Anastasia Hills Homes for Sale

Welcome to Anastasia Hills, a serene and picturesque subdivision nestled along the stunning coastline of St. Augustine, Florida. This charming community is perfectly situated to offer residents the best of both worlds: the tranquility of suburban living and the vibrant lifestyle of one of America’s oldest cities. With its lush landscapes and friendly atmosphere, Anastasia Hills is an ideal place to call home.

The homes for sale in Anastasia Hills showcase a delightful mix of architectural styles, ensuring there’s something for everyone. From cozy single-family homes to more spacious designs, each property is built with quality craftsmanship and modern amenities. Many homes feature expansive yards, perfect for family gatherings or enjoying the warm Florida sunshine. With a variety of floor plans available, prospective buyers can find the perfect fit for their lifestyle and needs.

Living in Anastasia Hills means you’re just a short drive away from the pristine beaches of St. Augustine, where you can soak up the sun, swim, or enjoy water sports. The community is also conveniently located near local shops, restaurants, and highly-rated schools, making it an ideal choice for families and retirees alike.

For those seeking a peaceful yet vibrant community, Anastasia Hills offers the perfect blend of comfort and convenience. Explore the homes for sale in this enchanting neighborhood and discover the lifestyle you’ve always dreamed of. Your perfect home awaits in Anastasia Hills, where every day feels like a vacation!

Newest Anastasia Hills Homes for Sale

$1,350,000

4 Beds ⋅ 4 Baths ⋅ 2160686 MLS

An exquisite coastal retreat located east of A1A in the heart of St. Augustine. Perfectly positioned just steps from the beach, this completely remodeled home offers breathtaking ocean views and an effortless blend of sophistication and comfort. From the moment you step inside, a spacious entryway welcomes you into a thoughtfully designed open floor plan adorned with tile floors throughout. The gourmet kitchen is a chef's dream, featuring white cabinetry, quartz countertops, a large island, a gas stove with a pot filler, two sinks, a wine fridge, and ample space for entertaining. The fireplace adds warmth and ambiance, creating an inviting atmosphere for gatherings, while the expansive balcony offers scenic ocean views, soothing sounds of the ocean and enjoy the coastal breeze. This stunning residence boasts four bedrooms, with two downstairs and two upstairs, offering privacy and flexibility. One of the downstairs bedrooms is a private suite, complete with an en-suite bathroom, a kitchenette, and French doors leading to the back patio, making it ideal for guests or multi-generational living. The primary suite upstairs is a true sanctuary, featuring a separate home office space and ample closet storage. Designed for both relaxation and recreation, the backyard is an entertainer's paradise. Take a dip in the sparkling heated, saltwater pool with a hot tub and sun deck, perfect your short game on the private putting green, or simply unwind in this serene coastal oasis. The two-car garage provides convenience, while short-term rental approval offers an incredible investment opportunity. Pool (2023), Roof (2023), HVAC (2020) Flood Zone X.

5497 Pelican Way, St. Augustine

Courtesy of COLDWELL BANKER PREMIER PROPERTIES

Listing courtesy of COLDWELL BANKER PREMIER PROPERTIES.

Listing courtesy of DORI NUGENT from COLDWELL BANKER PREMIER PROPERTIES.

$1,300,000

2 Beds ⋅ 1 Baths ⋅ 260335 MLS

Welcome to the Pearl. Built in 1959 with cypress timbers, this beach getaway truly is the pearl of the beach. Thoughtfully designed for open-concept living, the cozy two-bedroom, one-bath cottage has a covered front porch and a spacious fully fenced backyard, with an outdoor shower and brick patio. Completely renovated from the studs out, the Pearl is fully turnkey and sold furnished. This treasured beach cottage has a strong rental history. Many beach memories have been made in this home, just a three-minute walk from Crescent/Butler Beach. Purchase the property next door (4955 Medoras Avenue) and create a family compound!

4969 Medoras Ave, St Augustine

Courtesy of Beach Town Realty of St Augustine

$1,500,000

3 Beds ⋅ 2 Baths ⋅ 260331 MLS

Welcome to the Mermaid, located a three-minute walk from Crescent/Butler Beach. This beautiful open-concept beach cottage has three bedrooms and two full baths, including a separate guest suite with bath. Enjoy the sound of the ocean from the covered front porch or rooftop deck, while the generous backyard and patio offer ample outdoor living space. The owners have meticulously maintained and improved this home. Fully turnkey and sold furnished, it features a newer roof, A/C, updated kitchen and baths, and excellent storm resilience thanks to its elevated setting. A one-car garage provides ample storage, and the oversized lot offers abundant onsite parking. Ideally suited as a year-round beach getaway with a strong rental history, the home would also serve as a comfortable primary residence. Purchase the property next door (4969 Medoras Avenue) and create a family compound!

4955 Medoras Ave, St Augustine

Courtesy of Beach Town Realty of St Augustine

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.