IDX

Listed by Cindy Fischer · Courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY · 941-383-2500 · Agent MLS ID# MFR281531449 · Deemed reliable but not guaranteed. · Listing updated: Nov 14, 2026 · 2:54 AM

Active

5 WINSLOW PL

Longboat Key, Sarasota, FL, 34228

$2,495,000

$981/sqft

4Beds
4Baths
2,544Sq Ft
1962Built
1Days on Market

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.

Facts & Features

MFRA4712863
$2,495,000
Active
4
4
4
0
2,544 sqft
0.3000
1962
Residential
Single Family Residence
Custom, Craftsman

Community Information

5 WINSLOW PL
Buttonwood Harbor
Longboat Key
Sarasota
FL
34228
No

Amenities

N/A
N/A
No
Yes
Yes

Interior

High Ceilings, Open Floorplan, Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s), Solid Wood Cabinets, Cathedral Ceiling(s), Window Treatments, Built-in Features
Central
Central Air
Tile, Wood
Electric
2
Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Range, Range Hood, Smart Appliances

Exterior

Rain Gutters, Lighting
Stucco
Slab
Other
N/A
N/A

School Information

N/A
N/A
N/A

Additional Information

November 12, 2026
1
R4SF
West
No

Mortgage Calculator

$
$
%
Years
Percent per year

This calculator provides estimates for informational purposes only and is not a loan offer, pre-approval, or commitment to lend. Actual rates, payments, and loan terms vary by lender and are subject to credit approval, income/asset verification, and market conditions. Property tax and homeowners insurance shown are estimates and may differ. PMI applies when the down payment is under 20%. For an official Loan Estimate, contact a licensed mortgage lender. PREMIER SOTHEBY'S INTERNATIONAL REALTY is a licensed real estate brokerage, not a mortgage lender. Equal Housing Opportunity.

1 day on market

Listing updated: Nov 14, 2026 · 2:54 AM

Listed by: Cindy Fischer · 941-465-1124—PREMIER SOTHEBY'S INTERNATIONAL REALTY · 941-383-2500

Updated from Real Estate Market Data

Location

AEAhmed ElbatrawyEmpire Network Realty

Get in Touch

You may also like

Similar Properties

Show More
595 BOWSPRIT LN — home for sale

$2,950,000

595 bowsprit ln

4Beds
3Baths
MFRA4710892MLS ID
2,550SqFt

Courtesy of ⁨MICHAEL SAUNDERS & COMPANY⁩

6930 LONGBOAT DR S — home for sale

$2,995,000

6930 longboat dr s

4Beds
5Baths
MFRA4709627MLS ID
2,541SqFt

Courtesy of ⁨PREMIER SOTHEBY'S INTERNATIONAL REALTY⁩

617 ROUNTREE DR — home for sale

$2,150,000

617 rountree dr

3Beds
2Baths
MFRA4692822MLS ID
1,972SqFt

Courtesy of ⁨FINE PROPERTIES⁩