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Charming Home Steps from Downtown Southern Pines Don't miss this incredible opportunity to live just a blink away from the heart of downtown Southern Pines! This stunning home is bursting with curb appeal and thoughtful custom touches throughout. Inside, you'll find quartz countertops in the kitchen, an instant, never-ending hot water system, and vaulted ceilings in both the master bedroom and additional bedroom. Unique features like a laundry chute—something we've all dreamed of—paired with custom wood shelving and craftsman-style trim throughout make this home truly one-of-a-kind. Cozy up by the gas fireplace with its custom mantel, or enjoy the elegance of stained oak floors underfoot. The exterior is just as impressive with durable Hardy Plank siding and a welcoming front porch, perfect for sipping sweet tea and chatting about the weather. Additionally, there's a spacious 19x11 carriage house that can be used for parking or extra storage. With so many custom details and charming features, this home is an absolute must-see. Schedule your showing today!

430 N May St, Southern Pines

Courtesy of Carolina Property Sales

Buyer Representative Realty World Properties of the Pines

$489,420

3 Beds ⋅ 3 Baths ⋅ 100376264 MLS

Desirable location! Near downtown Southern Pines, find this new construction modern cottage perfectly charming. Starting with a welcoming front Southern porch, make your way inside to find this comfortable floor plan ensuring the home functions efficiently and does not waste any space. Enjoy this relaxing living room with a fireplace which leads through the dining area and into an open kitchen featuring a kitchen island, beautiful appliances, separate pantry. The owner's suite is on the main floor along with an additional bedroom and mud room/laundry room with a second entrance to the back yard. Upstairs is the third bedroom, full bathroom and an amazing bonus space! In the back you will find another covered porch for outdoor enjoyment. Included is a carriage house for a multitude of uses.

275 Duncan Rd, Southern Pines

Courtesy of Rhodes and Co LLC

Buyer Representative Rhodes and Co LLC

$1,200,000

4 Beds ⋅ 4 Baths ⋅ 100566173 MLS

Welcome to 260 South Ashe Street--where timeless elegance meets modern comfort in the historic downtown district of Southern Pines, North Carolina. This beautifully renovated Dutch Colonial, offers over 3,400 square feet on a spacious 0.36-acre lot, just steps from the local ice cream parlor, library, theatre, boutique shops and dining, Several blocks away are tennis courts and a playground. Within two miles is world class golf at the 18 hole Donald Ross designed Southern Pines Country Club, where memberships are available. Blending 1920s charm with modern upgrades, the home features 4 bedrooms, 3.5 baths, a finished basement, and flexible living spaces throughout. Enjoy two gas fireplaces, one on the lovely screened in porch, a chef's kitchen with updated appliances, and thoughtfully designed outdoor areas including a stone patio, garden, and private, lighted recreation (basketball) court. Smart additions like a tankless water heater, programmable thermostats, Sonos sound, and security system add sustainability and peace of mind. Convenient features include a laundry room as well as a second washer and dryer on the bedroom level. Work from home in the quite, light-filled spacious office. A carriage house and detached two-car garage provide endless possibilities for work, fitness, or creative use. Natural gas supplies heat to combo heat pump, tankless water heater and two fireplaces. Close proximity to Ft. Bragg. A rare opportunity to own a piece of Southern Pines history--this is downtown living at its finest.

260 S Ashe St, Southern Pines

Courtesy of Coldwell Banker Advantage-Southern Pines

Buyer Representative Keller Williams Pinehurst

$1,400,000

6 Beds ⋅ 7 Baths ⋅ 100561915 MLS

Rare Opportunity to own a piece of history and one of the finest homes in Weymouth Heights Circa 1924. Just steps away from the Weymouth Center & Gardens and Duncraig Manor B&B, this outstanding 6 BR | 6.5 BA residence sits on almost 2 acres. Enduring slate roof and entry, native stone, brick and wood exterior. Circular drive framed by mature landscaping leads to slate walk and stately double-door entrance. Foyer opens to formal living spaces with exceptional millwork and staircase to second level. Formal Living Room with gas fireplace flows to private Study/Office with built-ins and second gas fireplace. Main-level large Primary Suite offers soaking tub, walk-in shower, dual vanities with quartz countertops, Bluetooth fan/light and generous walk-in closet with custom built-ins. Formal Dining Room showcases intricate wood detailing, decorative fireplace, chandelier and ornate corner niches. Just beyond dining room, separate Coffee/Wine Bar with sink & wine cooler serves as dedicated entertaining space, with Powder Room nearby. Timeless Classic Kitchen completely renovated with soft-close cabinetry, granite countertops with island and breakfast bar, natural gas cooktop with pot-filler, double wall ovens, large walk-in pantry and refined lighting. Adjacent Family Room features wood-burning fireplace, built-in bookshelves, French windows and breakfast/informal dining area which looks out onto private brick courtyard. Second Floor of main residence, accessed via foyer staircase, presents three private Guest Suites, each with full bath, including a second Owner's Suite with marble floors & counter and generous dressing room. Connected, fully-renovated two-story Carriage House Apartment includes 2 bedrooms, 2 full baths, full kitchen, living/dining area, private entrance and fenced yard--integrated yet offering flexible use, enabling multi-generational living or rental income. Recently built Pergola offers Covered Parking & Outdoor Living Space. Separate Owner's entry opens into Family Room. Property includes fully fenced side and back yards with ornate iron gates throughout, Original Double Carriage House Doors on Garage, gardens, wired outbuilding with storage, workshop, chicken coop and run. Secondary Circle Drive and gate on N Valley Rd. Established landscape features Camelia, Azalea, Magnolia, Dogwood, Japanese Maple, Rhododendron, Mountain Laurel, Fig, Lady Banks Roses, Crepe Myrtle, Hydrangea, Oak Leaf Hydrangea, Heirloom Roses, Gardenia and more. Notable updates: whole-house water filtration, tankless natural gas water heater, electrical and plumbing improvements, updated lighting and fans, renovated kitchen, primary bath updating, carriage house renovation, decorative gates, front drive, and covered pergolas. Original shutters stored in garage. Allowing showings and accepting backup offers.

110 N Highland Rd, Southern Pines

Courtesy of eXp Realty

Buyer Representative Keller Williams Pinehurst

$1,945,000

4 Beds ⋅ 4 Baths ⋅ 100552362 MLS

Twin Spires Farm represents the pinnacle of equestrian living, offering a rare blend of high-end luxury and robust agricultural utility in the heart of North Carolina's Horse Country. Nestled within the prestigious Hunting Hills and close vicinity to the 4,000 acre Walthour-Moss Foundation lands and the 500 acre Weymouth Preserve. This estate is engineered for the buyer who views the land not just as a backdrop, but as a lifestyle and a vocation. The property's professional infrastructure is anchored by an exceptional eight-stall center-aisle barn, featuring matted 12'x12' stalls, a wash and grooming stall with heat lamps, hot and cold water, a dedicated wash rack and a central vacuum system. For the buyer focused on the operational side of the land, the expansive 1,800-square-foot loft provides massive capacity for hay and equipment storage, while the detached Carriage House adds a two-car garage with a built-in workshop, perfect for managing estate projects, machinery, and daily maintenance. The residence itself is a testament to superior craftsmanship and architectural longevity. The open floor plan is defined by soaring 20'+ foot vaulted ceilings, exposed beams, and a gourmet Woodmode kitchen upgraded with commercial-grade Monogram appliances and a copper farmhouse sink, serving as the perfect retreat after a day on the farm. The layout is thoughtfully designed for multi-generational use, offering two large suites on the main level, two guest bedrooms on the upper level, including a dedicated office space. A separate, beautifully appointed one-bedroom apartment above the Carriage House. Additionally, with 500 square feet of unfinished attic space, there is significant potential to expand the living area to suit a growing operation or personal needs.Outdoor living at Twin Spires Farm is equally intentional, featuring a flagstone terraced pool area, an outdoor fireplace, and a fire pit that overlooks the irrigated, meticulously landscaped grounds. This seamless transition between the luxury of the home and the functionality of the pastures allows for year-round enjoyment of the estate's natural beauty. Whether you are hacking out directly to the nearby preserves, tending to horses in the professional-grade facility, or utilizing the dedicated workshop for your next project, this estate provides the privacy, scale, and specialized facilities necessary to cultivate a premier working farm. Situated just minutes from the world-class amenities of Southern Pines and the legendary golf of Pinehurst, Twin Spires Farm is a sophisticated sanctuary for those who demand excellence from both their home and their land.

185 Old Dewberry Ln, Southern Pines

Courtesy of Better Homes and Gardens Real Estate Lifestyle Property Partners

Buyer Representative Pines Sotheby's International Realty

$575,000

4 Beds ⋅ 3 Baths ⋅ 100411744 MLS

ASSUMABLE VA LOAN WITH YOUR VA ENTITLEMENT! This home has all the character you have been waiting for. The biggest asset is it's location. This home is situated on a private lot, whilst a convenient distance to pubs, shops, restaurants, and community events of the downtown lifestyle. Some updates have been made by the current owners for function. With a vision you could bring this all brick cottage into the modern lifestyle while keeping the charm intact. Beautifully crafted vintage windows provide all the natural lighting you could hope for. The sun room is warm, inviting looking out into the private garden and street. This home offers a cozy fireplace in the main living room accented hardwood floors, wide frames, and access to the sun room. You could fit a large sectional sofa in the living room to benefit your gatherings. This home features a basement which also boasts great natural light. The basement is used for a home gym, and wine storage. The owners utilized the adorable carriage house out back to house their bikes, kayaks, and hiking gear. The home is in very close proximity to All American Trail, Weymouth Woods, Reservoir Park, and Fort Liberty- but a stones throw from the energetic life of downtown.

145 S May St, Southern Pines

Courtesy of Love Pines Realty

Buyer Representative Keller Williams Pinehurst

$650,000

4 Beds ⋅ 3 Baths ⋅ 100377713 MLS

Timeless! This is a special home, one that shows true craftsmanship from a time when pride mattered and this amazing yard is the perfect compliment to this beautiful property! Current owners kept all the charm but brought it to today's standards. The chef's kitchen has custom wood cabinetry with black honed stone countertops, farm sink, and top of the line appliances while keeping the original hardwood floor. The Master bath features a huge walk-in tile shower with multiple shower heads. Formal living room with wood burning fireplace and formal dining room allow plenty of room for furniture placement and family gatherings. Downstairs features a gathering room area perfect for recreation and allows access to the Theatre room, office and additional living room. Upstairs features a loft, 2 bedrooms and bath. Outside, the backyard is completely fenced (PET FRIENDLY). There is a remote controlled power gate leading to the detached carriage house- big enough for lots of ideas if not storing your car. There is a large brick patio to enjoy outside time, also a separate built-in fire pit area for those special nights. The kids (of all ages) will LOVE the tree house. For the gardeners at heart you will appreciate the mature flowering azaleas, large dogwoods, grapevines and various hardwoods. This home is SO CLOSE to downtown SP, yet away from the hustle and bustle and feels so calm and peaceful. The oil heat furnace is great for WARM air all winter and is efficient, central AC for summer heat. Windows, roof, plumbing have been updated as well to allow easy comfortable living!!

440 Kensington Rd, Southern Pines

Courtesy of Rhodes and Co LLC

Buyer Representative Coldwell Banker Advantage-Southern Pines

$910,000

4 Beds ⋅ 4 Baths ⋅ 100464304 MLS

Step back in time to experience the perfect blend of historic charm and modern elegance in this stunning Southern Pines gem. Situated on 1.3 acres of lush, tree-lined landscape, this exquisite brick home, originally built in the 1940s, has been thoughtfully reimagined and rebuilt in 2017, preserving its old-world allure while introducing contemporary luxury. Located in one of Southern Pines' most sought-after neighborhoods, known for its grand homes and expansive lots, this residence is a rare find. The property invites you in with a picturesque front porch adorned with classic columns and an elegant stamped concrete floor, offering a peaceful retreat to enjoy the surrounding natural beauty. Inside, you'll be greeted by a seamless fusion of historic detail and modern comfort. The cozy living room, centered around a charming wood-burning fireplace, flows effortlessly into a casual dining area and a gourmet kitchen that is sure to impress guests! The incredible primary suite, is a true retreat featuring a spacious walk-in closet and a luxurious spa-like bathroom that exudes timeless elegance. This beautifully designed space is perfect for relaxation and pampering. Completing the main floor is a large laundry room, adding convenience to your daily routine. Upstairs, the home offers three beautifully appointed guest rooms, the sweetest loft area (the perfect space for a reading nook), and a spacious recreation room providing additional space for relaxation or hobbies, while the unfinished basement offers potential for a wine cellar or extra storage. If that wasn't enough, the large corner lot also features a delightful one-bedroom guest cottage (the old carriage house), complete with a full kitchen and bath—ideal for guests, an art studio, or a private home office. A rear-entry garage and circular driveway add both convenience and curb appeal.

215 Daffodil Rd, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative Everything Pines Partners LLC

$1,275,000

4 Beds ⋅ 5 Baths ⋅ 100440426 MLS

A Magnificent Home on almost an acre in Weymouth Heights within walking distance to downtown Southern Pines! Experience its early 20's Grandeur when walking in to this all brick Historical Home! Enter the Elegant front Foyer and walk through to the Living Room with its Coffered ceilings and cozy hearth Fireplace with gas logs. Timeless wainscoting and Coffered ceilings continue thru to the formal Dining Room. The Gourmet Kitchen features double oven, a gas cook top, a center island and breakfast bar. A dramatic cathedral ceiling gives the kitchen a warm open feel. There is a wet bar area off of the kitchen. This Home offers 4 bedrooms, 4 full bathrooms and 2 half baths. Three are bedroom suites-all with updated full bathrooms. Two of the suites are on the second level. Additionally, you'll find an upstairs walk in cedar closet. The 3rd bedroom suite with full bathroom on the main level is currently set up as an office that flows into the den/sitting room. Thru the front hallway is a convenient guest half bath. The 4th bedroom is over the adjoining 2 car carriage/garage. From the kitchen step up to a large butlers area that combines as a laundry room and includes a 2nd guest half bath.There is a full basement easily accessed from the kitchen and rear patio. Outside, meander the quaint brick pathways that lead you thru original archways to private courtyards and gardens surrounding the home. There is a whole house generator recently added!

815 E Massachusetts Ave, Southern Pines

Courtesy of Landseer Properties LLC

Buyer Representative Everything Pines Partners LLC

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