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$895,000
4 Beds 3 Baths 100584261 MLS ACTIVE Status 2,591 SqFt. 1920 Year Built
A rare piece of Southern Pines history, this extraordinary residence is located in the Historic Weymouth District and represents the last remaining portion of what was once a four-lot estate designed in 1920 by noted New York architect George Cooke. Having studied art in Italy, Cooke envisioned the property as a guest residence within his larger estate, which once occupied much of the surrounding land. The main mansion, located on the adjacent property, was lost to a fire in the early 1940s, while the remaining estate structures were eventually removed to accommodate new development, leaving this home as the sole surviving piece of the original compound. Originally built as guest quarters, the home was designed without a kitchen, as meals were prepared in the main residence and delivered by household staff. The basement served as servant quarters, buggy storage, and a tack room. The home also showcased Cooke's personal art collection, complete with hand-painted murals, and welcomed distinguished guests and European dignitaries, making it a significant part of Southern Pines' architectural and cultural heritage. After decades of neglect, the current owners purchased the property in 2016 and embarked on an extensive restoration that thoughtfully preserved its historic character while seamlessly incorporating modern comforts. The home was taken down to the studs and meticulously rebuilt with restoration of the foundation walls and original basement posts and beams, all-new insulation, electrical, plumbing, and drywall completed between 2018 and 2019. Hardwoods throughout the home allow for a clean and easy flow. The beautifully designed custom kitchen and fully remodeled bathrooms were added in 2020, along with a new HVAC system (2020), creating a home that honors its past while meeting today's standards of comfort and functionality. The lower basement level is ideal for a shop with plenty of work space and/or storage. The extensive renovations were completed with such attention to detail that the updated spaces blend naturally with the original architecture, making it difficult to distinguish between old and new. Outside, mature azaleas, established shrubs, and thoughtfully maintained landscaping frame the home, adding seasonal color and complementing its historic setting. This one-of-a-kind residence offers an exceptionally rare opportunity to own a beautifully restored historic home with remarkable provenance and architectural significance. Nestled in one of Southern Pines' most sought-after historic neighborhoods and just a short walk to downtown, it effortlessly blends timeless character, rich history, and modern living.

650 E Indiana Ave, Southern Pines

$511,000
4 Beds 3 Baths 100583907 MLS ACTIVE Status 2,445 SqFt. 2026 Year Built
Welcome to the Elm 2, a beautifully crafted custom home built by trusted builder Legacy Homes, offering timeless design, quality construction, and thoughtful functionality. This 2-story, 2,445 SF residence features 4 bedrooms, 3 full baths, plus a loft, office, and mud room, providing flexible space for today's lifestyle. The open-concept main living area is anchored by a cozy gas fireplace in the family room and flows seamlessly into the kitchen, which boasts granite countertops, center island, pantry, and ample cabinetry--perfect for entertaining and everyday living! The primary suite is conveniently located on the main level, showcasing a trey ceiling and a private en suite with walk-in closet, tiled walk-in shower, and separate water closet. Upstairs offers two additional bedrooms, a full bath, and a spacious loft. Rounded out with a covered back porch, and 2 car garage. Situated in a quiet part of town with no HOA, this home provides peaceful living with a quick commute to Fort Bragg, Pinehurst, and Southern Pines. Enjoy easy access to world-renowned Pinehurst golf, charming downtown shops, dining, and events, and all the lifestyle amenities the Sandhills area has to offer. A perfect blend of comfort, efficiency, and location--this home is a must-see!

430 Hyland Hills Rd, Southern Pines

$880,000
4 Beds 2 Baths 100578609 MLS ACTIVE Status 2,473 SqFt. 1920 Year Built
The Town of Southern Pines has confirmed that this corner lot can be split into two additional buildable lots -- a rare, documented opportunity for a family compound, spec build, or income-producing investment in the heart of Downtown Southern Pines, steps from shops and restaurants. The existing home is a well-maintained 1920 Dutch Colonial Revival, thoughtfully expanded by Butler Constructs while preserving its original scale and character. The main floor flows naturally between a living room with vented gas fireplace, separate dining room, spacious family room, and a cook's eat-in kitchen designed by ASID designer Denis McCullough -- featuring eco-friendly countertops and Bosch appliances that remain with the home. A private main-floor office, a newer mud/laundry room, and a full bath complete the 1,431-square-foot ground level. Upstairs, four bedrooms, a bonus office nook, and a full bath offer peaceful, private space true to the home's 1920 character. A sketch is available illustrating the option to add a primary suite. Outside, a fully fenced patio and garden provide an exceptional, private entertaining space, and the oversized detached garage offers real potential as a workshop, gym, or studio, in addition to housing one car. Whether you're drawn to the character of the existing home, the confirmed development upside, or both -- this is a rare combination in Downtown Southern Pines. A recent home inspection is available with all minor repairs completed.

260 N Ridge St, Southern Pines

$1,499,000
6 Beds 5 Baths 100577823 MLS ACTIVE Status 4,700 SqFt. 2008 Year Built
Custom Beauty in the Heart of Southern Pines! This stunning Craftsman-style home truly has it all! From the gorgeous mahogany double front doors to the incredible custom finishes throughout. Featuring 6 bedrooms, 4.5 baths, beautiful pine plank floors, granite & marble surfaces, travertine and slate baths, plus a dream kitchen opening to a dramatic two-story family room with exposed beams and a full masonry fireplace. The luxurious primary suite is a true retreat with radiant heated floors, steam shower, air-jet soaking tub for two, and custom espresso cabinetry. Upstairs offers additional bedrooms and bonus space, while thoughtful upgrades include three heat pumps, tankless water heaters, Anderson 400 Series windows, and more. And the location? Absolutely unbeatable -- directly across from the beautiful Weymouth Nature Preserve & Equestrian Trails! A rare combination of craftsmanship, character, and location all wrapped into one extraordinary property.

680 N Bethesda Rd, Southern Pines

$525,000
5 Beds 2 Baths 100574105 MLS ACTIVE Status 1,736 SqFt. 1915 Year Built
Extensively renovated home with a private in-ground pool, sunroom, finished basement and fenced backyard just minutes from Downtown Southern Pines. This move-in ready home offers the perfect combination of comfort, space, and entertainment. This home is filled with natural light and features a beautifully updated kitchen, modern finishes throughout, and flexible living areas ideal for today's lifestyle. Step outside to your own private backyard retreat with a sparkling in-ground pool, spacious fenced yard, and plenty of room for relaxing or entertaining family and friends. The finished basement provides additional living space perfect for a media room, home office, gym, or playroom. Conveniently located just minutes from Downtown Southern Pines, shopping, restaurants, golf courses, and everything the area has to offer, this home is a rare opportunity for buyers looking for a truly move-in ready property with exceptional outdoor living.

4084 Youngs Rd, Southern Pines

$499,000
3 Beds 2 Baths 100563447 MLS ACTIVE Status 1,590 SqFt. 1935 Year Built
$6,000 Price Improvement! Welcome home to a hidden treasure in the heart of Downtown Southern Pines! The character and vibe of this 1930's cottage says it all from the original hardwood & brick floors to the craftsmanship of the Heart Pine wood-paneled LR walls, built-ins, rustic wood beams and slate roofs! The detached third-bedroom guest cottage offers a full bath, refrigerator & storage with privacy for family and guests. Perfect space for multipurpose use or an in-law suite! The charming main cottage offers 2 spacious BR's, each with walk in closets. A hallway butler's pantry houses kitchen items and other storage needs. Charming dining room overlooks a landscape filled with delightful seasonal colors and sounds! Outdoor living is an absolute treat on the spacious screened porch with quick access to living, dining and kitchen. Relax by the warmth of a natural gas fireplace, surrounded by cozy Heart Pine wood paneled living room walls. New energy efficient windows are found throughout the home! A secret English garden will delight your senses...where snapdragons keep company with ripening tomatoes on the vine. The home's gardens and lawn are beautifully maintained with an irrigation system throughout the landscape. Original brick lattice fencing frame heritage plantings, flowers and flowering shrubs and trees. Raised planting beds with young plants await summer's bountiful harvest. Enjoy an ever changing backdrop of lovely smells, colors and the sounds of nature from an inviting screened porch. A privacy fence surrounds the landscaped yard and detached storage shed, perfect for garden and/or workshop space. A brick lattice wall anchors the newer brick patio and was created to preserve the character of the original brick lattice fencing. Ample parking includes a circle drive and side parking for both the main & guest cottages! Enjoy all the conveniences of living within the vibrant Downtown community where shopping, restaurants and parks are just minutes away! Call for your personal tour of this unique property today! You'll leave with a feeling of home!

370 E Morganton Rd, Southern Pines

$2,600,000
4 Beds 5 Baths 100559343 MLS ACTIVE Status 4,012 SqFt. 1968 Year Built
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

$739,000
4 Beds 3 Baths 100554344 MLS ACTIVE Status 2,701 SqFt. 2023 Year Built
Beautiful home located in Saddlebrooke at Longleaf Country Club. Awesome location and convenient to Southern Pines and Pinehurst. Very open floor plan with the primary living area on the main level including master bedroom and guest room/office. Large screened in porch overlooking the beautiful landscaping. Very desirable end location with fenced yard. Exquisite finishes include hardwoods throughout, including upstairs, crown molding, stainless steel appliances, newly painted, plantation shutters. Upstairs you will find 2 more large bedrooms and full bath. Huge walk-in storage room. The large two car garage has sealed floor, utility sink with wrap around back splash and pre-wired for EV charging. Encapsulated crawl space and tankless water heater. This is a rare chance to own one of the nicest homes in Saddlebrooke with a prime location! Call today to see it before it gets gone!

500 Pommel Ln, Southern Pines

$749,500
4 Beds 4 Baths 100552733 MLS ACTIVE Status 3,215 SqFt. 1890 Year Built
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

$85,000
100538134 MLS ACTIVE Status
Here's your chance to own a spacious 0.44-acre lot in a highly desirable location just outside the Southern Pines city limits. This property offers the ideal balance of privacy and convenience — with plenty of room to build your dream home while staying close to everything you love about Moore County living. Enjoy an easy drive to downtown Southern Pines, Aberdeen, Sanford, Raleigh, and Ft. Bragg, plus nearby shopping, dining, and recreation. Whether you're ready to build now or hold for future potential, this parcel is a great opportunity in one of the most sought-after areas of the Sandhills. Highlights: 0.44-acre lot — larger than most in-town parcels Great location just outside the city limits Convenient access to major highways and nearby towns Minutes to shopping, dining, and local amenities A wonderful find for anyone seeking space, flexibility, and convenience near the heart of Southern Pines.

Tbd Tbd Yadkin Rd, Southern Pines

$999,000
100501976 MLS ACTIVE Status
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

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