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Explore Winter Park FL Real Estate: Luxury Living Awaits

Discover Winter Park, Florida, a highly sought-after, affluent community just north of Orlando, known for its elegant charm and sophisticated lifestyle. Tree-lined brick streets, vibrant Park Avenue with upscale boutiques and gourmet dining, world-class museums, and beautiful chain of lakes define this picturesque city. Winter Park real estate offers a diverse selection, from historic homes and luxury estates to charming bungalows, with a median sale price around $460,000 - $518,950 as of June 2025. Experience a rich cultural scene, top-rated schools, and abundant parks in this desirable Central Florida gem.

Property Listings

$8,950,000

7 bd 11 ba 11,255 Sq.Ft. For Sale

1120 PRESERVE POINT DR, WINTER PARK, FL 32789

MLS®: O6350054

$8,500,000

5 bd 6 ba 6,502 Sq.Ft. For Sale

1112 PRESERVE POINT DR, WINTER PARK, FL 32789

MLS®: O6312768

$6,600,000

4 bd 5 ba 4,636 Sq.Ft. For Sale

2661 VIA TUSCANY, WINTER PARK, FL 32789

MLS®: O6260493

$6,500,000

6 bd 6 ba 5,759 Sq.Ft. For Sale

887 GEORGIA AVE, WINTER PARK, FL 32789

MLS®: O6331715

$5,999,000

5 bd 6 ba 6,708 Sq.Ft. Pending

1240 HARDING STREET, WINTER PARK, FL 32789

MLS®: O6342506

$5,950,000

5 bd 6 ba 4,448 Sq.Ft. For Sale

1181 VIA CAPRI, WINTER PARK, FL 32789

MLS®: O6332790

$5,895,000

5 bd 9 ba 7,916 Sq.Ft. For Sale

1400 ALABAMA DR, WINTER PARK, FL 32789

MLS®: O6285791

$5,549,000

5 bd 6 ba 5,096 Sq.Ft. For Sale

698 N NEW YORK AVE, WINTER PARK, FL 32789

MLS®: O6318156

$5,495,000

5 bd 7 ba 7,278 Sq.Ft. For Sale

2211 AZALEA PL, WINTER PARK, FL 32789

MLS®: O6319674

$5,450,000

5 bd 6 ba 5,164 Sq.Ft. For Sale

1221 RICHMOND RD, WINTER PARK, FL 32789

MLS®: O6321906

$4,999,000

503 N INTERLACHEN AVE, WINTER PARK, FL 32789

MLS®: O6331207

$4,995,000

4 bd 7 ba 6,242 Sq.Ft. For Sale

1760 VIA VENETIA, WINTER PARK, FL 32789

MLS®: O6330261

Search Homes in the Area

Discover Winter Park, Florida: Central Florida's Premier Address for Luxury & Lifestyle

Nestled just north of Orlando, Winter Park, Florida, stands as a beacon of sophistication, historic charm, and an unparalleled quality of life. This affluent city is defined by its tree-lined brick streets, stunning parks, and a vibrant cultural scene, offering residents a blend of tranquil suburban living with cosmopolitan amenities. If you're seeking luxury homes in Winter Park, FL or an exceptional living experience, this highly desirable area delivers.

Why Winter Park is a Coveted Destination:

Elegant Lifestyle & Cultural Richness: Winter Park is synonymous with refined living. Its iconic Park Avenue serves as the heart of the city, boasting an exquisite collection of upscale boutiques, art galleries, and acclaimed restaurants and cafes. Enjoy a leisurely stroll, indulge in gourmet dining, or browse unique shops. The city is also a hub for arts and culture, home to institutions like the Charles Hosmer Morse Museum of American Art (housing the world's most comprehensive collection of Tiffany glass), the Rollins College Art Museum, and the Albin Polasek Museum & Sculpture Gardens. Year-round events, including the prestigious Winter Park Sidewalk Art Festival and the Winter Park Farmers' Market, foster a strong sense of community and provide endless entertainment.

Natural Beauty & Outdoor Recreation: Beyond its urban elegance, Winter Park offers abundant green spaces and sparkling lakes. The Chain of Lakes, including Lake Virginia, Lake Osceola, and Lake Maitland, provides opportunities for boating, paddleboarding, and scenic tours. Picturesque parks like Central Park and Kraft Azalea Garden offer serene escapes and stunning backdrops for relaxation. Golf enthusiasts can enjoy the historic Winter Park Golf Course, a cherished 9-hole walkable course, or the Winter Park Pines Golf Club.

Top-Tier Education & Family-Friendly Appeal: Families are drawn to Winter Park for its highly-rated public and private schools within the Orange County Public School system. Winter Park High School is particularly renowned for its strong academic programs and extracurricular activities, attracting students with high aspirations. Rollins College, a nationally ranked liberal arts college, further enriches the community with its beautiful campus and cultural contributions. The city's safe neighborhoods and community-focused events make it an ideal place to raise children.

Winter Park, FL Real Estate Market Insights:

The Winter Park, FL real estate market remains highly competitive and sought-after. As of June 2025, the median sale price for homes in Winter Park is approximately $518,950, though average home values are around $468,479 with some recent market shifts. The market is currently considered a seller's market, indicating strong buyer demand. Homes typically sell within 26-63 days on the market, showcasing the area's enduring appeal.

You'll find a diverse portfolio of Winter Park homes for sale, including:

Luxury Homes in Winter Park: Exquisite estates, sprawling waterfront properties, and custom-built residences.
Historic Homes: Beautifully preserved homes offering unique architectural character.
Condos and Townhouses: Upscale, low-maintenance options for urban living.
Single-Family Homes: From charming bungalows to modern family residences.
Waterfront Homes Winter Park: Properties with direct access or stunning views of the Chain of Lakes.

Coveted neighborhoods such as Dixie Terrace, Comstock Park, Lake Knowles Terrace, Windsong, and areas surrounding Park Avenue offer distinct atmospheres and highly desirable residences.

Your Winter Park Real Estate Specialist:

As your dedicated Winter Park real estate agent, I possess an in-depth understanding of this unique and exclusive market. My services are tailored to your needs, whether you're looking to:

Buy a Home in Winter Park: Leverage my expertise to find your dream property, from elegant condos to grand estates.
Sell Your Winter Park Property: Benefit from strategic marketing and expert negotiation to achieve the best possible price.
Explore Winter Park Real Estate Market Trends: Get comprehensive insights into property values, inventory, and investment opportunities.
Discover New Construction Homes in Winter Park: Find the latest developments and modern architectural designs.

Experience the unparalleled lifestyle that awaits you in Winter Park, Florida. Contact me today to begin your journey to calling this prestigious community home.

Sean Ferguson Berkshire Hathaway Home Services Results Realty www.SeanSellsFlorida.com [email protected] 407-256-7698

Overview for Winter Park, FL

79,678 people live in Winter Park, where the median age is 38 and the average individual income is $53,579.199. Data provided by the U.S. Census Bureau.

79,678

Total Population

38 years

Median Age

High

Population Density Population Density
This is the number of people per square mile in a neighborhood.

$53,579.199

Average individual Income

Around Winter Park, FL

There's plenty to do around Winter Park, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.

17

Car-Dependent

Walking Score

36

Somewhat Bikeable

Bike Score

28

Some Transit

Transit Score

Points of Interest

Explore popular things to do in the area, including Bob's Nutrition Plus, The Vintage Vault, and Milano's.

Name	Category	Distance	Reviews	Ratings by Yelp
Visit the Bob's Nutrition Plus page on Yelp Search 1555 State Rd 436 on Google Maps	Dining	1.27 miles	7 reviews	5/5 stars
Visit the The Vintage Vault page on Yelp Search 323 S Park Ave on Google Maps	Dining	1.91 miles	5 reviews	5/5 stars
Visit the Milano's page on Yelp Search 3211 E Colonial Dr on Google Maps	Shopping	3.71 miles	21 reviews	5/5 stars
Visit the That Shoe Store & More page on Yelp Search 6013 E Colonial Dr on Google Maps	Shopping	3.25 miles	5 reviews	5/5 stars
Visit the VinceFit page on Yelp Search 1376 Lake Baldwin Ln on Google Maps	Active	2.83 miles	5 reviews	5/5 stars
Visit the Centering Pilates and Fitness page on Yelp Search 540 E Horatio Ave on Google Maps	Active	2.79 miles	8 reviews	5/5 stars
Visit the Bella Mia Hair Salon page on Yelp Search 670 N Orlando Ave on Google Maps	Beauty	3.05 miles	9 reviews	5/5 stars
Visit the Cut It Out Private Studio page on Yelp Search 4270 Aloma Ave on Google Maps	Beauty	2.62 miles	7 reviews	5/5 stars
Visit the Shop 25eighh page on Yelp Search 955 S Orlando Ave on Google Maps	Beauty	2.88 miles	5 reviews	5/5 stars
Visit the Lucia Benjamin page on Yelp Search 362 S Pennsylvania Ave on Google Maps	Beauty	2.23 miles	6 reviews	5/5 stars
Visit the Simply You By Stef page on Yelp Search 515 N Park Ave on Google Maps	Beauty	1.81 miles	7 reviews	5/5 stars
Visit the Old Florida Electric page on Yelp Search 1223 N Orange Ave on Google Maps	Beauty	4.33 miles	9 reviews	5/5 stars
Visit the Colovaria Hair Salon page on Yelp Search 4910 E Colonial Dr on Google Maps	Beauty	3.69 miles	5 reviews	5/5 stars

Demographics and Employment Data for Winter Park, FL

Population Households Employment

Winter Park has 33,976 households, with an average household size of 4.47. Data provided by the U.S. Census Bureau. Here’s what the people living in Winter Park do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 79,678 people call Winter Park home. The population density is 4,049.81 and the largest age group is Data provided by the U.S. Census Bureau.

79,678

Total Population

High

Population Density Population Density This is the number of people per square mile in a neighborhood.

37.97285825447426

Median Age

49.61 / 50.39%

Men vs Women

Population by Age Group

0-9:

0-9 Years

10-17:

10-17 Years

18-24:

18-24 Years

25-64:

25-64 Years

65-74:

65-74 Years

75+:

75+ Years

Education Level

Less Than 9th Grade
High School Degree
Associate Degree
Bachelor Degree
Graduate Degree

33,976

Total Households

4.47

Average Household Size

$53,579.199

Average individual Income

Households with Children

With Children:

Without Children:

Marital Status

Married

Single

Divorced

Separated

Blue vs White Collar Workers

Blue Collar:

White Collar:

Commute Time

0 to 14 Minutes

15 to 29 Minutes

30 to 59 Minutes

60+ Minutes

Schools in Winter Park, FL

All ()

Primary Schools ()

Middle Schools ()

High Schools ()

Mixed Schools ()

The following schools are within or nearby Winter Park. The rating and statistics can serve as a starting point to make baseline comparisons on the right schools for your family. Data provided by the U.S. Census Bureau.

Type

Name

Explore Neighborhoods

Orlando
Celebration
Kissimmee
Clermont
Winter Garden
Davenport
Winter Park
Maitland
Altamonte Springs
Sanford

Explore Orlando

Discover Metro Orlando, Florida, a vibrant and rapidly growing region renowned for its world-class attractions, diverse communities, and endless lifestyle opportunities. Beyond the magic of Disney and Universal, this area boasts a thriving cultural scene, beautiful lakes, and a strong job market. Metro Orlando real estate offers a wide range of homes for sale, from bustling downtown condos to family-friendly suburban houses and lucrative investment properties. As of June 2025, the median home price in Orlando is around $395,402, with various neighborhoods providing unique living experiences, making it an ideal place to buy a home in Central Florida.
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Explore Celebration

Step into the enchanting community of Celebration, Florida, a master-planned town originally envisioned by Disney, offering a storybook lifestyle just moments from Walt Disney World Resort. This charming area blends nostalgic "small-town America" aesthetics with modern amenities, featuring walkable streets, boutique shops, and a vibrant community calendar. Residents enjoy abundant parks, miles of trails, community pools, and access to highly-rated schools, making it an ideal choice for families. The Celebration real estate market provides diverse housing options, from charming single-family homes to elegant townhouses and luxurious estates, with a median sold price around $625,000 as of June 2025. Whether you're seeking a unique home or a smart investment, Celebration offers an unparalleled quality of life in Central Florida.
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Explore Kissimmee

Discover Kissimmee, Florida, the vibrant heart of Osceola County, famous for its proximity to world-renowned theme parks like Walt Disney World and its unique blend of tourist attractions and local community charm. Ideal for vacation home investors, first-time homebuyers, and families, Kissimmee offers diverse homes for sale, from family residences to short-term rental properties. As of July 2025, the Kissimmee real estate market shows a median sold price around $363,337 - $395,000, offering relatively affordable options with diverse communities and amenities, making it a prime location for Central Florida living.
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Explore Clermont

Discover Clermont, Florida, the "Choice of Champions," a vibrant city west of Orlando celebrated for its rolling hills, pristine lakes, and active outdoor lifestyle. Ideal for those seeking homes for sale in Clermont, FL, this area offers abundant opportunities for biking, running, and water sports on the Chain of Lakes. The Clermont real estate market provides diverse options, from charming single-family homes and new construction to a variety of popular 55+ communities. With a median home sale price around $447,249 as of June 2025, Clermont blends natural beauty with a strong, family-friendly community, making it a truly desirable Central Florida destination.
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Explore Winter Garden
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Explore Davenport

Discover Davenport, Florida, a rapidly growing city in Polk County, ideally situated near Orlando's world-famous theme parks, making it a prime location for both residents and investors. Known for its appealing blend of affordability, a relaxed atmosphere, and convenient access to attractions, Davenport offers a diverse range of homes for sale, particularly popular for vacation homes and short-term rentals in resort-style communities like ChampionsGate and Solterra. The Davenport real estate market is currently a buyer's market, with a median home sale price around $349,933 - $399,900 as of June-July 2025, providing excellent opportunities for those seeking value in Central Florida.
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Explore Winter Park

Discover Winter Park, Florida, a highly sought-after, affluent community just north of Orlando, known for its elegant charm and sophisticated lifestyle. Tree-lined brick streets, vibrant Park Avenue with upscale boutiques and gourmet dining, world-class museums, and beautiful chain of lakes define this picturesque city. Winter Park real estate offers a diverse selection, from historic homes and luxury estates to charming bungalows, with a median sale price around $460,000 - $518,950 as of June 2025. Experience a rich cultural scene, top-rated schools, and abundant parks in this desirable Central Florida gem.
Read More
Explore Maitland

Discover Maitland, Florida, a charming and established city just north of Orlando, offering an ideal blend of residential tranquility and urban convenience. Known for its beautiful lakes, historic sites like the Maitland Art Center and Lake Lily Park, and a thriving cultural scene, it provides a peaceful yet vibrant lifestyle. Maitland boasts highly-rated schools and a family-friendly atmosphere, making it a desirable Central Florida location. The Maitland real estate market is currently a neutral market, with a median sold price around $489,000 as of June 2025, featuring diverse homes for sale from historic residences to modern townhouses and beautiful lakefront properties.
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Explore Altamonte Springs

Discover Altamonte Springs, Florida, a thriving Seminole County city just north of Orlando, offering an excellent blend of suburban comfort and modern amenities. Known for Uptown Altamonte and Cranes Roost Park with its vibrant events, the area provides abundant shopping, diverse dining, and easy access to major highways and top-rated Seminole County schools. The Altamonte Springs real estate market currently shows a median home sale price around $317,500 as of June 2025, offering diverse homes for sale, including single-family residences, condos, and townhouses, making it an attractive option for convenient Central Florida living.
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Explore Sanford

Discover Sanford, Florida, a charming city in Seminole County offering a rich blend of history, waterfront beauty, and modern conveniences. Its Historic Downtown Sanford boasts brick-lined streets, unique shops, diverse restaurants, and craft breweries, all along the picturesque Sanford RiverWalk on Lake Monroe. With a strong community feel, access to top-rated Seminole County schools, and the Orlando Sanford International Airport (SFB), Sanford is ideal for families and commuters. The Sanford real estate market features a range of homes for sale, including historic properties and new constructions, with a median sale price around $370,000 - $399,500 as of June 2025.
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