Courtney Oaks Real Estate

Welcome to Courtney Oaks, a hidden gem nestled in the heart of St. Augustine, Florida. This charming subdivision offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and everyone in between. With its picturesque landscapes and beautifully designed homes, Courtney Oaks embodies the essence of Florida living.

As you stroll through the tree-lined streets of Courtney Oaks, you’ll be captivated by the warm community spirit and friendly neighbors. The subdivision features a variety of thoughtfully designed homes, ensuring that there’s something for everyone. Whether you’re seeking a cozy single-family residence or a spacious family home, you’ll find the perfect fit in this delightful community.

Location is key, and Courtney Oaks does not disappoint. Situated just minutes from the historic charm of downtown St. Augustine, residents can enjoy easy access to a wealth of dining, shopping, and entertainment options. Explore the rich history of the nation’s oldest city, visit stunning beaches, or indulge in the vibrant local arts scene—all just a short drive away.

For outdoor enthusiasts, Courtney Oaks is surrounded by lush parks and nature trails, providing ample opportunities for hiking, biking, and enjoying Florida’s natural beauty. The community is also conveniently located near top-rated schools and essential amenities, making it a desirable choice for families.

Discover the charm of Courtney Oaks, where community spirit meets the beauty of St. Augustine. Your dream home awaits in this idyllic subdivision!

Newest Listings in Courtney Oaks

$755,990

4 Beds ⋅ 3 Baths ⋅ 2150120 MLS

TO BE BUILT - build your dream home with Ashley Homes in the highly sought-after SilverLeaf community. Personalize one of our thoughtfully designed floorplans and select from a wide range of finishes and options to create a home that fits your lifestyle. Ashley Homes in Courtney Oaks includes an impressive lineup of upscale standard features, including smooth drywall finishes, 8' interior doors, 3 cm quartz countertops, 42'' cabinetry in multiple color selections, under-cabinet lighting, exterior vinyl soffit lighting, and more. Every home also includes a paver driveway, walkway, patio, and covered lanai for added curb appeal and outdoor living space. Located in a natural gas community, homes in SilverLeaf are equipped with a gas cooktop, tankless water heater, and both gas and electric dryer connections for convenience and efficiency.

156 Courtney Oaks Drive, St. Augustine

$929,000

5 Beds ⋅ 4 Baths ⋅ 2147260 MLS

Be in your brand new home for the holidays!! Custom floorplan design by Ashley Homes. Why have the same floorplan as others when you can have something totally unique?! We took our 2899 floorplan and created a stunning 2 story family room with an overlook from the bonus! If you take this home over early enough, you can still make design selections (some upgraded options already included in price!)

177 Pine Grove Point, St. Augustine

$1,054,500

4 Beds ⋅ 4 Baths ⋅ 2145011 MLS

Brand new home in Courtney Oaks at SilverLeaf. A coastal feel from the outside in to reflect a true Florida lifestyle. A courtyard 2 car garage and a single garage with a separate entry provides for gorgeous curb appeal and ample driveway space. Walking through the double door front entry, you are greeted by 11' ceilings and a flex room off the foyer- makes for a great home office. The family room features built ins with tons of cabinet and drawer storage. A gourmet open concept kitchen featuring white cabinets, quartz countertops, under cabinet lighting, and a vented hood to the outside is the perfect set up. Windows and a slider across the back of the house allow for an abundance of natural light. The owners suite is located on the first floor with a bay window and luxurious bathroom with a fully tiled walk in shower and a soaker tub, and a walk in closet the size of a bedroom! Upstairs includes a bonus room with a wet bar set up and 3 secondary bedrooms- all w/walk-in closets

268 Pine Grove Point, St. Augustine

$1,499,900

5 Beds ⋅ 5 Baths ⋅ 2141333 MLS

REDUCED $200,000! Our stunning Stella II model in Courtney Oaks-now for sale with a 90 day delayed close w/ NO leaseback. The home is situated on a large water to preserve view homesite. This home has it all, 4 bedrooms, 5 baths, insulated 3 car split garage, downstairs recreation room, upstairs bonus and loft, study and formal dining room. Every designer detail you could imagine including a spectacular lighting package and wood flooring. The entry is flanked with the dining & study, all have tray ceilings with tongue and groove inserts. A stunning water view from the front entry through the huge 16' slider. The gorgeous kitchen has a pot filler, large 36' gas range, Thermador refrigerator, double oven, wall microwave, farm sink, massive pantry AND butler's pantry and designer wood vent. The large mud bench is opposite the oversized laundry with ample cabinets, counter space and a sink. The owner suite with sitting room has a beautiful view and a spa bath with free standing tu The oversized pavered lanai includes a fireplace with room for a TV directly above. The huge upstairs bonus includes a wet bar, cabinets and under cabinet beverage center - all overlooking the water and preserve. The garage includes a golf cart charging circuit, perfect for getting to all of the SilverLeaf social events or the new amenities Now Open in Johns Island. The floor plan as built is in the documents. POOL CONCEPTUAL RENDERING ONLY Artist's illustration for marketing purposes. Not to scale. Subject to engineering, survey, permitting, HOA approval, zoning, setbacks, and all applicable governmental requirements. No representation or warranty is made that the improvements shown can be constructed as depicted.

37 Courtney Oaks Drive, St. Augustine

$1,025,000

4 Beds ⋅ 3 Baths ⋅ 2139711 MLS

Wake up to sunlight streaming through this like-new Mastercraft home in the gated Courtney Oaks in Silverleaf, where warmth and comfort greet you at every turn. Natural light dances across beautiful wood floors, highlighting an open floor plan designed for easy living and entertaining. The gourmet kitchen features quartz countertops, stainless appliances, a large island, butler's pantry, and spacious pantry for effortless organization. High ceilings enhance the airy feel, while the split bedroom layout and walk-in closets offer privacy and space. Step outside to a screened-in patio overlooking a heated saltwater pool and summer kitchen, perfect for year-round enjoyment. The expansive backyard invites play and relaxation. Located near the new amenity center and schools with easy commute access, this home blends style, function, and convenience into one exceptional opportunity. This house is meticulously maintatined waiting for its new owner!

140 Courtney Oaks Drive, St. Augustine

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The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Northeast Florida Multiple Listing Service, Inc. Real estate listings held by brokerage firms other than Realty Exchange LLC are marked with the listing broker’s name and detailed information about such listings includes the name of the listing brokers. Data provided is deemed reliable but is not guaranteed. © 2026 Northeast Florida Multiple Listing Service, Inc. All rights reserved. Data last updated