2299 Via Tuscany, WINTER PARK, FL

$2,345,000

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4

Beds

4

Baths

3,986

Square feet

0.40

Acres

About 2299 Via Tuscany

Stunning 4-bedroom, renovated pool home with new Architectural shingle roof (2023) on a generous .40 acre lot in the highly coveted Winter Park Vias with bright open living areas, high ceilings, hardwood oak floors, two fireplaces, and a chef’s kitchen offering premium appliances including SubZero Refrigeration and Viking 6-Burner Gas Cooktop. The private backyard features a large pool, covered lanai with built-in outdoor grill w/prep space, and lush landscaping that creates a safe green space for kids and a low-maintenance oasis for empty nesters. The main floor features a large secluded primary suite and separate full suite guest bedroom plus a gorgeous study/library with built-ins providing substantial single-level living if desired. Upstairs features two nicely sized bedrooms and full bath. This home sits in a sidewalk and tree-lined neighborhood with top-rated schools and quiet streets perfect for bikes, evening strolls to the nearby parks or a meander to the Winter Park Racquet Club with its premier clay courts and private waterfront access. This location offers effortless access to downtown Winter Park’s shops, dining, parks, fitness centers/trails, cultural venues—an ideal blend of family-friendly amenities and low-maintenance, active-lifestyle appeal for empty nesters.

Features of 2299 Via Tuscany

MLS® # O6355858
Price $2,345,000
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 Active

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
Is Waterfront No
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

Date Listed November 4th, 2025
Zoning R-1AA
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeCORCORAN PREMIER REALTY

Listing Map

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