Coming soon 25 Masters Ridge, Southern Pines, NC! This sophisticated home in the highly desirable gated community of Mid South Country Club with luxurious interiors overlooks the 18th golf hole with lake views. 4 BR/4.5BA, 4 Car Garage. Builders personal home attractively priced at just $305. per SF. New hardwoods in master suite, all hardwoods have been refinished (natural oak), also new paint. New photos to be added soon. Main level has open concept, Chef's Kitchen, luxurious Master suite and two additional main level bedrooms with ensuites, Living room, Carolina room, Formal dining room, Breakfast room, Screened in porch, Laundry room and a 4 car garage. Ideal home for Multi-Generational living, large family or corporate retreat. Lower level has a separate exterior entrance, open porch with hot tub, spacious entertainment area including ample room for billiards, media room with room for all. Also a full second kitchen with bar, electric range, microwave, and refrigerator. Private fourth bedroom with ensuite, a study, home gym, hobby room, office/flex space/finished conditioned storage. Garage boasts epoxy floor and custom storage, second floor walkup floored attic can be additional living area if needed. Media/Music room (insulated for sound) has 7 speakers and blue ray technology. Lower level has Superior wall system. Humidifier on main level with dehumidifier on lower level. Whole house surge protection, energy management system and Sonos whole house audio system. Generator operates the majority of the house. Both fireplaces are vented to the exterior, lush fescue lawn, 3 cameras convey also CPI security system. Available for showings by appointment on August 7th to prequalified buyers only.

25 Masters Rdg, Southern Pines

Courtesy of Keller Williams Pinehurst

$880,000

4 Beds ⋅ 2 Baths ⋅ 100578609 MLS

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

Courtesy of Everything Pines Partners LLC

$579,000

3 Beds ⋅ 3 Baths ⋅ 100577106 MLS

Nestled in the peaceful neighborhood of Knollwood Heights, you will find this beautifully renovated all brick bungalow. Set on a spacious lot of over half an acre, this home offers plenty of outdoor space for relaxation and entertainment. Step inside to find an inviting atmosphere accentuated by all new windows that fill the space with natural light. Gorgeous bamboo floors throughout is just one of the many amazing features that have been added. In the living area you will find a wood-burning fireplace for the perfect cozy setting. The heart of the home features a stunning kitchen with nicely designed finishes, making it a delightful space for cooking and gathering. This charming 70's bungalow boasts three bedrooms each with its own private bath, ensuring comfort and privacy for family and guests. The garage has been enclosed to accommodate a laundry room as well as an office/gym area equipped with a mini-split for heating and cooling. This property provides the perfect backdrop for privacy and still is so very close to downtown Southern Pines and the many amazing amenities that this great town offers. Don't miss the opportunity to own this meticulously renovated gem!

355 Serpentine Dr, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative Fore Properties

$790,000

4 Beds ⋅ 3 Baths ⋅ 100574153 MLS

Welcome to 405 N May Street, where the charm of historic downtown Southern Pines meets the comfort and peace of mind of a newer-construction home. Originally built in 2020 by Latitude and meticulously cared for ever since, this residence offers the rare combination of timeless character and modern efficiency, all just a couple of blocks from the heart of one of North Carolina's most beloved small towns. From the moment you arrive, the home's curb appeal sets the tone. Two generous covered front porches, one on each level, invite you to slow down, sip your morning coffee, and wave to neighbors strolling by. They are the kind of porches Southern Pines is famous for, perfect for rocking chairs and unwinding after a day exploring downtown. Step inside to gleaming hardwood floors that flow throughout, paired with gorgeous designer tile selections that elevate every bathroom. The open main level is anchored by a warm living area featuring a natural gas fireplace, ideal for cozy evenings. The kitchen is a show-stopper, complete with a natural gas range any home chef will appreciate, beautiful finishes, and thoughtful flow into the dining and gathering spaces. A first-floor bedroom with private ensuite offers exceptional flexibility, whether for guests, multigenerational living, or a quiet home office. Upstairs, the spacious primary suite is a true sanctuary with a luxurious ensuite and plenty of room to relax. Two additional bedrooms and another full bath complete the upper level, providing ample space for family, guests, or a work-from-home setup. Out back, enjoy your own private retreat. A newly installed hot tub awaits for stargazing soaks, and the yard offers a quiet escape just steps from all the downtown action. Adding to the rare appeal is a true oversized 1 car garage with its own mini split unit. Whether you need secure parking, a workshop, a home gym, or the ultimate man cave, this versatile space delivers something almost unheard of in downtown homes. Modern conveniences add the finishing touches: natural gas service for both the fireplace and kitchen range, plus an energy-efficient tankless water heater for endless hot water on demand. You get architectural charm that complements Southern Pines' historic streetscape paired with the systems and efficiency of a 2020 build, an unbeatable combination. The location is simply unmatched. A short walk to Broad Street puts you minutes from acclaimed restaurants, boutique shopping, coffee shops, breweries, the weekly farmers market, and the lively events that make downtown Southern Pines so special. World-class golf, the Walthour-Moss Foundation, Weymouth Woods, top-rated schools, and easy access to Fort Bragg and the Raleigh-Durham area are all within easy reach. Pull up the map and see just how effortlessly connected this location is to everything that makes life in the Sandhills so wonderful. Homes of this caliber, in this location, with this level of care and these rare features, do not come along often. 405 N May Street is your chance to step into the Southern Pines lifestyle in a home built for the way you want to live.

405 N May St, Southern Pines

Courtesy of Everything Pines Partners LLC

Buyer Representative Pineland Property Group LLC

$525,000

5 Beds ⋅ 2 Baths ⋅ 100574105 MLS

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

Courtesy of Compass Carolinas LLC

$700,000

4 Beds ⋅ 5 Baths ⋅ LP754467 MLS

Discover exceptional living in this impressive 4-bedroom, 3-bath, 2-half-bath home located in the highly desirable community of Southern Pines, NC. Offering 4,500 square feet of beautifully designed living space, this residence combines luxury, comfort, and modern convenience. The kitchen features stainless steel appliances, a gas range, granite countertops, a spacious kitchen island, and abundant storage—perfect for both everyday cooking and entertaining. Hardwood floors and tile flow throughout the main level, leading to a warm and inviting living area accented by a gas fireplace. The main level includes a generous primary suite with garden tub and walk in shower. Upstairs, has the additional 3 bedrooms and a large loft, providing comfort and flexibility for family, guests, or home office needs. A highlight of this home is the large finished walk-out basement, providing valuable additional living space perfect for a media room, home gym, or recreation area, offering endless versatility for your lifestyle. Step outside to a private, fully fenced backyard complete with a deck and charming pergola, creating the ideal setting for outdoor dining, relaxation, and gatherings. With its spacious layout, upgraded features, and prime Southern Pines location, this home is truly a must-see.

575 S Valley Rd, Southern Pines

Seller Representative EVERYTHING PINES COMMERCIAL

Buyer Representative

$950,000

3 Beds ⋅ 3 Baths ⋅ LP748136 MLS

NO HOA! Large Corner Lot + Dream Garage Just minutes from McDeeds Creek Elementary or a golf cart ride away from Pine Needles Lodge & Golf Club and Mid Pines Inn, this custom-built Craftsman/Modern Farmhouse offers the perfect blend of charm and convenience in Southern Pines. Enjoy an open-concept layout with vaulted ceilings, hardwood floors, shiplap accents, and custom built-ins throughout. The chef's kitchen features GE Cafe appliances, a 36'' dual fuel range, quartz countertops, and a hidden walk-in pantry. The private main-level primary suite includes TWO oversized 12'x8' walk-in closets. Upstairs offers two spacious bedrooms, each with walk-in closets, and a stylish dual-sink bathroom. Step outside to a beautifully landscaped yard featuring lush Zeon Zoysia sod with full irrigation and a cobblestone-edged bluestone driveway. Hidden exterior soffit lighting showcases the home's architecture after dark and ensures you never come home to a dark entry. Just off the main living area, a private covered porch leads to a circular patio with bistro lighting, creating a warm and inviting outdoor living space. The detached 1,200 SqFt (40'x30') three-car garage features epoxy flooring, large 10'x10' insulated doors, a center bay drain, hot and cold water hookups, and a side-entry golf cart door - perfect for car enthusiasts or hobbyists. Upstairs, a spacious UNFINISHED 600 SqFt (40'x15') storage room offers flexible potential for a home gym, studio, office, or additional storage. Full features list available in documents. Schedule your showing today!

175 Longleaf Rd, Southern Pines

Seller Representative CAROLINA PROPERTY SALES

Buyer Representative

$950,000

3 Beds ⋅ 3 Baths ⋅ 10114088 MLS

NO HOA! Large Corner Lot + Dream Garage Just minutes from McDeeds Creek Elementary or a golf cart ride away from Pine Needles Lodge & Golf Club and Mid Pines Inn, this custom-built Craftsman/Modern Farmhouse offers the perfect blend of charm and convenience in Southern Pines. Enjoy an open-concept layout with vaulted ceilings, hardwood floors, shiplap accents, and custom built-ins throughout. The chef's kitchen features GE Cafe appliances, a 36'' dual fuel range, quartz countertops, and a hidden walk-in pantry. The private main-level primary suite includes TWO oversized 12'x8' walk-in closets. Upstairs offers two spacious bedrooms, each with walk-in closets, and a stylish dual-sink bathroom. Step outside to a beautifully landscaped yard featuring lush Zeon Zoysia sod with full irrigation and a cobblestone-edged bluestone driveway. Hidden exterior soffit lighting showcases the home's architecture after dark and ensures you never come home to a dark entry. Just off the main living area, a private covered porch leads to a circular patio with bistro lighting, creating a warm and inviting outdoor living space. The detached 1,200 SqFt (40'x30') three-car garage features epoxy flooring, large 10'x10' insulated doors, a center bay drain, hot and cold water hookups, and a side-entry golf cart door - perfect for car enthusiasts or hobbyists. Upstairs, a spacious UNFINISHED 600 SqFt (40'x15') storage room offers flexible potential for a home gym, studio, office, or additional storage. Full features list available in documents. Schedule your showing today!

175 Longleaf Rd, Southern Pines

Seller Representative Carolina Property Sales

Buyer Representative

$1,250,000

6 Beds ⋅ 4 Baths ⋅ LP730361 MLS

Welcome to your dream home in the coveted gated community of Mid South Club! With its spacious open floor plan and high-end finishes, this custom home is designed for modern living and entertaining. The heart of this home is the chef's kitchen, featuring a top-of-the-line Wolf 5-burner gas range, custom cabinetry, and leathered finish granite countertops. The main level also boasts a luxurious primary suite with a cozy gas fireplace and spacious walk-in closet. Three additional bedrooms on this level offer flexibility for guests, family, or home office space. The fully finished walk-out basement is an entertainer's dream. It includes a large space for a home gym, a 6-person steam sauna, an indoor in-ground 16 ft ACON trampoline, and two additional bedrooms with a convenient full bathroom. With its prime location, luxurious features, and elegant design, this property is a rare find! Schedule your private tour today and discover the lifestyle you've always dreamed of in Mid South Club.

54 Plantation Dr, Southern Pines

Seller Representative EVERYTHING PINES PARTNERS (SANFORD)

Buyer Representative

$1,075,000

4 Beds ⋅ 4 Baths ⋅ 100572642 MLS

Tucked away on a beautifully landscaped and private almost 1-acre lot in one of Southern Pines' most desirable neighborhoods, this stunning all-brick 1955 ranch perfectly blends timeless mid-century modern design with thoughtful modern updates. Surrounded by mature pines and just minutes from downtown Southern Pines, this property offers a rare combination of character, space, and resort-style outdoor living. Inside, you'll find light-filled living spaces, clean architectural lines, and an effortlessly stylish aesthetic throughout. The spacious layout includes a walk-out lower level featuring a large recreation room, full bathroom, additional bedroom, and laundry area, ideal for guests, multigenerational living, a home gym, or flexible bonus space. Step outside to your own private retreat complete with an inground pool, fenced backyard, sauna, screened porch, and multiple outdoor entertaining areas all designed to take full advantage of the serene setting. A gated driveway adds both privacy and curb appeal to this truly one-of-a-kind Southern Pines property.

565 S Valley Rd, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative Everything Pines Partners LLC

$560,000

3 Beds ⋅ 4 Baths ⋅ 100569098 MLS

Tucked away on a private lot framed by towering pines and bursts of blooming azaleas, this two-level home offers the kind of peaceful retreat that's increasingly hard to find -- all while sitting just minutes from the charm of Southern Pines, the world-class golf of Pinehurst, and the convenience of Fort Bragg and Camp Mackall. From the moment you arrive, the natural beauty of the property sets the tone. A fully fenced backyard provides privacy and room to roam, while a beautiful back deck invites you to linger over morning coffee or evening gatherings surrounded by the sights and sounds of nature. Inside, the main level delivers comfortable, well-appointed living. The kitchen is a true standout -- cabinetry stretches all the way to the ceiling, granite countertops provide ample workspace, and a gas stove with double oven makes entertaining a pleasure. A newer refrigerator rounds out this thoughtfully equipped space. The main level also offers a generous pantry, dedicated laundry, and flows naturally through the living and dining areas into a sun-drenched sunroom -- the perfect spot to take in the lush surroundings year round. The primary suite is your private sanctuary, complete with a stunning clawfoot tub and separate shower. A second bedroom and full bath complete the main floor. Head downstairs and discover a walkout lower level that truly expands your living options. Engineered hardwood floors, classic paneling, and a light-filled four-seasons room create a warm and welcoming atmosphere. A spacious family room, third bedroom, and a large recreation room offer incredible flexibility -- whether you need a home gym, hobby space, playroom, or all three. A lower-level bathroom features charming vintage tile and a new countertop, ready for your personal finishing touches. Additional highlights include a dual-zoned HVAC system (replaced 2018), new gutters, a leased propane tank through Amerigas, and a storage shed set on a concrete slab. Every detail has been considered to make this home as functional as it is inviting. Whether you're seeking privacy, space, or easy access to everything the Sandhills has to offer, 852 Barber Road checks every box.

852 Barber Rd, Southern Pines

Courtesy of Everything Pines Partners LLC

Buyer Representative Keller Williams Pinehurst

$608,000

4 Beds ⋅ 3 Baths ⋅ 100553996 MLS

EASY Commute to FT Bragg, this stunning 4-bedroom, 3-bath home with basement bonus space is situated on over half an acre, offering space, functionality, and refined finishes throughout. The open-concept main living area is designed for both everyday comfort and entertaining, featuring stainless steel appliances, quartz countertops, a large center island, and waterproof Pergo flooring across the primary living spaces. Abundant natural light enhances the seamless flow between the kitchen, dining, and living areas. The spacious primary suite provides a private retreat with dual vanities, a glass-enclosed walk-in shower, and an oversized walk-in closet. Secondary bedrooms are generously sized with ample storage. The fully finished downstairs walk-out level offers exceptional flexibility -- ideal for a separate living quarters, in-law suite, or private guest space. Complete with a kitchenette, full bath, and additional flex room, it can easily function as a family recreation area, home office, gym, or apartment-style setup. Enjoy the privacy of a large lot while still benefiting from a convenient commute to Ft. Bragg and being just minutes from downtown Southern Pines with dining, boutique shopping, and vibrant nightlife. This property delivers the perfect balance of comfort, versatility, and location -- truly a must-see. Many of the furnishings can be sold separately from the sale of the home.

180 One Down St, Southern Pines

Courtesy of Carolina Property Sales

Buyer Representative Pineland Property Group LLC

$799,000

4 Beds ⋅ 3 Baths ⋅ 100547937 MLS

Welcome to 335 E Connecticut Avenue, a rare opportunity to own a piece of Southern Pines history while enjoying the ultimate walkable lifestyle. This distinguished Dutch Colonial, built circa 1920 and listed on the National Register of Historic Places, sits in the heart of downtown Southern Pines—steps from charming wine bars, cocktail lounges, coffee shops, the library, and all the amenities that make small-town living so desirable. The home's thoughtfully preserved interior spans 2,312 heated square feet across three levels, with historic details lovingly maintained throughout. The first floor features a beautifully updated kitchen with new appliances (including natural gas stove!) and ample storage, a formal dining room with French doors, and a living room with decorative fireplace. The show-stopping main level primary suite offers exposed beams, a chandelier, walk-in closet, and stunning ensuite bathroom with clawfoot tub. Three additional bedrooms and another clawfoot tub bath occupy the upper level, while a first-floor half bath and charming herringbone brick mudroom complete the main living spaces. The versatility continues beyond the main house. The partially finished lower level provides 311 square feet of heated and cooled space—perfect for a media room, playroom, or home office—plus laundry and unfinished storage. Outside, a charming brick front path leads to a covered porch, while a brick side patio and large sunny deck, offering afternoon and evening shade and overlooking the low-maintenance turf backyard. The crown jewel is the detached 321-square-foot heated and cooled building, currently a gym but equally suited as a home office or sunny studio. Recent upgrades include foundation waterproofing, new appliances, fresh paint, new doors, window treatments, deck refresh, roof repairs, and an EV charger. Walk to everything while enjoying your private historic sanctuary.

335 E Connecticut Ave, Southern Pines

Courtesy of Everything Pines Partners LLC

Buyer Representative Everything Pines Partners LLC

$700,000

4 Beds ⋅ 5 Baths ⋅ 754467 MLS

Discover exceptional living in this impressive 4-bedroom, 3-bath, 2-half-bath home located in the highly desirable community of Southern Pines, NC. Offering 4,500 square feet of beautifully designed living space, this residence combines luxury, comfort, and modern convenience. The kitchen features stainless steel appliances, a gas range, granite countertops, a spacious kitchen island, and abundant storage—perfect for both everyday cooking and entertaining. Hardwood floors and tile flow throughout the main level, leading to a warm and inviting living area accented by a gas fireplace. The main level includes a generous primary suite with garden tub and walk in shower. Upstairs, has the additional 3 bedrooms and a large loft, providing comfort and flexibility for family, guests, or home office needs. A highlight of this home is the large finished walk-out basement, providing valuable additional living space perfect for a media room, home gym, or recreation area, offering endless versatility for your lifestyle. Step outside to a private, fully fenced backyard complete with a deck and charming pergola, creating the ideal setting for outdoor dining, relaxation, and gatherings. With its spacious layout, upgraded features, and prime Southern Pines location, this home is truly a must-see.

575 S Valley Road, Southern Pines

Courtesy of EVERYTHING PINES COMMERCIAL

Buyer Representative NEXTHOME IN THE PINES

$700,000

4 Beds ⋅ 5 Baths ⋅ 100544807 MLS

Discover exceptional living in this impressive 4-bedroom, 3-bath, 2-half-bath home located in the highly desirable community of Southern Pines, NC. Offering 4,500 square feet of beautifully designed living space, this residence combines luxury, comfort, and modern convenience. The kitchen features stainless steel appliances, a gas range, granite countertops, a spacious kitchen island, and abundant storage—perfect for both everyday cooking and entertaining. Hardwood floors and tile flow throughout the main level, leading to a warm and inviting living area accented by a gas fireplace. The main level includes a generous primary suite with garden tub and walk in shower. Upstairs, has the additional 3 bedrooms and a large loft, providing comfort and flexibility for family, guests, or home office needs. A highlight of this home is the large finished walk-out basement, providing valuable additional living space perfect for a media room, home gym, or recreation area, offering endless versatility for your lifestyle. Step outside to a private, fully fenced backyard complete with a deck and charming pergola, creating the ideal setting for outdoor dining, relaxation, and gatherings. With its spacious layout, upgraded features, and prime Southern Pines location, this home is truly a must-see.

575 S Valley Rd, Southern Pines

Courtesy of Everything Pines Commercial

Buyer Representative Nexthome In The Pines

$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

$480,000

3 Beds ⋅ 3 Baths ⋅ 100535171 MLS

Live the life you've been imagining in this charming two-story home perfectly positioned in the heart of downtown Southern Pines. Just a few blocks from all the action, you'll enjoy the rare luxury of walking to everything that makes this community special - grab a glass of wine at a local favorite, hit the gym without getting in your car, stroll to First Fridays, or browse the farmers market on Saturday mornings. This is the walkable lifestyle Southern Pines is famous for, right at your doorstep. Step onto the inviting front porch - your future favorite spot for morning coffee - and into an open floor plan that's perfect for modern living. Soaring vaulted ceilings in the living room create an airy, spacious feel, while the kitchen delivers on function with abundant storage, a gas range for the home chef, and a recently replaced dishwasher. The generously sized laundry room (complete with shelf storage) is the kind of practical luxury you'll appreciate every single week. The thoughtfully designed first-floor primary suite means easy living with no stairs required. You'll love the ensuite bathroom featuring a tiled shower and double vanity, plus a convenient door leading directly to your private, fenced backyard - imagine summer mornings with your coffee outside or letting the dogs out without walking through the house. Upstairs, two additional bedrooms share a Jack and Jill bathroom, providing comfort and privacy for family, guests, or a home office setup. The backyard is where lifestyle truly shines: a fenced yard for peace of mind, a back porch for relaxing, and the perfect spot for a firepit where you'll create memories during cozy fall evenings with friends and family. This is more than a house - it's your gateway to the Southern Pines lifestyle you deserve, where convenience meets charm and value meets location. Welcome home.

415 W Vermont Ave, Southern Pines

Courtesy of Everything Pines Partners LLC

Buyer Representative Pineland Property Group LLC

$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

$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

$440,000

3 Beds ⋅ 3 Baths ⋅ 100468808 MLS

Welcome to your dream home, just moments from downtown Southern Pines! Step inside this 3 bedroom, 2.5 bathroom home to discover an inviting open floor plan, a bright kitchen with stainless steel appliances and granite countertops, and a cozy living area perfect for gathering around the fireplace. Enjoy relaxing on the charming covered front porch, or on the rear covered deck where you can look out over your fenced backyard. The detached garage provides ample opportunity for not only vehicle storage, but a home gym, workshop, craft or office space. The master suite offers a private oasis with an en-suite bathroom - a perfect escape at the end of the day. With additional bedrooms that can serve as guest rooms, a home office, or even a play room, there's plenty of space for everyone. Community pool, playground, clubhouse access, and lawn maintenance provided in HOA dues. Photos after floor plans are of community amenities. Located just minutes from downtown Southern Pines, you'll have easy access to charming shops, delightful restaurants, and beautiful parks. Plus, the area's rich history and vibrant community make it a wonderful place to call home. Don't miss your chance to own this stunning property—schedule a showing today and experience the charm of Southern Pines living!

1135 N May St, Southern Pines

Courtesy of Everything Pines Partners LLC

Buyer Representative Everything Pines Partners LLC

$1,250,000

6 Beds ⋅ 4 Baths ⋅ 100454914 MLS

Welcome to your dream home in the coveted gated community of Mid South Club! With its spacious open floor plan and high-end finishes, this custom home is designed for modern living and entertaining. The heart of this home is the chef's kitchen, featuring a top-of-the-line Wolf 5-burner gas range, custom cabinetry, leathered finish granite countertops, and a large island with seating. Whether you're preparing a gourmet meal or a casual breakfast, this eat-in kitchen has everything you need. The main level also boasts a luxurious primary suite with a cozy gas fireplace and spacious walk-in closet. Three additional bedrooms on this level offer flexibility for guests, family, or home office space. The fully finished walk-out basement is an entertainer's dream. It includes a large space for a home gym, a 6-person steam sauna, an indoor in-ground 16 ft ACON trampoline, and two additional bedrooms with a convenient full bathroom. This space is perfect for hosting gatherings or enjoying family fun! Step outside to your private patio, where you can unwind by the gas fire pit or soak in the Hot Spring Spas hot tub. Situated on the golf course, this home offers stunning views of the driving range and practice green. This outdoor living space is designed for relaxation and year-round enjoyment. With its prime location, luxurious features, and elegant design, this property is a rare find! Schedule your private tour today and discover the lifestyle you've always dreamed of in Mid South Club.

54 Plantation Dr, Southern Pines

Courtesy of LPT Realty

Buyer Representative Carolina Property Sales

$950,000

3 Beds ⋅ 3 Baths ⋅ 100523312 MLS

NO HOA! Large Corner Lot + Dream Garage Just minutes from McDeeds Creek Elementary or a golf cart ride away from Pine Needles Lodge & Golf Club and Mid Pines Inn, this custom-built Craftsman/Modern Farmhouse offers the perfect blend of charm and convenience in Southern Pines. Enjoy an open-concept layout with vaulted ceilings, hardwood floors, shiplap accents, and custom built-ins throughout. The chef's kitchen features GE Cafe appliances, a 36'' dual fuel range, quartz countertops, and a hidden walk-in pantry. The private main-level primary suite includes TWO oversized 12'x8' walk-in closets. Upstairs offers two spacious bedrooms, each with walk-in closets, and a stylish dual-sink bathroom. Step outside to a beautifully landscaped yard featuring lush Zeon Zoysia sod with full irrigation and a cobblestone-edged bluestone driveway. Hidden exterior soffit lighting showcases the home's architecture after dark and ensures you never come home to a dark entry. Just off the main living area, a private covered porch leads to a circular patio with bistro lighting, creating a warm and inviting outdoor living space. The detached 1,200 SqFt (40'x30') three-car garage features epoxy flooring, large 10'x9' insulated doors, a center bay drain, hot and cold water hookups, and a side-entry golf cart door - perfect for car enthusiasts or hobbyists. Upstairs, a spacious UNFINISHED 600 SqFt (40'x15') storage room offers flexible potential for a home gym, studio, office, or additional storage. Full features list available in documents. Schedule your showing today!

175 Longleaf Rd, Southern Pines

Courtesy of Carolina Property Sales

Buyer Representative A Non Member

$605,000

4 Beds ⋅ 4 Baths ⋅ 100500272 MLS

Nestled in the desirable Sandhurst South neighborhood of Southern Pines, this exceptional all-brick home offers the perfect blend of space, comfort, and convenience. With 2,829 square feet of thoughtfully designed living space, this well-maintained property is ideal for both everyday living and entertaining. Enjoy a quick commute to Fort Bragg and just a 5-minute drive to downtown Southern Pines, with the natural beauty of Weymouth Woods close by. The timeless all-brick exterior provides curb appeal while requiring minimal maintenance. Vehicle storage is abundant with both a 2-car attached garage and a 1-car detached garage, perfect for car enthusiasts, a gym, or additional storage. The spacious fenced backyard creates a private outdoor retreat perfect for pets, gardening, or family gatherings, while the inviting back deck offers an ideal space for al fresco dining and relaxation. Inside, the thoughtful floor plan features a first-floor primary bedroom suite complete with a large bathroom and walk-in closet. Formal dining space allows for elegant entertaining, while the cozy breakfast nook provides the perfect spot for casual meals. Upstairs, you'll find a versatile loft area and three additional bedrooms, including one ensuite, offering plenty of space for family or guests. Storage is never a concern with the large walk-in attic. This lovingly maintained home offers both functionality and charm in one of Southern Pines' most sought-after neighborhoods. Don't miss your opportunity to make this exceptional property your new home!

230 W Hedgelawn Way, Southern Pines

Courtesy of Everything Pines Partners LLC

Buyer Representative LPT Realty

$569,900

4 Beds ⋅ 4 Baths ⋅ 100458385 MLS

This beautiful home at the Arboretum offers community amenities, including a pool, clubhouse, playground, and gym facilities. With a large open living space, formal dining room, an amazing kitchen island, granite countertops, gas stove, fireplace, a tankless water heater and natural gas. Rare 3- and one-half bathrooms, 4 bedrooms with primary and 2 additional on the main level. 4th bedroom with full bath upstairs for a private space. With a covered porch, nice fenced in back yard and garage make this low maintenance home close to everything Pinehurst and Southern Pines has to offer, a perfect home.

350 N Bracken Fern Ln, Southern Pines

Courtesy of Lynette Williams Real Estate LLC

Buyer Representative Pines Sotheby's International Realty

$410,000

3 Beds ⋅ 3 Baths ⋅ 100485187 MLS

Built in 2018, this beautiful two-story home combines the convenience of a prime downtown location and price! The open-concept design on the main level creates an inviting space for modern living, featuring a sunlit Kitchen, Dining, and Living area—perfect for hosting friends and family. Highlights include solid surface flooring, granite countertops throughout, a spacious pantry, and a handy half bath. The upper level offers three generously sized bedrooms, a loft area for added flexibility, and ceramic tile flooring in the bathrooms and laundry room. All new carpet as well throughout the entire second floor. The fully fenced backyard includes a deck, patio, and fire-pit area—a private outdoor haven ideal for relaxing or entertaining. The two-car garage provides ample storage or the perfect place for your cars and gym! Ideally situated just moments from the lively restaurants, charming local shops, scenic parks, and recreational amenities of downtown Southern Pines, this home offers the perfect combination of convenience and lifestyle!

426 W Illinois Ave, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative Old Glory Realty LLC

$950,000

3 Beds ⋅ 3 Baths ⋅ 748136 MLS

NO HOA! Large Corner Lot + Dream Garage Just minutes from McDeeds Creek Elementary or a golf cart ride away from Pine Needles Lodge & Golf Club and Mid Pines Inn, this custom-built Craftsman/Modern Farmhouse offers the perfect blend of charm and convenience in Southern Pines. Enjoy an open-concept layout with vaulted ceilings, hardwood floors, shiplap accents, and custom built-ins throughout. The chef's kitchen features GE Cafe appliances, a 36'' dual fuel range, quartz countertops, and a hidden walk-in pantry. The private main-level primary suite includes TWO oversized 12'x8' walk-in closets. Upstairs offers two spacious bedrooms, each with walk-in closets, and a stylish dual-sink bathroom. Step outside to a beautifully landscaped yard featuring lush Zeon Zoysia sod with full irrigation and a cobblestone-edged bluestone driveway. Hidden exterior soffit lighting showcases the home's architecture after dark and ensures you never come home to a dark entry. Just off the main living area, a private covered porch leads to a circular patio with bistro lighting, creating a warm and inviting outdoor living space. The detached 1,200 SqFt (40'x30') three-car garage features epoxy flooring, large 10'x10' insulated doors, a center bay drain, hot and cold water hookups, and a side-entry golf cart door - perfect for car enthusiasts or hobbyists. Upstairs, a spacious UNFINISHED 600 SqFt (40'x15') storage room offers flexible potential for a home gym, studio, office, or additional storage. Full features list available in documents. Schedule your showing today!

175 Longleaf Road, Southern Pines

Courtesy of CAROLINA PROPERTY SALES

Buyer Representative ONNIT REALTY GROUP

$1,250,000

6 Beds ⋅ 4 Baths ⋅ 730361 MLS

Welcome to your dream home in the coveted gated community of Mid South Club! With its spacious open floor plan and high-end finishes, this custom home is designed for modern living and entertaining. The heart of this home is the chef's kitchen, featuring a top-of-the-line Wolf 5-burner gas range, custom cabinetry, and leathered finish granite countertops. The main level also boasts a luxurious primary suite with a cozy gas fireplace and spacious walk-in closet. Three additional bedrooms on this level offer flexibility for guests, family, or home office space. The fully finished walk-out basement is an entertainer's dream. It includes a large space for a home gym, a 6-person steam sauna, an indoor in-ground 16 ft ACON trampoline, and two additional bedrooms with a convenient full bathroom. With its prime location, luxurious features, and elegant design, this property is a rare find! Schedule your private tour today and discover the lifestyle you've always dreamed of in Mid South Club.

54 Plantation Drive, Southern Pines

Courtesy of LPT REALTY LLC

Buyer Representative CAROLINA PROPERTY SALES

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