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$2,345,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,986 Sq. Ft.
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Stunning 4-bedroom, renovated pool home with new Architectural shingle roof (2023) on a generous .40 acre lot in the highly coveted Winter Park Vias with bright open living areas, high ceilings, hardwood oak floors, two fireplaces, and a chef's kitchen offering premium appliances including SubZero Refrigeration and Viking 6-Burner Gas Cooktop. The private backyard features a large pool, covered lanai with built-in outdoor grill w/prep space, and lush landscaping that creates a safe green space for kids and a low-maintenance oasis for empty nesters. The main floor features a large secluded primary suite and separate full suite guest bedroom plus a gorgeous study/library with built-ins providing substantial single-level living if desired. Upstairs features two nicely sized bedrooms and full bath. This home sits in a sidewalk and tree-lined neighborhood with top-rated schools and quiet streets perfect for bikes, evening strolls to the nearby parks or a meander to the Winter Park Racquet Club with its premier clay courts and private waterfront access. 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 downtown Winter Park's shops, dining, parks, fitness centers/trails, cultural venues-an ideal blend of family-friendly amenities and low-maintenance, active-lifestyle appeal for empty nesters.

Full Property Details for 2299 Via Tuscany

General

  • Price: $2,345,000
  • Taxes: $26,034 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6355858
  • Updated: 11/13/2025
  • Added to Site: 73 day(s) ago

Rental Information

  • Min. Lease: 6 Months

Interior

  • Number of Rooms: 15
  • Interior Features: High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Family Room, Living Room, Wood Burning
  • Appliances: Dishwasher, Disposal, Electric Water Heater, Range Hood
  • Flooring: Porcelain Tile, Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Lighting, Other

Exterior

  • Exterior Features: Awning(s), Garden, Irrigation System, Private Mailbox, Sidewalk
  • Deck/Patio: Covered, Front Porch, Patio
  • Porch/Patio/Deck: Covered, Front Porch, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Side, Golf Cart Parking, Guest

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: MAITLAND SHORES
  • Driving Directions: From Palmer take Mayfield to Via Tuscany to home on left. Or from Horatio to Via Tuscany to home on right.
  • Direction Faces: Northeast

School Information

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

Community

  • Community Name: 32789 - Winter Park
  • Community Features: Park, Playground, Sidewalks, Tennis Court(s)
  • Pet Restrictions: Please check with City of Winter Park and Orange County Ordinances.

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Fiber Optics, Natural Gas Connected, Public, Water Connected

Structural Information

  • Architectural Info: Mid-Century Modern, Traditional
  • Architectural Style: Mid-Century Modern, Traditional
  • Exterior Const.: Block
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,986
  • Sq. Ft. Source: Public Records
  • Year Built: 1953

Lot Features

  • Property View: Garden, Pool
  • Lot Size (Acres): 0.4
  • Lot Size (Sq. Ft.): 17,640
  • Lot Size: 17640
  • Frontage: Street Brick
  • Street/Road Desc.: Brick
  • Fencing (Description): Other, Wood

Water Features

  • Water Access: Yes
  • Water Access Desc: Lake - Chain of Lakes
  • Water Extras: Yes

Financial Considerations

  • Tax Amount: $26,034.67
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: MAITLAND SHORES R/150 LOT 2 BLK A
  • Flood Zone Info: X
  • APN: 302132547601020
  • Property ID: 302132547601020
  • Block/Lot/Section: A

Listed by Corcoran Premier Realty

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Listing agent

— 2299 Via Tuscany —

  • Corcoran Premier Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 2299 Via Tuscany

School District:Orange County School District
NameGradesDistance
Dommerich Elementary School
601 North Thistle Lane, Maitland, FL 32751
K-50.9 mi
Maitland Middle School
701 North Thistle Lane, Maitland, FL 32751
6-80.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2299 Via Tuscany Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/04/2025
Listed
$2,345,000
164.97%
MLS
7/31/2012
Sold
$885,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2299 Via Tuscany

Year
Property Taxes
Change
Tax Assessment
Change
2024
$13,470
—
$1,694,800
94%
2024
$13,470
4%
$872,956
3%
2023
$12,965
8%
$847,530
6%
2021
$11,980
-1%
$798,879
-3%
2022
$12,103
1%
$822,845
4%
2021
$11,980
—
$787,849
2%
2019
$11,927
—
$770,136
2%
2018
$11,868
1%
$755,776
2%
2017
$11,771
2%
$740,231
2%
2016
$11,534
-2%
$725,006
1%
2015
$11,811
-1%
$719,966
1%
2014
$11,913
2%
$714,252
1%
2013
$11,666
—
$703,697
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Corcoran Premier Realty

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2299 Via Tuscany, Winter Park, FL 32789 (MLS# O6355858) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 2299 Via Tuscany is currently listed for $2,345,000 and was received on November 04, 2025. Want to learn more about 2299 Via Tuscany? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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