49 Osprey Point Dr

3,953 Sq. Ft.
$632 / Sq. Ft.
3,953
Sq. Ft.
$632
per Sq. Ft.

Description

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and...Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.
  1. Listed by Jonathan Abrams • Brokerage DRE #226676 • MICHAEL SAUNDERS & COMPANY
    P: (941)-232-2868 C: (941)-232-2868 Jonathanabrams@michaelsaunders.com

Property Details for 49 Osprey Point Drive

Architectural Style
Contemporary, Custom
Subdivision Name
OAKS
Township
38S
Garage Spaces
2
Waterfront
Yes
Water View
Lake
LISTING UPDATED: 01/29/2026 12:36 PM

Property Details for 49 Osprey Point Drive

StatusActive
MLS #A4671762
Days on Market103
Taxes$14,206 / year
HOA Fees$5,700 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1989
Lot Size0.40 AC / 17,230 SF
CountySarasota County

Location

Listing Courtesy of MICHAEL SAUNDERS & COMPANY, Jonathan Abrams
Add your commute

Building Information for 49 Osprey Point Drive

Stories1Year Built1989Building Size-Lot Size0.40 AC / 17,230 SF

Payment Calculator

$13,843 per month

30 year fixed, 6.15% Interest

Principal and Interest

$12,185

Property Taxes

$1,184

HOA Dues

$475

The Payment Calculator is for illustrative purposes only.

Property Information for 49 Osprey Point Drive

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 5227.0
  • Building Area Units: Square Feet
  • Community Features: Bay/Harbor Front, Dock, Fishing, Water Access, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Restaurant, Tennis Court(s)
  • Direction Faces: North
  • Directions: From US 41 go South to Osprey Point Drive. West on Osprey point drive, show gate guard your card. 49 Osprey Point is on the right.
  • Elementary School: Laurel Nokomis Elementary
  • Middle Or Junior School: Sarasota Middle
  • High School: Venice Senior High
  • Mls Major Change Type: Price Decrease
  • Listing Service: Full Service
  • Senior Community: No
  • SW Subdiv Community Name: The Oaks
  • Unit Number: No
  • Street Number: 49
  • Street Name: OSPREY POINT
  • Street Suffix: DRIVE
  • State: FL
  • City: OSPREY
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Workshop in Garage
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Requirement: Required
  • Association Name: The Oaks Club
  • Association Phone: 941-966-2161
  • Association: Yes
  • CDD: No
  • Number Of Pets: 3
  • Pet Size: Extra Large (101+ Lbs.)
  • Tax Book Number: 2111-2937
  • Tax Legal Description: LOT 135 OAKS
  • Tax Lot: 135
  • Tax Year: 2024
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Landscaped, Oversized Lot
  • Parcel Number: 0142060007
  • Total Acreage: 1/4 to less than 1/2
  • Water Access: Lake
  • Water Access: Yes
  • Water Extras: Fishing Pier
  • Water Extras: Yes
  • Water: Fishing Pier
  • Zoning: RSF1
  • Living Area: 3953
Property and Assessments
  • Year Built Numeric: 1989
  • Association Amenities: Clubhouse, Fitness Center, Golf Course, Maintenance, Pickleball Court(s), Tennis Court(s)
  • Flood Zone Code: X
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 18E
  • Public Survey Section: 03
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Connected, Electricity Connected, Public, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Concrete, Stucco
  • Exterior Features: Outdoor Shower, Sliding Doors, Storage
  • Foundation Details: Slab
  • Levels: One
  • Patio And Porch Features: Covered, Enclosed, Screened
  • Pool Features: Fiber Optic Lighting, In Ground, Salt Water
  • Pool Private: Yes
  • Pool: Private, Community
  • Pool Private: Yes
  • Roof: Tile
  • Security Features: Gated Community
  • Spa Features: Heated, In Ground, Other
  • Spa: Yes
  • Vegetation: Mature Landscaping
  • Waterfront Features: Bay/Harbor Front, Lake Front
  • Waterfront Feet Total: 0
  • Number Of Stories: 1
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 3
  • Additional Rooms: Formal Living Room Separate
  • Appliances: Dishwasher, Range, Range Hood, Refrigerator
  • Cooling: Central Air, Zoned
  • Fireplace Features: Family Room, Living Room
  • Fireplace: Yes
  • Flooring: Concrete
  • Green Indoor Air Quality: Whole House Vacuum System
  • Heating: Central, Zoned
  • Interior Features: Built-in Features, Ceiling Fan(s), Central Vacuum, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 5.0
  • Water View: Yes
  • Bathrooms Half: 1
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 49 Osprey Point Drive

DateEvent & SourcePriceAppreciation
Jan 29, 2026

Price Change

MFRMLS #A4671762

$2,500,000—
Nov 13, 2025

Listed (Active)

MFRMLS #A4671762

$2,595,000—
Nov 4, 2025

Withdrawn

MFRMLS #A4642364

$2,695,000—
Aug 31, 2025

Expired

MFRMLS #A4642364

$2,695,000—
Jun 11, 2025

Price Change

MFRMLS #A4642364

$2,745,000—
Apr 3, 2025

Price Change

MFRMLS #A4642364

$2,795,000—
Mar 5, 2025

Listed (Active)

MFRMLS #A4642364

$2,995,000—
May 31, 2019

Sold (Public Record)

Public Record #645633871

$800,000—
May 30, 2019

Sold

MFRMLS #A4431344

$800,000—
Apr 17, 2019

Pending

MFRMLS #A4431344

—
Mar 28, 2019

Listed (Active)

MFRMLS #A4431344

$850,000—
DateEvent & SourcePrice
01/29/2026

Price Change

MFRMLS #A4671762

$2,500,000
11/13/2025

Listed (Active)

MFRMLS #A4671762

$2,595,000
11/04/2025

Withdrawn

MFRMLS #A4642364

$2,695,000
08/31/2025

Expired

MFRMLS #A4642364

$2,695,000
06/11/2025

Price Change

MFRMLS #A4642364

$2,745,000
04/03/2025

Price Change

MFRMLS #A4642364

$2,795,000
03/05/2025

Listed (Active)

MFRMLS #A4642364

$2,995,000
05/31/2019

Sold (Public Record)

Public Record #645633871

$800,000
05/30/2019

Sold

MFRMLS #A4431344

$800,000
04/17/2019

Pending

MFRMLS #A4431344

—
03/28/2019

Listed (Active)

MFRMLS #A4431344

$850,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 49 Osprey Point Drive

Taxable ValueLand$488,500Additions$866,400Total$1,354,900
Tax Record2025$13,638 ($1,137 / month)
Home Facts
Beds3Baths3.5Total Finished SqFt3,953 SqFtAbove Grade Finished SqFt3,953 SqFtStories1Lot Size17,230 SqFtStyleSingle Family ResidenceYear Built1989Year Renovated2014ZoningRSF1CountySARASOTAAPN0142-06-0007Fireplace TypeHas Fireplace

Schools near 49 Osprey Point Drive

This home is within Sarasota.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 9 to 12
Public - 2 to 12
Charter - PK to 8
Rating
School
Distance
Laurel Nokomis School
PublicPK to 8

Venice Senior High School
Public9 to 12

Pine View School
Public2 to 12

Imagine School At Palmer Ranch
CharterPK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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49 Osprey Point Drive is a single family home for sale in Osprey, FL 34229. This property was listed for sale on November 13, 2025 by MICHAEL SAUNDERS & COMPANY, it's currently listed at $2,500,000. It has been on the market for a total of 103 days and was last sold on May 31, 2019. This listing's school district is Sarasota. Nearby schools include Laurel Nokomis School, Venice Senior High School and Pine View School. 49 Osprey Point Drive is a 4-bed, 4-bath, 3,953 sqft single family home built in 1989.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of MICHAEL SAUNDERS & COMPANY, Jonathan Abrams

The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.