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$4,750,000
3 Beds ⋅ 5 Baths ⋅ 2126480 MLS
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
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
$1,900,000
2099662 MLS
Discover an extraordinary opportunity to own 44 Spanish Street Inn, an 8-room, bed & breakfast, with potential to expand to 10 rooms, just steps from iconic St. George Street and Flagler College in the Historic District of St. Augustine, Florida. This charming property blends timeless architecture with modern comforts, offering guests beautifully appointed, air-conditioned rooms with flat-screen TVs and complimentary Wi-Fi. Guests awaken to a complimentary full breakfast and relax in the tranquil garden courtyard or on the shaded terrace before exploring the walkable wonders of America's oldest city. Beyond its proven income as a bed & breakfast, this property's prime location and multiple commercial use potential allows for transformation into a boutique inn with a café, a restaurant, or retail offerings to capture additional revenue streams in one of Florida's most visited historic districts. Whether you're an investor seeking a high-demand short-term rental asset or an entrepreneur ready to blend hospitality with lifestyle in a vibrant community, 44 Spanish Street Inn is your gateway to owning a piece of St. Augustine's timeless appeal. Contact us today to schedule your confidential showing and explore how this property can become your next landmark investment.

44 Spanish Street, St. Augustine
$1,835,000
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
$1,815,000
3 Beds ⋅ 4 Baths ⋅ 2118038 MLS
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
$1,700,000
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
$1,645,000
4 Beds ⋅ 4 Baths ⋅ 2129072 MLS
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
$1,450,000
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
$1,400,000
6 Beds ⋅ 8 Baths ⋅ 2100987 MLS
Rare Build to Suit Development Opportunity in Historic Downtown St. Augustine. UPDATED FLOOR PLANS w/ ELEVATOR OPTION The existing building at 5 Palm Row to be remodeled and restored to a residential duplex. *This listing is for the sale / reservation of ONE unit of the duplex after basic conversion per floorpans noted / near white box remodel level* Initial townhome price of $745,000 subject to final plans. 2 Parking Spots per unit in a building to be developed across Palm Row as shown in site plan. Call for build to suit options and discussion with developer. Near visitor attractions, the St. Augustine Municipal Marina and Flagler College, the proposed upscale units could be fantastic seasonal / long-term rentals, residences for boat owners, or an upscale housing option. Easy access to beaches via AIA. Lot 1 (5 Palm Row) features 3,555 sq ft of conditioned space, currently used as office space, with plans to restore it to a residential duplex that combines charm, functionality, and luxury upgrades. The drawings are included in this listing. The townhome layout consists of three levels. - Carriage house-style garages on the ground level. One spot will be designated for the townhome and two for the eventual duplex at 5 Palm Row. - The second floor has an open concept living, kitchen, dining area, with a screened porch. 3 bedrooms, 3 full baths, and ample closet space make this ideal for shared living. - The attic level offers a large, privileged bedroom with a full luxury bath and walk-in closet. Complete with space for a private outdoor porch or enclosed sunroom. - With plenty of private space, this townhome would function extremely well as unique student housing, a short-term rental, or multi-generational living.

5 Palm Row, St. Augustine
$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
$1,148,000
4 Beds ⋅ 4 Baths ⋅ 2143409 MLS
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
$1,060,000
4 Beds ⋅ 2 Baths ⋅ 2151245 MLS
Sold Comps for Marketing Purposes Only

26 Riberia Street, St. Augustine
$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
$1,020,000
3 Beds ⋅ 3 Baths ⋅ 2089684 MLS
It's a rare pleasure to find a renovation that honors the architectural integrity of the original home while embracing the comforts and functionality of modern living. This beautifully restored residence strikes that balance - offering a seamless path between the gathering rooms, kitchen, and expansive deck, all of which enjoy tranquil views of Lake Maria Sanchez. Traditional details abound, from gleaming heart pine floors to wainscoting in the generous entry foyer and living room. A wide bay window frames the front garden, while an oversized pocket door allows you to close off the kitchen when privacy is desired. The entry foyer - spacious enough to furnish, opens into a welcoming living room, leading in turn to the sunroom, dining room, and a light-filled kitchen. No matter where you stand, the lake is a constant, sparkling presence. In the late afternoon, its surface shimmers with golden hues as the sun dips toward the horizon - an everyday reminder of nature's beauty. The gathering rooms are large and have a circular flow. A fireplace on the diagonal and the bay window alcove anchor 2 distinct spaces in the living room. Its versatility invites you to arrange the room to suit your needs and style. The kitchen was designed and outfitted by a talented woodworker who previously call 314 St George St home. Its suits the bungalow style of the house, easily blending form and function with a simple beauty. The sun room runs along the south side, featuring a casual sitting area on the east end and the dining room on the west. Under-window shelves offer a place to hold your cookbooks and display your favorite dishes. French doors between kitchen and dining open to the deck and let the sunshine in during afternoon hours. The primary bedroom is en-suite with private bath and is located on the 1st floor. With 4 windows and a vaulted ceiling, 2 of those windows overlook the water while French doors lead you to the deck. Upstairs, the front bedroom features a large alcove nestled beneath the tree canopy. The rear bedroom faces the lake and both rooms share the hall bath. Laundry and welcome storage occupy 2 rooms and offer potential for adding a private bath and walk-in closet for the front bedroom. The back deck is a favorite place for dining, birdwatching, morning coffee, evening cocktails and makes for a great outdoor office too! The backyard is landscaped with native plantings and fenced to keep your 4-legged family members close by. A covered carport on the lakeside provides convenient, sheltered parking and a place for the kayak. Every detail, whether newly added or lovingly preserved, reflects a deep pride of ownership. Words and photos can only go so far - this is a home you must experience in person. With dual frontage on both St George and Cordova Streets, this home enjoys 2 of the most desirable addresses in the city's cherished residential historic district. It's a pleasant stroll along the lake, down St George St or along the bayfront as you head to the central plaza downtown to begin your exploration of the myriad culinary, cultural, architectural and historic offerings waiting to be discovered by you. Charge or gas up the car, make the airline reservations, get on the bike and come try it on - we'll be waiting for you on the porch.

314 St George Street, St. Augustine
$1,000,000
6 Beds ⋅ 5 Baths ⋅ 2061695 MLS
Back on market due to buyer financing fell through. Beautiful large and so much history entwined in this historical home. The home needs some major TLC renovation and roof but has good bones with solid concrete foundation and most importantly history and LOCATION!! As you walk into this home, one can feel the historical feel about it. As you enter into the screened front porch you are drawn to the main entry/living room and staircase. Imagine a crackling fireplace in cold Florida winter or cool nights with a beautiful original pine flooring throughout to walk on. A formal dining area and kitchen with handcrafted cabinets since the 1900's. A former butler's pantry with room on the side for pantry. Let your imagination run to restore to once was! Upstairs consist of so much potential once renovated. The Genovar's had 2 suites in past with own kitchenettes; the plumbing still exists. 5 bathrooms upstairs with jack jill bathrooms The garage apartment has a kitchen, living room, bathroom and two spacious bedrooms. The garage apartment is on same water meter but different electric meter.

271 St George Street, St. Augustine
$925,000
3 Beds ⋅ 4 Baths ⋅ 2097228 MLS
Welcome to your perfect retreat in the heart of downtown St. Augustine! This stunning 2021 custom-built home comes fully furnished and thoughtfully decorated, ready to embrace its new owner. Designed with care, it features soaring ceilings and an open living area that welcomes natural light, creating an inviting space for gatherings. You can walk to all the sites! The charming front porch beckons you to unwind with a cool breeze, while the expansive back porch offers additional outdoor serenity. The 1st floor master suite is a peaceful haven with a beautifully appointed bathroom. Upstairs, two guest bedrooms share a full bath plus small office area. The custom Kitchen is a show-stopper! The butler kitchen and pantry simplify entertaining and food prep. The well maintained, low-maintenance yard showcases native plants and zero-scape charm. Alley access and extra parking in back. This home is a perfect blend of historic charm and modern conveniences. High and dry, no flooding. No HOA!

17 Hope Street, St. Augustine
$920,000
4 Beds ⋅ 3 Baths ⋅ 2063787 MLS
4 Bedroom 3 Bath Pool Home in the Heart of Historic St. Augustine! Built in 2015! Step into timeless charm with modern luxury in this rare newer-construction home located minutes from the heart of downtown St Augustine. Short walk to everything this city has to offer. Built to higher elevation standards (9 ft elevation above sea level) this stunning residence stands apart in a market filled with turn-of-the-century homes. ✨ Key Features: Heated Saltwater Lap Pool - Perfect for year-round enjoyment *Elegant Interior Design - 10-ft ceilings, crown molding, open-concept layout *Gourmet Chef's Kitchen Granite countertops, stainless appliances, gas range, and French-door fridge with double pull-out freezers *Cozy Living Room Stack-stone gas fireplace creates a warm, inviting ambiance *Smart Home Ready - Automated lighting for added convenience *Serene Backyard Oasis - Paver patio ideal for outdoor dining and relaxation *Available Fully Furni Ideal Location: Located on one of St. Augustine's most sought-after streets Close to wedding venues Minutes to the Florida's beaches, kids attractions, and shopping Just minutes from historic downtown, attractions, world-class dining, and nightlife. Walk to sunset boat cruises, historic tours, and live music venues. High and dry 9 ft elevation Spacious layout sleeps up to 10 guests *Ranked in the #1 Airbnb market in the country *This exceptional home is a rare opportunity to own a piece of St. Augustine's charm with the reliability and features of modern construction. Whether you're looking for a primary residence, vacation getaway, or high-yield investment, this home checks every box. =Þ Don't waitschedule your private tour today!

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

9 Saragossa Street, St. Augustine
$824,000
5 Beds ⋅ 3 Baths ⋅ 2152392 MLS
Charming triplex in a friendly neighborhood located near Flagler College, Downtown, and Uptown San Marco. High-and-dry with an exceptional 12.5 ft first-floor elevation, this property is located in Flood Zone X, where lenders do not require any flood insurance. The property features three distinct income-producing units, all with in-unit laundry. Unit 1 offers 1 bed/1 bath. Unit 2, the largest, features 2 beds/1 bath. Unit 3, the upstairs unit, includes 2 beds/1 bath, a newly renovated kitchen, and a newly added washer and dryer. Ample off-street parking is located behind the building, preserving the picturesque front porch and yard. Long-term rental history with zoning that allows weekly rentals, making it ideal for Airbnb or short-term use. Less than one mile to Flagler College a solid investment opportunity in a highly desirable area.

37 Rohde Avenue, St. Augustine
$800,000
3 Beds ⋅ 2 Baths ⋅ 2161602 MLS
Discover the charm and character of this historic 3-bedroom, 2-bath home, set on a generous lot in a secluded residential neighborhood with close proximity to the bayfront and town. Enjoy the appeal of a peaceful setting while still being near local dining, shopping, and waterfront attractions. The multi-family lot classification also provides added potential for future development opportunities. Completely remodeled in 2020-2021, including updates to the electrical, insulation, and mechanical systems, this home offers historic character with modern improvements. A new patio and planter were added in 2022, while the roof and AC were replaced in 2024. Window tinting was added in 2026 with 20% film to help reduce solar heat transfer and glare while supporting AC efficiency. Don't miss the opportunity to own a piece of history with modern updates and incredible potential!

249 Charlotte Street, St. Augustine
$800,000
4 Beds ⋅ 4 Baths ⋅ 2153241 MLS
Fabulous professional renovation by local builder equates to newer home with historical significance. Imagine daily encounters along Lake Maria Sanchez and the historic bayfront! Stunning sunlight and beautiful finishes throughout! A chef's kitchen opens to a beautiful sunroom, large laundry room, powder room. The family room offers original brick, light and beautiful hardwood floors. Every bath offers a spa experience. Large rooms, filled with light and modern convenience with old world styling. Large private back yard with outdoor vistas of one of the prettiest streets in town. A study or library on first floor for your office AND a first floor suite with bathroom plus sunroom. Peeks of Lake Maria Sanchez from the Owner's Suite! Priced below neighboring homes, this offers you the best of both worlds: Old world luxury and modern conveniences with STR income possibilities! Just staged by Simply Dwell!

142 Washington Street, St. Augustine
$785,000
4 Beds ⋅ 3 Baths ⋅ 2093841 MLS
2018 Lincolnville Gem with Income Potential & Guest Suite - Zoned for Nightly Rentals! Two versatile units on one city lot, just minutes from the heart of the Oldest City and all its historic charm. Built in 2018 and zoned for nightly rentals, this thoughtfully designed property offers flexibility, comfort, and solid income potential — and is offered fully furnished. The main house features 3 bedrooms, 2 bathrooms, and spans 1,837 sq ft with an open, airy layout. Enjoy views of the San Sebastián River from the front porch upper balcony. The rear of the property includes a detached 2-car garage with an RV garage (30-amp hookup) and awesome game room. Above, the ~ 550 sq ft apartment offers 1-bedroom, 1-bath and a ample kitchenette — ideal for rental income, guests, or multigenerational living. This home is built high & dry at 10 feet above sea level with a solid stem wall foundation, offering durability and peace of mind. With low-maintenance construction, parking for 6-7 vehicles. Excellent location just moments from all downtown St. Augustine has to offer. Dining, boating, waterfront ,shopping and more. It's perfect for full-time living, a vacation home, or a high-performing rental investment. Live your dream or fund it  this Lincolnville property offers both.

239 Riberia Street, St. Augustine
$765,000
3 Beds ⋅ 1 Baths ⋅ 2146726 MLS
Sold Comps for Marketing Purposes Only

145 Paranza, St. Augustine
$760,000
3 Beds ⋅ 2 Baths ⋅ 2079924 MLS
Built in 1885 in Henry Flagler's ''MODEL LAND COMPANY'' - tastefully and extensively renovated. From the studs in, the home has spray-foam insulation (even in the attic), new drywall and paint. The heavy lifting has been completed in the kitchen featuring a 4-Burner Gas Cooktop under a wall-mount range hood, replaced cabinets & counters and both full baths are totally redone. Electric and plumbing done. Metal roof. done. Two A/C units, water softener, central vac, windows, aluminum attic stairs - you name it - except for the exterior siding, this home is renovated! It even includes the original 1905 Sears Catalog fireplace mantle.

44 Carrera Street, St. Augustine
$735,000
2 Beds ⋅ 3 Baths ⋅ 2126282 MLS
Classic Elegance in the Heart of St. Augustine's Historic District. Built in 2019, this exceptional residence blends Old World architectural charm with the confidence and comfort of modern construction. Elevated 10 feet above grade this thoughtfully designed single-level home offers two bedrooms and two-and-a-half baths, with soaring 10-foot ceilings that create a bright, gallery-inspired interior ideal for displaying fine art. Oversized windows fill the home with natural light, while ceiling fans in every room enhance comfort and style. Luxury vinyl tile flooring provides a refined aesthetic with effortless maintenance. The kitchen features quality cabinetry enhanced with ShelfGenie custom shelving, custom blinds, and functional design suited for everyday living and entertaining. Generous front and rear porches--recently refreshed and equipped with two new ceiling fans--extend the living space outdoors and invite relaxed enjoyment of the surroundings. A full-length driveway provides convenient rear access and ample guest parking, complemented by reserved on-street parking for area residents. The professionally curated no-lawn garden is serene and low-maintenance, attracting abundant birdlife. From the porch, enjoy visits from cardinals, bluebirds, chickadees, woodpeckers, red-winged blackbirds, Carolina wrens, doves, finches, and titmice. Hummingbirds frequent the feeder, while the birdbath is currently visited by migrating robins--creating a peaceful, immersive outdoor experience. The home is finished with resilient cedar siding and is located just a short walk from the St. Johns County River House Recreation Center, offering classes in dance, art, music, exercise, bridge, and more. The neighborhood is prized for its peaceful atmosphere, strong sense of community, and absence of short-term rental zoning, with an active Old City South Neighborhood Association hosting year-round social events. Ideally situated within easy walking distance of Lake Maria Sanchez, the Bayfront, Flagler College, and downtown St. Augustine's renowned dining, shopping, and cultural attractions.

307 St George Street, St. Augustine
$732,500
4 Beds ⋅ 3 Baths ⋅ 2117441 MLS
Welcome to 114 and 112 M L King Avenue, a stunning 4-bedroom, 3-bathroom home nestled in the heart of historic Lincolnville. Built in 2016 with timeless craftsmanship to match the charm of the neighborhood, this residence offers over 2,100 sq ft of thoughtfully designed living space. Step onto one of the three inviting front porches and take in vibrant community views, including the cozy coffee shop directly across the street. Inside, you'll find an open, airy floor plan with modern finishes that seamlessly blend with classic architectural details. Everything is in excellent condition - practically like new - and tastefully updated to reflect St. Augustine's unique character. The buildable lot next door can also be purchased with the home. Currently graveled and used for additional off-street parking, providing the option to construct another home or guest cottage for additional income potential. Just steps away from all that downtown St. Augustine has to offer - restaurants, art galleries, music, and history - this property is ideal as a primary residence, a second home, or a lucrative short-term rental investment. Don't miss your opportunity to own this rare combination of modern comfort, historic charm, and future development potential in one of Florida's most beloved coastal towns.

114 Martin Luther King Avenue, St. Augustine
$730,000
2 Beds ⋅ 3 Baths ⋅ 2110161 MLS
Lincolnville Luxury with Proven Rental History! This 2-bed, 2.5-bath, 1,230 SF home by Coastal Craftsmen blends superior design with an active rental record. Premium details include Ipe hardwood siding, custom powder-coated railings, a White Oak staircase screen, and hand-fabricated solid-surface countertops. The gourmet kitchen boasts Euro-style cabinetry, stainless Samsung appliances, and a sleek range hood. Open living flows to a large front porch, while the oversized back porch—with outdoor hot/cold shower—sits amid lush bamboo and palms. Upstairs, two spacious bedrooms offer panoramic views of a Spanish-moss tree canopy. Perfect for owner-occupants or investors seeking a turnkey property in historic downtown St. Augustine

103A Kings Ferry Way, St. Augustine
$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
$705,000
3 Beds ⋅ 4 Baths ⋅ 2096042 MLS
Step into the storybook charm of this 1908-built home, perfectly located in the heart of Downtown St. Augustine. Rich in character and thoughtfully updated, this property offers the ideal blend of timeless architecture, everyday comfort, and flexible living. Inside, original hardwood floors and period details set a warm, welcoming tone. The formal dining room is perfect for hosting, while the downstairs bedroom—with a private bath—offers versatility as a guest room, home office, or cozy retreat. Upstairs, the primary suite is a light-filled sanctuary featuring a wall of windows and a private balcony—an ideal spot for morning coffee or an evening wind-down. Each bedroom includes its own en suite bath, providing privacy and comfort for both residents and guests. Outside, the lush garden space creates a private, serene escapeperfect for brunch, reading in the shade, or evening dinners surrounded by greenery. But what truly sets this home apart is its unbeatable location and flexibility. Just steps from some of St. Augustine's best restaurants, local coffee shops, art galleries, and chic boutiques, you're also only minutes from the beachmaking it equally ideal as a primary residence, weekend getaway, or income-producing vacation rental. Lovingly maintained and move-in ready, this is your chance to own a piece of St. Augustine's rich historywhile enjoying the lifestyle, walkability, and charm that make this city so special.

7 Cincinnati Avenue, St. Augustine
$700,000
2 Beds ⋅ 2 Baths ⋅ 2104740 MLS
Rare opportunity in Historic St. Augustine! Built in 1900 and fully remodeled, this 2BR/2BA home is the ONLY LEGAL property on its street grandfathered and zoned as a multi-unit rental with no restrictions—ideal as a single-family residence or Airbnb. Updates include all new plumbing, electrical panel, EV charger, new roof with hurricane ties, tankless hot water heater, filtration system, LED lighting & smart thermostat. Rated a Guest Favorite on Airbnb for its location and amenities. Relax on the balcony with views of lush landscaping and charming historic homes, or stroll just steps to the Historic District with world-class dining, shops, and endless history. A true blend of charm, income potential, and prime location!! Home also has 2 DEDICATED parking spots in front of home!

6 St Andrews Court, St. Augustine
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