Vintage homes for sale & real estate in Longboat Key, FL

Vintage Home for sale in Longboat Key, FL:

Welcome to Crooked Coconut-a rare waterfront treasure in historic Cortez Village! Set along the beautiful shores of Sarasota Bay in Florida’s oldest fishing village, Crooked Coconut is one of the village's original homes! Truly a special piece of Old Florida history. Tucked away on a quiet dead-end street, this 3-bedroom, 2-bath home sits on an expansive bayfront lot, offering a wonderful blend of privacy, character, and laid-back coastal living. Step inside and feel the warmth and charm that make this home so special. Thoughtfully redecorated with a fresh, relaxed feel, the interior beautifully blends historic character with modern comfort. The welcoming foyer features a cozy sittin

Vintage Home for sale in Longboat Key, FL:

Two private living spaces. One affordable price! Looking for a home that offers a little more flexibility? This move-in-ready Bradenton property features an updated main residence plus an attached studio with its own private exterior entrance, full bathroom, and kitchenette. The main home offers a spacious primary bedroom and two additional compact rooms that could serve as guest rooms, a home office, hobby space, or additional storage. The updated kitchen features shaker-style cabinetry, quartz countertops, stainless steel appliances, wood look tile flooring throughout. What really sets this property apart is the studio, which is accessible exclusively from the exterior, offering added pri

Vintage Home for sale in Longboat Key, FL:

Virtually Staged. With Sarasota Bay directly across the street, 2815 Bay Drive offers a setting that makes location the heart of its story. Situated in Bradenton’s Bayshore Gardens, this three-bedroom, two-bath home sits on approximately a quarter-acre lot and features valuable recent improvements, including a roof approximately one year old, updated windows, and updated electrical and plumbing. Original terrazzo flooring runs throughout the home. The enclosed sunroom offers versatile space, with the potential to add a mini-split system for additional air-conditioned living space. Enjoy the recreational amenities of Bayshore Gardens, including a community marina, private boat ramp, fi

Vintage Home for sale in Longboat Key, FL:

Welcome to classic Mid-Century Modern living in Whitfield Estates! Tucked west of the Trail on a quiet street lined with mature oaks, this updated home sits just moments from the Bay and about halfway between the Sarasota Bayfront and Bradenton's downtown Riverwalk, so the best of both cities is always an easy drive away. Step inside and you'll find a home that's all about the light. Walls of windows and sliding glass doors fill every room with sunshine and blur the line between indoors and out, just the way Mid-Century design was meant to be enjoyed. Arrivals feel special here. A sweeping horseshoe driveway frames the landscaped front yard and leads to a generous porte cochère, so g

Vintage Home for sale in Longboat Key, FL:

Virtually Staged. Welcome to Bayshore Gardens, where this updated 2 bedroom, 1 bath block home sits on a seawalled canal with access to Sarasota Bay and the Gulf. The roof is about five years old and the A/C was replaced about two years ago, so the big-ticket items are already handled. Glossy marble-look porcelain tile runs throughout, paired with bright white walls and modern light fixtures. The open living and kitchen area features white shaker cabinetry, white countertops, a marble-look tile backsplash and stainless steel appliances. Both bedrooms are bright with dual windows in one and a canal view from the other, and the bathroom has been redone with a tiled walk-in shower, mosaic tile

Vintage Home for sale in Longboat Key, FL:

A little piece of Bayshore Gardens history! This 1959 home still has much of its original character, including terrazzo floors, along with several important updates: roof 2016, HVAC 2019, garbage disposal 2026, fence 2020 and shed 2021. Inside, you’ll find living and family spaces, a dining area, Florida room, three bedrooms, two full baths and inside laundry. Outside, the lot is completely xeriscaped, so there’s no lawn to mow. The location is another plus, with convenient access to IMG Academy, Sarasota, Bradenton, area beaches, shopping and dining. Bayshore Gardens residents enjoy access to a marina on Sarasota Bay with a private boat ramp, fishing dock, fish-cleaning stati