Courtlea Oaks

Courtlea Oaks is a community of single family homes in Winter Garden, Florida, with a range of options priced between $354,900 and $1,299,000. The smallest Courtlea Oaks home in the community is a three bedroom two bathroom residence that is 3,414 square feet (2,238SF Under Air living space), and the largest of the Courtlea Oaks homes has six beds and four baths and is a 6,063 square foot (4,392SF 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 Courtlea Oaks range from $400 to $800. Please check the individual listing pages for the exact homeowners association fees for a particular Courtlea Oaks home.

The Courtlea Oaks HOA rules do allow homeowners to have pets although there are certain breed restrictions. Dogs and cats are allowed.

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

Courtlea Oaks real estate activity on the Winter Garden MLS during the past year (as of January 2026) reflects five homes changing hands, with an average asking price of $824,400 and an average selling price of $811,200. This represents a healthy list-to-sell price ratio of 98% and $209 per square foot. During this period, Courtlea Oaks homes for sale have taken an average of 36 days to sell.

In addition, there are numerous other communities in Winter Garden to choose from, or you may browse all available Winter Garden Real Estate, including some new construction opportunities. Homes for sale in Courtlea Oaks are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Courtlea Oaks 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.

Courtlea Oaks Homes For Sale

SOLD 06/03/22

$927,000

MLS#MFRO6020684

209 Trail Bridge Ct
Winter Garden, FL 34787

5

4

3

6,063 SqFt

Pool

0.66 Acres

SOLD 09/17/25

$749,000

$875,000

MLS#MFRO6319154

205 Trail Bridge Ct
Winter Garden, FL 34787

3

3

2

3,606 SqFt

0.3 Acres

SOLD 06/13/13

$354,900

MLS#MFRG4692723

319 Courtlea Oaks Blvd
Winter Garden, FL 34787

4

3

3

3,957 SqFt

0.33 Acres

SOLD 05/25/18

$485,000

MLS#MFRO5569061

437 Courtlea Oaks Blvd
Winter Garden, FL 34787

3

4

2

3,947 SqFt

0.34 Acres

SOLD 07/12/23

$999,999

MLS#MFRO6118356

421 Courtlea Oaks Blvd
Winter Garden, FL 34787

5

4

3

5,220 SqFt

Pool

0.45 Acres

SOLD 11/22/24

$1,299,000

$1,349,000

MLS#MFRO6236924

412 Courtlea Oaks Blvd
Winter Garden, FL 34787

4

4

3

4,700 SqFt

Pool

0.33 Acres

SOLD 11/25/25

$675,000

MLS#MFRG5102443

418 Courtlea Oaks Blvd
Winter Garden, FL 34787

4

3

2

3,414 SqFt

0.33 Acres

SOLD 08/06/24

$850,000

$925,000

MLS#MFRO6189593

428 Courtlea Oaks Blvd
Winter Garden, FL 34787

4

5

4

5,067 SqFt

Pool

0.33 Acres

SOLD 11/16/12

$365,000

MLS#MFRO5112259

424 Courtlea Oaks Blvd
Winter Garden, FL 34787

6

4

4

4,934 SqFt

Pool

0.33 Acres

SOLD 08/27/15

$448,500

MLS#MFRW7608568

409 Courtlea Creek Dr
Winter Garden, FL 34787

5

3

3

4,170 SqFt

0.33 Acres

SOLD 10/08/25

$950,000

MLS#MFRO6323876

403 Courtlea Creek Dr
Winter Garden, FL 34787

5

3

2

4,376 SqFt

Pool

0.33 Acres

SOLD 04/08/22

$600,000

MLS#MFRJ945091

404 Courtlea Creek Dr
Winter Garden, FL 34787

4

3

2

0.33 Acres

SOLD 11/23/21

$649,900

MLS#MFRO5980376

320 Forest Haven Dr
Winter Garden, FL 34787

4

3

2

3,996 SqFt

Pool

0.33 Acres

SOLD 08/07/17

$535,000

$549,000

MLS#MFRO5512335

326 Forest Haven Dr
Winter Garden, FL 34787

4

5

3

4,916 SqFt

Pool

0.33 Acres

SOLD 08/31/23

$879,990

$939,990

MLS#MFRO6107440

450 Valley View Dr
Winter Garden, FL 34787

4

3

2

3,750 SqFt

Pool

0.35 Acres

SOLD 01/31/22

$685,500

MLS#MFRO5991919

442 Valley View Dr
Winter Garden, FL 34787

3

2

2

2,462 SqFt

Pool

0.33 Acres

SOLD 04/16/18

$489,900

MLS#MFRO5567483

436 Valley View Dr
Winter Garden, FL 34787

4

4

4,282 SqFt

0.33 Acres

SOLD 07/03/25

$699,000

MLS#MFRO6313426

432 Valley View Dr
Winter Garden, FL 34787

3

2

2

3,684 SqFt

0.33 Acres

SOLD 10/04/24

$1 Million

$1,200,000

MLS#MFRO6207608

436 Valley View Dr
Winter Garden, FL 34787

3

4

3

4,282 SqFt

0.33 Acres

SOLD 11/24/25

$1,049,000

$1,075,000

MLS#MFRO6343687

436 Valley View Dr
Winter Garden, FL 34787

3

4

3

4,282 SqFt

0.33 Acres

SOLD 08/14/15

$365,000

MLS#MFRO5360329

456 Spanish Wells Ct
Winter Garden, FL 34787

4

3

2

3,539 SqFt

Pool

0.37 Acres

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

0 Active Listings in Courtlea Oaks