Top 10 Most Expensive Streets in Hawks Crest, Winter Park, FL

The following are the Top 10 most expensive streets in Hawks Crest. The average price for homes on these streets range from $455,000 to $4,330,000.

Spring is coming

Thinking of selling your home this spring?

Now is the time to start preparing your home so you'll be ready to beat the competition in Spring! Let our real estate professionals advise you on what improvements will make your home most appealing and add the most value. We can offer you tips on how to make your home stand out above the rest and increase your odds for a more successful sale.

Russell Shaw

Call Russell Today! (888) 326-2726

1. Tom Gurney Drive

Tom Gurney Drive is the 1st most expensive street in Winter Park. It has single-family homes built in 1997, with an average sale price of $4,330,000. It is home to the Tuscania subdivision.

Average Price: $4,330,000
View All Recent Sales divider

2. Fosgate Drive

Fosgate Drive is the 2nd most expensive street in Winter Park. It has single-family homes built from 1956 to 1957, ranging in price from $999,999 to $1,186,200. It is home to the Timberlane subdivision.

Average Price: $1,093,099.50
View All Recent Sales divider

3. Lake Howell Lane

Lake Howell Lane is the 3rd most expensive street in Winter Park. It has land and single-family homes built from 1954 to 1996, ranging in price from $1,099,000 to $3,400,000.

Average Price: $2,333,000
View All Recent Sales divider

4. Overlook Road

Overlook Road is the 4th most expensive street in Winter Park. It has single-family homes built from 1925 to 1936, with an average sale price of $1,000,000. It is home to the Sylvan Lake Shores subdivision.

Average Price: $1,000,000
View All Recent Sales divider

5. Soaring Oak Way

Soaring Oak Way is the 5th most expensive street in Winter Park. It has single-family homes built in 2021, ranging in price from $899,000 to $1,080,000. It is home to the Waters Edge at Hawks Crest subdivision.

Average Price: $993,000
View All Recent Sales divider

6. Pennsylvania Avenue

Pennsylvania Avenue is the 6th most expensive street in Winter Park. It has townhouses, condos, single-family homes, land, and multi-units built from 1962 to 2017, ranging in price from $290,000 to $2,400,000. It is home to the Casa Jardin, Morseland, Virginia Heights, and Penn Place subdivisions.

Average Price: $816,528.57
View All Recent Sales divider

7. Woodland Avenue

Woodland Avenue is the 7th most expensive street in Winter Park. It has single-family homes built in 1953, with an average sale price of $750,000. It is home to the Comstock Park subdivision.

Average Price: $750,000
View All Recent Sales divider

8. Golfside Drive

Golfside Drive is the 8th most expensive street in Winter Park. It has single-family homes built from 1969 to 2002, ranging in price from $575,000 to $1,122,500. It is home to the Greenview at Winter Pines and Golfside subdivisions.

Average Price: $718,970
View All Recent Sales divider

9. Lake Howell Road

Lake Howell Road is the 9th most expensive street in Winter Park. It has single-family homes built from 1956 to 2025, ranging in price from $340,000 to $1,095,000. It is home to the Tanglewood subdivision.

Average Price: $466,040
View All Recent Sales divider

10. Hampton Circle

Hampton Circle is the 10th most expensive street in Winter Park. It has single-family homes built in 1971, with an average sale price of $455,000. It is home to the Winter Woods subdivision.

Average Price: $455,000
View All Recent Sales divider View All Homes for Sale in Hawks Crest
Sold Homes

We have helped thousands of families buy and sell homes!

HomesByMarco agents are experts in the area. If you're looking to buy or sell a home, give us a call today at 888-326-2726.