Elegant and sophisticated aptly describes this pristine 1927 Historic Landmark pool home with a Carriage House situated on over a 1/4 acre lot in the highly sought after Downtown Dunedin golf cart friendly Fenway on the Bay neighborhood. This stylish home is for the discerning buyer with every attention to detail being addressed. Built in the same era, and within walking distance of the iconic Fenway Hotel, this home has been meticulously renovated with high end modern luxuries while retaining its era charm. This delightful home is light and bright. The main home boasts a welcoming living room with gas fireplace, dining room, family room, and a large renovated kitchen with striking granite countertops, a huge kitchen island, farm sink, wood shaker cabinetry, high end commercial Wolf & Subzero stainless steel appliances, and a 100+ bottle wine cooler. Off of the kitchen is a charming Butler's pantry with copper sink, vintage window, built in shelving and more spacious cabinetry. Open to the kitchen enjoy the family room, featuring its original refinished oak floor and unique raised ceilings and unparalleled view of the pool and backyard. The primary bedroom is spacious and bright and offers a built in closet plus modern extra tall cabinet storage space. The second bedroom is currently being used as an office and it too offers a built in closet. The pristine primary bathroom has a frameless glass shower surround, vintage look vanity, lighted mirror, modern tiled floor, and a Vela Plus Self Cleaning Smart Toilet/Bidet. Off of the dining room is an intimate bespoke cocktail lounge with lighted built ins, mirrored shelving and deep storage cabinets, which could be transformed into an office. The home boasts wide wood plank and distinctive tile flooring, a neutral color palette, unique lighting fixtures, ample storage, all culminating into a truly historic feel with modern, luxurious updates. The fenced backyard is lush, private and offers a view of St Joseph's Sound, multiple seating areas, and a tranquil 15x30 natural gas heated pool and spill over 8 person spa. There is a cabana with electrical wiring and windows, currently used as a work shed. The light and bright Carriage House is separate from the main home and shares similar high end finishes, with its tall ceilings, large tiled bathroom, a kitchenette, and spacious, sunny living area and a bedroom with high ceilings. It is heated and cooled by a 2 head mini split, and offers a beachy vibe with ceiling fans, painted wood flooring, and shiplap wall accents. This stunningly beautiful home is move in ready and offers many notable efficient & structural features including LOW E impact windows, whole house Generac generator, encapsulated crawl space, and a UV air purification system. With a home of this vintage, it is refreshing to see the renovations and updates have been permitted through the City of Dunedin. Watch the attached VIDEO to fully appreciate this home. The location is also first class; walk or jump in your golf cart to nearby shops and restaurants; the Pinellas Trail intersects the street and is just a stroll away. Watch the sunset from your own exquisite backyard, or head downtown for dinner or to the many festivals and events. Couple this with excellent schools, pristine beaches and all that fabulous Dunedin has to offer, and you have the ultimate elegant Florida lifestyle home!