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1470 Arapaho Avenue, St. Augustine
$5,000,000
2162158 MLS
5 ACRES IN THE PATH OF GROWTH - PRIME ST. AUGUSTINE LOCATION! Incredible opportunity to own approximately 5 acres strategically located directly behind Target and adjacent to the exciting new Shipyards area in one of St. Augustine's rapidly developing corridors. The property is currently zoned Open Rural (OR) with a Mixed Use Future Land Use designation, offering a unique opportunity for an investor, developer, or owner/user to explore future possibilities. Currently going through a rezoning to commercial zoning. The surrounding area is experiencing significant investment and growth, including new Toll Brothers residential development featuring single-family homes and townhomes, The Southerly apartments, Asado Life restaurant, marina and waterfront activity, and additional nearby development creating an increasingly vibrant, walkable destination. The property offers approximately 800 feet of length and 290 feet of width, providing substantial acreage.

1470 Arapaho Avenue, St. Augustine

22 Hypolita Street, St. Augustine
$4,440,000
2159764 MLS ⋅ Casa Maya Restaurant & Tequila Bar BLDG.
Constructed in 1987 as the private residence of acclaimed novelist and artist Jack D. Hunter, this distinctive two-story building was thoughtfully transformed in 2012 into one of Historic Downtown St. Augustine's most unique full-service restaurant and tequila bar destinations. Professionally renovated by John Valdez & Associates, the conversion incorporated modern commercial systems designed for restaurant use, including a fire sprinkler and suppression system, while preserving the property's architectural charm and intimate residential character. Situated on approximately 0.12± acres, the property enjoys approximately 49 feet of frontage along the brick-paved Hypolita Street and an additional 109 feet of frontage on Toques Place, providing outstanding visibility and convenient pedestrian access from both sides of the property. Enclosed by a concrete block privacy wall, the restaurant offers a rare, private courtyard setting featuring mature shade trees, lush landscaping, decorative gardens, brick pavers, ambient lighting, and multiple outdoor gathering areas that create an inviting atmosphere unlike any other in the Historic District. The property is prominently positioned along one of downtown's primary pedestrian corridors and is highly visible to vehicular traffic, sightseeing tour trains, and the millions of visitors who explore St. Augustine each year. The improvements contain approximately 3,292± square feet of heated, cooled, covered, and support areas thoughtfully designed to create multiple guest experiences throughout the property. The first floor features a fully equipped commercial kitchen, food preparation areas, manager's office, hostess and waiting area around a fireplace, customer restrooms, two covered outdoor bars, and a spacious covered courtyard dining area. The second level offers an additional bar with seating, food preparation area, customer restroom, and two covered balconies overlooking both Hypolita Street and the private courtyard, providing a unique elevated dining experience. A detached service building includes storage, dishwashing facilities, a walk-in cooler, and an additional guest restroom conveniently serving the courtyard. Operating today as "Casa Maya Restaurant & Tequila Bar", the property has been thoughtfully designed to create multiple indoor and outdoor hospitality experiences within an intimate, garden-like setting. The private courtyard serves as the focal point of the property, complete with a covered entertainment stage, open space for dancing, and inviting gathering areas illuminated by decorative lighting and mature landscaping. Its versatile layout is well suited for casual and upscale dining, specialty beverage service, private events, rehearsal dinners, weddings, corporate functions, and live entertainment. Opportunities to acquire a purpose-built hospitality property with this combination of historic character, operational versatility, exceptional ambiance, and an irreplaceable location in the heart of America's oldest city are exceedingly rare. Located at 22 Hypolita Street in the heart of the Historic District of St. Augustine, this premier restaurant location benefits from one of Florida's strongest pedestrian-oriented tourism markets. Situated just one block from the bayfront and within easy walking distance of St. George Street, the property is surrounded by nationally recognized attractions, boutique hotels, museums, art galleries, retail shops, and some of the city's most popular restaurants and entertainment venues. The Historic District welcomes millions of visitors annually, creating consistent daytime and evening foot traffic throughout the year. The area hosts numerous festivals, live music events, holiday celebrations, and cultural attractions that drive repeat visitation from both tourists and local residents. The property's central downtown location offers exceptional visibility and accessibility, making it an ideal destination for lunch, dinner, and evening dining. Guests enjoy convenient access from nearby public parking facilities, hotels, bed-and-breakfasts, the St. Augustine Bayfront, and many of the city's signature landmarks, including Castillo de San Marcos National Monument. The surrounding mix of hospitality, retail, and entertainment uses creates a vibrant, walkable environment that consistently attracts both visitors and local patrons.

22 Hypolita Street, St. Augustine

199 Nix Boat Yard Road, St. Augustine
$2,450,000
2135329 MLS
Positioned in the heart of one of Northeast Florida's most dynamic coastal growth corridors, this 1.9-acre flex commercial parcel within the Cat's Paw Marina PUD presents a rare opportunity to develop in a rapidly transforming marine-centric environment. With approvals already in place, this site offers a streamlined path to development--ideal for office, mixed-use, commercial, or marine light industrial applications. Whether envisioning a boutique waterfront office concept, marine service facility, or a hybrid live-work destination, the flexibility of zoning paired with the location creates exceptional upside. The surrounding area is rapidly transforming, anchored by a new Toll Brothers luxury residential community and a $24M waterfront public park, already being hailed as one of the finest in Florida. This dynamic blend of upscale living, destination recreation, and marine infrastructure positions the property as a standout investment with immediate potential and long-term upside.

199 Nix Boat Yard Road, St. Augustine

178 Avenida Menendez, St. Augustine
$2,350,000
6 Beds ⋅ 5 Baths ⋅ 2118296 MLS
178 Avenida Menendez - An Iconic Flagler-Era Residence with Panoramic Bayfront Views Exquisitely restored and meticulously maintained. The Bodley/Bennett residence is a rare Flagler-era treasure, originally built in 1910 and thoughtfully renovated between 2010 and 2012. Perched along the Matanzas River, this historic legal home commands sweeping, panoramic vistas of the St. Augustine Bayfront and the legendary Bridge of Lions, offering a lifestyle defined by elegance, heritage, and unmatched waterfront charm. Boasting 6 bedrooms and 5 full baths, this residence seamlessly blends historic character with modern comforts. Yellow pine flooring, 8'' hardwood baseboards, original five-panel doors, and grand staircases evoke timeless craftsmanship while updated systems and finishes ensure contemporary luxury. Optional 1 year home warranty provided by Fidelity National Home Warranty. The First-Floor Residence is an ideal suite for generational living or distinguished guests, featuring 2 bedrooms, 1 full bath, a spacious living room with a period gas fireplace, and a formal dining room. The chef-inspired kitchen includes a Jenn-Air gas range, stainless steel appliances, granite countertops, and espresso-finished cabinetry accented with period hardwaremarrying modern convenience with classic detail. The Second-Floor Main Residence is Designed for refined living and entertaining. This level offers 2 bedrooms, 3 full baths, an inviting living room, formal dining, and a beautifully remodeled kitchen with gas range, updated cabinetry, and rich butcher block counters. Thoughtful layouts and elevated finishes create a sense of sophistication and comfort throughout. The Third-Floor Retreat is also the pinnacle of luxury living. This floor provides 2 bedrooms, 1 full bath, and a generous walk-out terrace framing some of the most breathtaking views of the Bayfront and Bridge of Lionsa private sanctuary perfect for morning coffee, sunset entertaining, or simply soaking in St. Augustine's timeless beauty. A rare convergence of history, architecture, and premier waterfront location, this residence is not just a homeit is a statement. Perfect for collectors of historic properties, lovers of fine craftsmanship, and those who seek an elevated lifestyle in one of Florida's most cherished cities. Experience St. Augustine living at its finestwhere every detail tells a story, every view inspires, and every moment is extraordinary.

178 Avenida Menendez, St. Augustine

200 Nix Boat Yard Road, St. Augustine
$1,900,000
2135337 MLS
Positioned in the heart of one of Northeast Florida's most dynamic coastal growth corridors, this 1.5-acre flex commercial parcel within the Cat's Paw Marina PUD presents a rare opportunity to develop in a rapidly transforming marine-centric environment. With approvals already in place, this site offers a streamlined path to development--ideal for office, mixed-use, commercial, or marine light industrial applications. Whether envisioning a boutique waterfront office concept, marine service facility, or a hybrid live-work destination, the flexibility of zoning paired with the location creates exceptional upside. The surrounding area is rapidly transforming, anchored by a new Toll Brothers luxury residential community and a $24M waterfront public park, already being hailed as one of the finest in Florida. This dynamic blend of upscale living, destination recreation, and marine infrastructure positions the property as a standout investment with immediate potential and long-term upside.

200 Nix Boat Yard Road, St. Augustine

9 Bonita Bay Drive, St. Augustine
$1,900,000
4 Beds ⋅ 5 Baths ⋅ 2118899 MLS
Nestled in the serene waterside enclave of Bonita Bay, 9 Bonita Bay Drive is a stunning Spanish-style retreat just steps from the heartbeat of historic St. Augustine. This elegant 4-bedroom, 4.5-bath home offers enormous refined living space across three levels, expertly crafted in 2020 with Old-World charm and modern luxury. Living areas are flooded with natural light, and include high-end finishes, built-ins, a gas kitchen range, and a charming eat-in kitchen with an island. An elevator provides seamless access across three stories. The home's four bedrooms each include their own en-suite bath, offering privacy and comfort for guests or family. The primary suite enjoys its own wing. The two balconies deliver extraordinary panoramic views. Sit with your morning coffee on the east-facing balcony as the sun rises, and in the evening, unwind with views of the Bridge of Lions and downtown on the north-facing balcony. Outside, a private, fenced backyard provides peace and seclusion, anchored by a sparkling in-ground pool  perfect for sun-drenched Outside, a private, fenced backyard provides peace and seclusion, anchored by a sparkling in-ground pool flanked by lush palms  perfect for sun-drenched lounging or evening soirees. A private boat dock gives you direct access to the Matanzas River / intracoastal waterway, allowing for boating, fishing, or leisurely paddling, and ultimately navigation out to the ocean  perfect for the water-lover's lifestyle. Despite its tranquil setting, this home is walking distance to downtown St. Augustine. You can easily stroll into the historic district, taking in its quaint streets, shops, restaurants, and cultural landmarks. From your balcony, you can even catch glimpses of the downtown skyline and the iconic Bridge of Lions, lending a postcard-like view and a front-row seat for fireworks on special occasions.

9 Bonita Bay Drive, St. Augustine

156 Avenida Menedez, St. Augustine
$1,700,000
2158449 MLS
A once-in-a-lifetime opportunity to build along St. Augustine's iconic Bayfront in the nation's oldest city. Located at 156 Avenida Menendez, this rare vacant lot offers the chance to construct the first new structure on this coveted stretch in over 100 years. Enjoy breathtaking views of Matanzas Bay, the St. Augustine Lighthouse, and spectacular sunrises, all just steps from world-class dining, shopping, marinas, and historic attractions. Zoned for multifamily use, this unique property offers endless possibilities, including a luxury residence or boutique investment (subject to applicable approvals). Opportunities to build new on the Bayfront are exceptionally rare, making this an extraordinary chance to own one of downtown St. Augustine's most desirable locations and create a legacy property in one of Florida's most historic and sought-after destinations.

156 Avenida Menedez, St. Augustine

1 South Street, St. Augustine
$1,600,000
2112714 MLS
Welcome to Bonita Bay, downtown St. Augustine's premier luxury waterfront community. Situated in the heart of historic downtown, Bonita Bay is the only gated luxury waterfront community in the area and this is your rare opportunity to own a .26-acre double lot, fully shovel-ready and primed for your custom home. This unique home site offers dual gated access with the ability to enjoy the security of the main community gate, plus the exclusivity of your own private gate, offering sole entry to the property. From your future home or the community marina, take in gorgeous Intracoastal views or enjoy some time on the water while utilizing your two deeded boat slips. Located at the corner of Marine and South Streets, you are walking distance to all downtown shops, dining, and historic attractions. Build the waterfront lifestyle you've always envisioned—right in the heart of one of Florida's most charming and historic cities.

1 South Street, St. Augustine

33 Old Mission Avenue, St. Augustine
$1,475,000
3 Beds ⋅ 3 Baths ⋅ 2158222 MLS
The National Register of Historic Places recognizes the circa 1886 Horace Walker House in downtown St. Augustine. This landmark gem designed by architect Franklin W. Smith who also designed the Casa Monica Hotel and Villa Zorayda in Moorish Revival design has been fully restored to the luxury and opulence of bygone days while melding modern conveniences of kitchen and baths. The rear of the house was expanded to feature fabulous outdoor living with outdoor kitchen, patio that can be open or enclosed and a courtyard backyard for event and guest entertainment. The property is zoned commercial and is currently used as a high end Air B&B and private event venue. If your goal is for a historic primary residence in the country's oldest continuously occupied city then enjoy 3 large bedrooms, 2 of which are ensuites, an upstairs rear balcony, large living room, dining room and all new kitchen with European appliances and flair, then this is it!

33 Old Mission Avenue, St. Augustine

53 Sanford Street, St. Augustine
$1,450,000
6 Beds ⋅ 2154005 MLS
Turn-Key 5-Unit Airbnb Property in the Heart of Historic Downtown St. Augustine - Fully Furnished & Ready for Immediate Income! Step into a rare opportunity to own a successful, established short-term rental property just steps from St. Augustine's iconic attractions. This meticulously restored multi-unit gem has been thoughtfully operated as a high-performing Airbnb, delivering consistent bookings and glowing guest reviews thanks to its unbeatable location and charming, private accommodations. Offered fully furnished, equipped, and completely turn-key, the new owner can seamlessly continue operations without missing a beat. Nestled in the heart of downtown St. Augustine, guests are surrounded by world-class history, dining, shopping, and entertainment. Rental history and performance data are available upon request, along with a detailed list of extensive updates and upgrades completed over the years. No flooding - FLOOD ZONE X. No HOA. Walk to everything downtown!

53 Sanford Street, St. Augustine

13 Rohde Avenue, St. Augustine
$1,399,999
7 Beds ⋅ 5 Baths ⋅ 2155822 MLS
RARE UPTOWN FIND! 7 BEDROOMS + DETACHED APARTMENT + ABUNDANT PARKING, JUST STEPS FROM DOWNTOWN ST. Historic Downtown isn't just a place to visit... it's a lifestyle. Start your morning with a walk to your favorite coffee shop, spend the afternoon exploring local boutiques or the bayfront, meet friends for brunch, enjoy dinner and live music, then stroll home without ever getting in your car. That's everyday life at 13 Rohde Avenue. Situated on an exceptional corner lot in the heart of Uptown, this unique property offers over 3,200 combined square feet between the beautifully updated main residence and detached apartment. The main home features 5 bedrooms and 3.5 bathrooms, while the detached 2-bedroom, 1-bath apartment offers its own kitchen, laundry, private entrance, separate electric meter, and separate HVAC system. Whether you're looking for a primary residence, a second home, multi-generational living, or an investment opportunity, this property offers exceptional flexibility. Both the main home and detached apartment currently operate as successful short-term rentals generating annual gross rental income exceeding six figures combined. Below the apartment, an oversized storage area offers endless possibilities for a workshop, hobby space, additional storage, or future customization. Multiple porches, balconies, and outdoor living spaces create the perfect setting to relax after a day downtown. Add abundant parking--an uncommon convenience this close to Historic Downtown--and you have a property that's as practical as it is enjoyable. This isn't simply a home in Historic Downtown St. Augustine... it's the opportunity to live where people vacation.

13 Rohde Avenue, St. Augustine

47 Osceola Street, St. Augustine
$1,295,000
4 Beds ⋅ 4 Baths ⋅ 2166519 MLS
Situated in the coveted Abbott Tract in historic St. Augustine, this immaculately maintained home offers the rare combination of a private saltwater pool, detached guest villa, and detached 1½-car garage--all just one block from Castillo De San Marcos fort, the Bayfront, and St. Augustine's renowned restaurants, galleries, and boutiques. Built in 1920, the main residence offers 1,963 square feet with three bedrooms and three full baths, including a spacious first-floor owner's suite. Original wood floors, a gas fireplace, crown molding, and a wide covered and screened front porch preserve the home's timeless character, while impact-resistant windows, a metal roof, and fresh interior and exterior paint provide modern comfort and peace of mind. The light-filled kitchen features white cabinetry, stainless steel appliances, and a distinctive blue tile backsplash. Upstairs offers a cozy office or reading area, full bath and separate guest quarters. Just beyond the main home, the detached poolside guest suite (deemed the Villa) with a full bath creates a flexible fourth bedroom and fourth bath--ideal for visiting guests, a private office, studio, or independent retreat. Outdoor living is centered around the screen-enclosed saltwater pool with built-in spa seating, complemented by mature landscaping, a spacious and private fenced backyard, and a gas fire-pit for relaxed evenings and entertaining. Additional highlights include an extended paver driveway with valuable off-street parking and RS-2 zoning that allows for short-term rental use, offering flexibility for both personal enjoyment and income potential. The property is offered with or without the adjoining buildable lot at 45 Osceola Street, creating the opportunity for additional privacy, future development, expanded grounds, or a one-of-a-kind private compound in one of St. Augustine's most desirable neighborhoods. Welcome home.

47 Osceola Street, St. Augustine

40 Magnolia Avenue, St. Augustine
$1,290,000
4 Beds ⋅ 4 Baths ⋅ 2151988 MLS
A rare opportunity for turn-key investment; top rated, Short Term Rental located near historic downtown St. Augustine cash flowing tens of thousands per year. Built in 2023, ''Magnolia View'' located on the picturesque tree-lined street of Magnolia Avenue features 4 bedrooms, 3.5 baths, 2413sqft of living space, heated saltwater pool, wood flooring throughout, stunning kitchen, and impressive master bath with glass enclosed shower, dual vanities, and deep freestanding tub. Walking distance to the shops and restaurants of the Uptown neighborhood, and less than 1 mile to the heart of historic downtown, 2 miles to the beach. No HOA or historic restrictions. This property delivers the perfect blend of luxury, location, and proven returns, making it an exceptional addition to any portfolio. Home next door is also available, same floor plan.

40 Magnolia Avenue, St. Augustine

38 Magnolia Avenue, St. Augustine
$1,290,000
4 Beds ⋅ 4 Baths ⋅ 2151989 MLS
A rare opportunity for turn-key investment; top rated, Short Term Rental located near historic downtown St. Augustine cash flowing tens of thousands per year. Built in 2023, ''Canopy Oaks'' located on the picturesque tree-lined street of Magnolia Avenue features 4 bedrooms, 3.5 baths, 2413sqft of living space, heated saltwater pool, wood flooring throughout, stunning kitchen, and impressive master bath with glass enclosed shower, dual vanities, and deep freestanding tub. Walking distance to the shops and restaurants of the Uptown neighborhood, and less than 1 mile to the heart of historic downtown, 2 miles to the beach. No HOA or historic restrictions. This property delivers the perfect blend of luxury, location, and proven returns, making it an exceptional addition to any portfolio. Home next door is also available, same floor plan.

38 Magnolia Avenue, St. Augustine

62 1/2 Valencia Street, St. Augustine
$1,250,000
5 Beds ⋅ 3 Baths ⋅ 2116776 MLS
Own a piece of St. Augustine charm with this well-maintained triplex located just steps from Flagler College and the heart of downtown. Perfectly situated for investors or owner-occupants, this income-producing property features three separate apartments with private entrances and paved off-street parking for all residents. Two of the apartments each offer 2 bedrooms and 1 bathroom, while the third unit is a 1 bedroom, 1 bathroom. The current owner occupies one of the 2-bedroom units, another is vacant and ready for a new tenant or owner, and the 1-bedroom apartment is rented month-to-month. This turn-key property has been carefully maintained over the years, with a newer roof (approximately 2 years old) and thoughtful updates throughout. Two apartments share an on-site laundry area, while one unit includes its own washer and dryer. The ground-level garage/storage area provides added convenience and includes a full bathroom—offering flexibility for future use. A shared covered patio creates an inviting outdoor space, perfect for relaxing or entertaining. Located within walking distance of restaurants, shops, and the historic district, this property offers both immediate income potential and long-term value in one of Florida's most desirable coastal markets.

62 1/2 Valencia Street, St. Augustine

48 Osceola Street, St. Augustine
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 2167088 MLS
A rare gem in St. Augustine's highly coveted Abbott Tract, this circa-1900 residence captures the timeless allure of historic downtown living with the ease of modern updates. Beautifully preserved and thoughtfully enhanced, the property offers a sparkling blue lap pool surrounded by tropical foliage, the 2-bedroom, 2-bath main home along with a detached 1-bedroom, 1-bath guest suite featuring a private entrance and kitchenette--ideal for elegant guest accommodations, multigenerational living, or premium short-term rental income. Rich hardwood flooring, historic architectural details, and an undeniable sense of character define the interiors, while the open-concept rear living area creates a seamless setting for relaxed living and entertaining. The two bedrooms are gracefully situated at the front of the home, each with en-suite bath access, with one bath also conveniently serving visitors from the main hall. The kitchen is a perfect blend of style and function, featuring stainless steel appliances, ample prep space, and a breakfast bar that invites casual dining and conversation. Glass sliders off the living room open to a screened-in porch overlooking a serene backyard retreat, complete with a private pool--ideal for unwinding under the Florida sun. The detached guest suite offers flexibility and privacy, featuring a full bedroom and bath, along with a kitchenette to accommodate long or short stays. An extended driveway allows for rare off-street parking for two or more vehicles--a highly sought-after amenity in the historic district. Perfectly situated, this residence is just blocks from St. Augustine's most iconic landmarks, including the Castillo de San Marcos and the Mission Nombre de Dios. A short walk takes you to the waterfront at the end of Locust Street, where you can launch a kayak and explore the tranquil waters of Matanzas Bay. Zoned RS-2, the property also allows for weekly short-term rentals, further enhancing its value as both a personal retreat and a savvy investment. Offering historic charm, premium location, and modern livability, this is your opportunity to own a piece of St. Augustine's enduring legacy--an exceptional lifestyle awaits.

48 Osceola Street, St. Augustine

22 Joiner Street, St. Augustine
$1,150,000
4 Beds ⋅ 3 Baths ⋅ 2160596 MLS
Step into a rare opportunity to own a beautifully restored piece of St. Augustine history in the desirable Abbot Tract neighborhood. Originally built in 1900, this stunning 4-bedroom, 2.5-bath home has been completely remodeled from top to bottom while thoughtfully preserving the timeless character and architectural charm that make historic homes so special. Situated on one of the largest lots in the area, this exceptional property offers the perfect blend of historic elegance and modern peace of mind. Extensive renovations include a new metal roof, new HVAC system, new structural piers, new decking, new subflooring and flooring, new windows, fresh interior and exterior paint, new appliances, and countless additional upgrades throughout the home. Enter through the side entrance from the driveway into a welcoming landing area that sets the tone for the home's inviting atmosphere. Inside, new luxury engineered flooring flows throughout most of the home, while beautiful wainscoting adds character and sophistication to the living room. The spacious primary suite is conveniently located on the first floor and features an elegant coffered ceiling, creating a private retreat within the home. A conveniently located half bath completes the main level. Upstairs, you'll find the additional bedrooms along with a second-floor laundry area for added convenience. Step outside onto the newly rebuilt upper deck, complete with outdoor ceiling fans, creating the perfect space to enjoy coastal breezes and views of the surrounding historic neighborhood. New decking on both levels, including the expansive wraparound porch on the first floor, provides abundant opportunities for outdoor entertaining and relaxation. Located just a short distance from the Intracoastal Waterway and within walking distance of Historic Downtown St. Augustine, you'll enjoy easy access to renowned restaurants, boutique shopping, local attractions, and entertainment while still enjoying the charm and tranquility of one of the city's most treasured historic neighborhoods. This is a rare chance to own a turnkey historic home that offers the beauty of the past with the comfort and reliability of modern construction updates.

22 Joiner Street, St. Augustine

34 E San Carlos Avenue, St. Augustine
$1,075,000
4 Beds ⋅ 4 Baths ⋅ 2159488 MLS
Just a few homes from Magnolia Avenue, one of North America's most photographed streets, sits a property that perfectly captures the charm and lifestyle of St. Augustine. Built in 2022, this thoughtfully designed four-bedroom, 3.5-bath pool home blends modern construction with one of the city's most iconic and walkable neighborhoods. Offered fully furnished and turn-key, this is a rare opportunity to step into a home that's ready to be enjoyed from day one. Opportunities to own newer construction in this historic setting are few and far between, making 34 E. San Carlos an exceptionally rare offering. The heart of the home is the second floor, where the kitchen, dining area, and living room flow effortlessly together to create an inviting space for everyday living and entertaining. A conveniently located half bath serves the main living area, making hosting family and friends a breeze. The third floor features three bedrooms, including a spacious primary suite complete with a beautifully appointed ensuite bath and generous closet space, along with two additional guest bedrooms and a full guest bathroom. On the first floor, an oversized one-car garage is complemented by a private fourth bedroom and full bathroom, creating an ideal guest suite. Whether used for visiting family and friends, multigenerational living, a home office, fitness room, or even as a pool cabana, the flexibility of this space is a tremendous bonus. As impressive as the interior is, the backyard is where this home truly shines. Centered around an L-shaped pool and spa, the outdoor living space was designed for Florida living, featuring multiple lounging areas, space to entertain, backyard barbecues, and afternoons spent soaking up the Florida sunshine. Beyond the home itself is a lifestyle that's difficult to replicate. Stroll beneath the iconic oak canopy of Magnolia Avenue, grab a coffee or fresh lemonade at the Fountain of Youth, enjoy dinner at some of St. Augustine's most celebrated restaurants, explore the city's rich history, or take a quick bike ride to Vilano Beach. It's the perfect blend of historic charm, vibrant local culture, and coastal living. Whether you're searching for a full-time residence, a second home, or a property with the added flexibility of desirable RS-1 zoning for short-term rentals, 34 E. San Carlos offers a rare opportunity to own a newer home in one of St. Augustine's most treasured neighborhoods. Schedule your private showing today.

34 E San Carlos Avenue, St. Augustine

4 E San Carlos Avenue, St. Augustine
$1,050,000
4 Beds ⋅ 4 Baths ⋅ 2163379 MLS
A distinctive St. Augustine home with the space, character, and location to experience the city in a way that few properties can offer. Located in the sought-after Uptown/Nelmar Terrace area, 4 E San Carlos Ave combines coastal-inspired architecture, mature oak trees draped in Spanish moss, multiple outdoor living spaces, and an exceptional location near historic St. Augustine and the breathtaking beach. From the welcoming covered front porch and mature landscape to the private pavered courtyard, this home makes an immediate impression. Inside, the 4-bedroom, 3.5-bath layout offers 2,772 square feet of thoughtfully designed living space, including a spacious bonus/game room, separate cozy office, and open living areas designed for both everyday life and entertaining. The heart of the home is the bright, open kitchen featuring white cabinetry, quartz countertops, stainless-steel appliances, glass-tile backsplash, a large island, and a walk-in pantry. The kitchen opens naturally to the living and dining areas, while a fireplace adds warmth and character to the main living space. Upstairs, the private primary suite includes its own balcony, creating a peaceful and relaxing outdoor retreat overlooking the surrounding mature landscape. The spacious bonus/game room adds valuable flexibility for a media room, recreation space, guests, or a second living area. Outdoor living is a true highlight. Enjoy the covered front porch, rear porch, private primary-suite balcony, and beautifully designed pavered courtyard, complete with tropical landscaping, comfortable seating, and a dedicated grilling area. Additional yard space provides room to enjoy the outdoors without sacrificing the home's convenient location. Practical features are equally well considered, including an extended driveway, 2.5-car garage, no HOA, and generator inlet—with room for vehicles, bikes, a golf cart, storage, and the extras that come with enjoying life in St. Augustine. And then there is the location. Historic St. Augustine is part of everyday life here. Walk to historic landmarks and museums, the Fountain of Youth, and beautiful Magnolia Avenue, where centuries-old live oaks create one of the city's most iconic settings. Enjoy nearby restaurants, galleries, shops, waterfront activities, and fishing along the Matanzas. From this location, a bike ride can take you toward historic downtown or in the direction of the coast and beaches. This is not simply a home near historic St. Augustine. It is a home that allows you to experience it. Mature trees, distinctive architecture, multiple outdoor spaces, thoughtful interior amenities, and a location connected to the history and coastal lifestyle of the city come together in a property that is truly distinctive. 4 bedrooms | 3.5 baths | 2,772 SF | Bonus/Game Room | Office | Private Primary Balcony | Pavered Courtyard | 2.5-Car Garage | No HOA Come experience 4 E San Carlos Ave in person and discover the character, space, and location that photographs alone cannot fully capture.

4 E San Carlos Avenue, St. Augustine

251 Charlotte Street, St. Augustine
$949,000
4 Beds ⋅ 2 Baths ⋅ 2128943 MLS
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 to four parking spots. The owner has preserved the historic character while upgrading electrical, plumbing, and HVAC — each unit has its own electric meter and central heat & air. Enjoy over 1,880 sqft of living space with covered porches, a balcony, and a private back patio perfect for grilling or pets. Rent both units for maximum returns, live in one and rent the other, or convert to a single-family home with ease. All appliances included. Minutes to the beaches, steps to dining, shopping, and everything that makes St. Augustine one of the most desirable locations in Florida.

251 Charlotte Street, St. Augustine

67 Oneida Street, St. Augustine
$899,000
3 Beds ⋅ 3 Baths ⋅ 2162808 MLS
This stunning house is in the heart of historic St. Augustine. A wide paver driveway, layered landscape lighting, and manicured grounds set the tone before you reach the door. Inside, 3 bedrooms, 2.5 baths, and a versatile bonus family room/office are finished with luxury vinyl flooring throughout. The kitchen is the showpiece: stainless steel appliances, crisp white shaker cabinetry, and striking leathered granite. Out back, an expansive paver patio invites long evenings at the grill or quiet mornings with coffee and a good book. The location is the kind you simply cannot build. Stroll to St. George Street, Flagler College, the Castillo de San Marcos, and the city's best restaurants, bars, and nightly entertainment. The Lightner Museum sits just minutes away, and Vilano Beach, St. Augustine Beach, and major shopping are each a 10-15 minute drive. Completely turnkey as a well-established short-term rental. Move in and enjoy, or keep the calendar booked from day one. There is also potential to add a bathroom downstairs, creating the opportunity for a fourth sleeping space and increasing occupancy to approximately 10 guests. Offering a greater income. Homes with this kind of flexibility and investment upside don't last. Schedule your private showing today.

67 Oneida Street, St. Augustine

18 Locust Street, St. Augustine
$899,000
3 Beds ⋅ 2 Baths ⋅ 2161241 MLS
Discover the timeless elegance of this beautifully preserved Victorian residence nestled in the heart of St. Augustine's coveted Historic Abbott Tract. Situated high and dry beneath a magnificent canopy of mature oak trees, this exceptional home blends historic charm with modern comforts in one of the city's most desirable neighborhoods. Inside, rich spilled honey hardwood floors flow throughout the home, creating a warm and inviting atmosphere. The updated kitchen features quality finishes, an inviting breakfast area, and effortless access to the living spaces, making it ideal for both everyday living and entertaining Multiple covered porches provide the perfect setting to relax with a morning coffee or unwind in the evening while enjoying the tranquil surroundings and timeless beauty of the Historic District. Outside, the expansive yard offers endless possibilities, with ample space to add a resort-style pool, create lush gardens, or design your own private outdoor oasis. A detached two-car garage provides excellent storage and parking while also offering the potential for future expansion or a guest suite. Rich in character, thoughtfully updated, and ideally located just moments from Historic Downtown St. Augustine's renowned restaurants, boutique shopping, galleries, and waterfront, this remarkable Victorian offers a rare opportunity to own a true piece of the nation's oldest city's history.

18 Locust Street, St. Augustine

348 Charlotte Street, St. Augustine
$899,000
3 Beds ⋅ 3 Baths ⋅ 2157738 MLS
Step into the timeless charm of historic St. Augustine with this beautifully updated 3-bedroom, 3-bathroom home located on prestigious Charlotte Street--one of the city's most sought-after addresses. Built in 1900, this exceptional two-story residence showcases the classic architectural character that makes St. Augustine so unique while offering the modern updates today's homeowners desire. Spanning well over 2,000 square feet, the home features solid flooring throughout and a thought fully renovated interior that perfectly balances historic elegance with contemporary comfort. The updated kitchen offers a clean, slightly modern aesthetic, making it an inviting space for both everyday living and entertaining. The luxurious primary bathroom has been beautifully remodeled, creating a spa-like retreat within the home. Outside, the property's historic exterior blends seamlessly into one of St. Augustine's most charming and desirable neighborhoods. Enjoy the convenience of being just a 10-minute walk from the heart of historic downtown, where you'll find award-winning restaurants, boutique shopping, art galleries, waterfront attractions, and year-round events. Whether you're searching for a primary residence, second home, or an opportunity to own a piece of St. Augustine's rich history, this remarkable Charlotte Street home offers an unmatched combination of location, character, and modern living. All major items are newer! New ACs in 2022 and 2024, New Windows and Exterior Paint in 2024. Both water heaters are under 18 months old. Roof is 13 years old. Stress free living awaits!

348 Charlotte Street, St. Augustine

158 Blanco Street, St. Augustine
$875,000
4 Beds ⋅ 3 Baths ⋅ 2143082 MLS
Fully renovated and income producing, this exceptional two-story, four bedroom, three bath property is ideally located in the heart of historic St Augustine, just a short walk to vibrant downtown attractions, dining, and entertainment. Currently operating as a successful short-term rental on Airbnb and VRBO, this turn key investment offers both immediate revenue potential and long term value. Thoughtfully updated from top to bottom, the home features a new roof, new windows, updated plumbing and electrical systems, and fresh interior and exterior paint, Inside, you'll find durable luxury vinyl flooring throughout, a beautifully renovated kitchen with solid surface countertops, soft-close cabinetry, tile backsplash, stainless steel appliances and a farmhouse sink. All bathrooms have been fully updated with modern fixtures and finishes. The spacious second-floor primary suite offers privacy and comfort, complete with a step-in shower and a full retreat style layout. A custom built rear deck provides the perfect space for outdoor entertaining, while the oversized lot allows for ample parking-an uncommon and valuable feature in this sought after downtown location. Whether you're looking to expand your investment portfolio or own a fully updated property in one of Florida's most desirable historic destinations, this property delivers unmatched charm, convenience and income potential. This property can only be shown during the hours of 11-3 as it stays rented consistently.

158 Blanco Street, St. Augustine

7 Sebastian Avenue Unit D, St. Augustine
$869,000
3 Beds ⋅ 3 Baths ⋅ 2113264 MLS
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 investment opportunity. Each unit will boast a spacious two story, three bedroom, two and a half bath floor plan with a one car garage, and private 7x12 in ground pool. Interior finishings have been artfully curated to ensure only the highest quality products are utilized throughout each home. Outside, xeriscaping will be implemented to achieve minimal water usage with little to no irrigation required and pool maintenance will be included in the HOA fee. This is a rare opportunity to own a new construction luxury townhome, surrounded by shopping, dining, and walking distance to historic attractions in the epicenter of the Nation's Oldest City. For further details and specifications, contact us today.

7 Sebastian Avenue Unit D, St. Augustine

4 St. Andrews Court, St. Augustine
$799,000
3 Beds ⋅ 2 Baths ⋅ 2157793 MLS
Fabulous fully-renovated and furnished 2-story 3 BR, 2 baths turn of century Victorian in heart of downtown St. Augustine -- close walk to Flagler College, Cathedral, restaurants and shops, and bayfront. Short-term rental income-producing, and ideal for empty nesters or second homeowners. Enjoy the breezes from the rocking chair of your front porch or upstairs balcony. Much of this classic design remains original, from doors, hardware to hardwood floors, which sparkle on first and second floor. Furnished and move-in ready, home flows seamlessly -- combining historic charm with contemporary comforts, making it a truly special find in the heart of the city. Bright updated kitchen that features SS appliances, white cabinets and beautiful countertops.A must see on your downtown St. Augustine showing list!

4 St. Andrews Court, St. Augustine

88 Lincoln Street, St. Augustine
$775,000
4 Beds ⋅ 4 Baths ⋅ 2121885 MLS
Welcome Home to one of the most desirable homes in historical Lincolnville! What started as a restoration ended up being 95% new construction! This 4 bedroom, 3.5 bath FURNISHED home sits on a quiet street and is in walking distance to everything downtown St Augustine has to offer! The oversized Master bedroom is located on the 1st floor, In-law suite and 2 additional bedrooms joined by a jack and jill bathroom are all located on the 2nd floor. Open concept, the living room/dining room flow into this stunning custom designed kitchen that comes equipped with GE profile appliances, under cabinet lighting and stunning quartz countertops! The metal roof and Trane 16 Seer heat pump A/C system with dual zones for each floor temperature control, are a little less than 5 years old. LED recessed lighting throughout, wood flooring, new PGT double pane low E windows, pre-wired for cable and CAT-6 wire, tankless water heater, paver driveway, make this house MOVE IN READY! **No Seller Financing Home is zoned for weekly vacation rentals and can also be a great investment! Buyer is responsible for doing all due diligence when considering. Vacant and easy to show. Schedule through showing time!

88 Lincoln Street, St. Augustine

6 E San Carlos Avenue, St. Augustine
$740,000
4 Beds ⋅ 3 Baths ⋅ 2162822 MLS
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 all-season room. The updated kitchen features new cabinetry, counters, and appliances; lighting and doors have been refreshed throughout. Each bedroom functions as an owner suite, and both open directly to decks overlooking the newly fully fenced backyard under grand live oaks and Spanish moss--perfect for morning coffee, evening wine, or weekend gatherings. This property is ideal for multigenerational living, guest quarters, a home office, or generating potential income as a short-term or long-term rental.

6 E San Carlos Avenue, St. Augustine

160 Washington Street, St. Augustine
$725,000
2096375 MLS
Historic St Augustine - Discover the perfect blend of tranquility and convenience with this stunning 0.24acre marsh-front lot, located in the heart of historic downtown St. Augustine. Just a short walk to charming shops, delightful restaurants, and all the attractions this beautiful city has to offer, yet tucked away enough to offer a peaceful, serene retreat. The lot boasts breathtaking marsh and sunrise views, providing a picturesque backdrop for your dream home. Beautiful, mature trees grace the property, adding to its natural beauty and offering privacy and shade. With its prime location and unmatched views, this is the ideal canvas to build the home you've always envisioned. Don't miss the opportunity to own a piece of paradise in one of the most desirable areas in St. Augustine.

160 Washington Street, St. Augustine

315 Riberia Street, St. Augustine
$689,000
2 Beds ⋅ 3 Baths ⋅ 2148580 MLS
Welcome to 315 Riberia Street, a beautifully designed contemporary home built in 2022 and located in one of St. Augustine's most sought-after areas. Offering 2 bedrooms, 2 full baths, and 1 half bath across 1,417 square feet, this fully furnished, turnkey property is currently operating as a successful vacation rental and is zoned RG-1, allowing for nightly rentals within theCity of St. Augustine. Inside, you'll find an open-concept floor plan filled with natural light, elevated ceilings, and modern finishes throughout. The spacious kitchen features a large island, ample cabinetry, and seamless flow into the living and dining areas--perfect for entertaining guests or relaxing after a day exploring downtown. Enjoy peaceful evenings on the front porch watching spectacular sunsets over the San Sebastian River, or gather with friends and family beneath the backyard pergola. Whether you're seeking a primary residence, second home, or income-producing investment property, this move-in-ready home offers the best of St. Augustine living. Just a 12 minute walk to historic downtown, local restaurants, shops, marinas and attractions, this is a rare opportunity to own a modern, turnkey property in a prime location with short-term rental flexibility.

315 Riberia Street, St. Augustine

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