
$2,495,000
5 Winslow PlaceLongboat Key, FL 34228
Listing updated: November 13, 2026 at 9:54 PM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Day on market
Garage spaces
Flood zone
About this home
Exceptional waterfront living on Longboat Key! Discover the ideal blend of coastal elegance, outstanding boating, stunning beaches and relaxed island living in this gorgeously renovated four-bedroom, four-bath residence offering 2,544 square feet of beautifully designed living space. Along a tranquil, protected bayou with expansive water views, this exceptional home captures the essence of the Longboat Key lifestyle. From the moment you enter, the home's flowing, open floor plan and thoughtfully designed living spaces create an inviting atmosphere, with spectacular water views from virtually every room. Beautifully renovated interiors combine sophisticated finishes with comfortable, effortless living. Designed with the chef in mind, the stunning kitchen is a culinary showpiece and a natural gathering place. An oversized center island with a convenient prep sink provides exceptional workspace while inviting casual conversation and entertaining. Gorgeous quartz countertops, including a dramatic waterfall island design, complement the high-end appliance suite featuring Bosch appliances. The kitchen flows seamlessly into the home's open living and dining areas, where expansive views of the pool and bayou provide a beautiful backdrop for everyday living and entertaining. The thoughtfully designed bedroom arrangement offers exceptional privacy and flexibility. The private primary suite features a spacious walk-in closet and beautifully appointed en-suite bath. A generous guest suite offers a large bedroom, separate den and beautifully designed custom bath, creating an ideal retreat for visiting family and friends. Two additional bedrooms, one with an en-suite bath and the other with an adjoining full bath, provide comfortable accommodations for family and guests. Outdoor living is equally spectacular. Surrounded by professionally designed tropical landscaping, the gorgeous custom, free-flowing heated pool and spa create a private resort-like setting overlooking the peaceful bayou. An easy-care saltwater system enhances the enjoyment of this exceptional outdoor retreat. For boating enthusiasts, the property is particularly appealing. A new composite dock, well-protected sailboat-depth water, and direct boating access to Sarasota Bay and the Gulf provide an outstanding opportunity to explore some of Southwest Florida's beautiful waterways. Additional features include hurricane-impact windows and doors throughout, a newer roof, natural gas, an on-demand hot water heater, a welcoming circular driveway, and a garage featuring epoxy flooring and additional storage. The location is simply outstanding. In a fabulous mid-island neighborhood, the home enjoys beach access just a stone’s throw away, offering the rare opportunity to spend mornings on the Gulf's beautiful beaches and afternoons cruising the waters of Sarasota Bay. Nearby shopping, restaurants, the Town Green, and amphitheater add to the convenience and charm of this exceptional island setting. Beautifully renovated, thoughtfully designed and surrounded by the natural beauty of its tranquil waterfront setting, 5 Winslow Place offers an exceptional opportunity to experience the best of Longboat Key living. Whether your passion is boating, enjoying the Gulf's beautiful beaches, entertaining family and friends, or simply relaxing in the privacy of your waterfront retreat, this extraordinary residence offers a lifestyle as inviting as its surroundings.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history1 days on market
- Status: ActiveNov 12, 2026
- Listed$2,495,000Nov 12, 2026
Property Documents
Documents the listing agent has made public for this property. Free to view and download.
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 1
- Subdivision
- Buttonwood Harbor
- County
- Sarasota
- Year built
- 1962
- Living area
- 2,544 sq ft
- Price/sq ft
- $981
- Building area
- 3,164 sq ft (Public Records)
- Lot size
- 12,895 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- AE
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $13,365 (2026)
- Parcel #
- 0005080030
- Zoning
- R4SF
- MLS #
- A4712863
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 4
- Flooring
- Tile, Wood
- Appliances
- Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Smart Appliances, Washer
- Interior features
- Built-in Features, Cathedral Ceiling(s), High Ceilings, Open Floorplan, Solid Wood Cabinets, Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
- Laundry
- Inside
- Stories / Levels
- Two
- Direction faces
- West
- Fireplace
- Yes
- In-law suite
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Garage Door Opener, Oversized
HOA & Financial
- HOA fee
- $600 / Annually
- Monthly HOA
- $50/mo
- Total monthly fees
- $50/mo
- Total annual fees
- $600
- HOA name
- Matthew Pifer, HOA President
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 1 Month
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
Exterior & Construction
- Exterior features
- Lighting, Rain Gutters
- Construction materials
- Stucco
- Roof
- Other
- Foundation
- Slab
- Pool
- Private pool
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sewer Connected, Underground Utilities, Water Connected
Community
- Pets allowed
- Cats OK, Dogs OK
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Great Room | First | 15x15 |
| Kitchen | First | 21x15 |
| Dining Room | First | 18x12 |
| Florida Room | First | 11x11 |
| Primary Bedroom | First | 18x12 |
| Bedroom 2 | First | 13x12 |
| Bedroom 4 | First | 13x9 |
| Den | Second | 15x12 |
Listing Details
- Listing date
- 2026-11-12
- On market date
- 2026-11-12
- Original list price
- $2,495,000
- Occupant type
- Owner
- MLS area
- 34228 - Longboat Key
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-11-12
- Tax legal description
- BEG AT SE COR OF NE 1/4 OF NE 1/4 OF SEC 7-36-17 TH N 192 FT TO THE N R/W OF BUTTONWOOD DR TH W ALG R/W 825.66 FT TO TH W LINE OF A 20 FT PVT RD TH N ALG W LINE 160 FT TH N-75-13-23-W ALG S LINE OF
Flood risk
FEMA Special Flood Hazard Area (1% annual-chance / “100-year” floodplain). Flood insurance is generally required by mortgage lenders.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
Gulf of Mexico Dr to Buttonwood Harbour then first left onto Winslow. Will be fourth house with a circular driveway.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
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Based on information submitted to the MLS GRID as of November 13, 2026 at 9:54 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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