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, Resort-style Pool, And More! Offering Formal Living Areas, Gourmet Chef’s Kitchen, Open Great Room, His And Her Home Offices, Elevator, 12-person Home Theater, Billiard Room, And Six Guest Suites,... 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 From Famed Park Avenue, This Lot, With Its Prevailing Breezes, Towering Cypress Trees And Breathtaking Lake View Will Inspire Visions Of The Most Elegant Of Estate Homes. Located Down A Long Oak Lined... Read More

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Courtesy of Stockworth Realty Group
  • $6,745,000
  • 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 College Chapel And Downtown Orlando Illuminated In The Evening. This Property Is On A Private Street With Only 2 Other Lakefront Homes And The Only Gated Lakefront Street In All Of Winter Park! This... Read More

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Courtesy of Coldwell Banker Residential Re
  • $4,950,000
  • Single Family Home
  • 5
  • 9,838
  • 4
  • 1989
  • Macdonald Robert Dhu Pk
  • O5564470

Stunning Lakefront Estate In Premier Location Within Walking Distance To Park Ave… Situated On 1.5 Acres With 280' Of Lake Frontage On Lake Maitland – 6 Lake Chain Of Lakes. Enjoy Lake Views From Almost Every Room Including The Grand Master Suite, Formal Living Room With Wood Burning Fireplace, Elegant Entry And Kitchen That Leads To Sunroom. The Spacious Backyard With Pristine Landscaping... Read More

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Courtesy of Coldwell Banker Residential Re
  • $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 & Below Appraisal!! The Living & Entertaining Areas Are Spacious & Elegant, W/ Sweeping Views Of The Lake From Almost Every Room. High End Finishes In The Main House Include French Doors, Central... Read More

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Courtesy of Fannie Hillman & Associates
  • $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 Side Of Lake Maitland, This 5 Bedroom, 7,600 Sf Home Features Formal Living Areas, A Home Office, Downstairs Master And Guest Suite, Upstairs Bonus Room, A Game Room With A Temperature Controlled Wine Chateau, Heated Pool, A Private Boathouse, And 4-car Garage. Beautiful Travertine And Wood Floors Flow Throughout The... 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 Venetian Canal). Amazing Architecture, Both Inside And Out. Grand Foyer With Spiral Staircase. Formal Living Areas With Panoramic Views Of The Majestic Oaks And Lake. Double Master Suites, One Upstairs... 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). There Are Five Very Beautiful Large Oak Trees, One Is About 350 Years Old And 15 Cypress Trees On The Water. It Is By Far The Best Available Vacant Lot On The Winter Park Chain Of Lakes. Plans Are... Read More

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Courtesy of Kelly Price & Company Llc
  • $3,350,000
  • Townhouse
  • 5
  • 4,244
  • Park Hill
  • 3
  • 5,095
  • 2018
  • Park Hill
  • O5565224

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 Ever Built In Winter Park. Designed By Award Winning Slocum Platts Architects, Park Hill's Classically Styled Architecture Will Likely Be The Only Remaining New Residential Construction Along The Famed... Read More

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Courtesy of Coldwell Banker Residential Re
  • $3,350,000
  • Townhouse
  • 5
  • 4,237
  • Park Hill
  • 3
  • 5,088
  • 2018
  • 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 Ever Built In Winter Park. Designed By Award Winning Slocum Platts Architects, Park Hill's Classically Styled Architecture Will Likely Be The Only Remaining New Residential Construction Along The Famed... 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 Detail, Workmanship And Quality Is Unapparelled. Designed By Architects-lucia Kassik & Monday, Grant Gribble Interiors, Landscape Architect- Frank Joseph Brooks And Built By Victor Farina. 130 Feet Of... 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 Extensively Renovated In 2008-2009. Enjoy The Florida Luxury Lifestyle While Relaxing In Your Private Pool And Spa Or Entertain Your Friends And Family With A Full Outdoor Kitchen And Huge Patio Area. The... Read More

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Courtesy of Premium Properties R.e Service
  • $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 Detail, This Stunning Four Bedroom Home Offers Four Full Baths, Three Half-baths, A Detached One Bedroom + Living Quarters Guest House, A Home Fitness Center, Boathouse & More! The Chef’s Kitchen... 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 Peaceful Cul-de-sac And Faces West For Sunset Views Nightly. Most Of The Lot Has Been Cleared With The Exception Of Some Well Established Oaks And Cypress Trees Near The Shoreline.

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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 This Home Has Every Option Imaginable. Every Option Was Hand Picked And Crafted To Rest On Just Over Acre With Fantastic Views And Designed To Have Views Lake From Practically Every Room In The House.... 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 Every Room. Entertain Large Parties Simply With The Spacious And Commercial Grade Kitchen, Grand Family And Living Rooms, And Resort-like Courtyard. Display Art, Cars, Or Rvs In The Oversized Heated... 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 Interlachen Place Is Around The Corner From World Famous Park Avenue, Across The Street From The Alfond Inn And Just A Stone’s Throw From The Winter Park Chain Of Lakes. Comprised Of Six Exquisitely... Read More

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Courtesy of Premier Sothebys Intl. Realty
  • $2,850,000
  • Single Family Use
  • Windsong/
  • Winter Park
  • O5573209

Now Is Your Chance To Build Your Dream House Near Windsong Subdivision In Winter Park. Amazing Waterfront Property Is On Mizell Lake /chain Of Lakes. Home Site Has Been Cleared And Ready For You To Build.

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Courtesy of Keller Williams Advantage 2 Realty
  • $2,850,000
  • Single Family Home
  • 6
  • 6,378
  • 6
  • 1982
  • Anchorage Estates
  • O5570431

Gorgeous, One-of-a-kind French Estate, In Olde Winter Park! 3-blocks From Park Avenue, Walk To The Winter Park Golf Course, Boutique Shops, Award-winning Restaurants And More. Immaculate Interior Boasts Over 6,300 Sf Of Luxurious Living With High-end Custom Details Throughout. From The French Inspired Copper Dome Entrance To The Grand Foyer And Elegant Staircase, Marble/onyx Flooring, And 5... Read More

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Courtesy of Kelly Price & Company Llc
  • $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 Standards, Yet Express’s The Character, Warmth, And Architecture Of The 1930’s. The Unique Private Setting Offers Privacy, Quiet Seclusion, And Clear Expansive Views Throughout The Home Of Lake Osceola.... Read More

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Courtesy of Fannie Hillman & Associates
  • $2,675,000
  • 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 Winter Park. Enter The Privacy Of A Long Driveway Surrounded By Gardens Arriving To A Spacious French Provencal Styled Home, Guest Quarters And Four Bay Garage. This Elegant Styled Home Is Perfect... Read More

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Courtesy of Fannie Hillman & Associates
  • $2,650,000
  • Townhouse
  • 4
  • 3,180
  • Park Hill
  • 3
  • 4,055
  • 2018
  • 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 Ever Built In Winter Park. Designed By Award Winning Slocum Platts Architects, Park Hill's Classically Styled Architecture Will Likely Be The Only Remaining New Residential Construction Along The Famed... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,600,000
  • Single Family Home
  • 6
  • 5,374
  • 4
  • 7,122
  • 2009
  • Lords Sub
  • O5565630

Gorgeous Mediterranean Style Estate In The Heart Of Winter Park. Situated On Lake Killarney, This Custom Residence Has Character And Style. A Spiral Staircase Constructed Of Travertine And Oak Wooded Stairs Greets You With Grand Style. Off The Foyer You Will Find The Main Office That Has Custom Wood Cabinetry And A Coffered Style Ceiling Made Of Solid Oak. Off The Main Living Area, You Will Find... Read More

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Courtesy of Premier Sothebys Intl. Realty
  • $2,500,000
  • Single Family Home
  • 7
  • 4,422
  • 5
  • 6,286
  • 2014
  • Sicilian Shores Rep 02
  • O5567355

Exquisitely Crafted Traditional Five-bedroom, Six-bath Home In The Heart Of The Exclusive Winter Park Vias. This Beautiful Home Is Situated On A Stunning Oversized Lot With Mature Landscaping Moments Away From Beautiful Lake Maitland, Perfectly Located A Short Stroll From The Winter Park Racquet Club. The Traditional Yet Open Floor Plan Allows For Both Formal And Casual Living, Perfect For... Read More

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Courtesy of Premier Sothebys Intl. Realty
  • $2,350,000
  • 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 Such As Hand Hewn Beams And Vaulted Ceiling In The 27 Ft Long Great Room, Plaster Walls, Four Fireplaces And Wood Floors. The Sellers Added A Luxurious Pool, A New Garage With Attached Large Guest... Read More

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Courtesy of Coldwell Banker Residential Re
  • $2,249,000
  • Single Family Home
  • 6
  • 5,003
  • 5
  • 6,405
  • 2007
  • Winflor Court Pt Rep
  • O5557629

A Charming Brick Street Invites You To This Exceptionally Custom Built Estate In The Heart Of Winter Park & Walking To Park Avenue. This Home Features Five Bedrooms, Five & A Half Baths, With Over 5,000 Sq. Ft., 3-way Split Plan With Downstairs Master, Boasts Impressive Craftsmanship And Spectacular Views To Pool And Yard With A California Napa-inspired Cabana. A Stone Fireplace & Old Growth... Read More

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Courtesy of Premier Sothebys Intl. Realty
  • $2,195,000
  • Single Family Home
  • 6
  • 6,204
  • 5
  • 7,643
  • 2001
  • Osceola Or Lakeview Deed
  • O5570851

Magnificent Spanish Estate In The Heart Of Winter Park. This 5 Bedroom, 6 Bath Home Has Great Curb Appeal With Immaculate Landscaping And Quality Finishes Throughout The Interior, Such As High Ceilings, Detailed Craftsmanship, And The Finest Tile And Millwork. Beautiful Arched Entry Doors Welcome You Into This Exceptional Home, As You Enter Into An Entrance Hall With Formal Dining Room On Your... Read More

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Courtesy of Core Community Realty Llc
  • $2,194,000
  • Townhouse
  • 5
  • 3,244
  • 2
  • 4,935
  • 2016
  • South Interlachen Place
  • O5522049

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 Interlachen Place Is Around The Corner From World Famous Park Avenue, Across The Street From The Alfond Inn And Just A Stone’s Throw From The Winter Park Chain Of Lakes. Comprised Of Six Exquisitely... Read More

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Courtesy of Premier Sothebys Intl. Realty
  • $2,150,000
  • 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 Corner Of The Fourth Floor Has Views To The North, East And South With Three Private Covered Balconies. Your Key Fob Grants You Elevator Access To Your Own Private Foyer That Leads Through Double Doors... Read More

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Courtesy of Florida One Real Estate Llc
  • $2,000,000
  • 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 Maitland. This 5 Bedroom, 3/12 Bath House With Pool, 3 Car Garage, And Boathouse Was Extensively Remodeled In 2006 With Open Concept, Electrical And New Plumbing. You Enter Into A Vaulted Wood Beam... Read More

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Courtesy of Peacock Realty International

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