College Park / Winter Park

This rich era saw incredible growth in neighborhoods and landmark establishments.

Welcome to College Park/Winter Park

Tropical beauty and a strong sense of history minutes from Downtown. Explore Winter & College Park Orlando real estate!
Perfectly placed near Downtown Orlando, Winter Park and College Park real estate offer the best of city living with the wild beauty for which Florida is known. The welcoming Old Florida ambiance and endless sunshine may capture your heart first, but Winter Park has plenty of standout amenities. With elegant museums and an artistic sensibility, this town began as a winter getaway and has developed into an easy-going suburban community. Coastal style informs the airy homes with stunning classic designs, wrap-around porches, pastel colors, and opulent new construction builds. 

Once the shady, serene home to citrus groves, College Park developed with the real estate boom of the early 1900s. This rich era saw incredible growth in neighborhoods and landmark establishments, like the Dubsdread Golf Course, and by the mid-20th century, the area flourished with lovely homes and lush landscaping. This dreamy place inspired famed beat writer Jack Kerouac, who lived and wrote here, and astronaut John Young. Today, this community is one of Orlando’s most distinctive, with affluent style and sophisticated luxury. Known for iconic bungalow homes and mid-century architecture, College Park offers vibrant city living with a decidedly quaint charm.

What to Love About College & Winter Park Orlando Real Estate 

  • Strong local history and stunning architecture
  • Close to vibrant Downtown Orlando
  • Outstanding cuisine and trendy bistros
  • Stylish boutiques and an artistic atmosphere

People & Lifestyle

Well-rounded College Park offers an ideal backdrop for young professionals working in Orlando’s corporate center but is just as attractive to families and retirees craving the quiet of a residential oasis and close access to a thriving urban life. Winter Park’s stunning natural beauty sets the stage for an active lifestyle, and residents can often be found boating along the picturesque chain of lakes. 

Dining, Entertainment & Shopping

With a retro vibe and homestyle cooking made to order, Christo's Cafe welcomes guests with warm Southern hospitality and a menu of delicious diner classics, while laid-back Shakers American Cafe serves Orlando’s best breakfast, and PR's Taco Palace is a local mainstay for a casual good time and dynamite tacos. Set on the picturesque, historic Dubsdread Golf Course, the Tap Room at Dubsdread dazzles with award-winning cuisine. Winner of countless Best Of awards, this College Park hidden gem is the haunt of everyone from politicians and celebrities to professional athletes and residents. 

In Winter Park, chic bistro Prato marries Italian classics with seasonal ingredients and a modern approach, while Briarpatch Restaurant offers vibrant seasonal flavors, artisan pastries, and an elevated brunch menu. Embracing the airy elegance and bright beauty of the Mediterranean, Ava MediterrAegean is known for its stunning dining room, artfully designed dishes, and private luxury membership club. With a strong farm-to-table focus, Boca features a seasonal menu featuring the freshest available ingredients, inspiring new creative menus each week. Although life in College Park and Winter Park feels like a holiday, sometimes keeping track of time is a necessity – and the timeless pieces at Orlando Watch Company allow you to track your minutes in style. 

Things to Do

Stroll through the rose garden at Central Park or host a private event on the stunning tree-canopied grounds. In College Park, Dartmouth Park offers gorgeous lawns and majestic trees perfect for a family picnic. Nearby, Ace Cafe sets the stage for excitement with a lively atmosphere of music and motorcycles. Stop in for the decadent gastro-diner fare or enjoy a classic car show and monthly bike meet. Art lovers will be delighted to attend the Winter Park Sidewalk Art Festival. Florida’s most prestigious open-air art show, this elegant affair showcases nationally recognized artists and jazz musicians. Don't miss the Scenic Winter Park Boat Tour that takes you on a journey through the history of the area and the residents that helped develop Winter Park and Orlando. 

Nearby Downtown Orlando is a thriving destination for nightlife and celebration, hosting over 1,200 events annually. From concerts and theater to professional sports and outdoor festivals, this is the area’s most dynamic spot for world-class entertainment. Mark your calendar for the College Park JazzFest, the neighborhood’s beloved celebration of jazz. Featuring three stages and a fleet of gourmet food trucks, this vibrant event will have you dancing in the streets. The sunny weather and abundant nature trails in College Park were made for biking, and Orange Cycle is central Florida’s premier place to get ready for a biking adventure. 


Residents of College Park and Winter Park have access to some of Orlando’s best public and private schools, including:



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