Winter Park

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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.

Community Summary

Homes for Sale

The price range for this neighborhood is from $0 to $6,900,000

468 Total Listings
$761,457 Average Price
2,434 Average Square Feet
250 Average Price / SqFt

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
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570 Seminole Dr, Winter Park

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 private driveway, just off of quite brick paved

1016 Genius Dr, Winter Park

6 Beds, 9 Baths, 10.3k SqFt
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 award-winning home was designed by Bernie Johnson

1941 Legion Dr, Winter Park

6 Beds, 9 Baths, 10.5k SqFt
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 vacuum, custom built-ins, surround

2040 Venetian Way, Winter Park

6 Beds, 8 Baths, 7,677 SqFt
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 bedroom/7 ½ bath, pool home was designed by Slocum Platts Architects and built by Maroon Fine Homes. Lake views from almost every room in the home. All of the ceilings in the main living areas are coffered and uniquely designed using Ipe and Pecky Cypress wood

740 Palmer Ave, Winter Park

5 Beds, 5 Baths, 4,810 SqFt
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 and one down. Room for an expansive, gourmet kitchen.

540 N Interlachen Ave, Winter Park

3 Beds, 5 Baths, 5,249 SqFt
Beautiful James Gamble Rogers New England Colonial Revival style Lakefront estate home in the heart of downtown Winter Park. Limed brick façade, brick driveway and patios and lush landscaping make this an elegant setting. Built in 1933 and Updated in 2000 with custom built in cabinetry through out almost every room, the finest millwork, upgraded lighting and designer finishes. Impeccably maintained with careful attention to all the details.

1637 Chase Landing Way, Winter Park

5 Beds, 6 Baths, 6,272 SqFt
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 large covered dock has a motorized lift that’s perfect for your boat, jet

2150 Via Tuscany, Winter Park

7 Beds, 10 Baths, 7,670 SqFt
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 includes features so seldom found in today’s homes including brick laid floors, wood beam ceilings, formal living and dining rooms, three brick fireplaces, a gourmet kitchen that opens to the family room, downstairs master retreat, home office, movie

472 Henkel Cir, Winter Park

4 Beds, 7 Baths, 4,686 SqFt
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 conditioned living area with bright - wide open floor plan, clean lines, neutral designer interiors , 10'8" architectural ceilings, expansive picturesque windows/doors thru-out, 10’ Casablanca folding LaCantina doors, 4 bedroom suites w/ Master down, 2nd

975 Greentree Dr, Winter Park

4 Beds, 5 Baths, 5,731 SqFt
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 and quality in craftsmanship with this home is outstanding… Located on a quiet tree-lined dead end street walking distance or a short boat ride across the lake to downtown Winter Park! Flexible open, yet warm traditional interiors with spacious

1127 Preserve Point Dr, Winter Park

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 available for a gorgeous 9782 sq. ft. home that was

639 N Park Ave, Winter Park

3 Beds, 5 Baths, 4,237 SqFt
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 stretch of Park Avenue that encompasses downtown

Winter Park Neighborhoods

Winter Park

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.