2299 VIA TUSCANY Winter Park, FL $ 2,345,000
2299 VIA TUSCANY
$ 2,345,000
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2299 VIA TUSCANY

Winter Park, FL, 32789
$ 2,345,000
Bedrooms4 Baths3.1 Sq 3,986

Monthly Estimate*

$ 14,630

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Single Family Home for sale in Winter Park, FL

for $2,345,000 with 4 bedrooms and 3 full baths, 1 half bath. This 3,986 square foot home was built in 1953 on a lot size of 0.4.

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 property also offers deeded lake access to the Winter Park Chain of Lakes by becoming a member of the Maitland Shores Lakefront Preservation Association for an annual fee. The access is very convenient and offers a private ramp to store and launch kayaks, canoes, etc. 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.

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Single Family Active

Price

$ 2,345,000

Bedrooms

4

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 26,034

Style

Mid-Century Modern Traditional

Lot Size

0.4

Year Built

1953

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6355858

Features
General
Sewer Septic Tank
Heating Central
Cooling Central Air Zoned
Utilities BB/HS Internet Available Cable Available Electricity Connected Fiber Optics Natural Gas Connected Public Water Connected
Possession Close Of Escrow
Roof Shingle
Appliances Dishwasher Disposal Electric Water Heater Range Hood
Zoning R-1AA
Garage Spaces 2
Patio/Porch Features Covered Front Porch Patio
Architectural Style Mid-Century Modern Traditional
Pool Features In Ground Lighting Other
Construction Materials Block
Pets Allowed Yes
Year Built 1953
View Garden Pool
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Park Playground Sidewalks Tennis Court(s)
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name MAITLAND SHORES
Facing Direction Northeast
Garage Y/N true
Total Rooms 15
Full Baths 3
Status Active
Directions From Palmer take Mayfield to Via Tuscany to home on left. Or from Horatio to Via Tuscany to home on right.
High School Winter Park High
City WINTER PARK
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 17640
Carport Y/N false
Elementary School Dommerich Elem
Land Lease Y/N false
Tax Annual Amount 26034.67
Middle/Junior High School Maitland Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6355858
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 2
Legal Description MAITLAND SHORES R/150 LOT 2 BLK A
Water Access Type Lake - Chain of Lakes
Minimum Lease 6 Months
Water Access Y/N true
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities High Ceilings Living Room/Dining Room Combo Primary Bedroom Main Floor Split Bedroom Stone Counters Vaulted Ceiling(s) Window Treatments
Flooring Porcelain Tile Tile Hardwood
Fireplace Features Family Room Living Room Wood Burning
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Inside Laundry Room
Total Bedrooms 4
Total Baths 4
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Exterior
Exterior Amenities Awning(s) Garden Irrigation System Private Mailbox Sidewalk
Fencing Other Wood
Parking Features Circular Driveway Driveway Electric Vehicle Charging Station(s) Garage Faces Side Golf Cart Parking Guest
Lot Features Landscaped Oversized Lot Private Sidewalk
Water Source Public
Lot Size Area 17640
Foundation Details Crawlspace Slab
Building Area Total 5353
Lot Size Acres 0.4
Road Surface Type Brick
Private Pool true
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Street Brick
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* Excluded Features
List By
Corcoran Premier Realty

Broker

viniscarlatos@gmail.com

Email

Affordability Calculator

$16,799
Per Month
87%
13%
0%
Monthly Principal & Interest
$14,630
Monthly Property Taxes
$2,170
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
12/19/2025$2,345,000 Listed Price

Map


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2299 VIA TUSCANY, Winter Park, FL, 32789 is a Single Family Home for sale at $2,345,000 with 3,986 sqft and a lot size of 0.4. 2299 VIA TUSCANY has 4 bedrooms, 3.1 baths, and was built in 1953. The property's zip code is 32789 which is in Winter Park, FL