Honest Pros and Cons of Living in Winter Park

Honest Pros and Cons of Living in Winter Park


Winter Park is a captivating suburb that offers a vibrant lifestyle for its residents. The charm of this place is nothing short of magnetic. With a deep history, lush natural surroundings, and a strong sense of community, living here is truly an experience to cherish. Ranked among Florida’s best suburbs for young professionals, Winter Park has a timeless appeal with the modern amenities you’d expect from a larger city.

Every place has unique strengths and challenges, and Winter Park is no different. Read on to learn what sets Winter Park apart from the competition and what challenges residents tackle.

Pros of living in Winter Park

With so much working in its favor, it’s easy to see why so many call Winter Park home. Here are some of the suburb’s highlights.

Close to nature and outdoor activities

Nearly all residents would agree Winter Park is stunningly beautiful, especially for a community so close to downtown Orlando. Anywhere you go, you’ll find beautiful lakes — Lake Baldwin, Lake Killarney, Lake Maitland, and Lake Virginia are among the most prominent. There are also a few excellent golf courses within Winter Park (especially Winter Park Pines Golf Club) and about 50 golf courses within 20 miles of the suburb.

Vibrant and active community

Newcomers to Winter Park will be glad to learn how many fun activities and events occur throughout the year. You can go paddleboarding on the lakes, browse the local farmers market, shop boutiques at Winter Park Village, and take a peaceful walk at Mead Botanical Garden. Many areas are dog-friendly, making Winter Park an ideal community for you and your canine friends.

Access to quality education

The Winter Park community is served by Orange County Public Schools, a district renowned for its commitment to educational excellence. Parents will be pleased to find a diverse selection of high-quality public and private schools offering programs to meet various student needs and interests. A few local options include St. Margaret Mary Catholic School, Glenridge Middle School, and Winter Park High School.

The rich cultural and artistic scene

Winter Park is also the site of several art museums and sculpture gardens. One must-see is The Charles Hosmer Morse Museum of American Art, which houses priceless art from the late 19th century and hosts celebrations like Christmas in the Park. Many historic buildings from the late 19th century remain, including those at Hannibal Square, a cozy street with a museum and cafes near the town center.

Wide range of restaurants and cuisines

There are many great Winter Park restaurants to enjoy. You can relish Italian cuisine at Prato, order farm-to-table dishes at Boca, and sip the perfect wine at The Parkview. There are several local bars and gastropubs ideal for grabbing drinks and watching sports. Area restaurants range from casual to upscale in formality.

Pleasant weather

Winter Park has a humid subtropical climate marked by hot and humid summers and mild winters. Average high temperatures peak in the low 90s, and rarely do average low temperatures drop below the 50s. Winter Park gets more rain than the national average, no snowfall, and enjoys 238 sunny days yearly.

Cons of living in Winter Park

There are only a few reasons someone might think twice about moving to Winter Park. Let’s review a few cons and investigate their potential impact on your lifestyle.

Traffic during peak hours

Traffic during peak hours in Winter Park can be heavy, especially on major roads like U.S. Highway 17. The heaviest traffic is typically seen in the morning and evening rush hours, from 7 a.m. to 9 a.m. and 4 p.m. to 6 p.m. If possible, make your commute outside peak hours (and ask your real estate agent for shortcuts).

Relatively high cost of living

In considering a move to Winter Park, it's essential to understand your expenses. This beautiful suburban city offers a quality of life that aligns with its cost of living. The main expense is housing, which costs 52% more than the national average. Total expenses put Winter Park in the top 10% of the most expensive cities worldwide. Consult your financial planner for more details.

Limited nightlife options

A relatively quiet suburb, Winter Park only offers a few venues open late. Most local businesses cater to families, and fewer bars and clubs exist than in more adult-oriented cities. Instead, many Winter Park revelers take their party to Orlando, which has plenty of nightlife options.

Some areas aren’t very walkable

Winter Park has an average walk score of 44 out of 100. As a prospective homebuyer, you can ask your agent to focus on the most walkable streets in Winter Park, the ones closest to Park Ave. and Central Park. Outside that swath, Winter Park is relatively spread out, making it time-consuming to get around on foot. With the aforementioned traffic dynamic, you may want to plan your commutes and errands thoughtfully, especially during the summer, when it can get hot enough to melt some groceries on your way home. Despite these challenges, however, a number of local businesses offer delivery services, allowing you to circumvent the above issues entirely.

Housing can be expensive

As mentioned above, Winter Park houses cost 52% more than the national average. These homes range from midcentury Florida ranches to sprawling waterfront estates. Luxury buyers tend to focus on properties in two areas: those next to Winter Park’s chain of lakes and those within walking distance of the shops and restaurants of Park Avenue. As of August 2023, Jamie Mckie had access to over 150 properties throughout Winter Park, so the odds are that you’ll find a suitable house.

About Jamie Mckie

Jamie Mckie is an Orlando-based REALTOR® with a staunch commitment to meeting her clients' needs and ensuring their happiness. If you want to buy or sell a home or have questions about the real estate market and homes for sale in Winter Park , contact Jamie Mckie today.

*Header photo courtesy of Visit Orlando


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Jamie's passion to serve people enables her to show clients properties within their budgets. She also acknowledges that real agency requires respect for diversity.

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