3435 WINDING OAKS DRIVE UNIT 18, LONGBOAT KEY, FL, 34228
Active156 days on marketListed Feb 26, 2026MLS #A4680403
About this home
3435 WINDING OAKS DRIVE UNIT 18
Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
2,555
Sqft
13.84 ac
Lot size
2
Garage
1988
Year built
One
Levels
$371
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 — not generic estimates.
$6,350 /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
$6,350/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.
vs edgeAI estimate
−27%
$/sqft vs Longboat Key actives
$371 vs $696
Days on market
156 vs 95 typical
Where $371/sqft sits among the 262 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 Longboat Key
Get to know Longboat Key. See the full Longboat Key guide →
LONGBOAT KEY 34228 — neighborhood snapshot
Population
7,512
Median age
71.5
Median income
$143,365
Median home value
$959,200
Avg household
1.8
Households w/ children
51%
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 → $893K
Longboat Key median sold, yr/yr
92.8%
Sale-to-list ratio (12 mo)
112 of 262
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 46% 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 3435 WINDING OAKS DRIVE UNIT 18
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$1,100,000
3427 WINDING OAKS DRIVE UNIT 14 · same community
3 bd · 3 ba · 2,555 sqft · $431/sqft · 36 DOM
Sold · Nov ’25$900,000
3465 WINDING OAKS DRIVE UNIT 33 · same community
3 bd · 3 ba · 2,608 sqft · $345/sqft · 2 DOM
Sold · Jun ’26$758,500
3466 WINDING OAKS DRIVE UNIT 35 · same community
2 bd · 2 ba · 2,039 sqft · $372/sqft · 43 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 3435 WINDING OAKS DRIVE UNIT 18 — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 3435 WINDING OAKS DRIVE UNIT 18 — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
3435 WINDING OAKS DRIVE UNIT 18 FAQs
What would the monthly payment be for 3435 WINDING OAKS DRIVE UNIT 18?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,350/mo — principal and interest, the actual property-tax bill 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.
What are the property taxes on 3435 WINDING OAKS DRIVE UNIT 18?+
The most recent tax bill on record (2025) was $8,565. 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 3435 WINDING OAKS DRIVE UNIT 18?+
The listing reports pets: Dogs OK, Size Limit, 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 $949,000, this home is listed about 1% below the Longboat Key median of $960,000. The market section on this page shows how the area is trending.
Which schools are assigned to 3435 WINDING OAKS DRIVE UNIT 18?+
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
Four things that matter here
01Positioned at the premium end
$949,000 runs 46% above the LONGBOAT KEY 34228 median — but at 2,555 sqft it's also 69% larger than the typical Longboat Key listing.
02Golf Course & Water views
The golf course and water view is part of what you're buying — views hold value independently of the structure.
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.
04The price has already moved
Listed at $1,150,000, now $949,000 — a $201K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of MICHAEL SAUNDERS & COMPANY · Sean Clark. MLS #A4680403.
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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