FL
Orange
WINTER PARK
32789
1860 VIA CONTESSA
1860 VIA CONTESSA, WINTER PARK, FL 32789
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Listing Type
Rental
Listing Status
Active
90
$13,500

Home Details for 1860 VIA CONTESSA

Price
$13,500
Type
Residential Lease
Bedrooms
8
Bathrooms
6.0
Square feet
7000
Year built
2003
Lot size acres
0.26
County
Orange
Total rooms
15
Garage
2
Days on site
1
MLS Listing#
O6389081
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.

Property Features
  • House Interior
    • Built-in Features
    • Crown Molding
    • Eat-in Kitchen
    • High Ceilings
    • Smart Home
    • Stone Counters
    • Walk-In Closet(s)
  • Utilities
    • Cable Available
    • Natural Gas Available
    • Cable Connected
    • Electricity Connected
    • Natural Gas Connected
    • Sewer Connected
  • Cooling Information
    • Central Air
    • Zoned
  • Heating Information
    • Central
    • Electric
  • Water Features
    • Public
  • Garage
    • 1
  • Parking
    • Attached
School Information
School Information for 1860 VIA CONTESSA, WINTER PARK, FL 32789
Elementary School
Dommerich Elem
Middle School
Maitland Middle
High School
Winter Park High
Listing Courtesy: KELLY PRICE & COMPANY LLC - 407-645-4321
Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. 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. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright ©2026 MLS GRID. All Rights Reserved.
Last Updated: 2026-03-10 12:17:51
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EXIT KING REALTY
1800 S. Tamiami Trail, Venice, FL 34293
Chet Hockett
License #: 3552572
Sales Representative
Office
941 497 6060
Agent
941 599 1042
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