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Property Description
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.
Full Property Details
Full Property Details for 2299 Via Tuscany
General
- Sold For: $2,025,000
- Taxes: $13,185 (2025)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6355858
- Added to Site: 276 day(s) ago
Rental Information
- Min. Lease: 6 Months
Interior
- Number of Rooms: 15
- Interior Features: High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Window Treatments
- Fireplace: Yes
- Fireplace(s): Family Room, Living Room, Wood Burning
- Appliances: Dishwasher, Disposal, Electric Water Heater, Range Hood
- Flooring: Porcelain Tile, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: In Ground, Lighting, Other
Exterior
- Exterior Features: Awning(s), Garden, Irrigation System, Private Mailbox, Sidewalk
- Deck/Patio: Covered, Front Porch, Patio
- Porch/Patio/Deck: Covered, Front Porch, Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Side, Golf Cart Parking, Guest
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: MAITLAND SHORES
- Driving Directions: From Palmer take Mayfield to Via Tuscany to home on left. Or from Horatio to Via Tuscany to home on right.
- Direction Faces: Northeast
School Information
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
Community
- Community Name: 32789 - Winter Park
- Community Features: Park, Playground, Sidewalks, Tennis Court(s)
- Pet Restrictions: Please check with City of Winter Park and Orange County Ordinances.
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Central
Utilities
- Sewer: Septic Tank
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Fiber Optics, Natural Gas Connected, Public, Water Connected
Structural Information
- Architectural Info: Mid-Century Modern, Traditional
- Architectural Style: Mid-Century Modern, Traditional
- Exterior Const.: Block
- Roof: Shingle
- Stories/Levels: Two
- Square Feet: 3,986
- Sq. Ft. Source: Public Records
- Living Area: 3,986 Sq. Ft.
- Year Built: 1953
Lot Features
- Property View: Garden, Pool
- Lot Size (Acres): 0.4
- Lot Size (Sq. Ft.): 17,640
- Lot Size: 17640
- Frontage: Street Brick
- Street/Road Desc.: Brick
- Fencing (Description): Other, Wood
Water Features
- Water Access: Yes
- Water Access Desc: Lake - Chain of Lakes
- Water Extras: Yes
Financial Considerations
- Tax Amount: $13,185
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: MAITLAND SHORES R/150 LOT 2 BLK A
- Flood Zone Info: X
- APN: 302132547601020
- Property ID: 302132547601020
- Block/Lot/Section: A
Listed by Corcoran Premier Realty
Sold by Redfin Corporation
Get Pre-Approved Today
Schools
Schools serving 2299 Via Tuscany
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Dommerich Elementary School 601 North Thistle Lane, Maitland, FL 32751 | K-5 | 0.9 mi |
Maitland Middle School 701 North Thistle Lane, Maitland, FL 32751 | 6-8 | 0.9 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 2299 Via Tuscany
Date
Details
Price
Change
Source
8/06/2026
Sold
$2,025,000
-5.81%
MLS
5/27/2026
Price Reduced
$2,150,000
-2.27%
MLS
4/20/2026
Price Reduced
$2,200,000
-4.14%
MLS
2/13/2026
Price Reduced
$2,295,000
-2.13%
MLS
11/04/2025
Listed
$2,345,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
2299 Via Tuscany, Winter Park, FL 32789 (MLS# O6355858) is a Single Family property that was sold at $2,025,000 on August 06, 2026. Want to learn more about 2299 Via Tuscany? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

