Prepare to be captivated by the charm & character of this stunning Key West style home! This gem is located on one of Dunedin's most sought after, premier streets, a mere 2 BLOCKS FROM MAIN ST., vibrant downtown Dunedin & the scenic PINELLAS TRAIL. This lovely home sits proudly on the well manicured & lushly landscaped, BRICK ROAD in Dunedin's Historic District. Enter the property through the picket fence & trellis, making sure to pause on the FRONT PORCH. Over a century of owners have surely had their morning coffee & evening cocktails on this serene porch! Walking in you will immediately feel the cozy charm enveloping you as you take in the scene. ORIGINAL HARDWOOD FLOORS, wavy glass windows, & the recently exposed, uncovered & repurposed fireplace in the living room will welcome you into the home. The main home w/ so many MODERN TOUCHES that blend seamlessly w/ TIMELESS CHARM in 1523 SF w/ an additional (INCOME EARNING) COTTAGE / GUEST HOUSE offering another 720 SF. Heading to the heart of the home you will find a kitchen w/ updates galore! This GOURMET KITCHEN combines style & functionality for the aspiring chef. To name a few of the kitchen goodies...six burner GAS RANGE w/ hood, DOUBLE OVEN, soft close - top tier solid wood cabinets w/ upgraded cabinet accoutrements. Large, ENCHANTING BREAKFAST ROOM sits off the kitchen - adorned w/ windows all around, & bead board wainscoting & ceiling. The primary bath & closet have been recently remodeled w/ top of the line appointments. Enjoy the split plan of the remaining bedrooms & office. Laundry is located just off the 2 car garage w/ a nice little mudroom area & OFFICE W/ PLENTY OF BUILT-INS. The GUEST HOUSE has a TRANSFERRABLE CONTINUOUS USE PERMIT FOR SHORT TERM RENTALS w/ the City of Dunedin & has had enormous success with Airbnb rentals. This quaint cottage easily sleeps 5 w/ a living room, two bedrooms, a full, recently remodeled bathroom, & laundry. The kitchen has been recently updated w/ new counters, backsplash, appliances & range hood. All that additional family members or guests could possibly need, AND, the COTTAGE COMES FULLY FURNISHED! Moving to the outdoor space - This property boasts an EXPANSIVE OUTDOOR ENTERTAINING SPACE, designed for leisure & enjoyment. Nestled between the cottage & main home is a HEATED, SALT POOL & manicured, lush lawn w/ space to spread out. On the west side of the home is another oasis w/ a large deck (plumbed for your gas grill) & a secluded fire pit area. There is one driveway in the front & another in back, with an additional 4 parking spaces. In addition to the obvious to the eye improvements...ELECTRICAL, PLUMBING, A/C, Interior & Exterior Painting, Insulation, Blinds, Pool Heater & Pump have all been recently updated. All appliances come w/ the home(s), & a whole house GENERAC GENERATOR was added in 2021. Immerse yourself in the vibrant neighborhood, known for its historic homes, lively atmosphere, & community spirit. Enjoy Dunedin's GOLF CART COMMUNITY w/ weekend markets, event Parades, 7 Breweries, Highland Games, Seafood & Art Festivals, The Pinellas Trail, Edgewater Park & Marina(1/3mi), walkable Main St. w/ many wonderful shops and restaurants, & much more! 10 Minutes to Honeymoon Island & a quick drive to Tarpon Springs, Clearwater Beach, Safety Harbor, Clearwater & Tampa International Airports, & home to the Toronto Blue Jays Spring Training (1/2 mi) ! NO FLOOD Insurance required! Schedule your visit today!