$2,495,000

5 WINSLOW PLACE, Longboat Key

4

Beds

4

Baths

2,544 ft2

Property Size

A4712863

MLS #

About The Property

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.

Listing updated: 2026-11-13T02:36:35.040Z

Listed by Realtor: Cindy Fischer

Listed by office:  PREMIER SOTHEBY'S INTERNATIONAL REALTY

Source: Stellar MLS

Property Details

Listing Id: A4712863
Price: $2,495,000
Property Size: 2,544 ft2
Property Lot Size: 0 ft2
Rooms: 8
Bedrooms: 4
Bathrooms: 4
Architectural Style: Craftsman, Custom
Association Fee: 600
Association Fee Frequency: Annually
Bathrooms Full: 4
Modification Timestamp: 2026-11-13T02:43:50.628Z
Building Area Total: 3164
Community Features: Bay/Harbor Front, Boat Slip, Canal Front, Dock, Intracoastal Waterway, Marina, Water Access, Waterfront
Construction Materials: Stucco
Cooling: Central Air
CoveredSpaces: 2
DirectionFaces: West
FireplaceFeatures: Electric
Flooring: Porcelain Tile, Hardwood
FoundationDetails: Slab
Furnished: Negotiable
GarageSpaces: 2
Laundry Features: Inside
Levels: Two
List AOR: Sarasota - Manatee
List Agent AOR: Sarasota - Manatee
List Agent Email: cindy.fischer@premiersir.com
List Agent Full Name: Cindy Fischer
List Agent MlsId: 281531449
ListOfficeMlsId: 281521124
List Office Name: PREMIER SOTHEBY'S INTERNATIONAL REALTY
ListOfficePhone: 941-383-2500
Listing Terms: Cash, Conventional
Living Area Source: Public Records
LotSizeArea: 12895
LotSizeSquareFeet: 12895
MLS Area Major: 34228 - Longboat Key
MlsStatus: Active
ModificationTimestamp: 2026-11-13T02:36:35.040Z
OnMarketDate: 2026-11-12
Originating System Name: Stellar MLS
Ownership: Fee Simple
Parcel Number: 0005080030
Parking Features: Garage Door Opener, Oversized
Pets Allowed: Cats OK, Dogs OK
Pool Features: In Ground, Heated, Salt Water, Screen Enclosure
Roof: Other
Sewer: Public Sewer
Spa Features: Heated, In Ground
State Or Province: FL
Status Change Timestamp: 2026-11-12T19:56:59.240Z
Stories Total: 2
Street Name: WINSLOW
Street Number: 5
Street Number Numeric: 5
Street Suffix: PLACE
Tax Annual Amount: 13365
Tax Block: 8
Tax Year: 2026
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sewer Connected, Underground Utilities, Water Connected
View: Water
Water Source: Public
Waterfront Features: Bay/Harbor Front, Canal Front, Waterfront, Bay/Harbor
Window Features: ENERGY STAR Qualified Windows, Window Treatments
Year Built: 1962
Zoning: R4SF
FeedTypes: IDX
Source System Key: 821999857
OriginalEntryTimestamp: 2026-11-12T19:56:59.240Z
OriginalListPrice: 2495000

Amenities and Features

Outdoor Details
Garage Attached
Other Features
Built-in Features
Cathedral Ceiling(s)
Dishwasher
Disposal
Dryer
Has a View
Has Cooling System
Has Fireplace
Has Garage
Has Heating System
Has Pool
Has Waterfront
High Ceilings
Home Owners Association
Irrigation System
Lighting
Microwave
Open Floorplan
Rain Gutters
Range
Range Hood
Refrigerator
Smart Appliance(s)
Solid Wood Cabinets
Spa
Split Bedroom
Vaulted Ceiling(s)
Walk-In Closet(s)
Washer
Window Treatments

Schedule a tour

Sat 14 Nov
Sun 15 Nov
Mon 16 Nov
Tue 17 Nov
Wed 18 Nov
Thu 19 Nov
Fri 20 Nov
Sat 21 Nov
Sun 22 Nov
Mon 23 Nov
In Person
Video Chat
Your information

Map Location

Property Map

Mortgage Calculator

Payment Calculator

$12,792.36
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
  • Private Mortgage Insurance
$ 9,673.61

Image Gallery

Similar Listings

Similar Listings

1640 WALDEMERE STREET, Sarasota
Residential
Active
$5,400,000

1640 WALDEMERE STREET, Sarasota

MLS #
A4701346
Size
5,270 ft2
Beds:
5
Baths:
5.5
mls_logo
206 S WATERWAY DRIVE NW, Port Charlotte
Residential
Active
$825,000

206 S WATERWAY DRIVE NW, Port Charlotte

MLS #
C7529496
Size
2,479 ft2
Beds:
4
Baths:
2
mls_logo
10698 ROYAL CYPRESS WAY, Orlando
Residential
Active
$899,000

10698 ROYAL CYPRESS WAY, Orlando

MLS #
O6443682
Size
2,311 ft2
Beds:
3
Baths:
3
mls_logo

Disclaimer

Property ID - | 910832

All listings featuring of Stellar MLS are provided by Stellar MLS. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by MLS.

©2026 Stellar MLS All rights reserved.

Compare Listings

Janet Richmond
Check Pricing