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Winter Park Real Estate Search

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Winter Park Homes for Sale

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Winter Park is a city located in Orange County, Florida, a city of about 25,000 residents. Famous for its stately trees, brick lined roads, spectacular homes, museums, shops along Park Avenue and it breathtaking parks.

Chartered in 1887 the city was originally used as a winter resort for the wealthy Northerners seeking refuge from the cold winters and looking for a warm tranquil place to relax, its main attractions to tourist were its lakes, warm temperatures and natural habitat.

Rollins College the oldest college on Florida and the nations premiere Liberal Arts College was founded ion Winter Haven in 1885 by New England Congregationalists who sought to bring their style to Florida liberal arts education. Rollins has been praised by magazines such as Time and U.S. New and World report has named it one of "America's Best Colleges".

With several lakes adjoining each other and home to Orlando´s many Lake Front Homes, Winter Park is now considered one of the most sought after residential areas a few minutes drive North of Downtown Orlando. Private Schools, Boutique Shops, Luxury Condos, Fine Dining Restaurants, Law Firms and Private Health Clinics are commonly associated with Winter Park.

Latest Winter Park Listings

2107 Edwin Boulevard, Winter Park image
2107 Edwin Boulevard, Winter Park $450,000

Welcome home to this beautiful 4 bedroom, 2 bathroom home located in the center of Winter Park. This home was fully renovated in 2016 and has a variety of features inclu...

  • 4 Beds
  • 2 Baths
  • Eastgate Sub SubDv.
  • 32792 Zip Code
2818 Fitzooth Drive, Winter Park image
2818 Fitzooth Drive, Winter Park $639,000

Take a look at this stunning remodeled abode on a quiet, tree lined street in the Winter Park Pines offering 3 beds, 2 baths, plus office, sparkling and heated pool and s...

  • 3 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
2008 Natalen Road, Winter Park image
2008 Natalen Road, Winter Park $599,999

One or more photo(s) has been virtually staged. One or more photos are virtually staged. Beautifully renovated! This Winter Park family house is located on a quiet, priva...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 07 SubDv.
  • 32792 Zip Code
1936 Whitehall Drive, Winter Park image
1936 Whitehall Drive, Winter Park $519,900

This adorable and meticulously maintained home is beautifully situated in the heart of Winter Park. Step inside the front door, you won't be disappointed. Large Living...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores SubDv.
  • 32792 Zip Code
1790 Hollywood Avenue, Winter Park image
1790 Hollywood Avenue, Winter Park $698,500

Renovated Bungalow in the Heart of Winter Park. Only minutes drive to Park Ave. This charming 2 bed 2 bath home boast hardwood floors throughout, custom cabinetry with ...

  • 2 Beds
  • 2 Baths
  • Lake Monte Sub SubDv.
  • 32789 Zip Code
2250 Venetian Way, Winter Park image
2250 Venetian Way, Winter Park $1,200,000

Great opportunity to build in Winter Park with easy access to the Winter Park Chain of Lakes. This 80x150 lot on the Venetian Canal features quick access to Lake Maitla...

  • 3 Beds
  • 2 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
580 Ololu Drive, Winter Park image
580 Ololu Drive, Winter Park $1,495,000

Luxury Lifestyle on Beautiful Lake Killarney. Enjoy the serenity of lakeside living on the largest and cleanest private lake in Winter Park. Lake Killarney is the hidden ...

  • 3 Beds
  • 2.5 Baths
  • Killarney Circle SubDv.
  • 32789 Zip Code
2955 Sanbina Street, Winter Park image
2955 Sanbina Street, Winter Park $550,000

Newly updated home perfect for all-year round entertaining. The home has been tastefully updated throughout. 3 bedroom 2 bath ranch style split floor plan home with bon...

  • 3 Beds
  • 2 Baths
  • Howell Heights SubDv.
  • 32789 Zip Code
453 Warrenton Road Unit 453, Winter Park image
453 Warrenton Road Unit 453, Winter Park — Winter Park Pines Condo $279,900 ▼

Dreams Do Come True! Spectacular Highly Desirable Winter Park Pines 2 bedroom 2 bath single story Villa Style condo. Located on a picturesque tree lined street, like if s...

  • 2 Beds
  • 2 Baths
  • Winter Park Pines Condo SubDv.
  • 32792 Zip Code
660 W Morse Boulevard, Winter Park image
660 W Morse Boulevard, Winter Park — Morse $2,500,000

Situated within walking distance to Hannibal Square and Park Avenue, the premiere shopping and fine dining hubs of Winter Park, sits this luxurious Phil Kean designed ho...

  • 3 Beds
  • 3.5 Baths
  • Morse & Pennsylvania Twnhms SubDv.
  • 32789 Zip Code

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