Masters Tract Real Estate, Homes, Condos for Sale in St Augustine, FL

Welcome home to this delightful corner-lot cottage, surrounded by citrus trees, swaying palms, and timeless Florida charm. Relax beneath the shade of a majestic oak tree and enjoy your own backyard oasis, featuring orange, lemon, and avocado trees, along with an elderberry bush--ready to grow and flourish for years to come. The spacious primary bedroom features elegant French doors that open onto the patio, creating the perfect spot to enjoy your morning coffee or unwind at the end of the day. Inside, the open-concept kitchen flows seamlessly into the living and dining areas, making everyday living and entertaining easy. Filled with warmth, character, and lush landscaping, this inviting home offers the best of Florida living. Conveniently located just minutes from the beach and downtown, it combines peaceful outdoor living with easy access to shopping, dining, and local attractions.

1463 Spring Street, St. Augustine

Listing courtesy of CENTURY 21 LIGHTHOUSE REALTY.

$520,000

3 Beds ⋅ 2 Baths ⋅ 2144786 MLS

From the moment you arrive at 1551 Masters Drive, a circular front driveway sets the tone for this truly exceptional property. A rear entrance from Spring Street provides additional convenience with parking for several vehicles, all set on a sprawling 0.8-acre lot. Built in 1928, this home's rare Coquina block construction -- a signature material of St. Augustine's storied architectural heritage -- offers the kind of durability and timeless character that simply cannot be replicated in modern construction. A durable metal roof adds lasting peace of mind. The main residence offers 3 bedrooms and 2 full bathrooms, where original hardwood floors flow throughout and a wood-burning fireplace anchors the living room, flanked by custom built-ins that add warmth and charm. The updated kitchen is as functional as it is inviting, featuring granite counters, stainless steel appliances, an overhead hood, farmhouse sink, center island, breakfast bar and charming built-in buffet with display cabinet An enclosed rear porch with laundry facilities rounds out the main living space with added flexibility. The primary suite offers a peaceful retreat complete with a large walk-in closet and a spa-inspired bath with separate soaking tub and shower. The secondary bath features a shower. Outdoor living is where this property truly distinguishes itself. A large covered rear deck with a separate spa, and an expansive paver patio with fire pit create an entertainer's paradise -- perfectly suited for enjoying Florida evenings year-round. A detached oversized one-car block garage with metal roof, a garden shed, and ample additional parking provides exceptional utility and storage. County water service plus a separate dedicated irrigation well keeps the lush 0.8-acre grounds pristine. For those seeking income potential or multi-generational living, the property delivers two outstanding guest accommodations. A detached guest cottage features a bedroom, kitchenette, half bath, and covered outdoor shower with vanity -- currently operating as an excellent short-term rental. An Airstream RV with a large private deck, covered outdoor shower, and carport offers a second lucrative income stream or a one-of-a-kind guest experience -- also currently operating as a successful short-term rental. Rarely does a property combine 1928 historic Coquina construction, nearly an acre of land, expansive outdoor living, and proven income-producing potential in one remarkable package. This is a true piece of Florida history -- and an opportunity not to be missed.

1551 Masters Drive, St. Augustine

Listing courtesy of KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE.

Selling Office: .

$370,600

2 Beds ⋅ 1 Baths ⋅ 2103519 MLS

One of the very few that is zoned CM2 which allows for nightly STR bookings instead of weekly! Historic Beauty in the Heart of St. Augustine. Just steps from the charm of the historic district, 33 Bernard Street blends timeless character with thoughtful updates. Walk to cobblestone streets, waterfront views, top-rated restaurants, and boutique shops—perfect for lovers of history and vibrant living. Inside, sunlit rooms feature original hardwood floors and vintage details alongside a modernized kitchen with sleek counters and quality cabinetry—ideal for casual meals or entertaining after a day of exploring. Relax in the private, landscaped courtyard with coffee or wine under the stars. With its prime location, the home offers strong potential as a short-term rental, second home, or full-time residence. Opportunities like this are rare in St. Augustine's historic core—don't miss your chance to own a piece of history. Schedule your private showing today.

33 Bernard Street, St. Augustine

Listing courtesy of ONE REALTY CORP.

Selling Office: .

$925,000

3 Beds ⋅ 4 Baths ⋅ 2097228 MLS

Welcome to your perfect retreat in the heart of downtown St. Augustine! This stunning 2021 custom-built home comes fully furnished and thoughtfully decorated, ready to embrace its new owner. Designed with care, it features soaring ceilings and an open living area that welcomes natural light, creating an inviting space for gatherings. You can walk to all the sites! The charming front porch beckons you to unwind with a cool breeze, while the expansive back porch offers additional outdoor serenity. The 1st floor master suite is a peaceful haven with a beautifully appointed bathroom. Upstairs, two guest bedrooms share a full bath plus small office area. The custom Kitchen is a show-stopper! The butler kitchen and pantry simplify entertaining and food prep. The well maintained, low-maintenance yard showcases native plants and zero-scape charm. Alley access and extra parking in back. This home is a perfect blend of historic charm and modern conveniences. High and dry, no flooding. No HOA!

17 Hope Street, St. Augustine

Listing courtesy of ST AUGUSTINE REALTY.

Selling Office: .

$325,000

2 Beds ⋅ 1 Baths ⋅ 2096992 MLS

Charming Downtown Bungalow - A Rare Airbnb Investment Opportunity Nestled in the heart of Historic St. Augustine, this 2 bed, 1 bath bungalow is brimming with charm, potential, and opportunity. Just a short walk to the shops, restaurants, and vibrant attractions of the nation's oldest city, this location is everything for guests seeking that perfect St. Augustine experience. The home itself needs a little love, but savvy investors will immediately see the equity upside with some thoughtful updates. Whether you're dreaming of creating your own cozy vacation rental or a personal weekend getaway, this is a diamond ready to shine. Here's what makes it even more exciting: This property is one of three neighboring homes currently for sale. Purchase one, two, or all three to create an Airbnb compound - a rare and highly desirable setup for multi-unit short-term rental success in a high-demand tourism hub. Opportunities like this in walkable downtown St. Augustine don't come around often. Bring your vision and seize this investment gem before it's gone!

20 Hope Street, St. Augustine

Listing courtesy of LPT REALTY LLC.

Selling Office: .

$425,000

3 Beds ⋅ 2 Baths ⋅ 2096990 MLS

Downtown St. Augustine Bungalow - Airbnb-Ready with Multi-Unit Potential Located in the heart of Historic St. Augustine, this charming 3 bed, 2 bath bungalow offers a rare opportunity for both personal enjoyment and serious investment. Just a short stroll to the city's best shops, restaurants, and attractions, this is exactly where travelers want to be. The layout provides a unique opportunity: With a little vision and renovation, this home can be transformed into two separate units—a 2 bed, 1 bath space downstairs and a 1 bed, 1 bath with an office upstairs. Live in one, rent the other, or maximize your returns by offering two Airbnb listings under one roof. Whether you're a seasoned investor or first-time host, the potential for short-term rental income is undeniable. And here's the kicker—this home is one of three neighboring properties available. Purchase one, two, or all three to create a rare Airbnb compound in a walkable, high-demand tourism zone. A little work will go a long way in unlocking both equity and income. Don't miss this opportunity to own a piece of the nation's oldest cityand turn it into something truly special.

18 Hope Street, St. Augustine

Listing courtesy of LPT REALTY LLC.

Selling Office: .

$307,200

2 Beds ⋅ 1 Baths ⋅ 2096985 MLS

Charming Downtown Bungalow - A Rare Airbnb Investment Opportunity Nestled in the heart of Historic St. Augustine, this 2 bed, 1 bath bungalow is brimming with charm, potential, and opportunity. Just a short walk to the shops, restaurants, and vibrant attractions of the nation's oldest city, this location is everything for guests seeking that perfect St. Augustine experience. The home itself needs a little love, but savvy investors will immediately see the equity upside with some thoughtful updates. Whether you're dreaming of creating your own cozy vacation rental or a personal weekend getaway, this is a diamond ready to shine. Here's what makes it even more exciting: This property is one of three neighboring homes currently for sale. Purchase one, two, or all three to create an Airbnb compound - a rare and highly desirable setup for multi-unit short-term rental success in a high-demand tourism hub. Opportunities like this in walkable downtown St. Augustine don't come around often. Bring your vision and seize this investment gem before it's gone!

14 Hope Street, St. Augustine

Listing courtesy of LPT REALTY LLC.

Selling Office: .

$802,500

6 Beds ⋅ 3 Baths ⋅ 1255777 MLS

Livin's easy when you're TRIPLEX is a 5 min walk to historic downtown STA and the world famous Castillo de San Marcos Fort! Live in 1 and rent out the 2 other units or create an Airbnb compound that will generate income for years to come! We invite you and your guests to enjoy all that this lil town has to offer from!

26 Hope Street, St. Augustine

Listing courtesy of STA REALTY.

Selling Office: .

$625,000

3 Beds ⋅ 3 Baths ⋅ 1228122 MLS

Location, Location, Location! Incredible multi-family property in the heart of vibrant St. Augustine, just steps away from the charm of Downtown. These two separate bungalows present a unique and highly desirable investment opportunity, perfect for both short-term rentals or as an owner-occupied residence with rental income. Set amidst a serene neighborhood, this property consists of two fully updated and move-in ready bungalows. The first bungalow is approx 1020 sqft and is a beautifully updated 2-bedroom, 2-bath residence featuring an open-concept living space, modern kitchen with stainless steel appliances and tastefully designed bathrooms with walk in showers. The second bungalow is approx 576 sqft and offers a cozy 1-bedroom, 1-bath setup that does not skimp on quality or style. It has a spacious living area, a well-equipped kitchen, and a full bath with modern fixtures. The properties come fully equipped with all the amenities needed for a comfortable living experience and have been meticulously maintained, reflecting a thoughtful blend of charm and modern convenience. Whether you choose to live in one and rent the other, or rent both units for maximum income potential, this property presents a fantastic opportunity for both experienced and first-time real estate investors. Thanks to its prime location, it offers a steady flow of potential tenants and short-term renters year-round. Take advantage of the flourishing St. Augustine rental market with this prime real estate, located within walking distance of downtown's restaurants, shops, historic sites, and local attractions. Don't miss this unparalleled opportunity to own a piece of St. Augustine's charm while securing a solid income stream. And to top it off, these homes have not flooded. Be sure to schedule your tour today. This unique property won't last long on the market!

10 Hope Street, St. Augustine

Listing courtesy of eXp REALTY LLC.

Selling Office: .

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