REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Winter Park Homes For Sale & Real Estate - 376 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

Sort:
  • 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792

    $159,000Listed 04/21/2026 6:54PM   MLS ID: O6401114

    For Sale O6401114 - 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792 14 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990   Tax: $2,461 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,076 (change assumption)
    Mortgage ($871) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $399,500Listed 04/21/2026 9:25AM   MLS ID: L4961275

    For Sale L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1144
       Built: 1959   Tax: $5,061 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,611 (change assumption)
    Mortgage ($2,189) + Taxes in 2025 ($422)


    Taxes:$5,061

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,00057 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


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $450,00078 Days on yellowkey   MLS ID: O6379323

    REDUCED by $6,000 (1.3%) on 04/15/2026

    For Sale O6379323 - 2052 LEANNE CT, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 1969   Tax: $1,581 (2024)
    Community: Eastbrook Sub Unit 15
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,597 (change assumption)
    Mortgage ($2,466) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $595,000Listed 04/21/2026 5:59AM   MLS ID: O6400395

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,729 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1307 FORMOSA AVE, WINTER PARK, FL 32789

    $375,000Listed 04/21/2026 5:59PM   MLS ID: O6400711

    For Sale O6400711 - 1307 FORMOSA AVE, WINTER PARK, FL 32789 33 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1150
       Built: 1946   Tax: $6,007 (2025)
    Community: Golfview
    Single Family


    Estimated Monthly Payment: $2,555 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($501)


    Taxes:$6,007

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 106 S INTERLACHEN AVE #518, WINTER PARK, FL 32789

    $1,950,000Listed 04/21/2026 8:50AM   MLS ID: O6400228

    For Sale O6400228 - 106 S INTERLACHEN AVE #518, WINTER PARK, FL 32789 58 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1807
       Built: 1971   Tax: $14,974 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $11,933 (change assumption)
    Mortgage ($10,685) + Taxes in 2025 ($1,248)


    Taxes:$14,974

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1507 GOLFSIDE DR, WINTER PARK, FL 32792

    $925,00020 Days on yellowkey   MLS ID: O6395355

    REDUCED by $50,000 (5.1%) on 04/20/2026

    For Sale O6395355 - 1507 GOLFSIDE DR, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2003
       Built: 1981   Tax: $2,783 (2025)
    Community: Greenview At Winter Pines
    Single Family


    Estimated Monthly Payment: $5,300 (change assumption)
    Mortgage ($5,068) + Taxes in 2025 ($232)


    Taxes:$2,783

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2220 FAIRGLENN WAY, WINTER PARK, FL 32792

    $674,9005 Days on yellowkey   MLS ID: O6399993

    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: $4,031 (change assumption)
    Mortgage ($3,698) + 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


  • 144 LEWFIELD CIR #144, WINTER PARK, FL 32792

    $137,00041 Days on yellowkey   MLS ID: O6390043

    REDUCED by $7,000 (4.9%) on 04/21/2026

    For Sale O6390043 - 144 LEWFIELD CIR #144, WINTER PARK, FL 32792 18 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $351
       Tax: $720 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,162 (change assumption)
    Mortgage ($751) + Fees ($351) + Taxes in 2024 ($60)


    Taxes:$720

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $775,00024 Days on yellowkey   MLS ID: O6394524

    For Sale O6394524 - 350 CORNWALL RD, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2038
       Built: 1963   Tax: $2,127 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($177)


    Taxes:$2,127

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2614 PARKLAND DR, WINTER PARK, FL 32789

    $1,950,000367 Days on yellowkey   MLS ID: O6301489

    REDUCED by $29,000 (1.5%) on 03/31/2026

    For Sale O6301489 - 2614 PARKLAND DR, WINTER PARK, FL 32789 54 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3307
       Built: 2007   Tax: $12,712 (2024)
    Community: Parklando 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,744 (change assumption)
    Mortgage ($10,685) + Taxes in 2024 ($1,059)


    Taxes:$12,712

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1108 FAIRWAY DR, WINTER PARK, FL 32792

    $725,00054 Days on yellowkey   MLS ID: O6386266

    For Sale O6386266 - 1108 FAIRWAY DR, WINTER PARK, FL 32792 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1677
       Built: 1978   Tax: $6,713 (2024)
    Community: Golfside Sec 03
    Single Family


    Estimated Monthly Payment: $4,532 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($559)


    Taxes:$6,713

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792

    $265,00028 Days on yellowkey   MLS ID: S5146437

    REDUCED by $20,000 (7.0%) on 04/21/2026

    For Sale S5146437 - 2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1495
       Built: 1984   Tax: $3,702 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,761 (change assumption)
    Mortgage ($1,452) + Taxes in 2024 ($308)


    Taxes:$3,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1130 PARK NORTH PLACE, WINTER PARK, FL 32789

    $2,650,00027 Days on yellowkey   MLS ID: O6392394

    For Sale O6392394 - 1130 PARK NORTH PLACE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4011
       Built: 1968   Tax: $9,744 (2025)
    Community: Park North
    Single Family


    Estimated Monthly Payment: $15,332 (change assumption)
    Mortgage ($14,520) + Taxes in 2025 ($812)


    Taxes:$9,744

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $627,50049 Days on yellowkey   MLS ID: O6387685

    REDUCED by $2,000 (0.3%) on 04/21/2026

    For Sale O6387685 - 2708 LION HEART RD, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1785
       Built: 1963   Tax: $7,007 (2024)
    Community: Winter Park Pines Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,022 (change assumption)
    Mortgage ($3,438) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 7794 COUNTRY PL #2, WINTER PARK, FL 32792

    $241,9005 Days on yellowkey   MLS ID: O6397587

    For Sale O6397587 - 7794 COUNTRY PL #2, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1988
    Monthly Fee: $296
       Tax: $2,620 (2024)
    Community: Goldenrod Villas Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,840 (change assumption)
    Mortgage ($1,325) + Fees ($296) + Taxes in 2024 ($218)


    Taxes:$2,620

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792

    $269,0001 Day on yellowkey   MLS ID: O6400674

    For Sale O6400674 - 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1295
       Built: 1985
    Monthly Fee: $499
       Tax: $2,560 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $2,186 (change assumption)
    Mortgage ($1,474) + Fees ($499) + Taxes in 2024 ($213)


    Taxes:$2,560

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 802 HAMILTON PLACE CT, WINTER PARK, FL 32789

    $1,349,0005 Days on yellowkey   MLS ID: O6398373

    For Sale O6398373 - 802 HAMILTON PLACE CT, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2843
       Built: 2018
    Monthly Fee: $142
       Tax: $9,300 (2025)
    Community: Hamilton Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,309 (change assumption)
    Mortgage ($7,392) + Fees ($142) + Taxes in 2025 ($775)


    Taxes:$9,300

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 720 W WEBSTER AVE, WINTER PARK, FL 32789

    $525,00048 Days on yellowkey   MLS ID: G5108643

    REDUCED by $25,000 (4.5%) on 04/16/2026

    For Sale G5108643 - 720 W WEBSTER AVE, WINTER PARK, FL 32789 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1950   Tax: $5,128 (2024)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $3,304 (change assumption)
    Mortgage ($2,877) + Taxes in 2024 ($427)


    Taxes:$5,128

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland 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.