


Listing Courtesy of:  STELLAR / Sierra Realty Group LLC      - Contact:  407-557-3119
STELLAR / Sierra Realty Group LLC      - Contact:  407-557-3119  
 STELLAR / Sierra Realty Group LLC      - Contact:  407-557-3119
STELLAR / Sierra Realty Group LLC      - Contact:  407-557-3119  1860 Via Contessa Winter Park, FL 32789
      Active        (224 Days)  
  
          $2,875,000              (USD)              
  OPEN HOUSE TIMES
      - 
            OPENSat, Nov 111:00 am - 1:00 pm
- 
            OPENSun, Nov 211:00 am - 2:00 pm
      Description
      
      
      MLS #:
      
      
O6210791
      O6210791
        Taxes
        
        
$26,363(2023)
      $26,363(2023)
        Lot Size
        
        
0.26 acres
      0.26 acres
        Type
        
        
Single-Family Home
      Single-Family Home
        Year Built
        
        
2003
      2003
        County
        
        
Orange County
    
  Orange County
Listed By
Sylvester Harding, Sierra Realty Group LLC, Contact: 407-557-3119
  Source
STELLAR
Last checked Oct 31 2025 at 3:23 AM GMT+0000
            STELLAR
Last checked Oct 31 2025 at 3:23 AM GMT+0000
        Bathroom Details
        
        
      - Full Bathrooms: 6
        Interior Features
                  
      - Formal Dining Room Separate
- Inside Utility
- Attic
- Unfurnished
- Split Bedroom
- Stone Counters
- Solid Wood Cabinets
- Breakfast Room Separate
- Formal Living Room Separate
- Loft
- Solid Surface Counters
- Bonus Room
- Den/Library/Office
- Family Room
- Crown Molding
- Walk-In Closet(s)
- Appliances: Dishwasher
- Appliances: Refrigerator
- Appliances: Washer
- Ceiling Fans(s)
- Open Floorplan
- Appliances: Disposal
- Appliances: Range Hood
- Appliances: Microwave
- Appliances: Dryer
- Appliances: Built-In Oven
- Central Vaccum
- Appliances: Convection Oven
- Appliances: Exhaust Fan
- Appliances: Gas Water Heater
- Appliances: Tankless Water Heater
- Appliances: Bar Fridge
- Appliances: Cooktop
- Appliances: Wine Refrigerator
- Thermostat
- Eat-In Kitchen
- High Ceilings
- Built-In Features
- Smart Home
- Interior In-Law Suite W/Private Entry
- Primary Bedroom Main Floor
        Subdivision
        
        
      - Lugano Terrace
        Lot Information
                  
      - City Limits
- Paved
- Landscaped
        Property Features
        
        
      - Fireplace: Family Room
- Fireplace: Living Room
- Fireplace: Gas
- Foundation: Stem Wall
- Foundation: Basement
- Foundation: Block
        Heating and Cooling
                  
      - Central
- Heat Pump
- Electric
- Zoned
- Central Air
        Pool Information
        
        
  - Screen Enclosure
- In Ground
- Tile
- Heated
- Gunite
- Lighting
        Flooring
                  
      - Ceramic Tile
- Wood
- Tile
        Exterior Features
                  
    - Block
- Stucco
- Roof: Tile
            Utility Information
            
            
    - Utilities: Cable Connected, Public, Water Connected, Water Source: Public, Electricity Connected, Sewer Connected, Underground Utilities, Natural Gas Connected
- Sewer: Public Sewer
- Energy: Insulation, Hvac, Thermostat
        Parking
        
        
      - Garage Door Opener
- Oversized
        Living Area
        
        
      - 7,000 sqft
        Additional Information: Sierra Realty Group LLC | 407-557-3119
      
  
  Location
  
  
  
Disclaimer: Listings Courtesy of “My Florida Regional MLS DBA Stellar MLS © 2025. IDX information is provided exclusively for consumers personal, non-commercial use and may not be used for any other purpose other than to identify properties consumers may be interested in purchasing. All information provided is deemed reliable but is not guaranteed and should be independently verified.  Last Updated: 10/30/25 20:23
    
 
           
       
					 
					
The chef-inspired kitchen is the heart of the home, featuring 42-inch cabinets, gleaming quartz countertops, a gas range, and double ovens. The oversized eat-in bar and cozy dining area flow into the spacious family room, keeping the chef engaged with guests at all times.
This home offers two expansive primary suites, each providing a peaceful, private retreat. The first and second floors, covering 4,500 SF, include five bedrooms and four baths, while the lower level adds a 2,500 SF in-law suite, complete with a spacious primary bedroom, ensuite bath, two secondary bedrooms, a full hallway bath, kitchenette/bar, gym, large living room, and more. Whether you need a quiet hideaway, home office, entertainment space, or hobby room, this home offers endless possibilities.
The main floor showcases a thoughtfully designed layout with a private main suite, elegant living and dining areas, and a cozy family room with a gas fireplace. French doors lead to the covered rear patio and pool deck, blending indoor and outdoor living. The well-appointed main suite boasts a luxurious bath and custom walk-in closet.
Upstairs, you’ll find four bedrooms, two Jack-and-Jill baths with double sinks, a large laundry room, and a versatile studio/playroom. Custom loft stairs lead to a third-floor bonus space, perfect for kids’ playtime or creative pursuits.
The lower level is a true standout, offering 2,500 SF of flexible space. It includes a private living area, kitchenette, breakfast bar, a generously sized primary bedroom with ensuite, two additional bedrooms, a gym, a workshop area, and a game room complete with a pool table. Large window wells bring in natural light, and the space has direct access to the back patio and pool deck.
Located in a quiet cul-de-sac, just minutes from Park Avenue and a short walk to the Winter Park Racquet Club, this exceptional home is in the highly sought-after Dommerich/Maitland/Winter Park High School district. Don’t miss the opportunity to make this residence your own and fulfill your vision of the perfect Winter Park lifestyle! All measurements and dimensions should be verified.