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$6,900,000
8 Beds ⋅ 7 Baths ⋅ 7,889 SqFt. ⋅ 2 DOM
Steeped in the rich history of St. Augustine and set along the shimmering Intracoastal Waterway, this extraordinary Davis Shores waterfront estate is a rare offering where historic significance meets modern luxury. Once the residence of Elizabeth Davis-the namesake behind the iconic Davis Shores neighborhood-this remarkable property is one of the community's original homes, thoughtfully preserved while offering nearly 8,000 square feet of exceptional waterfront living with unparalleled views of the Intracoastal and the skyline of historic downtown St. Augustine. Privately positioned on just over half an acre, the estate welcomes you with a gated circular drive and an impressive arrival that hints at the grandeur within. Designed for both elegant entertaining and comfortable everyday living, the main level features a spacious kitchen that captures uninterrupted water views while overlooking the expansive living room, allowing the beauty of the Intracoastal to become part of every gathering. Double glass doors open to a sophisticated formal dining room, while a second set leads to a warm and inviting family room or den, creating multiple spaces to entertain or unwind. The first floor also offers three spacious guest bedrooms connected by a shared bath, including one unforgettable bedroom featuring a custom-built pirate ship - a whimsical space certain to become a favorite for family and guests alike. A spiral staircase leads to the second level, where architectural character continues throughout. The private primary suite is nestled within an atrium-inspired setting and features its own waterfront balcony, a walk-in closet, an oversized walk-in shower, and both a full bath and private half bath, creating a true owner's retreat. Upstairs also offers a generous bonus family room, additional guest bedrooms, a hidden room discreetly tucked away off the loft, and two charming bedrooms complete with hideaway lofts, adding a sense of discovery and individuality rarely found in today's homes. Beyond the residence, the outdoor living experience is nothing short of spectacular. Framed by mature landscaping and sweeping water views, the expansive backyard features a sparkling pool, private dock, protective bulkhead, and endless opportunities to embrace the waterfront lifestyle-from boating and paddleboarding to watching dolphins play and enjoying spectacular sunsets over the Intracoastal with the lights of historic downtown St. Augustine creating an unforgettable evening backdrop. Rich in history, extraordinary in scale, and unmatched in location, this landmark estate offers a once-in-a-generation opportunity to own a piece of St. Augustine's legacy. Combining timeless architectural charm with the luxury of waterfront living just minutes from world-class dining, shopping, marinas, and the nation's oldest city, this is far more than a home-it is a piece of history destined to become part of your family's story. Be sure to watch the video!

49 Dolphin Drive, St. Augustine
$740,000
6 Beds ⋅ 3 Baths ⋅ 2,728 SqFt. ⋅ 5 DOM
Welcome to this beautifully appointed 6-bedroom, 3-bath home designed for comfortable living and effortless entertaining. The open floor plan showcases vaulted ceilings, abundant natural light, and a spacious great room that flows into the gourmet kitchen featuring granite countertops, stainless steel appliances, double wall ovens, rich wood cabinetry, and an oversized island with seating. The generous primary suite offers walk-in closets, while the additional bedrooms provide plenty of space for family or guests. Step outside to your private backyard retreat with an in-ground pool and spa, expansive paver patio, covered outdoor kitchen, and multiple areas to relax or entertain. Completing the home is an impressive 3-car garage with epoxy floors, built-in storage, custom cabinetry, and ample workspace. This home truly has it all!

25 Summer Sun Way, St. Augustine
$2,950,000
6 Beds ⋅ 6 Baths ⋅ 3,286 SqFt. ⋅ 6 DOM
Discover one of Northeast Florida's premier equestrian estates on 19+ high-and-dry acres. This exceptional property features a fully renovated 4-bedroom, 3.5-bath brick home with designer finishes, a new resort-style pool, outdoor shower, and separate smokehouse. The equestrian facilities are unmatched, including a 28-stall barn, a 500 sqft tack room with new HVAC, laundry / bath, plus an attached 2-bedroom, 1-bath apartment. Ride year-round in the 200' x 120' arena with premium GGT footing installed by Longwood Arenas. Additional highlights include 3 new wells, 5 wash stalls with fly spray system, 15 lush paddocks, 11 featuring 12' x 12' run-in shelters with lightning protection, and exceptional infrastructure designed for horse and rider. An elite turnkey equestrian compound ready for its next owner.

2005 Bennett Road, St. Augustine
$1,499,000
7 Beds ⋅ 5 Baths ⋅ 3,214 SqFt. ⋅ 12 DOM
Historic Downtown St. Augustine Home With Detached Apartment | Prime Corner Lot | Abundant Parking | Exceptional Flexibility! One of the lowest price-per-square-foot opportunities currently available downtown. This distinctive home offers the perfect blend of historic charm, contemporary style, and established income potential. Situated on a desirable corner lot with abundant parking -- a truly valuable advantage in the downtown area -- it is just a short walk to City Gates, St. George Street, Castillo de San Marcos, shops, restaurants, nightlife, and live music. This unique offering combines a stylish main residence with a detached income-producing apartment, providing exceptional flexibility for an owner-occupant, investor, multi-generational living arrangement, or anyone seeking a downtown lifestyle with income potential. Both spaces are currently operating as successful short-term rentals with annual gross rental income exceeding six figures. The spacious main residence offers approximately 2,590 square feet with 5 bedrooms and 3.5 bathrooms, featuring a stylish blend of historic character and modern updates. Thoughtful finishes, unique design elements, and versatile living spaces create a home full of personality and charm. The detached 2-bedroom, 1-bath apartment adds approximately 624 square feet of additional living space and includes its own full kitchen, laundry, and private entrance. Multiple balconies, decks, and patio areas provide exceptional outdoor spaces for entertaining and relaxing. Additional flexible space located below the apartment provides valuable storage and utility space with potential for future customization. With a prime corner lot, abundant parking, a walkable downtown location, historic appeal, multiple living spaces, and proven income from both residences, this is an exceptional opportunity to own a distinctive downtown home offering lifestyle, flexibility, and investment potential.

13 Rohde Avenue, St. Augustine
$800,000
7 Beds ⋅ 5 Baths ⋅ 2,888 SqFt. ⋅ 20 DOM
Investor's Dream by the Coast! This high-performing triplex in Crescent Beach offers an incredible opportunity just a short walk to both the river and the beach. With approx. $110K in gross income, it's ideal for short, mid, or long-term rental strategies. Each unit features its own entrance, kitchen, and private outdoor space. With a 4.9+ star Airbnb rating, a strong rental history, and consistent occupancy, this is a solid income-producing asset. Offered fully furnished with stylish interiors, it's a ready-made addition to any investment portfolio. Full financial summary available upon request.

7018 Middleton Avenue, St. Augustine
$1,450,000
6 Beds ⋅ 1,854 SqFt. ⋅ 23 DOM
Turn-Key 5-Unit Airbnb Property in the Heart of Historic Downtown St. Augustine - Fully Furnished & Ready for Immediate Income! Step into a rare opportunity to own a successful, established short-term rental property just steps from St. Augustine's iconic attractions. This meticulously restored multi-unit gem has been thoughtfully operated as a high-performing Airbnb, delivering consistent bookings and glowing guest reviews thanks to its unbeatable location and charming, private accommodations. Offered fully furnished, equipped, and completely turn-key, the new owner can seamlessly continue operations without missing a beat. Nestled in the heart of downtown St. Augustine, guests are surrounded by world-class history, dining, shopping, and entertainment. Rental history and performance data are available upon request, along with a detailed list of extensive updates and upgrades completed over the years. No flooding - FLOOD ZONE X. No HOA. Walk to everything downtown!

53 Sanford Street, St. Augustine
$1,250,000
7 Beds ⋅ 5 Baths ⋅ 4,320 SqFt. ⋅ 27 DOM
Exceptional mixed-use investment opportunity on Anastasia Island, offering a rare combination of immediate cash flow, exceptional visibility, and long-term redevelopment potential. Positioned directly on A1A with outstanding frontage, this unique property spans two parcels on an oversized double-deep lot, creating a true land play in one of Northeast Florida's most desirable coastal markets. The property consists of five income-producing units with a diversified mix of commercial and residential space. The ground level features two well-maintained office suites, each offering approximately with an ADA-compliant bathroom. One of the commercial suites has been thoughtfully configured to include an additional one-bedroom, one-bathroom apartment in the rear, creating an additional residential income stream while maintaining functional commercial space. Upstairs are two spacious three-bedroom, two-bathroom residences with generous floor plans, ideal for long-term rentals, executive housing, or short-term vacation rentals. This unique blend of commercial and residential uses provides investors with multiple revenue streams while offering flexibility to adapt the property as market demands evolve. The oversized double-parcel site provides ample on-site parking, an increasingly valuable asset for both commercial tenants and residential occupants. Located just moments from the beach, restaurants, shopping, and some of Anastasia Island's most popular destinations, the property benefits from exceptional exposure, strong traffic counts, and consistent demand from both businesses and residents. Whether you're seeking a stabilized mixed-use investment, a value-add opportunity, or a strategic land acquisition along the A1A corridor, properties of this caliber rarely become available. Prime frontage, five income-producing units, flexible mixed-use configuration, multiple revenue streams, and the long-term value of a double-deep parcel combine to create an exceptional investment opportunity in one of the most sought-after locations on Anastasia Island.

5961 A1a S, St. Augustine
$920,000
7 Beds ⋅ 3 Baths ⋅ 3,138 SqFt. ⋅ 36 DOM
Welcome to your private 5-acre retreat in St. Augustine! This beautifully updated 7-bedroom, 3-bath home offers the perfect blend of country living and modern convenience, just minutes from shopping, beaches, and historic downtown St. Augustine. Recent upgrades include fresh interior and exterior paint, new flooring in the living room, kitchen, and laundry room, a fully remodeled primary bathroom, and a brand-new roof to be installed prior to closing. The flexible floor plan features a home office with exterior access, a spacious bonus room, and a large heated and cooled enclosed porch. Additional features include stainless steel appliances, a gas fireplace, reverse osmosis water system, stocked pond, abundant storage, and a 28x60 barn with 8 stalls, water, electric, tack rooms, feed room, and wash rack. A rare opportunity to own a move-in-ready acreage property in one of St. Augustine's most desirable locations. No HOA. Bring your boats, RVs, and outdoor toys!

2445 Pellicer Road, St. Augustine
$799,000
6 Beds ⋅ 4 Baths ⋅ 3,680 SqFt. ⋅ 39 DOM
WOW!! Seller offering $10,000 towards buyer's closing costs & prepaids or rate buy-down, with acceptable offer ! This beautifully crafted exceptional custom home by Landon Homes is situated on one of the most desirable lots in the neighborhood, open and spacious in the front with exceptional privacy in the rear. Thoughtfully designed with quality construction, timeless finishes, and superior craftsmanship, this home offers the perfect combination of luxury, comfort, and privacy. Inside, you'll find 10-foot ceilings, level 5 smooth wall finishes, crown molding throughout the main living areas, and an impressive 9-box coffered ceiling. The spacious kitchen features 42-inch solid full-overlap cabinetry, granite countertops, soft-close drawers, and abundant storage. A gas fireplace with custom mantel and granite hearth creates a stunning focal point, while surround sound speakers make entertaining effortless. The owner's suite offers a luxurious retreat with a 6-foot soaking tub and a convenient pass-through from the primary closet directly to the laundry room. Additional features include solid bamboo flooring in the office and living/dining areas, sound-deadening drywall throughout the home, an oversized two-car garage, and energy-efficient ZIP System construction. Step outside to your private backyard oasis featuring a heated saltwater pool, beautiful Shellock Luxury Pavers, and exceptional privacy, creating the perfect setting for year-round Florida living. For added peace of mind, this home has been extensively updated and meticulously maintained by the original owner. Recent improvements include a new driveway, walkway, landscaping, and exterior paint (2023), interior paint refresh (2026), brand-new carpet throughout (June 2026), new pool screens (2026), new pool pump (2026), A/C indoor unit and coil replacement (2025), and a new outdoor compressor (2026). With custom construction, high-end finishes, major system updates, and one of the best homesites in the community, this exceptional home is truly a rare find.

99 Weathered Edge Drive, St. Augustine
$959,000
6 Beds ⋅ 4 Baths ⋅ 4,639 SqFt. ⋅ 40 DOM
Welcome to Palencia, one of St. Augustine's most prestigious master-planned golf communities. This Toll Bros. built Grand Bay Model, located in the Sebastian Sq. section of Palencia, features 6 generously sized bedrooms, 4bathrooms, a second-floor game room plus additional bonus room, and storage galore. The well-planned kitchen has granite countertops, stainless steel appliances, and a center island opening to a large bright family room with a gas fireplace and built in bookshelves, and plantation shutters. The family room overlooks a spacious backyard with plenty of room for a pool. Upon entering you are greeted with 9 Ft. Tray ceilings, and beautiful moldings adorning the entry foyer, dining room and living room. The large primary bedroom features a bay window with seating area, his and hers closets and a door to the screened lanai. The .43-acre corner lot backs one of Palencia's many pocket parks ideal for extended family entertainment. Palencia amenities include security gate, 10 tennis courts, 6 pickle ball courts,2 bocce courts, 3 swimming pools, dog park, walking trails ,a boardwalk to the intercoastal, multiple playgrounds and a full gym.

443 Sebastian Square, St. Augustine
$624,900
6 Beds ⋅ 4 Baths ⋅ 3,547 SqFt. ⋅ 54 DOM
This beautifully designed DreamFinders home is perfect for a large family. Designed for today's modern family, this expansive floor plan offers room for everyone. Upon entering, you'll find a spacious living room and dining room combination that provides flexibility for entertaining. The kitchen has a huge eat in space and family room. There is a downstairs bedroom with full bath for convenience, perfect for extended family or multi generational living. Upstairs you will discover oversized bedrooms, laundry and an extra large bonus room that can serve as a media room, game room, home office or additional bedroom. Step outside and experience an entertainer's dream backyard. The oversized paver patio offers abundant space for outdoor dining and hosting friends and family. Backing to a peaceful preserve and enclosed privacy fence and plenty of room for dog zoomies or adding a pool. Johns Creek residents enjoy great amenities for the whole family. The neighborhood is located close to shopping, restaurants, schools, St Augustine, the beaches and downtown Jacksonville.

57 Huffner Hill Circle, St. Augustine
$3,125,000
7 Beds ⋅ 7 Baths ⋅ 5,920 SqFt. ⋅ 55 DOM
A private equestrian estate designed for those who value space, exceptional craftsmanship, and a lifestyle beyond the ordinary. Tucked behind the gates of the exclusive Ranch Club at Ashton Oaks, this extraordinary custom-built estate offers a rare combination of luxury, privacy, and acreage living in Northwest St. Johns County. Set on 6.6 picturesque acres with panoramic pond-to-preserve views, the property delivers a lifestyle that is increasingly difficult to find and nearly impossible to replicate. Completed in 2024, the residence encompasses 5,920 square feet of thoughtfully designed living space featuring 7 bedrooms, 6 full baths, 1 half bath, a Private in-law suite, Separate guest apartment (1,200 sf), two dedicated executive offices, and expansive entertaining spaces. Every detail reflects unparalleled quality, from custom millwork and designer lighting to Command smart home integration, whole-home audio, Wellborn cabinetry, Monogram appliances and Starlink connectivity. A Generac whole-home generator, Water filtration systems, dual gas tankless water heaters and premium finishes are just a sample of the distinctive features found throughout the home. The chef's kitchen is designed to impress with both working island and serving islands, Gas range, French door double oven with air fryer & microwave, a walk-in pantry, dedicated coffee station with auto-fill water line, and abundant custom storage. The primary retreat offers a private sanctuary with a stunning views, spa-inspired bath, custom walk in closet, dressing room, electric fireplace, and direct access to outdoor living spaces. Designed for entertaining, the panoramic screened salt water pool with dual water falls, summer kitchen, stone fireplace and extended covered lanai is sure to become a favorite gathering spot. The estate also features a stocked pond and extends into the preserve area where it backs up to Six Mile Creek and Watson Island State Forest. Cross-fenced yard area is suitable for horses, dogs, or other small livestock. Detached climate-controlled workshop with oversized bays, RV hookup (electric, water, clean-outs), added carport storage and utility area creates exceptional flexibility. Separate guest accommodations are tucked away offering an attached in-law suite in the main house a separate 1 bedroom, 1 bath apartment with private access providing multiple ideal spaces for extended stays or multi-generational living. Residents enjoy access to community bridle trails, turn-out area, and pavilion amenities within a gated enclave of only 27 homes. Located within top-rated St. Johns County schools and convenient to Jacksonville, Ponte Vedra, and historic St. Augustine, residents enjoy easy access to championship golf, beaches, state parks, boating, award-winning dining, shopping, entertainment, and endless outdoor recreation. A truly exceptional estate where luxury, privacy, technology, and lifestyle converge.

121 Ashton Oaks Drive, St. Augustine
$2,350,000
6 Beds ⋅ 5 Baths ⋅ 3,999 SqFt. ⋅ 254 DOM
178 Avenida Menendez - An Iconic Flagler-Era Residence with Panoramic Bayfront Views Exquisitely restored and meticulously maintained. The Bodley/Bennett residence is a rare Flagler-era treasure, originally built in 1910 and thoughtfully renovated between 2010 and 2012. Perched along the Matanzas River, this historic legal home commands sweeping, panoramic vistas of the St. Augustine Bayfront and the legendary Bridge of Lions, offering a lifestyle defined by elegance, heritage, and unmatched waterfront charm. Boasting 6 bedrooms and 5 full baths, this residence seamlessly blends historic character with modern comforts. Yellow pine flooring, 8'' hardwood baseboards, original five-panel doors, and grand staircases evoke timeless craftsmanship while updated systems and finishes ensure contemporary luxury. Optional 1 year home warranty provided by Fidelity National Home Warranty. The First-Floor Residence is an ideal suite for generational living or distinguished guests, featuring 2 bedrooms, 1 full bath, a spacious living room with a period gas fireplace, and a formal dining room. The chef-inspired kitchen includes a Jenn-Air gas range, stainless steel appliances, granite countertops, and espresso-finished cabinetry accented with period hardwaremarrying modern convenience with classic detail. The Second-Floor Main Residence is Designed for refined living and entertaining. This level offers 2 bedrooms, 3 full baths, an inviting living room, formal dining, and a beautifully remodeled kitchen with gas range, updated cabinetry, and rich butcher block counters. Thoughtful layouts and elevated finishes create a sense of sophistication and comfort throughout. The Third-Floor Retreat is also the pinnacle of luxury living. This floor provides 2 bedrooms, 1 full bath, and a generous walk-out terrace framing some of the most breathtaking views of the Bayfront and Bridge of Lionsa private sanctuary perfect for morning coffee, sunset entertaining, or simply soaking in St. Augustine's timeless beauty. A rare convergence of history, architecture, and premier waterfront location, this residence is not just a homeit is a statement. Perfect for collectors of historic properties, lovers of fine craftsmanship, and those who seek an elevated lifestyle in one of Florida's most cherished cities. Experience St. Augustine living at its finestwhere every detail tells a story, every view inspires, and every moment is extraordinary.

178 Avenida Menendez, St. Augustine
$2,800,000
7 Beds ⋅ 5 Baths ⋅ 5,800 SqFt. ⋅ 294 DOM
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
$1,500,000
6 Beds ⋅ 5 Baths ⋅ 3,286 SqFt. ⋅ 297 DOM
DEVELOPMENT OPPORTUNITY! WORLD GOLF VILLAGE CORRIDER!!! Package total of 6.61 ACRES WITH 280 FEET OF ROAD FRONTAGE DIRECTLY ON HEAVILY TRAVELLED STATE ROAD 16 . This particular parcel is 1.97 Acres being sold as a package with the adjacent 4.94 Acres. Currently zoned multifamily, the parcel contains multiple buildings including a 4/2.5 Single Family residence, and a 2/2 doublewide Mobile Home ... Depending on purchaser's development plans, Sellers may be willing to sell subject to multifamily, commercial, or mixed use zoning, depending upon terms and conditions.

5646-C State Road 16, St. Augustine
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