Seller's Agent in 2025
Kaisen Mitchell
COLDWELL BANKER REALTY
(941) 726-7657
10 in this area
174 Total Sales
4 Winslow Place Longboat Key, FL 34228
4
Beds
3
Baths
3,288
Sq Ft
0.31
Acres
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
As of October 2025Welcome 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 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.
Last Agent to Sell the Property
COLDWELL BANKER REALTY Brokerage Phone: 941-383-6411 License #3394183 Listed on: 09/26/2025
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
- Visit Down Payment Resource Website
- Legal Lot and Block 6 / 8
- Assessor Parcel Number 0005080031
Ownership History
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Sep 26, 2025
Closed on
Oct 15, 2025
Sold by
Wilson Jason and Wilson Nancy
Bought by
Holloran Jeffrey
Seller's Agent
Kaisen Mitchell
COLDWELL BANKER REALTY
Buyer's Agent
Kerry McCarthy
COLDWELL BANKER REALTY
List Price
$2,000,000
Sold Price
$2,000,000
Views
1
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
36.36%
Purchase Details
Listed on
Dec 3, 2018
Closed on
May 8, 2019
Sold by
Benaddi Omar and Benaddi Janette
Bought by
Wilson Jason and Wilson Nancy
Seller's Agent
Beverly St Hilaire
MICHAEL SAUNDERS & COMPANY
Buyer's Agent
Erin Leathem
ISLAND REAL ESTATE-ANNA MARIA
List Price
$1,150,000
Sold Price
$1,075,000
Premium/Discount to List
-$75,000
-6.52%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
10.12%
Purchase Details
Listed on
Dec 10, 2013
Closed on
Jun 13, 2014
Sold by
Mock Wayne and Mock Anne
Bought by
Benaddi Omar and Benaddi Janette
Seller's Agent
Roger Pettingell
COLDWELL BANKER REALTY
Buyer's Agent
Beverly St Hilaire
MICHAEL SAUNDERS & COMPANY
List Price
$1,095,000
Sold Price
$950,000
Premium/Discount to List
-$145,000
-13.24%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
2.55%
Purchase Details
Closed on
Jan 29, 2004
Sold by
Wood Thomas A
Bought by
Mock Wayne and Mock Anne
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $2,000,000 | None Listed On Document | |
| Warranty Deed | $1,075,000 | Barnes Walker Title Inc | |
| Warranty Deed | $900,000 | Attorney | |
| Warranty Deed | $770,500 | -- | |
| Warranty Deed | $770,500 | -- |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 10/15/2025 10/15/25 | Sold | $2,000,000 | 0.0% | $608 / Sq Ft | |
| 09/26/2025 09/26/25 | Pending | -- | -- | -- | |
| 09/26/2025 09/26/25 | For Sale | $2,000,000 | +86.0% | $608 / Sq Ft | |
| 05/08/2019 05/08/19 | Sold | $1,075,000 | -6.5% | $544 / Sq Ft | View Prior Sale |
| 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 | View Prior Sale |
| 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
Tax History Compared to Growth
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 |
|---|---|---|---|---|
| 2025 | $20,182 | $1,414,685 | -- | -- |
| 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
Agents Affiliated with this Home
-
Kaisen Mitchell
-
Kerry McCarthy
K
Buyer's Agent in 2025
Kerry McCarthy
COLDWELL BANKER REALTY
(720) 233-7147
2 in this area
5 Total Sales
-
Beverly St Hilaire
Seller's Agent in 2019
Beverly St Hilaire
Michael Saunders
(818) 416-2505
35 in this area
66 Total Sales
-
Erin Leathem
Buyer's Agent in 2019
Erin Leathem
ISLAND REAL ESTATE-ANNA MARIA
(941) 448-5616
5 in this area
100 Total Sales
-
Kathleen White
Buyer Co-Listing Agent in 2019
Kathleen White
ISLAND REAL ESTATE-ANNA MARIA
(941) 773-0165
1 in this area
55 Total Sales
-
Roger Pettingell
Seller's Agent in 2014
Roger Pettingell
COLDWELL BANKER REALTY
(941) 387-1840
152 in this area
340 Total Sales
Map
Source: Stellar MLS
MLS Number: A4666470
APN: 0005-08-0031
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Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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