Home in 2299 Via Tuscany Winter Park for sale with MLS# O6355858
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.
2299 Via Tuscany, Winter Park, FL 32789
- Price:
- $2,150,000.00
- Previous Asking Price:
- $2,200,000.00
- Original List Price:
- $2,345,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $539.39
- Listing Type:
- For Sale
- Status:
- Active Under Contract (An offer has been accepted, considering Backup Offers)
- Contract Status:
- Financing, Inspections, Appraisal, Other Contract Contingencies
- Previous Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6355858
- Bedrooms:
- 4
- Bathrooms Total:
- 4
- Full Bath:
- 3
- Half Bath:
- 1
- Living Area:
- 3,986 Sqft
- Built-Up Area:
- 5,353 Sqft
- Lot Area:
- 17,640 Sqft
- Building Area Source:
- Public Records
- Living Area Source:
- Public Records
- Lot Features:
- Oversized Lot, Sidewalk, Private, Street Brick, Landscaped
- Lot Size Acres:
- 0.4
- View from the Property:
- Pool, Garden
- Waterfront:
- No
- Private Pool
- Swimming Pool Features:
- Other, In Ground, Lighting
- Appliances:
- Dishwasher, Disposal, Electric Water Heater, Range Hood
- Interior:
- High Ceilings, Vaulted Ceiling(s), Living Room/dining Room Combo, Split Bedroom, Stone Counters, Window Treatments, Primary Bedroom Main Floor
- Exterior:
- Awning(s), Private Mailbox, Sidewalk, Garden
- Patio and Porch:
- Patio, Covered, Front Porch
- Laundry:
- Inside, Laundry Room
- Fireplace
- Fireplace:
- Living Room, Wood Burning, Family Room
- Air Conditioning System:
- Zoned, Central Air
- Heating System:
- Central
- Fence:
- Wood, Other
- Property Entrance Faces:
- Northeast
- Other Equipment:
- Irrigation Equipment
- Water Access
- Water Access Features:
- Lake - Chain Of Lakes
- Water Extras
- Water Extra Details:
- Boat Ramp - Private
- Year Built:
- 1953
- Roof:
- Shingle
- Architectural Style:
- Traditional, Mid-century Modern
- Levels:
- Two
- Construction Materials:
- Block
- Flooring:
- Tile, Wood
- Foundation Details:
- Slab, Crawlspace
- Flood Zone Code:
- X
- Homestead Property
- Tax Annual Amount:
- $13,185.00
- Tax Year:
- 2025
- Garage
- Garage Spaces:
- 2
- Attached Garage
- Parking Features:
- Driveway, Circular Driveway, Guest, Electric Vehicle Charging Station(s), Golf Cart Parking, Garage Faces Side
- Sewer:
- Septic Tank
- Utilities Available:
- Cable Available, Electricity Connected, Natural Gas Connected, Water Connected, Public, Broadband/High Speed Internet Available, Fiber Optics
- Water Source:
- Public
- Minimum Lease Term:
- 6 Months
- Pets Allowed?
- Subdivision Name:
- MAITLAND SHORES
- Community Features:
- Sidewalks, Park, Tennis Court(s), Playground
- Senior Community:
- No
- Occupant Type:
- Owner
- Buyer Possession:
- Close Of Escrow
- Lease Considered:
- Yes
- Tax Legal Description:
- MAITLAND SHORES R/150 LOT 2 BLK A
- Real Estate Folio Number (Parcel Number):
- 30-21-32-5476-01-020
- Zoning:
- R-1AA
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Oakcrest Elementary School
- High School:
- Winter Park High
- Middle Or Junior School:
- Maitland Middle
- Originally published on:
- November 4, 2025 2:47 pm
- Active on the market since:
- November 4, 2025
- Listing Agreement executed on:
- November 4, 2025
- Purchase Contract Date:
- June 22, 2026
- Price change occurred on:
- May 27, 2026 3:26 pm
- Listing Status Last Changed On:
- June 23, 2026 1:37 pm
- Photos updated on:
- November 4, 2025 2:49 pm
- Last Modified:
- July 17, 2026 4:50 pm
- Courtesy of:
- CORCORAN PREMIER REALTY
- Attribution:
- 407-965-1155
- Road Surface Type:
- Brick
- Street Name:
- VIA TUSCANY
- Street Number:
- 2299
- City:
- WINTER PARK
- State:
- Florida
- Zip Code:
- 32789
- County:
- Orange
- Latitude:
- N28° 37' 14.8''
- Longitude:
- W82° 39' 37.4''
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Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates
Air Quality
Source: AirNow.gov · Orlando
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