Anastasia Hills Real Estate

Welcome to Anastasia Hills, a picturesque subdivision nestled on the enchanting Anastasia Island in sunny Florida. This charming community is a hidden gem, offering a perfect blend of coastal living and suburban tranquility. With its lush landscapes, friendly neighbors, and an array of amenities, Anastasia Hills is the ideal place for families, retirees, and anyone seeking a serene lifestyle by the beach.

Anastasia Hills boasts a variety of beautiful homes, each designed to complement the stunning natural surroundings. From cozy single-family residences to spacious modern builds, there’s something for everyone. The community is thoughtfully planned, featuring tree-lined streets and well-maintained common areas that invite leisurely strolls and family gatherings.

One of the standout features of Anastasia Hills is its proximity to some of Florida's most beautiful beaches. Just a short drive away, you can sink your toes into the soft sands of St. Augustine Beach, where the Atlantic Ocean beckons with its crystal-clear waters and vibrant sunsets. For those who enjoy outdoor activities, the nearby Anastasia State Park offers hiking trails, kayaking, and birdwatching opportunities, making it a haven for nature enthusiasts.

In addition to its natural allure, Anastasia Hills is conveniently located near excellent schools, shopping centers, and dining options, ensuring that residents have everything they need within reach. With a strong sense of community and a laid-back atmosphere, Anastasia Hills invites you to experience the best of Florida living. Come explore this delightful neighborhood and discover your dream home in this coastal paradise!

Newest Listings in Anastasia Hills

$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.

$955,000

2156954 MLS

Rare Butler Beach prime redevelopment opportunity on sought-after Atlantic View. This 50'x150' (0.14 acre) ocean-side parcel sits directly across from oceanfront homes and is just 15 yards from the beach walkover through the picturesque, protected dunes. Create a custom coastal residence in a quiet, established neighborhood of substantial beach homes. Build up to 3 stories to capture beautiful Atlantic Ocean views and refreshing sea breezes from multiple levels. The property has a County water meter in place and access to the County sewer line in the street, subject to customary connection requirements and costs. Atlantic View is one of the most sought-after streets on Anastasia Island -- a quiet, upscale residential enclave with no HOA, no CDD fees, no condo congestion, no commercial intrusion, and no short-term rental restrictions. Vacation rentals are permitted, creating exceptional flexibility for primary residence, second home, luxury spec build, or high income investment property. Bike the quiet neighborhood or cruise along the water's edge. Excellent surfing, pristine beach, and a relaxed, family-oriented residential character close at hand. The wide dunes provide protection from storms. All of this makes Atlantic View one of St. Augustine's hidden gems. A compelling opportunity to build near the beach in one of Anastasia Island's most appealing coastal settings with long-term investment potential.

5485 Atlantic, St. Augustine

Courtesy of LIGHTHOUSE REALTY ASSOCIATES

Listing courtesy of LIGHTHOUSE REALTY ASSOCIATES.

Listing courtesy of BOB W LINDSEY from LIGHTHOUSE REALTY ASSOCIATES.

$995,000

2141343 MLS

The beach lifestyle you've been dreaming of starts here. Build your custom coastal retreat on this newly available oversized homesite with potential ocean views in the desirable Anastasia Hills area of St. Augustine -- just a short walk to the beach and breathtaking Atlantic sunrises. Enjoy the perfect blend of laid-back coastal living and vibrant local charm, with easy access to restaurants, shopping, entertainment, and historic attractions in the nation's oldest city. Whether you're looking to build a primary residence, vacation getaway, or investment property, this lot offers the ideal opportunity to create your own slice of paradise near the shore. Don't miss your chance to own land in one of the area's most sought-after beachside communities with no HOA.

5306 Pelican Way, St. Augustine

Courtesy of PONTE VEDRA CLUB REALTY, INC.

Listing courtesy of PONTE VEDRA CLUB REALTY, INC..

Listing courtesy of ROBIN ARNOLD, PA from PONTE VEDRA CLUB REALTY, INC..

$995,000

261995 MLS

The beach lifestyle you’ve been dreaming of starts here. Build your custom coastal retreat on this newly available oversized homesite with potential ocean views in the desirable Anastasia Hills area of St. Augustine — just a short walk to the beach and breathtaking Atlantic sunrises. Enjoy the perfect blend of laid-back coastal living and vibrant local charm, with easy access to restaurants, shopping, entertainment, and historic attractions in the nation’s oldest city. Whether you’re looking to build a primary residence, vacation getaway, or investment property, this lot offers the ideal opportunity to create your own slice of paradise near the shore. Don’t miss your chance to own land in one of the area’s most sought-after beachside communities with no HOA.

5306 Pelican Way, St Augustine

Courtesy of Ponte Vedra Club Realty, Inc

$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.