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 · 2,089 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.
**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.
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,
Investor's Dream by the Coast! This high-performing triplex in Crescent Beach offers an incredible opportunity just a short walk to both the river and the beach. With approx. $110K in gross income, it's ideal for short, mid, or long-term rental strategies. Each unit features its own entrance, kitchen, and private outdoor space. With a 4.9+ star Airbnb rating, a strong rental history, and consistent occupancy, this is a solid income-producing asset. Offered fully furnished with stylish interiors, it's a ready-made addition to any investment portfolio. Full financial summary available upon request.
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.
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.
At this price point, finding a home in St. Augustine Beach is rare. Finding a duplex with strong income potential is almost impossible. This concrete block, single-story property features two units, each offering two bedrooms, one bathroom, private garage, backyard space, laundry hookups, generous living areas, individual front patios, and additional off-street parking. Move right in or update each side to reflect your own style and vision. Whether you choose to live in one side and rent the other, or lease both units for an attractive return on investment, this property offers exceptional flexibility. With a complete re-pipe, 2016 roof and new windows, the hard work is done.
Upscale mixed-use townhouse with office, townhome and loft apartment. Well built structure with low maintenance. Superb amenities and tenants in place or ability to occupy yourself.
At this price point, duplexes on the island are incredibly rare--and finding one with a coveted, active short-term rental (STR) license is nearly impossible. This turnkey, fully furnished property is an absolute powerhouse. Each unit features 2 bedrooms, 2 bathrooms, an oversized driveway, and a spacious, fully fenced backyard. Tucked away on a quiet dead-end street, it offers guests a peaceful, secluded oasis that is still just an effortless stroll from the beach and the premier new dining options at Anastasia Plaza. It is no surprise this has been a stellar, high-yield income producer since 2023. Schedule your private tour today! Buyer to verify all measurements.
Just a 3–5 minute walk to Vilano Beach, this beautifully restored duplex blends coastal charm with modern updates, offering exceptional flexibility for both residential and commercial use. The property features two thoughtfully designed 2-bedroom, 1-bath units—one upstairs and one downstairs—each showcasing stylish finishes and efficient layouts. Recent upgrades include stainless steel appliances, new flooring, new windows, and fully updated electrical and plumbing systems. The downstairs unit is zoned Coastal Highway Tourist (CHT), allowing for certain types of low-impact commercial use—ideal for a boutique shop, creative studio, or small business. Upstairs, the residential unit offers a comfortable living space or income-producing rental, complete with a cozy porch perfect for relaxing outdoors.
11 Aviles Street is a fully restored mixed use property located in the heart of historic downtown St. Augustine on the oldest street in North America. The building features 18 units, including 7 commercial spaces and 11 residential apartments, all renovated between 2015 and 2023 with updated systems including HVAC, plumbing, electrical, and fire suppression. Originally the Hamlin Hardware Building, the property blends historic character with modern functionality and sits within the city’s premier art district, benefiting from strong foot traffic, tourism, and consistent demand. This is a rare opportunity to acquire a stabilized asset in one of Florida’s most iconic and high growth markets. Visit 11AvilesStreet.com for for more details.
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!
A rare opportunity to own a duplex just steps from the beach in the heart of St. Augustine Beach. 207 9th St offers a highly functional layout with two mirrored units, each featuring three bedrooms and one bathroom, creating a versatile setup for a wide range of living situations. The upstairs unit was fully renovated in 2021, is vacant and move-in ready, while the downstairs unit is well appointed with white shaker cabinets, granite countertops, and hardwood flooring throughout. Whether you are looking to house hack and offset your monthly expenses, create a multigenerational living setup with privacy between spaces, or simply enjoy the flexibility of a separate living area for guests or extended family, this property delivers. Major updates have already been taken care of: both units connect to city sewer and a metal roof was installed in 2018, giving you a solid and low-maintenance foundation.
Welcome to your dream investment at 9 Sevilla St and or multi generational living. Historic downtown St. Augustine in the heart of everything, just steps from Flagler College, shopping, dining, and historic attractions. This fully furnished property is an established and highly productive VRBO/Airbnb income property all 5-star. Another bonus a pool opportunity: as proposed 8' x 16' swimming pool has been preliminarily approved design to meet current setbacks requirements. This offers buyers the opportunity to have a private outdoor retreat. Design sketches and AI enhanced drawing...see pics in listing. This exceptional property features three beautifully appointed units each thoughtfully designed with comfort, luxury, historic charm in mind. The ground-floor unit offers two spacious bedrooms, w/3 baths with luxe amenities, vaulted ceilings, and spectacular hardwood floors that create warmth and elegant atmosphere.
Rare investment opportunity in the heart of St. Augustine Beach! This mixed-use property offers stable income at a prime location just a short walk from the ocean, local dining, and shopping. Upstairs level includes two well-maintained apartments, each with 2 bedrooms and 1 bathroom, ideal for long-term rentals or vacation income. The ground floor features three commercial spaces, all fully occupied with established tenants, providing reliable rental income from day one. Property was just painted Feb of 26’ , property has impact glass throughout with roof, gutters and full apartment upgrades in 2015 With excellent street visibility, high year-round foot traffic, and close proximity to the beach, this property is perfectly positioned for continued growth and strong returns. Whether you’re seeking a turnkey income property or a long-term investment in one of Florida’s most desirable coastal communities, 711 A1A Beach Blvd checks all the boxes.
Step into a rare offering where timeless architecture, rich history, and modern opportunity converge. Nestled on a lush, maturely landscaped .30-acre corner parcel with abundant parking, this extraordinary multi-unit estate has been lovingly held within the same family since 1951—an enduring testament to its character and charm. At the heart of the property stands the iconic 24 & 26 Saragossa duplex; a two-story Mediterranean Revival residence (circa 1910–1914), originally constructed by C. M. Milburn of St. Augustine. Each residence offers approximately 2,152 square feet of conditioned living space, featuring 3 bedrooms, 1 full bath, and 1 half bath. From the moment you arrive, the double front staircases with ornate cast iron railings set the tone for the craftsmanship found throughout. This property is among the highest elevation in the area and the home sits well above most downtown homes offering further resiliency as the living spaces have never flooded.
Price Adjustment! Desirable duplex just a hop, skip and a plunge from St. Augustine Beach! Experience effortless coastal living and dependable rental income in this inviting duplex, set on one of the area’s most sought-after numbered streets. The property offers two generously sized 3-bedroom, 1-bath residences, thoughtfully maintained and surrounded by refreshed landscaping. Expansive backyard, and ample parking elevate both comfort and value. With long-term tenants already in place, this property stands as a rare opportunity to own a refined, income-producing asset in one of St. Augustine’s most desirable coastal neighborhoods.
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.
