Highland Woods

Highland Woods is a gated community of single family homes in Dunedin, Florida, with a range of options priced between $335,000 and $900,000. There are currently a total of 4 homes for sale in Highland Woods. The smallest Highland Woods home presently available is a four bedroom two bathroom residence that is 2,983 square feet (2,298SF Under Air living space), and the largest of the Highland Woods homes currently on the market has five beds and three baths and is a 4,640 square foot (3,693SF Under Air) residence.

Property management fees in Pinellas County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Highland Woods range from $595 to $1,143. 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 Highland Woods home.

The Highland Woods 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 three commercial airports that serve Highland Woods - Tampa International (TPA), which is fourteen miles away; Lakeland Linder International (LAL), which is 44 miles away, and Sarasota Bradenton International (SRQ), which is 46 miles away.

Highland Woods real estate activity on the Dunedin MLS during the past year (as of September 2025) reflects nine homes changing hands, with an average asking price of $845,400 and an average selling price of $827,722. This represents a healthy list-to-sell price ratio of 98% and $200 per square foot. During this period, Highland Woods homes for sale have taken an average of 52 days to sell.

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

Highland Woods Homes For Sale

Reduced

$898,500

$899,000

MLS#MFRTB8401906

2253 Hannah Way S
Dunedin, FL 34698

4

4

2

4,622 SqFt

Pool

0.22 Acres

89 Days

$895,000

MLS#MFRTB8431000

2281 Highland Woods Dr
Dunedin, FL 34698

4

4

3

4,527 SqFt

Pool

0.23 Acres

4 Days

Under Contract

$875,000

MLS#MFRTB8419816

2298 Hannah Way N
Dunedin, FL 34698

5

3

3

3,510 SqFt

Pool

0.26 Acres

35 Days

Reduced

$739,999

$799,900

MLS#MFRTB8396786

2228 Hannah Way S
Dunedin, FL 34698

4

3

3

4,036 SqFt

0.22 Acres

103 Days

4 Active Listings in Highland Woods