2299 VIA TUSCANY, WINTER PARK, FL 32789

$2,295,000 Was $2,345,000

Beds: 4

Baths: 3 Full / 1 Half

Sq. Ft.: 3,986 Sq. Ft.

Year Built: 1953

Lot Size: 0.4 Acres

Garage: 2

Pool: Yes

DOM: 109

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Property Overview

Status: Active

Property Type: Residential

MLS #: 5cb6d2b84b7d460c9b3e94f071e9e564

Subdivision: MAITLAND SHORES

County: Orange

HOA Fee: N/A

Year Built: 1953

Construction: Block

Foundation: Crawlspace, Slab

Roof: Shingle

Cooling: Central Air, Zoned

Heating: Central

Sewer: Septic Tank

Water Source: Public

Zoning: R-1AA

Tax Amount: $26,034.67 (2025)

Listed On: Nov 4, 2025

Description

Welcome to 2299 Via Tuscany, a remarkable 4-bedroom, 3.5 bathroom residence in the prestigious Winter Park Vias. This 3,986 square foot home, set on a .40-acre private lot, offers a blend of luxury and comfort. The property has seen recent updates in the kitchen and bathrooms and features a new architectural shingle roof (2023), Pebble-tech style pool finish and a manicured landscape. Inside, enjoy the elegance of solid hardwood and modern tile flooring, high ceilings, and two wood burning fireplaces. The chef's kitchen is equipped with premium appliances, including SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor boasts a secluded primary suite, a guest bedroom suite, and a study/library with closet and built-ins. Upstairs, find two additional bedrooms and a full bath. Modern amenities include zoned A/C, a new EV charger and epoxy flooring in the 2-car garage. Conveniently located near parks and the Winter Park Racquet Club, this home offers easy access to downtown Winter Park's shops, dining, and cultural venues, making it ideal for families and active lifestyles. 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 schools, green parks, fitness centers/trails, cultural venues—an ideal blend of amenities, charm and location for any homebuyer.

Exterior Features

Awning(s), Garden, Irrigation System, Private Mailbox, Sidewalk

Directions

From Palmer take Mayfield to Via Tuscany to home on left. Or from Horatio to Via Tuscany to home on right.

School Information

Elementary: Dommerich Elem

Middle: Maitland Middle

High: Winter Park High

Location

Get Directions View on Google Maps

Mortgage Estimator

*Estimate includes Principal & Interest (P&I) only. It does not include taxes, insurance, HOA fees, or PMI. Rates and payments may vary. Consult a lender for accurate figures.

Interested in this Property?

Call Us: 813-618-7653

Schedule a Showing

Ask a Question

Listing Information

Provided Courtesy of:

CORCORAN PREMIER REALTY

Listing Agent: Vincent Scarlatos

Information is deemed reliable but not guaranteed. Information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data last updated: February 22, 2026, 6:54 am UTC

MLS Source: Stellar MLS Copyright © 2026

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