Winfield

Winfield is a community of single family homes in Maitland, Florida, with a range of options priced between $395,000 and $555,000. There are currently a total of 5 homes for sale in Winfield. The smallest Winfield home presently available is a three bedroom two bathroom residence that is 1,800 square feet, and the largest of the Winfield homes currently on the market has four beds and three baths and is a 2,804 square foot (2,359SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Winfield range from $100 to $204. Please check the individual listing pages for the exact homeowners association fees for a particular Winfield home.

The Winfield HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Winfield - Orlando Executive (ORL), which is seven miles away; Orlando Sanford International (SFB), which is fifteen miles away; Orlando International (MCO), which is fifteen miles away, and Kissimmee Gateway (ISM), which is twenty four miles away from Winfield.

Winfield real estate activity on the Maitland MLS during the past year (as of September 2025) reflects six homes changing hands, with an average asking price of $461,500 and an average selling price of $461,833. This represents a healthy list-to-sell price ratio of 100% and $186 per square foot. During this period, Winfield homes for sale have taken an average of just 25 days to sell.

In addition, there are numerous other communities in Maitland to choose from, or you may browse all available Maitland Real Estate, including some new construction opportunities. Homes for sale in Winfield are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Winfield hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

Winfield Homes For Sale

Under Contract

$555,000

$565,000

MLS#MFRO6304886

1758 Bobtail Dr
Maitland, FL 32751

4

3

2

2,768 SqFt

Pool

0.12 Acres

127 Days

Reduced

$514,900

$524,900

MLS#MFRO6280804

2133 Korat Ln
Maitland, FL 32751

4

3

2

2,804 SqFt

Pool

0.12 Acres

202 Days

Under Contract

$425,000

MLS#MFRO6327981

2132 Tortoise Shell Dr
Maitland, FL 32751

4

2

2

2,201 SqFt

0.12 Acres

50 Days

Reduced

$413,000

$415,000

MLS#MFRO6298600

2122 Korat Ln
Maitland, FL 32751

4

2

2

1,800 SqFt

0.12 Acres

147 Days

Under Contract

$395,000

MLS#MFRO6316462

2155 Fennell St
Maitland, FL 32751

3

2

2

2,358 SqFt

Pool

0.16 Acres

89 Days

5 Active Listings in Winfield