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The Perfect Swing (Sleeps 8 + Pool Table)

Comfortable and spacious 2600 sq ft; 4 bedroom / 3 full bath home. Conveniently located to both the Village of Pinehurst and Downtown Southern Pines, as well as some of the best courses in the country, The Perfect Swing is ideal for both families and golf retreats. This spacious and fully appointed home is your resort home away from home. When you are not on the course, enjoy the pool table, fire pit or relax on the custom built porch swing! *4.9 rating and 100+ reviews prior to current owner*

Clearwater Moonlight lake view

LAKEHOME w/20th-century charm &modern amenities,offers a luxurious retreat like no other. Nestled on a private PENINSULA features 3beds/2.5 baths in the main house and an extra bed in the cabana. The stage is set for memorable gatherings, whether inside or outside to thesun-soaked lakefront sunroom.The true magic lies outside, where you'll find a PRIVATE BEACH,DOCK,& CABANA.This property offers THE WATERFRONT LIFESTYLE while reveling in world-class sunrises and sunset ! No parties are allowed

Private Wooded Retreat-Salt Water Pool- 22 acres

Private luxury and stylish retreat set on 22 acres. Nestled in the woods with expansive views. Star gaze upon the gorgeous night sky with no light pollution. A nature lovers' paradise! This one level contemporary home features a gorgeous salt water pool that's heated during the cooler seasons. Grill pool side over an open fire in pit or there's a gas grill. Hike through 11 acres of woods on property. Kayaking, trails, farm to table restaurants, breweries, farms and concert/event venues nearby.

Pineland Patio Golf & Game

Drive 2.3 miles to the Southern Pines Golf Club, 7.5 miles to the Pinehurst Resort! Enjoy entire 2500 sqft home with 4 br, 2 living areas, kitchen, 3 full baths, dining room, and a study. Relax outside on the bench swing beside the firepit on the charming brick patio under established longleaf pine trees. 2.5 miles from downtown Southern Pines, less than 1/4 mile from dog-friendly hiking trails on beautiful 500-acre Weymouth Woods State Park. 25 minutes to the Ft. Liberty Longstreet Gate.

A Cozy Retreat on No. 5

Across from the Harness Track and an easy walk to the main clubhouse at Pinehurst sits our villa on the 2nd hole of the Ellis Maples designed Pinehurst No. 5. Our newly renovated 2nd floor unit has 3 bedrooms, 2 bathrooms and and open floor plan. With seating for 8 and 5 beds, you can bring the whole family comfortably. Cook dinner in the kitchen equipped with new stainless and enjoy a glass of wine out of the cooler. This unit has two porches, and both are great for your morning coffee.

Upscale City Cottage Getaway

Modernized newly renovated mid century cottage in the city conveniently close to everything the city and surrounding areas have to offer. Pet friendly with a huge fenced in private backyard with large entertaining space. It is 2 Miles from Wake Forest University and Reynolda Gardens. Multiple shopping centers with various grocery, shopping, pharmacy options and many restaurants are within 1 mile. It is also a mere 30min drive to Pilot Mountain State Park for hiking and stunning views.

Delightful 1BR Camper/RV-Glamping in the City

This private hideaway sleeps 3 or a couple w/2 kids. Offers a tranquil blend of comfort and charm. Savor meals by the gas grill, then unwind around the glowing fire pit beneath the stars. Just 5 mins Oak Hollow Lake, and a leisurely stroll to High Point Greenway and City Lake, adventures wait with kayak & canoe rentals. Whether you're seeking serenity or outdoor excitement, this is glamping at its best. Come create memories that linger long after you leave.

Timeless Tudor - In the heart of Southern Pines!

Consider this your home-away-from-home! Enjoy your visit to the "land of the pines" by staying in the Timeless Tudor. Capable of comfortably hosting groups of up to 10, this beautifully updated 100 year old home is located just two blocks from downtown Southern Pines and boasts—among its many favorable features—4 comfortable bedrooms, 2 and a half bathrooms, and a private backyard oasis.

Easy Walk to Downtown House-Par for the Course #2

Discover our three-bedroom cozy home in Golf Town, perfect for a guy's golf weekend or a family vacation. Located steps from downtown's restaurants, cafes, and shops, our house features three bedrooms, two and a half baths, and a spacious backyard. Enjoy walking to local attractions, relaxing or dining outdoors around town. Ideal for those who love golf, small-town charm, and convenience.