Middleton Oaks

Middleton Oaks is a community of single family homes in Sanford, Florida, with a range of options priced between $94,000 and $818,815. The smallest Middleton Oaks home in the community is a three bedroom two bathroom residence that is 1,666 square feet (1,246SF Under Air living space), and the largest of the Middleton Oaks homes has four beds and two baths and is a 4,592 square foot (3,783SF Under Air) residence.

Property management fees in Seminole County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Middleton Oaks range from $110 to $200. This fee includes maintaining the community roads, and real estate taxes for common areas. Please check the individual listing pages for the exact homeowners association fees for a particular Middleton Oaks home.

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

There are four commercial airports that serve Middleton Oaks - Orlando Sanford International (SFB), which is three miles away; Orlando Executive (ORL), which is fourteen miles away; Orlando International (MCO), which is twenty two miles away, and New Smyrna Beach Municipal (EVB), which is twenty nine miles away from Middleton Oaks.

Middleton Oaks real estate activity on the Sanford MLS during the past year (as of January 2026) reflects four homes changing hands, with an average asking price of $367,223 and an average selling price of $357,500. This represents a healthy list-to-sell price ratio of 97% and $170 per square foot. During this period, Middleton Oaks homes for sale have taken an average of 60 days to sell.

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

Middleton Oaks Homes For Sale

SOLD 05/05/23

$345,000

MLS#MFRO6101361

945 Penfield Cv
Sanford, FL 32773

3

2

2

1,698 SqFt

0.26 Acres

SOLD 07/25/16

$190,000

MLS#MFRO5446802

933 Penfield Cv
Sanford, FL 32773

3

2

2

2,192 SqFt

Pool

0.21 Acres

SOLD 12/10/18

$234,500

MLS#MFRO5538704

953 Penfield Cv
Sanford, FL 32773

3

2

2

2,660 SqFt

Pool

0.22 Acres

SOLD 03/10/17

$219,000

MLS#MFRO5483932

928 Penfield Cv
Sanford, FL 32773

3

2

2

2,518 SqFt

0.29 Acres

SOLD 11/07/25

$349,000

MLS#MFRV4944559

956 Penfield Cv
Sanford, FL 32773

3

2

2

1,666 SqFt

0.22 Acres

SOLD 11/28/16

$199,999

MLS#MFRO5473376

961 Penfield Cv
Sanford, FL 32773

3

2

2

2,160 SqFt

0.28 Acres

SOLD 10/07/22

$376,000

$420,000

MLS#MFRO6028426

4318 Meeting Pl
Sanford, FL 32773

3

2

2

1,764 SqFt

Pool

0.23 Acres

SOLD 08/15/22

$379,900

MLS#MFRO6042853

961 Penfield Cv
Sanford, FL 32773

3

2

2

1,618 SqFt

0.28 Acres

SOLD 06/26/17

$209,900

MLS#MFRO5511493

4290 Meeting Pl
Sanford, FL 32773

3

2

2

2,160 SqFt

0.31 Acres

SOLD 01/19/12

$109,950

MLS#MFRO5071372

4290 Meeting Pl
Sanford, FL 32773

3

2

2

2,160 SqFt

0.31 Acres

SOLD 10/02/15

$149,000

MLS#MFRO5385495

4286 Meeting Pl
Sanford, FL 32773

3

2

2

1,700 SqFt

0.3 Acres

SOLD 10/05/21

$279,000

MLS#MFRO5964680

4286 Meeting Pl
Sanford, FL 32773

3

2

2

1,700 SqFt

0.3 Acres

SOLD 10/29/15

$189,000

MLS#MFRO5386141

4282 Meeting Pl
Sanford, FL 32773

4

2

2

2,465 SqFt

Pool

0.27 Acres

SOLD 11/13/14

$149,900

$154,900

MLS#MFRV4700732

4297 Meeting Pl
Sanford, FL 32773

3

2

2

1,700 SqFt

Pool

0.21 Acres

SOLD 09/29/23

$399,900

MLS#MFRO6140244

904 Old Mail Ln
Sanford, FL 32773

4

2

2

2,672 SqFt

Pool

0.25 Acres

SOLD 08/16/24

$419,900

MLS#MFRO6224030

904 Old Mail Ln
Sanford, FL 32773

4

2

2

2,672 SqFt

Pool

0.25 Acres

SOLD 10/06/25

$359,990

$399,900

MLS#MFRO6320235

4274 Meeting Pl
Sanford, FL 32773

3

2

2

2,242 SqFt

0.27 Acres

SOLD 10/17/24

$339,900

MLS#MFRG5086352

4277 Meeting Pl
Sanford, FL 32773

3

2

2

1,693 SqFt

0.23 Acres

SOLD 01/17/14

$119,900

$129,900

MLS#MFRO5172816

4270 Meeting Pl
Sanford, FL 32773

3

2

2

1,772 SqFt

0.24 Acres

SOLD 07/27/24

$389,900

$405,000

MLS#MFRO6208504

917 Old Mail Ln
Sanford, FL 32773

3

2

2

2,072 SqFt

0.31 Acres

SOLD 03/16/18

$199,900

MLS#MFRO5560772

920 Old Mail Ln
Sanford, FL 32773

3

3

2

1,904 SqFt

0.22 Acres

SOLD 01/19/16

$174,900

MLS#MFRO5398714

4265 Iron Gate Ct
Sanford, FL 32773

3

2

2

1,904 SqFt

Pool

0.31 Acres

SOLD 09/22/22

$414,900

$429,900

MLS#MFRO6053229

4262 Meeting Pl
Sanford, FL 32773

4

2

2

2,465 SqFt

0.24 Acres

SOLD 12/02/16

$154,990

MLS#MFRO5462097

4262 Iron Gate Ct
Sanford, FL 32773

4

2

2

2,072 SqFt

0.2 Acres

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We do not have any properties available for sale in Middleton Oaks.

0 Active Listings in Middleton Oaks