4508 WOODSIDE ROAD, Siesta Key, FL, 34242 | $2,450,000

Luxury Waterfront Living Now Priced to Move

Welcome to 4508 Woodside Rd, a true boater’s paradise on Siesta Key offering privacy, deep-water access, and refined coastal living. Positioned on one of the island’s deepest canals, this property provides quick access to the Intracoastal and Sarasota Bay, with 95 feet of waterfront and a 75-foot dock designed for serious boating.

Inside, the home features a fully renovated interior with designer tile flooring, an open-concept layout, and expansive sliding glass doors that seamlessly connect indoor and outdoor living. The chef’s kitchen is equipped with custom cabinetry, a Viking hood system, gas cooktop, and premium appliances, while a temperature-controlled wine cellar adds a true luxury touch.

The primary suite is a private retreat with a spacious layout, oversized walk-in closet, and a spa-style bathroom featuring a glass-enclosed shower and outdoor shower access. Every detail has been thoughtfully designed for comfort and functionality.

Step outside to your own private resort complete with a saltwater pool and spa, lush landscaping, integrated lighting, and a covered pergola with outdoor lounge space, propane fire pit, and TV viewing area. A retractable awning and outdoor wet bar enhance the space, making it ideal for entertaining year-round.

Additional highlights include a 250-gallon propane tank, 14. 5 KW generator, updated HVAC, newer water heater with circulating system, epoxy-finished garage, and hurricane protection features.

Originally introduced at $2, 690, 000, the property has undergone multiple strategic price adjustments and is now positioned to sell, presenting one of the best waterfront opportunities on Siesta Key. With nearby properties trading at significant premiums for land value alone, this offering delivers exceptional value for both end-users and investors.

Also available: luxury yacht (inquire for details).

Features

  • Rooms: 7
  • Bedrooms: 3
  • Baths: 2 full
  • Laundry: Inside
  • Year Built: 1969
  • Garage: 2-car Circular Driveway, Driveway, Ground Level, Off Street
  • Heating: Central
  • Cooling: Central Air
  • Approx Sq. Feet: 2,276
  • Acreage: 0.26
  • Est. Taxes: $7,045
  • Lot Desc: FloodZone, In County, Key Lot, Landscaped, Level, Near Marina, Private
  • View: Trees/Woods, Water
  • Elem. School: Phillippi Shores Elementary
  • Middle School: Brookside Middle
  • High School: Sarasota High
  • Pool: Gunite, Heated, In Ground, Salt Water, Solar Cover
  • Pet Policy: Cats OK, Dogs OK, Yes
  • Appliances: Dishwasher, Electric Water Heater, Range, Range Hood, Refrigerator
  • MLS#: A4674684
  • Days on Market: 115 days
  • Website: https://www.raveis.com
    /eprop/A4674684/4508woodsideroad_siestakey_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 4/5/2026 1:04:55 PM)
Listing courtesy of KELLER WILLIAMS ON THE WATER S   Phone: 941-803-7522

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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

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4508 WOODSIDE ROAD, Siesta Key, FL, 34242

$2,450,000

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 $1,960,000 $1,960,000 $1,960,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.750% 6.125% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.263% 6.259% 6.223%
Monthly Tax Payment $587 $587 $587
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $11,438 $11,909 $16,540
Total Monthly Payment $12,150 $12,621 $17,252

* 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.