Trailmark Homes under $500,000

Welcome to Trailmark, a picturesque subdivision nestled in the heart of St. Johns County, Florida. This charming community offers a perfect blend of serene natural beauty and modern conveniences, making it an ideal place to call home. With its lush landscapes and scenic trails, Trailmark is designed for those who appreciate the great outdoors, featuring miles of walking and biking paths that meander through the stunning surroundings.

Trailmark is not just about beautiful scenery; it’s also about community. Residents enjoy a vibrant lifestyle with access to a variety of amenities, including a resort-style pool, a state-of-the-art fitness center, and a welcoming clubhouse that hosts numerous social events throughout the year. Families will appreciate the nearby top-rated schools and recreational facilities, ensuring that everyone has access to an enriching environment.

For those seeking affordable housing options, Trailmark offers an impressive selection of homes priced under $500,000. These beautifully designed residences combine modern architecture with functional living spaces, perfect for first-time buyers, families, or anyone looking to downsize without sacrificing quality. With a range of floor plans and styles available, you’re sure to find a home that fits your lifestyle and budget.

Living in Trailmark means embracing a community that values connection, nature, and quality living. Whether you’re exploring the nearby parks, enjoying a sunny day by the pool, or simply relaxing in your own backyard, Trailmark is a place where memories are made, and life is cherished. Come discover your dream home in this delightful subdivision today!

Newest Trailmark Homes under $500,000

$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

Courtesy of DOCTORS LAKE REALTY

Listing courtesy of DOCTORS LAKE REALTY.

Listing courtesy of MARK COLE, PA from DOCTORS LAKE REALTY.

$385,000

3 Beds ⋅ 2 Baths ⋅ 264268 MLS

Welcome home to 189 Foxcross Avenue in the sought-after TrailMark community! This beautifully maintained 3-bedroom, 2-bath home offers an inviting open-concept design perfect for everyday living and entertaining. The spacious kitchen is the heart of the home, featuring rich cabinetry, quartz-style countertops, stainless steel appliances, natural gas cooking, pendant lighting and a large center island with seating. The kitchen flows seamlessly into the living area, where wood-look flooring and a dramatic accent wall create a warm, contemporary feel. The spacious primary suite features abundant natural light, a walk-in closet and private bath with dual vanities and an oversized tiled walk-in shower. Two additional bedrooms offer plenty of flexibility for family, guests or a home office.

189 Foxcross Ave, St Augustine

Courtesy of Great Expectations Realty

$489,000

3 Beds ⋅ 2 Baths ⋅ 264202 MLS

Welcome to this beautiful 3-bedroom, 2.5-bath home in the highly desirable TrailMark community! Situated on a spacious corner lot, this home offers a fantastic open floor plan designed for both everyday living and entertaining. The bright, open kitchen features white cabinetry, granite countertops, stainless steel appliances, and a huge walk-in pantry with plenty of storage. Step outside to the oversized, fully fenced backyard with peaceful pond views and plenty of room to create your dream outdoor space or add a pool. Upstairs, you'll find a versatile sitting/loft area, conveniently located laundry room, and a spacious primary suite featuring a large walk-in closet and ensuite bath with dual vanities, a walk-in shower, and separate tub.

20 Bird Watch Ct, St Augustine

Courtesy of Lighthouse Realty Associates

$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

Courtesy of PONTE VEDRA CLUB REALTY, INC.

Listing courtesy of PONTE VEDRA CLUB REALTY, INC..

Listing courtesy of JESSICA SWEARINGEN from PONTE VEDRA CLUB REALTY, INC..

$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

Courtesy of MOMENTUM REALTY

Listing courtesy of MOMENTUM REALTY.

Listing courtesy of ALEXANDER NORKUS from MOMENTUM REALTY.

$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

Courtesy of SELLSTATE NEXT GENERATION REALTY

Listing courtesy of SELLSTATE NEXT GENERATION REALTY.

Listing courtesy of KIMBERLY T MORRIS from SELLSTATE NEXT GENERATION REALTY.

$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

Courtesy of OLYMPUS EXECUTIVE REALTY, INC

Listing courtesy of OLYMPUS EXECUTIVE REALTY, INC.

Listing courtesy of NANCY PRUITT from OLYMPUS EXECUTIVE REALTY, INC.

$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

Courtesy of REAL BROKER LLC

Listing courtesy of REAL BROKER LLC.

Listing courtesy of SHERI LYNN LIVENGOOD from REAL BROKER LLC.

$479,990

4 Beds ⋅ 3 Baths ⋅ 2146990 MLS

652 Farmfield Drive, St. Augustine

Courtesy of OLYMPUS EXECUTIVE REALTY, INC

Listing courtesy of OLYMPUS EXECUTIVE REALTY, INC.

Listing courtesy of NANCY PRUITT from OLYMPUS EXECUTIVE REALTY, INC.

$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

Courtesy of REAL BROKER LLC

Listing courtesy of REAL BROKER LLC.

Listing courtesy of MACHELL KLEE from REAL BROKER LLC.

$430,000

4 Beds ⋅ 3 Baths ⋅ 261479 MLS

MOVE-IN READY!!! Located in the desirable Trailmark Community, this beautiful home features a bright, open modern layout with stunning pond views. The spacious 4-bedroom, 3-bathroom split floor plan thoughtfully separates the luxurious owner's suite from the secondary bedrooms. Daily life centers around a grand Great Room, where triple sliding glass doors open directly onto a screened lanai with peaceful water views. The gourmet kitchen shines with white quartz countertops, 42-inch white cabinetry, a generous center island, a corner pantry, and premium stainless-steel appliances, including a gas range. Upgrades abound throughout the home, featuring durable ceramic wood-look tile in all main living areas, a pavered driveway, a pre-wired security system, and a gas tankless water heater for maximum energy savings. Additionally, a dedicated fourth bedroom suite with its own private bath offers the perfect flexible space for guests, an in-law suite, or a home office.

210 White Rabbit Run, St Augustine

Courtesy of Century 21 St Augustine Properties

$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

Courtesy of AXEN REALTY LLC

Listing courtesy of AXEN REALTY LLC.

Listing courtesy of STEPHANIE MORALES LLC from AXEN REALTY LLC.

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.