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$2,000,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 3,288 Sq. Ft.
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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.

Full Property Details for 4 Winslow Pl

General

  • Sold For: $2,000,000
  • HOA FEE: $100/month
  • HOA FEE FREQ.: Annually
  • Taxes: $20,182 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4666470
  • Added to Site: 112 day(s) ago

Rental Information

  • Min. Lease: 1 Month

Interior

  • Number of Rooms: 3
  • Interior Features: Ceiling Fan(s), Dry Bar, Kitchen and Family Room Combination, 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: Convection Oven, Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, Screen Enclosure

Exterior

  • Exterior Features: French Doors, Hurricane Shutters, Lighting
  • Deck/Patio: Deck, Patio, Screened
  • Porch/Patio/Deck: Deck, Patio, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener

Location

  • Area: 34228 - Longboat Key
  • County: Sarasota
  • Development Name: 34228 - Longboat Key
  • Subdivision: BUTTONWOOD HARBOR
  • Driving Directions: Gulf of Mexico Drive to east on Buttonwood Dr, take 1st left, Winslow Place.
  • Direction Faces: Southwest

School Information

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

Community

  • Community Name: 34228 - Longboat Key
  • Community Features: Water Access, Waterfront, Deed Restrictions
  • Association: Yes
  • Assoc. Name: David Bishop, Assn. President
  • Assoc. Fees Include: Private Road

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water District: CRANES BAYOU
  • Water: Public
  • Utility Description: Cable TV Available, Cable Connected, Electricity Connected, Natural Gas Available, Public

Structural Information

  • Architectural Info: Contemporary, Florida
  • Architectural Style: Contemporary, Florida
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Blinds, Drapes, Insulated Windows, Rods
  • Stories/Levels: Two
  • Square Feet: 3,288
  • Sq. Ft. Source: Public Records
  • Living Area: 3,288 Sq. Ft.
  • Year Built: 1963

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.31
  • Lot Size (Sq. Ft.): 13,302
  • Lot Size: 13302
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Bayou, Beach, Intracoastal Waterway
  • Water Extras: Yes
  • Water Front Name: CRANES BAYOU
  • Water Front Desc.: Waterfront, Bayou

Financial Considerations

  • Association Fee: $1,200
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $20,182
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 6 REPLAT UNRECORDED OF A PORTION OF BLKS 8 & 9 LONGBOAT SHORES REVISED
  • Flood Zone Info: AE
  • APN: 5080031
  • Property ID: 5080031
  • Block/Lot/Section: 8

Meet the listing and selling agents

Meet the listing and selling agents
— 4 Winslow Pl —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 4 Winslow Pl

School District:Sarasota County School District
NameGradesDistance
Southside Elementary School, Sarasota, FL
1901 Webber Street, Sarasota, FL 34239
PK-57.4 mi
Booker Middle School
2250 Myrtle Street, Sarasota, FL 34234
6-86.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 4 Winslow Pl

Date
Details
Price
Change
Source
10/15/2025
Sold
$2,000,000
—
MLS
9/26/2025
Listed
$2,000,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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4 Winslow Place, Longboat Key, FL 34228 (MLS# A4666470) is a Single Family property that was sold at $2,000,000 on October 15, 2025. This property was listed by The NEST Group from our Longboat Key Office.Want to learn more about 4 Winslow Place? Do you have questions about finding other Single Family real estate for sale in Longboat Key? You can browse all Longboat Key real estate or contact a Coldwell Banker agent to request more information.