Wingfield Glen Real Estate

Welcome to Wingfield Glen, a hidden gem nestled in the heart of St. Augustine, Florida. This charming subdivision offers a perfect blend of serene living and modern convenience, making it an ideal destination for families, retirees, and anyone seeking a tranquil escape with easy access to the vibrant culture of St. Augustine.

Wingfield Glen is characterized by its picturesque tree-lined streets and beautifully designed homes, each exuding a unique charm that reflects the coastal lifestyle of Florida. Residents enjoy spacious lots and thoughtfully landscaped yards, providing ample space for outdoor activities and family gatherings. The community fosters a friendly atmosphere, where neighbors become friends, and every day feels like a vacation.

One of the standout features of Wingfield Glen is its proximity to some of the best attractions that St. Augustine has to offer. Just a short drive away, you can explore the historic downtown area, home to cobblestone streets, quaint shops, and renowned restaurants. For those who appreciate the great outdoors, the stunning beaches of Anastasia State Park and the scenic trails of the St. Johns River are within easy reach, perfect for weekend adventures or peaceful strolls.

Families will appreciate the highly-rated schools in the area, as well as the numerous parks and recreational facilities that cater to all ages. With a strong sense of community and a prime location, Wingfield Glen is more than just a place to live; it’s a lifestyle choice that embodies the essence of Florida living. Come discover your dream home in Wingfield Glen, where comfort meets convenience in the beautiful city of St. Augustine!

Newest Listings in Wingfield Glen

$747,000

5 Beds ⋅ 4 Baths ⋅ 2158457 MLS

Welcome to this beautifully reimagined two-story residence, where high-end craftsmanship meets serene natural surroundings - perfectly sited on a peaceful pond backing to a protected preserve, with no rear neighbors, ever. This 2,996 sq ft home offers 5 bedrooms and 4 bathrooms of thoughtfully renovated living space. Step inside to a light-filled, open-concept layout anchored by a show-stopping bookmatched porcelain fireplace, a true centerpiece for the main living area. The kitchen is equally striking, showcasing custom cabinetry, brand new appliances and premium designer finishes - ideal for everyday living and entertaining. The spacious primary suite offers a private retreat, while four additional bedrooms provide flexibility for family or guests. A 3-car garage and expansive backyard overlooking the water complete this rare offering. Roof is just 3 years old; HVAC 2018. A fully renovated, high-end home in a scenic, preserve-backed setting - schedule your private showing toda

745 New Wales Lane, St. Augustine

$499,000

4 Beds ⋅ 2 Baths ⋅ 2154415 MLS

Open House 8/9/26, 11-1! Clear your calendar & tour this move-in-ready home nestled on a quiet cul-de-sac in a desirable neighborhood! Offering an appealing split-bedroom floor plan, designer touches including board & batten accents, & a spacious 3-car garage. Just imagine cooling off in your sparkling pool & entertaining in your updated kitchen with brand-new stainless steel appliances & granite countertops. The owner's suite is a true retreat, complete with a tray ceiling, two generous walk-in closets, & a luxurious ensuite bath featuring dual granite vanities, a relaxing garden tub, & a separate shower. The office/flex room could be a potential 5th bedroom & the new AC & newer roof also give peace of mind. Located in the highly acclaimed St. Johns Co. school district, this exceptional home also offers convenient access to I-95, State Road 9B, & shopping/dining destinations in the Durbin & Beachwalk areas. Come see... it's ready for you to move in & make memories!

817 Esquire Lane, St. Augustine

$565,000

5 Beds ⋅ 2 Baths ⋅ 2151600 MLS

Welcome home to this exceptional 5-bedroom residence tucked away on a quiet cul-de-sac in the highly desirable Wingfield Glen community. Perfectly positioned on a spacious 0.30-acre homesite, this property offers privacy and tranquility with beautiful natural preserve views. Enjoy Florida living at its finest in the screened-in pool area, ideal for entertaining, relaxing, and creating lasting family memories. Designed with both comfort and practicality in mind, this home features a generous 3-car garage and an oversized driveway with parking for up to six vehicles--perfect for guests, growing families, or hobbyists. Inside, gather around the cozy fireplace that serves as the heart of the home and creates a warm, inviting atmosphere year-round. Major updates provide peace of mind, with a newer HVAC system plus a roof and hot water heater that are four years old or newer. Combining space, functionality, and a prime location, this special home is ready to welcome its next family.

756 New Wales Lane, St. Augustine

$475,000

4 Beds ⋅ 3 Baths ⋅ 2148644 MLS

PRICE REDUCED! This stunning 2,895sq ft residence offers the perfect blend of comfort, style, and functionality. Situated on a desirable corner lot with a fully fenced backyard, it provides both privacy and room to play, entertain, or unwind. Step inside to find formal living and dining rooms ideal for gatherings, along with a bright eat in kitchen that flows seamlessly into the cozy family room with a gas log fireplace. A versatile flex space/office adds even more convenience--perfect for remote work, hobbies, or a quiet retreat. The Owner's Suite is a true sanctuary, featuring a beautiful tray ceiling and a spa like bathroom designed for relaxation. Three additional bedrooms offer generous space for family or guests. Major updates bring peace of mind, including a roof & HVAC system that are only two years old. The exterior of this home has also been refreshed with new paint. This thoughtful layout, modern updates, and prime location, this home is ready to welcome its new owners

164 Prince Phillip 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