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$4,750,000
3 Beds ⋅ 5 Baths ⋅ 2126480 MLS ⋅ 32084 Zip Code
Located in this highly desirable waterfront enclave, 65 Water Street —designed by the renowned Cronk Duch Architects—offers refined coastal living with uncompromising quality, privacy, and craftsmanship throughout, all within walking distance to historic downtown St. Augustine. This 3-bed, 4.5-bath residence is thoughtfully designed for both everyday comfort and elegant entertaining, enhanced by multiple covered balconies that capture serene water views and coastal breezes. The heart of the home is the chef's kitchen, featuring high-end appliances and an open-concept layout flowing effortlessly into the family and dining areas. A sophisticated wet bar showcases elegant built-in cabinetry and a 140-bottle Sub-Zero wine cooler. Rich architectural details define the interior, including Carlisle wide-plank heart of pine flooring throughout, custom built-ins throughout, elegant light fixtures, and a dedicated home theater with newer equipment. See more A whole-home Sonos sound system enhances both indoor and outdoor living. Luxury amenities continue with a sauna, central vacuum, residential elevator, and built-in safe. Adding exceptional flexibility and privacy, the property includes two separate casitas with private accessperfect for guests, extended family, or versatile living options such as a home office or studio. Outdoor living is equally impressive. Enjoy a luxurious heated saltwater lap pool with updated equipment, a convenient cabana bath, and a gas firepit, all set against the tranquil waterfront backdrop. Boating enthusiasts will appreciate the newer dock with concrete pilings, boat and jet ski lifts, and vinyl bulkhead, all situated on a generous 75 x 160 waterfront lot. Constructed for durability and peace of mind, the home features concrete block construction, cementitious siding, a metal roof, hurricane windows, foam insulation, two new AC units, and a 26 kW generator supported by a 500-gallon buried gas tank. The main garage offers a vehicle lift and extensive custom cabinet storage. This rare waterfront offering blends timeless architectural design, modern luxury, and exceptional construction in one of St. Augustine's most coveted, walkable locations.

65 Water Street, St. Augustine
$2,400,000
7 Beds ⋅ 5 Baths ⋅ 2112505 MLS ⋅ 32084 Zip Code
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
$2,300,000
3 Beds ⋅ 2 Baths ⋅ 2129613 MLS ⋅ 32084 Zip Code
Direct Intracoastal Front Property with Deep Water Lift on Multiple Lots in Vilano Beach! Ponte Vedra just North and St. Augustine just south! This is such an amazing property! Your own beach! 3 Platted Lots! 100 Ft on the Water! Keep the 2 Lots on the Water and sell the back lot or develop it! Another idea would be to have 2 Intracoastal Front lots! Located a block away from Caps! Beach access at the end of the street East! Survey on file!

507 Third Street, St. Augustine
$2,175,000
5 Beds ⋅ 4 Baths ⋅ 2108587 MLS ⋅ 32084 Zip Code
Stunning panoramic views and refreshing ocean breezes are just a couple of the many highlights of this remarkable new construction home from Terra Build in the Porpoise Point community of St. Augustine, where the Intracoastal Waterway meets the Atlantic Ocean. Located only minutes from historic Old St. Augustine, this exquisite coastal modern residence spans 3,511 square feet and showcases breathtaking views from nearly every window. Built to last with auger cast pilings and concrete block construction on the first level, the home features five spacious bedrooms and four bathrooms, blending comfort with contemporary style. An elevator provides added convenience. Perfectly positioned on a corner lot just steps from beach access, this home offers both privacy and accessibility. Vilano Beach is celebrated as one of Northeast Florida's most iconic communities, with a vibrant local culture, boutique shopping, and dining all within walking distance. Don't miss your chance to own this exceptional new construction in a community that embodies the essence of Florida living. Embrace the coastal lifestyle and make your dreams a reality in Porpoise Point!

318 Genoa Road, St. Augustine
$1,936,000
4 Beds ⋅ 4 Baths ⋅ 2148915 MLS ⋅ 32084 Zip Code
Highly elevated, this Direct Ocean Front home offers expansive views overlooking the ocean, inlet AND downtown St Augustine. Stunning cathedral ceilings and floor to ceiling windows offer breathtaking views of the Atlantic. A fully renovated white kitchen opens to the living and dining room and offers views to the north and east. The spacious master opens to a 2nd story roof top deck with unmatched views of the inlet and downtown St Augustine. Passing boats are an alluring vision... And there is no better spot to enjoy the 4th of July fireworks. Upstairs, a 2nd master suite and an office loft will make working from home a pleasure. On the bottom floor there is separate in law suite with 2 bedrooms, a kitchenette and bonus room. A multitude of decks offering 360degree views make this home truly special. 3 Car Garage! Short term rentals allowed.

4 Viejo Street, St. Augustine
$1,865,000
4 Beds ⋅ 5 Baths ⋅ 2133716 MLS ⋅ 32084 Zip Code
Brand new 3-story pool home with Atlantic Ocean views! Experience sunrise and sea breeze from dual balconies in this 3,131 sq ft masterpiece featuring 4 bedrooms, 4.5 baths, elevator, and private saltwater pool on an oversized lot. This property is a rare find, perfect for high-end entertaining or a lucrative short-term rental with NO HOA and nightly rentals permitted. The ground floor offers a 2-car garage, bedroom, and full bath. The second level boasts an expansive open living and kitchen area, a guest suite, and a covered ocean-view balcony. The top floor features an additional guest room plus a luxurious primary suite with its own private balcony. Outside, relax in the saltwater pool, spacious yard, and covered lanai. Built for ultimate peace of mind with Hardie board siding, impact-resistant windows, and a 2-10 builder's warranty, this residence blends coastal luxury with modern durability just steps from the sand. Secure your piece of the Florida coast today!

213 Twenty-First Street, St. Augustine
$1,835,000
3 Beds ⋅ 3 Baths ⋅ 2143052 MLS ⋅ 32084 Zip Code
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
$1,815,000
3 Beds ⋅ 4 Baths ⋅ 2118038 MLS ⋅ 32084 Zip Code
Along the serene edge of Maria Sanchez Lake lies one of downtown St. Augustine's most alluring hidden treasures. Beyond a graceful brick archway, this private sanctuary reveals itself — a home so captivating that every guest departs inspired and eager to return. A study in balance and beauty, the residence blends European refinement with a soulful, worldly aesthetic. Its design nods to the understated elegance of Belgian estates, the timeless sensibility of Darryl Carter, and the calm minimalism found in Asian influence. Every surface and texture — from ancient Burmese teak and reclaimed oak to artisan brickwork — was chosen with intention, creating an enduring home rooted in craftsmanship and character. The main level was envisioned for effortless entertaining and connection. Folding glass walls blur the line between indoors and out, opening completely to the front courtyard and rear lake terrace. A masterfully built summer kitchen by a local craftsman anchors the courtyard beside a peaceful plunge pool and spa-style bath. Inside, the chef's kitchen delights with a statement Viking range, open shelving, and dramatic marble slabs that extend seamlessly up the walls. Generous dining and living areas flow naturally toward the lakefront, where gentle breezes and daily scenes of herons and egrets create a living masterpiece. Originally a 1920s cottage, the home's historic essence now mingles with bold modern lines. Just off the main living area, a refined study framed by an antique arched window captures glimmering lake reflections and sunlight by day, and candlelit warmth by night. Upstairs, the lake becomes your morning view. The primary suite and an adjoining guest suite  currently used as a sitting retreat  each open to private balconies beneath a graceful old tree. Both baths are finished in marble with curated lighting and high-end fixtures. Along the south side, a screened porch invites lingering conversation or afternoon reading and transitions beautifully to a sunlit terrace ideal for herbs or climbing roses. "The Little Nest," a third-floor hideaway, crowns the home with panoramic vistas that stretch across the historic skyline to the Intracoastal. Vaulted ceilings, reclaimed beams, and marble accents create an inspiring space for writing, resting, or simply dreaming. Across the brick courtyard, the detached garden studio offers a charming bonus retreat  with its own entrance, vaulted ceilings, reclaimed-beam details, and a small kitchenette and bath. Originally permitted as a shed and not counted in the home's total living area, this stylish escape offers flexibility for guests, creative work, or quiet reflection. Timeless, tactile, and transporting  153 Washington Street is more than a residence. It's a rare experience of historic St. Augustine living, where cobblestone streets and shimmering waterways frame a lifestyle that feels both centuries old and utterly new.

153 Washington Street, St. Augustine
$1,737,500
5 Beds ⋅ 4 Baths ⋅ 2133406 MLS ⋅ 32084 Zip Code
Located in the heart of Vilano Beach, 152 Sherwood Ave offers the perfect blend of luxury, space, and coastal lifestyle. Just a short walk to both the Atlantic Ocean and the Intracoastal Waterway, and minutes from historic downtown St. Augustine, this beautifully designed home is ideally positioned to enjoy everything the area has to offer. Situated on a 75' x 125' lot, the home features 4,402 sqft under air (5,367 total) with 5 bedrooms, 3.5 bathrooms, a private office, flex room, and a dedicated theater room with projector and screen. The kitchen is equipped with a gas stove, and the home is enhanced by a Control4 whole-home sound system. The outdoor living space is designed for relaxation and entertaining with a heated pool, gas poolside fireplace, paver lanai, and low-maintenance turf yard. Additional features include a 24' x 25' garage, security system, and perimeter security cameras. A rare opportunity to own a spacious home just steps from both the ocean and Intracoastal.

152 Sherwood Avenue, St. Augustine
$1,645,000
4 Beds ⋅ 4 Baths ⋅ 2129072 MLS ⋅ 32084 Zip Code
Experience historic luxury at 290 St. George St, the former personal residence of famed architect Fred Henderich. Masterfully reimagined by John Benoit of BEHST Builders, this estate seamlessly fuses 1900s ''Old World'' soul with 21st-century sophistication. Positioned on a rare 62.5x200 lot stretching from St. George to Cordova St, the property offers stunning Lake Maria Sanchez views and parking for 10+ cars. The main home radiates light, showcasing original woodwork, coffered ceilings, and a gourmet kitchen with custom cabinetry and a butler's door. The primary downstairs suite features floor to ceiling tile work, a tub and a walk-in shower, flowing into a sunlit morning room. Upstairs, find a nautical suite complete with a steam shower. Beyond a private sanctuary, this estate is a lucrative asset. The detached cottage is a designer showstopper with a vaulted living area and private lakefront verandas. Perfectly positioned as a high-end luxury rental in the heart of St. Augustine.

290 St. George Street, St. Augustine
$1,630,000
2096359 MLS ⋅ 32084 Zip Code
A special Commercial property is now available just north of the Historic District, and south of the Municipal Airport . With a colorful history as the iconic Harley Davidson Dealership, there is 7198 Sq Ft of total space under roof that has 3730 SF of finished retail space (under HVAC) and 3468 of warehouse space all The current zoning is City of St Augustine CM-2 (Commercial Medium Intensity) , which provides for multiple uses and shows a traffic count of approximately 36,500 daily. additional parking space can be provided by contiguous property to the rear. Aerial Map location in ''Documents''

3956 N Ponce De Leon Boulevard, St. Augustine
$1,500,000
3 Beds ⋅ 4 Baths ⋅ 2121257 MLS ⋅ 32084 Zip Code
Wake up to panoramic Atlantic Ocean views from this direct oceanfront home at 3264 Coastal Highway in St. Augustine, where coastal elegance meets effortless beach living just minutes from historic downtown. Designed for relaxation and entertaining, this spacious three bedroom, three and a half bath residence features vaulted ceilings, expansive windows, and a versatile bonus game room with additional sleeping space ideal for hosting guests or maximizing rental potential. Wrap around Trex decking and a generous sand level patio create seamless indoor outdoor living, perfect for sunrise mornings, ocean breezes, and unforgettable coastal gatherings. A protective seawall, updated living spaces, and a layout tailored for both personal enjoyment and investment opportunity make this property a rare find along Northeast Florida's sought after shoreline. Whether used as a second home, vacation retreat, or income producing property, this residence delivers the lifestyle and location buyers are actively searching for. Buyer to verify square footage, rental regulations, and all property details. Direct oceanfront home in St Augustine FL 32084 with Atlantic views, immediate beach access, and close proximity to historic downtown St Augustine and Northeast Florida coastal attractions.

3264 Coastal Highway, St. Augustine
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 2125588 MLS ⋅ 32084 Zip Code
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
$1,402,500
4 Beds ⋅ 4 Baths ⋅ 2137773 MLS ⋅ 32084 Zip Code
Welcome to ''SERENITY NOW'' IN BEAUTIFUL VILANO BEACH. This is the beach home you have been waiting for your whole life. Built in 2006 on concrete pilings with hurricane proof windows looking out at the ocean, St Augustine Inlet leading to the ICW. The kind of beach home that guests book without hesitation. The 4 bedrooms, 4 bath layout keeps bedrooms tucked away while the main living space stays open and flooded with natural light. The open layout of the elevated main floor keeps the family room and kitchen connected, so everyone stays part of the conversation while enjoying views of the ocean. Gas powered tankless heating; electric HVAC with two remote controlled zones; the new electric fireplace in 2025 is a beauty; house covered over by a hurricane proof new roof in 2025. Step out onto the wrap around decks facing the ocean to the north/around to the southeast exposure with your morning coffee or the afternoon cocktail. You will never want to leave; neither will guests/friends Steps to the beach and the ocean with a full body enclosed outdoor shower to get the sand off and be ready for the evening activities. Located in Flood Zone X, (no need for flood insurance) LOMA FEMA Letter of Map Amendment documents supporting Flood Zone X designation offers added peace of mind. Recent DBPR Certificate of Balcony and Stairs Home Inspection as well. Maple wood floors throughout the interior of the property. Full water purificaion system throughout the home. Weather/rust proof outdoor deck furniture and iodized aluminum patio table with 8 chairs on the deck make for terrific late evening summer dinners to the sound of the crashing waves. Combined with solid construction; hardiboard exterior siding freshly painted 2025 and a practical layout, the home feels easy to own and live in. See list of upgrades and improvements in documents section of the listing.

510 Porpoise Point Drive, St. Augustine
$1,400,000
7 Beds ⋅ 5 Baths ⋅ 2159371 MLS ⋅ 32084 Zip Code
Luxury Coastal Retreat with Heated Pool & Spa | Walk to Vilano Beach | Proven Vacation Rental Opportunity Just a short 6-minute walk from the sand, this beautifully renovated 7-bedroom, 4.5-bath coastal retreat offers over 4,000 square feet of living space in one of St. Augustine's most sought-after beachside communities. Whether you're searching for a primary residence, second home, or high-performing vacation rental investment, this exceptional property delivers the ideal blend of luxury, location, and lifestyle. Designed to accommodate large gatherings, the home comfortably sleeps up to 18 guests and features expansive living spaces, soaring ceilings, and a dramatic two-story great room highlighted by wood coffered ceilings and a stunning statement chandelier. The open-concept layout flows seamlessly from the spacious living areas to the private outdoor oasis. Step outside to enjoy your own heated saltwater pool, spa, and covered summer kitchen with built-in grill--perfect for entertaining after a day at the beach. The backyard provides the resort-style experience today's buyers and vacation guests seek. A dedicated game and bunk room creates the ultimate hangout space for guests, complete with arcade games, shuffleboard, and flexible sleeping arrangements, making this property especially attractive for multi-generational vacations and group rentals. Located in the heart of Vilano Beach, you'll enjoy easy access to Surfside Park Beach, the Tolomato River, neighborhood parks, and scenic coastal trails. The property is also just minutes from Historic Downtown St. Augustine, where residents and visitors can explore St. George Street, Castillo de San Marcos, award-winning restaurants, boutique shopping, museums, and year-round attractions. Property Highlights: 7 Bedrooms | 4.5 Bathrooms Over 4,100 SF of renovated living space Heated saltwater pool and spa Covered outdoor entertaining area with built-in grill Spacious game room/bunk room Sleeps up to 18 guests Walkable to Vilano Beach and Surfside Park Minutes to Historic Downtown St. Augustine Excellent opportunity for vacation rental income Ideal primary residence, second home, or investment property 2 minute walk to tennis court and dog park. Rarely does a property combine beach access, luxury amenities, large-group accommodations, and proximity to Historic St. Augustine in one exceptional offering. Experience the best of Florida coastal living while enjoying the flexibility and income potential of a premier beach destination property. Call today for a private showing.

157 Lawn Avenue, St. Augustine
$1,400,000
4 Beds ⋅ 3 Baths ⋅ 2149884 MLS ⋅ 32084 Zip Code
Welcome to 3180 Coastal Highway, Villa Rosa--an exceptional oceanfront retreat in the heart of Vilano Beach. This beautifully furnished 4-bedroom, 3-bath home offers stunning Atlantic Ocean views from the open-concept living, dining, and kitchen areas. With 50 feet of direct ocean frontage, enjoy spectacular sunrises from the expansive composite deck (2022) and sunsets over the Intracoastal Waterway. Features include a 2017 roof, impact-rated sliding glass doors, attached garage, parking for up to four vehicles, and an outdoor shower. Villa Rosa is also a proven income-producing property, generating over $140,000 annually in vacation rental revenue. Minutes from dining, shopping, and local attractions, this turnkey home is ideal as a primary residence, vacation getaway, or investment opportunity. Showings are by appointment and subject to guest occupancy.

3180 Coastal Highway, St. Augustine
$1,400,000
1 Beds ⋅ 1 Baths ⋅ 2120239 MLS ⋅ 32084 Zip Code
Discover a rare opportunity to own 38.2 acres just minutes from historic downtown St. Augustine and the beaches. This unique property features approximately 12 acres of high and dry land plus a breathtaking 10-acre private lake — the perfect setting for your dream estate, a private retreat, or future development opportunities. A charming 1 bed / 1 bath barndominium is already in place, offering immediate use while you plan your vision. Whether you're dreaming of building a forever home on the water, creating a family compound, or exploring rezoning for other possibilities, this property delivers unmatched potential. Neighboring lot is also for sale, 13.45 Acres. Seller is willing to sell separate or together.

1895 Deer Run Road, St. Augustine
$1,355,000
4 Beds ⋅ 3 Baths ⋅ 2140087 MLS ⋅ 32084 Zip Code
Unobstructed views of the Atlantic Ocean, the inlet, Anastasia Island, and the St. Augustine Lighthouse set the tone for this rare waterfront opportunity in the heart of Vilano Beach. Located on a quiet dead end street, 2651 Palencia Street offers privacy, flexibility, and a front row seat to one of the most dynamic coastal settings in Northeast Florida. Enter the home by way of the wraparound deck on the second level, where sailboats pass through the inlet and the ocean breeze is constant. From there, the main living area flows seamlessly between the kitchen, dining, and living spaces, all oriented to capture the water views. This level also features three bedrooms, two full bathrooms, and an in unit laundry area, creating a layout that works well for both full time living and visiting guests. The ground level offers a separate living area with its own bedroom, bathroom, and living space, providing privacy from the main living area and flexibility for various uses. This space works well for guests, extended family, a private home office, or potential rental income. Take advantage of the ample garage space and additional storage for beach toys, tools, and surfboards. The oversized lot adds another layer of opportunity, providing space to expand, reconfigure, or develop in the future. With no HOA, owners have the freedom to truly make this property their own. The lifestyle here is what makes this location so special. Morning walks along the inlet with the lighthouse in the distance, quick trips to the beach just steps away, and easy access to Vilano Beach restaurants, shops, and local favorites all within walking or biking distance. Waterfront, walkability, and views are a rare combination, and this property offers all three. Whether you are looking for a primary residence, second home, investment property, or a long term redevelopment opportunity, this is one of those hard-to-find and even harder-to-replace properties. Book your private tour today!!

2651 Palencia Street, St. Augustine
$1,350,000
3 Beds ⋅ 3 Baths ⋅ 2123571 MLS ⋅ 32084 Zip Code
Just a few steps away from the beach or the Intracoastal waterway, this stunning home is truly a gem not to be overlooked. Elevated at 12 feet with impact doors and windows, and fully insulated with whole house cell foam, the home exudes quality from the moment you arrive. With cypress mitered beams accentuating the 14-foot ceilings in the great room, upgraded lighting, and quartz countertops throughout, every corner reflects high-class craftsmanship. The kitchen boasts artisan tiles on the backsplash, slate gray stainless-steel appliances, a dual-zone wine cooler, and a walk-in pantry. The master bedroom features a spacious walk-in closet with built-ins for added storage convenience. Its ensuite bath offers a luxurious soaking tub and a separate beautifully tiled seamless glass shower, complemented by a Restoration Hardware double vanity for an extra touch of elegance. Step outside the master bedroom or great room to enjoy the screened-in porch for outdoor entertainment

80 Ferrol Road, St. Augustine
$1,300,000
2134306 MLS ⋅ 32084 Zip Code
Comp

2802 N 5th Street Unit 200, St. Augustine
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 2116690 MLS ⋅ 32084 Zip Code
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
$1,148,000
4 Beds ⋅ 4 Baths ⋅ 2143409 MLS ⋅ 32084 Zip Code
Two homes. One address. Unlimited flexibility in Uptown St. Augustine. 16 Locust Street, also known as 'The Sisters Cottages' is a rare Abbott Tract offering featuring two fully restored historic cottages, each with its own private space and income potential. Positioned in one of Uptown's most sought-after pockets, this property offers a level of versatility that is exceptionally hard to replicate. Whether used as a primary residence with a private guest house, a multigenerational compound, or a fully optimized short-term rental asset, the layout allows for multiple paths to ownership without compromise. Each residence operates independently with its own entrance, courtyard, and dedicated parking, creating true separation and privacy. The location is a major part of the story. You are steps into the fabric of downtown St. Augustine, surrounded by established restaurants, coffee shops, galleries, and local retail, with seamless access to the Castillo, St. George Street, and the Bayfront. This is the walkable historic lifestyle buyers come here for, with the beach just a short drive away. The main cottage, dating back to 1844 and featured on the 1885 Birds Eye Map, has been restored with a level of detail and discipline rarely seen. Originally owned by the Triay and Capo families, the home underwent a full down-to-the-studs renovation in 2019 with all major systems replaced, including plumbing, electrical, mechanicals, roof, and windows. What sets it apart is the preservation. Original wavy glass remains intact. The entry hall wainscoting was uncovered and restored in place. The front porch ceiling features antique heart pine bead-board that took over a year to source and the trim was custom milled to exact period dimensions. The main home (Big Sister) offers three bedrooms and three bathrooms across 1,410 square feet, including two en suite bedrooms, along with a private courtyard, dedicated parking, spray foam insulation, and a wind mitigation certificate. It is offered fully furnished and turnkey. The second cottage (Little Sister), built in 1920, sits above a two-car garage and functions as a completely independent residence. With one bedroom and one bathroom across 560 square feet, it features a private entrance, its own courtyard, separate electrical service, and additional parking. Like the main home, it has been fully rebuilt from the foundation up. Interior details include a rewired 1940s stove, original 1920s light fixtures, a soaking tub, mahogany closet doors, and imported hardware sourced from Italy, creating a space that feels curated rather than renovated. Fully restored, fully furnished, and located in one of the most tightly held areas of St. Augustine, 16 Locust Street represents a rare combination of historical significance, modern infrastructure, and income-producing flexibility. Opportunities like this are not easily recreated, and they do not come to market often.

16 Locust Street, St. Augustine
$1,125,000
3 Beds ⋅ 3 Baths ⋅ 2129237 MLS ⋅ 32084 Zip Code
Where history meets the tides in the heart of St. Augustine. Built in 1924 this Georgian-style home was thoughtfully designed and positioned to capture the evening coastal breezes and the natural beauty of Macaris Creek. Since its construction, only two families have owned this home, a rare legacy of stewardship and care. Today, the property has been fully restored from the foundation and structural framing upward, blending historic character with modern peace of mind. Major updates include a new roof, HVAC, electrical, plumbing, LVP throughout, structural systems, and foundation — all completed to current building codes. This is a true restoration, not a cosmetic renovation. Set directly on Macaris Creek, a tidal waterway with access during favorable tides to the Matanzas River and St. Augustine Bayfront, the home offers a unique waterfront lifestyle. This is a RARE find. Don't miss your opportunity to own this prime real estate within 1 mile of Downtown St. Augustine!

71 Fullerwood Drive, St. Augustine
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 2133715 MLS ⋅ 32084 Zip Code
***Open House Saturday 3/14, 12-3pm***NEW CONSTRUCTION POOL HOME WITH NO HOA! Secure your coastal retreat today and take advantage of $20k builder credit toward closing costs or a rate buy-down. Priced to sell! This 1800 sqft home features 4 bedrooms and 3.5 bathrooms, LVP flooring throughout, one-car garage, designed for a private getaway or a high-yield income property. Just a short walk to the beach, the home boasts a private saltwater pool, durable Hardie siding, and impact-resistant windows for ultimate peace of mind. Located minutes from the dining and historic charm of St. Augustine, this prime location offers the best of Florida living with zero HOA restrictions. 2-10 Builders Home Warranty included with purchase. Whether you are looking for an investment opportunity or your own seaside sanctuary, this home delivers unmatched value and quality.

609 Twenty Second Street, St. Augustine
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 2133713 MLS ⋅ 32084 Zip Code
NEW CONSTRUCTION POOL HOME WITH NO HOA! Secure your coastal retreat today and take advantage of $20k builder credit toward closing costs or a rate buy-down. This 1800 sqft home features 4 bedrooms and 3.5 bathrooms, LVP flooring throughout, one-car garage, designed for a private getaway or a high-yield income property. Just a short walk to the beach, the home boasts a private saltwater pool, durable Hardie siding, and impact-resistant windows for ultimate peace of mind. Located minutes from the dining and historic charm of St. Augustine, this prime location offers the best of Florida living with zero HOA restrictions. 2-10 Builders Home Warranty included with purchase. Whether you are looking for an investment opportunity or your own seaside sanctuary, this home delivers unmatched value and quality.

605 Twenty Second Street, St. Augustine
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 2133712 MLS ⋅ 32084 Zip Code
New Construction Pool Home, No HOA, $20k builder credit towards closing costs. Now is the time to secure your coastal retreat or vacation home! Walk to the beach from your new home, featuring 1800sqft of living space, 4 beds, 3.5 baths, one-car garage, saltwater pool, LVP flooring throughout, Hardie siding exterior, and impact resistant windows. Located minutes from historic St. Augustine, dining, and entertainment. Perfect for both full-time living or short-term rental opportunities, this prime location delivers both relaxation and strong investment potential. 2-10 Builders Home Warranty included with purchase.

603 Twenty Second Street, St. Augustine
$1,100,000
2116538 MLS ⋅ 32084 Zip Code
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
$1,095,000
4 Beds ⋅ 4 Baths ⋅ 2133714 MLS ⋅ 32084 Zip Code
New Construction Pool Home, Priced Below Market Value, No HOA, $20k builder credit towards closing costs. Now is the time to secure your coastal retreat or vacation home! Walk to the beach from your new home, featuring 1800sqft of living space, 4 beds, 3.5 baths, one-car garage, saltwater pool, LVP flooring throughout, Hardie siding exterior, and impact resistant windows. Located minutes from historic St. Augustine, dining, and entertainment. Perfect for both full-time living or short-term rental opportunities, this prime location delivers both relaxation and strong investment potential. 2-10 Builders Home Warranty included with purchase.

607 Twenty Second Street, St. Augustine
$1,090,000
3 Beds ⋅ 3 Baths ⋅ 2140064 MLS ⋅ 32084 Zip Code
28 E Park Avenue is a rare offering in the heart of Fullerwood, Uptown St. Augustine's most established and character rich neighborhood. Originally built in 1926 and thoughtfully renovated, this marsh front residence blends historic architecture with modern systems and upgrades, set on three expansive lots against a permanently protected natural backdrop that ensures long term privacy and unobstructed views. The moment you step onto the expansive screened front porch, the tone is set overlooking the private park out front and welcoming neighborhood. Inside, original craftsmanship pairs with a bright, open kitchen with gourmet appliances (Wolf Stove, Elite GE Coffee, Filtered water refrigerator and Monogram 2nd oven/Microwave) and an inviting family room with a custom bar, creating a layout designed for both intimate evenings and larger gatherings. A secondary screened porch overlooks the private backyard and sweeping marsh views. Coastal breezes and wildlife create a tranquil setting that feels worlds away from the activity of town. The primary suite is privately positioned on the main level with a generous walk through closet and updated bath, while the upper level offers a spacious guest retreat and flexible loft space ideal for an office or additional sleeping quarters. The scale of the property is a true differentiator, with three lots providing exceptional space, privacy, and flexibility, including ample room for a future pool while maintaining generous green space. Newly installed professional privacy fencing provides security and peace of mind for pets and children without compromising the openness of the setting. The property's versatility further distinguishes it. A long paver drive accommodates an RV and boat and leads to an oversized two car garage with a fully remodeled, climate controlled studio featuring a kitchenette and plumbing in place for a future full bath and laundry. Whether utilized as a Bonus room, guest residence, executive office, multigenerational suite, creative studio, or income producing space, the flexibility is substantial. In addition, the separate workshop building is also climate-controlled and configured with dual suites, further expanding the possibilities for hobby use, business operations, guest overflow, or additional private workspace. Extensive recent improvements include upgraded HVAC with UVC air purification, improved ductwork and drainage systems, updated electrical, a resealed roof, new water heaters, a security system, irrigation via artesian well, refined landscaping, and enhanced exterior finishes. In early 2025, the City of St. Augustine secured permanent conservation of the adjacent marshland, protecting the natural vista and reinforcing the long term value of this setting. Positioned within Uptown, the home is walkable and bikeable to local favorites including Boat Drinks, Dos Coffee, and Crème de la Cocoa, as well as galleries and boutiques that define the area's creative energy. A neighborhood kayak launch is just down the street, offering easy access to the water, while historic downtown is minutes away for dining and culture and Vilano Beach is equally close for coastal access. The result is a refined coastal lifestyle that balances privacy and authenticity with convenience and vibrancy. Zoned RS 1 with weekly rental eligibility upon registration, this property offers architectural character, modern comfort, protected views, rare land value, and unmatched flexibility in one of St. Augustine's most desirable enclaves.

28 E Park Avenue, St. Augustine
$1,075,000
4 Beds ⋅ 4 Baths ⋅ 2135409 MLS ⋅ 32084 Zip Code
Beautifully reconstructed in 2014, this meticulously maintained 4BR/3.5BA pool home sits on a rare .37 acre double lot in St. Augustine's highly sought after Fullerwood neighborhood. Offering 3,271 sq. ft. of updated living space, this property blends historic charm with modern construction and high quality finishes. The home features refinished heart pine floors, a spacious chef's kitchen with granite countertops and custom cabinetry, Brazilian cherry flooring, two gas fireplaces, custom closets, and plantation shutters. Although the South Wing is new construction, the full rebuild included the complete replacement of all major systems throughout the home, including plumbing, electrical, HVAC, windows, roof, and insulation. Enjoy exceptional outdoor living with a screened saltwater pool, outdoor shower, paver deck, vinyl privacy fencing, and two concrete driveways. Additional upgrades include a 3 car garage, whole house generator, buried propane tank, tankless water heaters, and artesian well with equipment. Located just blocks from Uptown's cafés, boutiques, and restaurants, and less than one mile to historic Downtown St. Augustine. Vilano Beach is minutes away. A rare opportunity to own a fully updated home in one of the city's most desirable neighborhoods.

17 Sylvan Drive, St. Augustine
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