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$495,000
4 Beds ⋅ 2 Baths ⋅ 100597752 MLS
Some houses are just houses. This one has a corded phone stretched across the kitchen cabinets, a Carolina room made for Sunday coffee, and a driveway that has seen a thousand bikes thrown down midsprint. Welcome to 44 Winding Trail a solid, all brick, four-bedroom home tucked into one of Whispering Pines' most coveted streets, sitting on a lot just over an acre where the kids actually have room to run. Inside, 2,525 square feet gives everyone their own corner, and a bonus room off the garage currently a home gym, flexes into whatever your family needs next: office, playroom, in-law space. Built in the early 2000s and constructed the way homes used to be built, this one isn't cutting corners to hit a price point. And then there's Whispering Pines itself Eight lakes, golf, walking trails, and the kind of neighborhood where everybody waves. This isn't just a place to live. It's a place your family's story gets told for years to come.

44 Winding Trl, Whispering Pines

Listing courtesy of Love Pines Realty. Contact:

$584,999
3 Beds ⋅ 2 Baths ⋅ 100593115 MLS
Life slows down in all the best ways at this immaculate lakefront brick cottage in Whispering Pines. Mornings begin with coffee on the screened porch as mist lifts off the water, afternoons drift by on the paddleboat (yes, it stays), and evenings wind down by the fireplace with gas logs glowing at the touch of a remote. From the private dock and pier to the terraced backyard wrapped in upgraded landscaping, every inch of this property invites you outside. Inside, the home has been thoughtfully refreshed from top to bottom. The renovated kitchen shines with quartz counters, a new sink, refreshed cabinet doors and hardware, LVP flooring, a new range and microwave, and a clever stacked laundry and storage nook. The expanded primary bath is a true retreat with a luxury walk in shower, quartz topped vanity, generous storage, and heated floors underfoot. Both bathrooms have been modernized, fresh paint flows throughout, and commercial grade LVP, newer interior doors, doorknobs, and light fixtures give the whole home a crisp, current feel. The living room fireplace, painted a dramatic near black with a clean lined mantel, anchors a generous main living space, while the oversized dining room easily hosts a crowd. Outdoor living is where this home truly shows off: rear porch, patio, screened porch, refinished dock surface, new backyard steps and railing, and a bulkhead and dock constructed in 2015. The decorative lighthouse at the corner of the yard adds storybook charm (light no longer operable). A black vinyl coated chain link security fence surrounds the house and terraced yard, and lake fed irrigation keeps the entire lawn lush. The practical side impresses too: new HVAC, solar panels that keep electric bills reasonable, replaced windows, encapsulated crawlspace with abundant storage, a 9 year old roof, and a Clegg termite warranty. The heated and cooled 170 SF basement room makes an ideal flex space for an office, gym, or hobby room, and the oversized garage swallows vehicles and lake toys alike. A radon mitigation system was installed by past sellers purely as a precaution; radon has never been detected. Dock furniture, the dining room table and chairs, and select rugs are available for purchase. Lakefront homes in Whispering Pines don't come along often. Come see why.

22 Pine Lake Dr, Whispering Pines

Listing courtesy of LPT Realty. Contact:

$440,000
2 Beds ⋅ 3 Baths ⋅ 100583762 MLS
Beautifully positioned along the Whispering Woods Golf Course, this better-than-new townhome in coveted Whispering Pines showcases sophisticated design, elegant comfort, and impeccable attention to detail. Meticulously maintained and thoughtfully updated, this home features several updates to include a new HVAC system, Trex deck, and pathway lighting--providing peace of mind and effortless outdoor enjoyment. Filled with abundant natural light, the home showcases elegant design details throughout. The spacious living room is a true showpiece, featuring a stacked stone fireplace with custom built-ins, a gorgeous coffered ceiling, large windows with plantation shutters creating a bright and inviting atmosphere. Designed for both everyday living and entertaining, the kitchen offers a large island with breakfast bar seating, an abundance of cabinetry, a wall oven and cooktop, under counter lighting and a sun-filled window over the sink. Just off the kitchen, a formal dining room provides the perfect setting for gatherings and special occasions. At the front of the home, a cozy private office with glass French doors creates an ideal work-from-home space. The serene primary suite overlooks the golf course, featuring double-door entry into the spa-like bath with dual vanities, a walk-in shower, and an oversized walk-in closet. Step outside to enjoy the beautiful Trex deck complete with a solar sunshade--perfect for relaxing, entertaining, or simply taking in the peaceful golf course. Upstairs, you'll find a spacious loft, guest bedroom, full bath, and an impressive bonus room offering endless flexibility for hobbies, recreation, or additional guest space. This exceptional home combines timeless elegance, thoughtful upgrades, and a premier location. Move-in ready and truly delightful, this could be your opportunity to own one of Whispering Pines' finest townhomes.

1 Roins Roost Unit B, Whispering Pines

Listing courtesy of Keller Williams Pinehurst. Contact:

$550,000
3 Beds ⋅ 2 Baths ⋅ 100580419 MLS
33 Shadow Lane is located on a spacious lot in the desirable community of Whispering Pines. This well-built brick 3-bedroom, 2-bath home offers comfort, functionality, and plenty of room to enjoy both indoors and out. Step inside to find a welcoming living room featuring a cozy fireplace and bookcases. Perfect for relaxing evenings, the bright sunroom provides additional living space and is a wonderful spot to enjoy morning coffee while overlooking the property. The floor plan includes a large primary suite with an oversized walk-in closet and a private bath. Both secondary bedrooms are generously sized, offering flexibility for family, guests, or a home office. The kitchen features ample counter space, a convenient breakfast nook, and easy access to the formal dining room, making it ideal for both everyday living and entertaining. Additional highlights include a two-car garage plus an oversized golf cart garage, providing exceptional storage and convenience for golf enthusiasts, hobbyists, or those needing extra workspace.

33 Shadow Ln, Whispering Pines

Listing courtesy of Sandhill Realty. Contact:

$750,000
4 Beds ⋅ 4 Baths ⋅ 100580155 MLS
Back on the market with a $25k price reduction and under appraisal value. Beautiful two-story, 4-bedroom, 4-bath home in the heart of Whispering Pines! Offering an open and inviting floor plan, this home is designed for both comfortable everyday living and effortless entertaining. The main level features a formal dining room, dedicated home office, and spacious living areas filled with natural light. The well-appointed kitchen boasts a large coffee bar area, center island, abundant cabinet space, and plenty of room for gathering with family and friends. The spacious primary suite serves as a private retreat, complete with a luxurious ensuite bath featuring a walk-in shower, large soaking tub, and generous closet space. Upstairs, you'll also find a versatile flex space along with three additional generously sized bedrooms, including one with its own private ensuite bath. Situated on a beautifully maintained 0.53-acre lot, the backyard is truly exceptional. Enjoy outdoor living on the expansive patio overlooking a stunning in-ground pool and hot tub. Thoughtfully designed fencing separates the pool area from the remainder of the yard, creating both safety and functionality while preserving ample green space. The garage offers convenient side-door access and additional parking space large enough to accommodate a golf cart--a valuable feature in the golf-cart-friendly Village of Whispering Pines. As a resident, you'll enjoy access to the Village's numerous lakes, parks, and scenic trails. Experience a lifestyle filled with outdoor recreation, including fishing, water sports, golf, and community activities, all within one of the area's most desirable residential communities. Get the best of it all with a peaceful village lifestyle all within a short drive to dining, shopping and hospitals of Pinehurst and Southern Pines!!

45 Banning Dr, Whispering Pines

Listing courtesy of Berkshire Hathaway HS Pinehurst Realty Group/PH. Contact:

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