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$2,150,000 - 2299 Via Tuscany, WINTER PARK

4
Bedrooms
4
Baths
3,986
SQ. Feet
0.4
Acres

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.

Essential Information

  • MLS® #:
    O6355858
  • Price:
    $2,150,000
  • Bedrooms:
    4
  • Bathrooms:
    4.00
  • Full Baths:
    3
  • Half Baths:
    1
  • Square Footage:
    3,986
  • Acres:
    0.40
  • Year Built:
    1953
  • Type:
    Residential
  • Sub-Type:
    Single Family Residence
  • Style:
    Mid-Century Modern, Traditional
  • Status:
    Pending

Community Information

  • Address:
    2299 Via Tuscany
  • Area:
    Winter Park
  • Subdivision:
    MAITLAND SHORES
  • City:
    WINTER PARK
  • County:
    Orange
  • State:
    FL
  • Zip Code:
    32789-1238

Amenities

  • Parking:
    Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Side, Golf Cart Parking, Guest
  • # of Garages:
    2
  • View:
    Garden, Pool
  • Has Pool:
    Yes

Interior

  • Interior Features:
    High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Window Treatments
  • Appliances:
    Dishwasher, Disposal, Electric Water Heater, Range Hood
  • Heating:
    Central
  • Cooling:
    Central Air, Zoned
  • Fireplace:
    Yes
  • Fireplaces:
    Family Room, Living Room, Wood Burning

Exterior

  • Exterior Features:
    Awning(s), Garden, Irrigation System, Private Mailbox, Sidewalk
  • Lot Description:
    Landscaped, Oversized Lot, Private, Sidewalk
  • Roof:
    Shingle
  • Foundation:
    Crawlspace, Slab

School Information

  • Elementary:
    Dommerich Elem
  • Middle:
    Maitland Middle
  • High:
    Winter Park High

Additional Information

  • Days on Market:
    234
  • Zoning:
    R-1AA

Listing Details

  • Listing Office:
    Corcoran Premier Realty

Listing information courtesy of Corcoran Premier Realty.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on August 2nd, 2026 at 7:52pm EDT.