Refine Search
Map
Sort by
$1,295,000
264009 MLS ⋅ 32084 Zip Code
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.

1 E San Carlos Ave, St Augustine
$1,150,000
263952 MLS ⋅ 32080 Zip Code
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

120 Anastasia Lodge Dr, St Augustine
$740,000
263893 MLS ⋅ 32084 Zip Code
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.

6 E San Carlos Ave, St Augustine
$824,000
263803 MLS ⋅ 32084 Zip Code
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

8 Douglas Ave Unit A,B & C, St Augustine
$849,000
263774 MLS ⋅ 32084 Zip Code
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

35 Atlantic Ave Unit A,B & C, St Augustine
$1,350,000
263764 MLS ⋅ 32084 Zip Code
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.

253 San Marco Avenue, St Augustine
$779,900
263572 MLS ⋅ 32084 Zip Code
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.

9 Sylvan Dr, St Augustine
$1,550,000
263538 MLS ⋅ 32084 Zip Code
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.

10 Pacific, St Augustine
$1,740,000
263419 MLS ⋅ 32084 Zip Code
**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.

16 Mulvey St, St Augustine
$1,495,000
263273 MLS ⋅ 32080 Zip Code
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.

11 B St Unit A and B, St Augustine
$649,000
263255 MLS ⋅ 32084 Zip Code
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,

69 Saragossa St, St Augustine
$800,000
7 Beds ⋅ 5 Baths ⋅ 2154685 MLS ⋅ 32080 Zip Code
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.

7018 Middleton Avenue, St. Augustine
$1,450,000
6 Beds ⋅ 2154005 MLS ⋅ 32084 Zip Code
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
$1,150,000
7 Beds ⋅ 5 Baths ⋅ 2153565 MLS ⋅ 32080 Zip Code
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.

5961 A1a S, St. Augustine
$1,150,000
263137 MLS ⋅ 32080 Zip Code
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.

5961 A1a, St Augustine
$925,000
262960 MLS ⋅ 32086 Zip Code
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.

14 Sanchez Avenue, St Augustine
$630,000
262919 MLS ⋅ 32084 Zip Code
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.

8 Mulvey Street, St Augustine
$1,699,900
262794 MLS ⋅ 32084 Zip Code
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.

177 Riberia St, St Augustine
$975,000
6 Beds ⋅ 4 Baths ⋅ 2149236 MLS ⋅ 32080 Zip Code
OWNER MOTIVATED! BRING OFFERS! Rare opportunity to own the only currently listed duplex in St. Augustine Beach featuring two spacious 3BR/2BA units, each with its own garage, private entrance, and in-unit laundry. With six total bedrooms, this property offers exceptional income potential and flexibility for short-term rentals (30 days per licensing), long-term tenants, multigenerational living, or owner-occupancy with rental income. Offered fully furnished and located on a quiet dead-end street just a short walk to the beach, this turnkey property combines strong investment potential with an unbeatable coastal lifestyle. Historic Downtown St. Augustine, restaurants, shopping, and attractions are only minutes away. Extensively renovated, the property features Hardie Board siding, a newer roof, HVAC systems with Nest thermostats, updated electrical panels, repiped plumbing, newer water heaters, connection to county sewer, LVP flooring, granite countertops, stainless steel appliances, updated bathrooms, keyless entry systems, and more. The downstairs unit offers a screened lanai and fenced yard, while the upstairs unit enjoys a spacious balcony perfect for enjoying the coastal breeze. County sewer connection is already in place, eliminating the maintenance concerns often associated with older beach properties. Flood zone X (no flood insurance required) & there is no history of flooding. An adjacent parcel at 14 Ewing Street is available separately and may be negotiated with the sale. Turnkey, furnished, and ready for its next owner in one of Northeast Florida's most desirable beach communities.

16 Ewing Street, St. Augustine Beach
$869,500
4 Beds ⋅ 5 Baths ⋅ 2147913 MLS ⋅ 32095 Zip Code
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.

544 Market Street, St. Augustine
$905,000
3 Beds ⋅ 3 Baths ⋅ 2147750 MLS ⋅ 32084 Zip Code
Turnkey Triplex in the Heart of Historic St. Augustine. Fully Remodeled, Fully Furnished & Proven Income Producer From Day One. Every inch of this 1920-built property has been thoughtfully updated new finishes, updated systems, and a design sensibility that earns the kind of five-star reviews that keep the calendar full. With $130,000-$150,000 in proven gross annual STR revenue, the numbers speak for themselves. The reviews back it up. The repeat guests prove it. Sold fully furnished, this is a true plug-and-play investment. Walk in, hand over the keys, and let it work for you or hold it for personal use and let it pay for itself when you're not there. Step outside and you'll find one of the property's most exciting untapped opportunities: a generous yard with seri

9 Saragossa Street, St. Augustine
$710,900
4 Beds ⋅ 4 Baths ⋅ 2146405 MLS ⋅ 32080 Zip Code
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.

6 Lisbon Street Unit A/B, St. Augustine
$590,000
262455 MLS ⋅ 32080 Zip Code
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.

15 Atlantic Oaks Circle, St Augustine
$889,500
261990 MLS ⋅ 32084 Zip Code
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.

105 Beachcomber Way, St Augustine
$9,750,000
261951 MLS ⋅ 32084 Zip Code
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.

11 Aviles Steet, St Augustine
$1,450,000
261941 MLS ⋅ 32084 Zip Code
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 St, St Augustine
$705,000
261901 MLS ⋅ 32080 Zip Code
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.

207 9th St, St Augustine
$1,749,000
261546 MLS ⋅ 32084 Zip Code
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.

9 Sevilla Street, St Augustine
$1,963,000
261367 MLS ⋅ 32084 Zip Code
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.

24 Saragossa St, St Augustine
$725,000
261317 MLS ⋅ 32080 Zip Code
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.

203 9th Street, St Augustine
© 2026 Northeast Florida Multiple Listing Service, Inc. All rights reserved. This data is up-to-date as of . For the most current information, contact Real Estate Company.