Homes for Sale with a Pool in St. Augustine, FL

Impeccably clean, bright, & beautifully open, this newer POOL home offers spacious, elevated Florida living. Situated on a fully privacy-FENCED CORNER LOT, it delivers openness & privacy both inside & out. Inside, large rooms & HIGH CEILINGS create an airy expansive feel. The open layout is anchored by the kitchen with quartz countertops & a large QUARTZ island flowing seamlessly into the living & dining areas. Triple cascading sliding doors extend the living space to a SCREENED PATIO with TV hookup, overlooking the pavered POOL area & stone FIRE PIT—perfect for year-round enjoyment. The THREE-CAR GARAGE provides even more room for vehicles, storage, or hobbies. A SPLIT FLOOR PLAN includes four spacious bedrooms & three bathrooms, with a primary suite featuring double vanities, a tray ceiling, & multiple closets, including a WALK-IN. Convenient to beaches, I-95, & historic downtown, yet removed from congestion, this home delivers space & outdoor living that define elevated FL living.

23 Gypsum Place, St. Augustine

$364,500

4 Beds ⋅ 2 Baths ⋅ 2125954 MLS

Welcome to this well-maintained home in a desirable St. Augustine location, offering comfort, functionality, and thoughtful updates throughout. The interior features updated tile flooring, providing a clean, modern look that is both stylish and easy to maintain. The open and inviting layout is ideal for everyday living and entertaining. Step outside to enjoy the backyard retreat, complete with an above-ground pool that conveys with the property—Fully Fenced! Perfect for relaxing or hosting gatherings. The home is located in a community with a low HOA, adding to its overall appeal. Conveniently situated near shopping, dining, schools, and major roadways, with easy access to historic downtown St. Augustine and area beaches. This home presents a wonderful opportunity to enjoy Florida living with practical upgrades already in place.

176 Falcon Ridge Road, St. Augustine

$800,000

3 Beds ⋅ 2 Baths ⋅ 2120784 MLS

Located in one of Vilano Beach's most sought-after pockets, this updated coastal retreat offers a strong blend of comfort, design, and income potential. The home has been thoughtfully improved with a new HVAC compressor and return unit, new sump pump, Hardie board siding, paver driveway and walkways, updated landscaping, outdoor shower, electric pool heater, new pool pump and filter, new front door, outdoor lighting, and refreshed kitchen appliances. Inside, the en suite bath has been tastefully updated, and the home comes fully furnished. A private pool, plantation shutters, and a generous lot elevate the experience. Currently an active short-term rental with consistent annual returns for the past four years, while also serving as a personal getaway for the owners. Less than three miles to Historic Downtown St. Augustine and walking distance to the beach.

409 Seventeenth Street, St. Augustine

$1,900,000

4 Beds ⋅ 5 Baths ⋅ 2118899 MLS

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

9 Bonita Bay Drive, St. Augustine

$1,899,000

5 Beds ⋅ 4 Baths ⋅ 2118121 MLS

Back on market due to NO fault of sellers-second chances don't come often!! Introducing a modern expression of estate living within Equestrian Way at Whitelock Farms-effortlessly refined across 5.73 private, gated acres. Commanding nearly 4,000 square feet of refined interior living space, complemented by serene outdoor spaces, additional private in-law living, and charming barn and chicken coop, this remarkable residence offers a true sanctuary for the most discerning buyer. Past the gated entrance and manicured lawn, the stately exterior design welcomes you to the immaculately maintained residence. Inside, grand vaulted ceilings, open living spaces, and elegant finishes provide an atmosphere of effortless luxury. Downstairs features a grand foyer entry, the primary suite and accompanying en-suite, complete with custom closets. Downstairs also features a formal dining space, gourmet kitchen, and primary living space with sweeping views of the pool and pastures The kitchen and living room serve as the heart of the home, with ample natural light, perfect for both intimate gatherings and elevated hosting. Estate living and entertaining are all the more so enjoyed outside, poolside under the covered lanai with ample seating, fireplace, and outdoor kitchen. The views are nothing short of picturesque-pool and spa, pasture, barn, and equine or animal companions (should you desire) perfectly framed by the lush tree-lined backdrop. With five bedrooms and three-and-a-half baths in the primary residence alone, the home offers expansive accommodations. Upstairs you will find four ample sized bedrooms, two full baths, all conveniently arranged in a split layout, connected by a catwalk. All rooms offer sweeping pasture and lawn views. The detached in-law suite complete with a full bath, closet and its own garage space, is the perfect space for multi-generational living, office, gym, or whatever you envision. With 5.73 usable acres, the acreage offers endless possibilities, whether for additional pastures, expanded equestrian facilities, or future enhancements tailored to your vision. With plenty of acreage left untouched for privacy, there is ample room to accommodate future additions-whether that be a sports court, car storage, additional pasture space, and the like. The charming barn features three 12x12 stalls with runouts, a dedicated tack room, and easy access to the surrounding pastures. Along the right perimeter of the property, there is a second gated entry point for easy access to the barn and rear of the property for hay or supply deliveries. Residents of Whitelock Farms enjoy access to community equestrian amenities, including maintained bridle trails, multiple riding arenas, and shared training spaces offering an immersive equestrian lifestyle surrounded by both nature and community. There are dressage, hunter/jumper arenas (fenced options with footing and jumps in large grass fields), round pen for exercise lunging, and a space to pattern barrels. Footing is regularly dragged, and trails are maintained. There is a designated path with the option to trailer to the many multi-discipline arenas. Additional details include all fencing has been freshly painted black (Nov. 2025), new roof will be installed on both the main home and detached in-law suite (or credit offered), new septic installed 2024, newer AC units (2-3 years), pool pump (4 years), hot water heater (2025), barn (2022), outdoor kitchen (2024), and porch gas fireplace (2023). The residence is immaculately maintained. A residence of this caliber is a rare offering. Experience all this property has to offer for yourself with a private showing.

139 Foxcraft Street, St. Augustine

$1,199,777

5 Beds ⋅ 5 Baths ⋅ 2115547 MLS

$10,000 towards rate buy down or closing costs!! John's Island amenities center now open. Welcome to this exceptional custom-built home. Built in 2024 located in the highly sought-after Courtney Oaks at Johns Island, Silverleaf. Offering 5 bedrooms, 3 full baths, and 2 half baths across 3,458 square feet, this elegant home sits on a half-acre homesite within a private gated community. Designed with luxury and functionality in mind, this home features an open floor plan concept with vaulted ceilings in the living room, coffered ceilings in the dining room, and laminate plank flooring throughout & 18x18 ceramic tile in the baths and laundry room. A flex space with glass French doors greets you upon entry--ideal for a home office or den. Living Room offers a 74'' Horizontal fireplace, custom built-ins, in ceiling surround sound and multi-slide patio doors allowing for a fabulous view of the sparkling pool. Floor outlets are conveniently placed in the living room, den, and office for flexible furniture layouts. The gourmet kitchen boasts Samsung stainless steel appliances, Built-in wall oven & microwave, a farmhouse sink, quartz countertops & extended island that seats 6, 42-inch upgraded cabinetry, under-cabinet lighting, walk-in pantry and a reverse osmosis system. The primary suite offers tray ceilings, a sitting area, walk-in closet, and a spa-inspired bath with a free-standing tub and frameless double-entry shower. Bay windows enhance both the primary and fourth bedrooms with the 4th bedroom including seating with storage. Additional highlights include a Generac whole-home generator, central vacuum, built-in sound system, irrigation, and water softener. Enjoy year-round outdoor living in the custom screened saltwater heated pool and spa, featuring a paver pool deck and dedicated pool half bath. A paver driveway and three-car garage with epoxy resin flooring provide ample parking and storage. Silverleaf offers resort style amenities including community pools with splash pad, pickleball, tennis courts, fitness center, dog park, clubhouses, walking trails, and family-friendly community in a prime St. Augustine location. Just minutes to shopping, dining, and top-rated schools.

295 Pine Grove Point, St. Augustine

$735,900

3 Beds ⋅ 2 Baths ⋅ 2113373 MLS

Welcome to prairie creek, voted the best neighborhood in St. Augustine. This exceptional three bedroom, two bathroom home sits majestically on a full acre of beautifully maintained property, offering the perfect blend of spacious living and natural tranquility. Backing up to the river and large preserve ensuring no future building. Step inside this thoughtfully designed open floor plan with 2,119 square feet and discover a space that has been completely updated throughout. New roof, new AC, updated pool, new plumbing including water filtration, softener and a tankless gas hot water heater. Enjoy the heart of the home in the spacious remodeled gourmet kitchen with plenty of counter space, storage and a butlers pantry to keep everything organized. With lots of tasteful upgrades, including the under lite italian marble countertops, upgraded cabinets with pull-outs, a gas range featuring air fly technology, large hood vent, pot filler and all new black stainless appliance

3613 Crazy Horse Trail, St. Augustine

$869,000

3 Beds ⋅ 3 Baths ⋅ 2113264 MLS

With a location in the heart of Historic Downtown St. Augustine and only minutes to Vilano Beach, the Homes of 7 Sebastian Avenue effortlessly blend sophisticated design and luxury living. Developed by Ocean Life Homes, this exclusive four unit townhouse development is designed to comfortably accommodate those looking for low maintenance and a permanent residence, second home, or profitable investment opportunity. Each unit will boast a spacious two story, three bedroom, two and a half bath floor plan with a one car garage, and private 7x12 in ground pool. Interior finishings have been artfully curated to ensure only the highest quality products are utilized throughout each home. Outside, xeriscaping will be implemented to achieve minimal water usage with little to no irrigation required and pool maintenance will be included in the HOA fee. This is a rare opportunity to own a new construction luxury townhome, surrounded by shopping, dining, and walking distance to historic attractions in the epicenter of the Nation's Oldest City. For further details and specifications, contact us today.

7 Sebastian Avenue Unit D, St. Augustine

$859,000

3 Beds ⋅ 3 Baths ⋅ 2113265 MLS

With a location in the heart of Historic Downtown St. Augustine and only minutes to Vilano Beach, the Homes of 7 Sebastian Avenue effortlessly blend sophisticated design and luxury living. Developed by Ocean Life Homes, this exclusive four unit townhouse development is designed to comfortably accommodate those looking for low maintenance and a permanent residence, second home, or profitable investment opportunity. Each unit will boast a spacious two story, three bedroom, two and a half bath floor plan with a one car garage, and private 7x12 in ground pool. Interior finishings have been artfully curated to ensure only the highest quality products are utilized throughout each home. Outside, xeriscaping will be implemented to achieve minimal water usage with little to no irrigation required and pool maintenance will be included in the HOA fee. This is a rare opportunity to own a new construction luxury townhome, surrounded by shopping, dining, and walking distance to historic attractions in the epicenter of the Nation's Oldest City. For further details and specifications, contact us today.

7 Sebastian Avenue Unit C, St. Augustine

$675,000

3 Beds ⋅ 2 Baths ⋅ 2108550 MLS

Welcome to your new Dream Home - beautiful waterfront property that offers bulkheaded lot and provides spacious backyard for your own peaceful outdoor Oasis. Enjoy true freedom of this home ownership, as there are no HOA or CDD fees. This properly sits on half an acre of land, features large screened heated saltwater pool, covered lakefront gazebo, spacious fully fenced back yard, and private fishing pier. House features an open floor plan filled with abundance of natural light. The backyard melts into the spring-fed lake, providing a private retreat for quiet mornings and serene evenings. Interior of home has been upgraded with newer appliances and A/C, recently installed septic tank, brand new roof - September 2025. New exterior paint, pool and deck remodel - January 2026. Property comes with transferable termite bond, November 2025 Home inspection report is available. Centrally located - close to Historic downtown, I-95, and the beaches. This property combines the best of Florida living with desirable features and strong investment potential, all without HOA, short-term rental restrictions and no flood zones. This property has been well-established, profitable, and highly rated short-term rental in the last 4 years. Proof of earnings is available. Turnkey and ready for your immediate enjoyment or rental operation. Schedule your private showing.

4041 Pine Run Circle, St. Augustine

$6,990,000

5 Beds ⋅ 8 Baths ⋅ 1186603 MLS

Mediterranean Luxury Riverfront Estate, a private gated St Johns River Estate built on 1.43 acres is a slice of paradise offering resort style amenities designed for entertaining. Custom built to perfection spanning over 6268 sqft 5-bedroom, 8 bath estate expresses the ultimate in Florida outdoor luxury living experience. The main house layout starts with a 2 story grand entry and a sweeping custom designed iron staircase, second story interior balcony, wine cellar, gourmet chefs kitchen, large billiard & theater room and 1st floor owners retreat overlooking resort pool with river views. In addition to the main house, you will find a separate caretakers quarters/guest cottage with 3bedrooms/2baths for privacy. This stunning estate includes 7 car garage & 25x50 AC and heated work garage. Enter through the 6x8 solid French wood door into a stunning 6,268 Sqft Mediterranean home. You are greeted by the great room that features a gas & wood fireplace with custom bookcases and stunning 22ft 2 steps knock down custom coffered wood ceilings. The exquisite gourmet chef's kitchen features stainless steel appliances, a Samsung double door refrigerator, a large breakfast bar with custom cabinets and a large walk-in pantry. The open dining room features great views, with a built-in butler's pantry/bar with cabinet lighting. Open the French doors which lead you to a 57' Veranda overlooking the pool and riverfront. The private owners retreat boasts 10' ceilings with hand painted murals, a large gas fireplace, California Berber carpeting, custom silk window treatments and beautiful French doors leading out to lanai. The owners bath greats you with imported Italian Stones, Italian granite, and custom workmanship. Relax in the steam dual rain shower. Take the wrought iron spiral staircase which leads you to the atrium with wood floors & 10' dome. As you enter the carpeted theatre room you are welcomed with 7 surround sound speakers with dark ceilings and black out drapes, perfect for a movie night. The billiard room showcases hardwood floors, with a gas fireplace, custom bookcases, and a wet bar that features granite countertops with built in cabinets. This Spectacular Waterfront Estate Lot features 107ft Bulkhead WF with St. Johns River views. Enjoy a tin roof boat house with a deep-water dock. The salt water heated pool features water purification/self-cleaning filtration. The pool is surrounded with Italian Stone, custom walk-in waterfall, spa, swim up bar, and a 4' beach island. This home has a tropical landscape with outdoor lighting, gated grand entryway, a wrought iron fence, and a sprinkler system. Relax at the summer kitchen or by the outdoor fireplace. An outside cabana bath features storage and an outdoor lounge area. Enjoy your 3BR|2B 1250Sqft guest cottage, with a living room, kitchen, and private parking. Find your oasis at this private protected cove home.

8289 Colee Cove Road, St. Augustine

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