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$567,000
3 Beds ⋅ 2 Baths ⋅ LP763104 MLS
Charming cottage in the heart of downtown Southern Pines, complete with a detached apartment and an oversized in-town lot. The main home offers 1,341 square feet with three bedrooms and two full bathrooms, while the separate 664-square-foot apartment features one bedroom and one full bath, ideal for guests, a private retreat, or income-producing potential. Full of classic Southern Pines charm, this inviting property welcomes you with cheerful yellow siding and a timeless white picket fence. Inside, the main cottage features a bright, open living and kitchen area with a breakfast bar, dedicated dining space, and a cozy enclosed front porch that is perfect for morning coffee or relaxing in the evening. The main level includes two guest bedrooms and a full bath with a charming clawfoot tub, while the private primary suite is tucked upstairs with its own full bath. Outside, a spacious patio nestled between the main home and apartment creates the perfect setting for entertaining, complete with a large pergola and fire pit. The detached apartment includes its own kitchen, living area, private bedroom, and full bath, offering excellent flexibility and privacy. Beautiful renovations paired with original character, highlighted by classic brick details and rich wood flooring, create a warm and inviting atmosphere. This one-of-a-kind downtown property is a rare find.

745 N May St, Southern Pines

Seller Representative EVERYTHING PINES PARTNERS LLC

Buyer Representative

$567,000
3 Beds ⋅ 2 Baths ⋅ 763104 MLS
Charming cottage in the heart of downtown Southern Pines, complete with a detached apartment and an oversized in-town lot. The main home offers 1,341 square feet with three bedrooms and two full bathrooms, while the separate 664-square-foot apartment features one bedroom and one full bath, ideal for guests, a private retreat, or income-producing potential. Full of classic Southern Pines charm, this inviting property welcomes you with cheerful yellow siding and a timeless white picket fence. Inside, the main cottage features a bright, open living and kitchen area with a breakfast bar, dedicated dining space, and a cozy enclosed front porch that is perfect for morning coffee or relaxing in the evening. The main level includes two guest bedrooms and a full bath with a charming clawfoot tub, while the private primary suite is tucked upstairs with its own full bath. Outside, a spacious patio nestled between the main home and apartment creates the perfect setting for entertaining, complete with a large pergola and fire pit. The detached apartment includes its own kitchen, living area, private bedroom, and full bath, offering excellent flexibility and privacy. Beautiful renovations paired with original character, highlighted by classic brick details and rich wood flooring, create a warm and inviting atmosphere. This one-of-a-kind downtown property is a rare find.

745 N May Street, Southern Pines

Courtesy of EVERYTHING PINES PARTNERS LLC

Buyer Representative EVERYTHING PINES PARTNERS LLC
$585,000
4 Beds ⋅ 3 Baths ⋅ 100575866 MLS
Built in 2023 and better than new, this stunning 4-bedroom, 3-bath home is tucked away on a quiet cul-de-sac in a beautiful neighborhood just minutes from Southern Pines and the Weymouth Trailhead. Thoughtfully designed with both comfort and functionality in mind, the main floor features a spacious flex room and private study--perfect for a home office, playroom, or guest space. The open-concept kitchen is the heart of the home, showcasing a large center island, abundant cabinetry, and an oversized pantry ideal for storage and entertaining. Upstairs, the luxurious primary suite offers a spa-like bath and generous walk-in closet. Step outside to enjoy the back deck and patio overlooking raised flower beds and a peaceful backyard setting. With modern finishes, like-new construction, and an unbeatable location near shopping, dining, and outdoor recreation, this home offers the perfect blend of style, convenience, and tranquility.

710 Hayworth Ct, Southern Pines

Courtesy of Maison Realty Group
$550,000
2 Beds ⋅ 2 Baths ⋅ 100575692 MLS ⋅ Mid South Club BLDG.
LOCK IT AND LEAVE IT LIFESTYLE! Gorgeous golf front condo located in the prestigious Mid South Club! Rare opportunity to find this duplex location available in Camden Villas with panoramic views of the 8th fairway of the Arnold Pamer Signature golf course. All one floor living featuring split bedroom floor plan, large living room and dining room combination, Carolina Room PLUS a den or office. and a two-car garage. This very popular Canterbury floor plan is beautifully maintained. All appliances, including washer and dryer, will remain. Please see Upgrades list in attached documents for improvements made to this beautiful home. The monthly dues for Camden Villas include the use of the CV clubhouse which features an entertainment room with pool table, kitchen and fitness room. The very comprehensive dues also include master insurance, professional management/accounting, landscaping, irrigation, termite bond, gutter cleaning, exterior painting, power washing the exterior and roof repairs! The Mid South POA dues include security, front gate, road maintenance, internet and cable TV. A transferable Mid-Tal membership gives access to Mid South Club, Talamore Golf Club and Legacy Golf Club. Great amenities include clubhouses, swimming pools, tennis courts and premier golf courses. Buyer to pay prevailing costs. This beautiful home won't last long! Call today!

109 Essex Pl, Southern Pines

Courtesy of Mary M. Wilson-Wittenstrom
$595,000
3 Beds ⋅ 3 Baths ⋅ LP762976 MLS
Tucked within the private, gated community of Mid South Club, this beautifully appointed Camden Villas residence blends timeless elegance with effortless comfort. The sought-after Canterbury floor plan offers an open, airy layout enhanced by soaring cathedral ceilings, rich hardwood flooring, recessed lighting, and thoughtfully designed living spaces throughout. A sunlit flex room wrapped in windows and a refined study with dramatic arched detailing provide ideal spaces for relaxing or working from home. At the heart of the home, the stunning kitchen showcases dark-stained custom cabinetry with glass display accents, under-cabinet lighting, granite countertops, decorative tile backsplash, stainless steel appliances, a breakfast bar, skylight, and tile flooring -- all opening seamlessly to the main living and dining areas. The inviting living room is anchored by a beautiful gas fireplace with elegant tile surround and custom millwork accents. The spacious primary suite features cathedral ceilings, a walk-in closet, and a luxurious bath complete with dual vanities, granite finishes, and a beautifully tiled walk-in shower. A private guest suite on the main level and an expansive upstairs bonus room with its own full bath provide exceptional flexibility for guests or additional living space. Outdoor living is equally impressive with a charming brick patio, stone wall accents, and a natural gas fire pit overlooking the beautifully landscaped grounds. Ideally situated just across from the Camden Villas clubhouse with fitness center and gathering spaces, this move-in-ready home also offers a transferable membership to Mid South Club and Talamore Golf Resort for an exceptional lifestyle experience.

107 W Chelsea Ct, Southern Pines

Seller Representative MEESE PROPERTY GROUP
$595,000
3 Beds ⋅ 3 Baths ⋅ 762976 MLS
Tucked within the private, gated community of Mid South Club, this beautifully appointed Camden Villas residence blends timeless elegance with effortless comfort. The sought-after Canterbury floor plan offers an open, airy layout enhanced by soaring cathedral ceilings, rich hardwood flooring, recessed lighting, and thoughtfully designed living spaces throughout. A sunlit flex room wrapped in windows and a refined study with dramatic arched detailing provide ideal spaces for relaxing or working from home. At the heart of the home, the stunning kitchen showcases dark-stained custom cabinetry with glass display accents, under-cabinet lighting, granite countertops, decorative tile backsplash, stainless steel appliances, a breakfast bar, skylight, and tile flooring -- all opening seamlessly to the main living and dining areas. The inviting living room is anchored by a beautiful gas fireplace with elegant tile surround and custom millwork accents. The spacious primary suite features cathedral ceilings, a walk-in closet, and a luxurious bath complete with dual vanities, granite finishes, and a beautifully tiled walk-in shower. A private guest suite on the main level and an expansive upstairs bonus room with its own full bath provide exceptional flexibility for guests or additional living space. Outdoor living is equally impressive with a charming brick patio, stone wall accents, and a natural gas fire pit overlooking the beautifully landscaped grounds. Ideally situated just across from the Camden Villas clubhouse with fitness center and gathering spaces, this move-in-ready home also offers a transferable membership to Mid South Club and Talamore Golf Resort for an exceptional lifestyle experience.

107 W Chelsea Court, Southern Pines

Courtesy of MEESE PROPERTY GROUP
$595,000
3 Beds ⋅ 3 Baths ⋅ 100575585 MLS
Tucked within the private, gated community of Mid South Club, this beautifully appointed Camden Villas residence blends timeless elegance with effortless comfort. The sought-after Canterbury floor plan offers an open, airy layout enhanced by soaring cathedral ceilings, rich hardwood flooring, recessed lighting, and thoughtfully designed living spaces throughout. A sunlit flex room wrapped in windows and a refined study with dramatic arched detailing provide ideal spaces for relaxing or working from home. At the heart of the home, the stunning kitchen showcases dark-stained custom cabinetry with glass display accents, under-cabinet lighting, granite countertops, decorative tile backsplash, stainless steel appliances, a breakfast bar, skylight, and tile flooring -- all opening seamlessly to the main living and dining areas. The inviting living room is anchored by a beautiful gas fireplace with elegant tile surround and custom millwork accents. The spacious primary suite features cathedral ceilings, a walk-in closet, and a luxurious bath complete with dual vanities, granite finishes, and a beautifully tiled walk-in shower. A private guest suite on the main level and an expansive upstairs bonus room with its own full bath provide exceptional flexibility for guests or additional living space. Outdoor living is equally impressive with a charming brick patio, stone wall accents, and a natural gas fire pit overlooking the beautifully landscaped grounds. Ideally situated just across from the Camden Villas clubhouse with fitness center and gathering spaces, this move-in-ready home also offers a transferable membership to Mid South Club and Talamore Golf Resort for an exceptional lifestyle experience.

107 W Chelsea Ct, Southern Pines

Courtesy of Meese Property Group, LLC
$590,000
3 Beds ⋅ 2 Baths ⋅ 100575581 MLS
Live the golf course lifestyle in this beautifully maintained one-level home overlooking the 7th tee of Longleaf Golf & Family Club. Offering 3 bedrooms, 2 baths, and exceptional craftsmanship throughout, this home combines elegance, comfort, and thoughtful upgrades in one stunning package. From the welcoming front porch to the spacious rear Trek-like deck with a remote-controlled awning, this home was designed to enjoy both indoor and outdoor living. Relax with your morning coffee while taking in peaceful golf course views or entertain guests in the shaded comfort of your private backyard retreat. Inside, soaring 10 to 12-foot ceilings, beautiful crown molding, and real hardwood floors in the living areas create a warm and upscale feel throughout the main living areas. The flexible floorplan features both a formal living room and a comfortable family room with a fireplace, offering plenty of space for gathering or quiet relaxation. The spacious eat in kitchen is equipped with a dual-fuel range and the home is efficiently powered with natural gas, including the water heater, dryer, and furnace. The oversized garage offers excellent storage plus a walk-up attic above for even more space and convenience. The owner's suite is a true retreat with golf course views, a large bath featuring a soaking tub, walk-in shower, dual vanities, and separate his-and-her closets. Additional highlights include a fiber cement exterior, concrete driveway, encapsulated crawlspace, mature setting, and an unbeatable location close to the amenities of Southern Pines and Pinehurst. Homes with this combination of quality, one-level living, and golf course frontage are hard to find.

140 Steeplechase Way, Southern Pines

Courtesy of eXp Realty
$699,000
4 Beds ⋅ 4 Baths ⋅ 100575384 MLS
Beautiful in-ground pool, fenced backyard, and an unbeatable location -- this Highland Trails home has it all. Offering 4 bedrooms, 3.5 baths, and a spacious layout designed for everyday living and entertaining alike, this home stands out from the rest. Inside, you will find a large bonus recreation room complete with a wet bar, creating the perfect space for hosting friends, movie nights, game days, or simply spreading out and enjoying extra living space. Step outside to your private backyard retreat featuring a sparkling pool, a fully fenced backyard, and a separate fenced sitting area ideal for relaxing evenings or entertaining guests. Located in one of the area's most desirable neighborhoods, this home offers one of the quickest commutes to Fort Bragg while still being convenient to shopping, dining, golf, and everything Southern Pines has to offer. If you are looking for space, amenities, and location all in one, this home checks every box.

401 Dundee Trl, Southern Pines

Courtesy of Maison Realty Group

Buyer Representative Keller Williams Pinehurst
$235,000
2 Beds ⋅ 1 Baths ⋅ 100575333 MLS
Looking for step-free, one-level living in a welcoming 55+ community? This end-unit townhome in Village Green offers no steps to enter the home, a low-maintenance lifestyle, and a location that makes everyday living easier. The open floor plan connects the kitchen, dining area, and great room, creating comfortable spaces for everyday living and gathering with family and friends. One of the home's best features is the heated and cooled Carolina room overlooking a wooded backdrop. It's a peaceful place to enjoy your morning coffee, read a book, or watch the deer that frequently wander through the trees. The spacious primary bedroom and second bedroom provide flexibility for overnight guests, a home office, or hobbies. Village Green is known for its friendly 55+ community where neighbors know and care about one another. The HOA maintains the lawn and landscaping, so you can spend less time on home maintenance and more time enjoying life. Conveniently located just minutes from shopping, grocery stores, restaurants, medical care, and the Village of Southern Pines, you can take care of daily errands without dealing with busy traffic. If you're ready to simplify life with step-free entry, one-level living, HOA-maintained grounds, and a peaceful setting, this Village Green home is ready to welcome you.

1 Village Green Cir, Southern Pines

Courtesy of eXp Realty
$396,900
4 Beds ⋅ 3 Baths ⋅ 100460921 MLS
Welcome to Shaw Landing, one of Moore County's newest communities, just a stones throw away from Downtown Southern Pines. This prime location is conveniently located just blocks away from all the parks, shops, and restaurants that Southern Pines has to offer. Community Pool coming 2025! Introducing the stunning Lyon home plan, a two-story masterpiece that comes in two versions, Lyon A and Lyon B, each with differing exterior details. As soon as you step inside, you will be welcomed by a grand foyer that leads to a stylish mudroom on the right, equipped with a drop zone for coat and shoe storage, and a partial bathroom. The lower level also features a spacious living room with an electric fireplace, a large dining area that opens up to the covered back porch, and a well-appointed kitchen with an island and pantry. Upstairs, the Lyon plan boasts a luxurious owner's suite with a spacious walk-in closet and a beautiful owner's bathroom with double sinks. The upper level also features three additional bedrooms, a laundry room, and another full bathroom.

504 Burgundy Dr, Southern Pines

Courtesy of Ascot Realty Inc.

Buyer Representative Premier Real Estate of the Sandhills LLC
$1,560,000
4 Beds ⋅ 5 Baths ⋅ 100575295 MLS
Nestled on two private acres along prestigious Midland Road, this storybook 1928 white brick English Cottage offers a rare blend of timeless charm, nature, and thoughtful modern updates. Surrounded by mature dogwoods, blooming azaleas, perennial gardens, and trellised vines, the setting feels secluded and serene while remaining convenient to all Southern Pines has to offer. Located in the sought-after Knollwood neighborhood, known for its stately homes, large lots, and close proximity to Pine Needles, Mid Pines, and Knollwood golf courses, this home also carries a unique piece of local history as it was originally built for the son of famed Oakmont designer Henry Fownes. Inside, curated designer finishes and European influences create warmth and character throughout. Features include imported Portuguese tile, European light fixtures, Carrara Mist quartz countertops, and a Fulgor Milano 5-burner gas range. Original details such as marble flooring imported from England, hand-hewn beams, deep moldings, and hardwood floors blend beautifully with stylish additions made over the years. Offering close to 4,000 square feet with an additional 1,400 square feet of unheated living areas, the home provides an impressive amount of flexible space while still feeling inviting and comfortable. The outdoor spaces are equally impressive with a heated 40-foot in-ground pool, expansive patio areas, pool house with half bath, workshop space, and multiple private courtyards designed for relaxing or entertaining. The spacious primary suite features dual walk-in closets, a window seat with built-in storage, heated bubble tub, walk-in shower, and a stunning handmade beveled glass window. Just blocks from Whitehall Nature Preserve, this one-of-a-kind property offers privacy, history, character, and a lifestyle rarely found in Southern Pines

1335 Midland Rd, Southern Pines

Courtesy of Pines Sotheby's International Realty
$442,000
3 Beds ⋅ 2 Baths ⋅ 100575197 MLS
This beautiful updated ranch is located in the heart of Southern Pines. The downtown home blends timeless architectural character with comfortable everyday living. Featuring warm natural materials, expansive windows, and a functional single-level layout, this home offers inviting living spaces filled with natural light. The three bedroom, two full bath property has two fireplaces, a garage, separate laundry room and a covered back patio within a fenced in yard. The functionality of the home is showcased through beautiful built-ins in bedrooms and the hallway closet. The backyard is a true oasis - sit out back and smell the jasmine while enjoying the privacy and charm of the mid century build aesthetic, all while being just moments from downtown Southern Pines dining, shopping, golf, and recreation.

390 E Indiana Ave, Southern Pines

Courtesy of Everything Pines Partners LLC

Buyer Representative Everything Pines Partners LLC
$319,000
3 Beds ⋅ 3 Baths ⋅ 100575116 MLS
Welcome to 114 Cypress Circle in the heart of Southern Pines, a beautifully updated and low-maintenance townhouse located in a desirable Cypress Creek HOA community featuring a community pool and convenient access to everything the Sandhills has to offer. Just minutes from downtown Southern Pines, you'll enjoy easy access to local restaurants, breweries, shopping, golf, nightlife, and a quick commute to Fort Bragg/Fort Liberty, Pinehurst, and even Raleigh. This turn-key home has been freshly painted throughout and features all new ceiling fans and modern light fixtures, creating a clean and updated feel from the moment you walk in. The open-concept layout is highlighted by soaring ceilings, abundant natural light, and warm hardwood flooring that flows throughout the main living areas. The kitchen offers a modern custom design with granite countertops, stainless steel appliances, subway tile backsplash, floating wood shelves, updated hardware, and a sleek vent hood that creates a high-end contemporary look rarely found in townhouse living. The open dining and kitchen area flows seamlessly to the elevated rear deck overlooking mature trees and peaceful wooded surroundings perfect for morning coffee or relaxing evenings outdoors. The living room features a bold black painted brick fireplace with a rustic wood mantle, adding warmth and character to the space while complementing the home's modern finishes and neutral color palette. One of the standout features of the home is the recently renovated primary bathroom designed with luxury spa-inspired finishes including floor-to-ceiling marble tile, frameless glass shower doors, matte black fixtures, pebble-style shower flooring, custom shiplap accent wall, built-in shower niche, LED backlit mirror lighting, and a sleek modern vanity that truly elevates the space. The upstairs level offers two additional spacious bedrooms and a full bathroom, providing flexible space for guests, family, a home office, or additional living needs while maintaining privacy from the primary suite. Whether you're looking for a full-time residence, weekend getaway, or investment opportunity, 114 Cypress Circle offers stylish low-maintenance living in one of the most desirable and convenient locations in Southern Pines. $3000 Flooring Allowance offered to buyer at closing!

114 Cypress Cir, Southern Pines

Courtesy of Keller Williams Pinehurst
$645,750
5 Beds ⋅ 3 Baths ⋅ 100574859 MLS
OPEN HOUSE CANCELED DUE TO PENDING CONTRACT!!! SUMMER MOVE-IN READY and beautifully maintained by its original owner! This exceptional home has been freshly painted throughout in modern neutral tones, with all carpets professionally cleaned and the exterior recently soft-washed, making it truly move-in ready. The thoughtfully designed floor plan offers a first-floor guest suite or home office, an open-concept kitchen featuring granite countertops, a Butler's Pantry, stainless steel appliances, Bosch dishwasher, double ovens, upgraded natural gas cooktop, luxury wide-plank LVP flooring, and a whole-house water filtration system. The spacious great room includes surround sound connectivity, making it perfect for entertaining and everyday living. Additional highlights include: Formal dining room with coffered ceilings and wainscoting Two-car garage with built-in shelving and workbench Emergency power subpanel with power cord and 3kW generator Screened porch overlooking a fully fenced backyard Private natural area backdrop for added tranquility. Upstairs, you'll find a generous media loft, three spacious secondary bedrooms, two full baths, and an enormous primary suite featuring dual vanities, a walk-in shower, soaking tub, oversized walk-in closet, and conveniently located laundry room. For added peace of mind, a pre-listing home inspection has already been completed, and all recommended repairs have been addressed. Community Amenities: Resort-Style Swimming Pool with Expansive Sunning Deck Splash Pad Clubhouse Fitness Center Playground Lighted Sidewalks for Evening Strolls Conveniently located between Southern Pines and the Village of Pinehurst with an easy commute to Fort Bragg, this home offers the lifestyle today's buyers are searching for. Schedule your private showing today and discover why so many families love calling Arboretum home! Preferred Lender is Justin Price Motto Mortgage- 919-895-1769

170 Broom Sedge Ln, Southern Pines

Courtesy of Carolina Property Sales

Buyer Representative Meese Property Group, LLC
$530,000
3 Beds ⋅ 4 Baths ⋅ 100574416 MLS
Welcome to 80 Station Ave, a charming condo nestled in the highly desirable Walker Station neighborhood. Perfectly positioned for convenience, this home puts you right in the heart of Moore County, situated beautifully between Southern Pines, Pinehurst, and Whispering Pines. From the moment you arrive, you will love the fantastic curb appeal, highlighted by durable hardi-plank siding and two covered porches that exude classic Southern-style outdoor living. Step inside to find an inviting interior adorned with beautiful heart-of-pine flooring and elegant crown molding throughout the main living spaces. The kitchen is a true highlight, featuring stainless steel appliances and a natural gas range that is absolutely perfect for bringing out your inner chef. The gorgeous pine flooring extends into the well-appointed primary suite, which boasts a spacious walk-in closet complete with custom built-ins for ample storage. Upstairs, you will find two additional comfortable bedrooms and two full bathrooms, alongside a spacious bonus room that offers the ultimate flexibility for a home office or media room.

80 Station Ave, Southern Pines

Courtesy of Nexthome In The Pines
$555,000
3 Beds ⋅ 4 Baths ⋅ 100569900 MLS
Golf course views in Walker Station! Beautifully maintained three bedroom home with a partially screened wrap around porch facing the home of USKids Golf. Located between Southern Pines and Pinehurst with quick access to both, Walker Station is a unique community centered on open green spaces, a community pool and access to the Southern Pines Greenway. Primary suite on the main level with custom closet, fully tiled shower, water closet and coffee bar! The kitchen features plenty of granite counters, an island with a beverage fridge and stainless steel appliances. There is a spacious laundry room and 1/2 bath as well as generous pantry space. Two expansive bedrooms upstairs - each with its own luxurious bath and walk-in closet. There is a little flex room -currently being used as a sweet and cozy nursery. Additional storage space off the upstairs hallway. Fenced backyard and covered walkway to a 2 car garage ** with a Level 2 EV Charger** Above the garage is spacious unfinished storage space. Come home to Energy Star efficiency: natural gas fireplace, stove and tankless water heater; sealed crawlspace, energy efficient windows....all for your comfort in this wonderfully convenient community!

30 Station Ave, Southern Pines

Courtesy of Pines Sotheby's International Realty

Buyer Representative Keller Williams Pinehurst
$324,000
2 Beds ⋅ 2 Baths ⋅ 100574336 MLS
Excellent two bedroom/two bath townhome in Knollwood Village,a desirable55+age restricted community in Southern Pines. Large sunroom with walls of windows,formal dining room,stainless steel appliances,and lots of kitchen cabinets.Laundry room with washer and dryer included.Close to downtown shopping.Club membership transfer fee of $4000 with required monthly dues of $155 (single) and $185 (couple).

644 Redwood Dr, Southern Pines

Courtesy of Pinehurst Area Realty

Buyer Representative Premier Real Estate of the Sandhills LLC
$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
$1,075,000
4 Beds ⋅ 5 Baths ⋅ 100574090 MLS
Located inside the gates of Mid South Club, this well-crafted all-brick home offers a comfortable and refined lifestyle with thoughtful details throughout. Natural light fills the home, highlighting rich wood flooring, plantation shutters, detailed trim work, and updated lighting that add warmth and character to each space. A two-story foyer creates a welcoming entrance, while the layout is designed to function well for both everyday living and entertaining. The kitchen combines style and practicality with granite countertops, stainless steel appliances, a wet bar with wine refrigerator, and custom details that give the space personality without overwhelming it. The open flow of the home makes it easy to gather with family and guests alike. The primary suite provides a private retreat with a spacious bathroom that includes a soaking tub, tiled walk-in shower, and clean, timeless finishes. Upstairs, skylights bring natural light into the bonus room and bathroom, adding brightness and architectural character to the upper level. Outside, the fully fenced backyard is designed for both relaxation and entertaining, featuring an expansive stone patio and custom fire pit area ideal for enjoying evenings outdoors. Set along the Arnold Palmer-designed golf course, Mid South Club is known for its gated setting, mature landscaping, and convenient location near downtown Southern Pines. Whether you are looking for golf course living, quality construction, or a home with timeless style and functional spaces, this property offers all three.

216 Plantation Dr, Southern Pines

Courtesy of Everything Pines Partners LLC
$645,000
3 Beds ⋅ 2 Baths ⋅ LP748724 MLS
Located in the desirable Longleaf Country Club, this immaculate home offers stunning golf course views and exceptional craftsmanship throughout. Step inside to a gracious dining room with striking coffered ceilings, setting the tone for gatherings both formal and casual. The open living area centers around a warm gas fireplace and flows effortlessly into a chef's kitchen designed to impress, featuring a large island, farmhouse sink, stone backsplash, high-end appliances, and exquisite level 5 granite. Walls of windows in the Carolina Room invite the outdoors in, creating the perfect spot to sip your morning coffee while watching the sunrise over the course. The primary suite is a private retreat, complete with a sunlit study, two walk-in closets, and a spa-inspired ensuite with dual sinks and a walk-in shower. Two spacious guest bedrooms, a convenient laundry room, and thoughtful finishes throughout add to the home's appeal.Step outside to the back deck to relax or entertain as you take in the sweeping fairway views — all while being minutes from the best that Pinehurst and Southern Pines have to offer.

39 Paddock Ln, Southern Pines

Seller Representative MEESE PROPERTY GROUP

Buyer Representative

$714,960
5 Beds ⋅ 4 Baths ⋅ 2511005 MLS
FOR COMP PURPOSES ONLY: Bradenton Bungalow A (3rd car garage)

1005 W Hedgelawn Way, Southern Pines

Seller Representative HHHunt Homes of Raleigh-Durham

Buyer Representative

$395,000
3 Beds ⋅ 3 Baths ⋅ LP737185 MLS
Welcome to Shaws Landing! Ideally located close to downtown Southern Pines shopping, dining and entertainment. This thoughtfully designed Ascot home features an open foyer with abundant natural light and soaring high ceilings, leading you into the spacious living area. The open-concept kitchen is a chef's dream, with a large island, bright dining area, and a generously sized pantry for all your storage needs. The adjoined living room, flooded with natural light, is enhanced by a modern fireplace. The drop zone, located off the garage, offers a practical space for family storage, keeping the home tidy and functional. Upstairs, the private primary bedroom features a large walk-in closet and a luxurious bathroom with a walk-in shower. Two additional bedrooms, a full bathroom, laundry room and loft complete the upper level, offering plenty of space for family or guests. With thoughtful design and ample storage, this home is perfect for comfort, style, and everyday living!

409 Kendall Dr, Southern Pines

Seller Representative EVERYTHING PINES PARTNERS LLC

Buyer Representative

$350,000
3 Beds ⋅ 2 Baths ⋅ LP732454 MLS
299 Braden Road is nestled into an area of Southern Pines that offers a charming rural atmosphere, perfect for outdoor activities such as walking dogs and jogging. The blend of old horse farms and scenic backroads makes for a delightful environment where you can engage with nature and enjoy the community. Plus, seeing neighbors riding their horses adds a unique touch to the daily scenery! Just a reminder to keep an eye out for those horse droppings while you're out and about! This home is a total charmer, featuring a private, large yard fenced in for pets and privacy. The property just had a huge landscaping overhaul and the large patio offers additional entertaining space for outdoor enjoyment. Imagine cool nights, firepits, and creating lasting memories with family and friends. Extras include a spacious garage, 2 carports for additional parking, and an adorable shed.

299 Braden Rd, Southern Pines

Seller Representative LOVE PINES REALTY

Buyer Representative

$145,000
1 Beds ⋅ 1 Baths ⋅ LP729397 MLS
Quaint unit in Village Green only minutes from downtown Southern Pines shopping, restaurants, parks and more. This 1 bedroom 1 bathroom offers an abundance of light and easy one level living. The Village Green community is a 55 plus community. 48 Village Green is an end unit and it also has a Carolina room off the back. The entire unit offers vinyl flooring and it also has a pull down for more storage in the attic. New screen door will be installed next week off the kitchen. This is a rare find this close to downtown Southern Pines.

48 Village Green Cir, Southern Pines

Seller Representative BH&G REAL ESTATE - LIFESTYLE PROPERTY PARTNERS

Buyer Representative

$520,000
LP717109 MLS
Downtown duplex perfect for your investment! This 2 unit home is conveniently located within walking distance to some of Southern Pines's best shops, restaurants, pubs, parks, and more! Each 2 bed, 1.5 bath unit is light & bright anchored by warm flooring effortlessly connecting the main living areas. Each kitchen contains matching white appliances! The bedrooms are outfitted with plenty of closet storage. In-unit laundry is accessible in the half baths. Private decks adorn the exterior of each unit in addition to exterior storage. The convenience and functionality of this home are unmatched. This well-maintained property presents an excellent opportunity for both homeowners and investors alike.

750 N Page St, Southern Pines

Seller Representative MEESE PROPERTY GROUP

Buyer Representative

$1,340,000
5 Beds ⋅ 6 Baths ⋅ 2542100 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.

470 N Fort Bragg Rd, Southern Pines

Seller Representative Front Runner Realty Group

Buyer Representative

$210,000
2 Beds ⋅ 1 Baths ⋅ LP752856 MLS
Known as the Gem of Southern Pines, the Village Green is a welcoming 55+ community tucked among the trees—peaceful, private, and just minutes from downtown. This beautifully updated, low-maintenance first-level condo offers comfort and convenience at every turn, with a step-free entrance from the parking area for easy access. Inside, you'll find a warm, inviting layout with modern finishes throughout, including granite countertops, new flooring, stainless steel appliances, and soft-close cabinetry. The kitchen also features a hidden pantry, pocket door, and eye-catching mosaic tile backsplash. A brand-new hot water heater (2025) ensures worry-free living, and a new roof is already scheduled for 2027 under the HOA. Enjoy your mornings in the spacious enclosed sunroom, complete with heat and air—perfect for watching the sunrise with your coffee or relaxing in the evenings. The floored, insulated attic provides extra storage and improved energy efficiency. The Village Green community offers peaceful walking paths, a butterfly garden, and a charming gazebo where neighbors gather for cookouts and friendly conversations. Located close to downtown Southern Pines, you'll love being just minutes from restaurants, shops, and the renowned Sunrise Theater.

13 Village Green Cir, Southern Pines

Seller Representative MEESE PROPERTY GROUP

Buyer Representative

$661,260
4 Beds ⋅ 3 Baths ⋅ 2513614 MLS
FOR COMP PURPOSES ONLY: Winslow Heritage B

965 W Hedgelawn Way, Southern Pines

Seller Representative HHHunt Homes of Raleigh-Durham

Buyer Representative

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