House for rent

5+ Days Ago

1860 Via Contessa
1860 Via Contessa, Winter Park, FL 32789, USA

Monthly rent	$13,500
Beds	8
Baths	6
Sqft	7,000

Monthly rent	$13,500
Beds	8
Baths	6
Sqft	7,000

5+ Days Ago

Highlights

French doors
Gas fireplace
Breakfast bar
Open-concept floor plan
Game room
Pool deck

Location

1860 Via Contessa, Winter Park, FL 32789, USA

Tour 1860 Via Contessa

Contact

Kelly Price

Kelly Price & Company

(407) 645-4321

Property Overview

1860 Via Contessa offers notable features such as French doors, a gas fireplace, and an open-concept floor plan, enhancing its aesthetic and functional appeal. Pros include proximity to grocery stores and public transport within a mile, along with a top-rated middle school nearby. The property is ideal for those focused on fitness and wellness, featuring an on-site fitness center, ample natural lighting, and a pool area.

Things you’ll love

Middle school nearby
Fireplace
Images Available

Great for

Wellness

Amenities for 1860 Via Contessa

Features

Ceiling Fan	Central Air
Electric Heating	Fifteen Rooms
Fireplace	Hardwood Floor
High Ceilings	Loft
Walk-in Closet

Appliances

Dishwasher

In-Unit Laundry

Community

Fitness Center

Onsite Laundry

Grounds

Garage Parking

Swimming Pool

Other

Zoned

Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.

Policies and fees

Applicants

One-time.

Contact Property

REQUIRED FEES

Security Deposit

One-time. Refundable.

Contact Property

About 1860 Via Contessa

Home

Houses in Winter Park

1860 Via Contessa, Winter Park, FL 32789, USA

Property Status: Active 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. Office Phone: (407) 645-4321 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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Property highlights

How 1860 Via Contessa, Winter Park, FL 32789, USA compares to other nearby properties.

Positives

Middle school nearby: There is a middle school 1 mile away
Fireplace: Upgraded in-unit features
Images Available: There are at least 10 photos of this address
Laundry available on site: Washers and dryers are available in-building or in-unit
Walk-in closet: More closet space on average

Address details

Zip code	32789
Type	House for rent

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Rent trends in Winter Park

Median rents as of Mar 21 2026.

Winter Park

A table of 4-bedroom apartment rental data trends in Winter Park
Month	Median Rent
April 2024	$4,537
May 2024	$4,591
June 2024	$3,958
July 2024	$3,525
August 2024	$3,400
September 2024	$3,062
October 2024	$2,999
November 2024	$3,619
December 2024	$3,350
January 2025	$3,260
February 2025	$3,033
March 2025	$3,160
April 2025	$3,187
May 2025	$3,275
June 2025	$3,612
July 2025	$4,649
August 2025	$6,642
September 2025	$5,359
October 2025	$4,464
November 2025	$4,355
December 2025	$4,087
January 2026	$4,541
February 2026	$4,494
March 2026	$4,595

Check availability

Rent history

Check out the past listing prices for monthly rent at 1860 Via Contessa, Winter Park, FL.
			Bath
2 months ago	$16,550	8 bed	6 bath
4 months ago	$16,550	8 bed	6 bath
6 months ago	$19,500	8 bed	6 bath

Schools near 1860 Via Contessa

Internet available near 1860 Via Contessa

Neighborhood

NEIGHBORHOOD VIBE

Peaceful and quiet

Noise-canceling headphones not required in this mostly noise free area.

Getting around Winter Park near 1860 Via Contessa

Walking

5/10

Some shops and stores are within a few minutes.

Driving

8/10

Commuting is easy with multiple accessible routes and plenty of parking.

Cycling

4/10

More spots are within biking distance and some roads are cyclist-friendly.

Transit

1/10

FYI, there are little to no public transit options within walking distance.

Points of interest for 1860 Via Contessa, Winter Park

Groceries

2/10

Closest supermarket further than a 30-minute walk

Shopping

6/10

Several shops within walking distance

Cafes

3/10

Some cafés within walking distance

Restaurants

5/10

Some restaurants within a few minutes’ walk

Primary schools

3/10

At least one elementary school within a 30-minute walk

High schools

0/10

Closest high school further than a 30-minute walk

Parks

6/10

Moderate amount of park space nearby

Nightlife

2/10

Few or no bars within walking distance

Explore the area around 1860 Via Contessa

Sprouts Farmers Market

1999 Aloma Ave

Publix

2295 Aloma Ave

Publix

1455 State Road 436

Artlife Foodjoy Inc

210 E Morse Blvd

Fancy Fruit & Produce

1442 State Road 436

Other units at this address

1860 Via Contessa, Winter Park, FL

1860 Via Contessa Winter Park, FL

Occupied

NA

8 Beds

6 Baths

7,000 sqft

$16,550

Air Conditioning • Assigned Parking • Fireplace • Hardwood Floor • In-Unit Laundry • On-Site Laundry

Listed by Sierra Realty Group, LLC

Days on market: 118

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, thishome 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’ playtim eor 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