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$13,500 Just Listed
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Property Description
Exceptional Lease Opportunity | The Vias, Winter Park $13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available Now Rarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves - the coveted Vias neighborhood - this magnificent 7,000 SF residence delivers an unmatched combination of scale, sophistication, and livability across three thoughtfully designed levels. Rich hardwood floors anchor the main living areas, setting a tone of warmth and understated elegance throughout. The open-concept floor plan transitions effortlessly between spaces, equally suited to quiet evenings at home and large-scale entertaining. At the center of it all is a chef's kitchen appointed with 42-inch cabinetry, quartz countertops, a professional gas range, and double ovens. An oversized eat-in bar and adjacent dining area connect seamlessly to the family room, ensuring the cook is always part of the conversation. The home offers two expansive primary suites, each a serene private retreat. The main floor - along with the second level - encompasses 4,500 SF and five bedrooms with four baths. The main suite is a true sanctuary, complete with a spa-caliber bath and a custom walk-in closet. A gas fireplace anchors the family room, while French doors open to the covered rear patio and pool deck. Upstairs, four additional bedrooms are served by two Jack-and-Jill baths, a generous laundry room, and a versatile studio or playroom. Custom loft stairs climb to a third-floor bonus space, ideal for creative pursuits or kids' play. The lower level is an exceptional offering in its own right - a fully appointed 2,500 SF in-law suite with a private living area, kitchenette and breakfast bar, a spacious primary bedroom with ensuite bath, two secondary bedrooms, a full hallway bath, gym, workshop, and a game room with pool table. Generous window wells flood the space with natural light, and direct access to the back patio and pool deck makes the transition between levels completely seamless. Zoned for the highly regarded Dommerich/Maitland/Winter Park High School district, and just minutes from the shops and dining of Park Avenue and a short stroll to the Winter Park Racquet Club - this is Winter Park living at its finest. All measurements and dimensions should be independently verified.
Full Property Details
Full Property Details for 1860 Via Contessa
General
- Rent: $13,500
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6389081
- Updated: 3/10/2026
- Added to Site: 2 day(s) ago
Rental Information
- Lease/Rent Term: 12 Months
Interior
- Number of Rooms: 15
- Interior Features: Built-in Features, Ceiling Fan(s), Central Vacuum, Crown Molding, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Smart Home, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
- Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Wine Refrigerator
- Furnishings: Unfurnished
- Flooring: Ceramic Tile, Porcelain Tile, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 6
- Full Bathrooms: 6
Bedrooms
- Total Bedrooms: 8
Other Rooms
- Laundry: Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: In Ground
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: LUGANO TERRACE
- Driving Directions: From Howell Branch and Temple: Head South on Temple Drive. Make a right onto Via Contessa. House is on the right hand side.
School Information
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
Community
- Community Name: 32789 - Winter Park
- Number of Pets: 1
- Pet Restrictions: Subject to owner approval
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Street Lights
Structural Information
- Stories/Levels: Three Or More
- Square Feet: 7,000
- Year Built: 2003
Lot Features
- Lot Size (Acres): 0.26
- Lot Size (Sq. Ft.): 11,531
- Lot Size: 11531
- Street/Road Desc.: Paved
Financial Considerations
- Lease Price: $13,500
- Application Fee: $50
- Security Deposit: $15,000
Disclosures and Reports
- APN: 322130528000180
- Property ID: 322130528000180
Listed by Kelly Price & Company Llc
Schools
Schools serving 1860 Via Contessa
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Dommerich Elementary School 601 North Thistle Lane, Maitland, FL 32751 | K-5 | 1.3 mi |
Maitland Middle School 701 North Thistle Lane, Maitland, FL 32751 | 6-8 | 1.3 mi |
Winter Park High School 2100 Summerfield Road, Winter Park, FL 32792 | 9-12 | 2.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 1860 Via Contessa
Date
Details
Price
Change
Source
3/10/2026
Listed
$13,500
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
1860 Via Contessa, Winter Park, FL 32789 (MLS# O6389081) is a Single Family property with 8 bedrooms and 6 full bathrooms. 1860 Via Contessa is currently listed for rent at $13,500 and was received on March 10, 2026. Want to learn more about 1860 Via Contessa? Do you have questions about finding other real estate for sale or rent in Winter Park? You can browse all Winter Park rentals or contact a Coldwell Banker agent to request more information.

