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St. Augustine Homes for Sale

Dreaming of coastal living with a touch of history? Look no further than St. Augustine, Florida! This charming city offers a diverse real estate landscape, from historic homes in the heart of the nation's oldest city to modern beachfront condos with breathtaking ocean views. Imagine strolling along cobblestone streets, enjoying world-class dining, and then returning to your own piece of paradise in this vibrant and sought-after location.

The St. Augustine housing market is attracting buyers seeking a unique blend of lifestyle and investment potential. With a strong sense of community, year-round sunshine, and a thriving arts and culture scene, St. Augustine offers an unparalleled quality of life. Whether you're searching for a family-friendly neighborhood, a luxurious waterfront retreat, or a cozy vacation home, you'll find a range of options to suit your needs and preferences.

Invest in the St. Augustine lifestyle and experience the allure of this historic gem. From the iconic Castillo de San Marcos to the beautiful beaches of Anastasia Island, the city offers endless opportunities for recreation and relaxation. Let the charm and character of St. Augustine captivate you as you explore the diverse and exciting possibilities within its real estate market. Discover your perfect home in this captivating coastal destination!

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St. Augustine Homes for Sale

$4,800,000
2159764 MLS Casa Maya Restaurant & Tequila Bar BLDG.
Constructed in 1987 as the private residence of acclaimed novelist and artist Jack D. Hunter, this distinctive two-story building was thoughtfully transformed in 2012 into one of Historic Downtown St. Augustine's most unique full-service restaurant and tequila bar destinations. Professionally renovated by John Valdez & Associates, the conversion incorporated modern commercial systems designed for restaurant use, including a fire sprinkler and suppression system, while preserving the property's architectural charm and intimate residential character. Situated on approximately 0.12± acres, the property enjoys approximately 49 feet of frontage along the brick-paved Hypolita Street and an additional 109 feet of frontage on Toques Place, providing outstanding visibility and convenient pedestrian access from both sides of the property. Enclosed by a concrete block privacy wall, the restaurant offers a rare, private courtyard setting featuring mature shade trees, lush landscaping, decorative gardens, brick pavers, ambient lighting, and multiple outdoor gathering areas that create an inviting atmosphere unlike any other in the Historic District. The property is prominently positioned along one of downtown's primary pedestrian corridors and is highly visible to vehicular traffic, sightseeing tour trains, and the millions of visitors who explore St. Augustine each year. The improvements contain approximately 3,292± square feet of heated, cooled, covered, and support areas thoughtfully designed to create multiple guest experiences throughout the property. The first floor features a fully equipped commercial kitchen, food preparation areas, manager's office, hostess and waiting area around a fireplace, customer restrooms, two covered outdoor bars, and a spacious covered courtyard dining area. The second level offers an additional bar with seating, food preparation area, customer restroom, and two covered balconies overlooking both Hypolita Street and the private courtyard, providing a unique elevated dining experience. A detached service building includes storage, dishwashing facilities, a walk-in cooler, and an additional guest restroom conveniently serving the courtyard. Operating today as "Casa Maya Restaurant & Tequila Bar", the property has been thoughtfully designed to create multiple indoor and outdoor hospitality experiences within an intimate, garden-like setting. The private courtyard serves as the focal point of the property, complete with a covered entertainment stage, open space for dancing, and inviting gathering areas illuminated by decorative lighting and mature landscaping. Its versatile layout is well suited for casual and upscale dining, specialty beverage service, private events, rehearsal dinners, weddings, corporate functions, and live entertainment. Opportunities to acquire a purpose-built hospitality property with this combination of historic character, operational versatility, exceptional ambiance, and an irreplaceable location in the heart of America's oldest city are exceedingly rare. Located at 22 Hypolita Street in the heart of the Historic District of St. Augustine, this premier restaurant location benefits from one of Florida's strongest pedestrian-oriented tourism markets. Situated just one block from the bayfront and within easy walking distance of St. George Street, the property is surrounded by nationally recognized attractions, boutique hotels, museums, art galleries, retail shops, and some of the city's most popular restaurants and entertainment venues. The Historic District welcomes millions of visitors annually, creating consistent daytime and evening foot traffic throughout the year. The area hosts numerous festivals, live music events, holiday celebrations, and cultural attractions that drive repeat visitation from both tourists and local residents. The property's central downtown location offers exceptional visibility and accessibility, making it an ideal destination for lunch, dinner, and evening dining. Guests enjoy convenient access from nearby public parking facilities, hotels, bed-and-breakfasts, the St. Augustine Bayfront, and many of the city's signature landmarks, including Castillo de San Marcos National Monument. The surrounding mix of hospitality, retail, and entertainment uses creates a vibrant, walkable environment that consistently attracts both visitors and local patrons.

22 Hypolita Street, St. Augustine

$500,000
4 Beds 3 Baths 2159676 MLS
Seller now offering a $10K credit toward closing costs and/or a rate buy-down! It's time to leave the stress of endless traffic and restrictive CDD fees behind! Welcome to Deerfield Trace, an established community peacefully tucked away from it all but still close to everything St Augustine has to offer. In this small community, you're greeted by quiet walkable streets, friendly neighbors walking dogs or riding bikes, larger lots with room to breathe, and a true sense of home. You're just a short drive to A-rated St Johns County schools, parks, shopping, St Augustine & Crescent Beaches, and historic downtown St Augustine - all the convenience and none of the stress! This lakefront home has plenty of space for everyone, with 4 spacious bedrooms, a dedicated office, a flexible loft, 3 full bathrooms, and an oversized fully fenced backyard with plenty of room for pets, play, and even a future pool - this home just begs to help you create lifelong memories with those you love most. Inside, the home offers space for everyone and everything. The front entry is wide and welcoming, with the dedicated office just as you enter. Office has French doors to close off when you need some quiet, and a built-in Murphy bed with plenty of shelf and drawer storage to accommodate guests who may need first-floor lodging. Also off the front hall is the staircase with landing and modern wrought-iron railing, and a full bathroom for guests. Rounding out the first floor is the gourmet kitchen and open concept great room. The kitchen features double wall ovens, separate glass cooktop, granite countertops, 42" all-wood soft-close cabinets, stainless steel appliances, island with breakfast bar, and a spacious pantry that's a true walk-in. The kitchen opens up to the generous dining area and comfortable living room, with French doors leading out to the extended covered lanai overlooking the lake. Solid vinyl fencing along each side offers privacy from your neighbors, while aluminum rail fencing along the back allows for serene lake views. Upstairs is the flexile loft space with new wood-look tile, perfect as a second living area, playroom, teen space, game room, or gym. An additional wall can easily be added to create a fifth bedroom if needed. Separated from the loft by a wide hallway that would make the perfect library is the peaceful and spacious owners suite, laundry, and 3 additional bedrooms. The owners suite boasts lake views, a spa-like bath with double vanity sinks, walk-in shower, separate soaking tub, and private water closet. The massive walk-in closet maximizes every inch and keeps you organized with a custom built-in storage system. Down the hall is Bedroom 2 with closet built-ins, with plenty of room for a king size bed, along with the conveniently located laundry room with wall cabinets. Around the corner and further down the upstairs hall is the newly updated shared bathroom with double vanity sinks and luxury granite countertop. The end of the upstairs hall brings you to Bedrooms 3 and 4, both with built-in closet storage and one with a walk-in closet. Additional features you'll love are fresh paint inside and out, regular HVAC maintenance, abundant closet storage in all the right places, ceiling storage racks in the garage that will stay with the home, and a washer and dryer included with the sale as well. This home lives large with space for everyone and all the comforts of home you're looking for, and it's ready for its next chapter. Made to help you entertain or just keep things cozy, live loud or just enjoy the peaceful water views - just imagine the lifelong memories you'll make along the way. Schedule your showing today and feel for yourself what this home could be for you.

219 Deerfield Glen Drive, St. Augustine

$995,000
4 Beds 4 Baths 2159611 MLS
A rare opportunity to own a property filled with character, versatility and a fascinating connection to St. Augustine history. Situated beneath a canopy of majestic oak trees on nearly two private, fully fenced acres, this unique estate was once part of the historic Wolfe Ranch, owned by the family of prominent businessman, rancher and former St. Augustine mayor Herbert E. Wolfe. According to descendants of the Wolfe family, Presidents Dwight D. Eisenhower and John F. Kennedy stayed at the property during its years as a private lodge and summer retreat. The screened swimming pool is believed to be the original lodge pool, where generations of guests gathered and spent their summers. The pool was resurfaced and retiled in 2020, along with the installation of a new screen enclosure. The estate features two separate residences offering a combined 2,790 square feet, four bedrooms and three and a half bathrooms. The main home includes a 2023 addition featuring a spacious great room, walk-in pantry, guest room with attic access and a half bathroom with an exterior door for convenient pool access. Additional improvements include a new metal roof in 2023, new AC system in 2024, new appliances in 2021, new countertops in 2022, and updated valves and water lines for the sinks and toilets in 2024. Built in 2022, the detached 800-square-foot guest house offers one bedroom, one bathroom and separate utilities for added privacy and flexibility. It is ideal for extended family, guests, multigenerational living, a private office or potential rental income. The expansive grounds provide plenty of room for entertaining, gardening, recreation or simply enjoying the peaceful surroundings. A barn constructed in 2021 includes six custom cinder block dog kennels, an outdoor sink and a convenient wash-down hose. A durable metal roof was added to the barn in 2023. An extended driveway and additional parking provide ample space for residents, guests, recreational vehicles or equipment. With no HOA or CDD, this secluded estate offers remarkable freedom and flexibility while remaining convenient to World Golf Village, historic St. Augustine, shopping, dining and major roadways. Two homes, a storied pool, a well-equipped barn, six dog kennels and nearly two acres come together to create a truly one-of-a-kind St. Augustine property.

4575 Wolfe Road, St. Augustine

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