Happy Trails: 8 Properties with Hiking and Riding Paths

By Grace Cassidy

Summer is the perfect time of year to enjoy hiking and other outdoor activities. If you love being outdoors and want the convenience of having a hiking trail right in your backyard, look no further. These eight homes all include access to trails or private trails of their own right within the property, making them ideal for anyone who prefers to spend time outdoors.

Long Island, New York

9 Kaintuck Lane, Locust Valley, New York | $2,488,000

This four-acre property was designed for outdoor living. Landscaped walkways loop through the property, while a babbling brook will easily become the soundtrack to every summer spent in this home. Storybook secret gardens, gazebos, specimen trees and a cottage-like storage shed are also included, and a rear deck is ideal for entertaining during the warmer months.

The nearly 5,000-square-foot home comes complete with five bedrooms, four-and-one-half bathrooms, hardwood floors, a double-height entry, chef’s kitchen, multiple fireplaces and a finished lower level.

59 Shore Road, Westhampton, New York | $18.5 million

Spanning two acres with 380 linear feet of frontage on—and endless views of—Moriches Bay, this Westhampton retreat is ideal for anyone who likes to get outdoors and spend time in nature. The property also includes a private boat dock, gunite zero-edge pool and spa, as well as a separate two-bed, two-bath carriage house.

The main house spans over 12,000 square feet in size with eight bedrooms and nine full bathrooms, designed by architect Craig Arm and interior designer Bunny Williams. Features include a well-equipped chef’s kitchen, butler’s pantry, atrium and a home gym.

New York

15 Cox Drive, Warwick, New York | $4.5 million

Situated on nearly 38 acres of land, this Warwick property is a private getaway offering the utmost seclusion and quiet. Homeowners enjoy scenic trails that wind through the entire property, creeks, ponds and natural wildlife.

Inside, the 6,227-square-foot home features four bedrooms, two-and-one-half bathrooms, an office, an open kitchen overlooking the koi pond and effortless indoor-outdoor living and entertaining. Nature surrounds the home and is accessible from every room.

Hudson River Valley

200 Long & Winding, Garrison, New York | $3,999,000

This Garrison home offers total privacy on just under 32 acres of wooded land that offers direct access to the famed Appalachian Trail. Residents will love the endless views of the Hudson River, Bear Mountain Bridge and Shawangunk Mountains in this 1997 Frank Lloyd Wright-inspired home.

Inside 3,625 square feet, the home is host to three bedrooms and three-and-one-half baths, a chef’s kitchen with stainless steel appliances, a sunken living room with vaulted ceilings and a stacked stone fireplace, and French doors that lead out to a wide patio.


333 S. 2nd Street, Aspen, Colorado | $350,000 per month

This stunning Aspen rental home connects directly to Little Cloud Trail, which takes hikers right up Aspen Mountain. When you’d rather hunker down at home, you can still enjoy the great outdoors on the expansive patio, complete with a lap pool and fire pit.

The home spans over 9,000 square feet in size and features six en-suite bedrooms, a private terrace with mountain views off the primary suite, a generous kitchen and multiple living spaces.

295 Gray Head Lane, Telluride, Colorado | $18.5 million

For those who love not only to hike but also to horseback ride, consider this Telluride estate. The private 35-acre retreat features hiking and equestrian trails, as well as multiple terraces, a trout pond with a pondside cabana, fire pits, outdoor kitchen and stunning natural views. As part of the Gray Head community, homeowners also enjoy access to community amenities such as a tennis and basketball court, ski valet, and ice-skating rink.

Designed by Poss Architecture, the 11,825-square-foot home includes six bedrooms, eight full bathrooms, two half-baths, a gourmet kitchen, floor-to-ceiling windows, multiple fireplaces and designer touches throughout.


24810 Jacob Hamblin Road, Hidden Hills, California | $11.95 million

Located in beautiful Hidden Hills, this California retreat offers access to hiking trails right at the end of the block. The 1.64-acre property allows for outdoor living and entertaining year-round with sliding glass doors that lead out to the expansive pool deck. An outdoor fireplace, in-ground trampoline, limestone fountains, putting green,and mature fruit orchard are also found on the property. Plus, each bedroom features French-door access to the gardens.

The 1964 home recently underwent a total renovation and spans 6,890 square feet in size. Five bedrooms, seven-and-a-half bathrooms, a chef’s kitchen with top-of-the-line appliances, white oak flooring, home theater and luxe primary suite with dual bathrooms are included.

51 Monarch Beach Resort, Dana Point, California | $6.7 million

This beautiful Dana Point condo offers access to a walking path that leads directly to Salt Creek Beach and The Ritz Carlton. Outdoor living and entertaining are made simple with accordion doors that open from the living area to the outdoor patio with a built-in BBQ, bar and modern glass fire pit.

The condo offers 3,797 square feet of interior living space with three bedrooms, three-and-a-half bathrooms, stunning water views throughout, hardwood floors, a wine cellar, open kitchen with professional-grade appliances and more.


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Mike McNamara

Mike McNamara

A Las Vegas Realtor since 2008. Mike has a wide range of knowledge around all things Las Vegas.

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