101 Osprey Point Drive, Osprey, FL 34229

Local realty services provided by:Tomlin St Cyr Real Estate Services ERA Powered
101 Osprey Point Drive,Osprey, FL 34229
$5,000,000
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  • 4 Beds
  • 6 Baths
  • 5,087 sq. ft.
  • Single family
  • Active
Listed by: joel schemmel
Office: douglas elliman
MLS#:A4664424
Source:MFRMLS

Price summary

  • Price:$5,000,000
  • Price per sq. ft.:$730.89
  • Monthly HOA dues:$950

About this home

A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances architectural distinction with thoughtful updates that ensure comfort and livability. An oversized circular drive paved in granite tile leads to a stately double-door entrance. Inside, the foyer sets the tone with soaring ceilings, hand-crafted moldings, chandeliers, and a white onyx floor with marble inserts. Spaces include an oversized living room with dual fireplaces, a crystal chandelier, and multiple sets of French doors opening to the lakefront patio. The dining room, anchored by another fireplace and framed by custom casings and built-in shelving, is ideal for grand entertaining. A

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Home facts

  • Year built:1985
  • Listing ID #:A4664424
  • Added:157 day(s) ago
  • Updated:February 22, 2026 at 04:47 PM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:6
  • Full bathrooms:5
  • Half bathrooms:1
  • Living area:5,087 sq. ft.

Heating and cooling

  • Cooling:Central Air, Zoned
  • Heating:Central, Electric, Zoned

Structure and exterior

  • Roof:Tile
  • Year built:1985
  • Building area:5,087 sq. ft.
  • Lot area:0.93 Acres

Schools

  • High school:Venice Senior High
  • Middle school:Sarasota Middle
  • Elementary school:Laurel Nokomis Elementary

Utilities

  • Water:Public, Water Connected, Well
  • Sewer:Public, Public Sewer, Sewer Connected

Finances and disclosures

  • Price:$5,000,000
  • Price per sq. ft.:$730.89
  • Tax amount:$12,940 (2025)
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