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Matthew McLean
(386) 585-5571 Matthew@shorelinedaytona.com
  • 340 South Beach Street Suite 124
    Daytona Beach, FL 32114
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Lakeside College Town Near Orlando

For Sale in Winter Park, FL

Welcome to Winter Park, the Orange County city of tree-lined Park Avenue, Rollins College, and a chain of lakes just north of downtown Orlando.

Winter Park sits in Orange County, Florida, immediately north of downtown Orlando, and is widely regarded as one of the region's most distinctive cities. It was conceived in the late 19th century as a winter resort for Northerners arriving by rail, and its identity still flows from that origin — a planned community of lakes, tree-lined streets, and a walkable commercial avenue built around the railroad. Its population is about 30,000. The city's defining institutions are Rollins College and Park Avenue. Rollins, founded in 1885, is the oldest college in Florida, and its 70-acre campus of Spanish and Mediterranean Revival architecture sits directly across from Park Avenue, the city's central shopping and dining street. Together they give Winter Park an academic, cultured atmosphere unusual for a city of its size, with a steady presence of students, faculty, and visitors. Water is central to the city's geography. The Winter Park Chain of Lakes — six lakes connected by narrow canals — cuts through the community, creating a boating and paddling culture and shaping its lakefront neighborhoods. Many streets are shaded by ancient live oaks and moss-draped trees, reinforcing the garden-city feel that first drew the city's founders. Winter Park functions as an established, close-in suburb of Orlando. SunRail commuter rail and Amtrak stop at its station, linking the city to downtown Orlando and the wider region, while Interstate 4 runs nearby. Public schools belong to Orange County Public Schools, one of the nation's largest districts, anchored locally by Winter Park High School. The city suits households drawn to historic homes, lake access, a walkable downtown, and rail access to Orlando, who value character and culture over new-construction sprawl.

Population 29,795
County Orange County
Active Listings 606
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Frequently Asked Questions

What county is Winter Park in?

Winter Park is located in Orange County, Florida, just north of downtown Orlando. It covers about 10.2 square miles, with a significant portion of its area made up of the Winter Park Chain of Lakes.

What college is located in Winter Park?

Winter Park is home to Rollins College, a private liberal arts college founded in 1885 and the oldest college in Florida. Its 70-acre campus, known for Spanish and Mediterranean Revival architecture, sits directly across from the city's Park Avenue district.

Does Winter Park have a train station?

Yes. The Winter Park station is served by SunRail commuter rail, which links the city to downtown Orlando and points across Central Florida, and by Amtrak's Floridian and Silver Meteor intercity trains, making rail access a defining feature of the city.

What is Park Avenue in Winter Park?

Park Avenue is Winter Park's central shopping and dining street, running alongside the Rollins College campus. It is known for its boutiques, cafés, restaurants, and seasonal events, and serves as the city's main gathering place.

What are the Winter Park Chain of Lakes?

The Winter Park Chain of Lakes is a series of six interconnected lakes joined by narrow canals, popular for paddleboarding, kayaking, boating, and fishing. The lakes sit near the heart of the city and anchor its waterside culture.

MARKET SNAPSHOT

The Market at a Glance

How homes have been selling here over the last 90 days.

home_work New This Week 34
Went Under Contract 0
trending_down Price Reductions 0
payments Median Sale Price $508,750 +6.2%
square_foot Price per Sq Ft $302
schedule Avg Days on Market 57
sell Homes Sold 278
percent Sale-to-List Ratio 98.0%
inventory_2 Months of Inventory 4.6

Price & Sales History

Market data reflects closed sales over the last 90 days and is provided for informational purposes.

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Zip Codes

Browse listings by postal code in this area.

320031 home for saleMedian sale$330.9KPer sq ft$762 sales in the last 90 days
320095 homes for saleMedian sale$447KPer sq ft$1862 sales in the last 90 days
320401 home for saleMedian sale$1.7MPer sq ft$3211 sale in the last 90 days
320431 home for saleMedian sale$350KPer sq ft$1355 sales in the last 90 days
320464 homes for saleMedian sale$275KPer sq ft$1861 sale in the last 90 days
320631 home for saleMedian sale$229.8KPer sq ft$951 sale in the last 90 days
320651 home for saleMedian sale$247.5KPer sq ft$534 sales in the last 90 days
320805 homes for saleMedian sale$613.8KPer sq ft$53218 sales in the last 90 days
320822 homes for saleMedian sale$864KPer sq ft$2964 sales in the last 90 days
320846 homes for saleMedian sale$267KPer sq ft$23633 sales in the last 90 days
320861 home for saleMedian sale$244KPer sq ft$1619 sales in the last 90 days
320911 home for saleMedian sale$270KPer sq ft$1416 sales in the last 90 days
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2008 Houndslake Drive For Sale $490,000
2008 Houndslake Drive
Winter Park, FL 32792
4 Beds 2 Baths 2250 Sq Ft Built 1980 1227585
1

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