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Winter Park Townhomes For Sale - 29 townhouses

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

Location: Winter Park

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  • 2676 BARBADOS DR, WINTER PARK, FL 32792

    $340,000Listed 05/29/2026 5:29PM   MLS ID: O6411958

    For Sale O6411958 - 2676 BARBADOS DR, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1743
       Built: 1978
    Monthly Fee: $98
       Tax: $4,131 (2025)
    Community: Windward Square Sec 2
    Townhouse


    Estimated Monthly Payment: $2,305 (change assumption)
    Mortgage ($1,863) + Fees ($98) + Taxes in 2025 ($344)


    Taxes:$4,131

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 643 N PARK AVE, WINTER PARK, FL 32789

    $4,295,00015 Days on yellowkey   MLS ID: O6403591

    For Sale O6403591 - 643 N PARK AVE, WINTER PARK, FL 32789 82 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4231
       Built: 2018
    Monthly Fee: $948
       Tax: $22,352 (2025)
    Community: Park Hill
    Townhouse


    Estimated Monthly Payment: $26,344 (change assumption)
    Mortgage ($23,534) + Fees ($948) + Taxes in 2025 ($1,863)


    Taxes:$22,352

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2529 WINDWARD WAY, WINTER PARK, FL 32792

    $299,0001 Day on yellowkey   MLS ID: S5150790

    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


  • 1995 CANNY CV, WINTER PARK, FL 32792

    $425,00012 Days on yellowkey   MLS ID: G5112476

    For Sale G5112476 - 1995 CANNY CV, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 2023
    Monthly Fee: $375
       Tax: $5,957 (2025)
    Community: Grayson Square
    Townhouse


    Estimated Monthly Payment: $3,200 (change assumption)
    Mortgage ($2,329) + Fees ($375) + Taxes in 2025 ($496)


    Taxes:$5,957

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 901 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00070 Days on yellowkey   MLS ID: O6383602

    For Sale O6383602 - 901 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2738
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 7522 ALOMA PINES CT, WINTER PARK, FL 32792

    $375,0004 Days on yellowkey   MLS ID: S5150544

    For Sale S5150544 - 7522 ALOMA PINES CT, WINTER PARK, FL 32792 28 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1872
       Built: 2017
    Monthly Fee: $407
       Tax: $4,304 (2025)
    Community: Aloma Trails
    Townhouse


    Estimated Monthly Payment: $2,820 (change assumption)
    Mortgage ($2,055) + Fees ($407) + Taxes in 2025 ($359)


    Taxes:$4,304

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1261 INDIANA AVE, WINTER PARK, FL 32789

    $539,00039 Days on yellowkey   MLS ID: O6400698

    For Sale O6400698 - 1261 INDIANA AVE, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 2005
    Monthly Fee: $360
       Tax: $2,892 (2025)
    Community: Townhomes/Harper Place
    Townhouse


    Estimated Monthly Payment: $3,554 (change assumption)
    Mortgage ($2,953) + Fees ($360) + Taxes in 2025 ($241)


    Taxes:$2,892

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1871 CASSELWOOD ST, WINTER PARK, FL 32792

    $419,90027 Days on yellowkey   MLS ID: O6404306

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

    REDUCED by $5,000 (1.2%) on 05/12/2026

    For Sale O6404306 - 1871 CASSELWOOD ST, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 1988
    Monthly Fee: $39
       Tax: $1,223 (2024)
    Community: Villas Of Casselberry Ph 2
    Townhouse


    Estimated Monthly Payment: $2,442 (change assumption)
    Mortgage ($2,301) + Fees ($39) + Taxes in 2024 ($102)


    Taxes:$1,223

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3159 GREENWOOD ST, WINTER PARK, FL 32792

    $290,0009 Days on yellowkey   MLS ID: G5112192

    1 Days Off yellowkey (back on 5/25/2026)

    For Sale G5112192 - 3159 GREENWOOD ST, WINTER PARK, FL 32792 43 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1241
       Built: 1984
    Monthly Fee: $57
       Tax: $1,085 (2024)
    Community: Villas Of Casselberry Ph 2
    Townhouse


    Estimated Monthly Payment: $1,736 (change assumption)
    Mortgage ($1,589) + Fees ($57) + Taxes in 2024 ($90)


    Taxes:$1,085

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1540 FLORENTINO LN, WINTER PARK, FL 32792

    $335,0006 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


  • 7485 ALOMA PINES CT, WINTER PARK, FL 32792

    $375,00049 Days on yellowkey   MLS ID: O6398259

    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


  • 7470 CANFORD CT #23, WINTER PARK, FL 32792

    $248,900196 Days on yellowkey   MLS ID: O6360198

    REDUCED by $1,000 (0.4%) on 05/20/2026

    For Sale O6360198 - 7470 CANFORD CT #23, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1580
       Built: 1974
    Monthly Fee: $575
       Tax: $3,119 (2024)
    Community: Whisperwood Condo
    Townhouse


    Estimated Monthly Payment: $2,199 (change assumption)
    Mortgage ($1,364) + Fees ($575) + Taxes in 2024 ($260)


    Taxes:$3,119

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 962 ARAGON AVE, WINTER PARK, FL 32789

    $599,90014 Days on yellowkey   MLS ID: O6407916

    1 Days Off yellowkey (back on 5/17/2026)

    For Sale O6407916 - 962 ARAGON AVE, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1680
       Built: 1996
    Monthly Fee: $150
       Tax: $5,200 (2025)
    Community: Seville Park
    Townhouse


    Estimated Monthly Payment: $3,870 (change assumption)
    Mortgage ($3,287) + Fees ($150) + Taxes in 2025 ($433)


    Taxes:$5,200

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 905 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00070 Days on yellowkey   MLS ID: O6383679

    For Sale O6383679 - 905 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1611 LITTLE WREN LN, WINTER PARK, FL 32792

    $415,00015 Days on yellowkey   MLS ID: O6406260

    0 Days Off yellowkey (back on 5/17/2026)

    For Sale O6406260 - 1611 LITTLE WREN LN, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1755
       Built: 2020
    Monthly Fee: $333
       Tax: $4,725 (2025)
    Community: Enclave At Hawks Crest
    Townhouse


    Estimated Monthly Payment: $3,001 (change assumption)
    Mortgage ($2,274) + Fees ($333) + Taxes in 2025 ($394)


    Taxes:$4,725

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792

    $300,00085 Days on yellowkey   MLS ID: O6384755

    1 Days Off yellowkey (back on 5/16/2026)

    REDUCED by $15,000 (4.8%) on 04/28/2026

    For Sale O6384755 - 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1652
       Built: 1984
    Monthly Fee: $188
       Tax: $3,993 (2024)
    Community: Winter Green
    Townhouse


    Estimated Monthly Payment: $2,165 (change assumption)
    Mortgage ($1,644) + Fees ($188) + Taxes in 2024 ($333)


    Taxes:$3,993

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2401 ANTILLES DR, WINTER PARK, FL 32792

    $320,000205 Days on yellowkey   MLS ID: O6357934

    0 Days Off yellowkey (back on 5/14/2026)

    For Sale O6357934 - 2401 ANTILLES DR, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1719
       Built: 1977
    Monthly Fee: $95

    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,848 (change assumption)
    Mortgage ($1,753) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 266 W LYMAN AVE, WINTER PARK, FL 32789

    $1,375,00020 Days on yellowkey   MLS ID: O6406526

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

    For Sale O6406526 - 266 W LYMAN AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 2014
    Monthly Fee: $568
       Tax: $11,410 (2024)
    Community: Lyman Ave Villas 1
    Spa: No

    Townhouse


    Estimated Monthly Payment: $9,053 (change assumption)
    Mortgage ($7,534) + Fees ($568) + Taxes in 2024 ($951)


    Taxes:$11,410

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 2400 DOMINICA RUN, WINTER PARK, FL 32792

    $220,00063 Days on yellowkey   MLS ID: O6394406

    0 Days Off yellowkey (back on 5/14/2026)

    REDUCED by $5,000 (2.2%) on 05/06/2026

    For Sale O6394406 - 2400 DOMINICA RUN, WINTER PARK, FL 32792 29 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 854
       Built: 1979
    Monthly Fee: $99
       Tax: $433 (2025)
    Community: Windward Square Sec 3
    Townhouse


    Estimated Monthly Payment: $1,341 (change assumption)
    Mortgage ($1,205) + Fees ($99) + Taxes in 2025 ($36)


    Taxes:$433

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 432 W SWOOPE AVE, WINTER PARK, FL 32789

    $695,000128 Days on yellowkey   MLS ID: O6375719

    For Sale O6375719 - 432 W SWOOPE AVE, WINTER PARK, FL 32789 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2317
       Built: 2014
    Monthly Fee: $463
       Tax: $9,138 (2025)
    Community: Swoope Park
    Townhouse


    Estimated Monthly Payment: $5,033 (change assumption)
    Mortgage ($3,808) + Fees ($463) + Taxes in 2025 ($761)


    Taxes:$9,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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Why Bother Searching Elsewhere for Winter Park Townhomes for Sale and Other Townhouses?

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 townhomes for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park townhouses. 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 townhome 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.