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Winter Park Homes For Sale & Real Estate - 444 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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  • 1437 MILLER AVE, WINTER PARK, FL 32789

    $750,00030 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


  • 1760 LEGION DR, WINTER PARK, FL 32789

    $2,295,000101 Days on yellowkey   MLS ID: O6383603

    For Sale O6383603 - 1760 LEGION DR, WINTER PARK, FL 32789 66 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4392
       Built: 1964   Tax: $13,622 (2025)
    Community: Green Oaks Rep
    Single Family


    Estimated Monthly Payment: $13,710 (change assumption)
    Mortgage ($12,575) + Taxes in 2025 ($1,135)


    Taxes:$13,622

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2500 LEE RD #122, WINTER PARK, FL 32789

    $179,00088 Days on yellowkey   MLS ID: O6384082

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

    For Sale O6384082 - 2500 LEE RD #122, WINTER PARK, FL 32789 25 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969   Tax: $428 (2024)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,016 (change assumption)
    Mortgage ($981) + Taxes in 2024 ($36)


    Taxes:$428

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,00095 Days on yellowkey   MLS ID: S5144547

    For Sale S5144547 - 2648 GALLIANO CIR, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1550
       Built: 2004
    Monthly Fee: $175
       Tax: $4,736 (2024)
    Community: Vistas At Lake Howell
    Single Family


    Estimated Monthly Payment: $2,515 (change assumption)
    Mortgage ($1,945) + Fees ($175) + Taxes in 2024 ($395)


    Taxes:$4,736

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 278 SCOTTSDALE SQ #278, WINTER PARK, FL 32792

    $99,000101 Days on yellowkey   MLS ID: O6383638

    For Sale O6383638 - 278 SCOTTSDALE SQ #278, WINTER PARK, FL 32792 27 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1974
    Monthly Fee: $880
       Tax: $1,552 (2025)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $1,552 (change assumption)
    Mortgage ($542) + Fees ($880) + Taxes in 2025 ($129)


    Taxes:$1,552

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2922 REEF KNOT PL, WINTER PARK, FL 32792

    $1,149,000356 Days on yellowkey   MLS ID: O6316445

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

    For Sale O6316445 - 2922 REEF KNOT PL, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3153
       Built: 2019
    Monthly Fee: $186
       Tax: $10,521 (2024)
    Community: Lake Florence Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,358 (change assumption)
    Mortgage ($6,296) + Fees ($186) + Taxes in 2024 ($877)


    Taxes:$10,521

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2627 AMBERGATE RD, WINTER PARK, FL 32792

    $510,0001173 Days on yellowkey   MLS ID: O6093816

    For Sale O6093816 - 2627 AMBERGATE RD, WINTER PARK, FL 32792 19 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1805
       Built: 1959   Tax: $4,750 (2022)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,190 (change assumption)
    Mortgage ($2,794) + Taxes in 2022 ($396)


    Taxes:$4,750

    Elementary School: None

    High School: None

    Tax Year: 2022

    Middle School: None


  • 1351 MAGNOLIA AVE, WINTER PARK, FL 32789

    $3,100,00029 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


  • 2237 WOODCREST DR, WINTER PARK, FL 32792

    $490,00029 Days on yellowkey   MLS ID: O6404115

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

    For Sale O6404115 - 2237 WOODCREST DR, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1492
       Built: 1959   Tax: $1,919 (2025)
    Community: Kenilworth Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,845 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($160)


    Taxes:$1,919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 200 SAINT ANDREWS BLVD #315, WINTER PARK, FL 32792

    $169,000106 Days on yellowkey   MLS ID: V4947283

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

    For Sale V4947283 - 200 SAINT ANDREWS BLVD #315, WINTER PARK, FL 32792 43 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 793
       Built: 1970
    Monthly Fee: $451
       Tax: $873 (2024)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,450 (change assumption)
    Mortgage ($926) + Fees ($451) + Taxes in 2024 ($73)


    Taxes:$873

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00064 Days on yellowkey   MLS ID: O6394012

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

    For Sale O6394012 - 150 DANA WAY, WINTER PARK, FL 32789 81 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4451
       Built: 2026   Tax: $14,010 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,983 (change assumption)
    Mortgage ($20,816) + Taxes in 2025 ($1,168)


    Taxes:$14,010

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1781 INDIANA AVE #A, WINTER PARK, FL 32789

    $545,000108 Days on yellowkey   MLS ID: O6381195

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

    REDUCED by $20,000 (3.5%) on 04/14/2026

    For Sale O6381195 - 1781 INDIANA AVE #A, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 2008
    Monthly Fee: $464
       Tax: $6,026 (2024)
    Community: Las Casas De Indiana
    Townhouse


    Estimated Monthly Payment: $3,952 (change assumption)
    Mortgage ($2,986) + Fees ($464) + Taxes in 2024 ($502)


    Taxes:$6,026

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1354 INDIANA AVE, WINTER PARK, FL 32789

    $589,90086 Days on yellowkey   MLS ID: O6387500

    For Sale O6387500 - 1354 INDIANA AVE, WINTER PARK, FL 32789 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1269
       Built: 1947   Tax: $5,352 (2024)
    Community: Metzingers Add
    Single Family


    Estimated Monthly Payment: $3,678 (change assumption)
    Mortgage ($3,232) + Taxes in 2024 ($446)


    Taxes:$5,352

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2220 FAIRGLENN WAY, WINTER PARK, FL 32792

    $649,90043 Days on yellowkey   MLS ID: O6399993

    REDUCED by $25,000 (3.7%) on 04/30/2026

    For Sale O6399993 - 2220 FAIRGLENN WAY, WINTER PARK, FL 32792 54 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 1986
    Monthly Fee: $53
       Tax: $3,357 (2025)
    Community: Quail Run
    Single Family


    Estimated Monthly Payment: $3,894 (change assumption)
    Mortgage ($3,561) + Fees ($53) + Taxes in 2025 ($280)


    Taxes:$3,357

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1832 E CHERYL DR, WINTER PARK, FL 32792

    $439,99536 Days on yellowkey   MLS ID: O6402209

    0 Days Off yellowkey (back on 4/30/2026)

    INCREASED by $10,000 (2.3%) on 04/27/2026

    For Sale O6402209 - 1832 E CHERYL DR, WINTER PARK, FL 32792 22 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1983
    Monthly Fee: $8
       Tax: $1,847 (2024)
    Community: Carolyn Estates
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,411) + Fees ($8) + Taxes in 2024 ($154)


    Taxes:$1,847

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 100 S INTERLACHEN AVE #101, WINTER PARK, FL 32789

    $1,299,000100 Days on yellowkey   MLS ID: O6382597

    For Sale O6382597 - 100 S INTERLACHEN AVE #101, WINTER PARK, FL 32789 53 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1734
       Built: 1971   Tax: $9,362 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $7,898 (change assumption)
    Mortgage ($7,118) + Taxes in 2025 ($780)


    Taxes:$9,362

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,185,99931 Days on yellowkey   MLS ID: O6402984

    For Sale O6402984 - 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789 37 photos

    Bed: 6   Bath: 0.0
    Liv Area Sq Ft: 2282
       Built: 2015   Tax: $5,170 (2025)
    Community: Morseland Sub
    Apartment


    Estimated Monthly Payment: $6,929 (change assumption)
    Mortgage ($6,498) + Taxes in 2025 ($431)


    Taxes:$5,170

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 420 OHIO ST, WINTER PARK, FL 32789

    $1,360,00032 Days on yellowkey   MLS ID: O6399541

    For Sale O6399541 - 420 OHIO ST, WINTER PARK, FL 32789 8 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3735
       Built: 2026   Tax: $1,281 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $7,559 (change assumption)
    Mortgage ($7,452) + Taxes in 2025 ($107)


    Taxes:$1,281

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000316 Days on yellowkey   MLS ID: O6325192

    For Sale O6325192 - 501 LAKEVIEW AVE, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3253
       Built: 2026   Tax: $2,820 (2024)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($7,616) + Taxes in 2024 ($235)


    Taxes:$2,820

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 7484 CANFORD CT #8, WINTER PARK, FL 32792

    $250,00033 Days on yellowkey   MLS ID: O6402492

    For Sale O6402492 - 7484 CANFORD CT #8, WINTER PARK, FL 32792 25 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1578
       Built: 1974   Tax: $2,121 (2025)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,547 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($177)


    Taxes:$2,121

    Elementary School: Cheney 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.