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$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

$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

$949,000
4 Beds 2 Baths 2128943 MLS 32084 Zip Code
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

$307,000
4 Beds 1 Baths 2126671 MLS 32080 Zip Code
PRICE REDUCED! Nestled south of SR 206 on A1A, just a leisurely stroll from both the pristine beach and the tranquil Intracoastal Waterway, this charming duplex offers an idyllic coastal lifestyle like no other. Boasting a prime location and comfortable living spaces, this property presents an enticing opportunity for those seeking a beachside retreat or savvy investment. This 1200-square-footduplex offers two separate units, each with its own unique charm and character. One unit features elegant laminate wood flooring, adding warmth and sophistication, while the other boasts durable tile flooring, perfect for easy beachside living. Both units offer comfortable living areas, providing ample space for relaxation and entertaining. While the spaces are already inviting, there's room for personalization and updates to suit your taste and style. Enjoy the luxury of walking to the beach anytime you desire, whether it's for a morning stroll along the shore or a sunset picnic with loved ones.

145 Gassett Road, St. Augustine

$1,250,000
5 Beds 3 Baths 2116776 MLS 32084 Zip Code
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

$1,030,000
5 Beds 5 Baths 2114701 MLS 32084 Zip Code
Currently priced below appraised value (see listing documents), 16 Rohde Ave offers a rare opportunity to live in Downtown St. Augustine while your property helps pay for itself. Located just minutes from downtown attractions, 16 Rohde Avenue offers the perfect blend of personal residence and income-producing investment, ideal for an owner who wants to live on site while operating a successful short-term rental business. This versatile 5 (easily a 6th) bedroom, 4.5 bath property is configured as four separate units (each separately metered for water and electric). Three units operate as short-term rentals; one is leased annually and the current tenant would like to renew. A future owner can choose to occupy any unit while generating income from the others or keep it as a full rental property. Detailed operating history and revenue information are available in the attached Property Profile & Revenue Summary. A recent independent appraisal is also included in the listing documents. Live where others vacation: stroll to fine dining, boutique shopping, boating, festivals, and the famous St. Augustine Nights of Lights. Guests love the location, and the seller already has repeat visitor reservations booked into 2026, giving the next owner immediate cash flow. The current owner is committed to a smooth transition and is happy to share detailed income records with qualified buyers. Step into a turnkey operation and start earning from Day 1 while enjoying life in one of St. Augustine's most charming neighborhoods. Owner happy to provide additional operating information through 2026 and into 2027 to support buyer due diligence efforts.

16 Rohde Avenue, St. Augustine

$400,000
5 Beds 3 Baths 2113655 MLS 32086 Zip Code
Income & redevelopment play in fast-growing St. Johns County: 2.76± acres with 451' of frontage on Wildwood Dr, currently improved with two tenant-occupied manufactured homes (one double-wide and one single-wide). Do not disturb tenants. Zoning is Open Rural with Residential-C future land use, offering paths for low-density residential or a future PUD/land repositioning with appropriate approvals. Flood designation shows B/X (outside SFHA). Sold As-Is; buyer to verify utilities, zoning/use, and measurements to their satisfaction. Strong option for cash-flow investors seeking multiple households on one homesite today, with longer-term land repositioning potential as the corridor continues to develop.

1785 Wildwood Drive, St. Augustine

$505,000
3 Beds 2 Baths 2108467 MLS 32084 Zip Code
Looking for a one-of-a-kind property in the heart of St. Augustine? This original 1885 cottage with an accessory dwelling sits on a commercially zoned lot just a 15-minute walk to the Historic District or a quick drive to the beaches. Once used as crew quarters for the Florida East Coast Railway, the home has been thoughtfully restored with hardwood floors, stained-glass transoms, and modern updates. The 2-bedroom, 1-bath main cottage and 1-bedroom, 1-bath accessory dwelling each include their own washer/dryer, refrigerator, and separate A/C systems. A connecting door between the two units offers flexibility for multiple living arrangements. The accessory dwelling features a full bath, laundry center, and kitchenette, making it an ideal mother-in-law suite or private rental. Currently operated as a five star rated short-term rental, this property is both a piece of history and an income-producing opportunity in a prime location.

21 Sanchez Avenue, St. Augustine

$2,388,000
8 Beds 4 Baths 2099112 MLS 32080 Zip Code
Prime Beachside Investment Opportunity! This recently renovated 4-plex is just steps from the ocean, top-tier dining, and boutique shopping. Zoned Commercial, it offers a rare blend of income potential and flexible use—ideal for vacation rentals, long-term tenants, or even a live/work concept. Each of the four well-appointed units features 2 bedrooms, 1 bath, and a bright open-concept kitchen, dining, and living area. Guests or tenants will love the easy access to the newer heated in-ground pool, perfect for year-round enjoyment. Currently operating as a high-performing short-term rental, this property is a true turnkey income generator with endless upside. All information pertaining to the property is deemed reliable, but not guaranteed. Information to be verified by the Buyer. Be advised that cameras may exist recording audio and video inside/outside the property, such as ring doorbells. Photos are digitally enhanced and could be altered, please verify.

103 & 107 A Street, St. Augustine

$447,000
3 Beds 1 Baths 2074212 MLS 32084 Zip Code
This vintage 1940's Duplex situated on two lots is the best investment opportunity in the City of St. Augustine. Located a stone's throw from Historic Downtown in the heart of booming West Augustine, this renovated cottage with Airbnb guest house offers the perfect opportunity to step into St. Augustine life with immediate built-in income. Tucked away on the coveted and quiet Live Oak Street, walk out your front doorstep and take a leisurely stroll to enjoy the vibrant energy of West King Street with boutiques, cafes, neighborhood pubs and local brewery. Recently fully updated with modern wood-toned flooring, new roof, HVAC, kitchen, baths and more, this home offers low-maintenance urban living while maintaining Old Town charm. The oversized double lot is surrounded by towering Grandaddy live oaks and a serene backdrop of mature tropical foilage. The property offers plenty of off-street parking, privacy, room for entertaining or a pool. Whether this lucrative multi-family property is to be a full-time primary residence or income-producing investment, every bit of this charming Duplex near Historic Downtown symbolizes the quintessential St. Augustine lifestyle. Situated steps away from local favorites like Buena Onda, Bog Brewery, The West Egg and The Blue Hen, this bungalow is the perfect opportunity to create your new life in St. Augustine. Nothing Compares.

509 Live Oak Street, St. Augustine

$1,550,000
8 Beds 6 Baths 2074211 MLS 32080 Zip Code
Welcome to 307 Arricola Ave—more than just a duplex, it's a luxurious investment opportunity ready to generate income or provide a comfortable lifestyle. This property is fully furnished, turnkey-ready for short-term rentals or immediate occupancy. Built to withstand Florida's weather, this all-steel, fireproof duplex sits safely above flood levels, offering complete peace of mind against hurricanes and flooding. Step inside to discover stunning high-end LPV and tile flooring across open, inviting spaces filled with natural light. Each kitchen is a chef's delight, equipped with modern stainless steel appliances and beautiful quartz countertops. The bathrooms feature contemporary LED mirrors, and each bedroom boasts practical built-in closets, adding convenience to daily living. Both garages impress with Marble Epoxy Floors...(continued)... (...) Comfort is key with spray foam insulation throughout the property, keeping energy costs low and your living environment consistently cozy. Enjoy mornings or evenings on the inviting outdoor spaces ideal for relaxation. Perfectly located, this duplex is golf-cart accessible to the Bridge of Lions and downtown St. Augustine, where charming restaurants, unique attractions like the Historical Fort, the Amphitheater, and the Alligator Farm await exploration.

307 Arricola Avenue Unit UNIT A UNIT B, St. Augustine

$527,000
3 Beds 2 Baths 2066898 MLS 32084 Zip Code
This exceptional 110-year-old Victorian-style duplex offers a rare opportunity to own a piece of St. Augustine's history while benefiting from modern upgrades and strong rental potential. This property is zoned CM2 allowing for countless business and residential opportunities. The property showcases beautifully refurbished original hardwood floors, adding to its timeless charm and character. The downstairs unit has been fully remodeled to include granite countertops and stainless steel appliances, complementing the home's historic appeal with contemporary finishes. The spacious layout features a large bedroom with two closets, providing ample storage and comfort. The upstairs unit has also been tastefully updated with granite countertops, stainless steel appliances, and a bathroom that includes a large stand-up shower and a stunning stained glass window. Tenants will enjoy access to a full porch, which serves as an ideal outdoor living space, further enhancing the property's Tenants will enjoy access to a full porch, which serves as an ideal outdoor living space, further enhancing the property's appeal. Additional features include a large backyard, off-street parking, and a location that ensures consistent rental demand. With an excellent rental history and a design that rents easily, this property is a turnkey investment opportunity in one of Florida's most sought-after areas. Contact us today to explore the potential of this historic gem.

6 Gabriel Street, St. Augustine

$538,000
4 Beds 3 Baths 2062987 MLS 32084 Zip Code
For sale is our fully furnished property in the up and coming West St. Augustine. 24 Marion consists of two units; the main house and a back apartment that sits over two single garages. The main house is a charming 1928 3 bedroom, 2 bath house that has been successful as a mid-term and short term rental. The back apartment has enjoyed 100% occupancy with yearly leases. Opportunities abound with this property - house hack, turn apartment into a STR to increase income, bill for garage storage, or move in to the whole place and use the apartment as a guest cottage. Located 1 mile from San Sebastian Winery, this property offers an excellent opportunity. Viewing availability will be dependent on vacancy as we want to respect our guests privacy.

24 Marion Street, St. Augustine

$815,000
4 Beds 2059581 MLS 32080 Zip Code
Beautiful beachside duplex on a very quiet dead-end street at St Augustine Beach. The current owner has done extensive updating to give this home a whole new vibe. The downstairs unit is 936 Sq Ft, 2 beds, 1 bath, laundry, and backyard entertaining area. The upstairs unit is also 936 Sq Ft, 2 beds, 1 bath, laundry and a large deck. There are two driveways, one at the front and one at the side of the home. Easy two block walk to the beach and the surrounding restaurants and Pier. 10-minute drive to the historic area of St Augustine and all the great restaurants there. The current owner is doing 30-day rentals at an average of $2800 a month per unit and both units come fully furnished. The seller is a licensed FL real estate agent.

201 7th Street, St. Augustine

$820,000
4 Beds 2 Baths 2049917 MLS 32084 Zip Code
**Charming Duplex in the Heart of Historic Downtown St. Augustine!** Located just steps away from St. Augustine's iconic landmarks, including the Castillo de San Marcos, picturesque cobblestone streets, and an array of boutique shops, art galleries, and fine dining options, this beautifully maintained duplex offers an ideal blend of classic charm and modern convenience. With two well-appointed units, this property is perfect for both homeowners and investors looking for classic architecture with the historic distric. Within the property, each unit boasts generous living spaces with high ceilings, tile floor, and abundant natural light. Enjoy open-concept living areas perfect for entertaining or relaxing after a day of exploring the city. Units also feature updated kitchens with stainless steel appliances, and ample cabinet space. Both bathrooms are stylishly renovated, providing a spa-like retreat as well styling furnishings in both units (Being sold fully furnished). Exterior of the property has just been freshly painted and includes patios and porches for both units as well as ample parking while also allowing space for additional upgrades to be made. Both units are currently on a short term rental program with future bookings. As the property is zoned RG-1 it can be used for nightly rentals or long term rentals should you choose. Don't miss this rare opportunity to own a piece of St. Augustine history while enjoying the benefits of modern living. Whether you're looking for a new home, an investment property, or a vacation getaway, this duplex is a must-see!

166 Cordova Street, St. Augustine

$715,000
5 Beds 4 Baths 2049527 MLS 32080 Zip Code
109 Arricola is a pristine, turn-key property zoned RG-1 for nightly rentals! This is one of the few areas downtown that legally allows nightly rentals. Take advantage of St. Augustine's walkability with this duplex just one block from the Bridge of Lions and just steps away from shops, bars and great dining. The building is fully renovated with new luxury vinyl plank flooring and modern paint selections. The open-concept living spaces include brilliant recessed lighting and vaulted ceilings. Both kitchens have been extensively renovated to include a cooking island with counter-height seating. The gleaming quartz countertops lay atop solid hardwood cabinetry with soft-close doors and drawers. Both kitchens are equipped with modern Samsung appliances. Unit A is a three bedroom, two bathroom unit and Unit B is a two bedroom, two bathroom unit. Grossed over $94K in 2023 and on track for over $100K in 2024!

109 Arricola Avenue Unit A&B, St. Augustine

$1,100,000
5 Beds 4 Baths 2036041 MLS 32084 Zip Code
Don't miss your chance to own this fully renovated, historic multi-family gem in the heart of St. Augustine—and be sure to stop by our **Broker Open on Wednesday, April 23rd from 11AM-2PM**! Tour the property, enjoy refreshments, and enter to win a gift basket filled with local St. Augustine goodies—perfect for treating yourself or a client. Now featuring a brand new metal roof on both the main house and the Carrera Cottage, this property is turnkey and ready for your next investment move. Priced at $1,145,000—well below its appraised value—it offers incredible potential for multi-generational living, house hacking, or generating short- or long-term rental income, The main house includes 2 bedrooms and 2 baths, while the Carrera Cottage offers two private-entry 1-bedroom, 1-bath apartments with their own outdoor spaces. The Carrera Courtyard is an Instagram-worthy oasis, beautifully landscaped and designed for relaxing or entertaining. Smart home features, off-street parking, and a prime location near Flagler College and historic downtown make this a standout opportunity. Whether you're looking to invest, live in one unit and rent the others, or offer premium vacation stays, the numbers speak for themselvesprojected rental income ranges from $96,000-$120,000 for short-term and $69,600-$81,600 for long-term leases. Come experience all the charm and income potential this property has to offer!

64 Carrera Street, St. Augustine

$555,000
4 Beds 2 Baths 2037829 MLS 32080 Zip Code
Discover this updated duplex in the heart of Anastasia Island——Minutes from pristine sands, vibrant shopping and endless dining options! Situated in a highly desirable location, this property offers dual income potential. Live in one unit while renting out the other or rent both units for maximum return! Perfect for long term tenants or short term vacation rentals. Enjoy recent upgrades, including a new roof (2017), HVAC systems (2016, 2021) hot water heaters (2023, 2024) and re-pipe (2021, 2024). Embrace the St. Augustine lifestyle and seize this prime real estate investment opportunity today. Current leases through November 30, 2024. Contact us for more info and schedule your showing today!

3760 Rosewood Street, St. Augustine

$900,000
4 Beds 2006178 MLS 32080 Zip Code
Choose to reside in one unit while leasing the other or rent out both for a steady stream of income, this property provides the flexibility to suit your lifestyle and financial goals. Welcome to your beachside paradise in St. Augustine Beach, Florida! This exceptional duplex, just two houses away from the sandy shores, presents a unique opportunity for both comfortable living and savvy investment. Located steps from the beach, this duplex invites you to embrace the coastal lifestyle. Enjoy the tranquility of the ocean and the convenience of having your toes in the sand within minutes. With two well-designed units, each featuring 2 bedrooms and 1 bath, this property offers flexibility for a variety of living arrangements. The upper unit boasts a front porch with ocean views, creating a perfect spot to unwind and soak in the coastal atmosphere. Both units are currently rented, making this duplex an attractive investment opportunity.

6 C Street, St. Augustine

$1,150,000
2003264 MLS 32095 Zip Code
Opportunities abound at this amazing intracoastal front property! Located less than two miles from historic downtown St. Augustine, this 4.48 acre parcel has expansive marsh views and over 400 feet of frontage on the Intracoastal Waterway. Currently the property consists of an owner occupied 3 bed 2 bath single-family home with over 2100 square feet, 5 income generating mobile homes, and a large 27x37 detached concrete block built garage. The mobile homes are tenant occupied, have their own electrical meters, partially fenced, and some interiors were recently updated by the seller. The main house is block / frame built, has beautiful marsh views from most rooms, newer metal roof, new water heater, has been re-piped, windows replaced, new washer /dryer, and the original carport was converted into a large laundry / storage area. All dwellings on the property are on septic systems and share an artesian well with a water purification system that was rebuilt in 2021. You can keep the current configuration and live in the main house while collecting monthly rental income from your tenants in the mobile homes or re-develop the site entirely. The property is zoned Planned Special Development, so re-zoning may be required by the county for specific uses. Schedule a showing today and see what possibilities await you!

365 North Boulevard, St. Augustine

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