Orlando Realtor Specializing in Family Relocation

Helping families move near Walt Disney World without the tourist traffic

2299 VIA TUSCANY
WINTER PARK, FL, 32789
$2,200,000
4 Beds
3.5 Baths
3,986 SqFt
0.4 Acres
Add
MLS #O6355858 image #0
Open House Apr 25, 2026
01:00 – 03:00
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.

Property Details

Price:
$2,200,000
MLS #:
O6355858
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
MAITLAND SHORES
Neighborhood:
32789winterpark
Listed Date:
Nov 4, 2025
Finished Sq Ft:
3,986
Total Sq Ft:
5,353
Lot Size:
17,640 sqft / 0.40 acres (approx)
Year Built:
1953
PoolTennisPrimary Bedroom Main Floor32789 – Winter Park32789winterparkMaitland ShoresDommerich ElemMaitland MiddleWinter Park HighPlease Review Any Local Ordinances Governing Lease Terms And Frequency6 MonthsPets Allowed

Ask a Question

See this Listing

Send
  

Schools

Elementary School:
Dommerich Elem
Middle School:
Maitland Middle
High School:
Winter Park High

Interior

Appliances
Dishwasher, Disposal, Electric Water Heater, Range Hood
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Porcelain Tile, Tile, Hardwood
Heating
Central
Interior Features
High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Window Treatments
Laundry Features
Inside, Laundry Room
Levels
Two

Exterior

Architectural Style
Mid-Century Modern, Traditional
Attached Garage YN
1
Community Features
Park, Playground, Sidewalks, Tennis Court(s)
Construction Materials
Block
Covered Spaces
2
Direction Faces
Northeast
Exterior Features
Awning(s), Garden, Irrigation System, Private Mailbox, Sidewalk
Fencing
Other, Wood
Garage Spaces
2
Lot Features
Landscaped, Oversized Lot, Private, Sidewalk
Open Parking YN
1
Parking Features
Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Side, Golf Cart Parking, Guest
Patio And Porch Features
Covered, Front Porch, Patio
Roof
Shingle
View
Garden, Pool

Financial

Tax Year
2025
Taxes
$26,035

Map

Community

Subdivisions in WINTER PARK

Market Summary

Current real estate data for Single Family in WINTER PARK as of Apr 23, 2026
274
Single Family Listed
86
Avg DOM
491
Avg $ / SqFt
$1,484,233
Avg List Price

Property Summary

    Located in the MAITLAND SHORES subdivision, 2299 VIA TUSCANY WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $2,200,000 and features 4 beds, 4 baths, and has approximately 3,986 square feet of living space, and was originally constructed in 1953. The current price per square foot is $552. The average price per square foot for Single Family listings in WINTER PARK is $491. The average listing price for Single Family in WINTER PARK is $1,484,233. To schedule a showing of MLS#o6355858 at 2299 VIA TUSCANY in WINTER PARK, FL, contact your Preferred Real Estate Brokers agent at 4076987254.

Similar Listings Nearby

broker reciprocity
MLS# O6393777broker reciprocity
1300 MAYFIELD AVENUE
WINTER PARK, FL

$2,850,000

0.8 miles away

broker reciprocity
MLS# O6388598broker reciprocity
609 S PHELPS AVENUE
WINTER PARK, FL

$2,829,000

2.2 miles away

broker reciprocity
MLS# O6389829broker reciprocity
541 W CANTON AVENUE
WINTER PARK, FL

$2,800,000

1.7 miles away

broker reciprocity
MLS# O6395062broker reciprocity
1529 HOLTS GROVE CIRCLE
WINTER PARK, FL

$2,795,000

1.8 miles away

broker reciprocity
MLS# O6355930broker reciprocity
1411 NOTTINGHAM STREET
ORLANDO, FL

$2,740,000

3.0 miles away

broker reciprocity
MLS# O6390186broker reciprocity
432 WORTHINGTON DRIVE
WINTER PARK, FL

$2,719,000

2.1 miles away

broker reciprocity
MLS# O6392394broker reciprocity
1130 PARK NORTH PLACE
WINTER PARK, FL

$2,495,000

1.2 miles away

broker reciprocity
MLS# O6399931broker reciprocity
2838 WRIGHT AVENUE
WINTER PARK, FL

$2,399,000

3.3 miles away

broker reciprocity
MLS# O6388219broker reciprocity
2550 VENETIAN WAY
WINTER PARK, FL

$2,399,000

0.3 miles away

broker reciprocity
MLS# O6392122broker reciprocity
112 LAKEN LANE
ORLANDO, FL

$2,399,000

4.8 miles away

2299 VIA TUSCANY
WINTER PARK, FL