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Under contract
    • Price cut: $50K (5/27)
    $2,150,000

    2299 Via Tuscany, Winter Park, FL 32789

    4beds
    3,986sqft
    : 
    $13,824/mo
    Get pre-qualified
    Single Family Residence
    Built in 1953
    0.4 Acres Lot
    $2,038,500 Zestimate®
    $539/sqft
    $-- HOA

    What's special

    Two wood-burning fireplacesPebble tec-style pool finishSoaring ceilingsSuper spacious kitchenModern tile floorsLush landscaping
    Under contract-accepting backup offers. BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.
    262 days
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    272
    |
    3
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    Zillow last checked:

    Listing updated:

    Listed by:

    Vincent Scarlatos 407-718-2378,

    CORCORAN PREMIER REALTY 407-965-1155

    Source: Stellar MLS,MLS#: O6355858MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 322 Square Feet
      • Dimensions: 23x14
      Bedroom 2
      • Features: En Suite Bathroom, Shower No Tub, Walk-In Closet(s)
      • Level: First
      • Area: 204 Square Feet
      • Dimensions: 17x12
      Bedroom 3
      • Features: Built-in Closet
      • Level: Second
      • Area: 165 Square Feet
      • Dimensions: 15x11
      Bedroom 4
      • Features: Built-in Closet
      • Level: Second
      • Area: 165 Square Feet
      • Dimensions: 15x11
      Primary bathroom
      • Features: Makeup/Vanity Space, Shower No Tub, Split Vanities
      • Level: First
      Bathroom 2
      • Features: Tub With Shower, Linen Closet
      • Level: Second
      Bathroom 3
      • Features: Single Vanity, Water Closet/Priv Toilet, No Closet
      • Level: First
      Balcony porch lanai
      • Features: No Closet
      • Level: First
      • Area: 560 Square Feet
      • Dimensions: 40x14
      Dining room
      • Level: First
      • Area: 288 Square Feet
      • Dimensions: 24x12
      Family room
      • Level: First
      • Area: 396 Square Feet
      • Dimensions: 22x18
      Florida room
      • Level: First
      • Area: 275 Square Feet
      • Dimensions: 25x11
      Great room
      • Level: First
      • Area: 384 Square Feet
      • Dimensions: 24x16
      Kitchen
      • Level: First
      • Area: 308 Square Feet
      • Dimensions: 22x14
      Library
      • Features: Built-in Closet
      • Level: First
      Utility room
      • Features: Built-in Closet
      • Level: First
      • Area: 112 Square Feet
      • Dimensions: 14x8
      Heating
      • Central
      Cooling
      • Central Air, Zoned
      Appliances
      • Included: Dishwasher, Disposal, Electric Water Heater, Range Hood
      • Laundry: Inside, Laundry Room
      Features
      • High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Vaulted Ceiling(s)
      • Flooring: Porcelain Tile, Tile, Hardwood
      • Windows: Window Treatments
      • Has fireplace: Yes
      • Fireplace features: Family Room, Living Room, Wood Burning
      Interior area
      • Total structure area: 5,353
      • Total interior livable area: 3,986 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Side, Golf Cart Parking, Guest
      • Attached garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Covered, Front Porch, Patio
      • Exterior features: Awning(s), Garden, Irrigation System, Private Mailbox, Sidewalk
      • Has private pool: Yes
      • Pool features: In Ground, Lighting, Other
      • Fencing: Other,Wood
      • Has view: Yes
      • View description: Garden, Pool
      • Waterfront features: Lake Privileges, Boat Ramp - Private
      Lot
      • Size: 0.4 Acres
      • Features: Landscaped, Oversized Lot, Private, Sidewalk
      Details
      • Parcel number: 302132547601020
      • Zoning: R-1AA
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Mid-Century Modern,Traditional
      • Property subtype: Single Family Residence
      Materials
      • Block
      • Foundation: Crawlspace, Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1953

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Fiber Optics, Natural Gas Connected, Public, Water Connected

      Community & HOA

      Community
      • Features: Park, Playground, Sidewalks, Tennis Court(s)
      • Pet fee: $0 monthly
      • Subdivision: MAITLAND SHORES
      HOA
      • Has HOA: No
      Location
      • Region: Winter Park

      Financial & listing details

      • Price per square foot: $539/sqft
      • Tax assessed value: $1,650,431
      • Annual tax amount: $13,185
      • Date on market: 11/4/2025
      • Cumulative days on market: 227 days
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Brick

        Estimated market value

        $2,038,500

        $1.94M - $2.14M

        $6,929/mo

        Price history

        DateEventPrice
        7/8/2026Contingent$2,150,000$539/sqft
        Source: Stellar MLS #O6355858 Report a problem
        6/23/2026Pending sale$2,150,000$539/sqft
        Source: Stellar MLS #O6355858 Report a problem
        6/10/2026Listed for sale$2,150,000$539/sqft
        Source: Stellar MLS #O6355858 Report a problem
        6/1/2026Pending sale$2,150,000$539/sqft
        Source: Stellar MLS #O6355858 Report a problem
        5/27/2026Price change$2,150,000-2.3%$539/sqft
        Source: Stellar MLS #O6355858 Report a problem
        4/20/2026Price change$2,200,000-4.1%$552/sqft
        Source: Stellar MLS #O6355858 Report a problem
        2/13/2026Price change$2,295,000-2.1%$576/sqft
        Source: Stellar MLS #O6355858 Report a problem
        11/4/2025Listed for sale$2,345,000+165%$588/sqft
        Source: Stellar MLS #O6355858 Report a problem
        8/3/2012Sold$885,000-6.3%$222/sqft
        Source: Public Record Report a problem
        6/1/2012Price change$945,000-1%$237/sqft
        Source: Coldwell Banker Residential Real Estate - Winter Park #O5097630 Report a problem
        4/26/2012Listed for sale$955,000+69%$240/sqft
        Source: Coldwell Banker Residential Real Estate - Winter Park #O5097630 Report a problem
        9/19/2001Sold$565,000+50.7%$142/sqft
        Source: Public Record Report a problem
        5/3/2000Sold$375,000$94/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$13,470 +3.9%$872,956 +3%
        2023$12,965 +7.1%$847,530 +3%
        2022$12,103 +1%$822,845 +3%
        2021$11,980 -0.2%$798,879 +1.4%
        2020$12,008 +0.7%$787,849 +2.3%
        2019$11,927 +0.5%$770,136 +1.9%
        2018$11,868 $755,776 -20.1%
        2017$11,868 +0.8%$945,701 +0.9%
        2016$11,771 +2.1%$936,978 +9.9%
        2015$11,534 -3.2%$852,801 +8.8%
        2014$11,913 +2.1%$783,878 +9.4%
        2013$11,666 +30.3%$716,401 +16.7%
        2012$8,957 +2.6%$613,874 -1.5%
        2011$8,728 +4.6%$623,361 -8.2%
        2010$8,348 $678,934 -4.5%
        2009-- $711,105 -0.8%
        2008$7,773 +0.5%$717,176 +0.4%
        2007$7,735 -6%$714,347 +24.3%
        2006$8,226 -0.1%$574,708 +13.3%
        2005$8,235 +4%$507,219 +9.5%
        2004$7,917 +5.8%$463,353 +0.8%
        2003$7,481 +13.1%$459,792 +14.9%
        2002$6,616 +4.9%$400,073 +5.9%
        2001$6,308 +57.3%$377,925 +51%
        2000$4,012 $250,228
        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.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 32789

        Getting around

        32 / 100
        Car-Dependent
        0 / 100
        No Nearby Transit
        32 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Dommerich Elem
        • Middle: Maitland Middle
        • High: Winter Park 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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