585 Gunwale Ln

Longboat Key, FL 34228

$4,995,000
Price
3
Beds
4,733 Sq. Ft.
$1,055 / Sq. Ft.
4,733
Sq. Ft.
$1,055
per Sq. Ft.
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Pending
Pending
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Description

Under contract-accepting backup offers. Price reduction of $230,000. NEW PRICE OF $4,995,000 for land value. A rare, full-bayfront offering in the desirable community of Country Club Shores on southern end of Longboat Key. On a .36-acre bayfront parcel with 117 feet on Sarasota Bay and 123 feet on a deepwater canal, this residence is a boater’s paradise. A newer seawall and 58-foot dock (2022) with a 24,000-pound boat lift assure easy access to Sarasota Bay and the Gulf of Mexico. For those who want...Under contract-accepting backup offers. Price reduction of $230,000. NEW PRICE OF $4,995,000 for land value. A rare, full-bayfront offering in the desirable community of Country Club Shores on southern end of Longboat Key. On a .36-acre bayfront parcel with 117 feet on Sarasota Bay and 123 feet on a deepwater canal, this residence is a boater’s paradise. A newer seawall and 58-foot dock (2022) with a 24,000-pound boat lift assure easy access to Sarasota Bay and the Gulf of Mexico. For those who want to design and build their dream home, this property offers a spectacular location. Imagine a custom rooftop deck with breathtaking 360-degree views of the bay, Gulf, and downtown Sarasota. On the bay side, Ghost Island sandbar emerges at low tide, creating a natural haven that attracts abundant wildlife and offers fantastic shelling. It also serves as a natural barrier, providing protection during storms. On the Gulf side, deeded access to an exclusive community beach is just a half-mile away. Whether you’re heading out for a day on the water or popping over to St. Armands Circle for dinner and shopping, this home puts you in the center of it all. The residence spans 4,733 square feet and includes three bedrooms and three-and-a-half baths. A soaring 20-foot ceiling defines the living room, where wall-to-wall built-ins create a refined focal point. The dining room opens to a remodeled kitchen outfitted with Graber wood cabinetry and professional-grade Frigidaire appliances. The primary bedroom is on the second floor, featuring a private bayfront balcony, dual walk-in closets, and an adjoining 270-square-foot bonus room ideal for a home office or wellness retreat. Outdoor amenities include a bayfront pool and spa for enjoying Florida sunsets. Additional highlights include impact-resistant windows and doors, and a two-car garage. This is an opportunity to create something extraordinary. This exceptional property presents a rare opportunity to park your boat in the backyard and join the privileged few who call this well-established neighborhood home. By land or by sea, welcome to your fabulous Florida lifestyle!
  1. Listed by Peter Laughlin • Brokerage DRE #2034955 • PREMIER SOTHEBY'S INTERNATIONAL REALTY
    P: (941)-356-8428 C: (941)-356-8428 peter.laughlin@premiersir.com

Property Details for 585 Gunwale Lane

Subdivision Name
COUNTRY CLUB SHORES SEC 02
Township
36S
Garage Spaces
2
View
City, Water
Waterfront
Yes
Water View
Bay/Harbor - Full
LISTING UPDATED: 02/17/2026 02:58 PM

Property Details for 585 Gunwale Lane

StatusPending
MLS #A4657691
Days on Market230
Taxes$19,596 / year
HOA Fees$100 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1990
Lot Size0.36 AC / 15,696 SF
CountySarasota County
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Location

Listing Courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY, Peter Laughlin
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Building Information for 585 Gunwale Lane

Stories3Year Built1990Building Size-Lot Size0.36 AC / 15,696 SF

Payment Calculator

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$25,986 per month

30 year fixed, 6.15% Interest

Principal and Interest

$24,345

Property Taxes

$1,633

HOA Dues

$8

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Property Information for 585 Gunwale Lane

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 6609.0
  • Building Area Units: Square Feet
  • Community Features: Water Access, Waterfront
  • Direction Faces: Southwest
  • Directions: From Downtown Sarasota, take the John Ringling Causeway headed west to St. Armands/Lido Key. At the St. Armands Circle, take the first exit headed north onto Blvd of the Presidents. Continue on to Gulf of Mexico Drive. Make a right onto Gunwale Lane. The home will be at the end on the left hand side.
  • Elementary School: Southside Elementary
  • Middle Or Junior School: Booker Middle
  • High School: Booker High
  • Mls Major Change Type: Pending
  • Major Change Type: Pending
  • Listing Service: Full Service
  • Senior Community: No
  • SW Subdiv Community Name: Country Club Shores
  • Unit Number: No
  • Street Number: 585
  • Street Name: GUNWALE
  • Street Suffix: LANE
  • State: FL
  • City: LONGBOAT KEY
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage Dimensions: 20x20
  • Garage: Yes
  • Parking Features: Driveway
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Requirement: Required
  • Association Name: Kevin Mulkern
  • Association: Yes
  • CDD: No
  • Tax Block: D
  • Tax Book Number: 17-21
  • Tax Legal Description: LOT 1 BLK D COUNTRY CLUB SHORES UNIT 3 SEC 2
  • Tax Lot: 1
  • Tax Year: 2024
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Corner Lot, Cul-De-Sac, In County, Landscaped, Level, Near Golf Course
  • Lot Size Dimensions: 130 x 123 x 117 x 121
  • Parcel Number: 0010070035
  • Total Acreage: 1/4 to less than 1/2
  • Water Access: Bay/Harbor
  • Water Access: Yes
  • Water Extras: No
  • Zoning: R4SF
  • Living Area: 4733
  • Lot Dimensions: 130 x 123 x 117 x 121
Property and Assessments
  • Year Built Numeric: 1990
  • Flood Zone Code: AE
  • Flood Zone Date: 03-27-2024
  • Flood Zone Panel: 12115C0126G
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 17E
  • Public Survey Section: 21
  • Dock YN: Yes
  • Dock Description: Dock - Composite, Dock w/Electric, Dock w/Water Supply, Fish Cleaning Station
  • Dock Lift Capacity: 24000
  • Dock Dimensions: 3x58
Utilities
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Phone Available, Sewer Connected, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Stucco
  • Exterior Features: Irrigation System, Lighting, Sliding Doors
  • Foundation Details: Stem Wall
  • Levels: Three Or More
  • Patio And Porch Features: Deck, Patio
  • Pool Dimensions: 35x18
  • Pool Features: In Ground, Lighting
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Concrete, Tile
  • Spa Features: In Ground
  • Spa: Yes
  • Vegetation: Trees/Landscaped
  • Waterfront Features: Waterfront, Bay/Harbor, Intracoastal Waterway
  • Waterfront Feet Total: 0
  • Number Of Stories: 3
Interior Features
  • Bedrooms Total: 3
  • Bathrooms Full: 3
  • Additional Rooms: Bonus Room, Den/Library/Office, Loft
  • Appliances: Convection Oven, Cooktop, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine Refrigerator
  • Cooling: Central Air
  • Fireplace: No
  • Flooring: Carpet
  • Heating: Central
  • Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, Dry Bar, Eating Space In Kitchen, Solid Wood Cabinets, Split Bedroom, Walk-In Closet(s)
  • Laundry Features: Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 12.0
  • Water View: Yes
  • Bathrooms Half: 1
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 585 Gunwale Lane

DateEvent & SourcePriceAppreciation
Feb 17, 2026

Pending

MFRMLS #A4657691

—
Feb 9, 2026

Price Change

MFRMLS #A4657691

$4,995,000—
Oct 30, 2025

Price Change

MFRMLS #A4657691

$5,225,000—
Jul 2, 2025

Listed (Active)

MFRMLS #A4657691

$5,425,000—
May 22, 2025

Withdrawn

MFRMLS #A4629742

$5,699,000—
Nov 21, 2024

Listed (Active)

MFRMLS #A4629742

$5,995,000—
Nov 1, 2024

Withdrawn

MFRMLS #A4592372

$6,490,000—
Dec 21, 2023

Listed (Active)

MFRMLS #A4592372

$6,900,000—
DateEvent & SourcePrice
02/17/2026

Pending

MFRMLS #A4657691

—
02/09/2026

Price Change

MFRMLS #A4657691

$4,995,000
10/30/2025

Price Change

MFRMLS #A4657691

$5,225,000
07/02/2025

Listed (Active)

MFRMLS #A4657691

$5,425,000
05/22/2025

Withdrawn

MFRMLS #A4629742

$5,699,000
11/21/2024

Listed (Active)

MFRMLS #A4629742

$5,995,000
11/01/2024

Withdrawn

MFRMLS #A4592372

$6,490,000
12/21/2023

Listed (Active)

MFRMLS #A4592372

$6,900,000

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

Public Records for 585 Gunwale Lane

Taxable ValueLand-Additions-Total-
Tax Record2025$19,300 ($1,608 / month)
Home Facts
Beds3Baths3.5Total Finished SqFt3,028 SqFtAbove Grade Finished SqFt3,028 SqFtStories2Lot Size15,696 SqFtStyleSingle Family ResidenceYear Built1990Year Renovated2005ZoningR4SFCountySARASOTAAPN0010-07-0035

Schools near 585 Gunwale Lane

This home is within Sarasota.
Rating
School
Type
Grades
Distance
Southside Elementary School
Public - K to 5
Booker Middle School
Public - 6 to 8
Sarasota Military Academy
Charter - 6 to 12
Bay Haven School Of Basics Plus
Public - K to 5
Rating
School
Distance
Southside Elementary School
PublicK to 5

Booker Middle School
Public6 to 8

Sarasota Military Academy
Charter6 to 12

Bay Haven School Of Basics Plus
PublicK to 5

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 PREMIER SOTHEBY'S INTERNATIONAL REALTY, Peter Laughlin

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.