2299 VIA TUSCANY, Winter Park, FL 32789

• 4 beds |
• 4 baths |
• 3,986 sqft

Property Description

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.

Listing Status:

Pending

Date Added:

November 4, 2025

Data Last Updated:

June 27, 2026 at 11:22PM

Listing Office:

CORCORAN PREMIER REALTY : 407-965-1155

Listing Agent:

Vincent Scarlatos : 407-718-2378

MLS ID:

O6355858

Interior

• General: High CeilingsLiving Room/Dining Room ComboPrimary Bedroom Main FloorSplit BedroomStone CountersVaulted Ceiling(s)Window Treatments
• Appliances: DishwasherDisposalElectric Water HeaterRange Hood
• Laundry: InsideLaundry Room
• Flooring: TileWood
• A/C: Central AirZoned
• Heating: Central
• Fireplace: Family RoomLiving RoomWood BurningFireplace

Exterior

• General: Awning(s)GardenPrivate MailboxSidewalk
• Style: Mid-Century ModernTraditional
• Other Structures: Front PorchPatioCovered
• Pool: In GroundLightingOther
• Parking: Circular DrivewayDrivewayElectric Vehicle Charging Station(s)Garage Faces SideGolf Cart ParkingGuest

Construction

• Roofing: Shingle
• General: BlockTwoCrawlspaceSlab

Location

• Road/Access: Brick
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-1AAMAITLAND SHORES R/150 LOT 2 BLK A30-21-32-5476-01-020
• View: GardenPool
• Fencing: OtherWood

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedFiber OpticsNatural Gas ConnectedPublicWater Connected
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple