The Highlands Winter Springs

The Highlands is a community of single family homes, condos, and townhomes in Winter Springs, Florida, with a range of options priced between $155,000 and $519,500. There are currently a total of 19 homes for sale in The Highlands. The smallest Highlands home presently available is a two bedroom two bathroom residence that is 1,042 square feet (974SF Under Air living space), and the largest of the The Highlands homes currently on the market has three beds and two baths and is a 2,726 square foot (2,022SF Under Air) residence.

Property management fees in Seminole County vary depending on the community and the subdivision within the community and sometimes vary between homes in the subdivision. The current HOA fees for homes in The Highlands range from $40 to $475 and are $504 for a The Highlands condo and $180 to $1,561 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and real estate taxes for common areas. Also included is property insurance, water, 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 The Highlands home.

The Highlands amenities include a clubhouse, swimming pool, and spa / hot tub. Sports facilities include a championship golf course, tennis courts, pickleball courts, racquetball, basketball court, and shuffleboard. There is also a community park, a playground, as well as walking or jogging trails.

The The Highlands Master HOA does allow pets, however the various subdivision may impose their own pet restrictions, so check the individual listings for specifics.

There are two subdivisions in The Highlands - Greenpointe, and The Cypress Club.

There are four commercial airports that serve The Highlands - Orlando Sanford International (SFB), which is seven miles away; Orlando Executive (ORL), which is eleven miles away; Orlando International (MCO), which is nineteen miles away, and Kissimmee Gateway (ISM), which is 30 miles away from The Highlands.

The Highlands real estate activity on the Winter Springs MLS during the past year (as of February 2026) reflects 40 homes changing hands, with an average asking price of $277,337 and an average selling price of $268,301. This represents a healthy list-to-sell price ratio of 97% and $137 per square foot. During this period, The Highlands homes for sale have taken an average of 73 days to sell.

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

The Highlands Homes For Sale

Under Contract

$485,950

$538,900

MLS#MFRO6286220

811 Gatehouse Dr
Winter Springs, FL 32708

3

2

2

2,726 SqFt

0.3 Acres

344 Days

$470,000

MLS#MFRO6379428

416 Macgregor Rd
Winter Springs, FL 32708

3

3

2

2,565 SqFt

0.11 Acres

10 Days

Under Contract

$399,999

MLS#MFRO6358032

838 Dunbar Ter
Winter Springs, FL 32708

3

2

2

1,680 SqFt

0.23 Acres

99 Days

Reduced

$399,000

$420,000

Greenpointe

622 Anhinga Rd
Winter Springs, FL 32708

3

3

2

2,166 SqFt

0.14 Acres

52 Days

Under Contract

$385,000

$419,000

Greenpointe

625 Nighthawk Cir
Winter Springs, FL 32708

3

2

2

2,256 SqFt

0.16 Acres

256 Days

$385,000

MLS#MFRTB8437197

744 N Gretna Ct
Winter Springs, FL 32708

3

2

2

1,265 SqFt

0.23 Acres

124 Days

$289,900

MLS#MFRO6378613

100 Silver Sea Rd
Winter Springs, FL 32708

2

2

1

1,653 SqFt

0.06 Acres

14 Days

Reduced

$287,900

$294,900

MLS#MFRO6375532

337 Kirkcaldy Dr
Winter Springs, FL 32708

2

2

1,042 SqFt

0.11 Acres

14 Days

$279,900

The Cypress Club

446 Club Dr
Winter Springs, FL 32708

3

2

1,512 SqFt

0.03 Acres

2 Days

$245,000

MLS#MFRS5139927

429 Sheoah Blvd #8
Winter Springs, FL 32708

3

2

1,187 Sq Ft

1187 Acres

68 Days

Reduced

$237,000

$239,000

The Cypress Club

506 Club Dr
Winter Springs, FL 32708

2

2

1,200 SqFt

0.04 Acres

86 Days

Reduced

$235,000

$250,000

The Cypress Club

498 Club Dr
Winter Springs, FL 32708

2

2

1,280 SqFt

0.03 Acres

190 Days

You may also be interested in The Highlands in Miami, The Highlands in Deland, The Highlands in Lakeland, The Highlands in North Miami Beach or The Highlands in Valrico.

19 Active Listings in The Highlands