Homes for Sale in Cherokee Park West of Trail Sarasota

New Listing

1732 North Dr, Sarasota

$2,850,000

• 5 Beds
• 5 Baths
• 4,552 Sf

Cherokee Park 2

This home is the ultimate illustration of British West Indies, nestled on a mainland tree-lined Street in what is considered Sarasota’s best neighborhood, Cherokee Park. Between downtown Sarasota a...

1754 South Dr, Sarasota

$1,299,900

• 4 Beds
• 3 Baths
• 3,109 Sf

Cherokee Park 2

Significant price reduction!!! It doesn't get much better than living in Cherokee Park and here is your opportunity on South Drive. This updated 4/5 bedroom 3 bath home is move in ready. The curre...

1671 North Dr, Sarasota

$1,399,900

• 5 Beds
• 3 Baths
• 3,671 Sf

Cherokee Park 2

This is a one-of-a-kind, two-story custom home nestled on a beautiful lot in sought after West of the Trail "Cherokee Park". This home offers a combination of outstanding craftsmanship and customiz...

1509 S Lodge Dr, Sarasota

$4,795,000

• 5 Beds
• 6 Baths
• 5,800 Sf

Cherokee Park

The spectacular location of this waterfront home is quite unique. Resting on nearly 2/3-acre of property at the end of a quiet cul-de-sac, just one parcel in from the point-lot location that overlo...

1766 Cherokee Dr, Sarasota

$2,249,000

• 6 Beds
• 7 Baths
• 5,328 Sf

Cherokee Park 2

Located in the coveted West of the Trail neighborhood of Cherokee Park, this spacious Key West-style family compound on nearly a half acre offers beautifully appointed amenities, lush tropical land...

1631 Spring Creek Dr, Sarasota

$739,000

• 4 Beds
• 3 Baths
• 2,976 Sf

Cherokee Park

Enjoy the best of both worlds in this 4/5 bedroom home on over nearly a third of an acre just minutes from the sugar white sands of Siesta Beach voted #1 in the United States and all that is beauti...

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Cherokee Park Real Estate Market

This small, serene, real estate market in Sarasota boasts a diversity of architectural design styles, ranging from the boom time revival period to a post World War II modern theme. The impressive Florida mansions built here in the 50’s and 60’s on this community’s palm-lined roads adds a feeling of being sent back in time to the growth years in Sarasota after the Second World War.

Originally designed in 1926, the subdivision is separated from Osprey Avenue by a stucco wall and gate posts with impressive artistic tile work depicting a beautiful Cherokee rose. The developer, J.C. Brown, had a vision for Cherokee Park - creating a neighborhood filled with homes designed in Italian, Spanish or Moorish styles of architecture. There are a wide variety of homes in Cherokee Park. You can find an old Florida ranch style home, a Mc Mansion and everything in between. Because of land values most of the homes haves been remodeled or rebuilt. 

Streets in Cherokee Park - Cherokee Drive, South Drive, North Drive.