2299 VIA TUSCANY WINTER PARK FL 32789 MLS #O6355858

2299 VIA TUSCANY
WINTER PARK, FL, 32789
$2,200,000
4 Beds
3.5 Baths
3,986 SqFt
0.4 Acres
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MLS #O6355858 image #0
Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, a gorgeous 4-bedroom, 3.5-bath home in the coveted Winter Park Vias. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring updated kitchens and baths, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.

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

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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 29, 2026
279
Single Family Listed
87
Avg DOM
486
Avg $ / SqFt
$1,451,152
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 $486. The average listing price for Single Family in WINTER PARK is $1,451,152. To schedule a showing of MLS#o6355858 at 2299 VIA TUSCANY in WINTER PARK, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.

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2299 VIA TUSCANY
WINTER PARK, FL
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