (change assumption)
    Mortgage ($9,857) + Fees ($146) + Taxes in 2025 ($808)


    Taxes:$9,695

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,429,00034 Days on yellowkey   MLS ID: O6415098

    For Sale O6415098 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 38 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2351
       Built: 2025   Tax: $5,773 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,311 (change assumption)
    Mortgage ($7,830) + Taxes in 2025 ($481)


    Taxes:$5,773

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2032 KIMBRACE PL, WINTER PARK, FL 32792

    $1,988,88835 Days on yellowkey   MLS ID: O6414862

    REDUCED by $200,000 (9.1%) on 06/30/2026

    For Sale O6414862 - 2032 KIMBRACE PL, WINTER PARK, FL 32792 83 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3382
       Built: 2021   Tax: $16,035 (2025)
    Community: Kenilworth Shores Sec 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,234 (change assumption)
    Mortgage ($10,898) + Taxes in 2025 ($1,336)


    Taxes:$16,035

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 715 S RANGER BLVD, WINTER PARK, FL 32792

    $695,00049 Days on yellowkey   MLS ID: O6410899

    For Sale O6410899 - 715 S RANGER BLVD, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2312
       Built: 1967
    Monthly Fee: $4
       Tax: $2,773 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,043 (change assumption)
    Mortgage ($3,808) + Fees ($4) + Taxes in 2025 ($231)


    Taxes:$2,773

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 622 PENN PL, WINTER PARK, FL 32789

    $1,895,00054 Days on yellowkey   MLS ID: TB8511228

    For Sale TB8511228 - 622 PENN PL, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2767
       Built: 2001
    Monthly Fee: $222
       Tax: $12,624 (2025)
    Community: Pennsylvania Place Rep
    Single Family


    Estimated Monthly Payment: $11,657 (change assumption)
    Mortgage ($10,383) + Fees ($222) + Taxes in 2025 ($1,052)


    Taxes:$12,624

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,040,00075 Days on yellowkey   MLS ID: O6402502

    REDUCED by $30,000 (2.8%) on 07/10/2026

    For Sale O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789 50 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: $5,998 (change assumption)
    Mortgage ($5,698) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2501 WINTER PARK RD, WINTER PARK, FL 32789

    $1,649,000132 Days on yellowkey   MLS ID: O6384756

    REDUCED by $41,000 (2.4%) on 05/14/2026

    For Sale O6384756 - 2501 WINTER PARK RD, WINTER PARK, FL 32789 63 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3304
       Built: 2014   Tax: $10,938 (2024)
    Community: Parklando #3
    Single Family


    Estimated Monthly Payment: $9,947 (change assumption)
    Mortgage ($9,035) + Taxes in 2024 ($912)


    Taxes:$10,938

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: None


  • 151 N ORLANDO AVE ##115, WINTER PARK, FL 32789

    $290,000224 Days on yellowkey   MLS ID: O6362403

    REDUCED by $8,000 (2.7%) on 06/28/2026

    For Sale O6362403 - 151 N ORLANDO AVE ##115, WINTER PARK, FL 32789 22 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 710
       Built: 1960   Tax: $2,965 (2025)
    Community: Lake Killarney Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,836 (change assumption)
    Mortgage ($1,589) + Taxes in 2025 ($247)


    Taxes:$2,965

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2803 RIDDLE DR, WINTER PARK, FL 32789

    $589,0004 Days on yellowkey   MLS ID: O6423829

    For Sale O6423829 - 2803 RIDDLE DR, WINTER PARK, FL 32789 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1637
       Built: 1955   Tax: $6,477 (2025)
    Community: Fairshores Place
    Single Family


    Estimated Monthly Payment: $3,767 (change assumption)
    Mortgage ($3,227) + Taxes in 2025 ($540)


    Taxes:$6,477

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 5781 SHALE CT, WINTER PARK, FL 32792

    $320,0008 Days on yellowkey   MLS ID: O6422583

    For Sale O6422583 - 5781 SHALE CT, WINTER PARK, FL 32792 46 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1086
       Built: 1985
    Monthly Fee: $69
       Tax: $2,096 (2025)
    Community: Aloma Park
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $1,997 (change assumption)
    Mortgage ($1,753) + Fees ($69) + Taxes in 2025 ($175)


    Taxes:$2,096

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1411 MILLER AVE, WINTER PARK, FL 32789

    $899,00028 Days on yellowkey   MLS ID: O6416926

    For Sale O6416926 - 1411 MILLER AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1824
       Built: 2023
    Monthly Fee: $200
       Tax: $8,005 (2025)
    Community: H Vanwies Sub
    Townhouse


    Estimated Monthly Payment: $5,793 (change assumption)
    Mortgage ($4,926) + Fees ($200) + Taxes in 2025 ($667)


    Taxes:$8,005

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792

    $524,99034 Days on yellowkey   MLS ID: O6414677

    REDUCED by $10,010 (1.9%) on 07/11/2026

    For Sale O6414677 - 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1964   Tax: $6,000 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,377 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($500)


    Taxes:$6,000

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 102 BELL PL, WINTER PARK, FL 32792

    $1,399,00091 Days on yellowkey   MLS ID: O6398118

    For Sale O6398118 - 102 BELL PL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2025   Tax: $4,224 (2025)
    Community: Eastgate Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,399,500266 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,400 (3.5%) on 07/11/2026

    For Sale O6354269 - 607 ELLEN DR, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2025
    Monthly Fee: $76
       Tax: $4,224 (2024)
    Community: Lake Killarney Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,096 (change assumption)
    Mortgage ($7,668) + Fees ($76) + Taxes in 2024 ($352)


    Taxes:$4,224

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792

    $450,00011 Days on yellowkey   MLS ID: O6422142

    For Sale O6422142 - 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1525
       Built: 1984   Tax: $2,369 (2025)
    Community: Springview
    Single Family


    Estimated Monthly Payment: $2,663 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($197)


    Taxes:$2,369

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2521 GALLIANO CIR, WINTER PARK, FL 32792

    $360,00020 Days on yellowkey   MLS ID: O6419329

    For Sale O6419329 - 2521 GALLIANO CIR, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1682
       Built: 2003
    Monthly Fee: $175
       Tax: $4,532 (2025)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,525 (change assumption)
    Mortgage ($1,973) + Fees ($175) + Taxes in 2025 ($378)


    Taxes:$4,532

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla 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.