313 Lookout Point Dr

Osprey, FL 34229

$5,999,999
Price
4
Beds
5,337 Sq. Ft.
$1,124 / Sq. Ft.
5,337
Sq. Ft.
$1,124
per Sq. Ft.
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Description

Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed...Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.
  1. Listed by Natalie Gutwein • Brokerage DRE #2029530 • MICHAEL SAUNDERS & COMPANY
    P: (941)-993-2660 C: (941)-993-2660 nataliegutwein@michaelsaunders.com
  2. Listed by Madison Brown • Brokerage DRE #2029530 • MICHAEL SAUNDERS & COMPANY
    P: (941)-773-7660 C: (941)-773-7660 madisonjbrown00@gmail.com

Property Details for 313 Lookout Point Drive

Subdivision Name
SOUTHBAY YACHT & RACQUET CLUB
Township
38S
Carport Spaces
1
Garage Spaces
5
View
Water
Waterfront
Yes
Water View
Intracoastal Waterway, Marina
Furnished
Partially
LISTING UPDATED: 04/23/2026 12:10 PM

Property Details for 313 Lookout Point Drive

StatusActive
MLS #A4688995
Days on Market31
Taxes$20,559 / year
HOA Fees$656 / quarter
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2016
Lot Size0.41 AC / 17,967 SF
CountySarasota County
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Location

Listing Courtesy of MICHAEL SAUNDERS & COMPANY, Natalie Gutwein; MICHAEL SAUNDERS & COMPANY, Madison Brown
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Building Information for 313 Lookout Point Drive

Stories2Year Built2016Building Size-Lot Size0.41 AC / 17,967 SF

Payment Calculator

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$32,145 per month

30 year fixed, 6.46% Interest

Principal and Interest

$30,213

Property Taxes

$1,713

HOA Dues

$219

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Property Information for 313 Lookout Point Drive

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 6896.0
  • Building Area Units: Square Feet
  • Community Features: Boat Slip, Dock, Fishing, Intracoastal Waterway, Marina, Water Access, Waterfront
  • Direction Faces: Northeast
  • Directions: Take 41 to Blackburn Point Road. Southbay Yacht & Raquet Club will be on your left, go straight thru first stop sign, take a right on Harbor House Drive, take a right onto Lookout Point Drive and it is the second to last house on your left.
  • Elementary School: Laurel Nokomis Elementary
  • Middle Or Junior School: Laurel Nokomis Middle
  • High School: Venice Senior High
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Road Frontage Type: Street Dead-End, Street Paved
  • Senior Community: No
  • SW Subdiv Community Name: Southbay Yacht & Racquet Club
  • Unit Number: No
  • Street Number: 313
  • Street Name: LOOKOUT POINT
  • Street Suffix: DRIVE
  • State: FL
  • City: OSPREY
Parking
  • Attached Garage: Yes
  • Carport: Yes
  • Garage Dimensions: 32x27
  • Garage: Yes
  • Parking Features: Covered, Driveway, Garage Door Opener, Ground Level, Guest
Taxes and HOA Information
  • Association Fee Requirement: Required
  • Association Name: Southbay Yacht & Racquet Club
  • Association: Yes
  • CDD: No
  • Tax Book Number: 22-27
  • Tax Legal Description: LOT 293 SOUTHBAY YACHT & RACQUET CLUB
  • Tax Lot: 293
  • Tax Year: 2025
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Near Marina, Street Dead-End
  • Parcel Number: 0158020017
  • Total Acreage: 1/4 to less than 1/2
  • Water Access: Intracoastal Waterway
  • Water Access: Yes
  • Water Extras: No Wake Zone
  • Water Extras: Yes
  • Water: No Wake Zone
  • Zoning: RSF2
  • Living Area: 5337
Property and Assessments
  • Year Built Numeric: 2016
  • Flood Zone Code: AE, X
  • Flood Zone Date: 03-27-2024
  • Flood Zone Panel: 12115C0236G
  • Homestead: Yes
  • New Construction: No
  • Property Condition: Completed
  • Public Survey Range: 18E
  • Public Survey Section: 15
Utilities
  • Sewer: Public Sewer
  • Utilities: Street Lights
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Builder Name: John Cannon
  • Construction Materials: Stucco
  • Exterior Features: Balcony, Fire Pit, French Doors, Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors, Storage
  • Foundation Details: Slab, Stem Wall
  • Levels: Two
  • Other Structures: Cabana, Outdoor Kitchen
  • Patio And Porch Features: Front Porch, Patio
  • Pool Features: Chlorine Free, Heated, In Ground, Lighting, Salt Water
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Concrete, Tile
  • Spa Features: Heated, In Ground
  • Spa: Yes
  • Waterfront Features: Waterfront, Intracoastal Waterway, Marina
  • Waterfront Feet Total: 191
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 4
  • Additional Rooms: Attic, Bonus Room, Den/Library/Office, Great Room, Storage Rooms
  • Appliances: Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Gas Water Heater, Ice Maker, Microwave, Refrigerator, Washer, Wine Refrigerator
  • Cooling: Central Air
  • Fireplace Features: Living Room
  • Fireplace: Yes
  • Flooring: Carpet, Ceramic Tile, Hardwood
  • Heating: Central
  • Interior Features: Ceiling Fan(s), Central Vacuum, Crown Molding, Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Thermostat, Walk-In Closet(s), Wet Bar
  • Laundry Features: Laundry Chute, Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 15.0
  • Water View: Yes
  • Bathrooms Half: 1
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 313 Lookout Point Drive

DateEvent & SourcePriceAppreciation
Apr 7, 2026

Listed (Active)

MFRMLS #A4688995

$5,999,999—
Jun 6, 2025

Sold (Public Record)

Public Record #1558956032

$3,525,000

+3.6% / yr

Jan 14, 2005

Sold (Public Record)

Public Record #150142311

$1,700,000

+25.1% / yr

DateEvent & SourcePrice
04/07/2026

Listed (Active)

MFRMLS #A4688995

$5,999,999
06/06/2025

Sold (Public Record)

Public Record #1558956032

$3,525,000

+3.6% / yr

01/14/2005

Sold (Public Record)

Public Record #150142311

$1,700,000

+25.1% / yr

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

Public Records for 313 Lookout Point Drive

Taxable ValueLand-Additions-Total-
Tax Record2025$19,389 ($1,616 / month)
Home Facts
Beds4Baths4.5Total Finished SqFt3,685 SqFtAbove Grade Finished SqFt3,685 SqFtStories2Lot Size17,967 SqFtStyleSingle Family ResidenceYear Built2016ZoningRSF2CountySARASOTAAPN0158-02-0017

Schools near 313 Lookout 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
Island Village Montessori School
Charter - K to 8
Rating
School
Distance
Laurel Nokomis School
PublicPK to 8

Venice Senior High School
Public9 to 12

Pine View School
Public2 to 12

Island Village Montessori School
CharterK 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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More information about 313 Lookout Point Drive, Osprey, FL 34229

313 Lookout Point Drive is a single family home for sale in Osprey, FL 34229. This property was listed for sale on April 7, 2026 by MICHAEL SAUNDERS & COMPANY, it's currently listed at $5,999,999. It has been on the market for a total of 31 days and was last sold on June 6, 2025. This listing's school district is Sarasota. Nearby schools include Laurel Nokomis School, Venice Senior High School and Pine View School. 313 Lookout Point Drive is a 4-bed, 5-bath, 5,337 sqft single family home built in 2016.

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, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of MICHAEL SAUNDERS & COMPANY, Natalie Gutwein; MICHAEL SAUNDERS & COMPANY, Madison Brown

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.