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WINTER PARK, FL 32789 1860 VIA CONTESSA

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Presented By: KELLY PRICE & COMPANY LLC with 407-645-4321. - 407-645-4321
  • MLS# O6389081
  • 03/10/2026
  • Request Tour
  • Request Info
  • Beds • 8
  • Baths • 6
  • SQFT • 7,000
  • Garage • 2

Home Details

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.
Presented By: KELLY PRICE & COMPANY LLC with 407-645-4321. - 407-645-4321

Interior Features for 1860 VIA CONTESSA

Bedrooms

Total Bedrooms8

Bathrooms

Half Baths0
Total Baths6

Other Interior Features

Air Conditioning Y/NYes
FlooringCeramic Tile, Porcelain Tile, Tile, Hardwood
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesBuilt-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)
Laundry FeaturesLaundry Room

General for 1860 VIA CONTESSA

AppliancesBuilt-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Wine Refrigerator
Attached Garage Yes
Availability Date2026-03-09
Building Area UnitsSquare Feet
Carport Y/NNo
CityWINTER PARK
CoolingCentral Air, Zoned
CountyOrange
DirectionsFrom Howell Branch and Temple: Head South on Temple Drive. Make a right onto Via Contessa. House is on the right hand side.
Elementary SchoolDommerich Elem
Full Baths6
Garage Spaces2
Garage Y/NYes
HeatingCentral, Electric
High SchoolWinter Park High
ILS Total SQFT2000
ILS Under Air SQFT2000
Lease Amount FrequencyMonthly
LevelsThree Or More
Living Area UnitsSquare Feet
Lot Size Square Feet11531
Lot Size UnitsSquare Feet
MLS Area32789 - Winter Park
Middle/Junior High SchoolMaitland Middle
New ConstructionNo
Occupancy TypeVacant
Ok to Lease12 Months
OwnerPaysGrounds Care, Pool Maintenance
Pet Size LimitSmall (16-35 Lbs.)
Pets AllowedYes
Pool FeaturesIn Ground
Property SubtypeSingle Family Residence
Property TypeResidential Lease
STELLAR_InLawSuiteDescrip2+ Bathrooms, 2+ Bedrooms, Attached
STELLAR_InLawSuiteYNYes
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameLUGANO TERRACE
Total Rooms15
UtilitiesCable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Street Lights
Water Access Y/NNo
Water View Y/NNo
Year Built2003

Exterior for 1860 VIA CONTESSA

Building Area Total9162
Covered Spaces2
Lot Size Acres0.26
Lot Size Area11531
Private PoolYes
Road Surface TypePaved
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Steven Silcock

Broker Owner
Price $13,500
MLS#O6389081
List Date 03/10/2026
Property Type Rentals
Phone 407.574.0218
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Request Info
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