To schedule a showing of 2299 Via Tuscany, Winter Park, Florida, Call David Shippey at 863-521-4517 TODAY!

2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789
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2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789 2299 Via Tuscany Winter Park, FL 32789
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$2,150,000 | 4 beds | 3 full baths | 1 half baths | 3,986 sqft

$2,150,000 Reduced -$50,000
2299 Via Tuscany
Winter Park, FL 32789
  • 4Beds
  • 4.00Total Baths
  • 3 Full, 1 HalfBaths
  • 3,986SqFt
  • 1953Year Built
  • 0.40Acres
  • MLS# O6355858
  • Residential
  • SingleFamilyResidence
  • Active
  • Approx Time on Market7 months, 16 days
  • Area32789 - Winter Park
  • CountyOrange
  • Subdivision Maitland Shores
Overview

BACK ON MARKET. 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 coveredtheres 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, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, 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 chefs 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 youll 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 Parks 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 spacesa perfect mix of charm, amenities, and location.

Agriculture / Farm

Association Fees / Info

Community Features:  Playground, Park, TennisCourts, Sidewalks

Pets Allowed:  Yes

Bathroom Info

Total Baths:  4.00

Fullbaths:  3

Building Info

Window Features:  WindowTreatments

Roof:  Shingle

Building Area Source:  PublicRecords

Buyer Compensation

Exterior Features

Style:  MidCenturyModern, Traditional

Pool Features:  InGround, Other

Patio:  Covered, FrontPorch, Patio

Pool Private:  Yes

Exterior Features:  Awnings, Garden, SprinklerIrrigation

Fees / Restrictions

Financial

Original Price:  $2,345,000

Fencing:  Other, Wood

Garage / Parking

Parking Features:  CircularDriveway, Driveway, ElectricVehicleChargingStations, GolfCartGarage, Guest, GarageFacesSide

Attached Garage:  Yes

Garage:  Yes

Green / Env Info

Interior Features

Fireplace Desc:  FamilyRoom, LivingRoom, WoodBurning

Fireplace:  Yes

Floors:  PorcelainTile, Tile, Wood

Levels:  Two

Laundry Features:  Inside, LaundryRoom

Interior Features:  HighCeilings, LivingDiningRoom, MainLevelPrimary, StoneCounters, SplitBedrooms, VaultedCeilings, WindowTreatments

Appliances:  Dishwasher, ElectricWaterHeater, Disposal, RangeHood

Lot Info

Direction Remarks:  From Palmer take Mayfield to Via Tuscany to home on left. Or from Horatio to Via Tuscany to home on right.

Lot Size Units:  Acres

Lot Size Acres:  0.4

Lot Sqft:  17,640

Lot Desc:  Landscaped, OversizedLot, Private

Misc

Other

Special Conditions:  None

Other Rooms Info

Basement:  CrawlSpace

Property Info

Section:  30

Class Type:  SingleFamilyResidence

Property Sub Type:  SingleFamilyResidence

Construction Materials:  Block

Stories:  2

Foundation:  Crawlspace, Slab

Human Modified:  Yes

Room Info

Total Rooms:  15

Sqft Info

Sqft:  3,986

Bulding Area Sqft:  5,353

Living Area Units:  SquareFeet

Living Area Source:  PublicRecords

Tax Info

Tax Year:  2,025

Tax Lot:  2

Tax Legal Description:  MAITLAND SHORES R/150 LOT 2 BLK A

Tax Block:  A

Tax Annual Amount:  13185

Tax Book Number:  R/150

Unit Info

Utilities / Hvac

Heating:  Central

Water Source:  Public

Sewer:  SepticTank

Cool System:  CentralAir, Zoned

Cooling:  Yes

Heating:  Yes

Utilities:  CableAvailable, ElectricityConnected, FiberOpticAvailable, NaturalGasConnected, HighSpeedInternetAvailable, MunicipalUtilities, WaterConnected

Waterfront / Water

View:  Yes

View:  Garden, Pool

Schools

Elem:  Dommerich Elem

Middle:  Maitland Middle

High:  Winter Park High

Directions

From Palmer take Mayfield to Via Tuscany to home on left. Or from Horatio to Via Tuscany to home on right.

This listing courtesy of Corcoran Premier Realty 

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Price & Status History (on davidshippey.com since Tue, Nov 4th 2025)
  • Original Price: $2,345,000
  • Current Price: $2,150,000
  • Price Reduced: $195,000
Date ChangedFromTo
06/10/2026PendingActive
06/01/2026ActivePending
05/27/2026$2,200,000 $2,150,000 Reduced by $50,000
04/20/2026$2,295,000 $2,200,000 Reduced by $95,000
02/13/2026$2,345,000 $2,295,000 Reduced by $50,000
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If you have any questions on 2299 Via Tuscany, Winter Park, Florida, please call David Shippey at 863-521-4517.


MLS# O6355858 located at 2299 Via Tuscany, Winter Park, Florida is brought to you by David Shippey REALTOR®

2299 Via Tuscany, Winter Park, Florida has 4 Beds, 3 Full Bath, and 1 Half Bath.
The MLS Number for 2299 Via Tuscany, Winter Park, Florida is O6355858.
The price for 2299 Via Tuscany, Winter Park, Florida is $2,150,000.
The status of 2299 Via Tuscany, Winter Park, Florida is Active.
The subdivision of 2299 Via Tuscany, Winter Park, Florida is Maitland Shores.
The home located at 2299 Via Tuscany, Winter Park, Florida was built in 2026.