A Rare Crescent Beach Investment Opportunity — Just Minutes from the Beach! Discover the perfect blend of coastal living, privacy, and investment potential with this beautifully renovated ranch-style duplex, ideally situated on a quiet dead-end street in desirable Crescent Beach on Anastasia Island. Just a short stroll from the beach, this unique property offers the flexibility of a turnkey investment, second home, or primary residence with rental income potential. With a dividing privacy fence, ample parking, and attached garages for both units, this property delivers the convenience of a true lock-and-leave coastal retreat. Unit A has been completely transformed, featuring a beautifully refreshed kitchen, updated flooring and trim, washer and dryer, beautifully remodeled bathrooms, upgraded windows and hardware, and a covered rear porch—creating a fresh, comfortable, and inviting space from top to bottom.
With historic charm and situated in a prime business district, this multi-family duplex property promises a lucrative, reliable stream of income ~ making it an ideal opportunity to own a piece of St. Augustine's history while securing an excellent return on investment. Located in booming Uptown St. Augustine close to a wide array of cafes, restaurants, bars, hotels and boutiques ~ directly across from the world-renowned Florida School for the Deaf & Blind. With an expansive 80' x 154' corner lot and room to add an additional income-producing unit, bring your creative concepts and take this unique investment property to the next level. Unlock the full potential and value of this circa 1885 St. Augustine treasure. This is your chance to create and brand a multiple-unit Historic Vacation Cottage or enjoy multi-generational living in the nation's oldest city.
Unique opportunity to own a legal duplex in the Fullerwood neighborhood with nightly rentals allowed (RG-1 zoning)! Welcome to 12 Sylvan Drive, a rare and versatile gem nestled in the highly sought-after Fullerwood Park neighborhood of historic St. Augustine. Originally built in 1925 and thoughtfully updated, this unique property blends timeless character with modern comfort—offering exceptional flexibility for homeowners, investors, or those seeking a multi-generational living setup.
Discover a rare investment opportunity in the heart of historic St. Augustine! This updated and remodeled duplex is ideally situated on a corner lot just minutes from the city’s renowned historic attractions, dining, shopping, entertainment, and vibrant downtown district. Each thoughtfully designed unit features 1 bedroom, 1 bathroom, a full kitchen, and its own private laundry, offering comfortable and functional accommodations for short-term guests. The lower-level unit showcases classic hardwood flooring and a welcoming layout, while the second-floor unit enjoys a separate entrance, a covered front balcony, and a spacious rear deck—providing desirable outdoor spaces for guests to relax and enjoy the St. Augustine lifestyle. Both units have been updated and maintained to support the property’s established rental appeal. This duplex has grossed approximately $100,000 annually for the past 10 years, demonstrating a strong history of short-term rental performance.
Discover endless possibilities with this charming Anastasia Island duplex! Whether you're seeking a single-family home with an in-law suite, a combination of long and short-term rentals, or a live/rent scenario, this property has you covered. Nestled on an expansive double lot, this home comprises two fully self-contained units. Unit #1 boasts a beautifully renovated two-bedroom, two-bath layout, featuring new plumbing and electrical systems. Offered turnkey with only a few personal items excluded, it has garnered rave reviews as a successful short-term rental, earning the title of "Guest favorite" with a stellar 5-star rating on AirBnB, backed by 150 glowing reviews. Unit #2 presents a cozy one-bedroom, one-bath space and predominantly utilized as a long-term rental.
Excellent investment and redevelopment opportunity! This TWO-BUILDING PORTFOLIO IS PRICED TOGETHER AS A PACKAGE and includes 2 Dufferin St. and 1 San Carlos Ave. Zoned CM-2, offering a variety of potential commercial, residential and mixed-use possibilities. 2 Dufferin Street was home to a successful hair salon for the past 20 years and is now vacant, ready for its next owner or business. 1 San Carlos Avenue is a duplex featuring a downstairs 2-bedroom, 1-bath unit (with the potential to be converted into a 3-bedroom, 1-bath) of approximately 1,398 SF, and an upstairs 2-bedroom, 1-bath unit of approximately 900 SF. Whether you're looking for income-producing rental properties, a live/work opportunity, or future redevelopment potential, this property offers flexibility and value. The two parcels provide approximately 10 parking spaces combined. Buyer to verify all measurements, zoning, permitted uses, and redevelopment potential.
The ultimate in Florida living. Ocean breezes, strolls along the sand, and coastal cuisine are just the beginning of the activities surrounding this St Augustine Beach property with multifamily zoning, allowing for many options & commercial uses. The sought-after enclave of Anastasia Lodge includes a large fenced yard room for a pool and privacy for all. Complete updates offer refreshing furnishings, open spaces, and space for everyone. Currently used as two units sleeping 12, many options are available for this one-of-a-kind property s including but not limited to short-term rentals, and additional spaces, ideas are endless. Very popular STR so appointments are needed
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.
Exceptional Income-Producing Triplex Near Historic Downtown St Augustine! Rare opportunity to own an estavlished triplex ideally situated on a spacious corner lot of nearly 1/4 acre, just a 15 minute walk to the heart o downtown St Augustine.This unique property features 3 separate apartments within one building, with parking. Currently operating as a successful short-term rental, the property is projected to gross 100,000 this year with 3 years of 5 star reviews and financials supporting this. With over 7 million visitors each year and growing, this place has no problem getting booked up. Unit A 1 bed 1 bath Unit B 2 bedroom 1 bath Unit C 1 bedroom 1 bath They all have laundry w/d
Fullerwood Income -producing triplex Exceptional opportunity to own a beautiful income-producing triplex overlooking the marsh in the highly sought after Fullerwood of St Augustine. Situated on a desirable corner lot, this unique property combines character, location, privacy and impressive income history, with gross sales this year hovering around $108,000.00. The main residence offers approximately 2000 feet with 2 bedrooms and 2 baths, generous living spaces and wonderful areas for entertaining. The property also offers 2 separate apartments, each approximately 600 square feet. The upstairs unit offers 1 bedroom and 1 bath and private balcony patio with great views of the marsh. The downstairs studio include a mini kitchen with full size refrigerator and bathroom. All units have their own w/d inside. With multiple outdoor areas to entertain and BBq. Theres even a water feature. The grounds are fenced for added security and ideal for pets. Historic downtown 5 minute
253 San Marco Avenue offers a unique investment opportunity in St. Augustine. This 9-unit motel property sits directly on San Marco Avenue, just north of Historic Downtown, surrounded by hotels, vacation rentals, restaurants and some of St. Augustine’s most visited attractions. A highly visible location with plenty of possibilities for an investor looking to bring their own vision to the property and take advantage of everything this St. Augustine location has to offer.
Opportunities like this are few and far between in the highly coveted “Letter Streets” of Coquina Gables. Located just one block from the Atlantic Ocean and moments from some of St. Augustine Beach’s favorite restaurants, coffee shops, bars, and local businesses, 112 E Street offers an exceptional combination of location, lifestyle, and long-term flexibility. This beautifully updated and thoughtfully maintained property features two separate residences, Units A and B, each offering two bedrooms, one bathroom, a functional two-story townhome-style layout, and the added privacy of having no neighbors above or below. Both units feature an inviting first floor where the kitchen, living, and dining spaces flow seamlessly together, along with additional under-stair storage and direct access to covered outdoor living and fully fenced backyard spaces.
Legal grandfathered triplex Three separately metered residences 5 Bedrooms · 3 Bathrooms · 2,377 Heated Square Feet Fully furnished Private hot tub conveys Fully replumbed and fully rewired Conventional residential financing eligible Walkable Uptown / Fullerwood Park location Proven mix of short-term and long-term rental income A rare opportunity to own a legal, grandfathered triplex in Uptown St. Augustine—2 STR units are being sold fully furnished, income-producing, and eligible for conventional residential financing. Properties like this cannot be newly developed under today's zoning, making 9 Sylvan Drive as much a scarce real estate asset as it is a beautifully preserved home.
Three Detached Homes. Three Garages. One Incredible Opportunity. Situated on a prominent corner lot at Pacific Grant and Venancio, just off San Marco Avenue and only one block from US-1, this one-of-a-kind property offers the flexibility that today's buyers are searching for. Walk to coffee shops, local restaurants, cafes, and Uptown St. Augustine, with Historic Downtown, the bayfront, and all the charm of St. Augustine just minutes away. Configured as a triplex on one parcel, each residence is completely detached, providing the privacy and feel of three individual homes. Whether you're looking for a full investment property, multi-generational living, or the opportunity to live in one home while generating income from the other two, the possibilities are endless.
PRICE IMPROVEMENT **Historic Downtown St. Augustine Turnkey Investment Opportunity** Rare opportunity to own a premier income-producing property in the heart of Downtown St. Augustine's Historic Entertainment District. This beautifully maintained five-unit multifamily property is currently operating as a highly successful short-term rental with a proven track record, generating $313,000 in gross revenue in 2025. The property has outpaced most of the competition in revenue growth with last year representing a 22% increase over the past 4 years. The property consists of four spacious one-bedroom, one-bath apartments and one efficiency apartment, offering an ideal mix of accommodations for visitors seeking the charm and convenience of the Nation's Oldest City. Whether you're an experienced investor or looking to enter the thriving vacation rental market, this turnkey opportunity is ready to continue producing exceptional returns.
Historic Downtown St. Augustine Home With Detached Apartment Prime Corner Lot Abundant Parking Exceptional Flexibility! One of the lowest price-per-square-foot opportunities currently available downtown. This distinctive home offers the perfect blend of historic charm, contemporary style, and established income potential. Situated on a desirable corner lot with abundant parking -- a truly valuable advantage in the downtown area -- it is just a short walk to City Gates, St. George Street, Castillo de San Marcos, shops, restaurants, nightlife, and live music. This unique offering combines a stylish main residence with a detached income-producing apartment, providing exceptional flexibility for an owner-occupant, investor, multi-generational living arrangement, or anyone seeking a downtown lifestyle with income potential. Both spaces are currently operating as successful short-term rentals with annual gross rental income exceeding six figures.
Located in the heart of historic Uptown St. Augustine, this income-producing duplex presents an exceptional investment opportunity in one of the city's most sought-after locations. With tenants already in place, this property offers immediate rental income. Unit A is situated on the lower level and features 2 bedrooms and 1 bathroom, while Unit B occupies the upper level with 1 bedroom and 1 bathroom. The downstairs Unit B also enjoys direct access to both the front and rear porches, creating inviting outdoor spaces for relaxing and entertaining. Adding even more value, the property includes a dedicated owner's shed, providing convenient storage for tools, maintenance equipment, or personal belongings. Whether you're looking to expand your investment portfolio or own a turnkey rental property in a prime St. Augustine location, this duplex checks all the boxes. Just moments from the vibrant shops, restaurants, attractions, and waterfront that make historic Uptown so desirable, this is a rare opportunity to own an established income-producing property in one of Northeast Florida's most iconic neighborhoods.
Beachside properties are rare — one with a vacation rental license already in place is even rarer. This concrete block duplex sits just 4 houses from the beach on a lot and a half, and it's fully furnished and ready to go. Each side offers two bedrooms, 1.5 baths, a garage, a screened patio, and a rooftop deck with ocean views.
Ideally located just a short walk from vibrant Historic Downtown St. Augustine, this versatile property offers the perfect blend of charm, convenience, and investment potential. Enjoy easy access to the nation's oldest city, where cobblestone streets, iconic landmarks, unique shops, exceptional restaurants, and Flagler College are all just moments from your front door. Whether you're an investor seeking a strong income-producing property or a homeowner looking to offset your mortgage by living in one unit while renting the other, this duplex presents an outstanding opportunity. Its prime location also makes it an excellent option for housing Flagler College students. The downstairs unit features 2 bedrooms and 1 bath, while the upstairs unit offers 1 bedroom and 1 bath, providing flexible living arrangements for owners and tenants alike. Situated on a spacious lot, the property offers endless possibilities for outdoor entertaining, gardening, future expansion,
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!
Exceptional mixed-use investment opportunity on Anastasia Island, offering a rare combination of immediate cash flow, exceptional visibility, and long-term redevelopment potential. Positioned directly on A1A with outstanding frontage, this unique property spans two parcels on an oversized double-deep lot, creating a true land play in one of Northeast Florida's most desirable coastal markets. The property consists of five income-producing units with a diversified mix of commercial and residential space. The ground level features two well-maintained office suites, each offering approximately with an ADA-compliant bathroom. One of the commercial suites has been thoughtfully configured to include an additional one-bedroom, one-bathroom apartment in the rear, creating an additional residential income stream while maintaining functional commercial space. Upstairs are two spacious three-bedroom, two-bathroom residences with generous floor plans, ideal for long-term rentals, executive housing, or short-term vacation rentals. This unique blend of commercial and residential uses provides investors with multiple revenue streams while offering flexibility to adapt the property as market demands evolve. The oversized double-parcel site provides ample on-site parking, an increasingly valuable asset for both commercial tenants and residential occupants. Located just moments from the beach, restaurants, shopping, and some of Anastasia Island's most popular destinations, the property benefits from exceptional exposure, strong traffic counts, and consistent demand from both businesses and residents. Whether you're seeking a stabilized mixed-use investment, a value-add opportunity, or a strategic land acquisition along the A1A corridor, properties of this caliber rarely become available. Prime frontage, five income-producing units, flexible mixed-use configuration, multiple revenue streams, and the long-term value of a double-deep parcel combine to create an exceptional investment opportunity in one of the most sought-after locations on Anastasia Island.
Welcome to this charming duplex nestled in the heart of historic downtown St Augustine! This exceptional property offers an incredible opportunity for both investors and homeowners looking to enjoy the downtown lifestyle while generating rental income. Built in 1923 and situated in the historic district, this duplex is a quintessential piece of local history. Enjoy the convenience of living in a vibrant and culturally rich neighborhood with shops, restaurants, and entertainment options just a stone's throw away. Updated with metal roof in 2023 and ongoing maintenance make this an easy turn key property. Each unit offers 960 sf of living space and 2BR/1BA designed with one unit upstairs and one unit downstairs. As you arrive, you will be greeted by an inviting front porch that is ideal for visiting with neighbors as they pass by on their evening stroll. Step inside the downstairs unit adorned with hardwood floors to find yourself in the bright and cozy living room that flows into the dining and kitchen space, making entertaining a breeze. Down the hall you will find two good-sized bedrooms and a shared bathroom. Back onto the front porch a second door opens to stairs that lead to the upstairs unit. The living room extends to the kitchen with a breakfast bar that allows guests to spread out and chat. Two inviting bedrooms offer plenty of space and natural light with a well-appointed bathroom, ensuring residents have everything they need. Enjoy outdoor living with a back balcony for intimate gatherings and a balcony at the front where you can enjoy your morning coffee with a sunrise backdrop. You also have the option of accessing the upstairs unit from the exterior back stairs. Each unit also offers its own utility room with a washer and dryer for added convenience. Outside you will find that you have plenty of green space to have a garden, or for your resident's furry friends. With two separate units, this duplex provides an excellent opportunity for generating rental income. Welcome!
Step into a rare piece of St. Augustine history with this charming duplex built in 1885, offering a unique blend of historic character and income-producing potential. Located just minutes from the heart of downtown, this property features two separate units, making it an ideal opportunity for investors, owner-occupants, or those seeking flexible rental options. The downstairs unit is currently occupied by a long-term tenant, providing immediate and stable rental income. The upstairs unit offers versatility and can be utilized as either a long-term rental or a short-term vacation rental, allowing the next owner to maximize revenue potential based on their investment strategy. Showcasing timeless architectural details and historic charm, this property presents a rare opportunity to own an established income-producing asset in one of Florida's most sought-after historic destinations.
Exceptional investment opportunity in the heart of downtown St. Augustine! This fully renovated 4-plex is zoned for nightly rentals, offering tremendous income potential in one of Florida's most sought-after historic destinations. The property features four updated units, including two spacious 2-bedroom, 2-bath units and two well-appointed 1-bedroom, 1-bath units. All units have been renovated and are equipped with newer HVAC systems and propane tankless water heaters, providing modern comfort and efficiency for tenants or guests. Ideally located just steps from popular local destinations including The Ice Plant and St. Augustine Fish Camp, and within easy walking distance of shopping, dining, entertainment, and all the attractions that make downtown St. Augustine a year-round destination. The sale also includes the adjacent parcel at 179 Riberia Street, featuring a large garage/storage building and a multi-unit laundry facility.
Courtesy: ROMAN'S PRO REALTY LLC
407-610-1970
Step into the timeless character of Uptown St. Augustine with this beautifully restored 1920s residence, ideally situated on sought-after San Marco Avenue. Rich in historic appeal yet thoughtfully updated for modern living, this exceptional property offers a rare blend of flexibility, comfort, and investment opportunity in one of the nation’s oldest and most treasured cities. Designed to accommodate a variety of lifestyles, the home features five generously sized bedrooms and four full bathrooms across a versatile layout with two separate kitchens and living spaces. Whether utilized as one expansive private residence, a multi-generational setup, or an income-producing property, the possibilities are endless. The upper level offers three bedrooms, two bathrooms, a full kitchen, and spacious living area, while the lower level includes two bedrooms, one bathroom, its own kitchen, and comfortable gathering space. Original architectural details and vintage charm are complemented by tasteful renovations that enhance both style and functionality. Enjoy peaceful mornings and evening gatherings on the inviting wraparound porch overlooking the fully fenced yard, offering privacy and room to entertain. Ample off-street parking and a large on on site parking and gathering space and the property is being offered fully furnished for a seamless transition. Located just moments from St. Augustine’s renowned dining, shopping, attractions and waterfront scenery, this property delivers the ultimate historic downtown lifestyle. Seller states property has experienced no flooding.
IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable by is not guaranteed accurate by the MLS. Copyright 2026, St Augustine Board of Realtors. All rights reserved.
St Augustine is located in Florida. St Augustine, Florida has a population of 13,994. St Augustine is less family-centric than the surrounding county with 12.99% of the households containing married families with children. The county average for households married with children is 34.16%.
The median household income in St Augustine, Florida is $67,269. The median household income for the surrounding county is $88,794 compared to the national median of $69,021. The median age of people living in St Augustine is 46.2 years.
The average high temperature in July is 90.6 degrees, with an average low temperature in January of 45.2 degrees. The average rainfall is approximately 50.9 inches per year, with 0 inches of snow per year.
