Winter Park

Winter Park is one of Central Florida's oldest and eclectic cities boasting a population of approximately 27,852 (2010 U.S. Census). The city was founded as a resort community by northern business magnates in the late 19th and early 20th Centuries. Winter Park is most well known for it's main street (Park Ave.) which includes civic buildings, art galleries, retail shops, museums, a park, train station, country club, historic cemetery, and a world renowned Private College in Rollins College.

Real Estate Statistics

Total Listings: 454
Average Price: $767,940
Highest Price: $6,900,000
Lowest Price: $0

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Winter Park

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
454 Properties Found. Page 1 of 38

This House Is A Must See And Will Not Be On The...

NEW Photo of Listing #O5540100

$265,000 Active

  • 3 Beds
  • 2 Baths
  • 0.21 Acres
  • 1,647 ft²

Residential

3650 Jonquil Ln, Winter Park, FL

MLS® #O5540100

This House Is A Must See And Will Not Be On The Market Long! As You Enter This Spacious Home Your Eye Will Be Drawn To The Fireplace At The Back Of The Home And To The Cathedral Ceilings To Your Left. As You Enter The Kitchen You Will Appreciate The Stunnin...

Look No Further! Immaculate Spacious Home In V...

NEW Photo of Listing #O5538940

$649,900 Active

  • 4 Beds
  • 3 Baths
  • 0.29 Acres
  • 2,274 ft²

Residential

837 Brock St, Winter Park, FL

MLS® #O5538940

Look No Further! Immaculate Spacious Home In Very Well Sought After Park Grove Neighborhood In Winter Park. Tile, Wood And Carpet Throughout, Gas Appliances, Over-sized Refrigerator, Wood Burning Fireplace, Screened In Back Porch. Master Bedroom Bath Comp...

You Won't Want To Miss This Great 4 Bedroom 2 B...

NEW Photo of Listing #O5540811

$224,900 Active

  • 4 Beds
  • 2 Baths
  • 0.3 Acres
  • 1,349 ft²

Residential

827 Densmore Dr, Winter Park, FL

MLS® #O5540811

You Won't Want To Miss This Great 4 Bedroom 2 Bathroom Pool Home Home In The Winter Park Estates Community! This Is A Great Home In A Great Neighborhood With Great Bones! The Interior Features Include An Open Kitchen And Dining Area And Interior Utility Con...

A Charming Ranch-style House In The Quiet Eastb...

NEW Photo of Listing #T2908266

$399,000 Active

  • 4 Beds
  • 2 Baths
  • 0.35 Acres
  • 1,768 ft²

Residential

2436 Beman Ct, Winter Park, FL

MLS® #T2908266

A Charming Ranch-style House In The Quiet Eastbrook Subdivision Of Winter Park, This 4/2 Home With Tiled Floors Has A Backyard Swimming Pool, New Storm Windows, A New Air-conditioning Unit, And A Brand New Sandstone Paver Driveway. There Is Also Plenty Of B...

Welcome Home To This Gorgeous Corner-unit Luxur...

NEW Photo of Listing #O5540462

$1,099,000 Active

  • 3 Beds
  • 2 Baths
  • 0.63 Acres
  • 2,100 ft²

Residential

315 E New England Ave #20, Winter Park, FL

MLS® #O5540462

Welcome Home To This Gorgeous Corner-unit Luxury Condo Located Just Blocks From Park Avenue. This 3-bedroom, 2-bath Unit Is Located At Villa Siena, The ”jewel Of Winter Park” And Has Been Upgraded With The Finest Finishes. The Very Fashionable And Chic Park...

Must See This Diamond In The Rough. Block Home ...

NEW Photo of Listing #O5541907

$299,000 Active

  • 3 Beds
  • 2 Baths
  • 0.26 Acres
  • 1,848 ft²

Residential

5044 Lake Howell Rd, Winter Park, FL

MLS® #O5541907

Must See This Diamond In The Rough. Block Home With Many Options And Tremendous Upside In Beautiful Winter Park. Home Currently Has Two Attached In-law Suites With Private Entrances. Each Boasts Living Room, Kitchen, One Bedroom And One Bathroom. Units Are ...

Must See Video And Photography Of This Stunning...

NEW Photo of Listing #O5541750

$2,250,000 Active

  • 4 Beds
  • 6 Baths
  • 0.56 Acres
  • 5,194 ft²

Residential

531 Lake Front Blvd, Winter Park, FL

MLS® #O5541750

Must See Video And Photography Of This Stunning Villa Paradise Home!!! Luxury Lifestyle Living With The Best Commute And Most Convenient Location In Central Florida/old Winter Park. This Custom Built Home Is Truly Workman's Quality From Grand-entry To Doork...

Adorable Bungalow Located In Winter Park Which ...

NEW Photo of Listing #O5542033

$215,000 Active

  • 3 Beds
  • 2 Baths
  • 0.2 Acres
  • 975 ft²

Residential

835 Driver Ave, Winter Park, FL

MLS® #O5542033

Adorable Bungalow Located In Winter Park Which Is About 5 Mins To Dubsdread Golf Course And The Historic Tap Room Which Offers Culinary Excellence. This 3 Bedroom 1.5 Bathroom Has Adequate Closets And The 3rd Bedroom Is Currently Being Used As A Art Studio...

Hidden, Quiet Garden Oasis With Amazing Pool An...

NEW Photo of Listing #O5542006

$1,235,000 Active

  • 4 Beds
  • 5 Baths
  • 0.41 Acres
  • 3,250 ft²

Residential

2402.5 Temple Dr, Winter Park, FL

MLS® #O5542006

Hidden, Quiet Garden Oasis With Amazing Pool And Outdoor Areas In Sought After Winter Park Neighborhood. Non Visible From The Street, A 150' Concrete Driveway Leads To An Electric Gate, Assuring Complete Privacy. Motor Court With 3-car Garage And Extra Park...

Complete Re-do On This 3 Bedroom, 2 Bath Locate...

NEW Photo of Listing #O5542467

$194,500 Active

  • 3 Beds
  • 2 Baths
  • 0.22 Acres
  • 1,541 ft²

Residential

5150 Goldenrod Place Rd, Winter Park, FL

MLS® #O5542467

Complete Re-do On This 3 Bedroom, 2 Bath Located In A+ Rated Seminole County. Come See For Yourself The Potential This Home Has To Make It Your Own. Buyer(s) Responsible For Verifying All Information Contained In This Listing.

Living In Winter Park 

Winter Park is one of Central Florida's oldest and eclectic cities boasting a population of approximately 27,852 (2010 U.S. Census). The city was founded as a resort community by northern business magnates in the late 19th and early 20th Centuries. Winter Park is most well known for it's main street (Park Ave.) which includes civic buildings, art galleries, retail shops, museums, a park, train station, country club, historic cemetery, and a world renowned Private College in Rollins College. 

Winter Park Village Century 21 Alton Clark

Top 5 Reasons to Buy Winter Park Real Estate

  1. Family friendly community with cobblestone streets
  2. Unique characteristics/architectural to every home old and new
  3. Live in a city that cherishes arts and culture
  4. World renowned Rollins College supports community
  5. Award winning dining & night life on the famous Park Ave.

Amenities Near Winter Park Homes For Sale

If there is one thing Winter Park is not in short supply of and that is amenities.

The city of Winter Park some of the highest ranking restaurants in all of FL. It’s museums are rich with historic treasures and findings usually from Winter Park and the surrounding Central FL area.

The community is very proactive and lively when it comes to it’s public entertainment. Nearly every weekend Winter Park’s most famous road, Park Avenue gets visited by a couple thousand locals and tourist. During these weekends, there are a vast number of activities ranging from yoga in the park to art festivals to movie in the park after dark, and the list goes forever. One thing is for certain and that this community is wholesome.Winter Park Golf Course Century 21 Alton Clark

One of the newest addition to Winter Park is the SunRail, Central Florida’s newest means of public transportation. The SunRail station runs through and stops in the heart of Winter Park right along Park Avenue. During high population festivals and activities at Winter Park, vehicle parking becomes scarce and time consuming. The SunRail has been an amazing feature not only alleviating traffic but to bring adventure to local and tourist means of travel.  

Winter Park golf course is small but very prestigious. Encompassed by astounding curb appeal real estate and brick roads, majority of Winter Park Golf Course members are neighbors and locals of Winter Park. But don’t worry, it’s not exclusive to locals only.  

History Of Winter Park

The city was originally named Lakeview in 1858 and re-named Osceola in 1870. Eleven years later, the name Winter Park was chosen by its founders. Loring Chase and Oliver Chapman, who during an informal discussion, decided they wanted the name to be something about a park in winter. Thus the name Winter Park.


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Listing data comes from My Florida Regional MLS.

Listing information last updated on October 19th, 2017 at 11:48pm CDT.