$2,790,000
$290K PRICE INCREASE

1860 Via Contessa Winter Park, FL 32789

Estimated payment $17,399/month

Total Views 14,551
8 Beds
6 Baths
7,000 Sq Ft
$399 Price per Sq Ft

Highlights

  • Oak Trees
  • Screened Pool
  • Deck
  • Dommerich Elementary School Rated A
  • Open Floorplan
  • Family Room with Fireplace

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.

Listing Agent

Sylvester Harding

SIERRA REALTY GROUP LLC Brokerage Phone: 407-557-3119 License #3176631 Listed on: 06/02/2024

Co-Listing Agent

Emmanuel Bart Williams

SIERRA REALTY GROUP LLC Brokerage Phone: 407-557-3119 License #3440976

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $26,363

Year Built

  • Built in 2003

Lot Details

  • 0.26 Acre Lot
  • North Facing Home
  • Vinyl Fence
  • Mature Landscaping
  • Irrigation Equipment
  • Oak Trees
  • Property is zoned R-1AA

Parking

  • 2 Car Attached Garage
  • Oversized Parking
  • Garage Door Opener

Home Design

  • Bi-Level Home
  • Block Foundation
  • Stem Wall Foundation
  • Tile Roof
  • Block Exterior
  • Stucco

Interior Spaces

  • 7,000 Sq Ft Home
  • Open Floorplan
  • Built-In Features
  • Bar Fridge
  • Crown Molding
  • High Ceiling
  • Ceiling Fan
  • Gas Fireplace
  • Double Pane Windows
  • ENERGY STAR Qualified Windows
  • Insulated Windows
  • Shades
  • Blinds
  • Solar Screens
  • French Doors
  • Sliding Doors
  • Family Room with Fireplace
  • Great Room
  • Living Room with Fireplace
  • Breakfast Room
  • Formal Dining Room
  • Den
  • Loft
  • Bonus Room
  • Inside Utility
  • Attic
  • Finished Basement

Kitchen

  • Eat-In Kitchen
  • Built-In Convection Oven
  • Cooktop with Range Hood
  • Recirculated Exhaust Fan
  • Microwave
  • Dishwasher
  • Wine Refrigerator
  • Stone Countertops
  • Solid Wood Cabinet
  • Disposal

Flooring

  • Wood
  • Ceramic Tile

Bedrooms and Bathrooms

  • 8 Bedrooms
  • Primary Bedroom on Main
  • Split Bedroom Floorplan
  • Walk-In Closet
  • In-Law or Guest Suite
  • 6 Full Bathrooms

Laundry

  • Laundry Room
  • Dryer
  • Washer

Home Security

  • Security System Owned
  • Smart Home
  • Fire and Smoke Detector

Eco-Friendly Details

  • Energy-Efficient HVAC
  • Energy-Efficient Insulation
  • Energy-Efficient Thermostat

Pool

  • Screened Pool
  • Heated In Ground Pool
  • In Ground Spa
  • Gunite Pool
  • Fence Around Pool
  • Outdoor Shower
  • Pool Tile
  • Pool Lighting

Outdoor Features

  • Deck
  • Enclosed Patio or Porch
  • Exterior Lighting
  • Rain Gutters

Additional Homes

  • 2,000 SF Accessory Dwelling Unit

Utilities

  • Forced Air Zoned Heating and Cooling System
  • Heat Pump System
  • Thermostat
  • Underground Utilities
  • Natural Gas Connected
  • Tankless Water Heater
  • Gas Water Heater
  • Cable TV Available

Community Details

  • No Home Owners Association
  • Lugano Terrace Subdivision

Listing and Financial Details

Home Details

Home Type

Single Family

Est. Annual Taxes

$26,363

Year Built

Built in 2003

Lot Details

0

Parking

2

Listing Details

  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Construction Materials: Block, Stucco
  • Fireplace: No
  • Living Area: 7000
  • Lot Size Acres: 0.26
  • New Construction: No
  • Year Built: 2003
  • Building Area Total: 9162
  • Lot Size Sq Ft: 11531
  • Directions to Property: FL-426 W; Turn right onto Bear Gully Rd; Turn left to stay on Bear Gully Rd; At the traffic circle, continue straight to stay on Bear Gully Rd; Turn right onto Howell Branch Rd; Turn left onto Temple Dr; Turn right onto Vía Lugano; Turn right onto Vía Contessa; House is on the right.
  • Status: Active
  • Co List Office Mls Id: MFR50957
  • Co List Office Phone: 407-557-3119
  • Ownership: Fee Simple
  • Available for Lease YN: 1
  • Escrow City: Celebration
  • Escrow Postal Code: 34747
  • Escrow State: FL
  • Escrow Street Name: Sycamore Street Suite 190
  • Escrow Street Number: 610
  • List Office Head Office Key Nume: 1050223
  • Minimum Lease: No Minimum
  • RATIO Current Price By Calculate: 398.57
  • Total Acreage: 1/4 to less than 1/2
  • Unit Number YN: 0
  • Water Access YN: 0
  • MFR_InLawSuiteYN: 1
  • MFR_DockYN: 0
  • MFR_InLawSuiteDescription: 2+ Bathrooms,2+ Bedrooms,Attached,Kitchenette,Private Entrance
  • MFR_InLawSuiteUnderAirSqFt: 2000.00
  • Attribution Contact: 407-557-3119
  • Tax Year: 2023
  • Special Features: VirtualTour

Interior Features

  • Fireplace Features: Family Room, Gas, Living Room
  • Living Area Units: Square Feet
  • Flooring: Ceramic Tile, Tile, Wood
  • Full Bathrooms: 6
  • Interior Amenities: Built-in Features, Ceiling Fans(s), Central Vaccum, Crown Molding, Eat-in Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Smart Home, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
  • Appliances Included: Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
  • Foundation Details: Basement, Block, Stem Wall
  • Total Bedrooms: 8
  • Levels: Two
  • Other Equipment: Irrigation Equipment
  • Spa Features: In Ground
  • Spa Yn: Yes
  • Window Features: Blinds, Double Pane Windows, ENERGY STAR Qualified Windows, Insulated Windows, Low-Emissivity Windows, Shades, Solar Screens
  • Street Number Modifier: 1860
  • Has Basement: Finished
  • Additional Rooms: Attic,Bonus Room,Breakfast Room Separate,Den/Library/Office,Family Room,Formal Dining Room Separate,Formal Living Room Separate,Inside Utility,Interior In-Law Suite w/Private Entry,Loft
  • Living Area Meters: 650.32
  • Room Count: 15

Exterior Features

  • Direction Faces: North
  • Pool Features: Gunite, Heated, In Ground, Lighting, Screen Enclosure, Tile
  • Exterior Features: French Doors, Lighting, Outdoor Shower, Rain Gutters, Sidewalk, Sliding Doors
  • Roof: Tile
  • Home Warranty: No
  • Pool Private: Yes
  • Waterfront: No
  • Patio and Porch Features: Covered, Deck, Enclosed, Front Porch, Patio, Porch, Rear Porch, Screened
  • Road Surface Type: Asphalt, Paved
  • Water Extras YN: 0
  • Water View YN: 0
  • Waterfront Feet Total: 0
  • Flood Zone Date: 2009-09-25
  • Flood Zone Panel: 12095C0255F

Garage/Parking

  • Attached Garage: Yes
  • Carport Y N: No
  • Garage Spaces: 2
  • Garage Yn: Yes
  • Parking Features: Garage Door Opener, Oversized

Utilities

  • Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Underground Utilities, Water Connected
  • Cooling: Central Air, Zoned
  • Heating: Central, Electric, Heat Pump, Zoned
  • Laundry Features: Electric Dryer Hookup, Gas Dryer Hookup, Inside, Laundry Room
  • Sewer: Public Sewer
  • Water Source: Public

Condo/Co-op/Association

  • Community Features: Street Lights
  • Association: No
  • Security: Closed Circuit Camera(s), Fire Alarm, Security System, Security System Owned, Smoke Detector(s)
  • Senior Community: No
  • Association 2 YN: 0

Fee Information

  • Total Annual Fees: 0.00
  • Total Monthly Fees: 0.00

Lot Info

  • Zoning: R-1AA
  • Parcel Number: 32-21-30-5280-00-180
  • Additional Parcels: No
  • Fencing: Fenced, Vinyl
  • Lot Features: City Limits, Landscaped, Paved
  • Flood Zone Code: X
  • Homestead YN: 1
  • Lot Size Square Meters: 1071

Green Features

  • Efficiency: HVAC, Insulation, Thermostat
  • Green Verification Count: 0

Rental Info

  • Furnished: Unfurnished
  • Pets Allowed: Yes
  • Lease Restrictions YN: 0

Tax Info

  • Tax Annual Amount: 26363
  • Tax Block: 00
  • Tax Book Number: W-4
  • Tax Lot: 18

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $27,265 $2,139,320 $660,000 $1,479,320
2024 $26,363 $2,070,950 $660,000 $1,410,950
2023 $26,363 $1,732,960 $0 $0
2022 $22,504 $1,456,492 $500,000 $956,492
2021 $14,973 $988,654 $0 $0
2020 $14,409 $975,004 $0 $0
2019 $14,912 $953,083 $0 $0
2018 $14,841 $935,312 $0 $0
2017 $14,722 $1,216,926 $476,100 $740,826
2016 $14,427 $1,196,672 $476,100 $720,572
2015 $14,773 $1,141,133 $414,000 $727,133
2014 -- $936,772 $375,000 $561,772
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
08/10/2025 08/10/25 Price Changed $19,500 0.0% $3 / Sq Ft
08/08/2025 08/08/25 Price Changed $2,790,000 0.0% $399 / Sq Ft
08/01/2025 08/01/25 For Rent $18,000 0.0% --
07/30/2025 07/30/25 Off Market $18,000 -- --
07/02/2025 07/02/25 Price Changed $2,750,000 -1.6% $393 / Sq Ft
06/26/2025 06/26/25 Price Changed $2,795,000 -2.8% $399 / Sq Ft
06/13/2025 06/13/25 Price Changed $2,875,000 -0.9% $411 / Sq Ft
05/16/2025 05/16/25 Price Changed $2,900,000 -1.7% $414 / Sq Ft
04/08/2025 04/08/25 Price Changed $2,950,000 -1.3% $421 / Sq Ft
02/22/2025 02/22/25 For Sale $2,990,000 +3.1% $427 / Sq Ft
06/02/2024 06/02/24 Off Market $2,900,000 -- --
06/02/2024 06/02/24 Pending -- -- --
06/02/2024 06/02/24 Price Changed $2,900,000 +16.0% $414 / Sq Ft
06/02/2024 06/02/24 For Sale $2,500,000 +31.6% $357 / Sq Ft
05/31/2024 05/31/24 Sold $1,900,000 -5.0% $277 / Sq Ft
04/17/2024 04/17/24 Pending -- -- --
04/04/2024 04/04/24 Price Changed $1,999,000 -11.0% $292 / Sq Ft
03/07/2024 03/07/24 Price Changed $2,245,000 -6.3% $328 / Sq Ft
01/30/2024 01/30/24 Price Changed $2,395,000 -4.2% $349 / Sq Ft
12/05/2023 12/05/23 For Sale $2,500,000 +38.9% $365 / Sq Ft
10/07/2021 10/07/21 Sold $1,800,000 -5.0% $263 / Sq Ft
09/02/2021 09/02/21 Pending -- -- --
08/06/2021 08/06/21 For Sale $1,895,000 -- $276 / Sq Ft
Source: Stellar MLS

Purchase History

Date Type Sale Price Title Company
Warranty Deed $100 None Listed On Document
Warranty Deed $1,900,000 None Listed On Document
Warranty Deed $1,800,000 Attorney
Warranty Deed $249,900 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $1,627,793 Construction
Previous Owner $1,200,000 New Conventional
Previous Owner $150,000 Credit Line Revolving
Previous Owner $801,375 New Conventional
Previous Owner $174,930 No Value Available
Source: Public Records

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Source: Stellar MLS

MLS Number: O6210791

Stellar MLS

APN: 32-2130-5280-00-180