$2,150,000
2299 Via Tuscany
Winter Park, FL 32789
Listing updated: June 1, 2026 at 10:23 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
Under contract-accepting backup offers. 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, 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 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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history207 days on market
- Status: PendingJun 1, 2026
- Listed$2,345,000Nov 4, 2025
- Price reduced$2,150,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Pending
- Days on market
- 207
- Subdivision
- Maitland Shores
- County
- Orange
- Year built
- 1953
- Living area
- 3,986 sq ft
- Price/sq ft
- $539
- Building area
- 5,353 sq ft (Public Records)
- Lot size
- 17,640 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $13,185 (2025)
- Parcel #
- 30-21-32-5476-01-020
- Zoning
- R-1AA
- MLS #
- O6355858
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Half bathrooms
- 1
- Flooring
- Tile, Wood
- Appliances
- Dishwasher, Disposal, Electric Water Heater, Range Hood
- Interior features
- High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Window Treatments
- Laundry
- Inside, Laundry Room
- Stories / Levels
- Two
- Direction faces
- Northeast
- Fireplace
- Yes
- In-law suite
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Side, Golf Cart Parking, Guest
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 6 Months
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Please review any local ordinances governing lease terms and frequency
Exterior & Construction
- Exterior features
- Awning(s), Garden, Private Mailbox, Sidewalk
- Construction materials
- Block
- Roof
- Shingle
- Foundation
- Crawlspace, Slab
- Pool
- Private pool
- Water access
- Yes
- Road surface
- Brick
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Fiber Optics, Natural Gas Connected, Public, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Dining Room | First | 24x12 |
| Great Room | First | 24x16 |
| Kitchen | First | 22x14 |
| Florida Room | First | 25x11 |
| Primary Bedroom | First | 23x14 |
| Primary Bathroom | First | |
| Bedroom 2 | First | 17x12 |
| Family Room | First | 22x18 |
| Bedroom 3 | Second | 15x11 |
| Bedroom 4 | Second | 15x11 |
| Bathroom 2 | Second | |
| Library | First | |
| Bathroom 3 | First | |
| Utility Room | First | 14x8 |
| Balcony/Porch/Lanai | First | 40x14 |
Listing Details
- Listing date
- 2025-11-04
- On market date
- 2025-11-04
- Original list price
- $2,345,000
- Occupant type
- Owner
- MLS area
- 32789 - Winter Park
- Listing AOR
- Orlando Regional
- Status changed
- 2026-06-01
- Tax legal description
- MAITLAND SHORES R/150 LOT 2 BLK A
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From Palmer take Mayfield to Via Tuscany to home on left. Or from Horatio to Via Tuscany to home on right.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 1, 2026 at 10:23 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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