$2,875,000
8 Bed
6 Bath
7,000 Sqft
0.26 Acre Lot

1860 Via Contessa, Winter Park, Florida 32789

  • Residential Property Type
  • 7,000 Sqft Square Footage
  • Garage Door Opener Cars Garage
  • 2003 Year Built
Property Description

Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Vias neighborhood, offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcoming atmosphere. Gorgeous hardwood floors flow throughout the main living areas, enhancing the home’s inviting, warm ambiance. The open-concept design seamlessly blends living spaces, perfect for both intimate family moments and large gatherings.
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.

Basic Details
Residential
For Sale
O6210791
$2,875,000
8
6
7,000 Sqft
2003
0.26 Acre
Active
6
Single Family Residence
: Tile
Features
: Gunite, Heated, In Ground, Lighting, Screen Enclosure, Tile
: Heat Pump, Central, Zoned, Electric
: Central Air, Zoned
: Finished
: Vinyl, Fenced
: Living Room, Gas, Family Room
: Covered, Front Porch, Rear Porch, Screened, Deck, Patio, Porch, Enclosed
: Garage Door Opener, Oversized
: Lighting, Sidewalk, Sliding Doors, Rain Gutters, French Doors, Outdoor Shower
: Ceramic Tile, Tile, Wood
: Open Floorplan, Walk-In Closet(s), High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Thermostat, Ceiling Fans(s), Eat-in Kitchen, Split Bedroom, Smart Home, Solid Wood Cabinets, Stone Counters, Crown Molding, Built-in Features, Central Vaccum
: Laundry Room, Inside, Electric Dryer Hookup, Gas Dryer Hookup
1
: Public Sewer
: Public, Underground Utilities, Electricity Connected, Cable Connected, Natural Gas Connected, Sewer Connected, Water Connected
: Blinds, Double Pane Windows, ENERGY STAR Qualified Windows, Shades, Insulated Windows, Solar Screens, Low-Emissivity Windows
Appliances
: Dishwasher, Microwave, Disposal, Dryer, Gas Water Heater, Refrigerator, Washer, Bar Fridge, Cooktop, Range Hood, Wine Refrigerator, Exhaust Fan, Convection Oven, Tankless Water Heater, Built-In Oven
Address Map
US
FL
Orange
Winter Park
LUGANO TERRACE
32789
VIA CONTESSA
1860
W82° 39' 47.7''
N28° 36' 55.6''
North
FL-426 W; Turn right onto Bear Gully Rd; Turn left to stay on Bear Gully Rd; At the traffic circle, continue straight to stay on Bear Gully Rd; Turn right onto Howell Branch Rd; Turn left onto Temple Dr; Turn right onto Vía Lugano; Turn right onto Vía Contessa; House is on the right.
32789 - Winter Park
R-1AA
Additional Info
SIERRA REALTY GROUP LLC
Sylvester Harding
$0
$0
Additional Information
: Street Lights
: Block, Stucco
: Block, Stem Wall, Basement
2
: Two
: Paved, Landscaped, City Limits
2024-06-02
2790000
https://vimeo.com/1058970687
: Public
1
9162
Financial
26363
Listing Information
261095205
50957
Cash,Conventional,FHA,VA Loan
Active
2025-10-04T16:13:08Z
Stellar
: None
2025-10-04T16:11:46Z
Emmanuel Bart Williams
261228017
50957
SIERRA REALTY GROUP LLC
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Contact Agent
Contact Us
407-615-0866