Sarasota MLS Listings

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$5,000,000
26 Days On Site

101 OSPREY POINT DRIVE
OSPREY, FL 34229

For Sale|Single Family Residence|Active
4
Beds
6
Total Baths
5
Full Baths
1
Partial Bath
5,087
SqFt
$983
/SqFt
1985
Built
Subdivision:
THE OAKS
County:
Sarasota
Call Now: 941-265-2455
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941-265-2455
101 OSPREY POINT DRIVE101 OSPREY POINT DRIVE101 OSPREY POINT DRIVE101 OSPREY POINT DRIVE
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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.

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Listing Snapshot
Price 
$5,000,000
Days On Site 
26 Days
Bedrooms 
4
Inside Area (SqFt) 
5,087 sqft
Total Baths 
6
Full Baths 
5
Partial Baths 
1
Lot Size 
0.93 Acres
Year Built 
1985
MLS® Number 
A4664424
Status 
Active
Property Tax 
$12,940.05
HOA/Condo/Coop Fees 
$5,700 Semi-Annually
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
4 weeks agoListing updated with changes from the MLS®
4 weeks agoListing first seen on site
General Features
Acres 
0.93
Attached Garage 
Yes
Direction Faces 
West
Foundation 
Slab
Garage 
Yes
Garage Spaces 
3
Levels 
One
Parking 
Circular DrivewayDrivewayGarage Door OpenerGarage Faces SideOff StreetAttached
Pets 
Yes
Property Sub Type 
Single Family Residence
Security 
Gated CommunitySecurity System OwnedSmoke Detector(s)
Sewer 
Public Sewer
SqFt Total 
6841
Style 
CustomTraditional
Utilities 
Cable AvailableElectricity ConnectedPhone AvailablePropaneSewer ConnectedWater Connected
Water Source 
PrivatePublicWell
Zoning 
RSF1
Interior Features
Appliances 
Bar FridgeCooktopDishwasherDisposalDryerElectric Water HeaterMicrowaveRange HoodRefrigeratorWasherWater SoftenerWine Refrigerator
Cooling 
Central AirZoned
Fireplace 
Yes
Fireplace Features 
Family RoomLiving RoomOtherWood Burning
Flooring 
BrickCeramic TileParquet
Heating 
CentralElectricZoned
Interior 
Built-in FeaturesCrown MoldingEat-in KitchenHigh CeilingsStone CountersWalk-In Closet(s)Wet Bar
Laundry Features 
InsideLaundry Room
Spa 
Yes
Window Features 
Window CoveringsBlindsDrapesWindow Treatments
Bedroom 2 
Dimensions - 15x12Level - First
Bedroom 3 
Dimensions - 13x13Level - First
Bedroom 4 
Dimensions - 12x10Level - First
Dining Room 
Dimensions - 15x25Level - First
Family Room 
Dimensions - 20x20Level - First
Kitchen 
Dimensions - 16x23Level - First
Library 
Dimensions - 20x26Level - FirstFeatures - Bar
Living Room 
Level - First
Master Bathroom 
Level - FirstFeatures - Bidet
Master Bedroom 
Dimensions - 25x22Level - First
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Exterior Features
Construction Details 
BlockStucco
Exterior 
Lighting
Lot Features 
Cul-De-SacLandscapedPavedWaterfront
Patio And Porch 
Front PorchRear Porch
Pool Features 
GuniteIn GroundPrivate
Private Pool 
Yes
Roof 
Tile
Spa 
Yes
Spa Features 
In Ground
View 
LakeWater
Waterfront 
Yes
Waterfront Features 
Lake Front
Waterview 
LakeWater
Windows/Doors 
Window CoveringsBlindsDrapesWindow Treatments
Community Features
Association Amenities 
ClubhouseFitness CenterGatedPoolRecreation FacilitiesSecurityTennis Court(s)
Association Dues 
5700
Community Features 
GatedClubhouseFitness CenterGolfPoolTennis Court(s)Street Lights
Financing Terms Available 
CashConventional
HOA Fee Frequency 
Semi-Annually
MLS Area 
34229 - Osprey
Roads 
AsphaltPaved
Township 
38
Schools
School District
Unknown
Elementary School
Laurel Nokomis Elementary
Middle School
Sarasota Middle
High School
Venice Senior High
Listing courtesy of DOUGLAS ELLIMAN 9415874894



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2025, Stellar MLS.
Last checked: 2025-10-14 12:00 AM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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