MAJOR PRICE IMPROVEMENT! Discover your dream home in Winter Park - Boasting a total of 6,954 SF across three levels, this spacious residence on a tranquil street in the sought-after Vias is a haven for those seeking abundant living space. The first and second floors encompass 4,387 SF, featuring six bedrooms and four baths, while the basement adds 2,567 SF with one bedroom with an ensuite bathroom, a full bath in the hallway, a kitchenette/bar, gym, pool room, and more. Whether you envision a quiet retreat, a productive workspace, a game haven, a private hideaway, a workshop haven, an entertainment hub, or simply a place to live abundantly, this home has it all. The expansive first floor showcases a well-designed layout with a private main bedroom suite, a second bedroom suite, and a versatile open floor plan. The grand foyer separates the open living and dining areas, leading into the spacious family room/kitchen combo with a cozy gas fireplace. Natural wood floors adorn the first floor, complemented by French doors that open to the covered rear patio and pool deck. The main bedroom wing on the first floor is generously appointed, featuring a remodeled (2020) marble bathroom, a custom walk-in closet, and a convenient laundry closet with a full-size washer and dryer. The second floor unveils four bedrooms, two Jack-and-Jill baths with double sinks, a large laundry/utility room, and a studio/playroom. A custom built-in ladder leads to a third-floor bonus room with an air hockey table. The real surprise lies in the lower level—a fabulous and functional basement spanning 2,567 SF. This versatile space includes a private living area, an open kitchenette, a breakfast bar, an expansive bedroom with an en-suite bath, a gym, a workshop-ready room, a game room with a pool table, and a second full bathroom. Natural light streams in through large window wells, and a staircase leads up to the back patio/pool deck. Tucked away on a quiet circle just minutes from Park Ave and a few blocks from the Winter Park Racquet Club, this unforgettable gem is located in the desirable Dommerich/Maitland/WP High School district. This residence presents a remarkable opportunity to add your personal touches, allowing you to transform it into your dream home. Fulfill your lifestyle aspirations with this extraordinary Winter Park residence! Please ask for a measured floor plan to explore every detail of this extraordinary home.
Sold for $1,900,000
$1,900,000
1860 Via Contessa, Winter Park, FL 32789
7beds
6,854sqft
Single Family Residence
Built in 2003
0.27 Acres Lot
$2,531,800 Zestimate®
$277/sqft
$7,531 Estimated rent
Home value
$2,531,800
$2.28M - $2.86M
$7,531/mo
Zestimate® history
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$7,531/mo
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$7,531/mo
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$13,562/mo
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$13,562/mo
Est. payment
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Zillow last checked:
Listing updated:
Listing Provided by:
Audra Wilks 407-252-8582,
KELLER WILLIAMS WINTER PARK 407-545-6430
Bought with:
Derek Hovey, 3234014
EXP REALTY LLC
Source: Stellar MLS,MLS#: O6161682
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 7
- Bathrooms: 6
- Full bathrooms: 6
Primary bedroom
- Description: Room5
- Features: Ceiling Fan(s), En Suite Bathroom, Walk-In Closet(s)
- Level: First
- Dimensions: 20x15
Other
- Description: Room11
- Features: Ceiling Fan(s), En Suite Bathroom
- Level: Second
- Dimensions: 12x13.5
Bedroom 2
- Description: Room7
- Features: Ceiling Fan(s), En Suite Bathroom
- Level: First
- Dimensions: 15.5x10
Bedroom 3
- Description: Room8
- Features: Ceiling Fan(s), En Suite Bathroom
- Level: Second
- Dimensions: 15.5x10.5
Bedroom 4
- Description: Room9
- Features: Ceiling Fan(s), En Suite Bathroom
- Level: Second
- Dimensions: 15.5x10.5
Bedroom 5
- Description: Room10
- Features: Ceiling Fan(s), En Suite Bathroom
- Level: Second
- Dimensions: 12x14
Primary bathroom
- Description: Room6
- Features: Dual Sinks, Garden Bath, Granite Counters, Tub with Separate Shower Stall
- Level: First
- Dimensions: 11x13
Dining room
- Description: Room3
- Level: First
- Dimensions: 15x13
Family room
- Description: Room1
- Features: Ceiling Fan(s)
- Level: First
- Dimensions: 18.5x21.5
Game room
- Description: Room15
- Level: Basement
- Dimensions: 22.5x15
Great room
- Description: Room13
- Level: Basement
- Dimensions: 18x30
Kitchen
- Description: Room2
- Features: Breakfast Bar, Built-In Shelving, Granite Counters, Kitchen Island
- Level: First
- Dimensions: 16x17
Laundry
- Description: Room12
- Features: Built-In Shelving
- Level: Second
- Dimensions: 15.5x15
Living room
- Description: Room4
- Level: First
- Dimensions: 17x13
Workshop
- Description: Room14
- Level: Basement
- Dimensions: 13x26
Heating
- Central, Heat Pump
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Electric Water Heater, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Water Softener, Wine Refrigerator
- Laundry: Inside, Laundry Closet, Laundry Room, Upper Level
Features
- Ceiling Fan(s), Crown Molding, Dry Bar, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Open Floorplan, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
- Flooring: Carpet, Tile, Hardwood
- Doors: French Doors
- Windows: Blinds, Insulated Windows, Shutters
- Basement: Bath/Stubbed,Finished,Interior Entry
- Has fireplace: Yes
- Fireplace features: Family Room, Gas, Wood Burning
Interior area
- Total structure area: 9,162
- Total interior livable area: 6,854 sqft
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Garage Door Opener, Parking Pad
- Attached garage spaces: 2
- Has uncovered spaces: Yes
- Details: Garage Dimensions: 22x21
Features
- Levels: Three Or More
- Stories: 3
- Patio & porch: Covered, Front Porch, Porch, Rear Porch, Screened
- Exterior features: Irrigation System, Lighting, Rain Gutters
- Has private pool: Yes
- Pool features: Gunite, Heated, In Ground, Salt Water, Screen Enclosure
- Has spa: Yes
- Spa features: Heated, In Ground
- Fencing: Fenced,Vinyl,Wood
- Has view: Yes
- View description: Pool, Trees/Woods
Lot
- Size: 0.27 Acres
- Dimensions: 100 x 115
- Features: City Lot, Near Public Transit
- Residential vegetation: Trees/Landscaped
Details
- Parcel number: 322130528000180
- Zoning: R-1AA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Block, Concrete, Stucco, Wood Frame (FSC Certified)
- Foundation: Basement
- Roof: Concrete,Tile
Condition
- New construction: No
- Year built: 2003
Details
- Builder name: Parkland Homes
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Underground Utilities, Water Connected
Community & neighborhood
Location
- Region: Winter Park
- Subdivision: LUGANO TERRACE
HOA & financial
HOA
- Has HOA: No
Other fees
- Pet fee: $0 monthly
Other financial information
- Total actual rent: 0
Other
Other facts
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Road surface type: Paved, Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 3/9/2026 | Listing removed | $15,550$2/sqft |
Source: Zillow Rentals Report a problem | ||
| 1/19/2026 | Price change | $15,550-6%$2/sqft |
Source: Zillow Rentals Report a problem | ||
| 11/15/2025 | Listing removed | $2,875,000$419/sqft |
Source:  Stellar MLS #O6210791 Report a problem | ||
| 10/24/2025 | Price change | $16,550-5.7%$2/sqft |
Source: Zillow Rentals Report a problem | ||
| 10/4/2025 | Listed for sale | $2,875,000$419/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 10/1/2025 | Price change | $17,550-10%$3/sqft |
Source: Zillow Rentals Report a problem | ||
| 9/12/2025 | Listing removed | $2,875,000$419/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 9/9/2025 | Price change | $2,875,000+3%$419/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 8/25/2025 | Listed for rent | $19,500$3/sqft |
Source: Zillow Rentals Report a problem | ||
| 8/8/2025 | Price change | $2,790,000+1.5%$407/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 7/2/2025 | Price change | $2,750,000-1.6%$401/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 6/26/2025 | Price change | $2,795,000-2.8%$408/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 6/13/2025 | Price change | $2,875,000-0.9%$419/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 5/16/2025 | Price change | $2,900,000-1.7%$423/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 4/8/2025 | Price change | $2,950,000-1.3%$430/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 2/22/2025 | Listed for sale | $2,990,000+57.8%$436/sqft |
Source: Stellar MLS #O6210791 Report a problem | ||
| 10/8/2024 | Listing removed | $1,895,000-0.3%$276/sqft |
Source: Stellar MLS #O5963664 Report a problem | ||
| 5/31/2024 | Sold | $1,900,000-5%$277/sqft |
Source: Stellar MLS #O6161682 Report a problem | ||
| 4/20/2024 | Pending sale | $1,999,000$292/sqft |
Source: Stellar MLS #O6161682 Report a problem | ||
| 4/4/2024 | Price change | $1,999,000-11%$292/sqft |
Source: Stellar MLS #O6161682 Report a problem | ||
| 3/1/2024 | Price change | $2,245,000-6.3%$328/sqft |
Source: Stellar MLS #O6161682 Report a problem | ||
| 1/30/2024 | Price change | $2,395,000-4.2%$349/sqft |
Source: Stellar MLS #O6161682 Report a problem | ||
| 12/5/2023 | Listed for sale | $2,500,000+38.9%$365/sqft |
Source: Stellar MLS #O6161682 Report a problem | ||
| 10/8/2023 | Listing removed | -- |
Source: Stellar MLS #O5963664 Report a problem | ||
| 10/8/2021 | Sold | $1,800,000-5%$263/sqft |
Source: Public Record Report a problem | ||
| 9/3/2021 | Pending sale | $1,895,000$276/sqft |
Source: Stellar MLS #O5963664 Report a problem | ||
| 8/6/2021 | Listed for sale | $1,895,000+658.3%$276/sqft |
Source: Stellar MLS #O5963664 Report a problem | ||
| 9/1/1993 | Sold | $249,900$36/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $27,265 +3.4% | $1,784,949 +3% |
| 2023 | $26,363 +17.1% | $1,732,960 +19% |
| 2022 | $22,504 +50.3% | $1,456,492 +47.3% |
| 2021 | $14,973 -0.2% | $988,654 +1.4% |
| 2020 | $15,010 +0.7% | $975,004 +2.3% |
| 2019 | $14,912 +0.5% | $953,083 +1.9% |
| 2018 | $14,841 | $935,312 -23.1% |
| 2017 | $14,841 +0.8% | $1,216,926 +1.7% |
| 2016 | $14,722 +2% | $1,196,672 +4.9% |
| 2015 | $14,427 -3.2% | $1,141,133 +21.8% |
| 2014 | $14,902 +3.3% | $936,772 +8.8% |
| 2013 | $14,424 -2.1% | $861,009 -1.3% |
| 2012 | $14,731 -2.3% | $872,022 -1.9% |
| 2011 | $15,079 +2.8% | $888,514 -7.2% |
| 2010 | $14,662 | $957,572 -8.9% |
| 2009 | -- | $1,051,137 +1.8% |
| 2008 | $13,578 +2% | $1,032,531 -8.5% |
| 2007 | $13,307 -6.6% | $1,128,802 +29.1% |
| 2006 | $14,252 -0.2% | $874,618 +9.6% |
| 2005 | $14,282 +13.2% | $797,936 +15.4% |
| 2004 | $12,620 +138.4% | $691,293 +130.4% |
| 2003 | $5,294 +20.3% | $300,000 -13.7% |
| 2002 | $4,400 +0.4% | $347,569 +16.7% |
| 2001 | $4,381 +2.4% | $297,704 +11.5% |
| 2000 | $4,277 | $267,039 |
Find assessor info on the county website
Neighborhood: 32789
Nearby schools
GreatSchools rating
- 10/10Dommerich Elementary SchoolGrades: PK-5Distance: 1.3 mi
- 6/10Maitland Middle SchoolGrades: 6-8Distance: 1.4 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 2.3 mi
Schools provided by the listing agent
- Elementary: Dommerich Elem
- Middle: Maitland Middle
- High: Winter Park High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$2,531,800
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$2,531,800
- Florida
- Orange County
- Winter Park
- 32789
- 1860 Via Contessa
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