560 CHIPPING LN

Exceptional waterfront living meets serious Longboat Key boating in this beautifully updated 4300 sf residence in Country Club Shores. Expansive water views, flexible living spaces and deeded beach access create a home designed for the Florida lifestyle. From the moment you enter, the water takes center stage and you know you're home. Generous living and dining spaces give the interior a sophisticated yet relaxed coastal feel. Inside, enjoy the high ceilings, Italian tile floors and a fireplace - and be transported through the wall of windows to blue waters of your pool and dock. The beautifully appointed kitchen is designed for both entertaining and everyday living with Sub-Zero French-door refrigeration and Wolf double ovens and cooktop, Asko dishwasher, new quartz countertops and a floating island with seating. Separate dining areas provide plenty of room for everything from casual mornings to entertaining a crowd. The primary suite offers a private retreat with a balcony and long-range water views - complete with a spacious bath featuring dual sinks and a walk-in shower. Additional oversized suites both upstairs and downstairs offer flexibility for a study or gym. Even more unique is the home's ability to accommodate extended family and guests. A separate entrance opens to its own living area and full bath, while upstairs are two additional bedrooms, a full bath and private sauna—creating a wonderfully versatile space for guests, multigenerational living or extended stays. Outside is where this property truly distinguishes itself. A generous pavered waterfront deck surrounds the Pebble-finish pool and spa, creating multiple areas for lounging, dining and entertaining. The fenced backyard leads to an impressive boating setup with two boat lifts—approximately 24,000 lbs. and 20,000 lbs.— newer seawall and composite dock plus a fish-cleaning station - making it exceptionally well equipped for the boating enthusiast. You're only four homes from the open waters of Sarasota Bay - providing immediate water access and minutes to the open Gulf. And if beach is more your style - enjoy the neighborhood's deeded access to the Gulf of Mexico- right across the street! Significant improvements add another level of value and peace of mind - including a newer roof (2020), all impact windows and doors, updated seawall and dock infrastructure (including plumbing and electrical service to the dock), extensive paver patio, pool resurfacing, interior and exterior painting, tankless hot water heater, landscaping and gas service ready to go for the next owner. And there's room for the toys with a two-car garage with workshop area and storage. You're only five minutes to vibrant St. Armand's Circle for shopping and dining - and a short drive to downtown Sarasota's cultural and entertainment venues. A special home to enjoy everything that makes Longboat Key living so special.

MLS ID#

MFRA4702902

Price

$3,999,990

Status

Active

Bedrooms

5

Bathrooms

5

Full Baths

5

Half Baths

0

Square Footage

4,315 sqft

Acres

0.2600

Year Built

2003

Type

Residential

Subtype

Single Family Residence

Style

N/A

Address

560 CHIPPING LN

Subdivision

Country Club Shores Sec 02

City

Longboat Key

County

Sarasota

State

FL

Zip Code

34228

Senior Community

No

Amenities

N/A

Parking

N/A

View

No

Waterfront

Yes

Pool

Yes

Interior Features

Ceiling Fans(s), Eat-in Kitchen, Living Room/Dining Room Combo, Solid Wood Cabinets, Stone Counters, Window Treatments, Kitchen/Family Room Combo, PrimaryBedroom Upstairs

Heating

Central

Cooling

Central Air

Flooring

Tile, Hardwood

Fireplace

Living Room, Electric

Stories

2

Appliances

Dishwasher, Disposal, Microwave, Range, Electric Water Heater, Refrigerator, Dryer, Washer, Range Hood, Bar Fridge, Tankless Water Heater

Exterior Features

Rain Gutters, Private Mailbox

Construction

Block, Stucco

Foundation

Slab

Roof

Metal

Fencing

N/A

Lot Features

Paved, Street Dead-End, Sidewalk, Near Golf Course, Near Marina, Landscaped

Elementary

Southside Elementary

Middle

Booker Middle

High

Booker High

Date Listed

September 3, 2026

Days on Market

0

Zoning

R4SF

Direction Faces

North

New Construction

No