Vintage homes for sale & real estate in Monroe County, FL

Vintage Home for sale in Monroe County, FL:

Welcome to 1224 Seminary Street, a tranquil tropical retreat in one of Key West's most desirable neighborhoods--just moments from the White Street Arts District, Higgs Beach & the iconic White Street Pier. Set on an oversized 5400 sq. ft. lot, this unique property offers the best of island living w/ a compound of 2 separate homes, surrounded by lush greenery & classic Key West character. The main house w/ over 900 sq ft under air, features 2 bedrooms & 1.5 baths, open-concept kitchen, & a bright sunroom. The living area opens to a welcoming covered front porch, ideal for morning coffee or evening cocktails. A detached guest cottage, is 450 sq. ft w/ 1 bedroom, 1 bath,

Vintage Home for sale in Monroe County, FL:

Welcome to this beautifully maintained 3-bedroom, 3 bathroom pool home that offers exceptional space, privacy and flexibility - ideal for families, remote workers, or multiple generational living. Built with solid CBS construction with impact windows and doors, this thoughtfully designed home features multiple separate living spaces giving everyone room to spread out. Enjoy a bright sunroom/den, perfect for relaxing with a book or enjoying morning coffee with French doors leading to the pool, and a dedicated office or craft room that offers the perfect work-from home setup or creative retreat. There is also a large storage area/ workshop. Step outside and enjoy your own private concrete poo

Vintage Home for sale in Monroe County, FL:

Welcome to this Key West-style home located on Big Pine Key! Situated on a generous 7500 square-foot fully fenced lot, this property offers ample space for parking and storage, making it a perfect island retreat for those looking to escape the hustle and bustle. As you step inside, you'll be greeted by the cozy charm of two bedrooms and a well-appointed bathroom, providing a comfortable living space. The highlight of this home is the spacious upstairs loft, complete with three built-in twin size bunks, ideal for accommodating guests or creating a relaxing sanctuary for yourself. For added convenience, the property features an outdoor shower, perfect for rinsing off after a day of island act

Vintage Home for sale in Monroe County, FL:

Private Compound- 723 Eaton Street and 329 Peacon Lane, Old Town. An extraordinary property in the heart of Old Town, this compound is a masterclass in island living. Spanning from 723 Eaton Street to 329 Peacon Lane, the property includes one brand new home plus three additional beautifully reimagined residences, all set behind lush, professionally designed tropical landscaping with gated entrances on both sides. Located just steps from the Historic Seaport and near Fausto's Grocery, this prime location lies within Key West's oldest and most storied neighborhood. At the center of the compound is a grand yet welcoming main residence—brand-new construction featuring three bedrooms, thr