Winter Park

Winter Park, a charming city that is home to over 30,000 individuals, lies just to the north of Orlando within Orange County, Florida. Acknowledged for its elegance, Winter Park is renowned for its majestic trees, a wealth of green parks, streets lined with brick, magnificent residences, a variety of museums, dynamic lakes, and the renowned Park Avenue boutiques.


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Real Estate Statistics

Average Price $1.3M
Lowest Price $200K
Highest Price $9M
Total Listings 374
Avg. Days On Market 91
Avg. Price/SQFT $459

Property Types (active listings)

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New Open House
2681 Fitzhugh Road, WINTER PARK

$750,000

2681 Fitzhugh Road, WINTER PARK

4 Beds 3 Baths 2,375 SqFt Residential
Sat, Apr 18th, 2026 @ 1pm - 3pm
MLS® # O6383699
New Open House
1661 Woodland, WINTER PARK

$1,300,000

1661 Woodland, WINTER PARK

0 Beds 0 Baths 0 SqFt Land
Sat, Apr 18th, 2026 @ 1pm - 3pm
MLS® # O6399334
New Open House
1905 Bonanza Ct, WINTER PARK

$490,000

1905 Bonanza Ct, WINTER PARK

4 Beds 2 Baths 1,774 SqFt Residential
Sun, Apr 19th, 2026 @ 11am - 1pm
MLS® # O6398772
New Open House
2361 Mulbry Drive, WINTER PARK

$2,395,000

2361 Mulbry Drive, WINTER PARK

4 Beds 4 Baths 3,111 SqFt Residential
Sat, Apr 18th, 2026 @ 12pm - 2pm
MLS® # O6396840
New Open House
1661 Woodland Avenue, WINTER PARK

$1,300,000

1661 Woodland Avenue, WINTER PARK

3 Beds 4 Baths 3,215 SqFt Residential
Sat, Apr 18th, 2026 @ 1pm - 3pm
MLS® # O6399348
New
3720 Jonquil Lane, WINTER PARK

$445,000

3720 Jonquil Lane, WINTER PARK

3 Beds 2 Baths 1,647 SqFt Residential MLS® # O6399628
New
7454 Wynnewood Square 188, WINTER PARK

$229,000

7454 Wynnewood Square 188, WINTER PARK

3 Beds 3 Baths 1,151 SqFt Residential MLS® # O6386578
New
1785 Walnut Avenue, WINTER PARK

$825,000

1785 Walnut Avenue, WINTER PARK

0 Beds 0 Baths 0 SqFt Land MLS® # O6399577
New
1441 Cardinal Court, WINTER PARK

$4,285,000

1441 Cardinal Court, WINTER PARK

4 Beds 6 Baths 4,066 SqFt Residential MLS® # O6399395
New Open House
3172 Crown Jewel Court, WINTER PARK

$339,900

↑ $900

3172 Crown Jewel Court, WINTER PARK

3 Beds 3 Baths 1,406 SqFt Residential
Sat, Apr 18th, 2026 @ 11am - 1pm
MLS® # O6397498
New
5330 Tangerine Avenue, WINTER PARK

$354,900

5330 Tangerine Avenue, WINTER PARK

3 Beds 2 Baths 1,642 SqFt Residential MLS® # O6399019
New Open House
5143 Lazy Oaks Drive 5143, WINTER PARK

$285,000

5143 Lazy Oaks Drive 5143, WINTER PARK

2 Beds 2 Baths 1,008 SqFt Residential
Sat, Apr 18th, 2026 @ 12pm - 2pm
MLS® # O6398856

     


More About Winter Park

This jewel of Florida, officially incorporated in 1887, was initially conceived as a winter sanctuary for affluent individuals from the North who were in search of a get-away from the severe winter months and a serene environment to unwind. Throughout its history, Winter Park has successfully preserved its picturesque natural charm.

Initially known as Lakeview in 1858, and later rebranded as Osceola in 1870, the city received its current name, Winter Park, in 1881. Founding figures Loring Chase and Oliver Chapman, during a casual conversation, opted for a name that conveyed the vision of a 'park in the winter', which led to the selection of the city's present name.

Originally, visitors were drawn to Winter Park for its picturesque lakes, pleasant climate, and verdant surroundings. Presently, they continue to find allure in these natural features, enhanced by an array of excellent dining options, cultural museums, lively entertainment, theatrical offerings, a host of outdoor activities, and numerous festivals.

COMMUNITY IS EVERYTHING

Winter Park captivates both visitors and residents with its exquisite chain of lakes that serve as the city's aquatic heart. These sparkling waters are not just a backdrop for beautiful homes and meticulous landscaping but are also centers for recreation and leisure activities such as boating, paddleboarding, and scenic boat tours that showcase the area's natural setting and stunning architecture.

Established in 1885 by New England Congregationalists aspiring to replicate their brand of liberal arts education in Florida, Rollins College is recognized as the state's oldest college and a premier institution for liberal arts in the nation. As a distinguished educational establishment, Rollins has produced an impressive roster of scholars, including recipients of Rhodes, Fulbright, Goldwater, and Truman Scholarships, alongside a Nobel Prize winner. Celebrated by Time Magazine and consistently ranked by U.S. News & World Report as one of "America's Best Colleges," Rollins College upholds a legacy of academic excellence.

Winter Park’s signature landmarks include its extensive network of lakes, dense canopy of trees, characteristic bricked streets, the quaint Park Avenue shopping area, and educational cornerstone Rollins College. In the city's center lies Central Park, a sprawling green space with majestic trees, approachable wildlife, and welcoming benches, gifted to Winter Park by influential early resident Charles Hosmer Morse. Additionally, the city is known for hosting the acclaimed Winter Park Sidewalk Art Festival, annually attracting over a quarter-million visitors to Central Park to experience premier art and music.

Spanning a 10-square-mile area and resting at an average elevation of 100 feet, the city continues to evolve while maintaining its unique historical and cultural charm.

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