101 OSPREY POINT DR, Osprey, FL 34229
See all 65 photos
101 OSPREY POINT DR, Osprey, FL 34229
101 OSPREY POINT DR, Osprey, FL 34229
101 OSPREY POINT DR, Osprey, FL 34229
101 OSPREY POINT DR, Osprey, FL 34229
REQUEST A TOUR If you would like to see this home without being there in person, select the "Virtual Tour" option and your advisor will contact you to discuss available opportunities.
In-PersonVirtual Tour
Rich Ganim

Rich Ganim

+1(440) 482-8317
$ 4,790,000
Est. payment /mo
Save Virtual Tour
New

101 OSPREY POINT DR Osprey, FL 34229

4 Beds

6 Baths

5,087 SqFt

UPDATED:

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 $941

Subdivision The Oaks

MLS Listing ID A4694716

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

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota's prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community's most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef's kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler's pantry and sunlit breakfast nook overlooking the gardens further enhance the home's livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota's premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast's most established luxury communities.

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

Furnishings Unfurnished

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

Stellar MLS
© 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved.
Listed by Joel Schemmel DOUGLAS ELLIMAN
Rich Ganim

Rich Ganim

Team Leader

+1(440) 482-8317

GET MORE INFORMATION

Name
Phone*
Message

By checking this box, I agree by electronic signature to the Electronic Disclosure Consent Agreement; to receive recurring marketing communication from The Ganim Group, including auto-dialed calls, texts, and artificial/prerecorded voice messages (message frequency varies; data rates may apply; reply "STOP" to opt-out of texts or "HELP" for assistance); and to the Terms of Service and Privacy Policy of this website. Consent not required to make a purchase. I understand that I can call to obtain direct assistance.

Go tour this home

101 OSPREY POINT DR

};