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Discover the refined charm of Winter Park, FL, a picturesque city just north of Orlando where oak-lined streets, scenic lakes, and elegant architecture create an atmosphere of timeless beauty. Stroll across Park Avenue — Winter Park’s cultural and culinary heart — filled with boutique shops, sidewalk cafés, and lush Central Park hosting seasonal festivals. Immerse yourself in the arts at gems like the Charles Hosmer Morse Museum of American Art or the Rollins Museum of Art, tour historic Casa Feliz, or unwind in the green tranquility of Mead Botanical Garden or Kraft Azalea Park. Whether you love lakeside walks, weekend farmers’ markets, or exploring unique museums, there’s always something delightful here — and plenty of opportunity when you explore homes for sale Winter Park FL to call this sophisticated oasis home.

Homes for Sale in Winter Park

901 Enclave Place, Winter Park image
901 Enclave Place, Winter Park — 901 $1,495,000

Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, ...

  • 4 Beds
  • 4 Baths
  • O6383602 MLS
  • 901 Bldg.
905 Enclave Place, Winter Park image
905 Enclave Place, Winter Park — 905 $1,495,000

Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...

  • 4 Beds
  • 4 Baths
  • O6383679 MLS
  • 905 Bldg.
914 Enclave Place, Winter Park image
914 Enclave Place, Winter Park $1,895,000

Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, feat...

  • 5 Beds
  • 5 Baths
  • O6391825 MLS
7300 Daniel Webster Drive Unit M7, Winter Park image
7300 Daniel Webster Drive Unit M7, Winter Park $159,000 ▼

Welcome home to this stunningly updated two-story condo that perfectly combines modern elegance with everyday comfort. Featuring 2 spacious bedrooms and 2.5 baths, this h...

  • 2 Beds
  • 3 Baths
  • O6388668 MLS
3027 Aaron Burr Avenue Unit L1, Winter Park image
3027 Aaron Burr Avenue Unit L1, Winter Park — Na $159,000 ▼

Step into this beautifully renovated two-story condo offering the perfect blend of modern style and everyday comfort. Featuring 2 spacious bedrooms and 2.5 updated bathro...

  • 2 Beds
  • 3 Baths
  • O6390662 MLS
  • Na Bldg.
1903 N Park Avenue, Winter Park image
1903 N Park Avenue, Winter Park $1,695,000 ▼

Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park...

  • 4 Beds
  • 4 Baths
  • O6375766 MLS
1807 Hammerlin Avenue Unit G, Winter Park image
1807 Hammerlin Avenue Unit G, Winter Park — Terrazo Del Sol $499,000 ▼

Virtually Staged. **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local bouti...

  • 3 Beds
  • 3 Baths
  • O6391277 MLS
  • Terrazo Del Sol Bldg.
1800 Magnolia Avenue, Winter Park image
1800 Magnolia Avenue, Winter Park $994,000 ▼

Virtually Staged. JULY 2026 NEW CONCRETE CIRCULAR DRIVE AND NEW CONCRETE SIDEWALKS! PRICE IMPROVEMENT! NO HOA! SEPTIC INSPECTED AND CERTIFIED. Experience refined living i...

  • 4 Beds
  • 3 Baths
  • NS1087637 MLS
501 Heritage Boulevard, Winter Park image
501 Heritage Boulevard, Winter Park $449,900 ▼

Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, of...

  • 4 Beds
  • 2 Baths
  • S5145746 MLS
1870 Walker Avenue, Winter Park image
1870 Walker Avenue, Winter Park $1,199,000 ▼

This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys...

  • 3 Beds
  • 3 Baths
  • O6390504 MLS
Lot #21 Karolina Ave, Winter Park image
Lot #21 Karolina Ave, Winter Park $918,000 ▼

Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this ...

  • 4 Beds
  • 3 Baths
  • O6387812 MLS
1581 Forest Avenue, Winter Park image
1581 Forest Avenue, Winter Park $3,275,000 ▼

This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortles...

  • 4 Beds
  • 6 Baths
  • O6382377 MLS
Winter Park image
Winter Park $430,000 ▼

Updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has alre...

  • 4 Beds
  • 2 Baths
  • S5145631 MLS
1354 Indiana Avenue, Winter Park image
1354 Indiana Avenue, Winter Park $574,900 ▼

Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desi...

  • 3 Beds
  • 2 Baths
  • O6387500 MLS
2501 Winter Park Road, Winter Park image
2501 Winter Park Road, Winter Park $1,649,000 ▼

PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this ...

  • 5 Beds
  • 4 Baths
  • O6384756 MLS

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