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Winter Park Homes for Sale in Winter Park - 63 homes

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

Location: Winter Park, Winter Park

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  • 205 LEWFIELD CIR #205, WINTER PARK, FL 32792

    $220,000138 Days on yellowkey   MLS ID: S5141588

    For Sale S5141588 - 205 LEWFIELD CIR #205, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 927
       Built: 1973   Tax: $796 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,272 (change assumption)
    Mortgage ($1,205) + Taxes in 2024 ($66)


    Taxes:$796

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $150,000162 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


  • 814 DENSMORE DR, WINTER PARK, FL 32792

    $425,00044 Days on yellowkey   MLS ID: O6399773

    2 Days Off yellowkey (back on 5/13/2026)

    For Sale O6399773 - 814 DENSMORE DR, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1610
       Built: 1960   Tax: $5,402 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,779 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($450)


    Taxes:$5,402

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792

    $109,900217 Days on yellowkey   MLS ID: O6355536

    For Sale O6355536 - 311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792 8 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 785
       Built: 1974
    Monthly Fee: $2,097
       Tax: $1,271 (2024)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $2,805 (change assumption)
    Mortgage ($602) + Fees ($2,097) + Taxes in 2024 ($106)


    Taxes:$1,271

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 188 LEWFIELD CIR #188, WINTER PARK, FL 32792

    $129,99088 Days on yellowkey   MLS ID: O6387291

    1 Days Off yellowkey (back on 5/12/2026)

    REDUCED by $9,010 (6.5%) on 04/20/2026

    For Sale O6387291 - 188 LEWFIELD CIR #188, WINTER PARK, FL 32792 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $424 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $748 (change assumption)
    Mortgage ($712) + Taxes in 2024 ($35)


    Taxes:$424

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 433 CAROLINA AVE, WINTER PARK, FL 32789

    $1,395,00019 Days on yellowkey   MLS ID: O6406911

    0 Days Off yellowkey (back on 5/11/2026)

    For Sale O6406911 - 433 CAROLINA AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 3.5
    Liv Area Sq Ft: 2771
       Built: 2018   Tax: $16,685 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $9,034 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($1,390)


    Taxes:$16,685

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 819 DENSMORE DR, WINTER PARK, FL 32792

    $375,00023 Days on yellowkey   MLS ID: O6405658

    3 Days Off yellowkey (back on 5/11/2026)

    For Sale O6405658 - 819 DENSMORE DR, WINTER PARK, FL 32792 39 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1300
       Built: 1961   Tax: $5,225 (2025)
    Community: Winter Park Estates Sec 2
    Single Family


    Estimated Monthly Payment: $2,490 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($435)


    Taxes:$5,225

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00050 Days on yellowkey   MLS ID: O6397694

    For Sale O6397694 - 2408 LAFAYETTE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2838
       Built: 2024   Tax: $3,770 (2024)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,506 (change assumption)
    Mortgage ($8,192) + Taxes in 2024 ($314)


    Taxes:$3,770

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 541 W CANTON AVE, WINTER PARK, FL 32789

    $2,800,00070 Days on yellowkey   MLS ID: O6389829

    For Sale O6389829 - 541 W CANTON AVE, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3553
       Built: 2024   Tax: $4,692 (2024)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $15,733 (change assumption)
    Mortgage ($15,342) + Taxes in 2024 ($391)


    Taxes:$4,692

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 262 LEWFIELD CIR #262, WINTER PARK, FL 32792

    $159,00023 Days on yellowkey   MLS ID: C7525448

    For Sale C7525448 - 262 LEWFIELD CIR #262, WINTER PARK, FL 32792 36 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $1,278 (2024)
    Community: Stratford A Winter Park Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $978 (change assumption)
    Mortgage ($871) + Taxes in 2024 ($106)


    Taxes:$1,278

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 457 E NEW ENGLAND AVE, WINTER PARK, FL 32789

    $3,100,000246 Days on yellowkey   MLS ID: O6345511

    For Sale O6345511 - 457 E NEW ENGLAND AVE, WINTER PARK, FL 32789 30 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3896
       Built: 1920   Tax: $3,876 (2024)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $17,309 (change assumption)
    Mortgage ($16,986) + Taxes in 2024 ($323)


    Taxes:$3,876

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 517 ROUGHBEARD RD, WINTER PARK, FL 32792

    $565,00046 Days on yellowkey   MLS ID: O6399029

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

    For Sale O6399029 - 517 ROUGHBEARD RD, WINTER PARK, FL 32792 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1873
       Built: 1971   Tax: $4,323 (2025)
    Community: Winter Park Pines Unit 17
    Single Family


    Estimated Monthly Payment: $3,456 (change assumption)
    Mortgage ($3,096) + Taxes in 2025 ($360)


    Taxes:$4,323

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1695 LEE RD #E116, WINTER PARK, FL 32789

    $125,00026 Days on yellowkey   MLS ID: O6399346

    For Sale O6399346 - 1695 LEE RD #E116, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966
    Monthly Fee: $624
       Tax: $2,263 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $1,497 (change assumption)
    Mortgage ($685) + Fees ($624) + Taxes in 2025 ($189)


    Taxes:$2,263

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3651 N GOLDENROD RD #D101, WINTER PARK, FL 32792

    $179,00073 Days on yellowkey   MLS ID: O6391256

    3 Days Off yellowkey (back on 5/4/2026)

    REDUCED by $6,000 (3.2%) on 04/24/2026

    For Sale O6391256 - 3651 N GOLDENROD RD #D101, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,000 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,517 (change assumption)
    Mortgage ($981) + Fees ($370) + Taxes in 2025 ($167)


    Taxes:$2,000

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge 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


  • 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


  • 291 LEWFIELD CIR #291, WINTER PARK, FL 32792

    $144,000103 Days on yellowkey   MLS ID: O6382547

    For Sale O6382547 - 291 LEWFIELD CIR #291, WINTER PARK, FL 32792 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $350
       Tax: $1,942 (2025)
    Community: Stratford Winter Park
    Condo


    Estimated Monthly Payment: $1,301 (change assumption)
    Mortgage ($789) + Fees ($350) + Taxes in 2025 ($162)


    Taxes:$1,942

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1695 LEE RD #C202, WINTER PARK, FL 32789

    $205,000452 Days on yellowkey   MLS ID: O6285607

    REDUCED by $5,000 (2.4%) on 04/23/2026

    For Sale O6285607 - 1695 LEE RD #C202, WINTER PARK, FL 32789 1 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966   Tax: $2,126 (2024)
    Community: Waterfall Cove At Winter Park
    Condo


    Estimated Monthly Payment: $1,300 (change assumption)
    Mortgage ($1,123) + Taxes in 2024 ($177)


    Taxes:$2,126

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 225 LEWFIELD CIR #225, WINTER PARK, FL 32792

    $220,000361 Days on yellowkey   MLS ID: O6314817

    For Sale O6314817 - 225 LEWFIELD CIR #225, WINTER PARK, FL 32792 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 953
       Built: 1973
    Monthly Fee: $465
       Tax: $1,020 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,755 (change assumption)
    Mortgage ($1,205) + Fees ($465) + Taxes in 2024 ($85)


    Taxes:$1,020

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 744 CORNWALL RD, WINTER PARK, FL 32792

    $695,000302 Days on yellowkey   MLS ID: O6332168

    REDUCED by $20,000 (2.8%) on 04/15/2026

    For Sale O6332168 - 744 CORNWALL RD, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1968
       Built: 1968   Tax: $5,359 (2024)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,255 (change assumption)
    Mortgage ($3,808) + Taxes in 2024 ($447)


    Taxes:$5,359

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle




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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.