Winter Park
Winter Park is a charming city located in central Florida, just north of Orlando. The city is known for its tree-lined streets, beautiful parks, and historic architecture, as well as its vibrant arts and cultural scene. One of the most prominent features of Winter Park is its picturesque downtown area, which is filled with unique shops, galleries, and restaurants. The downtown area is also home to a number of museums, including the Morse Museum of American Art, which houses the world’s largest collection of works by Louis Comfort Tiffany. Winter Park is also known for its beautiful parks, which offer a variety of recreational activities, including boating, fishing, and hiking. One of the most popular parks in the city is Central Park, which features a beautiful rose garden, a fountain, and a stage that hosts live music performances and events throughout the year. In addition to its natural beauty and cultural attractions, Winter Park is home to a thriving business community, with a mix of small, locally-owned shops and larger, national retailers. The city is also home to several prestigious colleges and universities, including Rollins College, a top-ranked liberal arts college. Winter Park, Florida offers a variety of home communities, ranging from historic neighborhoods to modern developments. Here are some of the popular home communities in Winter Park:- Windsong: A luxurious, gated community with custom-built homes, surrounded by nature preserves and waterways. The community features a private lake, clubhouse, and pool, as well as walking and biking trails.
- The Vias: An established neighborhood located in the heart of Winter Park, featuring beautiful homes with mature landscaping, oak trees, and brick streets. The Vias is known for its family-friendly atmosphere and easy access to Winter Park’s shopping and dining destinations.
- Lake Virginia: A prestigious neighborhood with a mix of historic and modern homes, many of which have waterfront views. The neighborhood is located near Rollins College and features a variety of outdoor recreational opportunities, including boating, fishing, and kayaking.
- Winter Park Village: A mixed-use development featuring luxury condos, townhomes, and apartments, as well as shops, restaurants, and a movie theater. The community offers a convenient location and a walkable lifestyle, with easy access to nearby parks and amenities.
- The Oaks of Maitland: A gated community located just outside of Winter Park, featuring custom-built homes on large lots. The community offers a tranquil setting with mature trees, a community pool, and tennis courts.
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Listing No.
O6387500
Listing No.
O6380444
Listing No.
O6387200
Listing No.
O6411706
Listing No.
O6416342
Listing No.
O6407606
Listing No.
O6414890
Listing No.
O6432219
Listing No.
O6422951
Open House:
Aug 29, 2026, 12:00 PM - 2:00 PM
Listing No.
O6399395
Open House:
Aug 30, 2026, 12:00 PM - 2:00 PM
Listing No.
O6428952
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$574,900
3 3 Beds
2 2 Baths
1,269 SqFt 1,269 SqFt
O6387500 Listing No. O6387500
House Property Type: House
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(39)
(17)
$7,250,000
5 5 Beds
5 | 1 5 | 1 Baths
5,905 SqFt 5,905 SqFt
O6380444 Listing No. O6380444
House Property Type: House
(17)
(58)
$6,900,000
6 6 Beds
5 | 2 5 | 2 Baths
6,396 SqFt 6,396 SqFt
O6387200 Listing No. O6387200
House Property Type: House
(58)
VIRTUAL TOUR
(75)
$6,000,000
5 5 Beds
6 | 2 6 | 2 Baths
7,397 SqFt 7,397 SqFt
O6411706 Listing No. O6411706
House Property Type: House
VIRTUAL TOUR
(75)
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$5,600,000
5 5 Beds
5 | 1 5 | 1 Baths
5,152 SqFt 5,152 SqFt
O6416342 Listing No. O6416342
House Property Type: House
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(72)
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(10)
$5,500,000
4 4 Beds
4 | 1 4 | 1 Baths
4,775 SqFt 4,775 SqFt
O6407606 Listing No. O6407606
House Property Type: House
VIRTUAL TOUR
(10)
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$4,950,000
4 4 Beds
5 | 2 5 | 2 Baths
5,550 SqFt 5,550 SqFt
O6414890 Listing No. O6414890
House Property Type: House
VIRTUAL TOUR
(67)
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(11)
$4,650,000
5 5 Beds
5 | 1 5 | 1 Baths
4,827 SqFt 4,827 SqFt
O6432219 Listing No. O6432219
House Property Type: House
VIRTUAL TOUR
(11)
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(56)
$4,595,000
5 5 Beds
5 | 1 5 | 1 Baths
5,211 SqFt 5,211 SqFt
O6422951 Listing No. O6422951
House Property Type: House
VIRTUAL TOUR
(56)
Open House: Aug 29, 2026, 12:00 PM - 2:00 PM
VIRTUAL TOUR
(85)
$3,995,000
4 4 Beds
5 | 1 5 | 1 Baths
4,066 SqFt 4,066 SqFt
O6399395 Listing No. O6399395
House Property Type: House
VIRTUAL TOUR
(85)
Open House: Aug 30, 2026, 12:00 PM - 2:00 PM
VIRTUAL TOUR
(71)
$3,895,000
3 3 Beds
3 | 2 3 | 2 Baths
3,878 SqFt 3,878 SqFt
O6428952 Listing No. O6428952
Condo Property Type: Condo
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$3,890,000
6 6 Beds
5 5 Baths
4,677 SqFt 4,677 SqFt
O6432790 Listing No. O6432790
House Property Type: House
VIRTUAL TOUR
(11)
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