5 Winslow Place, FL
Stellar MLS
1 / 1

$2,495,000

5 Winslow PlaceLongboat Key, FL 34228

Listing updated: November 13, 2026 at 9:54 PM ET

Active
Stellar MLSListing courtesy of Premier Sotheby'S International Realty · Cindy Fischer · MLS #A4712863 · Active · 941-383-2500
4
Beds
4
Baths
2,544
Sq Ft
0.3
Acres
1962
Built
◆Waterfront◆Water access◆Private pool◆In-law suite◆Fireplace◆$981/sqft◆360° tour
Single Family Residence

Property type

1962

Year built

12,895 sqft

Lot size

$981

Price / sq ft

$50/mo

HOA dues

1

Day on market

2

Garage spaces

AE

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

Principal & interest$12,616
Property taxes$1,114
Home insurance (est.)$1,144
HOA dues$50

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

  1. Status: Active
    Nov 12, 2026
  2. Listed$2,495,000
    Nov 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

RoomLevelDimensions
Great RoomFirst15x15
KitchenFirst21x15
Dining RoomFirst18x12
Florida RoomFirst11x11
Primary BedroomFirst18x12
Bedroom 2First13x12
Bedroom 4First13x9
DenSecond15x12

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

High riskFEMA Zone AE

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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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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