Lakeside Estates

Lakeside Estates is a gated community of single family homes in Winter Park, Florida, with a range of options priced between $585,000 and $1,475,000. The smallest Lakeside Estates home in the community is a four bedroom three bathroom residence that is 3,825 square feet (3,057SF Under Air living space), and the largest of the Lakeside Estates homes has seven beds and five baths and is a 6,467 square foot (5,111SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Lakeside Estates range from $155 to $465. This fee includes security, and trash removal. Please check the individual listing pages for the exact homeowners association fees for a particular Lakeside Estates home.

The Lakeside Estates HOA rules do allow homeowners to have pets.

There are four commercial airports that serve Lakeside Estates - Orlando Executive (ORL), which is seven miles away; Orlando Sanford International (SFB), which is eleven miles away; Orlando International (MCO), which is fourteen miles away, and Kissimmee Gateway (ISM), which is twenty five miles away from Lakeside Estates.

Lakeside Estates real estate activity on the Winter Park MLS during the past year (as of October 2025) reflects three homes changing hands, with an average asking price of $1,253,333 and an average selling price of $1,215,000. This represents a healthy list-to-sell price ratio of 97% and $244 per square foot. During this period, Lakeside Estates homes for sale have taken an average of just 28 days to sell.

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

Lakeside Estates Homes For Sale

SOLD 03/11/25

$990,000

MLS#MFRO6268124

1484 Via Sangro Pl
Winter Park, FL 32792

4

3

3

4,179 SqFt

Pool

0.2 Acres

SOLD 07/01/24

$995,000

$1,070,000

MLS#MFRO6193168

1473 Via Sangro Pl
Winter Park, FL 32792

4

3

3

3,825 SqFt

Pool

0.22 Acres

SOLD 11/24/16

$825,000

$888,888

MLS#MFRO5440750

1464 Via Sangro Pl
Winter Park, FL 32792

7

5

4

6,467 SqFt

Pool

0.23 Acres

SOLD 06/09/23

$1,275,000

MLS#MFRO6103369

1464 Via Sangro Pl
Winter Park, FL 32792

7

5

4

6,467 SqFt

Pool

0.23 Acres

SOLD 12/05/24

$1,475,000

$1,600,000

MLS#MFRO6234041

1460 Via Sangro Pl
Winter Park, FL 32792

7

5

3

5,842 SqFt

Water Front

0.51 Acres

SOLD 01/25/18

$625,000

MLS#MFRO5553402

3715 Vinsetta Ct
Winter Park, FL 32792

4

3

3

4,179 SqFt

Pool

0.27 Acres

SOLD 08/22/25

$1,295,000

MLS#MFRO6325928

1422 Via Sangro Pl
Winter Park, FL 32792

6

4

3

4,899 SqFt

Pool

Water Front

0.42 Acres

SOLD 02/15/18

$585,000

MLS#MFRU7836260

3716 Vinsetta Ct
Winter Park, FL 32792

5

4

3

4,899 SqFt

0.21 Acres

New Construction

SOLD 03/27/23

$1,275,000

MLS#MFRO6073328

3708 Vinsetta Ct
Winter Park, FL 32792

6

5

3

6,257 SqFt

0.24 Acres

SOLD 06/28/23

$1,100,000

MLS#MFRO6082646

3720 Vinsetta Ct
Winter Park, FL 32792

6

5

3

6,041 SqFt

Pool

0.2 Acres

SOLD 09/26/24

$1,150,000

$1,200,000

MLS#MFRO6219248

3720 Vinsetta Ct
Winter Park, FL 32792

6

5

3

6,041 SqFt

Pool

0.2 Acres

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We do not have any properties available for sale in Lakeside Estates.

0 Active Listings in Lakeside Estates