Perfectly positioned along the 8th hole and 5th tee of Longleaf Country Club, this beautiful cottage-style home offers scenic golf course views, a spacious floor plan, and exceptional indoor and outdoor living. A welcoming covered front porch leads into the foyer, where a formal dining room provides an elegant space for entertaining. The light-filled great room features a natural gas fireplace, custom built-in shelving, and expansive windows that bring in abundant natural light while showcasing the golf course setting. The well-appointed kitchen is designed for both everyday living and hosting family and friends, offering maple cabinetry, granite countertops, a pantry, breakfast bar, and sunny breakfast nook. The main-level owner's suite is a relaxing retreat with a spacious walk-in closet, double vanity, soaking tub, and separate walk-in shower. Two additional generously sized bedrooms, a full guest bath, and a functional mudroom with extensive cabinetry, countertop workspace, and storage complete the main level. The fully finished walkout basement expands the living space with two additional bedrooms, a full bathroom, and a large family room, ideal for guests, multi-generational living, or recreation. Outdoor living is equally impressive, featuring a spacious open-air deck overlooking the golf course with stairs leading to a covered patio below, accessible directly from the walkout basement. This home also has an integrated whole-house speaker system offering high-quality audio throughout the main living spaces as well as a six-zone irrigation system that helps keep the lawn beautifully maintained year-round. With its flexible floor plan, quality finishes, and prime golf course location, this exceptional home offers the perfect combination of comfort, functionality, and lifestyle.

112 Steeplechase Way, Southern Pines

Courtesy of The Gentry Team

$2,495,000

4 Beds ⋅ 5 Baths ⋅ 10159060 MLS

This is the one you have been searching for, an architectural masterpiece that redefines the very concept of a luxury estate. The crown jewel of Mid South, this property offers a level of curated sophistication and raw natural beauty that is simply irreplaceable; it is an ultra exclusive retreat where every line and every view has been engineered to take your breath away. The estate presence is immediate as you pull into the circular driveway, a private peninsula tucked at the end of a culdesac where the warm glow of gas lights on the front porch welcomes you home. Step through the grand entrance into a main level of over 3,000 square feet where soaring 12 foot coffered ceilings and rich 9 inch hardwoods meet vast windows that frame the landscape. The home is so flooded with natural light you will rarely need to turn the lights on, allowing the outdoors to serve as your primary decor. The kitchen serves as a culinary masterpiece featuring Thermador appliances, a hidden scullery, and an additional walk in pantry so every possession has its own dedicated place. A custom dumbwaiter serves the home, ensuring seamless service between levels for streamlined entertaining. The main living area flows beautifully from the kitchen into the family room and then directly out to the definitive highlight of the property, The Observatory. This unique circular, screened in retreat with integrated heaters and invisible cable railings suspends you above the landscape, providing a 250 degree panoramic sweep that looks down and out over the 16th tee and the shimmering water views. The main floor features a primary suite with dual walk in closets and a direct connection to the private laundry center. A sophisticated guest bedroom is tucked away to ensure total seclusion for your visitors. Descend to the basement walkout level entertainment hub where you will find a second full kitchen and the ultimate connoisseur's retreat: a temperature controlled wine cellar behind stunning glass arched doors, meticulously designed to house 648 bottles of your finest collection. This level features two additional bedrooms, both with attached full bathrooms, and a game room alongside a media area. The walkout level also features a premier fitness studio with a panoramic view of the golf course for serene morning workouts. Step out to your private oasis featuring a heated saltwater pool with a tanning ledge, a therapeutic hot tub, and a professional outdoor kitchen designed for grand scale hosting. The experience is anchored by over 1,200 square feet of garage space featuring extra large doors specifically designed for large vehicles and electric vehicle charging. This technical powerhouse is further protected by a whole home Generac generator, ensuring the estate remains fully operational in any conditions. Living in Mid South Club provides more than a home; it grants access to a world class lifestyle defined by a premier clubhouse and a vibrant social calendar. Residents enjoy the ultimate golf cart friendly community with access to championship courses and resort style amenities including tennis and swimming. This legacy entertaining estate offers a front row seat to the finest sunrise and sunset in the Sandhills.

4 Weaver Ct, Southern Pines

Seller Representative VIVID PROPERTY GROUP

$665,000

4 Beds ⋅ 3 Baths ⋅ LP761430 MLS

Discover the perfect blend of space, charm, and convenience in this sought-after Southern Pines home, just a 10-minute walk to vibrant downtown. This rare three-story property offers over 2,800 square feet of living space on a fully fenced 0.51-acre lot, with a pre-listing inspection already completed for added peace of mind.The main living areas feature four bedrooms and three bathrooms, with a functional layout that includes two bedrooms and two full baths on the main level, plus two additional bedrooms and a full bath upstairs.The semi-finished walkout basement adds exceptional flexibility, offering three bonus rooms currently used as a guest room, media room, and additional living space, creating an ideal opportunity for a future apartment or private retreat with a little imagination.Thoughtful details throughout include plantation shutters, a carport with electricity, a charming tree house, and a cozy fire pit, perfectly capturing the relaxed lifestyle Moore County is known for.

440 Kensington Rd, Southern Pines

Seller Representative PINELAND PROPERTY GROUP, LLC.

Buyer Representative

$665,000

4 Beds ⋅ 3 Baths ⋅ 761430 MLS

Discover the perfect blend of space, charm, and convenience in this sought-after Southern Pines home, just a 10-minute walk to vibrant downtown. This rare three-story property offers over 2,800 square feet of living space on a fully fenced 0.51-acre lot, with a pre-listing inspection already completed for added peace of mind. The main living areas feature four bedrooms and three bathrooms, with a functional layout that includes two bedrooms and two full baths on the main level, plus two additional bedrooms and a full bath upstairs. The semi-finished walkout basement adds exceptional flexibility, offering three bonus rooms currently used as a guest room, media room, and additional living space, creating an ideal opportunity for a future apartment or private retreat with a little imagination. Thoughtful details throughout include plantation shutters, a carport with electricity, a charming tree house, and a cozy fire pit, perfectly capturing the relaxed lifestyle Moore County is known for.

440 Kensington Road, Southern Pines

Courtesy of PINELAND PROPERTY GROUP, LLC.

Buyer Representative Non Member Office

$2,495,000

4 Beds ⋅ 5 Baths ⋅ 100567176 MLS

This is the one you have been searching for, an architectural masterpiece that redefines the very concept of a luxury estate. The crown jewel of Mid South, this property offers a level of curated sophistication and raw natural beauty that is simply irreplaceable; it is an ultra exclusive retreat where every line and every view has been engineered to take your breath away. The estate presence is immediate as you pull into the circular driveway, a private peninsula tucked at the end of a culdesac where the warm glow of gas lights on the front porch welcomes you home. Step through the grand entrance into a main level of over 3,000 square feet where soaring 12 foot coffered ceilings and rich 9 inch hardwoods meet vast windows that frame the landscape. The home is so flooded with natural light you will rarely need to turn the lights on, allowing the outdoors to serve as your primary decor. The kitchen serves as a culinary masterpiece featuring Thermador appliances, a hidden scullery, and an additional walk in pantry so every possession has its own dedicated place. A custom dumbwaiter serves the home, ensuring seamless service between levels for streamlined entertaining. The main living area flows beautifully from the kitchen into the family room and then directly out to the definitive highlight of the property, The Observatory. This unique circular, screened in retreat with integrated heaters and invisible cable railings suspends you above the landscape, providing a 250 degree panoramic sweep that looks down and out over the 16th tee and the shimmering water views. The main floor features a primary suite with dual walk in closets and a direct connection to the private laundry center. A sophisticated guest bedroom is tucked away to ensure total seclusion for your visitors. Descend to the basement walkout level entertainment hub where you will find a second full kitchen and the ultimate connoisseur's retreat: a temperature controlled wine cellar behind stunning glass arched doors, meticulously designed to house 648 bottles of your finest collection. This level features two additional bedrooms, both with attached full bathrooms, and a game room alongside a media area. The walkout level also features a premier fitness studio with a panoramic view of the golf course for serene morning workouts. Step out to your private oasis featuring a heated saltwater pool with a tanning ledge, a therapeutic hot tub, and a professional outdoor kitchen designed for grand scale hosting. The experience is anchored by over 1,200 square feet of garage space featuring extra large doors specifically designed for large vehicles and electric vehicle charging. This technical powerhouse is further protected by a whole home Generac generator, ensuring the estate remains fully operational in any conditions. Living in Mid South Club provides more than a home; it grants access to a world class lifestyle defined by a premier clubhouse and a vibrant social calendar. Residents enjoy the ultimate golf cart friendly community with access to championship courses and resort style amenities including tennis and swimming. This legacy entertaining estate offers a front row seat to the finest sunrise and sunset in the Sandhills.

4 Weaver Ct, Southern Pines

Courtesy of Vivid Property Group

$665,000

4 Beds ⋅ 3 Baths ⋅ 100545309 MLS

Discover the perfect blend of space, charm, and convenience in this sought-after Southern Pines home, just a 10-minute walk to vibrant downtown. This rare three-story property offers over 2,800 square feet of living space on a fully fenced 0.51-acre lot, with a pre-listing inspection already completed for added peace of mind. The main living areas feature four bedrooms and three bathrooms, with a functional layout that includes two bedrooms and two full baths on the main level, plus two additional bedrooms and a full bath upstairs. The semi-finished walkout basement adds exceptional flexibility, offering three bonus rooms currently used as a guest room, media room, and additional living space, creating an ideal opportunity for a future apartment or private retreat with a little imagination. Thoughtful details throughout include plantation shutters, a carport with electricity, a charming tree house, and a cozy fire pit, perfectly capturing the relaxed lifestyle Moore County is known for.

440 Kensington Rd, Southern Pines

Courtesy of Pineland Property Group LLC

Buyer Representative Non Member Office

$825,000

4 Beds ⋅ 3 Baths ⋅ 100538676 MLS

This stunning contemporary home on 2 acres of heavily wooded land creates unmatched serenity and privacy! Premier architecture matches innovation and stunning views from nearly every gathering place. Feel the mood change from room-to-room as pristine ceiling & beam design defines each space and frames the natural light from ingeniously placed windows. The azaleas and huge mature trees fill the living room windows and foster a sense of calm and quietude. Nearly 3,000 sq. ft. on the main level including a loft with overlook that has its own full bathroom. Finished walkout basement is not included in the square footage and is a perfect theatre, game room or living area. Amazing master suite transitions from a mountain home feel by day to a private luxury suite by night. Newly renovated shower, jetted tub and walk-in closet completes this suite located far away from the entertaining areas of the home. Rich hardwood floors, granite counters, 2 masonry fireplaces, a massive laundry room and many other features are sure to impress. Huge elevated screened-in-porch stays cool even in the summer under the shade and protection of the massive tree cover. Outdoor firepit and tree-house are enjoyed in the back of this large property. The home is on county water but also has a functioning well which benefits the outdoorsman and kids alike. Showstopper of a home in a highly desirable location.

2145 Midland Rd, Southern Pines

Courtesy of Coldwell Banker Advantage-Fayetteville

Buyer Representative Rise Realty Collective

$117,000

100486440 MLS

Nice building lot in popular Sandhurst Area. KLot slopes to the back and would be good for a walkout basement plan. Easy access to downtown Southern Pines shopping, restaurants and services.

Tbd Tbd Clearfield Ln, Southern Pines

Courtesy of Berkshire Hathaway HS Pinehurst Realty Group/PH

Buyer Representative eXp Realty

View All Southern Pines NC Homes with Walk-Out Basement Listings

Homes with Walk-Out Basement in Southern Pines, NC

Southern Pines, NC Market Snapshot

Next Steps in Southern Pines, NC