Guide to Winter Park

There is nowhere quite like Winter Park - a district located in the heart of Orlando; it is truly a one-of-a-kind neighborhood. With a current population of over 30,000, Winter Park is full of character and rich with history. Winter Park was established in 1882, incorporated in 1925 and has become the premiere neighborhood of Orlando. Those looking to move to Winter Park will be neighbors with varying residents such as Doctors, Lawyers and Business Executives. There is one main distinction to be made about Winter Park - the Historic Winter Park and the East Aloma area. Most Orlando residents when referring to “Winter Park,” are referring to the Historic Winter Park. 

Historic Winter Park is home to Rollins College - a very prestigious liberal arts college whose unique architecture alone is worth the visit. Along with Rollins, you will find the gorgeous Park Avenue - a remarkable street with many restaurants, cafes, and retail shops. Additionally, you will encounter many parks, lakes and cobblestone streets that truly make this area a picturesque juxtaposition between a beautifully preserved past and a state of the art modern present.

Countless activities can be found in addition to its vast number of restaurants and shops. Winter Park is known for its rich culture which can be discovered in many art shows throughout the year, world class music festivals and countless museums that are open year-round.  If you are more interested in sports, some of the more popular sports in Winter Park include golf, dance, and boating. 

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  • Orlando Science Elementary Charter School  A+
  • Dommerich Elementary School  A+
  • Winter Park High School  A+
  • Lake Highland Preparatory School  A+

    Lifestyle

    Winter Park Chamber of Commerce

    25 Things to Do In Winter Park

    Just Listed Winter Park Homes For Sale:

    New Listing - 3 days online
    $465,000
    Single Family Home For Sale
    Active
    4
    BEDS
    3
    TOTAL BATHS
    2,080
    SQFT
    7604 Waunaqua Drive
    Winter Park, FL 32792
    Lake Waunatta Cove Subdivision
    New Listing - 3 days online
    $270,000
    Single Family Home For Sale
    Active
    2
    BEDS
    2
    TOTAL BATHS
    1,508
    SQFT
    2712 Riddle Drive
    Winter Park, FL 32789
    Fairbanks Shores Subdivision
    New Listing - 2 days online
    $985,000
    Condo For Sale
    Active
    2
    BEDS
    2
    TOTAL BATHS
    1,602
    SQFT
    315 E New England Avenue E #8
    Winter Park, FL 32789
    Villa Siena Subdivision
    Open House Sun, Mar 7, 11 AM UTC
    Please verify times due to COVID-19
    $375,000
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,210
    SQFT
    2412 Middleton Avenue
    Winter Park, FL 32792
    Brookshire Heights 1st Add Subdivision
    New Listing - 2 days online
    $325,000
    Single Family Home For Sale
    Active
    4
    BEDS
    3
    TOTAL BATHS
    1,983
    SQFT
    1756 Clematis Lane
    Winter Park, FL 32792
    Eastbrook Sub Unit 06 Rep of Pt of Blk 14 Subdivision
    New Listing - 2 days online
    $265,000
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,407
    SQFT
    7059 Citrus Point Court
    Winter Park, FL 32792
    Citrus Point Subdivision
    Open House Sun, Mar 7, 1 PM UTC
    Please verify times due to COVID-19
    $775,000
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,368
    SQFT
    2600 Venetian Way
    Winter Park, FL 32789
    Maitland Shores First Add Subdivision
    Open House Sun, Mar 7, 12 PM UTC
    Please verify times due to COVID-19
    $350,000
    Single Family Home For Sale
    Active
    4
    BEDS
    2
    TOTAL BATHS
    1,768
    SQFT
    2436 Beman Court
    Winter Park, FL 32792
    Eastbrook Sub Unit 09 Subdivision
    New Listing - yesterday
    $330,000
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,798
    SQFT
    2006 Bentwood Drive
    Winter Park, FL 32792
    Cedar Ridge Unit 2 Subdivision
    Open House Sun, Mar 7, 1 AM UTC
    Please verify times due to COVID-19
    $215,000
    Condo For Sale
    Active
    2
    BEDS
    2
    TOTAL BATHS
    1,004
    SQFT
    2419 Gallery View Drive #204
    Winter Park, FL 32792
    Gallery At Winter Park Sec 03 Subdivision
    Open House Sun, Mar 7, 1 PM UTC
    Please verify times due to COVID-19
    $1,124,900
    Single Family Home For Sale
    Active
    3
    BEDS
    4
    TOTAL BATHS
    3,607
    SQFT
    901 Bonita Drive
    Winter Park, FL 32789
    Comstock Park Subdivision
    New Listing - yesterday
    $229,900
    Townhouse For Sale
    Active
    3
    BEDS
    3
    TOTAL BATHS
    1,652
    SQFT
    1508 Winter Green Boulevard
    Winter Park, FL 32792
    Winter Green Subdivision
    New Listing - yesterday
    $450,000
    Single Family Home For Sale
    Active
    4
    BEDS
    4
    TOTAL BATHS
    2,319
    SQFT
    7892 Pleasant Pine Circle
    Winter Park, FL 32792
    Enclave At Aloma Subdivision
    New Listing - yesterday
    $659,000
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,638
    SQFT
    1560 Grove Terrace
    Winter Park, FL 32789
    Sylvan Lake Shores Subdivision
    New Listing - yesterday
    $1,890,000
    Single Family Home For Sale
    Active
    4
    BEDS
    5
    TOTAL BATHS
    3,443
    SQFT
    1016 Mckean Circle
    Winter Park, FL 32789
    Palmer Park Subdivision
    New Listing - yesterday
    $230,000
    Townhouse For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,467
    SQFT
    2518 Leeward Way
    Winter Park, FL 32792
    Windward Square Sec 1 Subdivision
    New Listing - yesterday
    $144,900
    Condo For Sale
    Active
    2
    BEDS
    2
    TOTAL BATHS
    1,030
    SQFT
    3053 George Mason Avenue #8
    Winter Park, FL 32792
    Colonies Subdivision
    Open House Sun, Mar 7, 2 AM UTC
    Please verify times due to COVID-19
    $159,900
    Condo For Sale
    Active
    1
    TOTAL BATH
    640
    SQFT
    700 Melrose Avenue #G 34
    Winter Park, FL 32789
    Winter Park Gardens Condo Subdivision
    New Listing - 9 hours online
    $1,149,000
    Single Family Home For Sale
    Active
    4
    BEDS
    5
    TOTAL BATHS
    3,412
    SQFT
    2715 Norris Ave
    Winter Park, FL 32789
    Parklando 02 Subdivision
    New Listing - 2 hours online
    $314,999
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,198
    SQFT
    2685 Bongart Road
    Winter Park, FL 32792
    Winter Park Estates Subdivision

    Upcoming Open Houses:

    Open House Sun, Mar 7, 1 AM UTC
    Please verify times due to COVID-19
    $215,000
    Condo For Sale
    Active
    2
    BEDS
    2
    TOTAL BATHS
    1,004
    SQFT
    2419 Gallery View Drive #204
    Winter Park, FL 32792
    Gallery At Winter Park Sec 03 Subdivision
    Open House Sun, Mar 7, 11 AM UTC
    Please verify times due to COVID-19
    $493,200
    Single Family Home For Sale
    Active
    4
    BEDS
    2
    TOTAL BATHS
    1,899
    SQFT
    1712 Arbor Park Drive
    Winter Park, FL 32789
    Conwill Estates Subdivision
    Open House Sun, Mar 7, 11 AM UTC
    Please verify times due to COVID-19
    $835,000
    Single Family Home For Sale
    Active
    4
    BEDS
    4
    TOTAL BATHS
    2,170
    SQFT
    1751 Goodrich Avenue
    Winter Park, FL 32789
    Sylvan Heights Subdivision
    Open House Sun, Mar 7, 1 PM UTC
    Please verify times due to COVID-19
    $1,124,900
    Single Family Home For Sale
    Active
    3
    BEDS
    4
    TOTAL BATHS
    3,607
    SQFT
    901 Bonita Drive
    Winter Park, FL 32789
    Comstock Park Subdivision
    Open House Sun, Mar 7, 12 PM UTC
    Please verify times due to COVID-19
    $1,399,000
    Single Family Home For Sale
    Active
    4
    BEDS
    5
    TOTAL BATHS
    3,616
    SQFT
    1637 Magnolia Avenue
    Winter Park, FL 32789
    Flora Park 2nd Add Subdivision
    Open House Sun, Mar 7, 1 PM UTC
    Please verify times due to COVID-19
    $325,000
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,383
    SQFT
    2734 Scarlet Road
    Winter Park, FL 32792
    Winter Park Pines Subdivision
    Open House Sun, Mar 7, 11 AM UTC
    Please verify times due to COVID-19
    $375,000
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,210
    SQFT
    2412 Middleton Avenue
    Winter Park, FL 32792
    Brookshire Heights 1st Add Subdivision
    Open House Sun, Mar 7, 12 PM UTC
    Please verify times due to COVID-19
    $1,099,000
    Single Family Home For Sale
    Active
    3
    BEDS
    4
    TOTAL BATHS
    2,244
    SQFT
    911 Osceola Avenue
    Winter Park, FL 32789
    Osceola Shores Sec 01 Subdivision
    Open House Sun, Mar 7, 1 PM UTC
    Please verify times due to COVID-19
    $932,000
    Single Family Home For Sale
    Active
    4
    BEDS
    4
    TOTAL BATHS
    3,019
    SQFT
    567 Osceola Avenue
    Winter Park, FL 32789
    Osceola Court Subdivision
    Open House Sun, Mar 7, 12 PM UTC
    Please verify times due to COVID-19
    $3,995,000
    Single Family Home For Sale
    Active
    10
    BEDS
    14
    TOTAL BATHS
    8,325
    SQFT
    433 E New England Avenue
    Winter Park, FL 32789
    Winter Park Subdivision
    Open House Sun, Mar 7, 12 PM UTC
    Please verify times due to COVID-19
    $300,000
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,567
    SQFT
    3413 Bowman Drive
    Winter Park, FL 32792
    Eastbrook Subdivision
    Open House Sun, Mar 7, 1 PM UTC
    Please verify times due to COVID-19
    $300,000
    Condo For Sale
    Active
    1
    BED
    1
    TOTAL BATH
    733
    SQFT
    251 E Canton Avenue #251
    Winter Park, FL 32789
    Village Winterset Inc Subdivision
    Open House Sun, Mar 7, 1 PM UTC
    Please verify times due to COVID-19
    $775,000
    Single Family Home For Sale
    Active
    3
    BEDS
    2
    TOTAL BATHS
    1,368
    SQFT
    2600 Venetian Way
    Winter Park, FL 32789
    Maitland Shores First Add Subdivision
    Open House Sun, Mar 7, 12 PM UTC
    Please verify times due to COVID-19
    $350,000
    Single Family Home For Sale
    Active
    4
    BEDS
    2
    TOTAL BATHS
    1,768
    SQFT
    2436 Beman Court
    Winter Park, FL 32792
    Eastbrook Sub Unit 09 Subdivision
    Open House Sun, Mar 7, 12 AM UTC
    Please verify times due to COVID-19
    $899,900
    Single Family Home For Sale
    Active
    4
    BEDS
    4
    TOTAL BATHS
    3,313
    SQFT
    1420 Chapman Circle
    Winter Park, FL 32789
    Windsong Elizabeths Walk Subdivision
    Open House Sun, Mar 7, 1 PM UTC
    Please verify times due to COVID-19
    $928,500
    Single Family Home For Sale
    Active
    3
    BEDS
    4
    TOTAL BATHS
    3,170
    SQFT
    1433 Chapman Circle
    Winter Park, FL 32789
    Windsong Elizabeths Walk 43/81 Subdivision
    Open House Sun, Mar 7, 12 PM UTC
    Please verify times due to COVID-19
    $688,000
    Single Family Home For Sale
    Active
    5
    BEDS
    4
    TOTAL BATHS
    3,532
    SQFT
    2094 Laurelwood Way
    Winter Park, FL 32792
    Preserve At Hawks Crest Subdivision
    Open House Sun, Mar 7, 1 PM UTC
    Please verify times due to COVID-19
    $1,350,000
    Single Family Home For Sale
    Active
    5
    BEDS
    3
    TOTAL BATHS
    3,804
    SQFT
    1807 Barker Drive
    Winter Park, FL 32789
    South Lakemont Shores Subdivision
    Open House Sun, Mar 7, 11 AM UTC
    Please verify times due to COVID-19
    $925,000
    Single Family Home For Sale
    Active
    4
    BEDS
    4
    TOTAL BATHS
    3,457
    SQFT
    811 Hamilton Place Court
    Winter Park, FL 32789
    Hamilton Place Subdivision
    Open House Tue, Mar 9, 12 PM UTC
    Please verify times due to COVID-19
    $1,249,000
    Single Family Home For Sale
    Active
    3
    BEDS
    4
    TOTAL BATHS
    2,281
    SQFT
    1601 Legion Drive
    Winter Park, FL 32789
    Green Oaks Rep 02 Subdivision