Trailmark Real Estate

Trailmark Real Estate

Welcome to Trailmark, a picturesque subdivision nestled in the heart of St. Augustine, Florida. This vibrant community offers a perfect blend of natural beauty and modern living, making it an ideal choice for families, retirees, and everyone in between.

Trailmark is designed with an emphasis on outdoor living and a healthy lifestyle. Spanning over 1,500 acres, the subdivision is bordered by lush conservation areas, providing residents with a serene backdrop of nature. With miles of scenic trails, residents can enjoy leisurely walks, biking, or jogging through the beautiful landscapes. The community also boasts an impressive array of amenities, including a sparkling resort-style pool, a state-of-the-art fitness center, and a playground for the little ones.

For those who appreciate a sense of community, Trailmark hosts various events throughout the year, fostering connections among neighbors and creating lasting friendships. From seasonal celebrations to family-friendly activities, there’s always something happening here.

Located just a short drive from historic downtown St. Augustine, residents can easily explore the unique charm of the nation’s oldest city. Enjoy world-class dining, shopping, and cultural experiences, all while being close to pristine beaches and scenic waterways.

With a range of beautiful homes to choose from, each thoughtfully designed to meet the needs of modern families, Trailmark is more than just a place to live; it’s a lifestyle. Discover the magic of Trailmark, where nature and community come together in perfect harmony. Your dream home awaits in this idyllic Florida paradise!

Newest Listings in Trailmark

$949,900
4 Beds ⋅ 3 Baths ⋅ 2156969 MLS
Welcome to 785 Back Creek Drive in TrailMark Estates. Located in the highly sought after ST. John's county. This one of a kind exceptional 2024 built home blends fresh, modern style with everyday comfort. This open and spacious 4-bedroom, 3-bath floor plan offers room to grow, gather, and unwind, all set in the secluded most desirable areas of TrailMark. Step inside to soaring 10-foot ceilings & 8-foot doors throughout creating a bright, airy feel from the moment you enter this beautifully modern home. With designer touches throughout this open concept living area flows effortlessly to the kitchen and dining spaces, perfect for entertaining or relaxed family nights. Thoughtful designer upgrades elevate the experience throughout, including the primary bathroom soaking in your own private retreat with a spa like vibe. Electric window treatments add modern convenience and comfort at the touch of a button, as well as Z-blinds and custom shutters. The primary suite is generously sized with refined finishes, while three additional bedrooms provide flexibility for guests, a home office, or playroom. A whole-home water softener adds comfort and convenience. As you walk through the home a resort-style oasis awaits around back with a luxurious modern style screened in pool featuring a waterfall and bubblers framed by stunning white limestone decking for a sleek modern finish. This 16x32 7-foot-deep breathtaking pool includes a Heatwave SuperQuiet IceBreaker AquaCal pool heater to extend your summer, a pool sync for easy mobile access and beautiful lighting making this a tranquil backyard retreat just waiting for you! The views of the wildlife that back up to this oasis is spectacular while also listening to early morning Lions roaring from the ST. Augustine Wild Reserve is amazing! Whether you're hosting summer get togethers or enjoying a quiet evening soak, this backyard is built for year-round enjoyment. The paver driveway leads to the epoxy coated garage floor, modern cabinets, a work bench and slat wall make this 3-car garage complete. This home is polished and move in ready. Perfectly positioned in TrailMark Estates, this nearly new home delivers upgraded living, beautiful design, and an unbeatable Florida lifestyle all in a top-rated St. Johns County school district. Come experience it for yourself! Seller Improvements: Pool & Screen $120,000.00; Shark Coated garage floor $3,000.00; Garage Cabinets & Slate Wall $9,000.00.

785 Back Creek Drive, St. Augustine
$589,900
4 Beds ⋅ 3 Baths ⋅ 2153167 MLS
Beautifully appointed Landon Homes residence in the highly desirable TrailMark community! Situated on a premium 70' preserve homesite, this home offers luxury, privacy, and convenience. Features include wood-look tile flooring, 8' doors, tray ceilings with crown molding, and a spacious open-concept layout. The gourmet kitchen boasts quartz countertops, 42'' cabinets, a gas cooktop, and double wall ovens. Relax on the oversized screened lanai overlooking the fully fenced backyard and private preserve with no rear neighbors. Additional highlights include a new roof (May 2024), 3-car garage with epoxy flooring, tankless gas water heater, and a floored, walkable attic with pull-down stairs offering exceptional storage. Walk to TrailMark's resort-style pool, fitness center, parks, playgrounds, walking and biking trails, and dog park. Seller offering up to $10,000 toward buyer's closing costs, prepaids, and/or an interest rate buy-down with an acceptable offer.

289 Weathered Edge Drive, St. Augustine
$474,990
4 Beds ⋅ 3 Baths ⋅ 2152008 MLS
Sample Images!!! Welcome to the pinnacle of luxury living in Trailmark's final phase. Introducing the Nassau Floor Plan - a masterpiece of design and craftsmanship. Exquisite Home Features: Impressive two-story layout Generous 1,968 sq ft of living space 4 spacious bedrooms 2.5 elegant bathrooms Convenient 2-car garage Breathtaking preserve views The Nassau embodies sophisticated living, meticulously crafted to cater to your every need. Each room is thoughtfully designed to maximize comfort and functionality, creating the perfect backdrop for your lifestyle. 3 roomy bedrooms and a Covered Lanai. Home is located in a gas community with Gas Cooktops, and gas tankless water heaters. 9' Ceilings on both levels. Trailmark is a beautiful, secluded community located in the growing area of St. Johns County. With impressive oak tree hammocks and winding nature trails.'' ''Ask about our limited-time builder incentives!''

722 Farmfield Drive, St. Augustine
$479,990
4 Beds ⋅ 3 Baths ⋅ 2152007 MLS
Sample Images!!! Welcome to the pinnacle of luxury living in Trailmark's final phase. Introducing the Nassau Floor Plan - a masterpiece of design and craftsmanship. Exquisite Home Features: Impressive two-story layout Generous 1,968 sq ft of living space 4 spacious bedrooms 2.5 elegant bathrooms Convenient 2-car garage Breathtaking preserve views The Nassau embodies sophisticated living, meticulously crafted to cater to your every need. Each room is thoughtfully designed to maximize comfort and functionality, creating the perfect backdrop for your lifestyle. 3 roomy bedrooms and a Covered Lanai. Home is located in a gas community with Gas Cooktops, and gas tankless water heaters. 9' Ceilings on both levels. Trailmark is a beautiful, secluded community located in the growing area of St. Johns County. With impressive oak tree hammocks and winding nature trails.'' ''Ask about our limited-time builder incentives!''

760 Farmfield Drive, St. Augustine
$499,990
4 Beds ⋅ 3 Baths ⋅ 2152006 MLS
The Stockton II is ready soon and offers a thoughtfully designed layout with the primary bedroom conveniently located on the first floor. This beautiful home features a gourmet kitchen. Wooden stair spindles add a stylish touch, while the upstairs layout offers 3 additional bedrooms, a full bath, and an amazing loft area that provides flexible living space. Situated on a desirable preserve lot, this home offers added privacy and a peaceful natural backdrop. Trailmark is a beautiful, secluded community in the growing St. Johns County area, known for impressive oak tree hammocks, winding nature trails, and architectural design inspired by Old Florida style. Conveniently located near I-95, highly regarded schools, and just a short drive to historic St. Augustine. Estimated completion is September. To gain entrance to this home and learn more about available buyer incentives, please visit the model center.

754 Farmfield Drive, St. Augustine
$499,990
5 Beds ⋅ 3 Baths ⋅ 2151998 MLS
The Vilano offers 2,500 square feet of thoughtfully designed living space with 5 bedrooms, 3 full bathrooms, and a versatile loft. This popular floor plan features an open-concept layout with ceramic tile throughout the main living areas and a spacious living room that flows to a covered patio with a beautiful pond view. The kitchen is both stylish and functional, showcasing a gas cooktop, eat-in island, and upgraded cabinetry. Wooden stair spindles add an elegant touch, while the upstairs laundry room is conveniently located near the bedrooms. The private primary suite offers a relaxing retreat with an en-suite bath. With spacious living areas, designer details, and a desirable pond view, the Vilano is a home you do not want to miss.

627 Farmfield Drive, St. Augustine
$799,000
6 Beds ⋅ 4 Baths ⋅ 2151573 MLS
WOW!! Seller offering $10,000 towards buyer's closing costs & prepaids or rate buy-down, with acceptable offer ! This beautifully crafted exceptional custom home by Landon Homes is situated on one of the most desirable lots in the neighborhood, open and spacious in the front with exceptional privacy in the rear. Thoughtfully designed with quality construction, timeless finishes, and superior craftsmanship, this home offers the perfect combination of luxury, comfort, and privacy. Inside, you'll find 10-foot ceilings, level 5 smooth wall finishes, crown molding throughout the main living areas, and an impressive 9-box coffered ceiling. The spacious kitchen features 42-inch solid full-overlap cabinetry, granite countertops, soft-close drawers, and abundant storage. A gas fireplace with custom mantel and granite hearth creates a stunning focal point, while surround sound speakers make entertaining effortless. The owner's suite offers a luxurious retreat with a 6-foot soaking tub and a convenient pass-through from the primary closet directly to the laundry room. Additional features include solid bamboo flooring in the office and living/dining areas, sound-deadening drywall throughout the home, an oversized two-car garage, and energy-efficient ZIP System construction. Step outside to your private backyard oasis featuring a heated saltwater pool, beautiful Shellock Luxury Pavers, and exceptional privacy, creating the perfect setting for year-round Florida living. For added peace of mind, this home has been extensively updated and meticulously maintained by the original owner. Recent improvements include a new driveway, walkway, landscaping, and exterior paint (2023), interior paint refresh (2026), brand-new carpet throughout (June 2026), new pool screens (2026), new pool pump (2026), A/C indoor unit and coil replacement (2025), and a new outdoor compressor (2026). With custom construction, high-end finishes, major system updates, and one of the best homesites in the community, this exceptional home is truly a rare find.

99 Weathered Edge Drive, St. Augustine
$479,999
4 Beds ⋅ 3 Baths ⋅ 2150834 MLS
SELLER OFFERING RATE BUYDOWN WITH ACCEPTABLE OFFER! HOME COMES WITH OVER $70,000 IN UPGRADES! Better than new!! Custom finishes include new luxury vinyl plank floors, plantation shutters, pavers in the backyard patio and driveway, and a built-in Sonos audio system that creates the perfect atmosphere for entertaining or relaxing at home. This home is over 2500 square feet with 4 bedrooms, 3 bathrooms in the highly sought-after TrailMark community. The stunning primary suite serves as a private retreat, featuring a beautifully upgraded spa-inspired shower and custom touches that make everyday living feel luxurious.. The heart of the home flows seamlessly into the outdoor living space, where an extended patio and fully fenced backyard provides the perfect setting for outdoor living. Trailmark amenities include resort-style pool, pickleball, fitness center, over 10 miles of walking trails and much more! Schedule a showing today!

165 Bluegrass Way, St. Augustine
$404,990
3 Beds ⋅ 3 Baths ⋅ 2149430 MLS
Nestled against a tranquil preserve in the sought-after TrailMark community, this light-filled, open-concept home perfectly blends modern comfort with peaceful living. The kitchen shines with granite countertops, gas range, upgraded refrigerator, and a large breakfast bar ideal for entertaining. Enjoy ultimate privacy with a first-floor owner's suite complete with a spacious ensuite bath. Upstairs, a versatile loft provides flexible bonus space, and every secondary bedroom boasts a walk-in closet. Live the indoor-outdoor lifestyle on the expansive covered patio, pre-plumbed with a gas stub for a future outdoor kitchen, while taking in serene & lush preserve views. Residents enjoy TrailMark's premier nature-inspired amenities, including a resort-style pool, fitness center, sports courts, and parks!

210 Wineberry Lane, St. Augustine
$665,000
4 Beds ⋅ 4 Baths ⋅ 2150408 MLS
Welcome to this exceptional MasterCraft-built Sebastian floorplan, perfectly positioned on a private preserve homesite within the highly desirable TrailMark community of St. Johns County. Thoughtfully designed and extensively upgraded, this impressive residence offers the ideal blend of elegance, comfort, functionality, and modern Florida living. From the moment you arrive, the home's curb appeal and attention to detail are immediately evident. Enhanced landscaping, front and rear gutters, and an oversized three-car garage create a polished first impression, while the serene preserve backdrop provides a sense of privacy and tranquility rarely found. Inside, soaring 10-foot ceilings, 9-foot doors, upgraded Craftsman trim, wrapped windows, solid-core interior doors, and beautiful 48-inch plank tile flooring establish a refined yet welcoming atmosphere throughout the home. Designed for both everyday living and effortless entertaining, the open-concept floorplan seamlessly connects the main living spaces while allowing natural light to fill every room. Additional recessed lighting and upgraded ceiling fans throughout the home enhance both comfort and ambiance, creating spaces that feel equally suited for quiet evenings at home or gatherings with family and friends. The kitchen serves as the centerpiece of the home and showcases a collection of premium finishes and thoughtful upgrades. Stunning Cambria quartz countertops, a large center island, stacked 42-inch cabinetry, and a striking full brick backsplash combine timeless design with exceptional functionality. Abundant storage and expansive workspace make meal preparation and entertaining a pleasure, while the oversized island naturally becomes the heart of conversation and connection. Adjacent to the kitchen, a custom pocket office provides a versatile workspace complete with upper and lower cabinetry and matching quartz countertops. Whether utilized as a home office, study area, household command center, or creative space, it offers convenience while remaining connected to the main living areas. The owner's suite is thoughtfully positioned to provide privacy and relaxation. Featuring an elegant tray ceiling and peaceful preserve views, the space offers a true retreat from the day. The luxurious owner's bath has been enhanced with upgraded cabinetry, Cambria quartz countertops, and a beautiful freestanding soaking tub, creating a spa-inspired setting designed for comfort and rejuvenation. Custom closet organizers maximize storage within the spacious walk-in closet, while a convenient pocket door provides direct access to the well-appointed laundry room. The laundry room has been thoughtfully upgraded with upper and lower cabinetry, quartz countertops, and a utility sink, adding both beauty and practicality to daily routines. One of the home's most appealing features is its remarkable flexibility. The original flex room and powder bath have been professionally transformed into a private bedroom suite complete with a large closet and full bath, creating an ideal space for guests, multigenerational living, or a private office. Upstairs, the expansive bonus room has been further enhanced with a full bathroom, large closet, and built-in queen Murphy bed, allowing the space to easily function as a guest retreat, media room, fitness area, playroom, or secondary living space. Throughout the home, every upgrade reflects a commitment to quality and craftsmanship. Upgraded lighting fixtures, ceiling fans in every bedroom, the bonus room, living room, and lanai, additional recessed lighting, custom trim work, solid-core doors, extensive quartz surfaces, and custom storage solutions contribute to the home's elevated character and enduring appeal. Outdoor living is equally impressive. The screened lanai overlooks the peaceful preserve, providing a private setting to relax, entertain, or simply enjoy Florida's year-round outdoor lifestyle. Surrounded by nature, the backyard offers a sense of serenity that enhances everyday living and creates a true extension of the home's interior spaces. The oversized three-car garage provides exceptional flexibility for vehicles, recreational equipment, hobbies, and storage. Added overhead metal storage racks maximize organization while maintaining ample usable space. Additional features include a whole-home water softener system, upgraded Craftsman trim package, wrapped windows throughout, front and rear gutters, screened lanai enclosure, custom closet systems, upgraded cabinetry, enhanced lighting package, and numerous builder and post-construction improvements that distinguish this home from others in the community. Beyond the home itself, TrailMark offers an unparalleled lifestyle centered around recreation, nature, and community. Residents enjoy access to a resort-style amenity center featuring a beach-entry pool, lap pool, fitness lawn, clubhouse, playgrounds, basketball courts, pickleball courts, sand volleyball courts, sports fields, scenic lakes, and miles of walking and biking trails that weave throughout the community's preserved natural landscape. The kayak launch provides direct access to Six Mile Creek, offering opportunities for kayaking, paddleboarding, fishing, and exploring Florida's natural beauty. Community events and gatherings throughout the year foster a welcoming environment where neighbors quickly become friends. Ideally located within St. Johns County, TrailMark offers convenient access to top-rated schools, shopping, dining, healthcare facilities, and major transportation corridors. Historic downtown St. Augustine, area beaches, Jacksonville, and numerous employment centers are all within easy reach, allowing residents to enjoy both a peaceful community setting and outstanding regional connectivity. This exceptional home represents a rare opportunity to own a thoughtfully upgraded residence that seamlessly combines luxury, versatility, privacy, and lifestyle. Meticulously maintained and beautifully appointed throughout, it offers the space, quality, and setting to enjoy for years to come. Experience the very best of TrailMark living and discover why this remarkable property feels so much like home.

159 Weathered Edge Drive, St. Augustine
$399,000
3 Beds ⋅ 2 Baths ⋅ 2149567 MLS
Nestled on a premium lot with neighboring homes on only one side for added privacy, this beautifully maintained 3-bedroom, 2-bath home in sought-after TrailMark offers the perfect combination of comfort, space, and community. Filled with natural light, the open and spacious floor plan is designed for both everyday living and entertaining. The kitchen serves as the heart of the home, featuring a large island with breakfast bar seating, stainless steel appliances, and ample storage while overlooking the dining area and spacious living room for effortless gathering and connection. The primary suite offers a peaceful retreat with walk-in closets and an ensuite bath featuring a dual-sink vanity and walk-in shower. Two additional bedrooms provide flexibility for guests, a home office, or hobbies and share a full bathroom. Outdoor living is just as inviting with a spacious screened lanai overlooking a fully fenced backyard--making it completely dog-friendly and ready for your furry family members--all while showcasing a beautiful, serene nature preserve view. It's the perfect backdrop for outdoor activities, watching your pets play, and enjoying relaxing evenings in total privacy. Additional highlights include a two-car garage and a prime location close to schools, shopping, dining, and everyday conveniences. TrailMark residents enjoy exceptional amenities including a clubhouse, pool, dog park, and playground. Whether you're enjoying the community amenities, relaxing in your private backyard with views of nature, or entertaining friends and guests, this home offers the lifestyle you've been looking for.

184 Wineberry Lane, St. Johns
$416,999
4 Beds ⋅ 2 Baths ⋅ 2148589 MLS
REMOTE WORKERS paradise! Bigger, with more rooms, and priced lower than many new builds, this nearly new 2023 home offers exceptional value without the uncertainty of future tax reassessments--property taxes have already been established. Owner upgrades include a water softener and stylish kitchen backsplash, making this home move-in ready. Featuring 4 bedrooms, 2 bathrooms, a dedicated office/flex space, and a 2-car garage overlooking a peaceful pond, this open-concept home provides plenty of room to live, work, and entertain. The kitchen showcases quartz countertops, 42-inch cabinets, stainless steel appliances, and ample gathering space. Located in TrailMark, residents enjoy over 10 miles of trails, resort and lap pools, fitness center, pickleball and basketball courts, playgrounds, dog park, kayak launch, and year-round community events. Zoned for top-rated St. Johns County schools with convenient access to Jacksonville and St. Augustine.

35 White Rabbit Run, St. Augustine
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