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75 Osprey Point DriveOsprey, FL 34229Price: $1,649,000

  • Price: $1,649,000
  • Est. Mortgage of $/month
  • 34 Days on Market
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Federal 30-year interest rate: 6.49% last updated on Jul 9, 2026
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  • $1,649,000List Price
  • ActiveStatus
  • 70Number of Photos
  • 27.207976Latitude
  • 75 Osprey Point DriveAddress
  • Osprey Point DriveStreet
  • OspreyTown
  • FLState
  • 34229Zip
  • SarasotaCounty
  • A4695145MLS Number
  • 06/11/2026Date Listed
  • 4Bedrooms
  • 4Full Bath
  • 4,001Square Feet
  • 1983Year Built
  • 0.76Acreage
  • 35 DaysOnMarket Date

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Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

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LISTING COURTESY OF Steve Abbe of COLDWELL BANKER REALTY (941-383-6411)

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of July 14, 2026 11:35 PM 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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