Winfield

Winfield is a community of single family homes in Maitland, Florida, with a range of options priced between $162,000 and $555,000. The smallest Winfield home in the community is a three bedroom two bathroom residence that is 1,852 square feet (1,307SF Under Air living space), and the largest of the Winfield homes has five beds and two baths and is a 2,863 square foot (2,365SF 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 $50 to $250. 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 January 2026) reflects seven homes changing hands, with an average asking price of $464,257 and an average selling price of $441,143. This represents a healthy list-to-sell price ratio of 95% and $178 per square foot. During this period, Winfield homes for sale have taken an average of 58 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

SOLD 03/07/24

$430,000

MLS#MFRO6171534

2178 Fennell St
Maitland, FL 32751

3

2

2

2,120 SqFt

Pool

0.12 Acres

SOLD 07/19/17

$235,000

MLS#MFRO5517973

7907 Birman St
Maitland, FL 32751

3

2

2

1,873 SqFt

Pool

0.13 Acres

SOLD 03/31/23

$402,500

$450,000

MLS#MFRO6053162

2137 Fennell St
Maitland, FL 32751

4

2

2

2,200 SqFt

Pool

0.12 Acres

SOLD 12/22/14

$200,000

$209,000

MLS#MFRO5319171

2161 Fennell St
Maitland, FL 32751

4

2

2

2,324 SqFt

0.13 Acres

SOLD 08/05/24

$465,000

MLS#MFRNS1081320

7919 Birman St
Maitland, FL 32751

3

2

2

2,565 SqFt

0.13 Acres

SOLD 01/07/26

$395,000

MLS#MFRO6316462

2155 Fennell St
Maitland, FL 32751

3

2

2

2,358 SqFt

Pool

0.16 Acres

SOLD 06/01/22

$425,000

MLS#MFRO6019390

2187 Fennell St
Maitland, FL 32751

3

2

1,740 SqFt

0.14 Acres

SOLD 09/05/25

$425,000

MLS#MFRO6327981

2132 Tortoise Shell Dr
Maitland, FL 32751

4

2

2

2,201 SqFt

0.12 Acres

SOLD 08/26/22

$439,000

$449,900

MLS#MFRO6040546

7903 Chartreux Ln
Maitland, FL 32751

4

2

2

2,040 SqFt

Pool

0.2 Acres

SOLD 02/23/15

$162,000

$169,000

MLS#MFRO5334096

1614 Bobtail Dr
Maitland, FL 32751

3

2

2

1,897 SqFt

0.13 Acres

SOLD 08/15/14

$179,000

$189,900

MLS#MFRO5192453

2163 Tortoise Shell Dr
Maitland, FL 32751

3

2

2

1,986 SqFt

0.12 Acres

SOLD 11/24/14

$192,500

$195,000

MLS#MFRO5316647

2157 Tortoise Shell Dr
Maitland, FL 32751

3

2

2

2,160 SqFt

0.12 Acres

SOLD 02/26/16

$220,000

MLS#MFRO5379754

2157 Tortoise Shell Dr
Maitland, FL 32751

3

2

2

2,160 SqFt

0.12 Acres

SOLD 03/08/22

$350,000

$369,900

MLS#MFRO5993950

1632 Bobtail Dr
Maitland, FL 32751

4

2

2

1,822 SqFt

0.13 Acres

SOLD 05/30/24

$390,000

MLS#MFRO6197485

7954 Birman St
Maitland, FL 32751

3

2

2

2,188 SqFt

0.12 Acres

SOLD 04/12/18

$298,850

MLS#MFRO5567008

7921 Chartreux Ln
Maitland, FL 32751

3

3

2

2,593 SqFt

Pool

0.12 Acres

SOLD 06/23/25

$480,000

MLS#MFRS5124441

2110 Korat Ln
Maitland, FL 32751

4

3

2

2,863 SqFt

0.12 Acres

SOLD 02/23/17

$230,000

MLS#MFRO5478209

2134 Korat Ln
Maitland, FL 32751

3

2

2

2,160 SqFt

0.12 Acres

SOLD 12/09/22

$447,000

MLS#MFRO6069500

8003 Birman St
Maitland, FL 32751

4

3

2

2,282 SqFt

0.13 Acres

SOLD 10/25/12

$179,900

MLS#MFRO5118932

1644 Bobtail Dr
Maitland, FL 32751

3

2

2

2,167 SqFt

Pool

0.13 Acres

SOLD 07/12/17

$265,000

MLS#MFRO5514120

1644 Bobtail Dr
Maitland, FL 32751

3

2

2

2,167 SqFt

Pool

0.13 Acres

SOLD 04/15/22

$400,000

MLS#MFRO6007104

2034 Bobtail Dr
Maitland, FL 32751

3

2

2

1,307 SqFt

0.12 Acres

SOLD 01/23/23

$440,000

$445,000

MLS#MFRO6071613

8010 Birman St
Maitland, FL 32751

3

2

2

2,288 SqFt

Pool

0.15 Acres

SOLD 12/28/12

$175,000

MLS#MFRO5128227

2016 Bobtail Dr
Maitland, FL 32751

3

3

2

2,434 SqFt

0.12 Acres

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We do not have any properties available for sale in Winfield.

0 Active Listings in Winfield