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
  • $7,500,000
  • Single Family Home
  • 11
  • 10,600
  • 7
  • 2009
  • J Kronenberger Sub
  • O5541737

Stunning Mediterranean Lakefront Estate. Across From The Secret Gardens Of Kraft Azalea Park Sits This Palatial 1-acre Compound With Over 10,000 Sf Of Luxurious Living Space, Private Tennis Court,... Read More

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Courtesy of Kelly Price & Company Llc
  • $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
  • $4,950,000
  • Single Family Home
  • 6
  • 4,681
  • 5
  • 5,904
  • 1989
  • Twelve Oaks
  • O5544700

Called Winter Park’s Finest Location, Twelve Oaks Peninsula, Is A Unique And Truly Exceptional Opportunity In The Heart Of Winter Park! A Quiet, Private Drive Leads To This Stately Custom-built... Read More

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Courtesy of Fannie Hillman & Associates
  • $4,850,000
  • 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
  • $3,995,000
  • Single Family Home
  • 7
  • 6,763
  • 6
  • 9,129
  • 1991
  • Camwood
  • O5549098

Stunning 6 Bedroom, 6.5 Bath Lakefront Estate On Lake Maitland. Located In One Of Winter Park’s Premier Communities, You’re Less Than 1 Mile Away From Park Avenue And All Of The Award-winning... Read More

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Courtesy of Kelly Price & Company Llc
  • $3,450,000
  • Single Family Home
  • 9
  • 7,631
  • 5
  • 10,569
  • 2009
  • O5552108

Unbelievably Gorgeous Lakefront Estate Home In Winter Park! Located On The Quiet Lagoon Of Lake Maitland, This 5 Bedroom, 7,600 Sf Home Features Formal Living Areas, A Home Office, Downstairs Master... Read More

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Courtesy of Kelly Price & Company Llc
  • $3,450,000
  • 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
  • $3,450,000
  • 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
  • O5550590

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
  • $3,250,000
  • Single Family Home
  • 4
  • 4,057
  • 4
  • 6,179
  • 2008
  • Timberlane Shores
  • O5532667

Casa Fiera Vista ~ Rare Opportunity To Own An Elegant Custom Lakefront Estate Located On The Winter Park Chain Of Lakes. This Home Is An Aurora And Parade Of Homes Grand Winner! The Attention To... Read More

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Courtesy of Kelly Price & Company Llc
  • $3,200,000
  • Single Family Home
  • 6
  • 6,272
  • 5
  • 8,539
  • 2002
  • Windsong Preserve Point 43/76
  • O5522419

Huge Price Reduction!! 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... Read More

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Courtesy of Premium Properties R.e Service
  • $3,195,000
  • Single Family Home
  • 5
  • 5,992
  • 4
  • 7,613
  • 1989
  • Acreage & Unrec
  • O5557598

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, Character... Read More

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Courtesy of Coldwell Banker Residential Re
  • $3,190,000
  • 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
  • $3,150,000
  • Single Family Use
  • Windsong Preserve Point 43/76
  • O5552060

Rare Opportunity To Build Your Dream Home In The Heart Of Winter Park. This Waterfront Property Is In The Desirable Windsong Community And On The Winter Park Chain Of Lakes. It Is Located On A... Read More

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Courtesy of Fannie Hillman & Associates
  • $2,998,000
  • Single Family Home
  • 6
  • 9,011
  • 4
  • 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
  • $2,995,000
  • Single Family Home
  • 7
  • 8,910
  • 5
  • 21,497
  • 2013
  • Winter Park
  • O5536500

Step Into This Dramatic Mid-century Modern Home And You'll Never Want To Leave. Enjoy The Perfection Of The Glass Porcelain Floors And Dramatic Windows, As You Overlook The Spectacular Courtyard From... Read More

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Courtesy of Charles Rutenberg Rlty Orlando
  • $2,978,000
  • Townhouse
  • 5
  • 4,160
  • 3
  • 6,132
  • 2016
  • South Interlachen Place
  • O5537925

Under Construction. Completion Is Scheduled For Spring, 2018. Only Two Residences Remain. Your Opportunity To Own Unprecedented Luxury In The Most Exclusive Area Of Winter Park Has Arrived. South... Read More

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Courtesy of Premier Sothebys Intl. Realty
  • $2,895,000
  • Single Family Home
  • 6
  • 5,022
  • 5
  • 6,859
  • 1992
  • Green Oaks Rep
  • O5557186

Welcome Home To This Exquisite Waterfront Property With Connecting Guest Cottage Offering Privacy On All Sides. It's Full Of Light With Morning Sunrise Views Of The Isle Of Sicily On Lake Maitland In... Read More

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Courtesy of Fannie Hillman & Associates
  • $2,750,000
  • Single Family Home
  • 8
  • 5,862
  • 5
  • 7,250
  • 2017
  • Sicilian Shores Rep 02
  • O5538382

Breathtaking Contemporary Pool Home In The Heart Of The Winter Park Via’s. This Newly Constructed Home Sits High Over The Street On An Oversized Lot And Has All The Modern Amenities And... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,695,000
  • Single Family Home
  • 4
  • 5,409
  • 5
  • 5,994
  • 1930
  • Winter Park
  • O5559096

This Authentic 5 Bedroom Spanish Mediterranean Lakefront Estate Is Now Available In Winter Park, Florida. Woven Into The History Of Winter Park, The Home Is Comfortably Updated To Today’s... Read More

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Courtesy of Fannie Hillman & Associates
  • $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 And Exclusive Address With Only Eight Single-floor Residences. Construction Of Interlachen North Condominium Is... Read More

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Courtesy of Premier Sothebys Intl. Realty
  • $2,495,000
  • Single Family Home
  • 5
  • 4,949
  • 4
  • 6,413
  • 1938
  • Dyer Susan Resub
  • O5554384

Stunning Downtown Winter Park Character Home Beautifully Updated And Renovated On .97 Acres Of Prime Land. Originally Built In The 1930s This Remarkable Home Has Elegant Craftsmanship Throughout... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,495,000
  • 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
  • $2,490,000
  • Single Family Home
  • 8
  • 5,099
  • 6
  • 6,696
  • 2006
  • Kronenberger J
  • O5556141

This Stunning 6 Bdm/8 Ba Mediterranean Plus Office Is The Epitome Of Timeless Elegance. The Luxurious Estates' Master Craftsmanship Located On The Brick Paved Streets Of Olde Winter Park, Impresses... Read More

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Courtesy of Mainframe Real Estate
  • $2,350,000
  • Single Family Home
  • 6
  • 5,003
  • 5
  • 6,405
  • 2007
  • Winflor Court Pt Rep
  • O5557629

A Charming Brick Street Invites You To This Exceptional European Estate, Custom Built Home By Carlos Posada. This Home Features Five Bedrooms, Five & A Half Baths, With Over 5,000 Sq. Ft., Three-way... Read More

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Courtesy of Premier Sothebys Intl. Realty
  • $2,350,000
  • Single Family Home
  • 5
  • 3,978
  • 4
  • 4,775
  • 1957
  • Osceola Shores Sec 03
  • O5556843

This Is A Wonderful Opportunity To Own A Gorgeous Winter Park Lakefront Estate With 287’ Of Frontage On Lake Osceola. Located On A Point Of Land At The End Of A Cul-de-sac, This Unique Property... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,325,000
  • Single Family Home
  • 5
  • 5,082
  • 4
  • 6,651
  • 2015
  • Forest Hills
  • O5528444

Stunning Custom French Country 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 That Highlights... Read More

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Courtesy of Kelly Price & Company Llc
  • $2,200,000
  • Condo
  • 5
  • 4,090
  • 3
  • 4,575
  • 2005
  • Residences
  • O5542364

Imagine Living In The Former Model For The Most Luxurious Condominium Buildings In Winter Park - The Residences,which Set The Standard For Luxury Living In Central Florida! The Vast Home On The... Read More

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Courtesy of Florida One Real Estate Llc
  • $2,199,000
  • Single Family Home
  • 4
  • 3,556
  • 5
  • 5,258
  • 1969
  • Maitland Shores
  • O5504575

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

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Courtesy of Peacock Realty International

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