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Nestled off the prestige Young’s Road sits an exquisite 12.75 acre equestrian estate. With English provincial influence the main quarters showcases wide plank hardwood floors and doors sourced from the property, brick floors, and a steep hipped slate roof. The main quarters has a generous master on the main floor with French doors to a private courtyard, the upstairs boasts a large bedroom and full bath overlooking the sunken riding arena. Adjacent to the upstairs bedroom is a large fully appointed apartment with its own private entrance with robust rental history. A large detached two car garage sits tucked away to not obstruct views of the pastures. 5 stall barn with wash rack, feed room, tack room, ample storage above. All 6 mature pastures have water systems and large run in sheds. A picture perfect fully equipped cottage sits in mature landscape adjacent to the barn perfect for a trainer. This mature equestrian estate was perfectly thought out and appointed with seamless design for the equestrian in mind.

222 Goodwill Rd, Southern Pines

Seller Representative EVERYTHING PINES PARTNERS-FAYETTEVILLE

Buyer Representative

$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

$749,500

4 Beds ⋅ 4 Baths ⋅ 100552733 MLS

This beautiful property is back on the market due to no fault of its own. The buyers plans changed! BARGAIN Once priced well over $1 million, now attractively priced at $749,500 and offered with a recently surveyed extra building lot suitable for a duplex! Circa 1890 3-4BR/3.5BA 3,200+SF extensively renovated home on a large lot in the highly desired downtown Southern Pines. This unique home offers numerous options. An additional home can be constructed on this lot, or even a duplex! Perhaps a garage with an apartment above, or it can be used as a single-family home with an in-law suite, or even multi-family (3 units total). The family room upstairs could easily be changed back to a 4th bedroom. The main floor boasts a beautifully updated kitchen with ZLINE appliances, gas cooktop dual fuel range, granite counters, and black walnut trim built-in cabinets. The first floor has a new luxurious master bath with a spacious primary bedroom, solid shelving in the walk-in closet and direct access to the laundry/mudroom. The outdoor living space is amazing with a wraparound porch, 2 screened porches, rear deck and wood fencing. The upstairs includes 2/3 spacious bedrooms (2 full baths), a family room (4th BR) that also includes a kitchenette+ an additional spacious laundry room and beautifully hand-tiled full bath with walk-in shower. The basement is dry and adds lots of storage space, accessible from exterior stairs in rear of house. Note the home has 3 electric meters, 3 water heaters and two heat pumps (first floor unit is <10 yr old). The current owner has spent hundreds of thousands $ to carefully restore this home to its current splendor. Anderson windows 2022, Hardie Plank siding 2022, plumbing and electrical updates 2022-2024, Carolina Basements added additional support to basement 2022. New or newer: fixtures, paint, gutters, kitchen, laundry, baths, flooring, insulation, gas lines, fence, and appliances. Shown by appointment to pre-qualified buyers.

280 W Connecticut Ave, Southern Pines

Courtesy of 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

$599,998

3 Beds ⋅ 3 Baths ⋅ 100545485 MLS

Charming 1930s Remodeled Bungalow in Southern Pines! 2263 Total Heated SF, 732 SF finished basement apartment with kitchen, plus additional 1531 SF between main level and top floor. Step into timeless character with modern comfort in this beautifully remodeled 1930s bungalow, ideally located minutes from downtown Southern Pines and Hwy 1. Thoughtfully updated from top to bottom, this home blends historic charm with stylish upgrades and flexible living spaces. Main Level: Inviting covered porch with tongue-and-groove ceilings. Refinished original hardwood floors and stained-glass windows that honor the home's history. Open living area with exposed beams. Completely renovated kitchen featuring new cabinetry, granite countertops, tile backsplash, gas range, and a spacious island with seating. Two comfortable guest bedrooms and a full guest bathroom with a tiled walk-in shower & towel warmer! Upper Level Owner's Retreat: Private owner's suite with a cozy sitting room and gas fireplace. Large bedroom with abundant natural light. Expansive walk-in closet with windows and a charming bench seat. Spa-like bathroom offering a pedestal soaking tub, large walk-in tiled shower, and dual vanities. Basement Level (Potential Rental or Guest Suite): Accessible from both inside the home and a separate exterior entrance, the lower level offers exceptional versatility. This finished space includes its own kitchen with electric range, Comfortable living room with exposed beams, and Full bathroom. Perfect for guests, multigenerational living, or rental income opportunities! Additional features include: Tankless gas water heater for energy efficiency and endless hot water Private driveway leading to a 2-car detached garage Stamped concrete patio with café lights--ideal for outdoor dining and entertaining Picket Fenced side yard Outdoor grilling station This beautifully restored bungalow offers historic charm, modern convenience, and rare flexibility--all in a prime Southern Pines location!

132 Tower St, Southern Pines

Courtesy of Everything Pines Partners LLC

$965,000

4 Beds ⋅ 4 Baths ⋅ 100537772 MLS

Welcome to 555 NE Broad Street, an elegant Mediterranean-style custom home just two blocks from downtown Southern Pines. Built in 2019 and freshly painted, this beautifully maintained residence blends timeless architecture with modern comfort. The all-brick exterior, mature landscaping, and fenced backyard create a private oasis in an unbeatable in-town location. Inside, ten-foot ceilings and generous room sizes offer an airy, luxurious feel. The main level features a bright living room with a gas fireplace and built-ins, and a flexible guest suite that also makes the perfect home office. The chef's kitchen impresses with professional-style appliances, a walk-in pantry, and a charming brick wine room—ideal for entertaining. Upstairs, the primary suite offers dual walk-in closets and a spa-like bath with a soaking tub and glass shower, while two additional bedrooms share a large dual-vanity bath. Outside, an oversized single-car garage with extra ceiling height adds functionality, and the finished studio apartment above provides an ideal space for guests, rental income, or a private retreat. Thoughtful upgrades include a whole-home generator, tankless water heater, irrigation system on a separate meter, reverse-osmosis filtration, engineered hardwood floors, and CAT-6 wiring. The fenced yard with a covered patio is perfect for quiet evenings or gatherings. Combining luxury, flexibility, and location, this one-of-a-kind home captures the best of Southern Pines living—walkable to shops, dining, and parks, yet offering space, privacy, and timeless design. 555 NE Broad Street is the perfect blend of sophistication and convenience in the heart of downtown!

555 Ne Broad St, Southern Pines

Courtesy of Front Runner Realty Group

Buyer Representative Keller Williams Pinehurst

$1,340,000

5 Beds ⋅ 6 Baths ⋅ 100413434 MLS

Beautiful Southern Pines horse country living awaits at this impressive farm! On over 11 acres of established, fenced pasture you'll find a true retreat! Behind the custom iron gate, down a long recently repaved driveway you'll find this recently remodeled spacious home overflowing with natural light, beautiful high ceilings and rustic, contemporary charm. The home features over 5200 SF of heated living space, 5 bedrooms, 4 full baths and 2 half baths. Hardwood flooring was recently added by the current owners as well as numerous other updates! (List Available). The floor plan is perfect for entertaining and hosting a crowd! If you live here, you will be the favorite hangout! Main floor master suite with spacious walk in closet and large bathroom with tub and shower. Another main floor bedroom with en-suite bath (recently remodeled). The kitchen features new appliances, a large island & plentiful counter space overlooking the pastures in the rear of the home. Stepping outside to the screened in porch, you'll enjoy the privacy this estate offers. A short stroll down to the pool, cabana, half bath and lounge area. The pool area is fully fenced and ready for you to enjoy when the weather warms back up! Back inside the home, the upstairs features a large loft/den area, and 3 bedrooms, 2 full baths (one en-suite). There is a ton of storage at this property! Three car garage with workshop space as well as walk in storage from the upstairs loft area. The barn features a tack room, hay storage area, 3 stall shedrow and charming studio apartment above the barn. The rear of the property features 3 large pastures with run in sheds and a new grass riding arena. This area enjoys wonderful hacking and access to the Walthour Moss Foundation, sandy lanes and beautiful footing year round! Don't miss your chance to enjoy Southern Pines horse country at its finest!

470 N Fort Bragg Rd, Southern Pines

Courtesy of Front Runner Realty Group

Buyer Representative Front Runner Realty Group

$2,050,000

5 Beds ⋅ 6 Baths ⋅ 100435698 MLS

This is your opportunity to buy into one of the most exclusive neighborhoods in Moore County. The main house offers over 3,700 sqft of well appointed living space. As you climb the front stairs, you notice the attention to detail immediately with natural gas lanterns and expansive front porch. As you enter the foyer, the details continue. Updated White Oak quarter sawn hardwood floors are located throughout main living and kitchen spaces. The open floor plan invites you into the living room which includes coffered ceilings, stone fireplace and wall to wall full windows leading out to the covered patio. A 2021 kitchen remodel awaits. No expense was spared on this extensive remodel. The kitchen includes Custom Inset kitchen cabinets throughout, Silestone Calcutta Quartz countertops with a suede finish, Wolf double over gas range, Sub Zero Refrigerator with a 64 bottle Wine Refrigerator, two top of the line Kitchen Aide Dishwashers, Scotsman Icemaker, and Commercial Grade exhaust fan. Updated light fixtures are found throughout the foyer, living room and kitchen. A executive office is found opposite the kitchen and dining room with coffered ceilings and Brazilian Walnut flooring. Three additional bedrooms are found down the hall, all with their own ensuite bathroom. The decorated primary bedroom includes Brazilian Walnut flooring, recessed ceiling, and private door out to the back patio. Primary bathroom offers dual vanity sink, garden tub, huge walk in shower and walk in closet. If the interior blew you away, wait until you see the back patio. The covered porch leads out onto the back patio and heated pool! Freshly painted exterior, solar panels, WHOLE HOUSE GENERATOR, fully encapsulated crawl space and whole home dehumidifier, chicken coup, fenced garden, exterior lighting, round out the exterior. 1,200+sqft 1 bed/1bath apartment located above the four car garage. More updates than can be listed! Did I mention the home sits on 10+ acres! Exclusivity awaits!

405 Pine Barrens Vis, Southern Pines

Courtesy of Nexthome In The Pines

Buyer Representative Keller Williams Pinehurst

$1,595,000

4 Beds ⋅ 4 Baths ⋅ 100473211 MLS

250 Valleyfield Lane circa 1988 main residence is 4,304 SF with 4BR/3.5BA plus an 885 SF 1BR/1BA guest apartment over the garage with 5 acres and a pool. 246 Valleyfield Lane is the log cabin/guest cottage 1,616 SF, 3BR/2BA built in 2001 on 8.37 acres with 6 acres of fenced pasture, a pond, and stable/run-in shed. This magnificent property is a builder's personal residence and office ideally located just outside Southern Pines city limits in Weymouth and is just over 200 feet from Weymouth Woods Nature Preserve trails. Horse farms are on each side of this farm, and it is a short drive to the quaint downtown area. The main residence has abundant peachtree windows and doors, a 7-year-old cedar shake roof, real stucco, and wood exterior. The massive front doors and mantle are made of Linden wood, and many interior doors are antiques from the Holly Inn in Pinehurst. All bedrooms have walk-in closets and ensuites with the master suite having 3 walk-ins. The great room has a massive stacked stone, wood-burning fireplace and is open to the second floor. Formal and informal living spaces, and beautiful outdoor living on the stamped stone patio, inground pool, and pergola. The oversized garage (885 SF) is connected by a breezeway and has a recently renovated 1BR/1BA guest apartment overhead. A detached 3+ bay equipment shed with electricity is at the edge of the parcel. The guest cottage is an authentic log cabin with an open great room, wood-burning stone fireplace, and front porch overlooking the pond. Newer no-climb wire & wood-fenced pastures. Both homes have home warranties from America's Preferred Home Warranty. Termite warranties with BugOut. The generator does not convey. 2 large-yield wells service each home/parcel. Please limit showings to serious, pre-qualified buyers. The seller will need at least 60 days to close or seller possession after closing. The last sale fell through due to no fault of the property.

250 Valleyfield Ln, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative Keller Williams Pinehurst

$1,292,000

3 Beds ⋅ 4 Baths ⋅ 730849 MLS

222 Goodwill Road, Southern Pines

Courtesy of EVERYTHING PINES PARTNERS-FAYETTEVILLE

Buyer Representative EVERYTHING PINES PARTNERS-FAYETTEVILLE

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Homes with Garage Apartment in Southern Pines, NC

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