Homes For Sale in Winter Park FL


Winter Park Florida - Things to Do, Attractions &Homes For Sale 

Homes for sale in Winter Park FL-Nestled just north of Orlando lies Winter Park Florida, a charming city that offers a delightful mix of history, culture and natural beauty. Consider the following houses for sale- $0 to $500,000 , $500,000 to $1M , $1M To Highest Price , Condos For Sale , Townhomes For Sale , Lakefront Homes

From the bustling downtown hub of Park Avenue to the prestigious Rollins College and the tranquil oasis of Mead Botanical Garden.

Winter Park Florida has something for everyone. In this blog post, we’ll take you on a journey through Winter Park Florida’s most notable attractions, real estate market, annual events, accommodations and transportation options. So buckle up and get ready to explore this captivating Floridian gem!

Short Summary

  • Explore Winter Park’s charming atmosphere, vibrant downtown hub on Park Avenue and prestigious liberal arts college Rollins College.

  • Enjoy the natural oasis of Mead Botanical Garden or take advantage of luxury living on the Chain of Lakes with sought-after real estate options.

  • Attend annual events, festivals and cultural institutions such as Hannibal Square Heritage Center or The Alfond Inn for a luxurious stay in Winter Park while taking advantage of its comprehensive transportation network.

Discovering Winter Park's Charm

Winter Park was established in 1881 and quickly gained a reputation as a popular destination for its attractions, dining, and shopping experiences. The city’s well-planned streets and buildings, which are required to meet stylistic and architectural standards, contribute to its quaint ambiance. Despite the influx of tourists, particularly during the winter months and holidays, Winter Park maintains its charm and allure making it an attractive location for businesses and visitors alike. Contact us to tour any of the homes for sale in Winter Park FL below.

The city’s rich history dates back to its first human residents, migrant Muscogee people who intermingled with the Choctaw and other native individuals. The development of FL real estate in the area was significantly influenced by the arrival of the South Florida Railroad in 1880. Today, Winter Park is a thriving community that seamlessly blends history, culture and modern amenities all attracting a diverse array of visitors and businesses.

Park Avenue - A Vibrant Downtown Hub

Park Avenue, the heart of Winter Park, is a picturesque tree-lined, cobblestoned street boasting an array of acclaimed eateries, museums and some of the finest shopping opportunities in the Orlando area. Just a short distance away, you’ll find Lyman Avenue Winter Park, another charming area to explore. The street boasts an array of civic structures, retail outlets, art galleries, Rollins College, museums, a park, a train station, a golf course country club, a historic cemetery and a beach with a boat launch.

It truly is a remarkable place of beauty and history. Park Ave, as it’s also known, offers visitors and residents alike a vibrant downtown hub where they can enjoy a diverse range of attractions and entertainment options.

The area surrounding Park Avenue is a testament to Winter Park’s commitment to preserving its historical charm and aesthetic appeal. From the meticulously maintained gardens and parks to the beautifully restored historic buildings, Park Avenue invites visitors to stroll, shop, dine and experience the essence of Winter Park’s culture and history.

Whether you’re searching for one-of-a-kind gifts, indulging in gourmet cuisine, or simply soaking in the atmosphere, Park Avenue is a must-visit destination in Winter Park especially during a sale event.

Rollins College - A Prestigious Institution

Rollins College, a prestigious liberal arts college located in Winter Park is renowned for its small classes taught by esteemed faculty, various study abroad and internship opportunities and numerous ways to participate in student organizations and the local community.

The college has been ranked #1 in Regional Universities South by the 2022-2023 edition of Best Colleges, making it an attractive choice for students from around the world. Notable alumni of Rollins College include Fred Rogers, Elin Nordegren, and Anthony Perkins.

The beautiful campus of Rollins College is nestled within the picturesque surroundings of Winter Park, offering a tranquil and inspiring environment for students to learn and grow. With its stunning architecture, lush green spaces and state-of-the-art facilities, Rollins College is a testament to the city’s commitment to education and excellence.

A visit to the campus will not only provide a glimpse into the lives of the students, but also showcase the college’s significant impact on Winter Park’s culture and community.

Mead Botanical Garden - A Natural Oasis

Mead Botanical Garden is a 48-acre natural attraction located in Winter Park, providing a serene retreat for visitors to enjoy nature and wildlife. The garden has something for everyone. It boasts a variety of ecosystems, an amphitheater, butterfly garden, discovery barn and a recreation center. Open to the public without charge, the garden also welcomes leashed dogs, making it an ideal destination for a relaxing day with your furry friend.

As you stroll through the garden’s pathways, you’ll be captivated by the diverse flora and fauna that call the Mead Botanical Garden home. From the vibrant colors of the butterfly garden to the tranquil sounds of the various water features, the garden offers a peaceful escape from the hustle and bustle of city life.

Whether you’re looking to enjoy a quiet picnic, attend an outdoor event at the amphitheater, or simply immerse yourself in nature, the Mead Botanical Garden is a must-see attraction in Winter Park.

Winter Park Real Estate

The real estate market in Winter Park is thriving, with a diverse range of properties available to suit a variety of tastes and budgets. As of May 2023, the median listing home price in Winter Park FL was $689K, demonstrating an increase of 37.8% year-over-year.

The city’s real estate market offers a selection of luxury properties, such as homes on the Winter Park Chain of Lakes, as well as historic neighborhoods like Hannibal Square. Whether you’re looking for a waterfront mansion or a charming cottage in a historic district, Winter Park has something to offer every homebuyer.

Luxury Properties on the Winter Park Chain of Lakes

The Winter Park Chain of Lakes boasts a variety of luxury properties, such as high-end homes, mansions, and condos. These stunning properties are situated on the picturesque lakes of Lake Maitland, Lake Osceola and Lake Virginia offering unparalleled waterfront views and access to water activities. The chain of lakes is a highly sought-after location for those seeking the ultimate in luxury living in Winter Park.

Owning a luxury property on the Winter Park Chain of Lakes is not only an investment in prime real estate, but also a lifestyle choice. With direct access to the lakes residents can enjoy activities such as boating, fishing and water sports. All while taking in the breathtaking scenery and abundant wildlife. The Winter Park Chain of Lakes offers a unique opportunity to experience the best of Florida’s natural beauty while living in the heart of a vibrant and thriving community.

Hannibal Square Heritage Center - Preserving History and Culture

The Hannibal Square Heritage Center is a community center in Winter Park, Florida, operated by the Crealdé School of Art. Established in 2007, the center is devoted to safeguarding the history and culture of the African American community in Winter Park. The Hannibal Square Heritage Center offers a range of programs and exhibits that explore the history and culture of the African American community in Winter Park, including lectures, workshops, and art exhibitions.

As a vital cultural institution in Winter Park, the Hannibal Square Heritage Center plays a crucial role in preserving the city’s rich history and diverse heritage. A visit to the center offers a unique opportunity to learn about the African American community’s contributions to Winter Park’s development, as well as to engage with the local community through various events and educational programs, including the Hope Group initiative.

The Hannibal Square Heritage Center is a must-visit destination for anyone interested in the history and culture of Winter Park.

Annual Events and Festivals in Winter Park

Winter Park’s vibrant community calendar is filled with annual events and festivals that cater to a wide range of interests. Some of the city’s most popular events include the Winter Park Autumn Art Festival, Winter on the Avenue, and the Winter Park Sidewalk Art Festival.

In addition, the city hosts a festive 4th of July celebration in Central Park West Meadow, offering a fun-filled day for the entire family. These events showcase the city’s commitment to fostering a vibrant arts and culture scene and providing unique experiences for residents and visitors alike.

Bach Festival - A Celebration of Classical Music

The Bach Festival is an annual event held in Winter Park that pays tribute to the musical works of Johann Sebastian Bach. Organized by the Bach Festival Society of Winter Park since 1935. The festival features performances from esteemed musicians from various parts of the globe, including orchestras, choirs and soloists. The Bach Festival is a celebration of classical music offering a platform for world-class musicians to perform in an enchanting setting.

Attending the Bach Festival is a truly unforgettable experience, as the captivating sounds of classical music fill the air and transport listeners to a different era. The festival’s diverse lineup of performances ensures that there is something for everyone from seasoned classical music enthusiasts to those new to the genre. The Bach Festival is a testament to Winter Park’s commitment to the arts and a wonderful opportunity to immerse oneself in the world of classical music.

Winter Park Concours d'Elegance - A Display of Automotive Excellence

The Winter Park Concours d’Elegance is a highly respected classic automobile invitational held in Winter Park, celebrating the art of automotive design. The event showcases a stunning collection of classic and exotic cars from across the globe, with each vehicle carefully selected and judged by a panel of experts who assess them based on their design, condition and originality.

Attending the Winter Park Concours d’Elegance is a must for any car enthusiast, as it offers a rare opportunity to admire some of the world’s most beautiful and sought-after vehicles up close. The event’s elegant setting and focus on automotive excellence make it a truly unique experience, attracting car collectors, enthusiasts and admirers from far and wide.

The Winter Park Concours d’Elegance is yet another example of the diverse array of events and attractions that make Winter Park such a dynamic and engaging community.

Accommodations in Winter Park

Winter Park offers a variety of accommodations to suit the needs of every traveler, from luxurious hotels to charming bed-and-breakfasts. One notable example is The Alfond Inn, a luxury hotel owned by Rollins College that combines art and hospitality to provide guests with a unique experience.

No matter where you choose to stay in Winter Park, you’ll find yourself conveniently close to the city’s many attractions and events, ensuring that your visit is both comfortable and enjoyable.

The Alfond Inn - Luxury and Art in One Place

The Alfond Inn is a luxurious hotel in Winter Park that features 112 guest rooms, a variety of amenities (including a pool), and an extensive art collection. The hotel’s elegant design and attention to detail create a truly one-of-a-kind experience for guests who can immerse themselves in the world of art while enjoying the comforts of a luxury hotel. The Alfond Inn’s convenient location near Park Avenue also makes it an ideal choice for visitors looking to explore the vibrant heart of Winter Park.

In addition to its exquisite accommodations, the Alfond Inn offers a comprehensive selection of amenities, including a pool, fitness center and restaurant. Whether you’re relaxing by the pool, working out in the state-of-the-art fitness center, or indulging in gourmet cuisine at the on-site restaurant, The Alfond Inn ensures that your stay in Winter Park is truly unforgettable, making it a perfect home away from home or “house” for your vacation.

Combining art, luxury, and unparalleled service, the Alfond Inn is the perfect choice for discerning travelers seeking a unique and memorable experience in Winter Park.

Getting Around Winter Park

Getting around Winter Park is easy and convenient thanks to the city’s accessible transportation options. The Winter Park Station serves as a central hub for commuters and visitors, providing access to the SunRail commuter train and other transportation options.

Whether you’re exploring the city’s many attractions, attending a festival, or simply enjoying a leisurely stroll along Park Avenue, Winter Park’s transportation network ensures that you can navigate the city with ease. Homes for sale in Winter Park FL.

Winter Park Station - A Central Hub for Commuters

The Winter Park Station is a railway station situated in Winter Park Florida that functions as a stop on the SunRail commuter rail system and Amtrak. The station’s central location makes it an ideal transportation hub for visitors and residents alike, granting effortless access to the SunRail commuter train and other transportation options such as buses, taxis and car rentals.

By using the Winter Park Station as a starting point for your adventures in the city, you can easily explore the many attractions and neighborhoods that Winter Park has to offer. The convenient access to public transportation also makes it possible to venture beyond the city limits and discover the greater Orlando area including downtown Orlando.

Whether you’re a local resident or a visitor to Winter Park, the Winter Park Station provides a seamless transportation experience allowing you to make the most of your time in this charming city.


In conclusion, Winter Park is a captivating destination that offers a unique blend of history, culture, and natural beauty. From the bustling streets of Park Avenue to the tranquil oasis of Mead Botanical Garden, there is something for everyone in this charming Floridian city. With a thriving real estate market, diverse annual events and festivals, luxurious accommodations and accessible transportation options. Winter Park is an ideal destination for those seeking a truly unforgettable experience. So why wait? Plan your visit to Winter Park today and discover the magic that awaits you in this enchanting city.

Frequently Asked Questions

Is Winter Park Florida a wealthy area?

Winter Park Florida is an area with a higher cost of living than the national average. This is due to high housing and grocery prices, as well as higher-than-average taxes.

Therefore, it can be concluded that Winter Park is an area of relative wealth and expensive houses.

What is special about Winter Park Florida?

Winter Park offers an idyllic setting for a delightful day trip or a perfect place to call home with its charming old-world European atmosphere, quaint streets lined with bricked sidewalks and canopy of trees.

It is the perfect mix of peacefulness and sophistication.

Is Winter Park FL a nice area?

Winter Park is an attractive and safe city in Central Florida offering visitors and residents alike plenty of fun things to do. From its picturesque lakes, lush gardens and fine dining establishments to its prestigious Park Avenue shopping district and historic Rollins College, Winter Park is truly a delight.

Does Winter Park FL have a downtown?

Yes, Winter Park FL has a vibrant downtown area situated along Park Avenue, boasting numerous restaurants and local boutiques for visitors to explore.

The historic Rollins College is also located just off Park Avenue, providing Winter Park with an array of cultural activities.

What attractions can I expect to find on Park Avenue in Winter Park?

Visitors to Park Avenue in Winter Park can enjoy a wide range of attractions, from restaurants and galleries to museums and Rollins College. There is something for everyone to enjoy! Contact us to tour any of the homes for sale in Winter Park FL shown below.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 7/21/24 10:06 AM) |

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DBA Wendy Morris Realty
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BK 3146762
16797 Broadwater Avenue
Winter Garden, Florida 34787

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