Orange County

Winter Park

About Winter Park

Winter Park has a population of nearly 28,000 residents and was founded as a resort community in the early 20th century. Winter Park is known for the vibrant main street full of art galleries, museums, civic buildings, shopping & much more.

Winter Park Homes for Sale
Total Listings 657
Average Price $806,032
Highest Price $7,895,000
Lowest Price $64,999

Winter Park Florida

Homes in Winter Park

Winter Park FountainThe properties found in Winter Park include some townhomes and condominiums. However, most are single-family homes and tend to be larger with four or more bedrooms. Many homes have been custom built with luxurious amenities. There are a number of large estates located on the water in Winter Park.

The average home hitting the market in Winter Park will be listed for about $866K. However, the price range can easily get up into the millions for some of the larger estates.

Attractions and Things to Do in Winter Park

Alfond Inn in Winter Park FloridaWith plenty of history surrounding the Langford Resort Hotel, Winter Park has been a popular destination for many years. While this specific hotel is no longer in existence, it once attracted guest, such as Ray Charles, John Denver, Dean Martin and even President Ronald Reagan. The Alfond Inn now occupies the space where the Langford used to sit.

Today, many are most attracted to the area for Park Avenue, which provides the majority of the amenities in Winter Park. Plenty of fine dining, boutique shopping and entertainment are found on Park Avenue. Some of the top spots include 310 Park South, Luma on Park and Prato.

Winter Park Chain of LakesAlong with the dining and shopping on Park Avenue, the city is home to a country club, historic cemetery, train station, plenty of art galleries and a beach and boat launch. Some of the most popular sites of interest in the city include:

  • Annie Russel Theatre
  • Edward Hill Brewer House
  • Cornell Fine Arts Museum
  • Hannibal Square
  • Mead Botanical Garden
  • Kraft Azalea Park
  • Winter Park Public Library
  • Winter Park Historical Museum
  • And More!

Annie Russel Theatre at Rollins College in Winter ParkThe scenic Winter Park boat tours provide a great way to see some of the beautiful homes found throughout the community. Along with the many sites of interest, Winter Park is home to the Winter Park Sidewalk Art Festival, which is the largest and the oldest of the art festivals found in the country.

Education and Schools in Winter Park

There are plenty of great schools found throughout Winter Park, Florida. From public elementary schools to well-known colleges, the area is well-known for the schools. Some of the top schools found in Winter Park include:

  • Aloma Elementary School
  • The Geneva School
  • The Parke House AcademyFull Sail University in Winter Park
  • Lakemont Elementary School
  • St. Margaret Mary Catholic School
  • Trinity Preparatory School
  • Winter Park High School
  • Full Sail University
  • Rollins College
  • Valencia Community College
  • Crealde School of Art

Living in Winter Park

Many move to Winter Park due to the bustling Park Avenue area and the beautiful homes. It's a desirable area, which started as a resort community. Of course, the close proximity to Orlando helps to attract new home buyers relocating to the area, as well.

Winter Park Homes for Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
657 Properties Found. Page 1 of 14.
Photo of Listing #O5736189
New Listing

N/A, Winter Park

$100,000 - 3 Beds, 2 Baths, 1,284 Sf

MLS® # O5736189

Photo of Listing #O5754782
New Listing

7449 Restful St, Winter Park

$200,000 - 1 Acres

MLS® # O5754782

Photo of Listing #O5771105
New Listing

N/A, Winter Park

$349,000 - 3 Beds, 3 Baths, 1,655 Sf

MLS® # O5771105

Photo of Listing #O5769711
New Listing

1304 Formosa Ave, Winter Park

$249,500 - 2 Beds, 1 Baths, 1,122 Sf

MLS® # O5769711

Photo of Listing #O5766030
New Listing

1161 Valencia Ave, Winter Park

$699,900 - 4 Beds, 2 Baths, 2,032 Sf

MLS® # O5766030

Photo of Listing #O5766099
New Listing

1161 Valencia Ave, Winter Park

$699,900

MLS® # O5766099

Photo of Listing #O5767327
New Listing

2920 Bromley Rd, Winter Park

$394,900 - 4 Beds, 2 Baths, 2,296 Sf

MLS® # O5767327

Photo of Listing #O5767879
New Listing

1440 Auburn Green Loop, Winter Park

$225,000 - 2 Beds, 2 Baths, 1,126 Sf

MLS® # O5767879

Photo of Listing #O5762843
New Listing

640 N Park Ave #7, Winter Park

$339,000 - 2 Beds, 2 Baths, 858 Sf

MLS® # O5762843

Photo of Listing #O5771894
New Listing

1460 Mayfield Ave, Winter Park

$865,000 - 3 Beds, 3 Baths, 2,400 Sf

MLS® # O5771894

Photo of Listing #O5771954
New Listing

2217 Howard Dr, Winter Park

$695,000 - 3 Beds, 2 Baths, 2,387 Sf

MLS® # O5771954

Photo of Listing #O5771953
New Listing

1680 Dale Ave, Winter Park

$500,000

MLS® # O5771953

Photo of Listing #O5771773
New Listing

601 Berwick Dr #2, Winter Park

$485,000 - 5 Beds, 3 Baths, 2,384 Sf

MLS® # O5771773

Photo of Listing #O5770681
New Listing

2351 Westminster Ct, Winter Park

$379,900 - 3 Beds, 2 Baths, 1,568 Sf

MLS® # O5770681

Photo of Listing #O5763176
New Listing

825 Driver Ave, Winter Park

$217,000 - 2 Beds, 2 Baths, 1,115 Sf

MLS® # O5763176

Photo of Listing #O5763457
New Listing

609 Langholm Dr, Winter Park

$399,900 - 3 Beds, 2 Baths, 1,946 Sf

MLS® # O5763457

Photo of Listing #O5766384
New Listing

2816 Salisbury Blvd, Winter Park

$237,500 - 3 Beds, 2 Baths, 1,762 Sf

MLS® # O5766384

Photo of Listing #O5767840
New Listing

1570 Grove Ter, Winter Park

$515,000 - 3 Beds, 2 Baths, 1,663 Sf

MLS® # O5767840

Photo of Listing #O5768043
New Listing

5452 Bracken Ct, Winter Park

$184,900 - 3 Beds, 2 Baths, 1,178 Sf

MLS® # O5768043

Photo of Listing #A4430308
New Listing

3102 Shady Pine Ave #2, Winter Park

$307,000 - 4 Beds, 2 Baths, 1,609 Sf

MLS® # A4430308

Photo of Listing #O5771576
New Listing

1096 Wading Waters Cir, Winter Park

$550,579 - 4 Beds, 3 Baths, 2,702 Sf

MLS® # O5771576

Photo of Listing #O5771153
New Listing

2138 Lake Dr, Winter Park

$2,200,000 - 5 Beds, 5 Baths, 5,398 Sf

MLS® # O5771153

Photo of Listing #O5771667
New Listing

1555 Woodland Ave, Winter Park

$795,000 - 4 Beds, 4 Baths, 3,264 Sf

MLS® # O5771667

Photo of Listing #O5771577
New Listing

2721 Ambergate Rd, Winter Park

$249,900 - 3 Beds, 2 Baths, 1,210 Sf

MLS® # O5771577

Photo of Listing #O5771488
New Listing

100 S Interlachen Ave #106, Winter Park

$429,000 - 2 Beds, 2 Baths, 1,109 Sf

MLS® # O5771488

Photo of Listing #O5770776
New Listing

471 Sylvan Dr, Winter Park

$1,899,000 - 5 Beds, 6 Baths, 6,430 Sf

MLS® # O5770776

Photo of Listing #O5769945
New Listing

2572 Fifeshire Dr, Winter Park

$500,000 - 4 Beds, 3 Baths, 2,578 Sf

MLS® # O5769945

Photo of Listing #O5754518
New Listing

1576 Lawndale Cir, Winter Park

$239,000 - 3 Beds, 2 Baths, 1,271 Sf

MLS® # O5754518

Photo of Listing #O5756372
New Listing

1861 Harland Park Dr, Winter Park

$875,000 - 4 Beds, 4 Baths, 3,052 Sf

MLS® # O5756372

Photo of Listing #O5760134
New Listing

2944 Bower Rd, Winter Park

$365,000 - 4 Beds, 3 Baths, 2,301 Sf

MLS® # O5760134

Photo of Listing #O5764821
New Listing

910 Hedgewood Ct, Winter Park

$259,000 - 3 Beds, 3 Baths, 1,578 Sf

MLS® # O5764821

Photo of Listing #O5765817
New Listing

5108 Oak Hill Dr, Winter Park

$199,000 - 3 Beds, 2 Baths, 1,020 Sf

MLS® # O5765817

Photo of Listing #O5766342
New Listing

2342 Smiley Ave, Winter Park

$285,000 - 4 Beds, 2 Baths, 1,630 Sf

MLS® # O5766342

Photo of Listing #O5766409
New Listing

2824 Cady Way, Winter Park

$300,000 - 3 Beds, 2 Baths, 1,392 Sf

MLS® # O5766409

Photo of Listing #O5767740
New Listing

690 Osceola Ave #207, Winter Park

$390,000 - 1 Beds, 2 Baths, 850 Sf

MLS® # O5767740

Photo of Listing #O5768565
New Listing

2917 Antique Oaks Cir #22, Winter Park

$130,000 - 2 Beds, 2 Baths, 1,018 Sf

MLS® # O5768565

Photo of Listing #O5768823
New Listing

2445 Sherbrooke Rd #2, Winter Park

$360,000 - 5 Beds, 2 Baths, 2,163 Sf

MLS® # O5768823

Photo of Listing #O5771235
New Listing

367 Saint Dunstan Way, Winter Park

$369,900 - 3 Beds, 2 Baths, 1,752 Sf

MLS® # O5771235

Photo of Listing #O5771257
New Listing

633 Trinidad Ct #633, Winter Park

$124,900 - 2 Beds, 2 Baths, 1,120 Sf

MLS® # O5771257

Photo of Listing #O5770364
New Listing

230 E Rockwood Way, Winter Park

$1,299,000 - 4 Beds, 4 Baths, 3,374 Sf

MLS® # O5770364

Photo of Listing #O5770400
New Listing

2419 Beman Ct, Winter Park

$264,900 - 3 Beds, 2 Baths, 1,413 Sf

MLS® # O5770400

Photo of Listing #O5771760
New Listing

2341 Mulbry Dr, Winter Park

$299,000 - 3 Beds, 1 Baths, 1,165 Sf

MLS® # O5771760

Photo of Listing #O5759356
New Listing

201 Chelton Cir, Winter Park

$995,000 - 4 Beds, 4 Baths, 3,560 Sf

MLS® # O5759356

Photo of Listing #O5761902
New Listing

5528 Albert Dr, Winter Park

$239,900 - 4 Beds, 2 Baths, 1,500 Sf

MLS® # O5761902

Photo of Listing #O5766441
New Listing

1500 Gay Rd #24-b, Winter Park

$175,000 - 2 Beds, 2 Baths, 1,026 Sf

MLS® # O5766441

Photo of Listing #O5766326
New Listing

2334 Brookshire Ave, Winter Park

$589,000 - 4 Beds, 4 Baths, 2,679 Sf

MLS® # O5766326

Photo of Listing #O5770378
New Listing

1790 Oakhurst Ave, Winter Park

$335,000 - 3 Beds, 2 Baths, 1,136 Sf

MLS® # O5770378

Photo of Listing #O5761673
New Listing

1500 Gay Rd #26-b, Winter Park

$179,900 - 2 Beds, 2 Baths, 1,026 Sf

MLS® # O5761673

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on March 23rd, 2019 at 8:00pm CDT.

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