3446 ANGLIN DRIVE, Siesta Key, FL, 34242 | $1,595,000

A Rare Weekly Rental Opportunity on Siesta Key!

Attention second homeowners and investors: opportunities like this are exceptionally rare on Siesta Key. Located in coveted Bay Isle, this private pool home is legally zoned for seven-day minimum rentals - a major advantage on an island where most properties require 30-day stays. The result? Strong income potential in one of America’s most in-demand vacation destinations, with average daily rental rates of $613 since 2022.

Offered turnkey furnished, this three-story coastal retreat is ideal as a personal escape, income-producing vacation home, or a blend of both. Just a short golf cart ride to Siesta Key Village and the world-famous Siesta Key Beach—voted #1 in the U. S. , the home is tucked behind lush, professionally landscaped tropical foliage, creating a true sense of privacy and serenity.

A brick-paver driveway winds through the greenery to an oversized two-car garage, providing plenty of room for beach gear, bikes, and toys. Inside, the home is thoughtfully designed with bedrooms and bathrooms spread across three levels, offering exceptional privacy for guests and groups.

The first floor addition (2011) includes a fourth bedroom, third bathroom, and sitting area—expanding the home’s capacity to comfortably accommodate up to 10 guests. The dining area flows seamlessly to a screened porch, perfect for alfresco meals surrounded by palms and tropical breezes.

The entire third floor is dedicated to the owner’s suite, a private sanctuary featuring an en-suite bath and direct access to a secluded sun deck—ideal for morning coffee, sunbathing, or unwinding as the sun sets over Siesta Key.

Outdoor living shines with recent upgrades, including a new putting green, expansive two-story deck with screened enclosure and paneled ceiling (2024), and a 2024 six-passenger street-legal golf cart—included. Additional improvements include a metal roof (2021), new 50-gallon water heater, and updated AC and heat pump.

Whether you’re looking to generate immediate rental income, enjoy a personal island retreat, or both, this property delivers on every level. With its rare weekly rental eligibility, upscale amenities, private tropical setting, and prime Siesta Key location, this is a truly exceptional Gulf Coast opportunity.

Features

  • Rooms: 6
  • Bedrooms: 4
  • Baths: 3 full
  • Laundry: In Garage
  • Style: Key West
  • Year Built: 1981
  • Garage: 2-car Garage Door Opener, Garage Faces Side, Off Street
  • Heating: Heat Pump
  • Cooling: Central Air
  • Approx Sq. Feet: 3,064
  • Acreage: 0.23
  • Est. Taxes: $17,672
  • Lot Desc: CoastalConstruction Control Line, Flood Insurance Required, Landscaped
  • View: Pool, Trees/Woods
  • Elem. School: Phillippi Shores Elementary
  • Middle School: Brookside Middle
  • High School: Sarasota High
  • Pool: Gunite, In Ground, Lighting
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Washer
  • MLS#: A4680766
  • Days on Market: 16 days
  • Website: https://www.raveis.com
    /eprop/A4680766/3446anglindrive_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 2/27/2026 10:17:07 AM)
Listing courtesy of HOUSE MATCH   Phone: 941-213-7028

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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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3446 ANGLIN DRIVE, Siesta Key, FL, 34242

$1,595,000

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 $1,276,000 $1,276,000 $1,276,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.250% 5.750% 5.625%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.069% 5.858% 5.806%
Monthly Tax Payment $1,473 $1,473 $1,473
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $7,046 $7,446 $10,511
Total Monthly Payment $8,644 $9,044 $12,109

* 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.