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 All... Read More

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Courtesy of Fannie Hillman & Associates
  • $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
  • $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
  • $3,700,000
  • 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
  • $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
  • $3,450,000
  • 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
  • $3,295,000
  • 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
  • $3,295,000
  • 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
  • $2,795,000
  • 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
  • $2,795,000
  • Single Family Home
  • 6
  • 6,026
  • 4
  • 1991
  • Kronenberger J
  • O5511707

Elegant "canal Front" Estate On "chain Of Lakes" Recently Completely Remodeled & Tastefully Enhanced With Modern Transitional Interiors... Premier Setting Walking Distance To Park Avenue On An... 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
  • $2,596,500
  • 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
  • $2,390,000
  • Single Family Home
  • 5
  • 4,465
  • 6
  • 5,706
  • 1972
  • Green Oaks Rep 02
  • O5475835

Amazing Opportunity To Own A Private And Quietly Tucked Away Home On The Shores Of Lake Maitland. Six Bedrooms, Four And One-half Baths, And Over 4,400 Sf Of Sprawling Interior Living Space. ... Read More

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Courtesy of Kelly Price & Company Llc
  • $2,350,000
  • Single Family Home
  • 5
  • 5,082
  • 4
  • 6,651
  • 2015
  • Forest Hills
  • O5528444

Stunning Keith Groninger French Country Custom Estate. Built In 2015 And Featured In Parade Of Homes, This Magnificent Eco-friendly Home Features 4 Bedrooms, 5 Full Baths And A Luxurious Interior... Read More

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Courtesy of Kelly Price & Company Llc
  • $2,250,000
  • Single Family Home
  • 6
  • 5,398
  • 5
  • 5,891
  • 1973
  • Woodmere Terrace Rep
  • O5515214

Beautifully Updated Open Concept Transitional Home In The Winter Park “via’s”! Original Home Was Torn Down W/only A Chicago Brick Wall Remaining So Effective Year Built Is 1992. Just Completed... Read More

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Courtesy of Fannie Hillman & Associates
  • $2,250,000
  • Single Family Home
  • 5
  • 6,831
  • 4
  • 8,429
  • 2010
  • Windsong Lakeside Sec 02 43/71
  • O5489207

Magnificent European French Estate In Windsong. Built By Carlos Posada And Designed By A Famed Atlanta Architect, William Baker. The Exquisite Details In This Home Are Extensive Including A Slate... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,200,000
  • Single Family Home
  • 11
  • 9,757
  • 7
  • 9,757
  • 1989
  • Comstock Park
  • O5475027

This Stunning Estate Sits On A Double Lot Of Almost Half An Acre On One Of Winter Park's Finest Streets With Close Access To Downtown Winter Park And The Newly Finished Winter Park 9. This Beautiful... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $2,200,000
  • Condo
  • 3
  • 1,952
  • 3
  • 1,952
  • 1971
  • Cloisters Condo
  • O5525235

An Immaculate, Serene, Direct Lakefront Condominium, Just Steps From Park Avenue's Finest Shop & Restaurants. A Rare Opportunity To Own A Home On The Winter Park Chain. This Tranquil & Amazing... Read More

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Courtesy of Winter Park Land Co.
  • $2,199,000
  • Single Family Home
  • 4
  • 3,556
  • 5
  • 5,258
  • 1969
  • Maitland Shores
  • O5504575

Elegant Italian Country Villa – An Exceptional Lagoon Front Home Located On Approximately An Acre Of Land In The “heart Of The Vias” In Winter Park With Canal Access To Lake Maitland. This 5... Read More

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Courtesy of Peacock Realty International
  • $2,199,000
  • Single Family Home
  • 5
  • 5,967
  • 5
  • 7,977
  • 1947
  • Forrest Hills
  • O5517691

Spectacular James Gamble Rogers Ii Mediterranean Waterfront Estate. This Masterpiece Boasts Magnificent Views And Sunsets Overlooking Lake Sue. Built In 1947, The Timeless Design Of This Home... Read More

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Courtesy of Fannie Hillman & Associates
  • $2,195,000
  • Single Family Use
  • Osceola Shores Sec 03
  • O5533194

Lakefront Property With 100 Feet Of Frontage On Lake Osceola On The Winter Park Chain Of Lakes. A Rare Opportunity To Build Your Dream Home On This Fantastic Lot Located On A Quiet Cul-de-sac Street!... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,195,000
  • Single Family Home
  • 7
  • 6,071
  • 6
  • 7,973
  • 2007
  • Windsong Lakeside Sec 02 43/71
  • O5518637

Beautiful Six Bedroom, Six And One-half Bath Custom Windsong Pool Home! Well Appointed Living Spaces Featuring Hardwood And Travertine Tile Floors, And Volume Ceilings. Enjoy The Ambiance Of A Gas... Read More

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Courtesy of Core Community Realty Llc

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