CENTURY 21 Edge
$3,999,9905 bd5 ba4,315 sqft$927 /sqft$25,542 /mo all-in ↓

560 CHIPPING LANE, LONGBOAT KEY, FL, 34228

Active19 days on marketListed Sep 3, 2026MLS #A4702902

WaterfrontPrivate poolSingle Family ResidenceCOUNTRY CLUB SHORES SEC 02

Come see it

Upcoming open house

Sun, Sep 27

1:00 PM – 4:00 PM

About this home

560 CHIPPING LANE

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.

Facts & features

The home at a glance

5

Bedrooms

5

Bathrooms

4,315

Sqft

0.26 ac

Lot size

2

Garage

2003

Year built

Two

Levels

$927

Per sqft

Private poolWaterfrontFireplaceWater viewPets allowed

Inside

FlooringEngineered Hardwood · Tile
AppliancesBar Fridge · Dishwasher · Disposal · Dryer · Electric Water Heater · Microwave · Range · Range Hood · Refrigerator · Tankless Water Heater · Washer
InteriorCeiling Fan(s) · Eating Space In Kitchen · Kitchen/Family Room Combo · Living Room/Dining Room Combo · PrimaryBedroom Upstairs · Solid Wood Cabinets · Stone Counters · Window Treatments
LaundryLaundry Room
CoolingCentral Air
HeatingCentral

Outside & construction

RoofMetal
ConstructionBlock · Stucco
FoundationSlab
ViewWater
FacesNorth
ExteriorPrivate Mailbox · Rain Gutters · Sliding Doors

Community & fees

HOA fee$17/mo
Taxes (2025)$27,372/yr
PetsYes
CommunityDeed Restrictions · Golf Carts OK

Utilities & systems

UtilitiesCable Available · Electricity Connected · Natural Gas Connected · Sewer Connected · Underground Utilities · Water Connected
WaterPublic

The numbers

What it really costs

Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.

$25,542 /mo · 10% down Conventional, 30-yr fixed at 6%

Principal & interest$21,584
PMI (est., until 20% equity)$1,500
Property tax — 2025 actual bill$2,281
HOA fee — from the listing$17
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $399,999Loan30-yr fixed at 6%Mortgage insuranceIncludedTaxesActual bill on recordInsuranceFlorida estimate

Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.

These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Run your own numbers

Loan type

FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.

Down payment10% · $399,999
Interest rate6.00%
Loan term

Estimated payment

$25,542/mo

Principal & interest$21,584
PMI (est., until 20% equity)$1,500
Property taxes (actual bill)$2,281
HOA / condo fee$17
Est. insurance$160

Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.

Value check

Is the price right?

The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.

$/sqft vs Longboat Key actives

$927 vs $663

Days on market

19 vs 93 typical

Where $927/sqft sits among the 219 Longboat Key actives

101
52
32 · this home
10
8
16
$357–633$633–909$909–1185$1185–1461$1461–1737$1737+

The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.

Where it sits

Inside Country Club Shores

Get to know Longboat Key. See the full Longboat Key guide →

Country Club Shores — neighborhood snapshot

Population

715

Median age

74

Median income

$136,865

Median home value

$1,525,581

Avg household

2

Households w/ children

5%

For the school run

Sarasota County School District

HighBooker High School★★★★★
ElementarySouthside Elementary School★★★★★
MiddleBooker Middle School★★★★

School assignments and ratings via edgeAI — always verify with the district.

The numbers that matter

The Longboat Key market

Seller’s marketBalanced5.5 months of inventoryBuyer’s market

$820K$1.4M

Longboat Key median sold, yr/yr

93.1%

Sale-to-list ratio (12 mo)

94 of 219

Longboat Key actives have cut their price

Median sold price, Longboat Key, trailing 36 months (3-month rolling) · live MLS data.

This home is listed 587% above the LONGBOAT KEY 34228 median. See the full Longboat Key market guide →

Paper trail

This home's history

Sep 3, 2026Listed at $3,999,990 · 19 days on market since
2003Built · COUNTRY CLUB SHORES SEC 02

Reality check

What actually sold near 560 CHIPPING LANE

Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.

600 WEDGE LANESold · Feb ’26

$8,625,000

600 WEDGE LANE · same community

4 bd · 4.5 ba · 4,338 sqft · $1,988/sqft · 65 DOM

550 YARDARM LANESold · Jul ’26

$3,500,000

550 YARDARM LANE · same community

5 bd · 5.5 ba · 4,281 sqft · $818/sqft · 162 DOM

530 CHIPPING LANESold · Aug ’26

$5,650,000

530 CHIPPING LANE · same community

5 bd · 6 ba · 4,216 sqft · $1,340/sqft · 151 DOM

Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.

Your home team

The pros in your corner

Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.

Bridget McLennon

Your agent

Bridget McLennon

Real Estate Agent · CENTURY 21 Edge

Tours, negotiation, and every question about 560 CHIPPING LANE — start here.

Andrew Acosta

Your lender

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Pre-approval, rates, and the real monthly number for 560 CHIPPING LANE — before you fall in love.

See it in person

Schedule a tour

Live availability from Bridget's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.

Straight answers

560 CHIPPING LANE FAQs

What would the monthly payment be for 560 CHIPPING LANE?+

With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $25,542/mo — principal and interest, the actual property-tax bill, the $17/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.

How much are the HOA fees at 560 CHIPPING LANE?+

The association fee works out to $17 per month. Ask us for the full association documents — they spell out exactly what the fee covers.

What are the property taxes on 560 CHIPPING LANE?+

The most recent tax bill on record (2025) was $27,372. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.

Are pets allowed at 560 CHIPPING LANE?+

The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.

How does the price compare to other homes in Longboat Key?+

At $3,999,990, this home is listed about 321% above the Longboat Key median of $950,000. The market section on this page shows how the area is trending.

Which schools are assigned to 560 CHIPPING LANE?+

Booker High School (high), Southside Elementary School (elementary), Booker Middle School (middle) — Sarasota County School District. Always verify school assignments with the district before relying on them.

The brief

Three things that matter here

01Positioned at the premium end

$3,999,990 runs 587% above the LONGBOAT KEY 34228 median — but at 4,315 sqft it's also nearly 3 times the size of the typical Longboat Key listing.

02Waterfront living

This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.

03Strong assigned schools

Booker High School, Southside Elementary School, Booker Middle School — Southside Elementary School rates 5 of 5. Always verify assignments with the district.

Listing courtesy of COLDWELL BANKER REALTY · Monica Verinder. MLS #A4702902.

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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.

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560 CHIPPING LANE, LONGBOAT KEY, FL — 5 Bed, 5 Bath — $3,999,990 | CENTURY 21 Edge