Winter Park Florida Homes & Condos

While there are a number of communities and neighborhoods in the Greater Orlando Area that are appealing to both visitors and full-time residents, Winter Park Florida is considered one of the favorite areas to live in Orlando. Some of the world's top attractions are found in Orlando, and everything from the nightlife to the shopping to the dining is truly some of the best in the country.

Many people prefer the city of Winter Park, because it allows for quick access to the city but still feels like an independent suburban community all of its own.

Winter Park's Statistics

Winter Park, located in Orange County, boasts a population of 28,000, as of the most recent census. It occupies just over 10 square miles, although 1.5 of those square miles are lakes. Winter Park is located just seven miles due north of Downtown Orlando, a journey that typically takes under 10 minutes by car.

The History of Winter Park

Although the Muscogee and the Seminoles were the first to call Winter Park home, the city itself wasn't settled by Europeans until the end of the 19th century. Quickly, however, it became a favorite spot of wealthy magnates who came specifically to the area for the warm climate and water sports available in the winter.

This coincided with the construction of the railway system heading down to this part of the state, making it easier than ever before for people from the Northern United States to visit by train during the winter. At least three presidents, including Arthur, Roosevelt and Obama have visited Winter Park in the past.

Schools in Winter Park

Most residents in Winter Park will be served by the Orange County Public School System. Winter Park is home to six elementary schools, two middle schools and one high school.

The public school in Winter Park with the highest rating is Audubon Park Elementary School, which is notable for its small class sizes and impressive test scores. Within a 15-minute drive, there are also more than a dozen preparatory academies, religious schools and college campuses for a full range of educational opportunities.

The Appeal of Calling Winter Park Your Home

Winter Park is a very pedestrian-friendly city, and many residents feel safe walking to local restaurants or even having their children ride bikes unsupervised to a friend's home. You'll be close to art museums as well as high-quality restaurants, and Downtown Winter Park is well-known for its blossoming culinary scene. Winter Park is a wonderful, inviting place to live, and it even offers the convenience and amenities of a major urban area just minutes away in Orlando.

Winter Park, Florida, might be your dream destination if you love access to culture, proximity to a major city and lots of scenic, warm outdoor recreation opportunities throughout the year.

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Properties For SaleSold Properties
  • $6,900,000
  • Single Family Use
  • Winter Park Old Town
  • O5439246

This 2.25 Acre Lake Front Crown Jewel Is A Once-in-a-lifetime Offering Of One Of Old Winter Park’s Most Prestigious Estate Lots. Situated High Above Expansive Lake Osceola And Only A Short Walk... Read More

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Courtesy of Stockworth Realty Group
  • $6,795,000
  • Single Family Home
  • 9
  • 10,314
  • 6
  • 14,516
  • 2005
  • Windsong Ests Sec 1
  • O5496008

Incredible 2-acre Modern Mediterranean Lakefront Estate On Hidden Peninsula Between Lake Mizell & Virginia On The 6-lake Chain Of Lakes… Enjoy Both Picturesque Sunrises & Sunsets With Rollins... Read More

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Courtesy of Coldwell Banker Residential Re
  • $4,895,000
  • Single Family Home
  • 9
  • 10,493
  • 6
  • 15,677
  • 2008
  • Green Oaks Rep 02
  • O5484879

Luxurious Lake Maitland Estate! This Winter Park Chain Of Lakes Custom 5 Car Garage Home Has Panoramic Views Of Lk. Maitland W/ 175' Of Water Frontage On 1.09 Acres. This Magnificient Home Has It... Read More

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Courtesy of Fannie Hillman & Associates
  • $4,595,000
  • Single Family Home
  • 8
  • 7,224
  • 5
  • 1925
  • The Ellno Willo
  • O5493376

One Of Winter Park’s Most Premier And Timeless Traditional Lakefront Estates Elevated On Apprx. 1.5 Acres And 200’ Of Lake Frontage On Lake Virginia Walking Distance To Rollins College And Famed... Read More

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Courtesy of Coldwell Banker Residential Re
  • $4,500,000
  • Single Family Home
  • 8
  • 7,677
  • 6
  • 10,194
  • 2002
  • Maitland Shores
  • O5486486

Elegant Mediterranean Lakefront With Over An Acre Of Land In The “heart Of Winter Park” With 227ft. Of Lakefront, The View Is One Of The Most Breathtaking On The Winter Park Chain. This 6... Read More

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Courtesy of Fannie Hillman & Associates
  • $4,250,000
  • Single Family Home
  • 5
  • 4,259
  • 5
  • 6,221
  • 1914
  • Alabama
  • O5468354

Extraordinary Winter Park Chain Of Lakes Opportunity With 1.8 Buildable Acres! Incredibly Large 79,409 Square Feet Tract Of Direct Lakefront Property On Lake Osceola With 231.4 Ft Of Shoreline And... Read More

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Courtesy of Coldwell Banker Residential Re
  • $4,250,000
  • Single Family Use
  • O5498770

Winter Park Chain Of Lakes Estate Site With Opportunity To Build New Or Restore. 5.06 Acres Per Tax Rolls With Riparian Rights. Buildable Acreage Of 1.82 Acres. City Says Can Put Up To 26,162... Read More

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Courtesy of Coldwell Banker Residential Re
  • $3,950,000
  • Single Family Home
  • 5
  • 4,810
  • 5
  • 6,741
  • 1955
  • Osceola Place
  • O5509686

Never Before On The Market This Is A Rare Opportunity To Own A Piece Of Winter Park History! Gorgeous 1955 Gamble Rogers Home With Double Waterfrontage (155’ On Lake Osceola, 235’ On The... Read More

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Courtesy of Kelly Price & Company Llc
  • $3,700,000
  • Single Family Home
  • 6
  • 6,272
  • 5
  • 8,539
  • 2002
  • Windsong Preserve Point 43/76
  • O5522419

This Amazing 2 Story Lakefront Home Is Located In Winter Park’s Exclusive Windsong Preserve Point Neighborhood And Features Stunning Views Of Lake Berry. The House Was Extensively Renovated In... Read More

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Courtesy of Premium Properties R.e Service
  • $3,595,000
  • Single Family Home
  • 5
  • 5,731
  • 4
  • 7,613
  • 1989
  • Acreage & Unrec
  • O5519106

Elegant Charleston Style Lakefront Residence In Secluded Setting On Premier Lake Osceola Overlooking An Absolutely Gorgeous, Tranquil Cove! Sophisticated Home Where The Attention To Detail,... Read More

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Courtesy of Coldwell Banker Residential Re
  • $3,500,000
  • Single Family Home
  • 10
  • 7,670
  • 7
  • 11,859
  • 2002
  • Adair Place
  • O5398109

Timeless Perfection Encompasses Every Room Of This Stunning Winter Park Estate. Custom Built By Charles Clayton, This Seven Bedroom, Seven Bath Home Exudes Character And Charm Throughout And... Read More

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Courtesy of Kelly Price & Company Llc
  • $3,495,000
  • Single Family Home
  • 7
  • 4,686
  • 4
  • 6,358
  • 2017
  • Thomas M Henkels Add
  • O5517710

Just Completed – 2017 New Contemporary Lakefront Masterpiece On Chain Of Lakes And Convenient Walking Distance To Downtown Winter Park / Park Ave And Alfond Inn…! Approx 5,000sf Of Air... Read More

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Courtesy of Coldwell Banker Residential Re
  • $3,450,000
  • Single Family Use
  • Windsong Preserve Point 43/76
  • O5504034

Located In Windsong On A Quiet Cul-de-sac Only 10 Minutes From Downtown Orlando. This Lot Faces West And Overlooks Rollins College. The Total Square Footage Of The Lot Is 64,407 Sq. Ft. (1.48 Acres).... Read More

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Courtesy of Kelly Price & Company Llc
  • $3,350,000
  • Townhouse
  • 5
  • 4,237
  • Park Hill
  • 3
  • 5,088
  • 2017
  • Park Hill
  • O5513210

Under Construction... Park Hill, An Ultra-luxury 10 Townhome Project By Hill Gray Seven Llc (only 5 Remaining), Is A Once-in-a-lifetime Opportunity To Own The Most Exclusive And Luxurious Townhome... Read More

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Courtesy of Coldwell Banker Residential Re
  • $3,295,000
  • Single Family Home
  • 4
  • 4,908
  • 4
  • 5,924
  • 1928
  • Ellno Willo
  • O5500763

This Is The First Time In Almost 50 Years This Amazing Mediterranean Lakefront Estate Has Been Available For Purchase. Located Just Blocks From Park Avenue On The Shores Of Lake Virginia You Can... Read More

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Courtesy of Coldwell Banker Residential Re
  • $3,195,000
  • Single Family Use
  • Lt A Blk A Rep
  • O5510336

Premier Park Avenue Lakefront Lot Situated On Just Under An Acre In The Downtown Corridor On Lake Maitland. Expansive Long And Wide Elevated Views Of The Lake Are Enjoyed Surrounded By Canopy Of... Read More

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Courtesy of Coldwell Banker Residential Re
  • $3,150,000
  • Single Family Home
  • 8
  • 6,025
  • 5
  • 8,418
  • 2007
  • Thomas M Henkels
  • O5473303

Come Enjoy Florida Living At Its Best With This Gorgeous Craftsman Style Home, Featuring Approximately An Acre Of Land And 200’ On Lake Mizell. Impeccably Designed, With Attention To Every... Read More

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Courtesy of Kelly Price & Company Llc
  • $2,996,492
  • Single Family Home
  • 5
  • 9,111
  • 5
  • 11,352
  • 1994
  • Bear Gully Pointe
  • O5526618

Exclusive Lakefront Home In Bear Gully Point. This Majestic Home Rests On Private Bear Gully Lake. Home Was Constructed By The Original Owner Who Was A Private Home Builder For Over 30 Years, So... Read More

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Courtesy of Prime Realty Professionals Of Central Florida Llc
  • $2,990,000
  • Single Family Home
  • 7
  • 6,345
  • 5
  • 9,298
  • 2008
  • Virginia Heights
  • O5461972

This Rustic Modern Parade Of Homes Winner Was Custom Built With Extreme Care And Thought For The Most Discerning Buyer. No Detail Has Been Overlooked, Creating Spaces That Are Excellent For Both... Read More

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Courtesy of Palmano Group Re Brokerage Llc
  • $2,895,000
  • Single Family Home
  • 7
  • 6,882
  • 5
  • 8,870
  • 2003
  • Windsong Preserve Point 43/76
  • O5517496

Elegant Winter Park Lakefront Estate In The Highly Sought After Windsong Neighborhood At The End Of A Quiet Cul-de-sac On Private Ski Lake. The First Floor Master Retreat Has Panoramic Views Of The... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,878,000
  • Townhouse
  • 5
  • 4,160
  • 3
  • 6,132
  • 2016
  • South Interlachen Place
  • O5432319

Under Construction. Only Two Residences Remain! Your Opportunity To Own Unprecedented Luxury In The Most Exclusive Area Of Winter Park Has Arrived. South Interlachen Place Is Around The Corner From... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $2,800,000
  • Single Family Home
  • 8
  • 8,342
  • 5
  • 2004
  • Robert Dhu Macdonald Park
  • O5380685

Your Opportunity To Own A Masterpiece On The Most Prestigious Street In Central Florida! This Classic Estate Offers Elegance, Luxury And Entertainment In The Heart Of Desired Winter Park.... Read More

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Courtesy of Bhhs Florida Realty
  • $2,699,000
  • Single Family Home
  • 9
  • 7,048
  • 6
  • 9,636
  • 2007
  • Sicilian Shores
  • O5503925

Captivating Santa Barbara Mission Style Estate Home Tucked Away In The Desirable Via’s Of Winter Park. Unparalleled Privacy, Wonderfully Authentic, Gorgeous Entry Courtyard, Balcony, And French... Read More

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Courtesy of Fannie Hillman & Associates
  • $2,695,000
  • Single Family Home
  • 4
  • 5,409
  • 5
  • 5,994
  • 1930
  • Town Of Winter Park
  • O5500747

Timeless 1930 Mizner Mediterranean Lakefront Estate Steeped In Winter Park History With Long Views Across Lake Osceola. Updated To Today’s Standards With The Authentic Character Maintained To Keep... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,650,000
  • Townhouse
  • 4
  • 3,180
  • Park Hill
  • 3
  • 4,055
  • 2017
  • Park Hill
  • O5493399

Under Construction... Park Hill, An Ultra-luxury 10 Townhome Project By Hill Gray Seven Llc (only 5 Remaining), Is A Once-in-a-lifetime Opportunity To Own The Most Exclusive And Luxurious Townhome... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,650,000
  • Single Family Home
  • 5
  • 4,638
  • 4
  • 6,712
  • 2005
  • Maitland Shores
  • O5459844

Gorgeous Four Bedroom, Four And One Half Bath Pool Home With 65’ On Lake Maitland. Beautiful Hardwood Floors, Crown Moldings, Custom Built-ins, And High Ceilings Compliment The Home’s Interior... Read More

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Courtesy of Kelly Price & Company Llc
  • $2,596,500
  • Condo
  • 5
  • 3,293
  • 3
  • 3,751
  • 1966
  • Winter Park
  • O5517087

Pre-construction. To Be Built. Interlachen North Condominium Is Winter Park's Newest, Exclusive Address With Only Eight Single Floor Residences. Construction Of Interlachen North Condominium Is... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $2,495,900
  • Single Family Home
  • 7
  • 5,160
  • 5
  • 8,245
  • 2017
  • Stonehurst Estates
  • O5493487

Under Construction: Stunning Transitional Estate On A Gorgeous 100x230' Lot With Mature Oaks. From The Moment You Walk Thru The Private Entry Gates Into A 500sq.ft Open Courtyard With Fireplace,... Read More

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Courtesy of Woodruff Realty, Inc.
  • $2,450,000
  • Single Family Home
  • 5
  • 4,002
  • 4
  • 4,957
  • 1957
  • Osceola Shores Sec 03
  • O5490187

287' Of Lakefront With Northern Exposure On The Winter Park Chain Of Lakes!! This Is A Wonderful Opportunity To Own A Gorgeous And Sophisticated Winter Park Lakefront Estate On Lake Osceola. The... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,399,000
  • Single Family Home
  • 7
  • 6,607
  • 5
  • 8,662
  • 2008
  • Windsong Lakeside Sec 02 43/71
  • O5521671

Beautiful Windsong Community, 5 Bedrooms With 5 Full Baths And 2 Half. Hardwood Floors, Gourmet Kitchen Overlooking Pool With Summer Kitchen.

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Courtesy of Ottersen Realty Corp

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