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$3,350,000
4 Beds ⋅ 4 Baths ⋅ 100584270 MLS
Welcome to Stone Oaks Farm, a remarkable private estate nestled on 6 beautifully landscaped acres in an exceptional location. Majestic old-growth oak trees frame the property, creating a stunning setting of natural beauty, privacy, and timeless elegance. The main residence offers more than 6,000 square feet of thoughtfully designed living space, complemented by an 802 square-foot guest suite above the garage featuring a full bath, steam shower, and sauna--perfect for extended family, guests, or a private retreat. Designed for both grand entertaining and comfortable everyday living, this home features 4 bedrooms and 3.5 baths, including an expansive formal dining room and a chef's kitchen equipped with dual islands, a six-burner Wolf gas cooktop, double ovens, a Sub-Zero refrigerator, and a butler's pantry with sink and additional dishwasher. A substantial 2005 addition introduced an extraordinary family room, private office, guest suite, and expanded primary living spaces. The stunning family room showcases exposed wood beams, hardwood floors, a wood-burning fireplace, and picturesque views of the outdoor entertaining areas. Adjacent to the family room is a sophisticated beverage center complete with a large wine refrigerator and beverage fridge. Beyond, a richly paneled executive library/office with its own fireplace provides the ultimate work-from-home environment. The main level also includes a spacious guest suite with a private bath. Upstairs, the luxurious primary suite offers dual walk-in closets and a spacious bath, while two additional bedrooms share a well-appointed full bath. Also added in 2025 is a beautifully outfitted entertainment and gaming space in the basement level complete with sink and wet bar. An ideal space for watching movies and sporting events. Outside, the estate continues to impress. A circular driveway and gated entrance welcome you to the property, while a three-car garage provides abundant storage. The backyard is designed for entertaining with a built-in grill, fire pit, and multiple outdoor gathering spaces including a beautiful stone koi pond. Beyond the immediate grounds, additional acreage offers unmatched privacy and includes a barn ideal for equipment, recreational vehicles, hobbies, or storage. This portion of the property may be subdivided if the owner so chooses. Completely fenced and meticulously maintained, Stone Oaks Farm presents a rare opportunity to own a private estate where luxury, comfort, and acreage come together in perfect harmony.

1680 Midland Rd, Southern Pines

Courtesy of Pines Sotheby's International Realty
$925,000
4 Beds ⋅ 5 Baths ⋅ 100416178 MLS
Beautiful green pastures surround this sprawling, charming home full of character and flanked by symmetric and handsome outbuildings in a totally private setting.This hidden gem, among other horse farms, is close to the new McDeeds Creek Elementary. school or choice of private K-12 school.A short drive to downtown Southern Pines, the Historic Village of Pinehurst, Pinehurst Resort and Country Club, Pine Needles and an award winning health facility including a new 4-story, 120,000 square foot state of the art Cancer Center. Great indoor/outdoor living including a welcoming fountain, circular driveway, slate patio, pergola and separate screened porch with wood burning fireplace.The interior is filled with historic features including original wide-planked heart of pine flooring, exposed beams, vaulted ceiling stone fireplace and stained wood trim. The updated kitchen with farm sink has a gas range, stainless hood and granite counter=tops. Immediately off the foyer the.family room features built in bookshelves with stone fireplace. Four bedrooms (two on main floor) all with en suite baths! The master suite features a sitting area and extra space for a home office! The over 4 acre property has 4 paddocks with creosote board fencing, a two stall barn w/large tack room and grooming/wash area. a 2 car garage with extra room and separate 2 bay carport. Ample storage in the two buildings, This is a dream property, with privacy, tranquil settings, multiple living areas, acreage and multiple outbuildings in a GREAT location! MOTIVATED SELLER.

2764 Camp Easter Rd, Southern Pines

Courtesy of Lin Hutaff's Pinehurst Realty Group

Buyer Representative Maria McBrayer, Broker
$1,820,000
4 Beds ⋅ 6 Baths ⋅ 100406237 MLS
NOW offering $10,000 in Buyer Concessions to be paid at closing towards buyer costs, rate buy downs or improvements! Elegant Equestrian Estate in the heart of Southern Pines Horse Country! The sprawling ranch style home offers character that is absent in newer construction. The home features soaring ceilings, multiple living & dining spaces, a library, space for wine cellar in basement, and an amazing screened in porch with an outdoor kitchen! The primary suite is on the main level and offers an expansive bath, closet area, and a home office. Upstairs you'll find 3 large bedrooms with ensuite baths and ample storage. The home is privately located at the back of the property, down a tree lined drive and surrounded by beautifully manicured lawns and fenced pastures. The 6 stall, center aisle barn offers spacious stalls, a tack room, a feed room, interior wash stall, 'guest quarters' with bath, and large storage bays perfect for equipment or carriages! There are 4 separate paddocks and two outside Run In sheds. There is no shortage of garage space on this farm! The 10 bay detached garage and workshop space is the perfect home for that car collection! Detached storage for RV or horse trailers and equipment is also available. This is a prime spot for an equestrian! The farm has direct access to the main section of the Walthour-Moss Foundation and is just a short hack from the Moore County Hounds Kennels. Downtown Southern Pines is just 1.5 miles away for fine dining, boutique shopping and nightlife! Pre-listing home, termite and septic inspections were completed and a full list of repairs/improvements are available upon request!

921 Yadkin Rd, Southern Pines

Courtesy of Better Homes and GardensReal Estate Lifestyle Property Partners/SP

Buyer Representative Better Homes and GardensReal Estate Lifestyle Property Partners/SP
$735,000
5 Beds ⋅ 4 Baths ⋅ LP731587 MLS
Beautiful downtown SoPines Property provides old world charm with the feel of all the modern conveniences. A main level primary bedroom with a modern bathroom and large closet. The kitchen with gas range, farm sink in the large teak butcher block island, ample counter space and cabinets. The eating area is just off the kitchen in conjunction with another area for gathering/office or den area that leads out to the expansive fenced side yard. The main living area offers a fireplace and cozy area for just relaxing or entertaining. Second level- 4 additional bedrooms, 3 of which are part of the original house with gorgeous hardwood floors and the other bedroom acts as a second-floor primary bedroom with its own bathroom. There is also a large playroom/living area on the second floor as well. There is a basement area that is around 425+/-sq ft along with additional storage space. The home sits on corner lot and offers various parking and entry options.

195 S Ridge St, Southern Pines

Seller Representative BH&G REAL ESTATE - LIFESTYLE PROPERTY PARTNERS

Buyer Representative

$1,575,000
3 Beds ⋅ 3 Baths ⋅ LP730995 MLS
Hobby Horse Farm is a charming gem nestled on Youngs Rd in the heart of Southern Pines Horse Country. This exquisite property features spacious living areas, a large kitchen and dining room, and inviting covered porches that open to a flagstone pool and deck—ideal for entertaining. The saltwater pool includes a hot tub, a diving rock, and a tanning ledge, all set within a beautifully landscaped backyard oasis. For the horses, there's a dedicated haven with expansive pastures providing plenty of shade, along with Run-In Sheds for shelter. The main barn boasts three stalls, a tack room, laundry facilities, a wash stall, and ample hay storage. Additionally, there's an auxiliary barn with two stalls, a separate tack room, and a wash area. Convenient, deeded private road access from Clearwater Creek Lane to barn for all your hay and feed delivery needs. Lush pastures, Run-In sheds, and a fenced riding area complete this turnkey farm. Just across Youngs Rd, the 4000+ acre Walthour Moss Foundation offers multiple access points and miles of sandy trails, hunt fences, bridges, and water crossings, perfect for hours of trail riding. Located approximately 2 miles from downtown Southern Pines and 7 miles from the village of Pinehurst.

3305 Youngs Rd, Southern Pines

Seller Representative BH&G REAL ESTATE - LIFESTYLE PROPERTY PARTNERS

Buyer Representative

$1,415,000
3 Beds ⋅ 4 Baths ⋅ LP743831 MLS
Experience Elevated Living in Southern Pines! Step into a HOME where luxury meets nature. This meticulously designed custom home offers expansive 360° views through floor-to-ceiling windows, immersing you in the serene beauty of Southern Pines. Daily sightings of deer and other wildlife become your routine, providing a tranquil backdrop to your everyday life. Situated in a community renowned for its equestrian culture, this property carries the legacy of its origins as part of a horse farm. The surrounding area boasts a vibrant horse-loving community, reflecting Southern Pines' rich equestrian traditions . Crafted with precision, the home features clean lines and modern aesthetics. The spacious common areas are perfect for entertaining, while the outdoor fireplace on the private back porch offers a cozy retreat for evening relaxation. Whether you're hosting guests or enjoying a quiet night in, the ambiance is both inviting and sophisticated. Designed by the owner, every detail of this home exudes excellence. From the thoughtful layout to the high-quality finishes, it's evident that this residence was built with passion and expertise . In a market where such unique properties are rare, this home stands out as a testament to luxury living intertwined with nature. Don't miss the opportunity to own a piece of Southern Pines' finest real estate.

250 Pine Needles Ln, Southern Pines

Seller Representative LOVE PINES REALTY

Buyer Representative

$2,600,000
4 Beds ⋅ 5 Baths ⋅ 100559343 MLS
Never Better Farm boasts all of the amenities of true equestrian living in the heart of Horse Country. The prime location is in close proximity to both the Walthour-Moss Foundation as well as Weymouth Preserve and just a short drive to downtown Southern Pines. Two parcels are being sold, the main home and farm(00040903) at 11.04 acres and vacant land 00040903 at 6.45 acres. After a day of riding in the dressage ring or sailing over the jumps on the lower parcel, enjoy a dip in the pool over looking beautiful pastures and vibrant landscaping. A true working farm, the property is anchored by 2 barns and a detached garage with 4 garage units and covered equipment shelter, perfect for plenty of storage or any farm projects that may need to be done. The barn closest to the home has 4 stalls, a laundry room and a dedicated wash rack. The second barn has 6 stalls and feed storage. Rich in Moore County history, part of the home used to be the property's original peach barn. Now a gorgeous multi-generational home, the property has one bedroom downstairs and 3 upstairs including the primary. Each bedroom has a private bathroom which also makes it exceptional for guests. This home is ideal for entertaining with a large living room featuring 17 foot vaulted ceilings, a wet bar and great indoor/outdoor living leading out to the pool. One of the most unique features of this home is the stunning brick floored tack room that is nestled in the center and leads out to a private grass covered patio. The buyer of this incredible estate will truly enjoy every aspect of this property, life here is ''Never Better.''

230 Old Dewberry Ln, Southern Pines

Courtesy of Keller Williams Pinehurst
$2,050,000
3 Beds ⋅ 4 Baths ⋅ 100536960 MLS
In and Out Farm - a private equestrian oasis in the heart of Southern Pines Horse Country! Set on 24 acres, this property offers peace, privacy, and a thoughtfully designed, fully functional facility suited to a wide range of equestrian pursuits. The inviting ranch-style home features a split floor plan with vaulted ceilings, warm wood accents, and equestrian-inspired finishes throughout. Built by a horse person, the home showcases custom tile work and a stunning mural of the Moore County Hounds by the late Danila Devins, a beloved local artist. The spacious back deck overlooks the pool and pond, creating the perfect spot for outdoor entertaining or quiet relaxation. The lower level includes a large flex room and full bath, ideal for a home gym or an office. The barn is the centerpiece of the property with 7 stalls, including a double-sized foaling stall, some with turnout access to multiple paddocks. The tack room features a private bath and office, while the upper level includes a 1,400 sqft, 2-bedroom, 2-bath apartment complete with an enclosed porch overlooking the paddocks—perfect for guests, staff, or additional income. Equestrian amenities include a fenced grass riding arena, large paddocks with run-in sheds, and an equipment barn ideal for tractor and trailer storage. The location is unmatched, offering access to the 4,000+ acre Walthour-Moss Foundation, where riders can enjoy miles of scenic trails, bridges, water crossings, and hunt fences for endless hours of riding and training. Whether you're seeking a professional training operation, a boarding facility, or a private estate, In and Out Farm offers it all—combining functionality, beauty, and the best of Southern Pines equestrian living.

207 Bump A Long Ln, Southern Pines

Courtesy of Better Homes and GardensReal Estate Lifestyle Property Partners/SP

Buyer Representative Old Glory Realty LLC
$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
$2,572,000
3 Beds ⋅ 2 Baths ⋅ 100388862 MLS
Blue Ridge Farm....historic farm in the heart of Southern Pines Horse Country. The classic hunt box style home was custom designed by John Foster Faulk, a prominent architect in Pinehurst in the 1960's. Over the years the current owners have worked with Carl Kessler, licensed in historical renovations, to ensure the historical integrity of the home & finishes. Situated atop a hill, the home & barn offer stunning views of paddocks, pond and riding field. Inside you will find architectural features such as solid 'wormy chestnut' doors, beams, paneling, and trim work throughout the living space, wood and herringbone brick floors, and an expansive brick fireplace. The 5000 sqft unfinished loft space houses the laundry room and multiple storage rooms with ample room to expand the main residence. The Downstairs you will find a 12 stall barn with 1 BR/1BA apartment or groom's quarters. There are double wash stalls, lovely tack and feed rooms, an interior treatment room, laundry facilities, separate office,and ample storage. The stalls are all rubber matted and oversized at 14x14 with custom grills & doors. The auxiliary barn, used by previous owners as the mare and foaling barn, offers 3 stalls two of which flank a viewing room w/ bathroom for foal watching, a workshop, and trailer/equipment storage. At just under 30.5 acres, there are 9 paddocks, multiple run in sheds and a large field for jumping and riding. The 'Walkerboy Eurociser' is an excellent addition to any training program! A full list of special features and a historical overview of the farm are available by request from owners. The detail and architectural features of this property are unmatched and would simply be impossible to recreate or build in today's world. This is truly a once in a lifetime property!

222 Cross Country Ln, Southern Pines

Courtesy of Better Homes and GardensReal Estate Lifestyle Property Partners/SP

Buyer Representative Everything Pines Partners Fayetteville
$2,275,000
3 Beds ⋅ 5 Baths ⋅ 100390860 MLS
Discover the epitome of equestrian living on this picturesque 12-acre horse farm nestled in North Carolina's Horse Country, boasting deeded easement access to the renowned Walthour-Moss Foundation. Just 2 miles from the vibrant Downtown Southern Pines, this property offers the perfect blend of tranquility and convenience. Featuring a meticulously designed 7-stall barn, 5 spacious pastures, and a fastidiously remodeled estate, this property caters to both horse and human comfort. The main residence offers 3 bedrooms, 3 baths, and 2 half-baths, while the guest quarters provide an additional bedroom and a private patio for relaxation. Remodeled between 2007 and 2009, every detail reflects a commitment to luxury and functionality, making this estate a haven for discerning equestrian enthusiasts. SEE SPECIAL FEATURES in DOCUMENTS for COMPLETE LIST!

207 Firleigh Rd, Southern Pines

Courtesy of DeSell & Co Realty Group

Buyer Representative Better Homes and GardensReal Estate Lifestyle Property Partners/SP
$2,080,000
3 Beds ⋅ 4 Baths ⋅ 100423641 MLS
This stunning equestrian estate brings an air of old world craftmanship to our modern day. The home was built in 2007 to look like an 18th century European mansion. Every detail has a special story that integrates pieces of family history with old world charm. As you walk through the exquisite handmade front door, you are greeted with a pure silver chandelier and sconces that are family heirlooms. The flooring throughout the home is wide plank and a combination of pine, walnut and oak. The stairs that lead to the second floor are purported to be from Dartmouth College. The fireplace in the family room is an 18th century replica of a Chatsworth House in England. The fireplace in the library boasts 18th century French marble. The hardware on doors and windows are antique, many from the 17th and 18th century. Diamond pain and stained glass windows were reclaimed from historic properties. The spacious primary suite is on the second floor and boasts his and hers closets and large bathroom with soaking tub. The sitting room with a surround of windows, gives you the feeling that you are sitting in the forest enjoying all that nature has to share. The kitchen is a chefs dream with a 6 burner Viking range, large center island and a butler's pantry. The property is just over 10 acres and includes three lush pastures and a 4 stall barn with center aisle. The barn has a one bedroom apartment upstairs and a studio apartment downstairs, perfect for guests or a farm manager. The Walter Moss Foundation and the trails around Weymouth Woods are a short hack. The location of this property is fantastic, offering seclusion in the heart of horse country, while being only a few minutes to all that downtown Southern Pines has to offer. Note. The septic permit for the house was originally submitted for a two bedroom home. This was not changed when a larger home was built. There is a room upstairs that has been used as a third bedroom. See floor plan.

176 Merry Way, Southern Pines

Courtesy of Pines Sotheby's International Realty

Buyer Representative Better Homes and GardensReal Estate Lifestyle Property Partners/SP
$1,050,000
4 Beds ⋅ 4 Baths ⋅ 100459930 MLS
THIS FARM IS CONTINGENT ON THE BUYER SELLING THEIR PROPERTY. PLEASE COME SEE THIS AMAZING FARM! One of the few farms available in Southern Pines, May View Farm is located on 10 acres of lush fenced pasture nestled among the pecan trees just minutes to down town Southern Pines. This Legacy built home was constructed in 2020. At almost 2600 square feet the house offers a downstairs primary suite, a secondary room that could be used as an office, formal dining room or another downstairs bedroom complete with it's own bath and lots of open space for you and your family and pets. Upstairs there are two bedrooms and two baths plus a mini office and bonus room....great private space for family or guests. The Great Room flows into the kitchen with its high end finishes and oversized island which is the perfect place to dine and entertain. The vaulted ceiling in the Great Room brings in lots of light and the brick fireplace with ship lap and beamed mantel are a gorgeous focal point of this space. Head out to the screened in and covered porch for morning coffee or a glass of wine as you watch your horses or donkeys graze in the amazing pasture! The barn offers in and outs so your equines can enjoy moving from pasture to pasture. The acreage is very flat and usable for schooling your horses or even add a ring or cross country course...many great places to do that! The first floor also has a spacious laundry and mud room area and outside there is an extra storage building! SO many great features about this newly built farm including: Whole Home Generator, Leaf Filter gutter covers, water and power to the barn and shed, 50 AMP RV/EV charging circuit, whole home water softener and UV filter and tankless hot water heater with temperature control. Bring you and your horses home to May View Farm!

2122 N May St, Southern Pines

Courtesy of McDevitt Town & Country Properties

Buyer Representative Front Runner Realty Group
$1,561,000
6 Beds ⋅ 7 Baths ⋅ 100508888 MLS
Experience horse country living in this 4,800+ sq ft custom home, nestled on over 11 pristine acres in this highly sought-after location of Southern Pines. Offering a rare blend of tranquility and convenience, this exceptional estate delivers the privacy of a countryside setting while remaining just minutes from town amenities, shopping, dining, and equestrian hubs. This must-see property is ideal for the discerning buyer seeking a one-of-a-kind farmstead. Tucked away behind mature landscaping and garden paths, the residence is beautifully sited to maximize views and serenity. A recently replaced roof and HVAC systems provide peace of mind, while thoughtful updates enhance the comfort and livability of the home. The estate includes a charming 3-stall barn, five fenced pastures, and direct access to miles of scenic riding trails. Both the Walthour-Moss Foundation and Weymouth Woods are accessible, making this an equestrian's dream. Enjoy summer days by the in-ground pool, where the pool liner and decking have been recently replaced, creating an inviting space for entertaining or relaxing. With spacious living areas, unique floor plan, and sweeping views, this home offers a rare opportunity to own a turnkey farm in one of the region's most coveted locations.

470 N Fort Bragg Rd, Southern Pines

Courtesy of Front Runner Realty Group

Buyer Representative Front Runner Realty Group
$450,000
3 Beds ⋅ 3 Baths ⋅ 100503174 MLS
Welcome to this meticulously maintained ranch home nestled on a generous 0.83-acre lot in desirable Southern Pines. Built in 1991 and lovingly cared for since 2020, this ~1,866 square foot residence offers the perfect blend of comfort and modern updates. The home showcases numerous recent improvements including a new roof (2025), new windows (2025), new hot water heater (2024), and a beautiful new front doors. Inside, you'll discover a thoughtfully designed floor plan with an abundance of natural light throughout. The kitchen has been beautifully updated with quartz countertops, painted cabinets, a stylish green subway tile backsplash, and a spacious farm sink, plus a convenient pantry closet for additional storage. The open concept living and dining areas create a wonderful flow for entertaining, anchored by a cozy propane fireplace. Fresh LVP flooring runs throughout the home, adding both durability and elegant appeal. The primary bedroom suite offers a generous walk-in closet, linen storage, and an updated bathroom featuring a double vanity and new shower. Two additional bedrooms with ceiling fans share a full bathroom. A half bath with new vanity completes the indoor living space. Step outside to enjoy the brand-new back deck overlooking the fully fenced yard—perfect for pets and outdoor entertaining. Additional features include a two-car garage, laundry area with extra storage, new sliding door to the backyard, updated light fixtures throughout, and a charming front porch. This turnkey property offers the ideal combination of location, updates, and comfortable living space in the heart of Southern Pines. **Seller is offering $2500 in seller credit to the buyer with acceptable offer!

485 Broadmeade Dr, Southern Pines

Courtesy of Everything Pines Partners LLC

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
$725,625
4 Beds ⋅ 3 Baths ⋅ 100421491 MLS
*Update* 10 day Upset bid period began 5/29/2024. High bid that day was $675K. If interested in placing a competing bid please contact Moore County Clerk of Court. Discover a rare 6-acre horse farm within 1 mile of downtown Southern Pines, NC, offering a unique blend of rural tranquility and urban convenience. 6 acres of land ideal for equestrian pursuits or a serene retreat. Prime location, just a short distance from sought-after downtown Southern Pines. Unlock the potential of this property, capitalize on its proximity to downtown Southern Pines, and make it your dream equestrian estate or country haven. Act now and transform this property into the gem it's destined to be!

380 Ox Ridge Ln, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative Meese Property Group, LLC
$2,900,000
4 Beds ⋅ 5 Baths ⋅ 100413239 MLS
Rare offering of magnificent estate ideally located off Midland Road between Southern Pines and Pinehurst. Stone Oaks Farm is nestled among 100-year-old Oaks on 6 acres with mature and extensive landscape. The 5BR/4.5BA main residence exudes casual elegance with original cottage built in 1929 with extensive remodel/addition completed in 2008. Highlights of the extraordinary home include: 27'x 25' vaulted & beamed great room with oversized wood-burning fireplace w/ gas starter; 700+ bottle wine vault w/bar, Chef's kitchen with double islands, pro series Wolfe gas cooktop, double ovens, pot filler, prep sink, Subzero refrigerator, Butler's pantry with 2nd dishwasher and sink. Spacious main level is ideal for entertaining with formal and informal living areas: bedroom with ensuite bath, wood-paneled study with coffered ceiling and fireplace, 23'x 15' formal dining with fireplace, sitting room with fireplace and sunroom overlooking back yard with stone patios, firepit and fishpond. Guest quarters located over 3 car garage has separate entrance, office + 5th bedroom, steam shower and sauna. Outdoor living areas also include a covered stone porch, private outdoor dining, and elaborate specialty lighting for nighttime enjoyment. The luxurious master suite offers 17 ft vaulted ceiling, his and hers custom closets, and a fireplace. The partially finished 1,100+SF basement has 9 ft ceilings, currently a home gym also great storage or flex space. 3 acre fenced rear yard is ideal for pets, second residence or guest cottage. Sonos speakers in courtyard convey. Newer barn for storage or workshop and ample space for pool and more. Private location with security gate just outside of city limits with natural gas and irrigation well. New roofs, multiple electric heat pumps & one gas heat system, security system, extensive irrigation, home warranty & termite contract. This meticulously maintained & special property will be shown to pre-qualified buyers only. Price is FIRM.

1680 Midland Rd, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative Lin Hutaff's Pinehurst Realty Group
$350,000
4 Beds ⋅ 2 Baths ⋅ 100525485 MLS
HUGE PRICE DROP DUE TO EAGER SELLERS!! 1.39 Acres!!! 4 BEDROOMS!! Building ready to be an accessory dwelling!! Minutes away from Moore County Airport, shopping, schools, community college, world class golf courses, hospital, parks, greenways and convenient to Raleigh and Fort Bragg! If you want a home with personality, this one delivers. Not a cookie-cutter build, but an older house full of quirks, charm, and history--set on a generous lot that offers privacy, space, and potential. With more than 2,400 heated square feet, a partially finished basement featuring a bedroom and office, plus a separate former commercial kitchen building, you'll have plenty of flexible space to shape to your lifestyle. Inside, you'll find original details that bring warmth and charm, from vintage finishes to a layout that feels unique at every turn. Outside, there's plenty of land for a garden, hobby farm, or just wide-open space to enjoy. Whether you want a creative project, a home with soul, or simply room to spread out, this property delivers. An added bonus to this property is the nearly 500sf separate outbuilding, formerly a licensed commercial kitchen, complete with running water and power. This versatile space opens up endless possibilities--whether you envision it as a catering hub, bakery, canning kitchen, studio, or simply a fully equipped workshop.

320 Aiken Rd, Southern Pines

Courtesy of Pinecone Real Estate, LLC
$999,000
100501976 MLS
Introducing Calloway Place, an exceptional 18-acre offering in the heart of Moore County's desirable horse country. Privately positioned yet convenient to Southern Pines, Pinehurst, and Fort Bragg, this rare tract presents an extraordinary opportunity to create a legacy property tailored to your vision. With gently rolling terrain, open clearings, mature timber, and serene woodland views, the land offers a beautiful canvas for a custom estate, refined homestead, private farm, or equestrian retreat. Whether you envision a thoughtfully designed residence, horse farm, gardens, paddocks, barns, riding trails, or a quiet escape with room to breathe, Calloway Place provides the space, setting, and flexibility to bring it to life. Surrounded by the acreage, privacy, and equestrian heritage that make Moore County's horse country so sought after, this property offers both lifestyle appeal and long-term investment potential, all within easy reach of shopping, dining, championship golf, and the charm of nearby Southern Pines and Pinehurst. A rare opportunity to secure 18 acres and create something truly exceptional in one of Moore County's most coveted settings.

Tbd Tbd Calloway Pl, Southern Pines

Courtesy of Pines Sotheby's International Realty
$735,000
5 Beds ⋅ 4 Baths ⋅ 100463651 MLS
Beautiful downtown Southern Pines Property located at 195 S Ridge St and provided old world charm with the feel of all the modern convenances on 3 lots (per GIS info see in Photos). This home offers a main level primary bedroom with a modern bathroom and large closet. The kitchen is a cook's dream with gas range, farm sink in the large teak butcher block island, ample counter space and cabinets. The eating area is just off the kitchen in conjunction with another area for gathering/office or den area that leads out to the expansive fenced side yard. The main living area offers a fireplace and cozy area for just relaxing or entertaining. On the second level you will find 4 additional bedrooms, 3 of which are part of the original house with gorgeous hardwood floors and the other bedroom acts as a second-floor primary bedroom with its own bathroom. There is also a large playroom/living area on the second floor as well. There is a basement area that is around 425+/-sq ft along with additional storage space. This space offers numerous options for a multitude of options, crafting area, den, play area, the list is endless. The home sits on corner lot and offers various parking and entry options. The front is a circle driveway, and the back is the main parking to the house with a one car garage that the past owner used as a workshop. The house is also hooked up to natural gas that runs numerous appliances in the house including a whole home generator.

195 S Ridge St, Southern Pines

Courtesy of Better Homes and Gardens Real Estate Lifestyle Property Partners

Buyer Representative Better Homes and Gardens Real Estate Lifestyle Property Partners
$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
$1,875,000
2 Beds ⋅ 2 Baths ⋅ 100405744 MLS
WELCOME TO FAIR OAK FARM - THE HEART OF SOUTHERN PINES HORSE COUNTRY. A charming gated equestrian Hunt Box on 15 beautiful acres. Enjoy the manicured landscaping, paddocks and equestrian amenities. Explore on horseback for hours through an extensive trail system. The newly renovated 2br/2ba apartment with wood-burning stove, kitchen/living area, office and large covered deck with hot tub overlook your paddocks. The grounds are well managed utilizing extensive engineered drainage & water diversion systems. The fabulous 18-stall barn was converted to 13 stalls (creating several oversized stalls) new roof, wash stall, tack room with laundry and kitchenette, and feed room. Ride year round in the new 80x140 covered arena with lights, kickwall & irrigation. There is also a grass training/jumping field with 20mx60m dressage arena. Ride from the farm to Walthour-Moss Foundation, Hunt Field, Weymouth State Park. There are multiple paddocks with run in sheds and a tractor shed. The owners performed extensive repairs and upgrades to the grounds, barn, apartment and tractor shed. There are several ideal areas on the farm for a new construction custom home. This is THE ideal setting for a private equestrian retreat and is an incredible opportunity as an income-producing training and boarding facilities with an on-site trainer. The quality, functionality, topography, location and beauty of Fair Oak Farm is an ideal setting for peace, tranquility and for living your dream. So close to Southern Pines amenities, veterinary services, shopping, restaurants. Expand your adventure into nearby Pinehurst - with Raleigh/Durham Airport just about 1 hr by car. There are multiple attachments to this MLS with personal property to convey, list of repairs and upgrades, all the features of Fair Oak Farm, trail map and more. Fair Oak Farm is a must-see!

500 Tremont St, Southern Pines

Courtesy of Ivester Jackson Christie's

Buyer Representative A Non Member
$1,275,000
4 Beds ⋅ 4 Baths ⋅ 100492865 MLS
Welcome to Tops'l Farm! Formerly owned by Master of the Moore County Hounds, Dick Webb and his family and named after his wonderful horse, Tops'l who competed at Madison Square Gardens! The original sign and the hunt master's horn convey with the property! This lovely recently renovated property on just under 10 acres offers a newer kitchen, baths, paint and so much more. This one floor home makes living in horse country a breeze and it backs up to the Walthour Moss Foundation! Just a mile or so to downtown Southern Pines! Large, well maintained paddocks, a three stall run in shed, a new wash stall and a separate two stall main barn with tack room and storage stall make this farm a joy for both you and your horses! The large storage garage offers 12' clearance which makes it perfect for a horse trailer or RV. The roof is new in 2020. With a split bedroom plan, the home makes it easy to entertain and gives your guests plenty of privacy. The ''mud room'' area is large and is perfect for leaving those riding boots in! Just walk across to the barn and hop on your horse! There are approximately 4 acres of wooded land that could be cleared for more pasture. All acreage is completely flat making it perfect to school your horse or even add a riding ring. Such a lovely horse farm with fabulous Southern Pines Horse Country history! Make it YOURS today... come home to Tops'l Farm!! Please see documents for all recent upgrades and features!

933 Yadkin Rd, Southern Pines

Courtesy of McDevitt Town & Country Properties

Buyer Representative Everything Pines Partners LLC
$1,575,000
3 Beds ⋅ 3 Baths ⋅ 100463450 MLS
Hobby Horse Farm is a charming gem nestled on Youngs Rd in the heart of Southern Pines Horse Country. This exquisite property features spacious living areas, a large kitchen and dining room, and inviting covered porches that open to a flagstone pool and deck—ideal for entertaining. The saltwater pool includes a hot tub, a diving rock, and a tanning ledge, all set within a beautifully landscaped backyard oasis. For the horses, there's a dedicated haven with expansive pastures providing plenty of shade, along with Run-In Sheds for shelter. The main barn boasts three stalls, a tack room, laundry facilities, a wash stall, and ample hay storage. Additionally, there's an auxiliary barn with two stalls, a separate tack room, and a wash area. Convenient, deeded private road access from Clearwater Creek Lane to barn for all your hay and feed delivery needs. Lush pastures, Run-In sheds, and a fenced riding area complete this turnkey farm. Just across Youngs Rd, the 4000+ acre Walthour Moss Foundation offers multiple access points and miles of sandy trails, hunt fences, bridges, and water crossings, perfect for hours of trail riding. Located approximately 2 miles from downtown Southern Pines and 7 miles from the village of Pinehurst.

3305 Youngs Rd, Southern Pines

Courtesy of Better Homes and GardensReal Estate Lifestyle Property Partners/SP

Buyer Representative Better Homes and GardensReal Estate Lifestyle Property Partners/SP
$2,150,000
4 Beds ⋅ 4 Baths ⋅ 100524886 MLS
One of the last opportunities of its kind--47+ acres in the heart of Southern Pines Horse Country. This rare farm combines the charm of a mid-century ranch home with direct equestrian amenities, including an attached 6-stall center aisle barn with tack and feed rooms, keeping your horses just steps away. A second 6-stall center aisle barn features a 1BR/1BA guest apartment, perfect for visitors or staff. Expansive pastures, a shared pond, and a short hack to the 4,000+ acre Walthour Moss Foundation make this property a true equestrian haven. The rolling topography and exceptional privacy are preserved under a land conservation agreement with Three Rivers Land Trust, which not only protects the land's natural beauty but also provides valuable tax benefits for farm owners. While the home and facilities are in need of updates, the potential is extraordinary--ready for someone with the vision to create a truly remarkable Southern Pines estate.

292 Bump A Long Ln, Southern Pines

Courtesy of Better Homes and GardensReal Estate Lifestyle Property Partners/SP
$1,415,000
3 Beds ⋅ 4 Baths ⋅ 743831 MLS
Experience Elevated Living in Southern Pines! Step into a HOME where luxury meets nature. This meticulously designed custom home offers expansive 360° views through floor-to-ceiling windows, immersing you in the serene beauty of Southern Pines. Daily sightings of deer and other wildlife become your routine, providing a tranquil backdrop to your everyday life. Situated in a community renowned for its equestrian culture, this property carries the legacy of its origins as part of a horse farm. The surrounding area boasts a vibrant horse-loving community, reflecting Southern Pines' rich equestrian traditions . Crafted with precision, the home features clean lines and modern aesthetics. The spacious common areas are perfect for entertaining, while the outdoor fireplace on the private back porch offers a cozy retreat for evening relaxation. Whether you're hosting guests or enjoying a quiet night in, the ambiance is both inviting and sophisticated. Designed by the owner, every detail of this home exudes excellence. From the thoughtful layout to the high-quality finishes, it's evident that this residence was built with passion and expertise . In a market where such unique properties are rare, this home stands out as a testament to luxury living intertwined with nature. Don't miss the opportunity to own a piece of Southern Pines' finest real estate.

250 Pine Needles Lane, Southern Pines

Courtesy of LOVE PINES REALTY

Buyer Representative LPT REALTY LLC
$735,000
5 Beds ⋅ 4 Baths ⋅ 731587 MLS
Beautiful downtown SoPines Property provides old world charm with the feel of all the modern conveniences. A main level primary bedroom with a modern bathroom and large closet. The kitchen with gas range, farm sink in the large teak butcher block island, ample counter space and cabinets. The eating area is just off the kitchen in conjunction with another area for gathering/office or den area that leads out to the expansive fenced side yard. The main living area offers a fireplace and cozy area for just relaxing or entertaining. Second level- 4 additional bedrooms, 3 of which are part of the original house with gorgeous hardwood floors and the other bedroom acts as a second-floor primary bedroom with its own bathroom. There is also a large playroom/living area on the second floor as well. There is a basement area that is around 425+/-sq ft along with additional storage space. The home sits on corner lot and offers various parking and entry options.

195 S Ridge Street, Southern Pines

Courtesy of BH&G REAL ESTATE - LIFESTYLE PROPERTY PARTNERS

Buyer Representative BH&G REAL ESTATE - LIFESTYLE PROPERTY PARTNERS
$1,575,000
3 Beds ⋅ 3 Baths ⋅ 730995 MLS
Hobby Horse Farm is a charming gem nestled on Youngs Rd in the heart of Southern Pines Horse Country. This exquisite property features spacious living areas, a large kitchen and dining room, and inviting covered porches that open to a flagstone pool and deck—ideal for entertaining. The saltwater pool includes a hot tub, a diving rock, and a tanning ledge, all set within a beautifully landscaped backyard oasis. For the horses, there's a dedicated haven with expansive pastures providing plenty of shade, along with Run-In Sheds for shelter. The main barn boasts three stalls, a tack room, laundry facilities, a wash stall, and ample hay storage. Additionally, there's an auxiliary barn with two stalls, a separate tack room, and a wash area. Convenient, deeded private road access from Clearwater Creek Lane to barn for all your hay and feed delivery needs. Lush pastures, Run-In sheds, and a fenced riding area complete this turnkey farm. Just across Youngs Rd, the 4000+ acre Walthour Moss Foundation offers multiple access points and miles of sandy trails, hunt fences, bridges, and water crossings, perfect for hours of trail riding. Located approximately 2 miles from downtown Southern Pines and 7 miles from the village of Pinehurst.

3305 Youngs Road, Southern Pines

Courtesy of BH&G REAL ESTATE - LIFESTYLE PROPERTY PARTNERS

Buyer Representative BH&G REAL ESTATE - LIFESTYLE PROPERTY PARTNERS

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