View All Southern Pines NC Oversized Lot Homes Listings

$780,000
4 Beds 3 Baths 100580757 MLS
A rare historic downtown Southern Pines home with genuine soul, thoughtful updates, and a story. A contributing structure within the National Register-listed Southern Pines Historic District, this circa-1915 home offers the rare combination of historic craftsmanship, thoughtful updates, generous storage, and walkable downtown living in the heart of Southern Pines. The National Register continuation sheet lists 360 S. Ashe St. as a contributing structure and specifically notes the screened porch, French doors, sash windows, rear additions, and central corbelled-cap chimney. Lovingly cared for and updated over the years as both a real home and an artist's studio, the home retains the warmth and craftsmanship that make older Southern Pines homes so special -- original hardwood floors, high ceilings, three fireplaces, French doors, built-ins, oversized windows, and architectural details that simply cannot be replicated in newer construction. This is not a neglected historic house waiting to be rescued; it is a soulful, livable home with original details still intact. For added buyer confidence, a professional pre-listing appraisal was completed on June 9, 2026 and valued the property at $781,000. The home's history adds another layer of charm. Local historians have connected the property to Dr. Ernest Poate, a physician, psychiatrist, and mystery novelist who wrote under the pen name Arthur Mallory -- a fitting 1930s chapter for a home in a town long loved by doctors, writers, artists, and creative professionals. That same creative spirit continues today in a house that has been home to an award-winning photographer for the past 20 years and has served as both a private residence and a place of inspiration. Inside, the home offers four spacious bedrooms, 2.5 bathrooms, and flexible living spaces with abundant built-in storage throughout. One of the most memorable features is the large banquette beside a dramatic wall of leaded-glass windows that open to the screened porch; an ideal spot for morning coffee, reading, casual dining, or gathering with friends. French doors connect the main living areas to the porch, while additional French doors from the primary suite open directly to the backyard, creating a graceful indoor-outdoor flow rarely found in historic downtown homes. The primary suite features a fireplace and large infinity tub, while the second main bath offers a classic clawfoot tub -- blending comfort, charm, and timeless Southern Pines style. Outside, the property reveals one of its most special features: a private and peaceful fenced backyard retreat in the middle of downtown. A picket-fenced front garden creates storybook curb appeal, while the backyard offers mature trees, garden space, and room to entertain, relax, or enjoy time with pets beneath the Carolina pines. As downtown living becomes increasingly dense, this property stands out for its sense of space - a setting that feels tucked away and serene while still being just a block from restaurants, coffee shops, Gulley's Garden Center, and downtown shops, with parks and the Sunrise Theater just a little farther beyond. A large basement provides valuable storage space not included in the heated square footage, adding practical flexibility that is especially rare in a historic home. More than just a house, this is a lovingly cared-for piece of Southern Pines history -- a warm, creative, and deeply livable home with original soul, thoughtful updates, rare outdoor space, and a story that belongs to the town itself.

360 S Ashe St, Southern Pines

Courtesy of NorthGroup

$1,350,000
4 Beds 5 Baths 100388523 MLS
STUNNING & MOVE-IN-READY! One of the BEST Golf Views in the area! Located on an island of Golf completely surrounded by Holes 7 and 8 on the desirable Arnold Palmer designed Mid South Club Course. The homes sweeping views of fairway, green and pond are breathtaking. Hidden at the end of a private driveway flanked by brick columns at the entrance, the home is very, very private. With calming, comfortable, and elegant tones, tasteful details, generous rooms and a wonderful floor plan, serenity abounds from every room. A large and dramatic Carolina room with six sides and a 24 ft vaulted ceiling is the focal point of the main living area. The entry foyer, which opens to the stunning living room with a wall of windows bringing in abundant light throughout. Large gourmet kitchen open to Casual eating area and views of the golf course. The main-floor spacious master suite with tray ceiling opens to a handsome office with 16 ft ceiling overlooking the course. Stunning master bath with large walk-in closet. A guest bedroom, plus a hobby room or dramatic 5th bedroom are also located on the main floor. Upstairs enjoy a large recreation room, two spacious ensuite bedrooms, and a walk-in attic with ample storage. Well for irrigation and gas pack on heat pump. A large outdoor brick deck and an oversized 2-car garage completes this beauty that's LIKE NO OTHER!

220 Eagle Point Ln, Southern Pines

Courtesy of Lin Hutaff's Pinehurst Realty Group

Buyer Representative Pinnock Realty and Property Management LLC

$590,000
3 Beds 2 Baths LP763461 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, 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

Seller Representative EXP REALTY LLC

$590,000
3 Beds 2 Baths 763461 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, 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 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

$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

$1,595,000
4 Beds 4 Baths 100473211 MLS
250 Valleyfield Lane circa 1988 main residence is 4,304 SF with 4BR/3.5BA plus an 885 SF 1BR/1BA guest apartment over the garage with 5 acres and a pool. 246 Valleyfield Lane is the log cabin/guest cottage 1,616 SF, 3BR/2BA built in 2001 on 8.37 acres with 6 acres of fenced pasture, a pond, and stable/run-in shed. This magnificent property is a builder's personal residence and office ideally located just outside Southern Pines city limits in Weymouth and is just over 200 feet from Weymouth Woods Nature Preserve trails. Horse farms are on each side of this farm, and it is a short drive to the quaint downtown area. The main residence has abundant peachtree windows and doors, a 7-year-old cedar shake roof, real stucco, and wood exterior. The massive front doors and mantle are made of Linden wood, and many interior doors are antiques from the Holly Inn in Pinehurst. All bedrooms have walk-in closets and ensuites with the master suite having 3 walk-ins. The great room has a massive stacked stone, wood-burning fireplace and is open to the second floor. Formal and informal living spaces, and beautiful outdoor living on the stamped stone patio, inground pool, and pergola. The oversized garage (885 SF) is connected by a breezeway and has a recently renovated 1BR/1BA guest apartment overhead. A detached 3+ bay equipment shed with electricity is at the edge of the parcel. The guest cottage is an authentic log cabin with an open great room, wood-burning stone fireplace, and front porch overlooking the pond. Newer no-climb wire & wood-fenced pastures. Both homes have home warranties from America's Preferred Home Warranty. Termite warranties with BugOut. The generator does not convey. 2 large-yield wells service each home/parcel. Please limit showings to serious, pre-qualified buyers. The seller will need at least 60 days to close or seller possession after closing. The last sale fell through due to no fault of the property.

250 Valleyfield Ln, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative Keller Williams Pinehurst

$695,000
3 Beds 3 Baths 100467617 MLS
Beautiful, elegant, spacious home in desired Middleton Place, a handsome community of all brick homes in Southern Pines, North Carolina. From the inviting entrance and wide, long foyer to the expansive private courtyard, you know this home is very special. The largest home in the Community, each room is oversized for a seamless transition to downsizing from a large family home. Downsize to large! The formal dining room will easily service large dinner parties with access to equally spacious kitchen and sunny breakfast room. The elegant living room with fireplace and floor to ceiling windows opens to a handsome den with built-in desk and book shelves, plus back lighted wet bar. Shelving lines the large closet off the wet bar that has direct access to the garage. You will not be able to decide which room you love the most when you discover the Carolina room surrounded by windows and filled with natural light flooding the room. Great for afternoon bridge, Mah Jong or ''cozying up'' with a favorite book. The spacious Master suite is equally impressive with separate his and her bathrooms and large closets. Off the kitchen is an oversized utility room and 3rd bedroom/office. Middleton Place is perfectly situated between Pinehurst and Southern Pines and easy access to shopping, golf and all the area has to offer. UNIQUE PROPERTY. Courtyard fountain and Carolina room light fixture do not convey.

57 Manigault Pl, Southern Pines

Courtesy of Lin Hutaff's Pinehurst Realty Group

Buyer Representative Lin Hutaff's Pinehurst Realty Group

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Southern Pines, NC · Curated MLS Search

Oversized Lot Homes in Southern Pines, NC

An editorially curated view of every active oversized lot homes listing in Southern Pines, NC. Updated in real time from the local MLS, presented without the noise.

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