
560 CHIPPING LANE, LONGBOAT KEY, FL, 34228
Active19 days on marketListed Sep 3, 2026MLS #A4702902
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
Inside
Outside & construction
Community & fees
Utilities & systems
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%
The assumptions
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
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$25,542/mo
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
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
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Longboat Key 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
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.
Sold · Feb ’26$8,625,000
600 WEDGE LANE · same community
4 bd · 4.5 ba · 4,338 sqft · $1,988/sqft · 65 DOM
Sold · Jul ’26$3,500,000
550 YARDARM LANE · same community
5 bd · 5.5 ba · 4,281 sqft · $818/sqft · 162 DOM
Sold · 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.
Your agent
Bridget McLennon
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 560 CHIPPING LANE — start here.

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.
Keep looking
Similar homes nearby
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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