Trailmark Homes under $500,000

Trailmark Homes under $500,000

Welcome to Trailmark, a vibrant and inviting subdivision nestled in the heart of St. Augustine, Florida. Known for its picturesque landscapes and family-friendly atmosphere, Trailmark is the perfect blend of natural beauty and modern living. This charming community offers residents a unique opportunity to enjoy the serenity of nature while being just minutes away from the historic attractions and beautiful beaches that St. Augustine is famous for.

Trailmark boasts a variety of homes that cater to diverse lifestyles and budgets, with many options available for under $500,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find a range of thoughtfully designed floor plans that emphasize comfort and functionality. Each home is crafted with quality materials and features modern amenities, ensuring a delightful living experience.

One of the standout features of Trailmark is its commitment to outdoor living. The community is surrounded by lush conservation areas, scenic trails, and sparkling lakes, making it an ideal setting for nature enthusiasts. Residents can enjoy leisurely walks, biking, or simply soaking in the beautiful Florida sun. The community also includes a resort-style pool, playgrounds, and social spaces, fostering a strong sense of community and connection among neighbors.

With its affordable housing options, stunning natural surroundings, and proximity to the rich history of St. Augustine, Trailmark is more than just a neighborhood; it’s a place to call home. Come discover the charm and warmth of Trailmark, where your dream home awaits!

Newest Trailmark Homes under $500,000

257 Pepperpike Way, St. Augustine
$368,500
4 Beds ⋅ 2 Baths ⋅ 2167222 MLS
Energy efficient living meets everyday comfort in this beautiful St. Augustine home, enhanced with modern upgrades including a natural gas tankless water heater and solar panels for long term savings. Located in a quiet, established community, this property blends convenience, smart design, and sustainable features. Step inside to an inviting open concept layout filled with natural light and neutral finishes. The kitchen offers generous counter space, ample cabinetry, and a functional flow that keeps you connected while cooking. The spacious living and dining areas create a warm central hub ideal for gatherings or relaxed evenings at home. The split bedroom floor plan provides privacy for the owner's suite, complete with a walk in closet and well appointed bathroom. Additional bedrooms are versatile for guests, office space, or hobbies. Owned by the Secretary of the VA and sold as is. May qualify for Vendee(seller) financing.

257 Pepperpike Way, St. Augustine
52 Providence Drive, St. Augustine
$469,000
4 Beds ⋅ 3 Baths ⋅ 2166417 MLS
Coming Soon listing, no showings. Welcome home to this beautifully upgraded Destin floor plan in the sought-after TrailMark community! Offering 4 bedrooms, 3 baths and an oversized 3-car garage, this thoughtfully designed home on a .35 acre lot provides plenty of space to live and entertain. Natural light pours through large windows, highlighting the open layout, wood-look tile and tray ceilings throughout the main living areas. The gourmet kitchen is made for everyday living and entertaining with an oversized prep and breakfast island, generous counter space, double ovens, gas cooktop and sleek subway tile backsplash. The split-bedroom design creates a private primary retreat complete with a walk-in closet and spacious ensuite featuring a soaking tub and seamless glass shower. Out back, unwind on the screened patio overlooking the large fenced backyard with plenty of room to add a pool, create an outdoor entertaining space or simply enjoy the extra room to relax. TrailMark offers a sought-after St. Augustine lifestyle with resort-style amenities, including pools, a fitness center, sports courts, miles of trails, parks, and access to Six Mile Creek. Its desirable location pairs a beautifully planned community setting with convenient access to shopping, dining, top-rated St. Johns County schools, and the best of Northeast Florida!

52 Providence Drive, St. Augustine
324 Ferndale Way, St. Augustine
$499,000
4 Beds ⋅ 3 Baths ⋅ 2165573 MLS
ASSUMABLE LOAN!!!!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
214 Pepperpike 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
98 Ferndale Way, St. Augustine
$419,900
3 Beds ⋅ 2 Baths ⋅ 2160318 MLS
Welcome to this move-in ready 2020-built lakefront home in the highly desirable Trailmark subdivision of St. Augustine, FL! Featuring 3 bedrooms and 2 bathrooms, this beautifully upgraded home offers modern comfort, stylish finishes, peaceful lake views, and thoughtful details throughout. Step inside to high ceilings, luxury vinyl plank flooring throughout the main living areas, and neutral carpet in the bedrooms for added comfort. The open-concept layout is bright and inviting, with large clear sliding glass doors that showcase beautiful lake views from inside the home and create a seamless connection to the outdoor living spaces. The kitchen is a true standout with all-new stainless steel appliances, a gas range, gorgeous granite countertops, and a large kitchen island with bar seating--perfect for cooking, dining, entertaining, or gathering with family and friends. You'll also love the separate cabinet and coffee bar area, complete with an outlet for all your kitchen essentials, plus a great dedicated space for an electronic calendar, small TV, or command center. A walk-in pantry provides plenty of storage and convenience. The spacious primary bedroom features a beautiful accent wall and a large bay window that perfectly frames the peaceful lake view, creating a relaxing retreat at the end of the day. The primary bathroom offers two walk-in closets, a separate linen closet, a large walk-in shower, and beautiful new fixtures for a fresh, modern feel. Additional upgrades include a tankless water heater, water softener, and a designated drop zone just inside the garage entry--ideal for jackets, shoes, books, keys, pet accessories, and everyday essentials.Outside, enjoy the best of Florida coastal living with established young Queen Palms, front and back sprinklers, a screened porch, an additional open covered porch area, and an open brick-paver patio--perfect for grilling, relaxing by a firepit, or entertaining guests. The backyard is fenced with wrought iron fencing and multiple gates, allowing you to enjoy the beautiful open lake views while helping keep your little ones and pets safely contained. The spacious 2-car garage provides plenty of room for parking and storage, while the ample driveway offers convenient additional parking for guests. Trailmark offers a multitude of impressive neighborhood amenities, all for a very low annual HOA fee! Residents enjoy an expansive resort-style pool, lap pool, Camp House, fitness center, sand volleyball, basketball and pickleball courts, playground, kayak launch, dog park, and scenic walking trails--creating the perfect blend of recreation, relaxation, and community living. With its lakefront setting, newer construction, upgraded features, outdoor living spaces, exceptional neighborhood amenities, and ideal location in Trailmark, this home is ready for you to move right in and enjoy the best of St. Augustine living.

98 Ferndale Way, St. Augustine
722 Farmfield Drive, St. Augustine
$439,990
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
210 Wineberry Lane, St. Augustine
$404,990
3 Beds ⋅ 3 Baths ⋅ 2149430 MLS
PROTECTED PRIVATE PRESERVE * 1ST FLOOR PRIMARY SUITE * WALK-IN CLOSETS IN EVERY BEDROOM Tucked against a protected preserve, this TrailMark home offers peaceful privacy and serene backyard views. Abundant natural light fills the open-concept living spaces, creating a bright, inviting atmosphere. The spacious kitchen features granite countertops, gas range, modern Samsung refrigerator, pendant lighting, and a large breakfast bar, perfect for entertaining. The private 1st floor primary suite includes a generous ensuite bath and walk-in closet. Upstairs, a versatile LOFT complements two spacious bedrooms, each with a walk-in closet, plus a large laundry room with gas dryer connection. Step outside & unwind on the covered patio, a welcoming space for relaxed gatherings & outdoor entertaining, w/ gas stub ready for a future outdoor kitchen. TrailMark residents enjoy resort-style amenities: pool, fitness center, sports courts, dog parks, playgrounds, walking trails, and a kayak launch

210 Wineberry Lane, St. Augustine
400 Weathered Edge Drive, St. Augustine
$469,900
4 Beds ⋅ 3 Baths ⋅ 2137488 MLS
Let's make a deal! Bring an offer let's chat about closing costs and rate buy downs. So many UPGRADES! Near the AMENITIES. Don't miss your chance to snag this home! Welcome to this beautifully maintained 4-bedroom, 3-bath home in a sought-after community, where comfort, style, and opulence come together. Recent updates include a new roof, Paid off SOLAR, widened driveway and pathway, enhancing both convenience and curb appeal. Inside, a light-filled interior showcases crisp white and neutral tones paired with pristine LVP flooring. The open floor plan flows seamlessly, perfect for everyday living and entertaining. The kitchen features granite countertops, a sleek backsplash, new refrigerator, and a large island ideal for prep or casual dining, while the living area offers built-in surround sound. Upstairs tinted windows add comfort and efficiency. Outside, enjoy a spacious, fully FENCED backyard with room to relax, play, or design your dream outdoor space. Located near I-95 with easy access to the river and ocean, and a community offering pools, kayak launch, fishing lake, dog park, scenic trails, and more-this home truly captures the Florida lifestyle

400 Weathered Edge Drive, St. Augustine
350 Wrensong Place, St. Augustine
$489,997
4 Beds ⋅ 3 Baths ⋅ 2124894 MLS
Welcome to this desirable Agate home, ready for quick move-in! Included features: a charming covered entry, a well-planned kitchen offering a center island and a built-in pantry, open dining and great rooms, a secluded primary suite showcasing a generous walk-in closet and a private bath, three secondary bedrooms, two additional bathrooms, a central laundry, and an inviting covered patio. This home also boasts white cabinetry throughout. SAMPLE PHOTOS, actual homes as constructed may not contain the features and layouts depicted and may vary from image(s).

350 Wrensong Place, St. Augustine
341 Wrensong Place, St. Augustine
$431,997
3 Beds ⋅ 3 Baths ⋅ 2110470 MLS
Ideal for entertaining, the Fraser's open-concept layout features a large kitchen with a breakfast-bar island, flanked by a separate dining area and a great room with access to an inviting covered patio. You'll also enjoy the convenience of a laundry room, plus a mudroom. Two secondary bedrooms share access to a full hall bath, and a secluded primary suite boasts a walk-in closet and private bath. SAMPLE PHOTOS, actual homes as constructed may not contain the features and layouts depicted and may vary from image(s).

341 Wrensong Place, St. Augustine
338 Wrensong Place, St. Augustine
$491,997
4 Beds ⋅ 3 Baths ⋅ 2098878 MLS
The thoughtfully designed Slate floor plan opens with two bedrooms flanking a bath. Further down the foyer, you'll find an open layout with a dining nook, a great room with access to the covered patio, and a kitchen with a center island. The primary suite is adjacent, and offers a generous walk-in closet and a private bath with a shower and a separate soaking tub. A fourth bedroom and a laundry complete the home. SAMPLE PHOTOS, actual homes as constructed may not contain the features and layouts depicted and may vary from image(s).

338 Wrensong Place, St. Augustine
326 Wrensong Place, St. Augustine
$484,997
4 Beds ⋅ 3 Baths ⋅ 2098848 MLS
Welcome to this desirable Agate home, ready for quick move-in! Included features: a charming covered entry, a well-planned kitchen offering a center island and a built-in pantry, open dining and great rooms, a secluded primary suite showcasing a generous walk-in closet and a private bath, three secondary bedrooms, two additional bathrooms, a central laundry, and an inviting covered patio. This home also boasts white cabinetry throughout. SAMPLE PHOTOS, actual homes as constructed may not contain the features and layouts depicted and may vary from image(s).

326 Wrensong Place, St. Augustine
Start Your Search
© 2026 Northeast Florida Multiple Listing Service, Inc. All rights reserved. This data is up-to-date as of . For the most current information, contact Gail DeMarco.