101 OSPREY POINT DR, Osprey, FL 34229 - MLS#A4664424

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2026

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Alina Pekarsky

alina@vhrfl.com +1(386) 569-5383

$5,000,000

Est. payment - /mo

4 Beds

6 Baths

5,087 SqFt

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Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 5,087 sqft

Price per Sqft $982

Subdivision The Oaks

MLS Listing ID A4664424

Bedrooms 4

Full Baths 5

Half Baths 1

HOA Fees $5,700/Semi-Annually

HOA Y/N Yes

Annual Recurring Fee 11400.0

Year Built 1985

Annual Tax Amount $12,940

Lot Size 0.930 Acres

Acres 0.93

Property Sub-Type Single Family Residence

Source Stellar MLS

Property Description

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 domed ceiling sitting room with French doors to the patio adds an intimate space for cocktails or conversation, while the custom bar and wine room, with etched glass cabinetry, stone counters, and display shelving, enhances the home's appeal for gatherings. The kitchen, completely remodeled in 2019, is a showcase of craftsmanship with UltraKraft® cabinetry, custom soffit lighting, Corian countertops, and a center island with breakfast bar. Luxury appliances include a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, microwave, warming drawer, two KitchenAid dishwashers, and a Frigidaire wine fridge. A butler's pantry provides additional storage, while the sunny breakfast nook overlooks lush gardens. Family and gathering rooms carry the same sense of scale, with dramatic fireplaces, intricate moldings, and detailed ceiling treatments that flow seamlessly for everyday living or large-scale entertaining. The primary suite is a true retreat with a spacious sitting area, custom closets, and a well-appointed bathroom that was newly remodeled in 2025 with spa-inspired finishes. Three guest suites, each with updated full baths (2021 and 2025), provide privacy and comfort. One is a suite with a bathroom near the laundry room, which offers flexibility for live-in staff or extra accommodation. Outdoors, the home embraces its setting with an open pool, expansive deck, and cabana surrounded by manicured hedges and mature landscaping. The views are equally compelling, with mature gardens and community reflecting pond in the front and sweeping lake vistas in the back. Additional highlights include a three-car garage, refinished hardwood floors (2020), and a new Daikin 5-ton AC system installed in 2022. Ownership at The Oaks Club brings an unmatched lifestyle, with two championship golf courses, tennis and pickleball courts, croquet, a fitness center and spa, three on-site restaurants, and a community dock on Little Sarasota Bay. Elegant yet inviting, 101 Osprey Point Drive stands as a rare opportunity to enjoy lakefront living with resort-style amenities in one of Sarasota's most established private enclaves.

Location

State FL

County Sarasota

Community The Oaks

Area 34229 - Osprey

Zoning RSF1

Rooms

Other Rooms Breakfast Room Separate, Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate

Interior

Interior Features Built-in Features, Ceiling Fans(s), Chair Rail, Crown Molding, Eat-in Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar, Window Treatments

Heating Central, Electric, Zoned

Cooling Central Air, Zoned

Flooring Brick, Ceramic Tile, Parquet

Fireplaces Type Family Room, Living Room, Other, Primary Bedroom, Wood Burning

Fireplace true

Appliance Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Washer, Water Filtration System, Water Softener, Wine Refrigerator

Laundry Inside, Laundry Room

Exterior

Exterior Feature French Doors, Hurricane Shutters, Lighting, Private Mailbox

Parking Features Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street

Garage Spaces 3.0

Pool Gunite, In Ground

Community Features Buyer Approval Required, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Special Community Restrictions, Tennis Court(s), Street Lights

Utilities Available BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Propane, Public, Sewer Connected, Sprinkler Well, Water Connected

Amenities Available Clubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(s)

Waterfront Description Lake Front

View Y/N Yes

View Water

Roof Type Tile

Porch Front Porch, Rear Porch

Attached Garage true

Garage true

Private Pool Yes

Building

Lot Description Cul-De-Sac, In County, Landscaped, Paved

Entry Level One

Foundation Slab

Lot Size Range 1/2 to less than 1

Sewer Public Sewer

Water Public, Well

Architectural Style Custom, Traditional

Structure Type Block,Stucco

New Construction false

Schools

Elementary Schools Laurel Nokomis Elementary

Middle Schools Sarasota Middle

High Schools Venice Senior High

Others

Pets Allowed Yes

HOA Fee Include Guard - 24 Hour,Pool,Management,Private Road,Security

Senior Community No

Pet Size Extra Large (101+ Lbs.)

Ownership Fee Simple

Monthly Total Fees $950

Acceptable Financing Cash, Conventional

Membership Fee Required Required

Listing Terms Cash, Conventional

Special Listing Condition None

Virtual Tour https://listings.threesixtyviews.net/videos/019953f8-eec5-710f-bd80-86bf091497ce

Porch Type Front Porch,Rear Porch

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Listed by Joel Schemmel DOUGLAS ELLIMAN

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Alina Pekarsky

+1(386) 569-5383

Broker | BKBK3118291

Broker BKBK3118291

101 OSPREY POINT DR Osprey, FL 34229

Alina Pekarsky

Key Details

Location

Rooms

Interior

Exterior

Building

Schools

Others

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