Saint Augustine Historic District 2-Story Homes for Sale

Two homes. One address. Unlimited flexibility in Uptown St. Augustine. 16 Locust Street, also known as ‘The Sisters Cottages’ is a rare Abbott Tract offering featuring two fully restored historic cottages, each with its own private space and income potential. Positioned in one of Uptown’s most sought-after pockets, this property offers a level of versatility that is exceptionally hard to

Luke Newcomer The Newcomer Group

**OPEN HOUSE FROM 2-4 p.m., Friday May 15th, PLENTY OF PARKING AT THE PROPERTY** Welcome to 249 Charlotte Street, a rare opportunity to own a piece of historic charm in the heart of St. Augustine. A historic carriage house, this 3-bedroom, 2-bath home blends classic character with a relaxed coastal lifestyle, all just steps from the city’s vibrant shops, restaurants, and waterfront. Situated on

Douglas Pugh Florida Homes Realty & Mortgage

Located just 4 blocks from the heart of historic downtown St Augustine, 288 St George St sits on one of the city’s favorite tree-lined streets - known for timeless charm, welcoming neighbors and classic picket-fence appeal. Residents gather on front porches, greet dog walkers and cyclists passing by and plan neighborhood parties. Beautifully restored by its current owner, this historic St

Irene Arriola One Sotheby's - Downtown

Historic Charm. Modern Efficiency. Smart Living. Prime Downtown Investment. Nestled in the heart of St. Augustine’s coveted historic district—within Henry Flagler’s original neighborhood—this beautifully restored circa-1910 residence offers the rare blend of timeless architectural charm and today’s most sought-after modern upgrades. Behind its classic white picket fence and lush landscaping, this

ELIZABETH LANG Endless Summer Realty

Turnkey, income-producing, and perfectly positioned—this fully renovated historic home in St. Augustine’s Uptown District is a proven short-term rental just steps from St. George Street and minutes to Vilano Beach. Sold fully furnished and ready to go, this is a rare opportunity to step into immediate rental income in one of the most desirable areas of St. Augustine.A spacious front porch

Krista Hoff ENDLESS SUMMER REALTY

Set in the heart of America’s oldest city, this remarkable 1890 two-story property with solar and an automatic generator offers a rare blend of history, land and potential. Situated on a large corner lot, with valued RS-2 zoning short term rentals, the property enjoys exceptional views, marked by the cross where Ponce de León is believed to have come ashore, placing it among a small handful of

Diane Vespucci TEAM 100 REALTY

Welcome to the Pink House! Step into timeless charm with this beautifully preserved 1925 historic home, tucked away on a private lot in the heart of downtown St. Augustine. Surrounded by serene gardens and fountain features, this one-of-a-kind property offers both character and convenience just two blocks from the bayfront and steps from the city's iconic shops, restaurants, bustling nightlife,

Michael Krzeszewski JPAR CITY AND BEACH

With a location in the heart of Historic Downtown St. Augustine and only minutes to Vilano Beach, the Homes of 7 Sebastian Avenue effortlessly blend sophisticated design and luxury living. Developed by Ocean Life Homes, this exclusive four unit townhouse development is designed to comfortably accommodate those looking for low maintenance and a permanent residence, second home, or profitable

Nick Linser One Sotheby's - Downtown

This home exudes charm and character . It was designed by the famed architect , F.A. Hollingsworth and resides on one of the highest elevations on one of the most desired streets in , St Augustine. The timeless architecture has been carefully restored and enhanced with the finest materials and craftsmanship from exterior to interior. Step into the foyer where the original stairs , banisters , and

Michelle Mousin CHRISTIE'S INTERNATIONAL REAL ESTATE FIRST COAST

With a location in the heart of Historic Downtown St. Augustine and only minutes to Vilano Beach, the Homes of 7 Sebastian Avenue effortlessly blend sophisticated design and luxury living. Developed by Ocean Life Homes, this exclusive four unit townhouse development is designed to comfortably accommodate those looking for low maintenance and a permanent residence, second home, or profitable

Nick Linser ONE SOTHEBY'S INTERNATIONAL REALTY

50 Charlotte Street | St. Augustine, Florida - An Iconic Corner in the Heart of the Historic District Positioned at the prominent corner of Charlotte and Hypolita Streets, 50 Charlotte Street presents a truly rare offering in the heart of St. Augustine's historic district that has been lovingly held as a legacy property by the same family for over 50 years. Just one block from the Matanzas River

Jena Dennis Great Expectations Realty

Two homes, one property--minutes to Historic district and beach. This North City/Uptown gem offers a charming 2BR/2BA main residence plus a separate 2BR/1BA apartment above the garage for true flexibility. The main house showcases original hardwood floors, a brick wood-burning fireplace, and a flowing plan with a front sitting/sun room, living room, dining area, office/flex room, and an

Michelle Spinneweber RE/MAX UNLIMITED

Welcome to a one-of-a-kind property where timeless charm meets modern flexibility. This thoughtfully designed multi-generational home offers separate living spaces under one roof--ideal for extended families, in-laws, or adult children who want privacy without sacrificing togetherness.Currently operating as a successful Airbnb, this home generates strong rental income thanks to St.

LOURDES DIAZ WATSON REALTY CORP

This historic victorian house gives you the unique opportunity to live in it, open a business in it, or both. CL2 zoning allows for many different options. The upper and lower porches face east toward the water which is 2 blocks away. There are both a detached garage and a carport for parking. Inside there are wood floors throughout. There is a non-working fireplace with a victorian mantel as the

Robert Graubard A Green World Realty, LLC

Charming historic 4BR/3BA home surrounded by Spanish moss-draped live oaks and just minutes from Historic St. Augustine and local attractions. Historic character blends with modern updates, including wood flooring, a renovated kitchen, and stylish bathrooms. An inviting home including an open floor plan, a durable metal roof, gutters, an expansive front porch, and a private outdoor area. Eligible

Steve Pate RE/MAX SPECIALISTS PV

Welcome to 17 Aviles Drive, a rare 1928 cottage offering timeless character, flexible living, and exceptional income potential in the heart of St. Augustine. This 5-bedroom, 2-bath home is thoughtfully configured for multigenerational living or house hacking, featuring three total kitchens and a fully functional basement with a private entrance, ideal for extended family, guests, or rental use.

Alexia Cipollone DJ & LINDSEY REAL ESTATE

There are homes... and then there are pieces of history. Welcome to The Puello House, a rare and remarkable residence at 53 Marine Street in St. Augustine, originally constructed between 1812 and 1814 by Maria Puello during the city's Second Spanish Period. Built of native coquina stone, the same material used to construct the nearby Castillo de San Marcos, this extraordinary property has stood

Sydney Ragusa UNITED REAL ESTATE GALLERY

Rare downtown St. Augustine duplex — fully furnished, fully restored, and full of opportunity. Just one block from the nation's oldest street and two blocks from the bayfront, this historic property delivers an unbeatable location with flexible income potential. Each of the two apartments features 2 bedrooms, 1 bath, a full kitchen, living room, eat-in area, and private laundry. Property has up

CONOR FLYNN FLORIDA HOMES REALTY & MTG LLC