3435 WINDING OAKS DRIVE, #18, Longboat Key, FL, 34228 | $949,000

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.

Features

  • Heating: Central, Electric
  • Cooling: Central Air, Humidity Control
  • Levels: 1
  • Amenities: Pool, Vehicle Restrictions
  • Rooms: 10
  • Bedrooms: 2
  • Baths: 2 full / 1 half
  • Laundry: Inside, Laundry Room
  • Complex: WINDING OAKS
  • Year Built: 1988
  • Approx Sq. Feet: 2,555
  • Acreage: 13.84
  • Est. Taxes: $8,565
  • Condo Fee: $6,271 Quarterly
  • View: Golf Course, Water
  • Elem. School: Southside Elementary
  • Middle School: Booker Middle
  • High School: Booker High
  • Pet Policy: Dogs OK, Size Limit, Yes
  • Appliances: Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
  • MLS#: A4680403
  • Days on Market: 83 days
  • Website: https://www.raveis.com
    /eprop/A4680403/3435windingoaksdrive_longboatkey_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is 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. (last updated 5/25/2026 11:32:39 AM)
Listing courtesy of MICHAEL SAUNDERS & COMPANY   Phone: 941-383-7591

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
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Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
  • Offers full-service coverage such as Homeowner's, Auto, Life, Renter's, Flood and Valuable Items
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3435 WINDING OAKS DRIVE, #18, Longboat Key, FL, 34228

$949,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $759,200 $759,200 $759,200
Term 360 months 360 months 180 months
Initial Interest Rate** 6.000% 6.250% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.362% 6.385% 6.223%
Monthly Tax Payment $714 $714 $714
H/O Insurance Payment $92 $92 $92
Initial Principal & Interest Pmt $4,552 $4,675 $6,407
Total Monthly Payment $5,358 $5,481 $7,213

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.