Trailside Homes for Sale

Trailside Homes for Sale

Welcome to Trailside, a picturesque subdivision nestled in the heart of Stuart, Florida, in the beautiful Martin County. This charming community offers a serene escape from the hustle and bustle of everyday life, while still being conveniently located near all the amenities you could desire. With its lush landscapes and friendly atmosphere, Trailside is the perfect place to call home.

Homes for sale in Trailside showcase a variety of architectural styles, catering to diverse tastes and preferences. Whether you’re seeking a cozy single-family home or a spacious property perfect for entertaining, you’ll find options that fit your lifestyle. Each residence is designed with comfort and functionality in mind, featuring modern amenities, open floor plans, and private outdoor spaces that invite you to enjoy the year-round Florida sunshine.

The community of Trailside is renowned for its family-friendly environment, with nearby parks, top-rated schools, and recreational facilities that cater to all ages. Residents can enjoy leisurely strolls along scenic walking paths, take advantage of the nearby waterways for boating and fishing, or simply relax in the tranquil surroundings.

With its prime location in Stuart, you’re just a short drive away from stunning beaches, vibrant shopping districts, and a plethora of dining options that showcase the best of Florida's coastal cuisine. If you're looking for a place that combines the charm of suburban living with the excitement of coastal life, Trailside is where your dream home awaits. Explore the homes for sale today and discover the perfect fit for your future!

Newest Trailside Homes for Sale

$5,995,000
7 Beds ⋅ 8 Baths ⋅ B26036047 MLS ⋅ Trailside BLDG.
Tucked behind the gates of an exclusive equestrian community, this extraordinary custom estate offers a rare blend of luxury, privacy, and acreage. Built in 2020 and set on 35 fully fenced acres, the property features over 7,500 square feet of living space with 7 bedrooms, 7.5 baths, impact glass, an elevator, and exceptional craftsmanship throughout. Designed for both everyday living and grand-scale entertaining, the home showcases a chef's island kitchen, expansive living areas, formal dining room, game room, and private den/safe room. The luxurious primary suite offers a gas fireplace and tranquil views across the estate. Outside, a resort-inspired setting awaits with a spectacular tiki pavilion, summer kitchen, heated pool and spa, four screened porches, and beautifully landscaped grounds complete with extensive lighting, a pond, fountain, and private dock. A substantial CBS utility building provides exceptional storage and workshop space, while the split four-plus-car garage, whole-house generator, and prime location near Stuart, Jupiter, shopping, and major highways complete this remarkable offering. A private retreat where luxury, land, and lifestyle come together on an impressive scale.

2985 SW Trailside Path, Stuart
$6,200,000
3 Beds ⋅ 4 Baths ⋅ R11160364 MLS
Private Gated Luxury Equestrian Estate West of Hobe Sound. Minutes to beaches, dining, shopping, I-95, Apogee Golf Club, Atlantic Fields, and The Ranch. Trailside Community is gated and features PVC white fencing for every estate throughout. This estate welcomes you with an Oak-lined long driveway with modern teak gates, keypad entry and scenic views in every direction. This modern farmhouse features a total of 3 Bedrooms, 3.5 baths with open floor plan, gourmet kitchen, gas range, walk-in pantry, bar area, dining room, sitting room, gym with steam shower, outdoor shower, walk-in primary closet, large primary bath, two patios off main living area, all-glass modern living room, and expansive outdoor entertaining areas. Resort-style outdoor amenities include 30x60 pool with built-in bench, fire pit, gas lanterns, pizza oven, brand-new grill, Green Egg, and 500-gallon propane smoker. Exceptional equestrian facilities: regulation irrigated dressage arena with premium footing and drainage, observation area; covered extra-large round pen with synthetic footing and irrigation; fenced bridle and walking path around entire property; large grassy paddocks and fields. CBS construction Barns with Eight 15x15 stalls, Big Ass Fans, fly system, hurricane rolldown shutters, fire system, rubber aisleways, 2 wash/grooming stalls, tack room, feed room, hay room, garden area, and groom apartment with full kitchen. Additional features: regulation Bermuda grass croquet court, clean pond with fountain, fenced dog area, whole-farm 60KW generator, RO pumphouse with thousand-gallon water tanks, large circular porte-cochere driveway with guest parking, separate employee entrance and parking, covered equipment area, fuel tank, multiple storage sheds, and extra-large CBS garage suitable for car/boat/RV storage with living area and gym. A rare turnkey offering combining luxury living and professional equestrian infrastructure.

2541 SW Trailside Path, Stuart
$2,500,000
2 Beds ⋅ 2 Baths ⋅ R11125709 MLS ⋅ Trailside BLDG.
Positioned on 21.59 acres between Jupiter and Hobe Sound within the gated 41-parcel equestrian community of Trailside, this property offers a rare opportunity in an area where large acreage is increasingly limited. Trailside is known for its private, peaceful setting, spacious 20-30 acre parcels, and access to nearby riding and nature trails—all within a short drive to beaches, golf, and conveniences. Currently configured as a turnkey equestrian property, the property includes over 7,000 sqft of 2020-built CBS construction, featuring a well-equipped 13-stall center-aisle barn and two-story living quarters. A designated homesite with underground power allows for a future main residence, while existing improvements, including reverse osmosis to the home and paddocks, a generator, and quality infrastructure, support immediate use as a private retreat or working equestrian estate. The grounds are fully fenced and cross-fenced with multiple paddocks, a lit arena, round pen, and a mile-long riding trail. The surrounding area continues to see growth with new luxury golf courses and private club communities, while remaining nearby to Jupiter and Hobe Sound.

2986 SW Trailside Path, Stuart
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