340 Osprey Point Dr

Osprey, FL 34229

$2,395,000
Price
5
Beds
6,001 Sq. Ft.
$399 / Sq. Ft.
6,001
Sq. Ft.
$399
per Sq. Ft.
PendingVirtual Tour
PendingVirtual Tour
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Description

Under contract-accepting backup offers. Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy. A brand-new roof (2024) crowns this sprawling estate, while a pavered circular driveway leads to a spacious 3-car side-load garage. Stately columns welcome you to...Under contract-accepting backup offers. Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy. A brand-new roof (2024) crowns this sprawling estate, while a pavered circular driveway leads to a spacious 3-car side-load garage. Stately columns welcome you to the grand double-door entry, where you’ll step inside to find gleaming marble floors, soaring ceilings, and plantation shutters that set the stage for timeless sophistication. The thoughtfully designed floor plan includes a private office with built-ins and French doors, and a flexible open space with a dramatic backlit tray ceiling—ideal for a formal dining room, music room, or library. The formal living room features a stunning picture window that brings the outdoors in, along with a cozy fireplace and direct access to the luxurious pool area. The chef’s kitchen is a true showstopper, complete with an aquarium window breakfast nook, expansive breakfast bar, dual sinks, center island, double wall ovens, and a butler’s pantry. It opens seamlessly into the family room, where sliding glass doors, a wood-burning fireplace, wet bar, and built-in desk create a warm and inviting space for everyday living and entertaining. The primary suite is a tranquil retreat with a sunlit sitting area, private access to the pool, and a spa-inspired en suite bath with a walk-in shower and soaking tub that overlook your private tropical paradise. Step outside to your own resort-style oasis, where a sparkling pool, separate spa, travertine deck, and covered patio offer the ultimate in outdoor living. With over 6,000 square feet of living space, this estate features 5 bedrooms, 5 full bathrooms, and 2 half baths, along with two newer A/C systems (2023). As a resident of The Oaks, you’ll have access to The Oaks Club’s world-class amenities, including two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center, and fine dining. Ideally located near top-rated Pine View School, Historic Spanish Point, Casey Key, and Oscar Scherer State Park, this home offers both tranquility and convenience. Don’t miss your chance to own this exceptional estate—schedule your private tour today and experience the luxury of life at The Oaks Bayside.
  1. Listed by Lee Brewer • Brokerage DRE #1030924 • RE/MAX ALLIANCE GROUP
    P: (941)-724-3448 C: (941)-724-3448 lee@leebrewer.com

Property Details for 340 Osprey Point Drive

Architectural Style
Custom
Subdivision Name
OAKS
Township
38
Garage Spaces
3
View
Trees/Woods
Waterfront
Yes
Water View
Creek
Furnished
Unfurnished
LISTING UPDATED: 01/04/2026 10:00 AM

Property Details for 340 Osprey Point Drive

StatusPending
MLS #A4647690
Days on Market273
Taxes$21,513 / year
HOA Fees$1,900 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1998
Lot Size0.78 AC / 34,125 SF
CountySarasota County

Location

Listing Courtesy of RE/MAX ALLIANCE GROUP, Lee Brewer
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Building Information for 340 Osprey Point Drive

Stories-Year Built1998Building Size-Lot Size0.78 AC / 34,125 SF

Payment Calculator

$13,624 per month

30 year fixed, 6.15% Interest

Principal and Interest

$11,673

Property Taxes

$1,793

HOA Dues

$158

The Payment Calculator is for illustrative purposes only.

Property Information for 340 Osprey Point Drive

Summary
Location and General Information
  • Building Area Source: Owner
  • Building Area Total: 7306.0
  • Building Area Units: Square Feet
  • Community Features: Water Access, Waterfront, Buyer Approval Required, Deed Restrictions, Fitness Center, Golf, No Truck/RV/Motorcycle Parking, Pool, Special Community Restrictions, Tennis Court(s)
  • Direction Faces: Southwest
  • Directions: Take Tamiami Trail south to Osprey, continue south to the Oaks Club on the right hand side of the road, Turn right at Osprey Point Road, stop at guard house proceed to the first street turn right, follow past the first stop sign to the house on the right side.
  • Elementary School: Laurel Nokomis Elementary
  • Middle Or Junior School: Laurel Nokomis Middle
  • High School: Venice Senior High
  • Other Equipment: Irrigation Equipment
  • Mls Major Change Type: Pending
  • Major Change Type: Pending
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • SW Subdiv Community Name: Oaks The
  • Unit Number: No
  • Street Number: 340
  • Street Name: OSPREY POINT DR
  • State: FL
  • City: OSPREY
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Includes: 24-Hour Guard, Escrow Reserves Fund, Fidelity Bond, Private Road
  • Association Fee Requirement: Required
  • Association Name: LIGHTHOUSE PROPERTY MGT. / HOPE ROOT
  • Association Phone: 941-460-5560
  • Association: Yes
  • CDD: No
  • Number Of Pets: 3
  • Pet Restrictions: Refer to docs.
  • Pet Size: Extra Large (101+ Lbs.)
  • Tax Book Number: 2111-2937
  • Tax Legal Description: LOT 8 & SLY 1/2 OF LOT 9 DESC AS BEG AT MOST SLY COR OF LOT 9 TH N-43-34-41-W 14.18 FT TH WLY ALG CURVE TO LEFT 63.45 FT TH N-36- 44-16-E 185.66 FT TO MHWL OF NORTH CREEK TH S-55-19-55-E ALG SAID
  • Tax Lot: 8
  • Tax Year: 2024
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Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Cleared, Oversized Lot
  • Parcel Number: 0142030009
  • Total Acreage: 1/2 to less than 1
  • Water Access: Creek
  • Water Access: Yes
  • Water Body Name: NORTH CREEK
  • Water Extras: Bridges - No Fixed Bridges
  • Water Extras: Yes
  • Water: Bridges - No Fixed Bridges
  • Zoning: RE1
  • Living Area: 6001
Property and Assessments
  • Year Built Numeric: 1998
  • Amenities Additional Fees: Membership required. See association docs for details.
  • Flood Zone Code: AE
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 18
  • Public Survey Section: 03
Utilities
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Public, Street Lights, Underground Utilities
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block
  • Exterior Features: Hurricane Shutters, Irrigation System, Outdoor Shower, Sliding Doors
  • Foundation Details: Slab
  • Levels: One
  • Pool Features: Auto Cleaner, Child Safety Fence, Deck, Gunite, In Ground, Screen Enclosure
  • Pool Private: Yes
  • Pool: Private, Community
  • Pool Private: Yes
  • Roof: Tile
  • Security Features: Gated Community, Security Gate, Security System
  • Spa Features: Heated, In Ground
  • Waterfront Features: Waterfront, Creek
  • Waterfront Feet Total: 200
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 5
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer
  • Cooling: Central Air, Zoned
  • Fireplace Features: Gas, Living Room
  • Fireplace: Yes
  • Flooring: Carpet, Ceramic Tile, Marble, Hardwood
  • Heating: Central, Electric, Exhaust Fan
  • Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, Dry Bar, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Owner
  • Living Area Units: Square Feet
  • Room Count: 12.0
  • Water View: Yes
  • Bathrooms Half: 2
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 340 Osprey Point Drive

DateEvent & SourcePriceAppreciation
Jan 3, 2026

Pending

MFRMLS #A4647690

—
Nov 10, 2025

Price Change

MFRMLS #A4647690

$2,395,000—
Apr 5, 2025

Listed (Active)

MFRMLS #A4647690

$2,500,000—
Jan 1, 2024

Sold

MFRMLS #A4579561

$2,200,000—
Dec 28, 2023

Sold (Public Record)

Public Record #1524536432

$2,200,000

-2.2% / yr

Nov 20, 2023

Pending

MFRMLS #A4579561

—
Aug 14, 2023

Listed (Active)

MFRMLS #A4579561

$2,495,000—
Mar 31, 2023

Expired

MFRMLS #A4546275

$2,595,000—
Aug 26, 2022

Listed (Active)

MFRMLS #A4546275

$2,650,000—
May 24, 2022

Sold

MFRMLS #A4531775

$2,280,000—
May 23, 2022

Sold (Public Record)

Public Record #1490508667

$2,280,000

+1.8% / yr

Apr 22, 2022

Pending

MFRMLS #A4531775

—
Apr 14, 2022

Listed (Active)

MFRMLS #A4531775

$2,890,000—
Oct 1, 2021

Withdrawn

MFRMLS #A4207974

$1,250,000—
Jan 29, 2018

Listed (Active)

MFRMLS #A4207974

$1,500,000—
Nov 2, 2017

Withdrawn

MFRMLS #A4146053

$1,449,900—
Feb 16, 2016

Listed (Active)

MFRMLS #A4146053

$1,695,000—
Oct 21, 2002

Sold (Public Record)

Public Record #102570947

$1,595,000—
DateEvent & SourcePrice
01/03/2026

Pending

MFRMLS #A4647690

—
11/10/2025

Price Change

MFRMLS #A4647690

$2,395,000
04/05/2025

Listed (Active)

MFRMLS #A4647690

$2,500,000
01/01/2024

Sold

MFRMLS #A4579561

$2,200,000
12/28/2023

Sold (Public Record)

Public Record #1524536432

$2,200,000

-2.2% / yr

11/20/2023

Pending

MFRMLS #A4579561

—
08/14/2023

Listed (Active)

MFRMLS #A4579561

$2,495,000
03/31/2023

Expired

MFRMLS #A4546275

$2,595,000
08/26/2022

Listed (Active)

MFRMLS #A4546275

$2,650,000
05/24/2022

Sold

MFRMLS #A4531775

$2,280,000
05/23/2022

Sold (Public Record)

Public Record #1490508667

$2,280,000

+1.8% / yr

04/22/2022

Pending

MFRMLS #A4531775

—
04/14/2022

Listed (Active)

MFRMLS #A4531775

$2,890,000
10/01/2021

Withdrawn

MFRMLS #A4207974

$1,250,000
01/29/2018

Listed (Active)

MFRMLS #A4207974

$1,500,000
11/02/2017

Withdrawn

MFRMLS #A4146053

$1,449,900
02/16/2016

Listed (Active)

MFRMLS #A4146053

$1,695,000
10/21/2002

Sold (Public Record)

Public Record #102570947

$1,595,000

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

Public Records for 340 Osprey Point Drive

Taxable ValueLand$385,600Additions$1,344,700Total$1,730,300
Tax Record2025$19,853 ($1,654 / month)
Home Facts
Beds5Baths5.5Total Finished SqFt3,454 SqFtAbove Grade Finished SqFt3,454 SqFtStories2Lot Size34,125 SqFtStyleSingle Family ResidenceYear Built1998Year Renovated2008ZoningRSF1CountySARASOTAAPN0142-03-0009Fireplace TypeHas Fireplace

Schools near 340 Osprey Point Drive

This home is within Sarasota.
Rating
School
Type
Grades
Distance
Laurel Nokomis School
Public - PK to 8
Venice Senior High School
Public - 9 to 12
Pine View School
Public - 2 to 12
Imagine School At Palmer Ranch
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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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 RE/MAX ALLIANCE GROUP, Lee Brewer

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.