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Winter Park Homes For Sale & Real Estate - 436 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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  • WINTER PARK, FL 32792

    $430,00098 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2412 CHANTILLY AVE, WINTER PARK, FL 32789

    $2,394,500127 Days on yellowkey   MLS ID: O6381552

    0 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $500 (0.0%) on 04/20/2026

    For Sale O6381552 - 2412 CHANTILLY AVE, WINTER PARK, FL 32789 61 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 4506
       Built: 2026   Tax: $4,779 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $13,518 (change assumption)
    Mortgage ($13,120) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4348 STEED TER, WINTER PARK, FL 32792

    $824,00041 Days on yellowkey   MLS ID: O6406018

    0 Days Off yellowkey (back on 5/26/2026)

    For Sale O6406018 - 4348 STEED TER, WINTER PARK, FL 32792 74 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3040
       Built: 1989
    Monthly Fee: $29
       Tax: $3,652 (2024)
    Community: Kings Cove
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,848 (change assumption)
    Mortgage ($4,515) + Fees ($29) + Taxes in 2024 ($304)


    Taxes:$3,652

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 560 OLOLU DR, WINTER PARK, FL 32789

    $925,000261 Days on yellowkey   MLS ID: O6344540

    REDUCED by $24,000 (2.5%) on 05/24/2026

    For Sale O6344540 - 560 OLOLU DR, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1086
       Built: 1953   Tax: $8,617 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $5,786 (change assumption)
    Mortgage ($5,068) + Taxes in 2024 ($718)


    Taxes:$8,617

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 650 DIXIE PKWY, WINTER PARK, FL 32789

    $4,250,00031 Days on yellowkey   MLS ID: O6408708

    5 Days Off yellowkey (back on 5/26/2026)

    For Sale O6408708 - 650 DIXIE PKWY, WINTER PARK, FL 32789 85 photos

    Bed: 6   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 6007
       Built: 2018   Tax: $41,255 (2025)
    Community: Winflor Court Pt Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,725 (change assumption)
    Mortgage ($23,287) + Taxes in 2025 ($3,438)


    Taxes:$41,255

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1780 BRYAN AVE, WINTER PARK, FL 32789

    $849,000190 Days on yellowkey   MLS ID: O6365369

    For Sale O6365369 - 1780 BRYAN AVE, WINTER PARK, FL 32789 8 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1617
       Built: 1952   Tax: $7,345 (2024)
    Community: Lakeview Terrace
    Single Family


    Estimated Monthly Payment: $5,264 (change assumption)
    Mortgage ($4,652) + Taxes in 2024 ($612)


    Taxes:$7,345

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1600 S PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,200,00038 Days on yellowkey   MLS ID: NS1088189

    For Sale NS1088189 - 1600 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2158
       Built: 1958   Tax: $5,218 (2025)
    Community: Banks Colonial Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,010 (change assumption)
    Mortgage ($6,575) + Taxes in 2025 ($435)


    Taxes:$5,218

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4858 TANGERINE AVE #4858, WINTER PARK, FL 32792

    $209,900101 Days on yellowkey   MLS ID: O6388649

    0 Days Off yellowkey (back on 5/24/2026)

    For Sale O6388649 - 4858 TANGERINE AVE #4858, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1058
       Built: 1973
    Monthly Fee: $392
       Tax: $1,254 (2024)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,647 (change assumption)
    Mortgage ($1,150) + Fees ($392) + Taxes in 2024 ($105)


    Taxes:$1,254

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 311 E MORSE BLVD #7-11, WINTER PARK, FL 32789

    $299,000295 Days on yellowkey   MLS ID: O6337061

    REDUCED by $10,900 (3.5%) on 05/24/2026

    For Sale O6337061 - 311 E MORSE BLVD #7-11, WINTER PARK, FL 32789 25 photos

    Bed: 1   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 570
       Built: 1960   Tax: $668 (2024)
    Community: Phillips Circle Rep
    Condo


    Estimated Monthly Payment: $1,694 (change assumption)
    Mortgage ($1,638) + Taxes in 2024 ($56)


    Taxes:$668

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1540 FLORENTINO LN, WINTER PARK, FL 32792

    $335,00026 Days on yellowkey   MLS ID: O6408841

    For Sale O6408841 - 1540 FLORENTINO LN, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1682
       Built: 2004
    Monthly Fee: $175
       Tax: $5,340 (2025)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,456 (change assumption)
    Mortgage ($1,836) + Fees ($175) + Taxes in 2025 ($445)


    Taxes:$5,340

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2232 BANCHORY ROAD, WINTER PARK, FL 32792

    $1,115,00045 Days on yellowkey   MLS ID: O6404702

    REDUCED by $45,000 (3.9%) on 05/21/2026

    For Sale O6404702 - 2232 BANCHORY ROAD, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2597
       Built: 1966   Tax: $11,186 (2025)
    Community: Brookshire Heights 4Th Add
    Single Family


    Estimated Monthly Payment: $7,042 (change assumption)
    Mortgage ($6,109) + Taxes in 2025 ($932)


    Taxes:$11,186

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1617 CHILEAN LN, WINTER PARK, FL 32792

    $367,500154 Days on yellowkey   MLS ID: O6373026

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $2,400 (0.6%) on 04/30/2026

    For Sale O6373026 - 1617 CHILEAN LN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1359
       Built: 1960   Tax: $3,432 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,300 (change assumption)
    Mortgage ($2,014) + Taxes in 2024 ($286)


    Taxes:$3,432

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1725 CAROLLEE LN, WINTER PARK, FL 32789

    $1,005,00052 Days on yellowkey   MLS ID: O6402656

    0 Days Off yellowkey (back on 5/22/2026)

    REDUCED by $10,000 (1.0%) on 05/12/2026

    For Sale O6402656 - 1725 CAROLLEE LN, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2335
       Built: 1960   Tax: $8,445 (2025)
    Community: Green Terrace
    Single Family


    Estimated Monthly Payment: $6,210 (change assumption)
    Mortgage ($5,507) + Taxes in 2025 ($704)


    Taxes:$8,445

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2973 SANBINA ST, WINTER PARK, FL 32789

    $377,88034 Days on yellowkey   MLS ID: O6407521

    For Sale O6407521 - 2973 SANBINA ST, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1128
       Built: 1965   Tax: $5,253 (2025)
    Community: Howell Heights
    Single Family


    Estimated Monthly Payment: $2,508 (change assumption)
    Mortgage ($2,071) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 758 WARRENTON RD, WINTER PARK, FL 32792

    $318,98578 Days on yellowkey   MLS ID: O6395298

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

    For Sale O6395298 - 758 WARRENTON RD, WINTER PARK, FL 32792 52 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1988
    Monthly Fee: $86
       Tax: $3,689 (2025)
    Community: Winter Park Pines Patio Homes
    Half Duplex


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,748) + Fees ($86) + Taxes in 2025 ($307)


    Taxes:$3,689

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2500 LEE RD #219, WINTER PARK, FL 32789

    $164,000321 Days on yellowkey   MLS ID: O6332524

    3 Days Off yellowkey (back on 3/30/2026)

    For Sale O6332524 - 2500 LEE RD #219, WINTER PARK, FL 32789 37 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 851
       Built: 1969
    Monthly Fee: $360
       Tax: $2,392 (2024)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,458 (change assumption)
    Mortgage ($899) + Fees ($360) + Taxes in 2024 ($199)


    Taxes:$2,392

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2923 ANTIQUE OAKS CIR #34, WINTER PARK, FL 32792

    $190,00028 Days on yellowkey   MLS ID: S5150301

    For Sale S5150301 - 2923 ANTIQUE OAKS CIR #34, WINTER PARK, FL 32792 22 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1984
    Monthly Fee: $441
       Tax: $725 (2025)
    Community: Parkview Village
    Condo


    Estimated Monthly Payment: $1,542 (change assumption)
    Mortgage ($1,041) + Fees ($441) + Taxes in 2025 ($60)


    Taxes:$725

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2512 EASTBROOK BLVD, WINTER PARK, FL 32792

    $390,00028 Days on yellowkey   MLS ID: O6409544

    For Sale O6409544 - 2512 EASTBROOK BLVD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1607
       Built: 1967   Tax: $4,171 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $2,485 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($348)


    Taxes:$4,171

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1910 GLENCOE RD, WINTER PARK, FL 32789

    $3,290,00045 Days on yellowkey   MLS ID: O6403246

    2 Days Off yellowkey (back on 5/21/2026)

    For Sale O6403246 - 1910 GLENCOE RD, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3788
       Built: 2026   Tax: $8,634 (2025)
    Community: Forest Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $18,746 (change assumption)
    Mortgage ($18,027) + Taxes in 2025 ($720)


    Taxes:$8,634

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 1347 CHAPMAN CIR, WINTER PARK, FL 32789

    $1,395,00034 Days on yellowkey   MLS ID: O6408189

    0 Days Off yellowkey (back on 5/20/2026)

    For Sale O6408189 - 1347 CHAPMAN CIR, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2922
       Built: 2013
    Monthly Fee: $268
       Tax: $16,875 (2025)
    Community: Windsong Elizabeths Walk
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,318 (change assumption)
    Mortgage ($7,644) + Fees ($268) + Taxes in 2025 ($1,406)


    Taxes:$16,875

    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.