The Housing Market in Winter Garden Today

Couple eating pizza on floor of new apartment in Winter Garden surrounded by moving boxes
For many young couples, apartments offer an affordable first home in Winter Garden as they begin building a life together.

The housing market in Winter Garden, Florida has seen significant changes in recent years. Inventory has tightened as more people flock to this charming Orlando suburb known for its historic downtown, scenic bike trail, and top-rated schools. New housing developments are rising to meet the growing demand, particularly in the downtown core and newer planned communities on the city’s edges.

Despite the influx of new residents, Winter Garden remains relatively affordable compared to many parts of the Orlando metro. However, the cost of living in an apartment vs house in Winter Garden can vary considerably depending on factors like location, size, and amenities. Understanding these differences is key for anyone considering a move to the area.

Renting in Winter Garden: What’s Typical?

As of 2025, the average rent for a 1-bedroom apartment in Winter Garden is around $1,450 per month. For a 2-bedroom unit, renters can expect to pay closer to $1,800 on average. These figures represent a modest 3-5% increase from 2024 levels.

Rent prices tend to be highest in the downtown district and newer complexes near the Winter Garden Village shopping center. More affordable options can often be found on the north and east sides of the city. Popular with young professionals, apartments in Winter Garden typically include amenities like pools, fitness centers, and in-unit laundry.

While exact vacancy rates fluctuate, Winter Garden has maintained a relatively balanced rental market in recent years. Most properties are able to fill vacancies within 4-6 weeks at current market rates. This stability is largely attributed to the city’s strong job market, highly-rated schools, and appealing quality of life.

Owning a Home in Winter Garden

For those looking to purchase a home, the median sale price in Winter Garden currently stands at $415,000 – up 6% from the previous year but still below the metro Orlando average. With a 10% down payment and 5.5% interest rate, the typical monthly mortgage comes to around $2,450 including taxes and insurance.

In addition to the mortgage, Winter Garden homeowners can expect to pay around $3,500 per year in property taxes. Most newer subdivisions also have HOA dues ranging from $200 to $500 annually. Maintenance, repairs, and utilities add further to the total cost of ownership.

While certainly pricier than renting on a monthly basis, owning a home in Winter Garden can be a smart long-term investment. The city’s population and property values have risen steadily over the past decade, a trend that most analysts expect to continue in the coming years.

Renters vs. Homeowners: Who Lives Where?

Currently, about 65% of households in Winter Garden own their homes, while 35% rent. This homeownership rate is slightly higher than the national average but on par with suburban areas.

Renters in Winter Garden tend to be younger, with many in their 20s and 30s. They are often single or coupled without children and work in fields like healthcare, education, retail, and hospitality. Homeowners, by contrast, skew older and are more likely to be married with kids. They tend to have higher incomes and longer-term ties to the area.

Despite these trends, Winter Garden is home to a diverse mix of residents across the housing spectrum. Young families are increasingly purchasing starter homes in the area, while some empty-nesters are opting to downsize into low-maintenance apartments. Still, financial barriers like down payments and credit scores continue to shape who can afford to own in today’s market.

Table: Typical Monthly Housing Costs in Winter Garden

Here’s what housing costs might look like each month in Winter Garden:

Expense Apartment (1BR) House (3BR)
Rent/Mortgage $1,450 $2,450
Property Tax $0 $290
Renters/Homeowners Insurance $15 $120
Utilities $120 $280
HOA Dues $0 $35
Total $1,585 $3,175

Estimates reflect mid-range properties and average usage.

What’s Driving Costs Up or Down?

Several factors are influencing housing costs in Winter Garden. On the demand side, the city’s strong job market, highly-rated schools, and appealing amenities continue to attract new residents. This is putting upward pressure on both rents and home prices.

In terms of supply, Winter Garden has seen a flurry of new apartment and housing developments in recent years. While this new construction is helping to meet some of the demand, it is also concentrated at the mid-to-high end of the market. Zoning changes have allowed for denser development downtown, but most new single-family homes are still being built on the city’s outskirts.

Looking ahead, Winter Garden’s housing costs will likely continue to rise but at a more moderate pace than in recent years. Local leaders are exploring policies to encourage more affordable housing options, but demand is expected to remain strong given the area’s economic vitality and quality of life. Prospective residents will need to weigh their budgets and priorities carefully to determine the right housing choice.

FAQs About Housing in Winter Garden

  • Is Winter Garden affordable to live in? While housing costs in Winter Garden have risen in recent years, the city remains relatively affordable compared to many parts of the Orlando area. Expenses like utilities and property taxes are also lower than in some neighboring communities.
  • Why are housing prices changing? Winter Garden’s housing market is being shaped by a combination of strong demand, limited supply, and changing development patterns. The city’s growing population and healthy economy are putting upward pressure on rents and home prices.
  • How does Winter Garden compare to nearby cities? Housing costs in Winter Garden are generally lower than in central Orlando but higher than in some outlying areas. The city offers a balance of suburban amenities and relative affordability that appeals to many renters and buyers.

Making Smart Housing Decisions in Winter Garden

For anyone considering a move to Winter Garden, it’s important to weigh the full cost of housing options. As this analysis shows, the choice between renting and owning can mean a difference of $1,000 or more per month, even for similarly-sized properties.

Renters may have lower upfront costs and more flexibility, but they won’t build equity over time. Homeowners face bigger monthly expenses but have the potential for long-term financial gains. Ultimately, the right choice depends on each household’s unique circumstances and goals.

No matter one’s housing situation, living in Winter Garden is more affordable with smart budgeting and planning. For more tips and tools, check out our guides on Monthly Budget Examples for Winter Garden Residents and Cost of Living in Winter Garden (2025 Guide).