Trailside Real Estate

Trailside Real Estate

Welcome to Trailside, a picturesque subdivision nestled in the heart of the United States, where the beauty of nature meets the convenience of modern living. This charming community is designed for those who appreciate a serene environment while still being close to urban amenities.

Trailside is known for its lush landscapes, scenic walking trails, and family-friendly atmosphere. With tree-lined streets and well-maintained parks, residents are encouraged to embrace the great outdoors, whether it’s taking a leisurely stroll, biking with friends, or enjoying a picnic with loved ones. The community is thoughtfully designed, featuring a variety of home styles that cater to diverse tastes and lifestyles, from cozy single-family homes to spacious townhouses.

One of the standout features of Trailside is its commitment to fostering a sense of community. Regular neighborhood events, such as summer barbecues and holiday celebrations, create opportunities for residents to connect and build lasting friendships. Families will also appreciate the highly-rated schools in the area, ensuring that children receive an excellent education just a stone's throw from home.

Conveniently located near shopping centers, dining options, and recreational facilities, Trailside offers the perfect balance of tranquility and accessibility. Whether you’re looking for an active lifestyle or a peaceful retreat, this subdivision has something for everyone. Come explore Trailside, where your dream home awaits amidst a vibrant community that feels like family. Discover the lifestyle you’ve been searching for, and make Trailside your new home!

Newest Listings in Trailside

$539,990
3 Beds ⋅ 2 Baths ⋅ VALO2128636 MLS
Welcome to **45428 Oak Trail Square**—a beautifully updated three-level townhome nestled in the highly desirable Trailside community of Sterling. This move-in-ready home seamlessly blends modern upgrades with a versatile floor plan designed for today's lifestyle. ******First level - luxury vinyl plank flooring, fresh paint, updated lighting fixtures, and plush carpeting in select areas, creating a warm and inviting atmosphere throughout. The well-appointed kitchen features stainless steel appliances, ample cabinetry.****** Major system updates provide added peace of mind, including a **new roof (2025)**, **HVAC system (2020)**, and **water heater (2020) *****The second level offers a spacious bedroom with a **beautifully remodeled full bath (2025)**, along with a generous flex space featuring a cozy fireplace—ideal as a family room, home office, media room, or play area. *****The third level features two additional spacious bedrooms, including the primary suite with walk-in closets and a **stunning remodeled bath (2025)** complete with a soaking tub and separate shower. ****This home is perfectly situated near shopping, dining, parks, and major commuter routes, it is turnkey and just minutes from Dulles Town Center, Dulles International Airport, and the W&OD Trail.This may not last long so schedule your tour!

45428 Oak Trail Sq, Sterling

Listing courtesy of Samson Properties. Contact: 7033788810
$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

Listing courtesy of Douglas Elliman Jupiter. Contact:

$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

Listing courtesy of Florida Living Realty. Contact:

$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

Listing courtesy of Waterfront Properties & Club C. Contact:

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the South Jersey Shore Regional Multiple Listing Service. Real Estate listings held by brokerage firms other than Jack And Jill Team eXp Realty LLC are marked with the Broker Reciprocity logo (a little black house) and detailed information about them includes the name of the listing brokers.

Information is deemed accurate but not guaranteed.

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