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$997,000
4 Beds ⋅ 3 Baths ⋅ 2157070 MLS
Discover the perfect blend of privacy, space, and historic charm at 158 Washington St., ideally located on a quiet private street in the heart of historic downtown St. Augustine. Built in 2004 and elevated with durable concrete block construction, this spacious 4-bedroom, 2.5-bath home offers 2,409 square feet of comfortable living space and an oversized two-car garage. Inside features an electric fireplace, beautiful wood floors that add warmth and character throughout the home. Enjoy breathtaking direct marsh views from both the inviting front porch and the upper deck--perfect spots to relax, take in the scenery, and enjoy St. Augustine's natural beauty. The very private backyard (artificial grass low maintenance) provides a peaceful retreat and plenty of space to enjoy outdoor living and with its generous floor plan and excellent separation of living spaces. This home offers an ideal setup for accommodating extended family or creating flexible spaces for guests, a home office, or additional living needs. just minutes from the unique shops, restaurants, cultural attractions, and historic landmarks of downtown St. Augustine, 158 Washington St. offers a rare opportunity to enjoy a private residential setting while being close to everything this iconic city has to offer. With its generous floor plan and excellent separation of living spaces, this home offers an ideal setup for multigenerational living.

158 Washington Street, St. Augustine
$667,000
3 Beds ⋅ 2 Baths ⋅ 2155896 MLS
28 Joiner Street presents a rare opportunity to own an authentic Craftsman home in the heart of Uptown St. Augustine, where original 1900 character meets modern comfort and true in-town walkability. Offering three bedrooms, two bathrooms, fully furnished and 1,378 square feet of well-arranged living space, this home showcases the craftsmanship that defines the neighborhood's most beloved residences: nine-foot ceilings, yellow pine floors, picture rail trim, eight-inch baseboards, and beautifully preserved period millwork throughout the main living areas. The welcoming covered front porch sets the tone from the moment you arrive, offering the classic St. Augustine ritual of morning coffee and evening conversation with neighbors. Inside, the updated kitchen and both renovated bathrooms deliver the convenience today's buyers expect while remaining true to the home's historic character. . A dedicated laundry area and rear-entry mudroom add the kind of everyday functionality that's hard to find in homes of this era. Behind the scenes, the major systems have been thoughtfully updated, providing the confidence buyers seek in a historic property. The electrical was updated in 2017 and the plumbing in 2018, a new water heater was installed indoors in 2025, and a durable metal roof was added in 2016, complementing the home's wood siding and classic Craftsman exterior. Set on a high and dry lot, the property offers welcome peace of mind -- a genuine advantage in this part of historic St. Augustine. The location truly sets this property apart. From your front door, you're a short stroll to the downtown waterfront, the Castillo de San Marcos, and Uptown's locally owned restaurants, coffee shops, boutiques, and galleries. Whether you're searching for a primary residence, a second home, or a flexible property with short-term rental potential, 28 Joiner Street delivers genuine historic character, thoughtful updates, and one of the most walkable lifestyles in America's oldest city.

28 Joiner Street, St. Augustine
$1,450,000
6 Beds ⋅ 2154005 MLS
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
$549,000
2 Beds ⋅ 2 Baths ⋅ 2152587 MLS
SELLER MOTIVATED! Rare opportunity to own a fully renovated, move-in-ready home in Historic Lincolnville, just minutes from downtown St. Augustine. This charming cottage features 2 private primary suites, updated designer bathrooms, original hardwood floors, and a beautifully remodeled kitchen. The standout feature is the detached garage--a rare find in Historic Lincolnville--providing secure parking, storage, a workshop, or hobby space. Durable metal roof and concrete siding offer low-maintenance living. Relax on the spacious front and rear porches overlooking the large backyard. Perfect as a primary residence, vacation home, second home, student housing, or investment property with short-term rental potential. Walk to restaurants, shopping, museums, and historic attractions, with St. Augustine Beach less than 6 miles away. Furnishings negotiable.

181 Martin Luther King Avenue, St. Augustine
$599,900
3 Beds ⋅ 3 Baths ⋅ 2145397 MLS
Turnkey living in Historic St. Augustine! Built by respected local builder Entire Inc., this beautifully furnished 3-bedroom, 2.5-bath home offers the perfect blend of modern comfort and St. Augustine charm. Thoughtfully designed with energy-efficient construction, engineered hardwood floors, granite countertops, stainless steel appliances, and high-end finishes throughout, it's ready to enjoy from day one. Relax on one of three inviting porches and enjoy breezes from the nearby San Sebastian River, or take a short stroll to some of St. Augustine's most beloved destinations, including the Ice Plant, St. Augustine Distillery, St. George Street, waterfront attractions, restaurants, shops, and historic landmarks. Whether you're seeking a primary residence, vacation retreat, or investment property, this move-in-ready home offers an exceptional opportunity to enjoy the walkable lifestyle and rich history of America's oldest city.

118 Kings Ferry Way, St. Augustine
$1,998,000
3 Beds ⋅ 3 Baths ⋅ 2143052 MLS
This home exudes charm and character . It was designed by the famed architect , F.A. Hollingsworth and resides on one of the highest elevations on one of the most desired streets in , St Augustine. The timeless architecture has been carefully restored and enhanced with the finest materials and craftsmanship from exterior to interior. Step into the foyer where the original stairs , banisters , and hardwood floors have been refinished. Original floors & trim remain throughout. The floorplan flows with formal dining , large chef's kitchen with gas and oversized quartz island , walk-in pantry and an abundance of cabinets . The formal living room is light filled and cozy with hand painted tiles covering the original wood burning fireplace . A den with built in bookshelves off the living room is the perfect place for a home office. An enclosed sunroom with new vinyl windows ,custom Bamboo blinds , stone work fireplace and split system AC overlook the large backyard and pool area . The original staircase leads to three generous-sized bedrooms and two full baths. A sitting area is adjacent to the Primary with a door leading to the outside second story porch refreshed with no maintenance Trex(TM) decking. This porch is a great vantage point to view, the Matanzas River. Large windows in the primary take in the light and water views. Storage is ample with a walk-in closet and a custom European wardrobe. The original carriage house still stands preserved and freshly painted with a new roof. The use is up to the new owner with ,220 AMP and plumbing available, it could easily be a guest house or an art studio. A storage shed was constructed behind the carriage house, keeping with the architectural integrity of the main and carriage house. Hardi(TM) Board siding, two electrical outlets and an auto fan for heat control make this a versatile space. Privacy hedges hide the fence in Backyard and add to the beautiful outdoor entertaining area surrounding the pool and spa creating a peaceful haven. You can Walk to, Castillo de San Marcos, view the landmark Cross at Our Lady Le Leche at sunset and be at the finest restaurants with a short walk. To be this close to all that Historic Downtown St Augustine offers, you will not believe the privacy and serenity that this location provides. Don't miss this perfectly reimagined and restored piece of history. View Feature list under document section for full details.

70 Water Street, St. Augustine
$749,000
4 Beds ⋅ 3 Baths ⋅ 2131492 MLS
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. This property is ideal for multigenerational living, guest quarters, a home office, or generating potential income as a short-term or long-term rental. Parking is a standout: paver courtyard + garage provide room for multiple vehicles and small boat/TOYs--rare this close to town. Updated PVC plumbing; electrical updates; refreshed lighting and interior/exterior doors;remodeled bath with custom tile shower; new pavers; and a transferable termite protection plan for added peace of mind.Location: North City/Uptown convenience--walk or bike to the Fountain of Youth and local eateries; minutes to the public boatramp, marinas, Vilano Beach, and the Bridge of Lions into downtown. Whether you're seeking a full-time residence, vacationretreat, or investment property, this versatile, island-adjacent compound offers the best of the St. Augustine lifestyle--history,coastal charm, and income potential all in one.

6 E San Carlos Avenue, St. Augustine
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 2125588 MLS
143 Washington Street is more than a home -- it is a rare opportunity to experience luxury coastal living in the heart of historic downtown St. Augustine. Perfectly positioned overlooking the tranquil waters of Lake Maria Sanchez, this exceptional newer-construction residence offers the charm and walkability of the nation's oldest city without the compromises often found in historic homes. Built in 2021 and being offered fully furnished, this turnkey retreat blends sophisticated modern design with effortless waterfront living. Expansive windows flood the home with natural light while framing breathtaking water views from multiple levels. Designed for both relaxation and entertaining, the open-concept layout flows seamlessly to private outdoor living spaces where sunrise coffees and sunset evenings become part of everyday life. Step outside to your resort-style pool overlooking the lake, creating a setting that feels more like a private luxury getaway than a downtown residence. Whether enjoying wine by the water, entertaining guests, or taking a short stroll to St. George Street, acclaimed restaurants, boutiques, galleries, and marinas, every detail of this property is centered around lifestyle. Unlike many homes in the historic district, this elevated modern residence offers the peace of mind of newer construction, contemporary systems, spacious parking, and low-maintenance living -- all while preserving the timeless character and atmosphere that make St. Augustine so special. Ideal as a primary residence, luxury second home, or high-end vacation retreat, this fully furnished property delivers a rare combination of modern luxury, walkability, water views, and turnkey convenience in one of Florida's most iconic coastal destinations. Experience historic downtown living reimagined at 143 Washington Street.

143 Washington Street, St. Augustine
$625,000
4 Beds ⋅ 2 Baths ⋅ 2124845 MLS
Welcome to your slice of history nestled in the heart of St. Augustine's vibrant downtown. Presenting a captivating 4-bedroom, 2-bathroom single-family home, exuding timeless elegance and modern convenience. Built in 1910, this exquisite residence sits majestically on a coveted corner lot, offering a lifestyle of both historic charm and urban convenience. As you step onto the property, you're immediately greeted by the allure of yesteryears, enhanced by the home's classic architectural details and lush landscaping. The exterior boasts the quintessential charm of a bygone era, while the interior seamlessly blends historic character with contemporary updates. Upon entry, the foyer welcomes you with warmth and sophistication, leading you into the inviting living spaces adorned with original hardwood floors and abundant natural light. The beautiful classic wood finishes throughout exude warmth and character with every step. The spacious living room is perfect for gatherings or quiet evenings by the fireplace, while the adjacent dining area sets the stage for memorable meals with loved ones. Outside, the charm continues with a picturesque backyard oasis, complete with lush landscaping and a detached 2-car garage. Perfect for al fresco dining, entertaining guests, or simply unwinding after a busy day, this outdoor sanctuary is a rare find in downtown living. One of the most coveted features of this property is its unbeatable location. Situated within walking distance to downtown St. Augustine's historic attractions, eclectic shops, renowned restaurants, and pristine beaches, residents can immerse themselves in the vibrant energy of the nation's oldest city while enjoying the tranquility of their own private retreat. Don't miss the opportunity to own a piece of St. Augustine's rich history and experience the ultimate blend of old-world charm and modern convenience. Schedule your private tour today and discover the magic of this captivating historic gem!

33 Cincinnati Avenue, St. Augustine
$525,000
2 Beds ⋅ 3 Baths ⋅ 2124237 MLS
CONDO WITH PRIVATE BOAT SLIP! Experience the ultimate coastal lifestyle in this beautifully updated waterfront condominium, complete with a deep-water private boat slip that can accommodate a vessel up to 38 feet. Inside, you'll find a light-filled, open-concept layout designed for both comfort and style. Upscale furnishings, recent updates and modern finishes make this condo truly move-in ready, whether you're looking for a full-time residence, vacation getaway, or income-producing short-term rental. Step outside and enjoy serene water views, effortless boating access, and the relaxed lifestyle that only true waterfront living can provide. Recent exterior improvements include updated siding, balcony, front door with sidelight, and fresh exterior paint, enhancing both curb appeal and long-term value. Additional conveniences include a private single-car garage, providing secure parking and extra storage. Residents of Sebastian Harbor can walk or bike to historic downtown St. Augustine to enjoy the nightly live music, world-class dining, art galleries, and unique boutiques, or take a short drive to the beach to experience everything the island lifestyle has to offer. Whether you're seeking a full-time residence, a vacation retreat, or an investment opportunity, this condo offers a rare combination of waterfront living, modern comfort, and timeless Old Florida charm.

931 S Ponce De Leon Boulevard, St. Augustine
$425,000
2 Beds ⋅ 1 Baths ⋅ 2123240 MLS
Tiny But Mighty Lincolnville Gem! Fully Updated 1930s Cottage. Welcome to this charming 1930s cottage in the heart of the historic Lincolnville District—668 sqft of smart, stylish living that perfectly captures the spirit of old St Augustine. Thoughtfully renovated in the early 2020s, this 2-bedroom, 1-bathroom home blends vintage character with modern convenience. Inside, you'll find wood floors throughout, vaulted ceilings & custom built-in beds maximizing space without sacrificing style. The bathroom features a timeless clawfoot tub & and the tankless water heater ensures endless hot showers. A full-size washer and dryer are also included, offering everyday practicality in a compact footprint.

141 Blanco Street, St. Augustine
$990,000
3 Beds ⋅ 3 Baths ⋅ 2120758 MLS
A Boater's Paradise Awaits! Discover this exclusive enclave of just eight condominiums, each with its own deeded boat slip—this one featuring a 15,000-lb lift and direct access to the Atlantic via the nearby St. Augustine Inlet. This solid block-constructed residence offers elegant living with sweeping, unobstructed views of the Intracoastal Waterway and the ocean inlet. Inside, you'll find a refined, beautifully maintained three-bedroom, three-bath retreat. High-end details shine throughout, including custom cabinetry, crown and trim moldings, wood and 19'' tile flooring. The spacious kitchen offers ample room to cook and entertain, complete with stainless steel appliances, wood cabinetry, and generous granite counter space. Relax on your private balcony while taking in the wildlife and watching boats glide by—it's sure to become your favorite spot. A one-car garage, additional parking, and a sparkling pool are all included. Close by are Vilano Beach and historic St. Augustine. Minimum Rental Time is one year. Quality of Life. . . That's What it is All About!

1 Radio Road Unit 203, St. Augustine
$1,900,000
4 Beds ⋅ 5 Baths ⋅ 2118899 MLS
Nestled in the serene waterside enclave of Bonita Bay, 9 Bonita Bay Drive is a stunning Spanish-style retreat just steps from the heartbeat of historic St. Augustine. This elegant 4-bedroom, 4.5-bath home offers enormous refined living space across three levels, expertly crafted in 2020 with Old-World charm and modern luxury. Living areas are flooded with natural light, and include high-end finishes, built-ins, a gas kitchen range, and a charming eat-in kitchen with an island. An elevator provides seamless access across three stories. The home's four bedrooms each include their own en-suite bath, offering privacy and comfort for guests or family. The primary suite enjoys its own wing. The two balconies deliver extraordinary panoramic views. Sit with your morning coffee on the east-facing balcony as the sun rises, and in the evening, unwind with views of the Bridge of Lions and downtown on the north-facing balcony. Outside, a private, fenced backyard provides peace and seclusion, anchored by a sparkling in-ground pool  perfect for sun-drenched Outside, a private, fenced backyard provides peace and seclusion, anchored by a sparkling in-ground pool flanked by lush palms  perfect for sun-drenched lounging or evening soirees. A private boat dock gives you direct access to the Matanzas River / intracoastal waterway, allowing for boating, fishing, or leisurely paddling, and ultimately navigation out to the ocean  perfect for the water-lover's lifestyle. Despite its tranquil setting, this home is walking distance to downtown St. Augustine. You can easily stroll into the historic district, taking in its quaint streets, shops, restaurants, and cultural landmarks. From your balcony, you can even catch glimpses of the downtown skyline and the iconic Bridge of Lions, lending a postcard-like view and a front-row seat for fireworks on special occasions.

9 Bonita Bay Drive, St. Augustine
$2,350,000
6 Beds ⋅ 5 Baths ⋅ 2118296 MLS
178 Avenida Menendez - An Iconic Flagler-Era Residence with Panoramic Bayfront Views Exquisitely restored and meticulously maintained. The Bodley/Bennett residence is a rare Flagler-era treasure, originally built in 1910 and thoughtfully renovated between 2010 and 2012. Perched along the Matanzas River, this historic legal home commands sweeping, panoramic vistas of the St. Augustine Bayfront and the legendary Bridge of Lions, offering a lifestyle defined by elegance, heritage, and unmatched waterfront charm. Boasting 6 bedrooms and 5 full baths, this residence seamlessly blends historic character with modern comforts. Yellow pine flooring, 8'' hardwood baseboards, original five-panel doors, and grand staircases evoke timeless craftsmanship while updated systems and finishes ensure contemporary luxury. Optional 1 year home warranty provided by Fidelity National Home Warranty. The First-Floor Residence is an ideal suite for generational living or distinguished guests, featuring 2 bedrooms, 1 full bath, a spacious living room with a period gas fireplace, and a formal dining room. The chef-inspired kitchen includes a Jenn-Air gas range, stainless steel appliances, granite countertops, and espresso-finished cabinetry accented with period hardwaremarrying modern convenience with classic detail. The Second-Floor Main Residence is Designed for refined living and entertaining. This level offers 2 bedrooms, 3 full baths, an inviting living room, formal dining, and a beautifully remodeled kitchen with gas range, updated cabinetry, and rich butcher block counters. Thoughtful layouts and elevated finishes create a sense of sophistication and comfort throughout. The Third-Floor Retreat is also the pinnacle of luxury living. This floor provides 2 bedrooms, 1 full bath, and a generous walk-out terrace framing some of the most breathtaking views of the Bayfront and Bridge of Lionsa private sanctuary perfect for morning coffee, sunset entertaining, or simply soaking in St. Augustine's timeless beauty. A rare convergence of history, architecture, and premier waterfront location, this residence is not just a homeit is a statement. Perfect for collectors of historic properties, lovers of fine craftsmanship, and those who seek an elevated lifestyle in one of Florida's most cherished cities. Experience St. Augustine living at its finestwhere every detail tells a story, every view inspires, and every moment is extraordinary.

178 Avenida Menendez, St. Augustine
$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
$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
$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
$725,000
2096375 MLS
Historic St Augustine - Discover the perfect blend of tranquility and convenience with this stunning 0.24acre marsh-front lot, located in the heart of historic downtown St. Augustine. Just a short walk to charming shops, delightful restaurants, and all the attractions this beautiful city has to offer, yet tucked away enough to offer a peaceful, serene retreat. The lot boasts breathtaking marsh and sunrise views, providing a picturesque backdrop for your dream home. Beautiful, mature trees grace the property, adding to its natural beauty and offering privacy and shade. With its prime location and unmatched views, this is the ideal canvas to build the home you've always envisioned. Don't miss the opportunity to own a piece of paradise in one of the most desirable areas in St. Augustine.

160 Washington Street, St. Augustine
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