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$375,000
3 Beds 2 Baths 2117260 MLS
Thoughtfully renovated mid-century cottage meets innovative modern design by Blackbox Design LLC. Located a stone's throw from Historic Downtown, walk out your doorstep and take a leisurely stroll to enjoy the vibrant energy of the West King District. Sip your coffee in the morning in the front sunroom with views of sparkling water on Oyster Creek. With three bedrooms, two baths and a chic modern addition added in 2005 featuring soaring vaulted ceilings and a loft space, ready for your ideas. Enjoy additional drywalled garage space ready for conversion to your home office, workshop or family room. Open the dueling utility doors on a sunny Florida day allowing for cross breezes from Oyster Creek. Interior seamlessly blends with the European-style courtyard, lush with mature bougainvillea and tropical foliage, perfect for entertaining. Exterior beams and framing in place to add a door and garden balcony off of the loft space. Separate modern storage shed ~ easily convert to garden cabana/studio. Whether this home is to be a full-time residence, part-time getaway or income-producing, every bit of this charming cottage near Historic Downtown symbolizes the quintessential St. Augustine lifestyle. Situated steps away from local favorites like Buena Onda, Bog Brewery, Mugsy's Bar, The Local Refillery and The Blue Hen, this mid-century modern bungalow is the perfect opportunity to create your new life in St. Augustine. Nothing compares.

5 Carey Street, St. Augustine

Listing courtesy of ONE SOTHEBY'S INTERNATIONAL REALTY.

Selling Office: .

$300,000
3 Beds 1 Baths 2117147 MLS
Just steps from Historic Downtown St. Augustine, this 1900s Southern Bungalow in the heart of booming West Augustine is a true unicorn property. The oversized lot offers endless potential to expand or add a pool and/or ADU, creating the ultimate investment or multi-generational forever home. Enjoy the charm of Old Florida with a detached garage, mature trees, and room to grow in one of St. Augustine's most sought-after neighborhoods. Walk to the vibrant West King District filled with local boutiques, cafes, yoga studios, pubs, and a neighborhood brewery, or take a peaceful stroll along Oyster Creek. This is a rare chance to create a mini compound in the nation's oldest city. Bring your craftsmanship and vision to make this family estate your own and capture a piece of historic St. Augustine charm. Some images are edited, Buyer to verify all information.

10 Clark Street, St. Augustine

Listing courtesy of ONE SOTHEBY'S INTERNATIONAL REALTY.

Selling Office: .

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

62 1/2 Valencia Street, St. Augustine

Listing courtesy of IHEART REALTY INC.

$1,250,000
3 Beds 3 Baths 2116690 MLS
Timeless Elegance Meets Modern Luxury in the Heart of St. Augustine. Welcome to 31 Cincinnati Avenue, a rare opportunity to own an exceptional piece of St. Augustine's architectural heritage. Originally built in 1910 and thoughtfully expanded in 2015, this distinguished residence offers nearly 2,700 square feet of refined living space, gracefully positioned on a .30-acre double lot in the coveted Uptown district, just a short stroll from historic downtown. With short-term rental eligibility, the property presents an equally compelling opportunity as a private estate or a luxury investment. Inside, soaring ceilings, original yellow heart pine floors, and artisan-crafted millwork honor the home's historic character, while carefully curated modern enhancements provide contemporary comfort and functionality. The welcoming foyer showcases an elegant bay window and period woodwork, leading to a sweeping staircase and light-filled interiors that unfold with timeless charm. The gourmet kitchen is a chef's masterpiece, featuring custom cabinetry, a generous center island, a professional-grade Italian six-burner gas range with griddle and double ovens, a wine refrigerator, and a spacious walk-in pantry. A charming Dutch door opens from the kitchen to the expansive wraparound porch, creating seamless indoor-outdoor living ideal for both entertaining and everyday enjoyment. The adjoining family room impresses with a dramatic cathedral ceiling, floor-to-ceiling built-ins, and French doors with transom windows, bathing the space in natural light. The first-floor primary suite offers a tranquil private retreat, highlighted by 13-foot-plus ceilings, a spa-inspired bath with soaking tub and oversized walk-in shower, a dual-basin vanity, and three generous closet spaces. Upstairs, two spacious bedrooms share a beautifully remodeled bath appointed with a jetted tub/shower combination and a custom vanity, providing comfort and elegance for family or guests. Outdoors, the fully fenced and gated grounds offer exceptional privacy and charm, anchored by a magnificent magnolia tree dating back to the 1800s. The property is further enhanced by an oversized two-car concrete block garage with abundant storage and convenient rear alley access. Additional highlights include a newer architectural shingle roof, updated electrical and plumbing, and a transferable termite bond, ensuring peace of mind. Blending historic craftsmanship with modern sophistication, this remarkable residence is a true gem in one of Florida's most storied and desirable cities.

31 Cincinnati Avenue, St. Augustine

Listing courtesy of KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE.

Selling Office: .

$462,500
3 Beds 3 Baths 2116638 MLS
Investors!!! 3-bed multi-family in Crescent Beach, St Augustine FL just 2 blocks from the ocean. Property features a 1-bed, 1-bath cottage (660 sqft) and a 2-bed, 2-bath apartment (923 sqft) above a detached garage. Located on a corner lot with ample parking, it offers strong potential for short-term rental or dual occupancy. The 1942 cottage brings vintage character and flexible use, while the upstairs apartment adds extra square footage and function, sitting atop a 2-car garage with a 2023 metal roof. Both units have private entrances and are currently vacant, ready for cosmetic updates or rental setup. With no HOA, plenty of parking, and separation between units, investors can maximize flexibility. Just 2 blocks from the beach and minutes from SR-206, the location provides easy access to I-95, local dining, and St. Augustine attractions. Whether you're seeking a beach rental, multi-unit investment, or project with upside, this Crescent Beach property checks the boxes.

6951 Middleton Avenue, St. Augustine

Listing courtesy of FIV REALTY CO FLORIDA LLC.

Selling Office: .

$1,100,000
2116538 MLS
This 4,116 sq. ft. office building features 120 feet of frontage along San Marco/A1A and includes a covered patio. The property offers 3,540 sq. ft. of heated and cooled space, currently divided into three office suites, each with private entrances. With 17 on-site parking spaces, this property presents endless opportunities for establishing your own business in the heart of downtown St. Augustine. Suite A: 3 offices, reception area, waiting room, and half bath. Currently leased on a month-to-month basis. Suite B: 2 offices, reception area, and shared access to a conference room and full bathroom with Suite C. Suite C: 2 offices, reception area, half bath, copy/storage room, and shared access to the conference room and full bath with Suite B. Additional features include a large, high-visibility sign on the front and City of St. Augustine water and sewer services. This property offers a fantastic opportunity for a variety of businesses!

222 San Marco Avenue, St. Augustine

Listing courtesy of LIGHTHOUSE REALTY ASSOCIATES.

Selling Office: .

$1,030,000
5 Beds 5 Baths 2114701 MLS
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

Listing courtesy of FIRST COAST PREMIER PROPERTIES.

Selling Office: .

$718,000
4 Beds 2 Baths 2114532 MLS
Nestled amongst the moss draped oaks on the iconic Magnolia Avenue, discover this 1949 cottage fully renovated with modern comforts while maintaining its vintage charm. Currently operating as a 5-Star Airbnb with glowing reviews and current bookings into 2026. It's also an ideal location for a full-time residence or weekend retreat-just blocks from the city's beloved shops and restaurants in the historic Uptown district. This 4-bedroom, 2-bath residence was thoughtfully restored in 2023 with new roof, AC, plumbing, electrical, windows, and adorable kitchen with modern amenities. Dining room opens to living room and extra family room allows plenty of space for everyone. Sip coffee or cocktails on the front porch where you can sometimes catch a glimpse of the peacocks meandering back to the Fountain of Youth. Covered porch & patio in the backyard ideal after a day exploring the city or relaxing at the beach (just over the Vilano bridge). Off-street parking.

42 Magnolia Avenue, St. Augustine

Listing courtesy of HERRON REAL ESTATE LLC.

Selling Office: .

$565,000
2 Beds 2 Baths 2113908 MLS
FULLY FURNISHED. Step into timeless charm at 179 Blanco St, a beautifully restored 1910's home nestled in the heart of St. Augustine. This 2-bedroom, 2-bath gem perfectly blends historic character with modern comfort. Enjoy peace of mind with a new roof (2022), new HVAC system (2025), and updated plumbing and electrical. The spacious, fenced-in yard offers plenty of room for outdoor gatherings, complemented by a large deck ideal for entertaining. Inside, natural light fills the inviting living spaces, featuring original details that reflect the city's rich history. Located just minutes from downtown St. Augustine, residents can explore nearby boutiques, cafés, and historic landmarks. Whether you're seeking a charming full-time residence, a weekend retreat, or an investment property, this home captures the best of old-world character and modern living—just a short drive from the area's pristine beaches.

179 Blanco Street, St. Augustine

Listing courtesy of COMPASS FLORIDA LLC.

Selling Office: .

$525,000
2113857 MLS
Rare opportunity in downtown St. Augustine to own a charming 1910 historic cottage with flexible residential potential. Located just steps from King Street and Flagler College, this freestanding property offers excellent walkability, on-site parking, and a welcoming front porch. The interior is currently configured for office use with multiple private rooms, a kitchenette, and a restroom, offering an ideal setup for a buyer seeking a live/work opportunity, residential conversion, or unique downtown residence. Recent system updates include a 2022 garage roof and HVAC replacements completed between 2018-2022. Zoned for Commercial/Residential/Office use; buyer to verify intended use with the City of St. Augustine.

77 Saragossa Street, St. Augustine

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES, FLORIDA NETWORK REALTY.

$245,500
1 Beds 1 Baths 2113789 MLS
Experience peaceful country living in this solid concrete block built home perfectly positioned on a spacious, beautifully landscaped lot across the street from the St. Johns River. Enjoy serene views, mature trees, and a quiet setting with no HOA. Inside, you'll find a bright, open floor plan featuring no carpet, wood-planked ceilings with exposed beams, and a durable metal roof that adds both charm and longevity. The front porch is the perfect spot to unwind and take in the natural surroundings, while convenient in-unit laundry adds everyday ease. Just a few hundred yards away, you'll find a riverfront park with a public boat ramp—ideal for boating, fishing, or simply enjoying the water. With its tranquil setting, solid construction, and unbeatable location, this home offers a rare chance to enjoy the peaceful St. Johns River lifestyle, only a short drive from historic downtown St. Augustine, shopping, and dining. Call or text to schedule your tour!

1208 County Road 13 S, St. Augustine

Listing courtesy of LOKATION.

Selling Office: .

$560,000
3 Beds 3 Baths 2113745 MLS
Welcome home to your walkable lifestyle in the nations oldest city...meet our most eligible southern belle...over 125 years old and never flooded, she has original heart of pine floors and glorious stained window accents. The modernized kitchen has been totally brought up to code and has double ovens for the baker in your life. Modern conveniences like plantation shutters throughout only enhance her charm. The primary suite is so large you have enough room for a home office inside. Not to mention the walk in closets and soaking tub...the whole home balcony off the primary would be perfect for gardening and entertaining. The fenced back yard is made for fires in the fire pit or grilling out. Let's talk about how close you are to everything here...you are half a mile to the foot of the Bridge Of Lions and less to the Fort. This catch also has a nightly rental permit so she can earn as an Airbnb too!! Homes like this one don't come along often, come own your part of history today!

29 Grant Street, St. Augustine

Listing courtesy of MAXREV, LLC.

$2,800,000
7 Beds 5 Baths 2112505 MLS
Step into the enchanting embrace of the notable Upham Winter Cottage, a captivating Queen Anne Victorian nestled on a quarter-acre lot within the heart of St. Augustine's cherished historic preservation district and listed on the National Register ofHistoric Places. This world-class historic mansion has recently been renovated from top to bottom to perfection with soft coastal hues in mind ~ enjoy the well-designed balance of rich historic beauty and modern luxury. With 5800 sq ft of living space, 5 bedrooms and 3.5 bathrooms in the main house and a 2 bedroom, 1 bath apartment with private entrance, a full kitchen, living and dining room - this home is ideal for multigenerational living or additional income. Located on historic St.George Street, the shops, restaurants, landmarks and culture of the Nation's Oldest City are only steps away. The highly active community association provides additional opportunities to socialize and enjoy the buzz of downtown living Built in 1893 as a winter retreat for John J. Upham, a veteran of the Civil War and Plains Indian War, this remarkable home showcases the graceful blend of Queen Anne Victorian architecture with examples of Moorish Revival in the courtyard arches. With stunning original millwork, wood floors and a unique octagonal shape, this home will take you back to the splendor of the Gilded Age. From joyous Flagler Era galas to legendary Mardi Gras celebrations, The Upham Winter Cottage has been a witness to countless extraordinary events throughout the ages. Today, as you step foot within these storied walls, you become a part of the Upham Winter Cottage's narrative and assume the role of its guardian, preserving the heritage of the past while crafting a new chapter in its history. Nothing compares.

268 St George Street, St. Augustine

Listing courtesy of ONE SOTHEBY'S INTERNATIONAL REALTY.

$820,000
3 Beds 3 Baths 2112166 MLS
Step into the Uptown St. Augustine lifestyle in this beautifully renovated colonial home situated in the Historic Fullerwood neighborhood. Enjoy the best cafés, boutiques, and nightlife on nearby booming San Marco Avenue in the Nation's Oldest City. This 1920's gem exudes the charm and character of yesteryear, with original doors, hardware, elegant fireplace and hardwood pine floors. Entertain friends and family in the grand gourmet kitchen featuring additional dining area and a modern coffee and wine bar, leading out to the courtyard garden, with an ambience reminiscent of Old Florida. Updates include Thermador and Bosch appliances, a 54" refrigerator and freezer, six-burner professional range, quartz countertops, stacked cabinetry, custom tile, and a nine-foot island. A custom-designed coffee and wine bar with sink, wine cooler, and professional Rancilio espresso machine completes the space. The home also features a dedicated office or sunroom, colorful custom stained-glass windows, updated bathrooms with designer fixtures, a luxurious primary bath with heated Toto bidet toilet and a custom California Closet, plus a guest bath with antique clawfoot tub. Additional improvements include a newer roof, two HVAC units, upgraded plumbing and electrical, new motorized blinds, a water softener, irrigation system with deep artesian well, and professionally designed landscaping. The porches and driveway have all been updated, including a paver drive with ample parking. The coveted Fullerwood neighborhood offers an eclectic mix of new and old homes, and its character is defined by a community playground, garden, and preservation of cultural resources. Conveniently located minutes from Vilano Beach and historic downtown, yet tucked away in a tranquil setting, 238 Rainey offers the perfect balance of history, modern comfort, and the vibrant lifestyle of Uptown St. Augustine. Nothing Compares.

238 Rainey Avenue, St. Augustine

Listing courtesy of ONE SOTHEBY'S INTERNATIONAL REALTY.

Selling Office: .

$485,000
3 Beds 2 Baths 2112148 MLS
Don't miss the opportunity to own a piece of historic charm with this 3-bedroom, 2-bath 1925 bungalow, located in one of Uptown's most desirable and rapidly growing neighborhoods. Whether you're a homeowner with a vision or an investor seeking your next project, this property offers incredible potential! Features include a spacious screened front porch, original hardwood floors throughout most of the home, a vinyl-fenced backyard, and an exterior shed with an attached workshop—perfect for storage or hobby space. Additional off-street parking adds convenience and value. This property is a rare opportunity in a sought-after location with strong long-term potential. Bring your creativity and finishing touches to transform this fixer-upper into something truly special! Schedule your showing today and see the potential for yourself. Buyer is responsible for doing all due diligence when considering. Vacant and easy to show! Home is zoned RS-2. Home was temporarily taken off the market to be tented for termites on 9/22.

4 Fletcher Lane, St. Augustine

Listing courtesy of MAXREV, LLC.

$1,700,000
4 Beds 4 Baths 2112045 MLS
Historic elegance meets modern living on Water Street. It's not often a house like this comes available - a thoughtfully renovated 1872 residence in the heart of St Augustine's coveted Abbott Tract. Located on this picturesque street, the two-story residence offers the perfect blend of classic charm and contemporary comfort, all just steps from the Castillo de San Marcos, downtown St Augustine, the bayfront, and the vibrant uptown district. Set on a deep lot, this home offers a gated driveway with dedicated parking. Brick steps lead you to the inviting covered front porch, where a solid antique wood door is framed by dual French doors opening to both the living room and family room. Step into the foyer and be greeted by original heart pine floors and staircase, lovingly preserved during the home's top-to -bottom renovation in 2019. To your right, a formal sitting room opens to a sunlit dining area, both overlooking the open -concept chef's kitchen, complete with modern finishes and thoughtful design. On the left, the family room flows easily into the main dining and kitchen spaces. A half bath, storage room, and mudroom entrance complete the first floor. Step outside to your private retreat: a fully fenced backyard designed for both entertaining and leisure. Completed in 2020, the space features low-maintenance artificial turf, a bocce ball court, stone seating areas and a deliciously inviting pool. Practice your short game on the custom putting green, or simply unwind under the Florida sky. Upstairs, two guest bedrooms share a full bath, while a spacious junior suite includes its own private bathroom with a walk-in shower. At the east end, the primary suite offers a tranquil sanctuary with two balconies, a private sitting area, peeks of the Matanzas River, and a generous bathroom featuring a modern clawfoot tub, walk-in shower, double vanity, and walk-in closet. This is more than a home - it's a legacy, a lifestyle, and a chance to live in one of St Augustine's most treasured neighborhoods.

56 Water Street, St. Augustine

Listing courtesy of ONE SOTHEBY'S INTERNATIONAL REALTY.

Selling Office: .

$245,000
3 Beds 2 Baths 2111555 MLS
This concrete block home in St. Augustine offers durability, low maintenance, and modern comfort. New windows, updated lighting, and luxury vinyl plank flooring create a bright, clean interior. The kitchen features stainless steel appliances, butcherblock counters, and crisp cabinetry that support everyday living and easy entertaining. The primary bedroom includes a private bath with a shower. Two additional bedrooms provide space for family or guests. A flexible bonus room can serve as an office, playroom, fitness space, or optional fourth bedroom. The backyard offers a quiet place to relax outdoors. The home is minutes from St. Augustine Beach, historic downtown, local restaurants, shopping, and daily conveniences. Move-in ready and well located, this property delivers strong value in one of Northeast Florida's most desirable coastal markets. The fully fenced backyard offers space to relax, garden, or let pets play. Just minutes from the restaurants, shops, and historic charm of downtown St. Augustine, and a short drive to the beach, this home makes it easy to enjoy the coastal lifestyle. Preferred lender offering up to 1% of the purchase price toward buyer's prepaids and closing costs.

243 Ravenswood Drive, St. Augustine

Listing courtesy of COLDWELL BANKER VANGUARD REALTY.

Selling Office: .

$430,000
3 Beds 2 Baths 2110736 MLS
Now offering $5k towards interest rate buy down!! Freshly remodeled and full of charm, this 3 bedroom, 2 bath home offers a rare opportunity to live or invest in one of St. Augustine's most walkable and desirable locations. Step inside to discover updated kitchen and baths, modern finishes, and a move-in ready feel that blends comfort with character. Whether you're sipping coffee before strolling to local shops and restaurants or welcoming guests for a weekend stay, this home supports both lifestyle and flexibility. Short-term rental use is allowed, making it an exciting option for those looking to enjoy the property while also exploring income potential. With the historic waterfront just moments away and downtown energy right outside your door, this is a special chance to own a piece of St. Augustine's story.

165 Blanco Street, St. Augustine

Listing courtesy of NEXTHOME ENDLESS SUMMER.

Selling Office: .

$545,000
2 Baths 2109603 MLS
Tucked beneath a canopy of majestic live oaks, this private 3.50-acre property offers Old Florida beauty just minutes from historic downtown St. Augustine. Long known as the site of Price's Oyster House, a beloved landmark now closed, the property blends natural seclusion with in-town convenience. This 3.50-acre single parcel offers a rare blend of privacy and easy access along Wildwood Drive. Future Land Use: Residential-C (RES-C). Current Zoning: Open Rural (OR), no assumptions of commercial up-zoning. Excellent option for an estate/compound buyer or a small builder seeking 1-acre homesites (subject to County approvals). On-site ''interim improvements'' include two residences and multiple shop/garage outbuildings, use for storage, staging, or occupancy while you plan. Utilities: well/septic area; buyer to verify availability/extension of any central service. Three structures convey.

1774 Wildwood Drive, St. Augustine

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES, FLORIDA NETWORK REALTY.

Selling Office: .

$545,000
5 Beds 2 Baths 2109485 MLS
Tucked beneath a canopy of majestic live oaks, this private 3.50-acre property offers Old Florida beauty just minutes from historic downtown St. Augustine. Long known as the site of Price's Oyster House, a beloved landmark now closed, the property blends natural seclusion with in-town convenience. Three structures convey: the main 1964CBS home (1,328 sf, 2BR/1BA), a 1961 wood-frame residence (922 sf, 2BR/1BA), and the original Oyster House building (364 sf), full of character and history. A large pool, garage workshop, and shed provide space for hobbies, storage, and projects, with plenty of room to create your vision. A 2025 boundary survey clearly defines the approximate 3.50-acre tract, showing the homes, pool, and outbuildings. The land is zoned Open Rural (OR) with RES-C FLUM, allowing for single-family, modular, and mobile homes. Sold as-is, this unique offering is perfect for those seeking privacy, history, and opportunity.

1774 Wildwood Drive, St. Augustine

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES, FLORIDA NETWORK REALTY.

Selling Office: .

$505,000
3 Beds 2 Baths 2108466 MLS
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

Listing courtesy of KELLER WILLIAMS ST JOHNS.

Selling Office: .

$505,000
3 Beds 2 Baths 2108467 MLS
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

Listing courtesy of KELLER WILLIAMS ST JOHNS.

Selling Office: .

$437,500
2 Beds 2 Baths 2104848 MLS
This move-in-ready 1920s gem is nestled in the heart of the highly desirable Lighthouse Park community in St. Augustine. Beautifully renovated, this 2-bedroom, 2-bath home blends vintage charm with modern comfort, offering two private en-suites, a spacious 400-square-foot back deck, and a true island lifestyle just steps from the iconic St. Augustine Lighthouse. Inside, you'll find gorgeous bamboo floors, granite countertops, barn doors, penny tile, stainless steel appliances, maple wood ceilings, and fresh interior paint. The kitchen and bathrooms have been thoughtfully updated, and key system upgrades include a metal roof (2016), HVAC replacement in 2020, plus updated plumbing, and a water heater replaced just before August 2016. Exterior improvements include updated paint, fencing, and a storage shed. The fully fenced yard features an outdoor shower and ample space for boat parking. The home is located in flood zone X and is connected to the sewer. Additional peace of mind comes with a one-year home warranty and a termite bond already in place. Enjoy unbeatable walkabilityjust a short stroll to R.B. Hunt Elementary, the Amphitheatre, local eateries, and the public beach launch, with Anastasia State Park just a bike ride away. Whether you're seeking a full-time residence, second home, investment property, or weekly rental, this home is all about living the beach lifestyle in one of St. Augustine's most vibrant coastal neighborhoods.

19 Palmetto Avenue, St. Augustine

Listing courtesy of FIV REALTY CO FLORIDA LLC.

Selling Office: .

$535,000
2 Baths 2106741 MLS
Prime West Augustine Commercial Property with Unlimited Growth Potential! This historic investment property has been an iconic and favorite gathering place for locals and tourists alike for many years. Located in the heart of the trendy WestAugustine district, within the Historic City limits, this property offers a rare mix of immediate income and future growth potential. Zoned CL-1 and spanning three lots, it's an ideal opportunity for restaurant/office entrepreneurs, investors, or developers. The existing building is designed to seat 50+ guests, featuring indoor and outdoor dining areas, a welcoming front porch, two entrances, two bathrooms, and ADA accessibility. Two off-street parking areas provide approximately 30 parking spaces, offering convenience for both patrons and staff. Recent upgrades include updated wood lap siding, exterior paint, window frames, interior paint, a modern grease trap, signage, and an on-site storage shed. Beyond its current use, the additional land allows for a multitude of possibilities: build another structure, create an income-producing nightly vacation rental, or construct a private residence on the back lot. This flexibility makes the property valuable both for today's operations and tomorrow's investment. This offering is for the real estate only, with business and restaurant equipment are negotiable separately. Owner financing is available. Please do not approach the tenant. ***Contact us today for details and to schedule a private tour of this notable historic commercial property.

40 S Dixie Highway, St. Augustine

Listing courtesy of ONE SOTHEBY'S INTERNATIONAL REALTY.

Selling Office: .

$645,000
4 Beds 2 Baths 2104990 MLS
Lincolnville Gem - 4BR/2BA Discover 'Oak Tree Retreat', a beautifully updated 4-bedroom, 2-bathroom residence in the heart of St. Augustine's historic Lincolnville. Seamlessly blending historic charm with modern comfort, this home is just a short stroll from Flagler College, the lively St. George Street, museums, parks, shops, and acclaimed restaurants. Recent upgrades include custom closets, a kitchen island, LVP flooring in bedrooms, and a tiled shower, complementing the earlier renovations of a new roof, HVAC, kitchen, baths, windows, doors, and tile flooring (2013-2014). A proven success as both a short-term and long-term rental, this property offers many options as an exceptional investment opportunity, a college residence, or a stunning primary residence. Enjoy the tranquil ambiance of the neighborhood from your private upstairs porch and immerse yourself in the vibrant historic character, attractions, and coastal lifestyle of St. Augustine. Don't miss this rare opportunity!

121 Martin Luther King Ave Avenue, St. Augustine

Listing courtesy of ORANGE REALTY PROFESSIONALS.

Selling Office: .

$255,000
3 Beds 1 Baths 2106209 MLS
Completely Renovated & Minutes from Downtown St. Augustine This move-in-ready property has been upgraded from top to bottom, including: Brand New Roof, HVAC & Ductwork,, Electrical, Plumbing, Kitchen Cabinets, Quartz Countertops, Bathroom, Interior and Exterior Paint, Septic, and Well Pump - giving you peace of mind for years to come. Sitting on a massive .35-acre lot, there's plenty of room to enjoy the outdoors, add a garden, or even bring your toys. And with NO HOA or CDD fees, you'll have the freedom to truly make this property your own. Inside, you'll find a modern kitchen and stylish finishes throughout, perfect for easy living, an investment opportunity or AirBNB. Located minutes from historic downtown St. Augustine, with its lively shops, restaurants, and coastal lifestyle right at your doorstep. If you're looking for a turn key home at an affordable price, close to all the best St. Augustine living has to offer, this is the one. Call or text for a tour

755 S S Rodriquez St Street, St. Augustine

Listing courtesy of CROSSVIEW REALTY.

Selling Office: .

© 2026 Northeast Florida Multiple Listing Service, Inc. All rights reserved. This data is up-to-date as of . For the most current information, contact Florida Coastal Team - LPT Realty.