Michael Saunders & Company logo
Michael Saunders & Company logo

Search Homes

3435 Winding Oaks Drive, Unit 18Longboat Key, FL 34228Price: $1,050,000

  • Price: $1,050,000
  • Est. Mortgage of $/month
  • 83 Days on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Request More Info

  • $1,050,000List Price
  • ActiveStatus
  • 85Number of Photos
  • 27.377941Latitude
  • 3435 Winding Oaks DriveAddress
  • Winding Oaks DriveStreet
  • 18Unit Number
  • Longboat KeyTown
  • FLState
  • 34228Zip
  • SarasotaCounty
  • ResidentialProperty Type
  • A4680403MLS Number
  • 2Bedrooms
  • 2Full Bath
  • 1Half Baths
  • 2,555Square Feet
  • 1988Year Built
  • 13.84Acreage

Listing Tools

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.

Location

LISTING COURTESY OF Sean Clark of MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of May 19, 2026 5:37 PM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

By submitting this form I agree to receive marketing and customer service calls and text messages from Michael Saunders & Company. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Property Details of 3435 Winding Oaks Drive, Unit 18

Property Details

Interior Features

Utilities and Appliances

Community

Estimate Your Payment

Monthly Payment (excluding insurance*) $0.00

Principal & Interest $0.00

Property Tax $0.00

(Payments are an estimate and may vary by lender.)

*For an insurance quote on this property, please contact the Baldwin Group.

Mortgage Calculator

Change Payment Information

$
$
=
%
%
$
Image

Committed to making your mortgage application simple and smooth, MSC Mortgage provides a full range of financing options. Whether buying or refinancing a home, our goal is to choose the loan that is best tailored to your individual needs and provide outstanding customer service. Already have a pre-approval? Our mortgage experts will review it for free to explore potential opportunities for improvement or better terms.

Image

Work with Megan Kendrick

Mortgage Loan Officer

Lifestyle

Demographics

Open one door for all your real estate needs.

When you work with Michael Saunders & Company agents, they will connect you with a team of in-house experts in our mortgage, insurance and title divisions, ensuring a seamless full homeownership experience from start to finish.

MSCMortgage

Providing a full range of financing options.

Get Started
MSCTitle logo

Ensuring a clear path to closing.

Get Started
The Baldwin Group logo

Protecting your investment with comprehensive coverage.

Get Started

Let’s Get in Touch

To schedule a showing or learn more information about this listing, please call or send a message.

Do not fill in this field:

By submitting this form I agree to receive marketing and customer service calls and text messages from Michael Saunders & Company. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.