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101 Osprey Point Drive

Osprey, FL 34229

4 beds
6 baths
5,087 sqft
~1 acre lot
$1,041 per sqft
1985 build
– on site

One or more photo(s) has been virtually staged. Indulge in the epitome of sophistication and timeless elegance with this magnificent luxury home with 4 bedrooms, 5 full and 1 half bath. Meticulously crafted with unparalleled attention to detail by Bo MacEwen, this residence exemplifies quality and refinement at every turn. From the moment you approach, this home's stately facade and impeccable architectural design command attention. Entering through grand double doors, you're greeted by an impressive foyer, and an inviting floor plan that seamlessly blends classic charm with modern conveniences. The formal living room has a fireplace, an opulent chandelier and French doors. A chef's dream, the kitchen boasts top-of-the-line stainless steel appliances, sleek white cabinetry, and an island, with a small breakfast bar. Add this space to a formal dining room with fireplace, a butler’s pantry and a breakfast nook and you have everything you need for intimate gatherings to grand-scale entertaining. The master suite is a sanctuary of indulgence, featuring a large sitting area, and a spa-like ensuite bathroom with a huge shower. Each additional bedroom and bathroom is large, well-arranged and beautifully appointed. The grounds of this home have been designed for beauty and relaxation. At the heart of the grounds stands a stunning fountain. The sound of flowing water provides a calming soundtrack, enhancing the sense of tranquility. Walk out the back of the house and you will find a sparkling pool, surrounded by a spacious deck, its crystal-clear water reflecting the sunlight. Nearby, a luxurious spa invites you to unwind, with warm, bubbling water cascading gently in a soothing rhythm. Add to all this, continuous improvements and updates, including total renovation of the kitchen, down to the studs, new sub zero and Wolfe appliances, and exterior and interior painting in 2019, refinished hardwood floors in 2020, guest room bath remodels in 20201 and 2025, New Daikin 5 ton HP system in 2022, and master bedroom bath remodel in 2025 and you have found a home that has it all! With every feature meticulously curated and no expense spared, this property stands as a testament to luxury living at its very best. Experience the art of fine living in a residence that is as extraordinary as its next owner. The Oaks Bayside is located on the west side of Tamiami Trail, on the banks of Little Sarasota Bay. Surrounded by Historic Spanish Point and conservation land, it enjoys a tranquil, natural setting. There is a community dock for use by residents; fish, launch a kayak or just sit quietly and watch the daily show of glorious color put on by the evening sunsets. The Oaks Club has two championship golf courses, a driving range, 12 HAR TRU tennis courts (4 lighted), 4 pickleball courts, croquet court, a WellFit center, and 3 onsite restaurants. Club membership is required with homeownership.

Listing courtesy of STELLAR_MLS / COLDWELL BANKER REALTY

Last checked: Checking… • Last updated Mar 25, 2025 •

MLS# A4639897 —

The Building

Year Built:

1985
New Construction:

false
Architectural Style:

Custom
Construction Materials:

Block
Levels:

One
Roof:

Tile
Foundation Details:

Slab
Window Features:

Drapes
Security Features:

Gated Community
Building Area Total:

6841
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Cathedral Ceiling(s)
Flooring:

Brick/Stone
Additional Rooms:

Breakfast Room Separate
Fireplace:

true
Fireplace Features:

Family Room

Room Dimensions

Living Area:

5087
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

Rte. 41/Tamiami Trail S. to Oaks Bayside entrance/Osprey Point Drive. West through guard gate. Follow Osprey Point Dr. to address on right.
Latitude:

27.208167
Longitude:

-82.498008
Coordinates:

-82.498008, 27.208167

The Property

Parcel Number:

0142050008
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size Acres:

0.93
Lot Size Area:

40593
Lot Size SqFt:

40593
Lot Size Units:

Square Feet
Total Acres:

1/2 to less than 1
Zoning:

RSF1
Direction Faces:

West
View:

Water
View:

true
Exterior Features:

French Doors
Water Source:

Public
Road Surface Type:

Paved
Flood Zone Code:

AE X
Flood Zone Panel:

12115C0228G
Additional Parcels:

false
Homestead:

true
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

147
Tax Legal Description:

LOTS 147 & 148, LESS N 30 FT OF LOT 148, TOGETHER WITH BEG AT SE COR OF LOT 148 TH N-6-10-38-W 96.8 FT TH N-87-22-15-E 2 FT TH S-6-10- 38-E 191.63 FT TH S-53-22-30-W 167.57 FT TH NWLY ALG CURVE TO RIGHT 31.71 FT TH N-54-13-02-E 181.65 FT TH N-6-10-38-W 62.54 FT TO POB, OAKS, BEING SAME LANDS AS DESC IN ORI 2022112936
Tax Book Number:

2111-2937
Tax Annual Amount:

12315.48

Beds

Bedrooms Total:

4

Baths

Total Baths:

5.5
Total Baths:

6
Full Baths:

5
Half Baths:

1

The Listing

Virtual Tour URL Unbranded:

https://pix360.com/phototour3/39226/
Special Listing Conditions:

None

Heating & Cooling

Heating:

Electric
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Public
Sewer:

Public Sewer

Appliances

Appliances:

Cooktop
Laundry Features:

Inside

Schools

Elementary School:

Laurel Nokomis Elementary
Middle Or Junior School:

Sarasota Middle
High School:

Venice Senior High

The Community

Subdivision Name:

THE OAKS
Senior Community:

false
Community Features:

Buyer Approval Required
Waterview:

Lake
Waterview:

true
Water Access:

false
Waterfront:

true
Spa:

true
Pool Private:

true
Pool Dimensions:

36x20
Pool Features:

In Ground
Pets Allowed:

Yes
Association Amenities:

Fitness Center
Association:

true
Association Fee:

5700
Association Fee Frequency:

Semi-Annually
Association Fee Includes:

24-Hour Guard
Association Fee Requirement:

Required
Monthly HOA Amount:

950
Amenities Additional Fees:

n/a
Ownership:

Fee Simple
Association Approval Required:

true
Waterfront Feet Total:

150

Parking

Garage:

true
Attached Garage:

true
Garage Spaces:

3
Garage Dimensions:

22x35
Carport:

false
Covered Spaces:

3
Open Parking:

true
Parking Features:

Circular Driveway

Monthly cost estimate

Asking price

$5,300,000

Expense	Monthly cost
Mortgage	$28,379
Taxes	$1,026
Insurance	$1,457
HOA fees	$950
Utilities	$235 See report
Total	$32,047/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
3/23/25 Mar 23, 2025	Listed / Active	STELLAR_MLS	$5,300,000	430.0% (70.8% / YR)
2/26/19 Feb 26, 2019		STELLAR_MLS	$1,000,000

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This house located in Oaks, Osprey, FL 34229 is currently for sale for $5,300,000. 101 Osprey Point Drive is a 5,087 square foot house with 4 beds and 6 baths that has been on Estately for 2 days. 101 Osprey Point Drive is in the Oaks neighborhood of Osprey and has a WalkScore® of 3, making it car-dependent. This house is in the attendance area of Laurel Nokomis School and Venice High School.

Listing Courtesy of: STELLAR_MLS and COLDWELL BANKER REALTY.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.