Sleepy Hill Oaks

Sleepy Hill Oaks is a community of single family homes in Lakeland, Florida, with a range of options priced between $98,000 and $399,900. The smallest Sleepy Hill Oaks home in the community is a three bedroom two bathroom residence that is 1,947 square feet (1,515SF Under Air living space), and the largest of the Sleepy Hill Oaks homes has four beds and two baths and is a 3,764 square foot (2,869SF Under Air) residence.

Property management fees in Polk County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Sleepy Hill Oaks range from $180 to $250. Please check the individual listing pages for the exact homeowners association fees for a particular Sleepy Hill Oaks home.

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

There are four commercial airports that serve Sleepy Hill Oaks - Lakeland Linder International (LAL), which is seven miles away; Tampa International (TPA), which is 33 miles away; Kissimmee Gateway (ISM), which is 38 miles away, and Orlando International (MCO), which is 49 miles away from Sleepy Hill Oaks.

Sleepy Hill Oaks real estate activity on the Lakeland MLS during the past year (as of October 2025) reflects five homes changing hands, with an average asking price of $264,920 and an average selling price of $263,940. This represents a healthy list-to-sell price ratio of 100% and $137 per square foot. During this period, Sleepy Hill Oaks homes for sale have taken an average of 122 days to sell.

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

Sleepy Hill Oaks Homes For Sale

SOLD 08/12/22

$208,000

MLS#MFRP4921496

3173 Pioneer Trails Loop
Lakeland, FL 33810

4

3

0.25 Acres

SOLD 01/17/23

$325,000

$330,000

MLS#MFRL4932375

3810 Sleepy Hill Oaks Loop
Lakeland, FL 33810

4

2

2

2,162 SqFt

0.32 Acres

SOLD 01/13/23

$189,900

$199,900

MLS#MFRU8183106

3773 Pioneer Trails Blvd E
Lakeland, FL 33810

3

2

Pool

0.24 Acres

SOLD 03/10/23

$275,000

$279,000

MLS#MFRS5077495

3157 Pioneer Trails Loop
Lakeland, FL 33810

4

2

0.24 Acres

SOLD 10/14/21

$185,000

MLS#MFRU8132678

3771 Pioneer Trails Dr
Lakeland, FL 33810

3

2

0.24 Acres

SOLD 10/29/21

$189,900

MLS#MFRT3318175

3744 Pioneer Trails St
Lakeland, FL 33810

3

2

0.24 Acres

SOLD 05/15/23

$230,000

MLS#MFRT3440817

3642 Pioneer Trails Dr
Lakeland, FL 33810

3

2

0.24 Acres

SOLD 12/14/21

$112,000

MLS#MFRP4918008

3592 Pioneer Trails E
Lakeland, FL 33810

3

2

0.24 Acres

SOLD 10/04/23

$259,900

MLS#MFRP4927184

3642 Pioneer Trails Dr
Lakeland, FL 33810

3

2

0.24 Acres

SOLD 01/23/24

$215,000

MLS#MFRO6155311

3165 Pioneer Trails Loop
Lakeland, FL 33810

3

2

0.25 Acres

SOLD 03/15/24

$160,000

MLS#MFRL4942872

3610 Pioneer Trails St
Lakeland, FL 33810

3

2

0.27 Acres

SOLD 04/24/24

$239,900

MLS#MFRL4943313

3181 Pioneer Trails Loop
Lakeland, FL 33810

3

2

0.25 Acres

SOLD 08/14/24

$221,000

$243,500

MLS#MFRS5102054

3619 Pioneer Trails Dr
Lakeland, FL 33810

3

2

0.24 Acres

SOLD 06/24/24

$399,900

MLS#MFRL4944012

3857 Sleepy Hill Oaks Loop
Lakeland, FL 33810

4

2

2

2,533 SqFt

Pool

0.24 Acres

SOLD 07/30/24

$229,900

MLS#MFRB4901568

3610 Pioneer Trails St
Lakeland, FL 33810

3

2

0.27 Acres

SOLD 08/23/24

$249,900

MLS#MFRS5106004

3644 Pioneer Trails St
Lakeland, FL 33810

3

2

0.5 Acres

SOLD 03/05/15

$34,000

MLS#MFRL4701964

3591 Pioneer Trails Blvd E
Lakeland, FL 33810

4

2

0.24 Acres

SOLD 12/04/14

$59,900

MLS#MFRL4703165

3771 Pioneer Trails Dr
Lakeland, FL 33810

3

2

0.24 Acres

SOLD 06/16/15

$142,400

MLS#MFRT2747041

3326 Sleepy Hill Oaks Ln
Lakeland, FL 33810

4

2

2

2,626 SqFt

0.26 Acres

SOLD 06/05/15

$30,000

MLS#MFRO5362023

3795 Pioneer Trails Dr
Lakeland, FL 33810

3

2

0.24 Acres

SOLD 06/29/15

$74,900

MLS#MFRL4706193

3173 Pioneer Trails Loop
Lakeland, FL 33810

4

3

0.25 Acres

SOLD 12/16/15

$59,900

$63,000

MLS#MFRL4708420

3710 Pioneer Trails Blvd E
Lakeland, FL 33810

3

2

0.24 Acres

SOLD 01/11/16

$84,000

MLS#MFRL4710527

3838 Pioneer Trails Blvd E
Lakeland, FL 33810

3

2

1

0.24 Acres

SOLD 08/19/16

$70,000

MLS#MFRP4711440

3844 Pioneer Trails St
Lakeland, FL 33810

4

2

0.24 Acres

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

0 Active Listings in Sleepy Hill Oaks