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 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.
Sold for $2,000,000
$2,000,000
4 Winslow Pl, Longboat Key, FL 34228
4beds
3,288sqft
Single Family Residence
Built in 1963
0.31 Acres Lot
$1,956,200 Zestimate®
$608/sqft
$7,290 Estimated rent
Home value
$1,956,200
$1.78M - $2.15M
$7,290/mo
Zestimate® history
Owner options
List your home for rent
$7,290/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$7,290/mo
Rent Zestimate®
Refinance and save
$12,837/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$12,837/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked:
Listing updated:
Listing Provided by:
Kaisen Mitchell 941-726-7657,
COLDWELL BANKER REALTY 941-383-6411
Bought with:
Kerry McCarthy, 3579334
COLDWELL BANKER REALTY
Source: Stellar MLS,MLS#: A4666470
Originating MLS: Sarasota - Manatee
Originating MLS: Sarasota - Manatee
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Features: Ceiling Fan(s), Walk-In Closet(s)
- Level: First
- Area: 224 Square Feet
- Dimensions: 16x14
Great room
- Features: Ceiling Fan(s)
- Level: First
- Area: 660 Square Feet
- Dimensions: 33x20
Kitchen
- Features: Breakfast Bar, Ceiling Fan(s), Kitchen Island, Other
- Level: First
- Area: 160 Square Feet
- Dimensions: 16x10
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Convection Oven, Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Laundry: Inside, Laundry Room
Features
- Ceiling Fan(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)
- Flooring: Tile
- Doors: French Doors
- Windows: Blinds, Drapes, Insulated Windows, Rods, Window Treatments, Hurricane Shutters
- Has fireplace: No
Interior area
- Total structure area: 4,234
- Total interior livable area: 3,288 sqft
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Garage Door Opener
- Attached garage spaces: 2
- Has uncovered spaces: Yes
- Details: Garage Dimensions: 20x30
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Patio, Screened
- Exterior features: Lighting
- Has private pool: Yes
- Pool features: Gunite, Screen Enclosure
- Has view: Yes
- View description: Water, Bay/Harbor - Full, Bayou, Intracoastal Waterway
- Has water view: Yes
- Water view: Water,Bay/Harbor - Full,Bayou,Intracoastal Waterway
- Waterfront features: Waterfront, Bayou, Bayou Access, Beach Access, Intracoastal Waterway Access, Lift, Sailboat Water, Seawall
- Body of water: CRANES BAYOU
Lot
- Size: 0.31 Acres
- Features: CoastalConstruction Control Line, Flood Insurance Required, FloodZone, City Lot, In County, Level, Near Public Transit, Oversized Lot
- Residential vegetation: Mature Landscaping
Details
- Parcel number: 0005080031
- Zoning: R4SF
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary,Florida
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1963
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available, Cable Connected, Electricity Connected, Natural Gas Available, Public
Community & neighborhood
Community
- Community features: Water Access, Waterfront, Deed Restrictions
Location
- Region: Longboat Key
- Subdivision: BUTTONWOOD HARBOR
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $100 monthly
- Services included: Private Road
- Association name: David Bishop, Assn. President
Other fees
- Pet fee: $0 monthly
Other financial information
- Total actual rent: 0
Other
Other facts
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 10/15/2025 | Sold | $2,000,000$608/sqft |
Source:  Stellar MLS #A4666470 Report a problem | ||
| 9/26/2025 | Pending sale | $2,000,000-23.1%$608/sqft |
Source: Stellar MLS #A4666470 Report a problem | ||
| 8/18/2025 | Listing removed | $2,600,000$791/sqft |
Source: Stellar MLS #A4655347 Report a problem | ||
| 6/10/2025 | Listed for sale | $2,600,000+141.9%$791/sqft |
Source: Stellar MLS #A4655347 Report a problem | ||
| 5/9/2019 | Sold | $1,075,000-6.5%$327/sqft |
Source: Public Record Report a problem | ||
| 4/8/2019 | Pending sale | $1,150,000$350/sqft |
Source: Michael Saunders & Company - Licensed Real Estate Broker #A4420620 Report a problem | ||
| 4/1/2019 | Listed for sale | $1,150,000$350/sqft |
Source: MICHAEL SAUNDERS & COMPANY #A4420620 Report a problem | ||
| 3/31/2019 | Listing removed | $12,500$4/sqft |
Source: JENNETTE PROPERTIES INC #A4104913 Report a problem | ||
| 2/1/2019 | Listed for rent | $12,500$4/sqft |
Source: JENNETTE PROPERTIES INC #A4104913 Report a problem | ||
| 2/1/2019 | Listing removed | $1,150,000$350/sqft |
Source: Michael Saunders & Company - Licensed Real Estate Broker #A4420620 Report a problem | ||
| 12/3/2018 | Listing removed | $12,500$4/sqft |
Source: JENNETTE PROPERTIES INC #A4104913 Report a problem | ||
| 12/3/2018 | Listed for sale | $1,150,000+27.8%$350/sqft |
Source: Michael Saunders & Company - Licensed Real Estate Broker #A4420620 Report a problem | ||
| 4/24/2017 | Listed for rent | $12,500-10.7%$4/sqft |
Source: JENNETTE PROPERTIES INC #A4104913 Report a problem | ||
| 3/24/2016 | Listing removed | $14,000$4/sqft |
Source: JENNETTE PROPERTIES INC #A4104913 Report a problem | ||
| 9/17/2014 | Listed for rent | $14,000$4/sqft |
Source: JENNETTE PROPERTIES INC #A4104913 Report a problem | ||
| 6/13/2014 | Sold | $900,000-9.9%$274/sqft |
Source: Public Record Report a problem | ||
| 6/9/2014 | Listed for sale | $999,000$304/sqft |
Source: COLDWELL BANKER RES R E #A3989179 Report a problem | ||
| 4/23/2014 | Listing removed | $999,000$304/sqft |
Source: Coldwell Banker Residential Real Estate - Longboat Key #A3989179 Report a problem | ||
| 3/11/2014 | Price change | $999,000-8.8%$304/sqft |
Source: Coldwell Banker Residential Real Estate - Longboat Key #A3989179 Report a problem | ||
| 12/11/2013 | Listed for sale | $1,095,000+42.1%$333/sqft |
Source: Coldwell Banker Residential Real Estate - Longboat Key #A3989179 Report a problem | ||
| 2/2/2004 | Sold | $770,500$234/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $20,991 +4% | $1,414,685 +9% |
| 2024 | $20,182 +6.2% | $1,298,377 +10% |
| 2023 | $19,003 +8.8% | $1,180,343 +10% |
| 2022 | $17,462 +21.2% | $1,073,039 +10% |
| 2021 | $14,413 +10.7% | $975,490 +12.9% |
| 2020 | $13,025 +7.4% | $863,900 +6.9% |
| 2019 | $12,125 | $807,800 -10.6% |
| 2018 | $12,125 -10.2% | $903,300 +2.8% |
| 2017 | $13,499 +24.1% | $878,339 +1.8% |
| 2016 | $10,882 | $863,100 +18.9% |
| 2015 | $10,882 +79.9% | $725,900 +68.4% |
| 2014 | $6,050 +2.3% | $431,106 |
| 2013 | $5,916 +4.2% | $431,106 +1.7% |
| 2012 | $5,680 -1.6% | $423,900 -2.8% |
| 2011 | $5,771 -1.1% | $436,247 +1.5% |
| 2010 | $5,837 -27.1% | $429,800 -15.6% |
| 2009 | $8,010 | $509,200 -13.6% |
| 2008 | $8,010 -5.5% | $589,200 -5.3% |
| 2007 | $8,472 | $622,400 -0.1% |
| 2006 | -- | $623,100 +27.6% |
| 2005 | -- | $488,300 +8.7% |
| 2004 | $7,085 +4.9% | $449,400 +10.3% |
| 2003 | $6,757 +6.3% | $407,400 +10.6% |
| 2002 | $6,357 +23.7% | $368,300 +19.1% |
| 2001 | $5,137 +13.3% | $309,200 +15.3% |
| 2000 | $4,535 | $268,100 |
Find assessor info on the county website
Neighborhood: 34228
Nearby schools
GreatSchools rating
- 10/10Southside Elementary SchoolGrades: K-5Distance: 7.4 mi
- 5/10Booker Middle SchoolGrades: 6-8Distance: 6.5 mi
- 3/10Booker High SchoolGrades: 9-12Distance: 5.6 mi
Schools provided by the listing agent
- Elementary: Southside Elementary
- Middle: Booker Middle
- High: Booker High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,956,200
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,956,200
- Florida
- Sarasota County
- Longboat Key
- 34228
- 4 Winslow Pl
Nearby cities
Nearby zip codes
Other Longboat Key Topics
