1860 Via Contessa, WINTER PARK, FL 32789
Local realty services provided by:Better Homes and Gardens Real Estate Thomas Group



1860 Via Contessa,WINTER PARK, FL 32789
$2,790,000
- 8 Beds
- 6 Baths
- 7,000 sq. ft.
- Single family
- Active
Upcoming open houses
- Sat, Aug 1610:00 am - 05:00 pm
- Sun, Aug 1711:00 am - 05:00 pm
Listed by:sylvester harding
Office:sierra realty group llc.
MLS#:O6210791
Source:MFRMLS
Price summary
- Price:$2,790,000
- Price per sq. ft.:$304.52
About this home
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.
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Home facts
- Year built:2003
- Listing Id #:O6210791
- Added:173 day(s) ago
- Updated:August 15, 2025 at 02:01 PM
Rooms and interior
- Bedrooms:8
- Total bathrooms:6
- Full bathrooms:6
- Living area:7,000 sq. ft.
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Central, Electric, Heat Pump, Zoned
Structure and exterior
- Roof:Tile
- Year built:2003
- Building area:7,000 sq. ft.
- Lot area:0.26 Acres
Utilities
- Water:Public, Water Connected
- Sewer:Public, Public Sewer, Sewer Connected
Finances and disclosures
- Price:$2,790,000
- Price per sq. ft.:$304.52
- Tax amount:$26,363 (2023)
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