$2,600,000

4 Winslow Place Longboat Key, FL 34228

Estimated payment $16,308/month

Total Views 453
4 Beds
3 Baths
3,288 Sq Ft
$791 Price per Sq Ft

Highlights

  • 65 Feet of Bayou Waterfront
  • White Water Ocean Views
  • Beach Access
  • Southside Elementary School Rated A
  • Dock has access to electricity and water
  • Boat Lift

About This Home

Welcome to an extraordinary coastal retreat in the coveted enclave of Buttonwood Harbor on Longboat Key. Completely renovated and impeccably maintained, this stunning residence offers unobstructed views of Cranes Bayou stretching out to Sarasota Bay—boasting deep sailboat water, direct bay access, and an unmatched setting for waterfront living. Tucked away on a private, tree-lined street, this 3-bedroom, 2-bath home sits on a generous 0.31 acres with an ideal southern exposure and is just two blocks from the white sands of the Gulf of Mexico. Inside, a spacious open-concept floor plan welcomes you with soaring ceilings, walls of glass framing the view, and a sleek chef’s kitchen appointed with top-of-the-line Thermador appliances. Ideal for entertaining, the seamless indoor-outdoor flow makes gatherings effortless and elegant. Each bedroom is generously sized, offering comfort and privacy for family or guests. Peace of mind comes standard with this property, thanks to custom whole-house flood barriers, a brand new 2025 metal roof, a dual-zone HVAC system (Trane & York), and a 24kW whole house generator ready to power your oasis. Recent upgrades include new LG washer/dryer units, a new pool heater, and impact-rated doors and windows throughout. Lounge by the sparkling heated pool or unwind on the expansive patio while taking in the rhythmic sound of sailboats gliding by. A private dock with a 7,500-lb boat lift invites you to launch directly into adventure, making this a true boater’s dream. With a short stroll to beach access and proximity to the shops and dining of Bay Isles Plaza, Harry's, Lazy Lobster, and the world-renowned St. Armands Circle—every day here feels like a resort escape. This is your chance to own a slice of paradise in one of Longboat Key’s most desirable neighborhoods—just minutes from downtown Sarasota’s cultural gems, yet worlds away in tranquility.

Listing Agent

Kaisen Mitchell

COLDWELL BANKER REALTY Brokerage Phone: 941-383-6411 License #3394183 Listed on: 06/10/2025

COLDWELL BANKER REALTY

Co-Listing Agent

Shaun Williams

COLDWELL BANKER REALTY Brokerage Phone: 941-383-6411 License #3398346

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $20,182

Year Built

  • Built in 1963

Lot Details

  • 0.31 Acre Lot
  • 65 Feet of Bayou Waterfront
  • Southwest Facing Home
  • Mature Landscaping
  • Oversized Lot
  • Level Lot
  • Property is zoned R4SF

HOA Fees

  • $100 Monthly HOA Fees

Parking

  • 2 Car Attached Garage
  • Garage Door Opener
  • Driveway

Property Views

  • White Water Ocean
  • Intracoastal
  • Bayou

Home Design

  • Contemporary Architecture
  • Florida Architecture
  • Bi-Level Home
  • Slab Foundation
  • Shingle Roof
  • Block Exterior
  • Stucco

Interior Spaces

  • 3,288 Sq Ft Home
  • Open Floorplan
  • Dry Bar
  • Tray Ceiling
  • Ceiling Fan
  • Insulated Windows
  • Blinds
  • Drapes & Rods
  • French Doors
  • Great Room
  • Family Room Off Kitchen
  • L-Shaped Dining Room
  • Tile Flooring
  • Hurricane or Storm Shutters

Kitchen

  • Breakfast Bar
  • Convection Oven
  • Range
  • Microwave
  • Dishwasher
  • Stone Countertops
  • Solid Wood Cabinet

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Split Bedroom Floorplan
  • Walk-In Closet
  • 3 Full Bathrooms

Laundry

  • Laundry Room
  • Dryer
  • Washer

Pool

  • Screened Pool
  • Gunite Pool
  • Fence Around Pool

Outdoor Features

  • Beach Access
  • Access To Intracoastal Waterway
  • Sailboat Water Access
  • Access To Bayou
  • Seawall
  • Boat Lift
  • Dock has access to electricity and water
  • Dock made with Composite Material
  • Deck
  • Screened Patio
  • Exterior Lighting

Location

  • Flood Zone Lot
  • Flood Insurance May Be Required
  • Property is near public transit

Schools

  • Southside Elementary School
  • Booker Middle School
  • Booker High School

Utilities

  • Central Heating and Cooling System
  • Cable TV Available

Community Details

  • Association fees include private road
  • David Bishop, Assn. President Association
  • Buttonwood Harbor Community
  • Buttonwood Harbor Subdivision
  • The community has rules related to deed restrictions

Listing and Financial Details

Home Details

Home Type

Single Family

Est. Annual Taxes

$20,182

Year Built

Built in 1963

Lot Details

0

HOA Fees

$100 per month

Parking

2

Listing Details

  • HOA Fee Includes: Private Road
  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Architectural Style: Contemporary, Florida
  • Construction Materials: Block, Stucco
  • Fireplace: No
  • Living Area: 3288
  • Lot Size Acres: 0.31
  • New Construction: No
  • Year Built: 1963
  • Building Area Total: 4234
  • Lot Size Sq Ft: 13302
  • Directions to Property: Gulf of Mexico Drive to east on Buttonwood Dr, take 1st left, Winslow Place.
  • Status: Active
  • Co List Office Mls Id: MFR231502433
  • Co List Office Phone: 941-383-6411
  • Ownership: Fee Simple
  • Available for Lease YN: 1
  • Escrow State: FL
  • List Office Head Office Key Nume: 1046393
  • Minimum Lease: 1 Month
  • RATIO Current Price By Calculate: 790.75
  • Total Acreage: 1/4 to less than 1/2
  • Unit Number YN: 0
  • Water Access YN: 1
  • MFR_InLawSuiteYN: 0
  • MFR_DockDescription: Dock - Composite,Dock w/Electric,Dock w/Water Supply,Lift
  • MFR_DockYN: 1
  • MFR_CommunityAssociationWaterFeatures: Water Access,Waterfront
  • Attribution Contact: 941-383-6411
  • Tax Year: 2024
  • Special Features: VirtualTour

Interior Features

  • Living Area Units: Square Feet
  • Flooring: Tile
  • Full Bathrooms: 3
  • Interior Amenities: Ceiling Fans(s), Dry Bar, Kitchen/Family Room Combo, L Dining, Living Room/Dining Room Combo, Open Floorplan, Solid Wood Cabinets, Split Bedroom, Stone Counters, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
  • Appliances Included: Convection Oven, Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Foundation Details: Slab
  • Total Bedrooms: 4
  • Levels: Two
  • Spa Yn: No
  • Window Features: Blinds, Drapes, Insulated Windows, Rods
  • Street Number Modifier: 4
  • Living Area Meters: 305.47
  • Room Count: 3

Exterior Features

  • Direction Faces: Southwest
  • Pool Features: Gunite, Heated, Screen Enclosure
  • Exterior Features: French Doors, Hurricane Shutters, Lighting
  • Roof: Shingle
  • Pool Private: Yes
  • View: Water
  • Water Body Name: CRANES BAYOU
  • Waterfront: Yes
  • Patio and Porch Features: Deck, Patio, Screened
  • Road Surface Type: Paved
  • Water Access: Bayou,Beach,Intracoastal Waterway
  • Water Extras: Lift,Sailboat Water,Seawall - Concrete
  • Water Extras YN: 1
  • Water View: Bay/Harbor - Full,Bayou,Intracoastal Waterway
  • Water View YN: 1
  • Waterfront Feet Total: 65
  • Flood Zone Date: 2016-11-04
  • Flood Zone Panel: 12115C0107F
  • Water Frontage Feet Bayou: 65

Garage/Parking

  • Attached Garage: Yes
  • Carport Y N: No
  • Garage Spaces: 2
  • Garage Yn: Yes
  • Parking Features: Driveway, Garage Door Opener

Utilities

  • Utilities: Cable Available, Cable Connected, Electricity Connected, Natural Gas Available, Public
  • Cooling: Central Air
  • Heating: Central
  • Laundry Features: Inside, Laundry Room
  • Sewer: Public Sewer
  • Water Source: Public

Condo/Co-op/Association

  • Community Features: Deed Restrictions
  • Association Fee: 1200
  • Association Fee Frequency: Annually
  • Association Name: David Bishop, Assn. President
  • Association: Yes
  • Senior Community: No
  • Association 2 YN: 0
  • Association Approval Required YN: 0
  • Association Fee Requirement: Required

Fee Information

  • Total Annual Fees: 1200.00
  • Total Monthly Fees: 100.00
  • Monthly HOA Amount: 100.00

Schools

  • Elementary School: Southside Elementary
  • High School: Booker High
  • Middle Or Junior School: Booker Middle

Lot Info

  • Zoning: R4SF
  • Parcel Number: 0005080031
  • Additional Parcels: No
  • Lot Features: CoastalConstruction Control Line, Flood Insurance Required, FloodZone, City Limits, In County, Level, Near Public Transit, Oversized Lot, Paved
  • Flood Zone Code: AE
  • Homestead YN: 0
  • Lot Size Square Meters: 1236
  • Zoning Compatible YN: 1

Rental Info

  • Furnished: Unfurnished
  • Pets Allowed: Yes
  • Lease Restrictions YN: 1
  • Additional Lease Restrictions: Per Longboat Key ordinance - minimum 30 days.

Tax Info

  • Tax Annual Amount: 20182
  • Tax Block: 8
  • Tax Lot: 6

Multi Family

  • Waterfront Features: Bayou

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2024 $19,003 $1,298,377 -- --
2023 $19,003 $1,634,700 $1,112,600 $522,100
2022 $17,462 $1,470,000 $1,043,600 $426,400
2021 $14,413 $991,400 $694,300 $297,100
2020 $13,025 $863,900 $589,700 $274,200
2019 $12,125 $807,800 $551,100 $256,700
2018 $13,499 $903,300 $626,000 $277,300
2017 $12,983 $878,339 $0 $0
2016 $12,339 $863,100 $547,000 $316,100
2015 $10,882 $725,900 $439,800 $286,100
2014 $6,050 $431,106 $0 $0
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
06/10/2025 06/10/25 For Sale $2,600,000 +141.9% $791 / Sq Ft
05/08/2019 05/08/19 Sold $1,075,000 -6.5% $544 / Sq Ft
04/05/2019 04/05/19 Pending -- -- --
04/01/2019 04/01/19 For Sale $1,150,000 +7.0% $582 / Sq Ft
02/01/2019 02/01/19 Off Market $1,075,000 -- --
12/03/2018 12/03/18 For Sale $1,150,000 +21.1% $582 / Sq Ft
06/13/2014 06/13/14 Sold $950,000 -4.9% $481 / Sq Ft
04/21/2014 04/21/14 Pending -- -- --
03/10/2014 03/10/14 Price Changed $999,000 -8.8% $506 / Sq Ft
12/10/2013 12/10/13 For Sale $1,095,000 -- $554 / Sq Ft
Source: Stellar MLS

Purchase History

Date Type Sale Price Title Company
Warranty Deed $1,075,000 Barnes Walker Title Inc
Warranty Deed $900,000 Attorney
Warranty Deed $770,500 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $100,000 Credit Line Revolving
Source: Public Records

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Source: Stellar MLS

MLS Number: A4655347

Stellar MLS

APN: 0005-08-0031