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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. Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by one of the areas finest builders. This stunni...
- 4 Beds
- 4 Baths
- O6428019 MLS
Virtually Staged. Discover this spacious 3-bedroom, 2-bathroom home offers 1,483 sq ft of comfortable living space with a functional layout and plenty of room for everyda...
- 3 Beds
- 2 Baths
- C7528794 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath home in beautiful Winter Park! This move-in-ready property features stylish wood-look tile flooring throughout, crea...
- 3 Beds
- 2 Baths
- O6427582 MLS
Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinking right now. But hear me out, because this house ...
- 3 Beds
- 2 Baths
- O6427460 MLS
Medical Office Conversion Opportunity directly across from Advent Health Winter Park Hospital. Existing building offers potential for professional office conversion or ca...
- O6426997 MLS
Medical Office Conversion Opportunity directly across from Advent Health Winter Park Hospital. Existing building offers potential for professional office conversion or ca...
- O6426909 MLS
Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen b...
- 3 Beds
- 3 Baths
- O6426457 MLS
- 2033 Bldg.
Rare opportunity to own a charming Duplex on a corner lot in the heart of Winter Park! Located walking distance to Mead gardens and Orange Ave, and less than a mile from ...
- 2 Beds
- 2 Baths
- O6425358 MLS
Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers mar...
- 5 Beds
- 5 Baths
- O6424364 MLS
Welcome to Lake Spier Crossing with NO CDD and low HOA fees, an exclusive boutique lakefront community built by Winter Park's premier builder, Meridian Homes. Nestled bet...
- 3 Beds
- 4 Baths
- O6426102 MLS
- Lake Spier Bldg.
Virtually Staged. Conveniently located just minutes from I-4, downtown Orlando, and Winter Park, this versatile home offers the perfect blend of comfort, flexibility, and...
- 3 Beds
- 2 Baths
- W7887744 MLS
Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to pri...
- 3 Beds
- 3 Baths
- O6415977 MLS
Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to pri...
- 4 Beds
- 1 Baths
- O6415950 MLS
Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. T...
- 4 Beds
- 3 Baths
- O6425628 MLS
Great investment opportunity, tenant occupied/income producing Winter Park property in gated community.
- 3 Beds
- 3 Baths
- O6418710 MLS
- 2526 Bldg.
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