Highland Lakes Leesburg

Highland Lakes is a gated community of single family homes, and townhomes in Leesburg, Florida, with a range of options priced between $189,900 and $440,000. There are currently a total of 39 homes for sale in Highland Lakes. The smallest Highland Lakes home presently available is a two bedroom two bathroom residence that is 1,120 square feet, and the largest of the Highland Lakes homes currently on the market has four beds and two baths and is a 3,635 square foot (2,585SF Under Air) residence.

Property management fees in Lake County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Highland Lakes range from $114 to $281 and $220 to $279 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and security. Also included is a 24-hour guard, real estate taxes for common areas, property insurance, gas, trash removal, sewer, pest control, Cable TV & internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Highland Lakes home.

Highland Lakes amenities include a clubhouse, swimming pool, spa / hot tub, a state-of-the-art fitness center, and sauna. Sports facilities include a championship golf course, tennis courts, pickleball courts, racquetball, basketball court, and shuffleboard. There is also a community park, a playground, a dog park, as well as walking or jogging trails.

The Highland Lakes HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limit of how many pets you may have, and there is a restriction on pet size. Dogs and cats are allowed.

There are four commercial airports that serve Highland Lakes - Orlando Executive (ORL), which is 34 miles away; Orlando Sanford International (SFB), which is 38 miles away; Orlando International (MCO), which is 39 miles away, and Kissimmee Gateway (ISM), which is 40 miles away from Highland Lakes.

Highland Lakes real estate activity on the Leesburg MLS during the past year (as of December 2025) reflects 67 homes changing hands, with an average asking price of $275,884 and an average selling price of $265,031. This represents a healthy list-to-sell price ratio of 96% and $111 per square foot. During this period, Highland Lakes homes for sale have taken an average of 118 days to sell.

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

Highland Lakes Homes For Sale

Reduced

$440,000

$450,000

MLS#MFRG5103611

27238 Stoney Brook Dr
Leesburg, FL 34748

4

2

3

3,635 SqFt

0.25 Acres

52 Days

Reduced

$417,000

$427,000

MLS#MFRG5101669

27303 Stoney Brook Dr
Leesburg, FL 34748

3

2

2

3,265 SqFt

Water Front

0.26 Acres

103 Days

$385,000

MLS#MFRG5103638

5609 Rosewall Cir
Leesburg, FL 34748

3

3

3

3,526 SqFt

0.02 Acres

48 Days

Under Contract

$365,000

MLS#MFRG5103696

27400 Stoney Brook Dr
Leesburg, FL 34748

3

3

2

2,780 SqFt

0.15 Acres

52 Days

$327,000

MLS#MFRG5103158

5839 Woodland Moss Way
Leesburg, FL 34748

3

2

2

2,741 SqFt

0.25 Acres

65 Days

Reduced

$325,000

$330,000

MLS#MFRG5102123

27313 Falcon Feather Way
Leesburg, FL 34748

3

2

2

2,073 SqFt

0.12 Acres

81 Days

Under Contract

$320,000

MLS#MFRG5104026

26450 Evert St
Leesburg, FL 34748

3

2

2

2,651 SqFt

0.18 Acres

32 Days

Under Contract

$312,500

MLS#MFRO6352292

27435 Stoney Brook Dr
Leesburg, FL 34748

3

2

2

2,610 SqFt

0.21 Acres

61 Days

Reduced

$309,900

$319,900

MLS#MFRG5103959

6131 Wilander St
Leesburg, FL 34748

3

2

2

2,930 SqFt

0.27 Acres

32 Days

Reduced

$309,900

$320,000

MLS#MFRG5103771

26600 Racquet Cir
Leesburg, FL 34748

3

2

2

2,745 SqFt

0.21 Acres

40 Days

Reduced

$299,000

$315,000

MLS#MFRG5101130

27536 Stoney Brook Dr
Leesburg, FL 34748

3

2

2

2,154 SqFt

0.17 Acres

115 Days

$288,900

MLS#MFRG5103058

5616 Laver St
Leesburg, FL 34748

2

2

2

2,879 SqFt

0.23 Acres

52 Days

You may also be interested in Highland Lakes in Miami or Highland Lakes in Bradenton.

39 Active Listings in Highland Lakes