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1860 Via Contessa, 
Winter Park, FL 32789

$2,750,000


8

Beds


6

Baths


7,000

Sq Ft


Single Family

Active

Listed by

Sylvester Harding

Emmanuel Bart Williams

Sierra Realty Group LLC.

Last updated:

July 16, 2025, 04:34 PM

MLS#

O6210791

Source:

MFRMLS

About This Home

1860 Via Contessa

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.

Home Facts

Single Family

6 Baths

8 Bedrooms

Built in 2003

Price Summary

2,750,000

$392 per Sq. Ft.

MLS #:

O6210791

Last Updated:

July 16, 2025, 04:34 PM

Added:

a year ago


Rooms & Interior

Bedrooms

Total Bedrooms:

8

Bathrooms

Total Bathrooms:

6

Full Bathrooms:

6

Interior

Living Area:

7,000 Sq. Ft.


Structure

Structure

Building Area:

9,162 Sq. Ft.

Year Built:

2003


Lot

Lot Size (Sq. Ft):

11,531


Finances & Disclosures

Finances

Price:

$2,750,000

Price per Sq. Ft:

$392 per Sq. Ft.

MLS Logo
The information being provided by My Florida Regional MLS DBA Stellar MLS. is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS.. Sierra Realty Group LLC. is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Sierra Realty Group LLC., a broker participant of My Florida Regional MLS DBA Stellar MLS.. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by My Florida Regional MLS DBA Stellar MLS. and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Properties in listings may have been sold or may no longer be available. Copyright 2025 My Florida Regional MLS DBA Stellar MLS.. All rights reserved.

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