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1860 VIA CONTESSA,  WINTER PARK, FL 32789

MLS# O6389081.  8 beds.  6.0 baths.  Single Family Home.  Active

Application Fee: $50.00.

$13,500

 

Remarks:

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.

Rental Info:

  • Listing is courtesy Of: KELLY PRICE & COMPANY LLC ((407-645-4321))
  • Listing Agent: Listing Agent: Kelly Price ((407-645-4321))
  • Possible Short Term Rental
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  • Available Date: 2026-03-09
  • Application Fee:$ 50.00
  • Deposit Includes:
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  • Lease Term: Twelve Months
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Quick Info:

  • Listing is courtesy Of: KELLY PRICE & COMPANY LLC ((407-645-4321))
  • Listing Agent: Kelly Price ((407-645-4321))
  • Days on yellowkey: 41
  • Property Type: Single Family Home
  • Beds: 8
  • Baths: 6.0
  • Living Area Square Feet: 7000
  • Built 2003
  • 0 Days off yellowkey (back on 4/20/2026 )
  • Garage Spaces:2 ()
  • Square Feet: 9162
  • Fees: $0
  • Orange County
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  • Occupancy Information: Vacant
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  • Subdivision Name: LUGANO TERRACE
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  • Interior Features: Built-in Features, Ceiling Fans(s), Central Vaccum, Crown Molding, Eat-in Kitchen, High Ceilings, Primary Bedroom Main Floor, Smart Home, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
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History:

DateListing TypeDays on yellowkeyMLS#EventPrice% Chg$/sqftSource
4/20/2026Rent41O6389081Back on yellowkey$13,500-1.4734MLS
3/10/2026Rent0O6389081listed for rent$13,500-1.4734MLS




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