Shoreland Woods

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Overview

Shoreland Woods is a small West of the Trail neighborhood. Located off Osprey Drive a little north of Siesta Drive and south of Cherokee Park, some of the homes here are facing Sarasota Bay. Most of the homes in this neighborhood are inland, but in one of Sarasota's most demanded areas.

West of the Trail homes are close to Sarasota Memorial Hospital, excellent schools, Southgate Mall, Southside Village shopping and restaurants. Families love the area. Most homes in Shoreland Woods are within walking distance to Southside Elementary School. Selby Gardens, the downtown bayfront and the cultural activities of downtown Sarasota are all within an easy drive of this hot "West of the Trail" area.

MLS® Listing Statistics

Total Listings: 4
Average Price: $5,473,750
Highest Price: $9,800,000
Lowest Price: $2,295,000
Average Size: 4,149 ft²
Average Price Per Square Foot: $1,295 per ft²

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Shoreland Woods

Homes for Sale in Shoreland Woods

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Image 0: A4632433

3350 Old Oak Drive, SARASOTA, FL - $9,800,000

Residential, Single Family Residence
  • 7 Beds
  • 8 Baths
  • 7,181 SQFT
  • 133 DOM
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Rarely Does An Opportunity Like This Come To Market, Offering A Piece Of Old Florida On 2.1 Lush Acres And Boasting Breathtaking Views Of Sarasota Bay, Siesta Key, Bird Key, Ringling Bridge, And Downtown Sarasota, This Magnificent Family Compound ...

3350 Old Oak Drive, SARASOTA, FL - $6,500,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,263 SQFT
  • 133 DOM
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Rarely Does An Opportunity Like This Come To Market—a Chance To Own A Piece Of Old Florida On Over An Acre Of Lush, Private Grounds. Nestled In Total Seclusion, This Extraordinary Compound Offers Panoramic Views Of Sarasota Bay, Siesta Key, Bird K...

3348 Old Oak Drive, SARASOTA, FL - $3,300,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,668 SQFT
  • 133 DOM
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Stunning Mid Century Masterpiece, Close To Beach And Walk To Southside Village. Featuring Cypress Inside And Out. High Ceilings And Open Spaces Offer Comfort And Airiness, While The Walls Of Glass Sliders And Windows Fill The Interior With Natural...

Image 3: A4638734

3331 Old Oak Drive, SARASOTA, FL - $2,295,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 2,483 SQFT
  • 83 DOM
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Come Experience A Coastal Sanctuary Of Timeless Elegance And Modern Luxury! Nestled In The Prestigious West Of The Trail Enclave, This Exquisitely Reimagined Old Florida Gated Estate Is A Harmonious Blend Of Sophisticated Elegance And Modern Indu...

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on April 28th, 2025 at 3:35pm EDT.

Map of Shoreland Woods

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