Trailmark Homes with Pond Waterfront

Welcome to Trailmark, a hidden gem nestled in the picturesque city of St. Augustine, Florida. This charming subdivision offers a perfect blend of nature, community, and modern living, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle.

Trailmark is renowned for its enchanting landscapes and lush greenery, providing a tranquil escape from the hustle and bustle of everyday life. As you explore the community, you’ll find beautifully designed homes that boast stunning pond waterfront views, allowing residents to bask in the beauty of Florida’s natural surroundings. Imagine waking up each morning to the gentle sounds of water lapping against the shore and the sight of vibrant sunsets reflecting on the surface of the pond.

The homes in Trailmark are thoughtfully crafted with modern amenities and spacious layouts, catering to a variety of lifestyles. With a strong emphasis on community, residents enjoy access to a wealth of recreational activities, including scenic walking trails, parks, and a community pool. The subdivision is also conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone’s throw away.

Whether you’re looking for a peaceful retreat or an active lifestyle, Trailmark offers a unique opportunity to experience the best of St. Augustine living. With its enchanting pond waterfront homes and a warm, welcoming community, Trailmark is not just a place to live—it’s a place to thrive. Come and discover your dream home in this idyllic setting today!

Newest Trailmark Homes with Pond Waterfront

$509,990

2 Beds ⋅ 2 Baths ⋅ 2166164 MLS

Welcome to Reverie at TrailMark! Enjoy low-maintenance, resort-style living in this beautifully upgraded Edison floor plan, featuring 1,812 sq ft, 2 bedrooms, 2 bathrooms, a flex room, and a 2-car garage on a large pond-front lot with a beautiful view. This home is loaded with upgrades including 10' ceilings, tray ceilings in the primary suite and great room, floor-to-ceiling shower tile, 4' extended garage, fenced yard, screened lanai, updated pantry, built-in great room TV wall, finished garage floor, 240V garage receptacle, water softener, window treatments, full irrigation, and upgraded lighting. Reverie is a gated community with a clubhouse, fitness center, heated resort pool & spa, pickleball, bocce ball, dog park, walking trails, biergarten, canoe launch, and plenty of social activities. This home is conveniently located within walking/golf-cart distance of community amenities. Located in the highly desirable World Golf Village area, you're minutes from Publix, Costco, Home Depot, restaurants, shopping, healthcare, I-95, historic St. Augustine, and Northeast Florida beaches. Beautifully upgraded, pond-front, and move-in ready—enjoy the TrailMark lifestyle! Some photos have been virtually rendered.

155 Blackbird Lane, St. Augustine

$507,000

4 Beds ⋅ 3 Baths ⋅ 2165573 MLS

Paver patio, gas fire pit, new air conditioner, and fully fenced-in yard highlight this stunning 4-bedroom, 3-bath Dream Finders Vilano model, ideally positioned toward the front of highly sought-after TrailMark. Waterfront living meets modern luxury with beautiful water views, no home directly behind the property, and a desirable combination of privacy, open views, everyday convenience, and relaxed Florida living. Step inside to a thoughtfully designed two-story floor plan featuring luxury finishes throughout, including tile and luxury vinyl plank flooring in the main living areas, a first-floor bedroom and full bathroom, and spacious living areas designed for both everyday living and entertaining. At the heart of the home is the gourmet kitchen, featuring elegant quartz countertops, ample cabinetry, a large walk-in pantry, upgraded kitchen faucet, and newer dishwasher. The open-concept layout flows seamlessly into the dining and living spaces, creating the perfect setting for gathering with family and friends. The home has been thoughtfully updated with numerous recent improvements, including a new air-conditioning system, new flooring in the downstairs bedroom, new carpeting on the stairs, and upgraded hardware throughout. The primary bathroom features a new shower floor, upgraded faucets, and upgraded lighting, while the additional bathroom also features upgraded faucets. Upstairs, you'll find additional bedrooms and flexible living space, offering plenty of room for guests, a home office, or a bonus area. The spacious primary suite provides a peaceful retreat with beautiful finishes and a comfortable layout. Step outside to the fully fenced backyard and enjoy the best of outdoor Florida living. A gorgeous paver patio and gas fire pit create an inviting space for entertaining, relaxing, or enjoying the peaceful waterfront setting. As evening approaches, stunning sunsets over the water provide a beautiful backdrop to enjoy year-round. TrailMark residents enjoy an incredible resort-style lifestyle with amenities including a luxurious pool, fitness center, playground, kayak launch, scenic trails, and beautiful natural spaces. With its desirable location toward the front of the neighborhood, waterfront setting, modern finishes, extensive recent updates, flexible floor plan, gorgeous outdoor retreat, stunning sunset views, and exceptional community amenities, this Dream Finders Vilano model is a true TrailMark gem

324 Ferndale Way, St. Augustine

$435,000

4 Beds ⋅ 3 Baths ⋅ 2165053 MLS

If you've been craving space and serenity, this is it. In Trailmark, this home delivers a bright open layout, stunning pond & preserve views, and an unforgettable fully opening wall of sliding glass doors (4-panel sliding doors) that creates true indoor/outdoor living. Enjoy sunrise mornings, peaceful afternoons, and sunsets over the water. Featuring 4 bedrooms, 3 bathrooms, plus a flex room (no door/closet) ideal for an office, playroom, gym, or hobby space. In-ceiling surround sound makes game days and movie nights next level! Updated with roof & HVAC (2022), pool-ready fence & upgraded fans (2022), plus whole-home water purification (2023). Trailmark offers a resort lifestyle with 10+ miles of trails, resort-style pool + lap pool, fitness center, pickleball, basketball courts, playgrounds, lakeside pavilion, community events, dog park, and a kayak launch on Six Mile Creek, all in top-rated St. Johns County schools, minutes to I-95, historic St. Augustine & beaches!

214 Pepperpike Way, St. Augustine

$750,000

5 Beds ⋅ 4 Baths ⋅ 2162665 MLS

Welcome home to this meticulously cared-for, one-owner home that offers room for everyone with five true bedrooms, a flex space, and a loft! In Trailmark, where peaceful surroundings and the St. Johns County lifestyle meet, this home is overlooking a preserve and pond with a fully fenced backyard. Hardwood floors and crown molding flow downstairs. The kitchen features granite countertops, stainless appliances, double ovens, and a butler's pantry. The downstairs bedroom with a true en-suite bath is perfect for guests or multigenerational living, while an additional downstairs bath offers easy access to the backyard. The primary suite has a tray ceiling, gorgeous views, separate closets, upgraded countertops, a soaking tub, and separate shower. A three-car garage, reverse osmosis system, and water softener are additional perks. Enjoy Trailmark's incredible amenities, including a community pool, dog park, kayak launch, nature trails, and athletic fields. Schedule your private tour!

52 Crosswood Court, St. Augustine

Start Your Search

MFR MLS is the source of this information via Internet Data Exchange Program. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale. Availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase. All other use is strictly prohibited and may violate relevant federal and state law. Data last updated on

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