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For sale
    • Price cut: $24.9K (9/10)
    $525,000

    2803 RIDDLE DRIVE, WINTER PARK, FL 32789

    3beds
    1,709sqft
    : 
    $3,613/mo
    Get pre-qualified
    Single Family Residence
    Built in 1955
    0.25 Acres Lot
    $514,300 Zestimate®
    $307/sqft
    $-- HOA

    What's special

    Sparkling private poolTwo-car garageBright open living spaceInviting open floor planWood-burning fireplaceFilled with natural lightPrivate full fenced backyard
    Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.
    74 days
    1,478
    128

    Zillow last checked:

    Listing updated:

    Listed by:

    Allie George 407-457-4815,

    CORCORAN PREMIER REALTY 407-965-1155

    Source: Stellar MLS,MLS#: O6423829MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Dual Closets
      • Level: First
      • Area: 144 Square Feet
      • Dimensions: 12x12
      Bedroom 2
      • Features: Built-in Closet
      • Level: First
      • Area: 121 Square Feet
      • Dimensions: 11x11
      Bedroom 3
      • Features: Built-in Closet
      • Level: First
      • Area: 132 Square Feet
      • Dimensions: 12x11
      Primary bathroom
      • Features: Shower No Tub
      • Level: First
      Dining room
      • Level: First
      • Area: 117 Square Feet
      • Dimensions: 13x9
      Great room
      • Level: First
      • Area: 216 Square Feet
      • Dimensions: 18x12
      Kitchen
      • Level: First
      • Area: 140 Square Feet
      • Dimensions: 14x10
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Electric Water Heater, Microwave, Refrigerator
      • Laundry: In Garage
      Features
      • Cathedral Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s)
      • Flooring: Carpet, Travertine
      • Doors: Sliding Doors
      • Has fireplace: Yes
      • Fireplace features: Living Room, Wood Burning
      Interior area
      • Total structure area: 2,109
      • Total interior livable area: 1,709 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage Door Opener, Guest
      • Attached garage spaces: 2
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Deck, Patio, Porch
      • Exterior features: Irrigation System
      • Has private pool: Yes
      • Pool features: Gunite, In Ground
      • Fencing: Fenced
      Lot
      • Size: 0.25 Acres
      • Dimensions: 85 x 130
      • Features: In County, Landscaped, Oversized Lot, Sidewalk
      • Residential vegetation: Mature Landscaping, Trees/Landscaped
      Details
      • Additional structures: Shed(s), Storage
      • Parcel number: 022229260000040
      • Zoning: R-1A
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Florida
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Crawlspace, Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1955

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available, Electricity Connected, Sprinkler Meter

      Community & HOA

      Community
      • Features: None
      • Pet fee: $0 monthly
      • Subdivision: FAIRSHORES PLACE
      HOA
      • Has HOA: No
      Location
      • Region: Winter Park

      Financial & listing details

      • Price per square foot: $307/sqft
      • Tax assessed value: $365,566
      • Annual tax amount: $6,477
      • Date on market: 7/10/2026
      • Cumulative days on market: 73 days
      • Listing terms: Cash,Conventional,FHA
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt

        Estimated market value

        $514,300

        $489,000 - $540,000

        $2,807/mo

        Price history

        DateEventPrice
        9/10/2026Price change$525,000-4.5%$307/sqft
        Source: Stellar MLS #O6423829 Report a problem
        8/25/2026Price change$549,900-3.4%$322/sqft
        Source: Stellar MLS #O6423829 Report a problem
        7/20/2026Price change$569,000-3.4%$333/sqft
        Source: Stellar MLS #O6423829 Report a problem
        7/10/2026Listed for sale$589,000+156.2%$345/sqft
        Source: Stellar MLS #O6423829 Report a problem
        5/12/2025Listing removed$2,800$2/sqft
        Source: Zillow Rentals Report a problem
        5/9/2025Listed for rent$2,800+24.4%$2/sqft
        Source: Zillow Rentals Report a problem
        1/9/2021Listing removed--
        Source: Owner Report a problem
        5/3/2019Listing removed$2,250$1/sqft
        Source: Owner Report a problem
        3/31/2019Listed for rent$2,250$1/sqft
        Source: Owner Report a problem
        10/31/2014Sold$229,900-7.7%$135/sqft
        Source: Public Record Report a problem
        2/27/2014Listing removed$249,000$146/sqft
        Source: Kelly Price & Company #O5208797 Report a problem
        2/8/2014Listed for sale$249,000+240.2%$146/sqft
        Source: Kelly Price & Company #O5208797 Report a problem
        9/6/2012Sold$73,200-72.4%$43/sqft
        Source: Public Record Report a problem
        1/26/2007Sold$265,000+15.7%$155/sqft
        Source: Public Record Report a problem
        9/29/2005Sold$229,000$134/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$5,973 +8%$343,438 +10%
        2023$5,529 +12.8%$312,216 +10%
        2022$4,901 +13.2%$283,833 +10%
        2021$4,330 +70.4%$258,030 +40.8%
        2020$2,541 +1.9%$183,262 +2.6%
        2019$2,493 +1%$178,653 +1.9%
        2018$2,469 $175,322 -19%
        2017$2,469 +1.7%$216,453 +28.7%
        2016$2,427 +1.2%$168,184 -11.2%
        2015$2,399 +33.7%$189,387 +114.2%
        2014$1,795 +5.9%$88,403 +6.3%
        2013$1,694 -17.3%$83,164 -19.1%
        2012$2,050 -1.9%$102,736 -1.8%
        2011$2,090 -14.8%$104,622 -19%
        2010$2,453 $129,179 -23.3%
        2009-- $168,399 -20.4%
        2008$3,702 -5.1%$211,628 -7.1%
        2007$3,902 +15.5%$227,813 +27.2%
        2006$3,380 +161.3%$179,087 +44%
        2005$1,293 +5.2%$124,367 +4.8%
        2004$1,229 +0.9%$118,640 +1.2%
        2003$1,218 +3.1%$117,225 +22.3%
        2002$1,182 -0.5%$95,882 +15.8%
        2001$1,188 +2.4%$82,831 +7.6%
        2000$1,160 $76,947
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 32789

        Getting around

        47 / 100
        Car-Dependent
        24 / 100
        Minimal Transit
        39 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Killarney Elem
        • Middle: College Park Middle
        • High: Edgewater High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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