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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
Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined...
- 5 Beds
- 5 Baths
- O6437159 MLS
Virtually Staged. Brand new Roof and HVAC systems in 2025 and all new windows 2026. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park t...
- 4 Beds
- 5 Baths
- TB8545586 MLS
Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in ...
- 4 Beds
- 3 Baths
- O6433534 MLS
Prime Investment Opportunity on Aloma Avenue! Fully occupied strip plaza featuring five established tenants, offering immediate rental income and strong investment potent...
- O6439170 MLS
Welcome to luxury living in Hawks Crest, Winter Park’s only guard-gated community. This exceptional six-bedroom Del Rio floor plan sits on one of the neighborhood’s most ...
- 6 Beds
- 5 Baths
- O6440381 MLS
Virtually Staged. Zoned for Fantastic Winter Park Schools, this 4 bed, 2 bath recently renovated abode is waiting for you. Located on a quiet, tree-lined street, you can ...
- 4 Beds
- 2 Baths
- O6437438 MLS
Welcome home to Winter Park! This beautifully renovated 3-bedroom, 1.5-bath home offers the perfect combination of classic Florida living and extensive modern updates. Mu...
- 3 Beds
- 2 Baths
- O6440392 MLS
Brand new 2026 custom residence in the heart of downtown Winter Park, just completed and showcasing elevated finishes thoughtfully curated by FG Schaub Construction & SOC...
- 5 Beds
- 6 Baths
- O6439388 MLS
Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS. Set on a prominent corner lot within exclusive Via Tuscany, this extraordina...
- 4 Beds
- 5 Baths
- O6439181 MLS
This is exactly what you are looking for! Adorable 2/2 close to Full Sail and UCF. Tons of shopping and restaurants and convenient to the 417 and the 408. Location makes ...
- 2 Beds
- 2 Baths
- O6439897 MLS
- C Bldg.
Prime Winter Park commercial office building with visibility of monument signage from 1-4 East bound traffic and Ideally situated on Wymore Road. This 2018 built one stor...
- O6440396 MLS
Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury c...
- 3 Beds
- 4 Baths
- O6438596 MLS
- Versailles Of Winter Park Bldg.
Bright, airy, and designed for a resort living! Welcome to a turn-key Winter Park Pine home where everyday life feels like a getaway! From the moment you enter, you will ...
- 3 Beds
- 2 Baths
- O6440062 MLS
Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready i...
- 2 Beds
- 2 Baths
- O6439854 MLS
- F Bldg.
Mid-century style meets modern convenience in this beautifully updated Winter Park home, offering a move in opportunity with no HOA. Extensively improved since 2022, the ...
- 3 Beds
- 1 Baths
- O6439689 MLS
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