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: 467
Average Price: $804,789
Highest Price: $7,500,000
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
467 Properties Found. Page 1 of 39

Must See Video And Photography Of This Stunning...

NEW Photo of Listing #O5549567

$14,995 Active

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

Rental

531 Lake Front Blvd, Winter Park, FL

MLS® #O5549567

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...

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

NEW Photo of Listing #O5550649

$5,400 Active

  • 3 Beds
  • 2 Baths
  • 0.63 Acres
  • 1,955 ft²

Rental

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

MLS® #O5550649

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...

This 4 Ba / 2 Ba 1400 Sqft Home Features A Sing...

NEW Photo of Listing #O5550827

$1,250 Active

  • 2 Beds
  • 1 Baths
  • 0.12 Acres
  • 660 ft²

Rental

275 N Capen Ave, Winter Park, FL

MLS® #O5550827

This 4 Ba / 2 Ba 1400 Sqft Home Features A Single Car Garage With Washer/dryer, Two Full Baths, Separate Living And Dining Areas And A Sun Room! All Prospects Must Drive Past Property Before Any Showings Can Be Scheduled.

Updated Home, In Small Subdivision Of Lake Waun...

NEW Photo of Listing #O5550904

$350,000 Active

  • 3 Beds
  • 2 Baths
  • 0.36 Acres
  • 2,264 ft²

Residential

8010 Lake Waunatta Dr #2, Winter Park, FL

MLS® #O5550904

Updated Home, In Small Subdivision Of Lake Waunatta Woods, Just Off Of University, With Winter Park Address And Zoned For Winter Park Schools. Split Bedroom Floor Plan, With Large Gathering Spaces, As Family, Living And Dining Room Are Spacious. This Home...

Move In Ready Winter Park Home Available For Re...

NEW Photo of Listing #O5550563

$2,250 Active

  • 4 Beds
  • 3 Baths
  • 0.48 Acres
  • 1,802 ft²

Rental

2480 Temple Dr, Winter Park, FL

MLS® #O5550563

Move In Ready Winter Park Home Available For Rent! 1,800+ Square Foot Single Family House Zoned For Winter Park Schools! New Kitchen Counter Tops, Bathroom Renovation And Air Conditioning Unit. Call Today To Come See This Rental!

Rare Opportunity To Own An Oversized Lot In Win...

NEW Photo of Listing #O5550573

$549,000 Active

  • 3 Beds
  • 2 Baths
  • 0.48 Acres
  • 1,802 ft²

Residential

2480 Temple Dr, Winter Park, FL

MLS® #O5550573

Rare Opportunity To Own An Oversized Lot In Winter Park! Over 20,000 Square Foot Lot Available For Redevelopment Or Rental Opportunity. The Value Is In The Land In This 70x300 Lot. Rent Out The Home While Going Through The Design And Permitting Process Of A...

Winter Park Work & Play, Home With Office, Or C...

NEW Photo of Listing #O5550929

$695,000 Active

  • 4 Beds
  • 3 Baths
  • 0.3 Acres
  • 2,571 ft²

Residential

1345 Clay St, Winter Park, FL

MLS® #O5550929

Winter Park Work & Play, Home With Office, Or Can Easily Be A 4 Bedroom Home, Professional Office Zoning In Place, Great For Boutique Law Firm, Cpa, & Professional Uses. Convenient Winter Park Location On Clay Street Between Par Avenue And Fairbanks Avenue....

This Georgetown Townhome Is Located Within Walk...

NEW Photo of Listing #S4854541

$759,000 Active

  • 3 Beds
  • 3 Baths
  • 0.11 Acres
  • 2,422 ft²

Residential

1134 S Pennsylvania Ave, Winter Park, FL

MLS® #S4854541

This Georgetown Townhome Is Located Within Walking Distance To Park Ave, Rollins College And Historic Winter Park. As You Enter This Home You Are Greeted With A Tiled Foyer And A Formal Living / Dining Room Separated By A Gas 2 Sided Fireplace. Hardwood Flo...

Another Unique Clarkson Concepts Home Just Comp...

NEW Photo of Listing #O5551161

$835,700 Active

  • 4 Beds
  • 3 Baths
  • 0.2 Acres
  • 3,008 ft²

Residential

2525 Brookshire Ave, Winter Park, FL

MLS® #O5551161

Another Unique Clarkson Concepts Home Just Completed In Brookshire Heights. Close To Historic Park Avenue, Dining And Shopping, And The Winter Park High School District. Quality And Attention To Details Is Evident The Moment You Exit Your Car. Ipe Wood Is N...

The Property Has Been Annexed Into The City Of ...

NEW Photo of Listing #O5551266

$900,000 Active

  • 0.66 Acres

Land

1230 Formosa Ave, Winter Park, FL

MLS® #O5551266

The Property Has Been Annexed Into The City Of Orlando And Has Been Re-zoned To R-2b/t/w For Future Development Of 12 Townhomes. The Land Has Been Cleared And Ready For Development. Great Access To I-4 And The Area Is Ripe For Development.

Detailed And Unique Describes This Brand New 4 ...

NEW Photo of Listing #O5551438

$5,000 Active

  • 4 Beds
  • 3 Baths
  • 0.17 Acres
  • 2,802 ft²

Rental

1601 Chestnut Ave, Winter Park, FL

MLS® #O5551438

Detailed And Unique Describes This Brand New 4 Bedroom 3 Bath Pool Home Located In The Much Desired Winter Park Community. You Are The First To Live Here! As You Step Inside You Will Notice The Beautiful Wood Flooring, Contemporary Lighting Fixtures, Quartz...

This Beautifully Remodeled 3 Bed - 2 Bath Corne...

NEW Photo of Listing #O5551498

$284,900 Active

  • 3 Beds
  • 2 Baths
  • 0.27 Acres
  • 1,814 ft²

Residential

5420 Justine Way, Winter Park, FL

MLS® #O5551498

This Beautifully Remodeled 3 Bed - 2 Bath Corner Lot Home Is In Excellent Condition And Is Located In Desirable Winter Park. Enjoy A Winter Park Address And Seminole County Schools! This Home Has Been Completely Renovated. The Home Has A Gorgeous New Kit...

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 December 15th, 2017 at 3:03am EST.