Winter Park, FL
Homes For Sale & Real Estate Listings

See Winter Park FL homes for sale and learn about the community.

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View real estate listings in Winter Park, FL

12 results

450 LAKEWOOD DRIVE, WINTER PARK, FL, US, 32789

$2,500,000
450 LAKEWOOD DRIVE, WINTER PARK, FL, US, 32789

Sophisticated Lakeside Living in the Heart of Winter Park! Experience...

5 beds
4 baths
6522 sq ft
450 LAKEWOOD DRIVE, WINTER PARK, FL, US, 32789

7484 CANFORD COURT UNIT 8, WINTER PARK, FL, US, 32792

$250,000
7484 CANFORD COURT UNIT 8, WINTER PARK, FL, US, 32792

This three-bedroom, three-bath updated Winter Park townhome-style condo is located...

3 beds
2 baths
1578 sq ft
7484 CANFORD COURT UNIT 8, WINTER PARK, FL, US, 32792

5331 OAK COURT, WINTER PARK, FL, US, 32792

$460,000
5331 OAK COURT, WINTER PARK, FL, US, 32792

Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home...

3 beds
2 baths
1815 sq ft
5331 OAK COURT, WINTER PARK, FL, US, 32792

1523 MILLER AVENUE, WINTER PARK, FL, US, 32789

$1,499,999
1523 MILLER AVENUE, WINTER PARK, FL, US, 32789

BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. This 3,164...

5 beds
4 baths
3970 sq ft
1523 MILLER AVENUE, WINTER PARK, FL, US, 32789

7794 COUNTRY PLACE UNIT 2, WINTER PARK, FL, US, 32792

$239,900
7794 COUNTRY PLACE UNIT 2, WINTER PARK, FL, US, 32792

Winter Park Clean, UPDATED and in Move In Condition –...

2 beds
2 baths
1068 sq ft
7794 COUNTRY PLACE UNIT 2, WINTER PARK, FL, US, 32792

1441 CARDINAL COURT, WINTER PARK, FL, US, 32789

$4,285,000
1441 CARDINAL COURT, WINTER PARK, FL, US, 32789

Beautifully built in 2022 by Lonnie Richardson, this custom one-story...

4 beds
5 baths
5545 sq ft
1441 CARDINAL COURT, WINTER PARK, FL, US, 32789

1108 FAIRWAY DRIVE, WINTER PARK, FL, US, 32792

$714,900
1108 FAIRWAY DRIVE, WINTER PARK, FL, US, 32792

Offering 25k BELOW appraised value!! Buyer financing fell through, act...

3 beds
2 baths
2370 sq ft
1108 FAIRWAY DRIVE, WINTER PARK, FL, US, 32792

1354 INDIANA AVENUE, WINTER PARK, FL, US, 32789

$589,900
1354 INDIANA AVENUE, WINTER PARK, FL, US, 32789

One or more photo(s) has been virtually staged. Fabulous location...

3 beds
2 baths
1419 sq ft
1354 INDIANA AVENUE, WINTER PARK, FL, US, 32789

7336 FOREST HILL COURT UNIT 240, WINTER PARK, FL, US, 32792

$169,900
7336 FOREST HILL COURT UNIT 240, WINTER PARK, FL, US, 32792

Updated Winter Park Townhome!! If you are looking for LOCATION...

2 beds
1 bath
990 sq ft
7336 FOREST HILL COURT UNIT 240, WINTER PARK, FL, US, 32792

1760 LEGION DRIVE, WINTER PARK, FL, US, 32789

$2,295,000
1760 LEGION DRIVE, WINTER PARK, FL, US, 32789

Winter Park 1964 Charmer! This wonderful ranch is located just...

4 beds
5 baths
6149 sq ft
1760 LEGION DRIVE, WINTER PARK, FL, US, 32789

1927 ELAND AVENUE, WINTER PARK, FL, US, 32789

$825,000
1927 ELAND AVENUE, WINTER PARK, FL, US, 32789

*Ask about a lender provided credit up to $12,500 on...

5 beds
3 baths
2899 sq ft
1927 ELAND AVENUE, WINTER PARK, FL, US, 32789

311 E MORSE BOULEVARD UNIT 7-5, WINTER PARK, FL, US, 32789

$359,000
311 E MORSE BOULEVARD UNIT 7-5, WINTER PARK, FL, US, 32789

Major Price Improvement! Here is your rare opportunity to own...

1 bed
1 bath
482 sq ft
311 E MORSE BOULEVARD UNIT 7-5, WINTER PARK, FL, US, 32789
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Neighborhood Profile: Winter Park, FL

Winter Park FL train station
Image via Meloaraujo

Just a short drive northeast of downtown Orlando lies Winter Park, FL—a vibrant yet peaceful community that blends historic charm, natural beauty, and modern living.

Known for its scenic lakes, cobblestone streets, and rich cultural offerings, Winter Park feels like a hidden gem with the perks of a big city just minutes away.

A Community Steeped in Charm

Winter Park was originally founded as a winter resort for wealthy Northerners in the late 1800s, and that sense of timeless elegance is still felt today. Stately oaks draped in Spanish moss line the roads, while historic homes and Mediterranean-style architecture evoke a sense of tradition and care.

The city is home to Rollins College, a prestigious liberal arts school situated along the shores of Lake Virginia. Its presence adds a youthful, energetic feel to the community and supports a walkable, cultural downtown district that’s rich in history and beautifully maintained.

Homes That Match Every Stage of Life

Whether you’re a first-time buyer, growing family, or looking to downsize into a quieter lifestyle, Winter Park offers a wide range of housing options. You’ll find:

  • Charming bungalows and updated mid-century homes on quiet, tree-canopied streets
  • Modern condos and townhomes with walkable access to shops and restaurants
  • Luxury estates and waterfront homes along the Winter Park Chain of Lakes

    house in Winter Park FL

    Many homes in the area reflect a blend of old and new, often combining classic architectural details with modern updates and energy-efficient features.

    Outdoor Living & Community Vibes

    Winter Park is a paradise for anyone who loves the outdoors. With more than 70 parks, multiple public lakes, and plenty of walking trails, it’s easy to enjoy Florida’s sunshine year-round. Central Park, located in the heart of downtown, is a popular spot for weekend markets, music festivals, and community gatherings.

    For water lovers, the Winter Park Chain of Lakes offers paddleboarding, kayaking, boating, and even scenic boat tours that pass by historic mansions and charming boathouses.

    Great Schools & Strong Sense of Community

    Families are drawn to Winter Park for more than just its beauty—it’s also home to some of Orange County’s highest-rated schools. The area features a mix of well-regarded public, private, and charter school options, giving families flexibility and peace of mind.

    Community involvement is high, and you’ll often find neighbors out walking their dogs, attending art festivals, or volunteering with local organizations. It’s the kind of place where people wave hello and remember your name—something that’s getting harder to find these days.

    A Place That Just Feels Like Home

    With its perfect blend of small-town warmth, cultural richness, and high-quality living, Winter Park continues to attract buyers from across the region and beyond. Whether you’re moving across town or across the country, Winter Park offers a lifestyle that’s both aspirational and accessible.

    If you’re looking for a neighborhood that offers a sense of place, a strong community spirit, and long-term value—Winter Park might just be the perfect fit.

    Image via Flickr

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