Winfield

Winfield is a community of single family homes in Maitland, Florida, with a range of options priced between $364,500 and $555,000. There are currently a total of 6 homes for sale in Winfield. The smallest Winfield home presently available is a three bedroom two bathroom residence that is 1,822 square feet (1,382SF Under Air living space), and the largest of the Winfield homes currently on the market has four beds and three baths and is a 2,954 square foot (2,344SF 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 $17 to $105. This fee includes grounds maintenance, and security. 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 International (MCO), which is fifteen miles away; Orlando Sanford International (SFB), 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 June 2026) reflects seven homes changing hands, with an average asking price of $467,814 and an average selling price of $444,486. This represents a healthy list-to-sell price ratio of 95% and $180 per square foot. During this period, Winfield homes for sale have taken an average of 46 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 BEX Realty agent, who would happily assist you further with all your Central Florida real estate needs.

Winfield Homes For Sale

Reduced

$519,999

$524,999

MLS#MFRG5110747

1776 Bobtail Dr
Maitland, FL 32751

4

3

2

2,954 SqFt

0.12 Acres

75 Days

$489,900

MLS#MFRS5151303

2155 Fennell St
Maitland, FL 32751

3

2

2

1,822 SqFt

Pool

0.16 Acres

17 Days

Under Contract

$420,000

$430,000

MLS#MFRO6406585

2154 Fennell St
Maitland, FL 32751

3

2

2

2,160 SqFt

0.17 Acres

40 Days

Reduced

$409,900

$429,900

MLS#MFRO6392895

2150 Tortoise Shell Dr
Maitland, FL 32751

4

2

2

1,887 SqFt

0.16 Acres

61 Days

Under Contract

$370,000

MLS#MFRO6408698

2040 Bobtail Dr
Maitland, FL 32751

3

2

2

1,852 SqFt

0.12 Acres

35 Days

Under Contract

$364,500

MLS#MFRO6401286

2134 Korat Ln
Maitland, FL 32751

3

2

2

2,160 SqFt

0.12 Acres

37 Days

6 Active Listings in Winfield