Back to search
2299 VIA TUSCANY Winter Park, FL $ 2,295,000
Share Save
$ 2,295,000 Get more info
2299 VIA TUSCANY
$ 2,295,000
Back to search
Open House 2/21 1pm - 3pm
Share Save

2299 VIA TUSCANY

Winter Park, FL, 32789
$ 2,295,000
Bedrooms4 Baths3.1 Sq 3,986

Monthly Estimate*

$ 14,131

2299 VIA TUSCANY, Winter Park, FL 32789 - Image 1
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 2
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 3
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 4
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 5
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 6
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 7
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 8
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 9
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 10
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 11
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 12
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 13
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 14
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 15
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 16
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 17
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 18
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 19
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 20
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 21
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 22
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 23
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 24
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 25
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 26
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 27
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 28
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 29
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 30
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 31
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 32
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 33
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 34
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 35
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 36
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 37
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 38
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 39
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 40
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 41
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 42
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 43
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 44
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 45
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 46
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 47
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 48
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 49
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 50
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 51
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 52
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 53
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 54
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 55
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 56
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 57
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 58
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 59
2299 VIA TUSCANY, Winter Park, FL 32789 - Image 60
View a Virtual Tour

Single Family Home for sale in Winter Park, FL

for $2,295,000 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.

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.

See more

Open House

2/21/2026 1:00 PM - 3:00 PM
2299 VIA TUSCANY Winter Park, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
Single Family Active

Price

$ 2,295,000

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
See more
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
See more
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
See more
* Excluded Features
List By
Corcoran Premier Realty

Broker

viniscarlatos@gmail.com

Email

Affordability Calculator

$16,300
Per Month
87%
13%
0%
Monthly Principal & Interest
$14,131
Monthly Property Taxes
$2,170
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
2/13/2026$2,295,000 -2.13% Price Down
12/19/2025$2,345,000 Listed Price

Map

More homes like this one

homes for you

See all
See all

2299 VIA TUSCANY, Winter Park, FL, 32789 is a Single Family Home for sale at $2,295,000 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

Get more info