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3408 Winding Oaks Drive, Unit 53Longboat Key, FL 34228Sale Price: $1,175,000

  • Sale Price: $1,175,000
  • 873 Days Since Sale
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  • $1,175,000Sale Price
  • SoldStatus
  • 1Number of Photos
  • 27.377941Latitude
  • 3408 Winding Oaks DriveAddress
  • Winding Oaks DriveStreet
  • 53Unit Number
  • Longboat KeyTown
  • FLState
  • 34228Zip
  • SarasotaCounty
  • A4593159MLS Number
  • 12/27/2023Date Listed
  • 2Bedrooms
  • 2Full Bath
  • 1Half Baths
  • 2,039Square Feet
  • 1988Year Built
  • 1Acreage
  • 943 DaysOnMarket Date

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Experience your refined tropical lifestyle in this meticulously renovated 2BR/2.5BA, 2,039+/- sq. ft. home nestled within the charming and exclusive Winding Oaks community on Longboat Key. The architecturally pleasing faade, adorned with awnings and a stylish color scheme, sets the tone for the luxury that awaits. As you approach, the mature landscaping and inviting courtyard at the entry beckon you inside, where high ceilings and tile floors create an open and spacious ambiance. The stylish kitchen, with a breakfast bar, boasts creatively contrasting blue cabinetry with white appliances and solid surface countertops. A family room off the kitchen provides a cozy space to gather, while the living room captivates with a fireplace and walls of sliders leading to the expansive open deck and private pool. The large primary suite is a relaxing respite with its cathedral ceiling, slider access to the pool deck and a voluminous custom walk-in closet. The beautifully redone primary bath features dual vanities, a glass walk-in shower and recessed lighting, adding a touch of elegance. The outdoor experience is equally grand, with a vast pool deck providing ample space for entertaining guests in the open air and a private pool for cooling down during those balmy summer days. Complete with high-impact glass all around, a 2-car garage, a whole house water filter and softener, and security system this residence embodies the pinnacle of luxury living. Set in the Bay Isles Harbourside golf course community, Winding Oaks is an intimate, maintenance-free neighborhood of just 56 villa-style residences offering a range of exciting amenities, including a gated entry, community pool and spa, recreational facilities, social activities and so much more. Residents of Winding Oaks are welcome to take advantage of all the benefits of Bay Isles living including deeded beach access to the Bay Isles Beach Club.

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LISTING COURTESY OF Bruce Myer of COLDWELL BANKER REALTY (941-383-6411)

Listing Sold by MICHAEL SAUNDERS & COMPANY

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of July 26, 2026 8:01 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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Property Details of 3408 Winding Oaks Drive, Unit 53

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