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$2,495,000

Active

5 Winslow Pl, Longboat Key, FL 34228

4 beds · 4 baths · 2,544 sq ft

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY · MLS# A4712863

Listed today7 views this week

Refreshed from the Stellar MLS feed . This listing’s MLS record last changed .

About this home

Exceptional Waterfront Living on Longboat Key! Discover the perfect blend of coastal elegance, outstanding boating, and relaxed island living in this gorgeously renovated four-bedroom, four-bath residence offering 2,544 square feet of beautifully designed living space. Situated 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 both 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 cooking 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 private 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 most 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. Situated in a fabulous mid-island neighborhood, the home enjoys beach access just steps 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 very 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 own waterfront retreat, this extraordinary residence offers a lifestyle as inviting as its surroundings.

Facts

Property type
Single Family Residence
Year built
1962
Bathrooms
4 full
Living area
2,544 sqft
Lot size
0.3 acres
Waterfront
Yes · 68 ft
Water access
Bay/Harbor, Bayou, Beach, Canal - Saltwater, Gulf/Ocean, Gulf/Ocean to Bay, Intracoastal Waterway, Lagoon
Water view
Yes
Private pool
Yes
Exposure
West
Furnished
Negotiable
Flood zone
AE
CDD
No
55+ community
No
Annual taxes
$13,365/yr
Monthly fees
$50/mo
Listed
Nov 12, 2026
MLS #
A4712863

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Estimate the monthly payment

Estimate by Lasbury Tracy Realty — not a loan offer

Starting figures for 5 WINSLOW PL. Everything below is editable.

AssumptionNot a quoted rate. Ask a lender what you actually qualify for today.

From this listingThe seller's most recent annual tax bill as reported to the MLS. Your bill will differ — Florida reassesses on sale and homestead caps reset.

Editable estimateA placeholder, not a quote. On the Gulf Coast this is the line item most likely to be wrong: premiums swing on roof age, wind mitigation, elevation, and carrier appetite. Get a real quote before you rely on this number.

Starts at $0Deliberately zero until you enter a figure — we will not inflate a payment with a guess. Many homes here need it; the flood zone and the current policy's premium decide the number.

From this listingMonthly association fee as reported to the MLS. Confirm what it includes, and ask about special assessments.

AssumptionNot applied — your down payment is 20% or more.

Estimated total monthly payment

$15,859

$12,616 of that is principal & interest. 20% is taxes, insurance and fees — which is why those inputs matter more here than the rate does.

Principal & interest
$12,616
Property taxes
$1,114
Homeowners insurance
$2,079
Flood insurance
$0
HOA / condo fees
$50
Mortgage insurance (PMI)
$0
Total per month
$15,859

Over the life of the loan

Loan amount
$1,996,000
Down payment
$499,000
Total interest
$2,545,788
Principal + interest paid
$4,541,788
Paid off in
2056

Interest is the exact schedule total for a fixed-rate loan held to term and assumes no extra payments. Taxes, insurance and fees are not included in these lifetime figures because they change every year.

Calculated on this page from the figures above — the calculator sends none of them anywhere, and no lender is quoting you. Only the separate flood & insurance request sends anything: what you type into it, to a Lasbury Tracy agent. Figures are estimates for planning only, not a pre-approval, commitment to lend, or a statement of the taxes and insurance you will actually be charged. Lasbury Tracy Realty Inc. is a real estate brokerage, not a lender or an insurance agent.

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5 Winslow Pl, Longboat Key, FL 34228

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY · MLS# A4712863 · Active

How would you like to see it?
Which day?
What time of day?

In person · Fri, Nov 13 · Morning (9-12)

No account, no obligation. Prefer to talk? (941) 474-5585

Where this home is

Opens on aerial — on this coast the canal, the lot and the neighbours answer more questions than a street grid does.

Similar homes

Listing information is provided in part by Stellar MLS, as distributed by MLS GRID. Based on information submitted to the MLS as of Nov 12, 2026, 8:39 PM (ET). All data is obtained from various sources and may not have been verified by broker or MLS. All information provided is deemed reliable but is not guaranteed and should be independently verified. 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. Some IDX listings have been excluded from this website.

Lasbury Tracy Realty Inc. · [email protected]