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 $150,000 and $519,500. There are currently a total of 17 homes for sale in The Highlands. The smallest Highlands home presently available is a three bedroom two bathroom residence that is 1,196 square feet (972SF Under Air living space), and the largest of the The Highlands homes currently on the market has four beds and three baths and is a 2,726 square foot (2,185SF 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 $33 to $404 and are $404 for a The Highlands condo and $420 to $1,080 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 November 2025) reflects 48 homes changing hands, with an average asking price of $293,985 and an average selling price of $287,728. This represents a healthy list-to-sell price ratio of 98% and $140 per square foot. During this period, The Highlands homes for sale have taken an average of 68 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

Reduced

$492,000

$538,900

MLS#MFRO6286220

811 Gatehouse Dr
Winter Springs, FL 32708

3

2

2

2,726 SqFt

0.3 Acres

253 Days

Reduced

$450,000

$525,000

MLS#MFRO6334935

821 Sheoah Cir
Winter Springs, FL 32708

3

3

2

2,606 SqFt

0.18 Acres

96 Days

Reduced

$415,000

$425,000

MLS#MFRO6336189

746 N Gretna Ct
Winter Springs, FL 32708

3

2

2

1,652 SqFt

0.18 Acres

88 Days

$399,999

MLS#MFRO6358032

838 Dunbar Ter
Winter Springs, FL 32708

3

2

2

1,680 SqFt

0.23 Acres

8 Days

Under Contract

$399,999

$470,000

MLS#MFRS5129323

878 Elgin Dr
Winter Springs, FL 32708

4

3

2

2,008 SqFt

0.2 Acres

150 Days

Reduced

$390,000

$419,000

Greenpointe

625 Nighthawk Cir
Winter Springs, FL 32708

3

2

2

2,256 SqFt

0.16 Acres

165 Days

$385,000

MLS#MFRTB8437197

744 N Gretna Ct
Winter Springs, FL 32708

3

2

2

1,265 SqFt

0.23 Acres

33 Days

Under Contract

$375,000

$414,000

MLS#MFRO6347470

416 Macgregor Rd
Winter Springs, FL 32708

3

3

2

2,565 SqFt

0.11 Acres

49 Days

Under Contract

$275,000

Greenpointe

662 Nighthawk Cir
Winter Springs, FL 32708

3

3

2

2,140 SqFt

0.11 Acres

11 Days

$250,000

The Cypress Club

498 Club Dr
Winter Springs, FL 32708

2

2

1,280 SqFt

0.03 Acres

99 Days

Reduced

$239,900

$249,900

MLS#MFRV4944893

505 Moree Loop
Winter Springs, FL 32708

2

3

1,535 SqFt

0.04 Acres

62 Days

Reduced

$210,000

$235,000

MLS#MFRO6333905

30 Moree Loop #39
Winter Springs, FL 32708

3

3

1,452 Sq Ft

0.03 Acres

86 Days

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

17 Active Listings in The Highlands