Home in 2299 Via Tuscany Winter Park for sale with MLS# O6355858

A high motivation price improvement! 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.

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Days on the market

2299 Via Tuscany, Winter Park, FL 32789

Price
Price:
$2,200,000.00
Previous Asking Price:
$2,295,000.00
Original List Price:
$2,345,000.00
List Price per Sq Ft (Calculated, Approx.):
$551.93
Property Status and Type
Listing Type:
For Sale
Status:
Active
Listing Category:
Residential
Property Type:
Single Family House
MLS Number:
O6355858
Rooms Distribution
Bedrooms:
4
Bathrooms Total:
4
Full Bath:
3
Half Bath:
1
Measures
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
Property Features
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
Construction
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
Taxes and Expenses
Homestead Property
Tax Annual Amount:
$26,034.67
Tax Year:
2025
Parking
Garage
Garage Spaces:
2
Attached Garage
Parking Features:
Driveway, Circular Driveway, Guest, Electric Vehicle Charging Station(s), Golf Cart Parking, Garage Faces Side
Utilities
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
Community
Minimum Lease Term:
6 Months
Pets Allowed?
Subdivision Name:
MAITLAND SHORES
Community Features:
Sidewalks, Park, Tennis Court(s), Playground
Senior Community:
No
Terms
Occupant Type:
Owner
Buyer Possession:
Close Of Escrow
Lease Considered:
Yes
Zoning and Legal
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
Public Schools Assigned
Elementary School:
Spring Creek Charter School
High School:
Winter Park High
Middle Or Junior School:
Maitland Middle
Listing History
Originally published on:
November 4, 2025 2:47 pm
Active on the market since:
November 4, 2025
Listing Agreement executed on:
November 4, 2025
Price change occurred on:
April 20, 2026 5:14 pm
Listing Status Last Changed On:
November 4, 2025 2:47 pm
Photos updated on:
November 4, 2025 2:49 pm
Last Modified:
April 20, 2026 7:26 pm
Additional Information
Courtesy of:
CORCORAN PREMIER REALTY
Attribution:
407-965-1155
Road Surface Type:
Brick
Location
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''
Property Map

Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $100,213
Median Home Value $695,000
Median Rent $1,667/mo
Median Age 44
Population 26,884

Air Quality

Source: AirNow.gov · Orlando

🌬️ Air Quality Index (AQI) 51 Moderate
☀️ O3 51 Moderate
🫁 PM2.5 31 Good

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Association of REALTORS®
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