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

650 E Indiana Ave, Southern Pines

Courtesy of Pines Sotheby's International Realty

$699,000
5 Beds 4 Baths LP764441 MLS
Located just a short distance from downtown Southern Pines, this 1925 home presents a rare opportunity to restore a piece of local history in the highly desirable Weymouth Heights community. The property has been partially demoed and is ready for renovation, offering a blank canvas for investors, builders, or buyers with a vision.The kitchen has been stripped down to the rough finish stage, with all cabinets and appliances removed, allowing you to design and customize the space to your preferences. While the home is currently in poor condition and requires extensive renovation, its character, location, and potential make it a standout opportunity.Enjoy the charm and convenience of downtown Southern Pines, with its unique shops, restaurants, parks, and outdoor recreation just minutes away. Bring this historic home back to its former beauty and create something truly special in one of the area’s most sought-after neighborhoods.

145 Highland Rd, Southern Pines

Seller Representative RE/MAX SOUTHERN PROPERTIES LLC.

$699,000
5 Beds 4 Baths 764441 MLS
Located just a short distance from downtown Southern Pines, this 1925 home presents a rare opportunity to restore a piece of local history in the highly desirable Weymouth Heights community. The property has been partially demoed and is ready for renovation, offering a blank canvas for investors, builders, or buyers with a vision. The kitchen has been stripped down to the rough finish stage, with all cabinets and appliances removed, allowing you to design and customize the space to your preferences. While the home is currently in poor condition and requires extensive renovation, its character, location, and potential make it a standout opportunity. Enjoy the charm and convenience of downtown Southern Pines, with its unique shops, restaurants, parks, and outdoor recreation just minutes away. Bring this historic home back to its former beauty and create something truly special in one of the area’s most sought-after neighborhoods.

145 Highland Road, Southern Pines

Courtesy of RE/MAX SOUTHERN PROPERTIES LLC.

$699,000
5 Beds 4 Baths 100582154 MLS
Located just a short distance from downtown Southern Pines, this 1925 home presents a rare opportunity to restore a piece of local history in the highly desirable Weymouth Heights community. The property has been partially demoed and is ready for renovation, offering a blank canvas for investors, builders, or buyers with a vision. The kitchen has been stripped down to the rough finish stage, with all cabinets and appliances removed, allowing you to design and customize the space to your preferences. While the home is currently in poor condition and requires extensive renovation, its character, location, and potential make it a standout opportunity. Enjoy the charm and convenience of downtown Southern Pines, with its unique shops, restaurants, parks, and outdoor recreation just minutes away. Bring this historic home back to its former beauty and create something truly special in one of the area's most sought-after neighborhoods.

145 Highland Rd, Southern Pines

Courtesy of RE/MAX Southern Properties

$1,145,000
4 Beds 4 Baths LP763553 MLS
The Maplewood Cottage (2,932 sq ft) is complemented by a fully furnished detached guest house (479 sq ft), creating a property that combines flexible living space, privacy, and the character of Weymouth Heights Historic District within one of Southern Pines' most established residential settings. Thoughtfully updated while preserving the scale and feel of the surrounding neighborhood, the property offers five bedrooms, multiple gathering spaces, and strong connections between indoor and outdoor living. Just off the front entry, a more intimate sitting room creates a welcoming introduction to the home. Beyond the double doors, the main living spaces open into the great room and adjoining Carolina room, where vaulted ceilings, expansive windows, and views of the surrounding landscape create a natural focal point. French doors, exposed brick accents, and strong sight lines throughout the rear living areas reinforce the connection between the interior spaces and the mature pines beyond. The kitchen, dining, and living areas are comfortably integrated to create a functional and inviting central living space. The renovated kitchen balances function and design with stone countertops, ceramic tile backsplash, Bertazzoni gas range, and a large central island that anchors the space naturally. Adjacent to the kitchen, the butler's pantry includes a wet bar along with additional storage and serving space. The primary suite features custom armoire-style storage, fireplace feature wall, and a spacious bath with dual vanity and large walk-in shower. Expansive windows throughout the home bring in soft natural light and reinforce the connection to the surrounding property. Outdoor spaces feel private and well established, with brick patios, garden paths, mature landscaping, and a large fenced backyard that includes a separate white picket enclosed area accented with copper-capped detailing. One patio connects directly to the primary suite and hot tub area, while another extends from the rear living spaces beneath the canopy of mature trees. Above the detached two-car garage, the fully furnished, turn-key guest house extends the functionality of the property, offering a comfortable and well-designed space for visitors or longer-term stays. Complete with a full bath, kitchenette, and open living area, it provides flexibility while maintaining privacy from the main residence. A short distance from downtown Southern Pines and the trails of Weymouth Woods, the property is well positioned for both daily convenience and outdoor recreation. Residents enjoy easy access to Broad Street's locally owned restaurants, shops, and historic downtown character, along with miles of nearby walking trails through protected longleaf pine forest characteristic of the Sandhills region. This 1.68 acre property offers a distinctive combination of privacy, updated living space, guest accommodations, and proximity to both downtown Southern Pines and Weymouth Woods within one of the area's most established neighborhoods.

305 Maples Rd, Southern Pines

Seller Representative EVERYTHING PINES PARTNERS LLC

$1,145,000
4 Beds 4 Baths 763553 MLS
The Maplewood Cottage (2,932 sq ft) is complemented by a fully furnished detached guest house (479 sq ft), creating a property that combines flexible living space, privacy, and the character of Weymouth Heights Historic District within one of Southern Pines' most established residential settings. Thoughtfully updated while preserving the scale and feel of the surrounding neighborhood, the property offers five bedrooms, multiple gathering spaces, and strong connections between indoor and outdoor living. Just off the front entry, a more intimate sitting room creates a welcoming introduction to the home. Beyond the double doors, the main living spaces open into the great room and adjoining Carolina room, where vaulted ceilings, expansive windows, and views of the surrounding landscape create a natural focal point. French doors, exposed brick accents, and strong sight lines throughout the rear living areas reinforce the connection between the interior spaces and the mature pines beyond. The kitchen, dining, and living areas are comfortably integrated to create a functional and inviting central living space. The renovated kitchen balances function and design with stone countertops, ceramic tile backsplash, Bertazzoni gas range, and a large central island that anchors the space naturally. Adjacent to the kitchen, the butler's pantry includes a wet bar along with additional storage and serving space. The primary suite features custom armoire-style storage, fireplace feature wall, and a spacious bath with dual vanity and large walk-in shower. Expansive windows throughout the home bring in soft natural light and reinforce the connection to the surrounding property. Outdoor spaces feel private and well established, with brick patios, garden paths, mature landscaping, and a large fenced backyard that includes a separate white picket enclosed area accented with copper-capped detailing. One patio connects directly to the primary suite and hot tub area, while another extends from the rear living spaces beneath the canopy of mature trees. Above the detached two-car garage, the fully furnished, turn-key guest house extends the functionality of the property, offering a comfortable and well-designed space for visitors or longer-term stays. Complete with a full bath, kitchenette, and open living area, it provides flexibility while maintaining privacy from the main residence. A short distance from downtown Southern Pines and the trails of Weymouth Woods, the property is well positioned for both daily convenience and outdoor recreation. Residents enjoy easy access to Broad Street's locally owned restaurants, shops, and historic downtown character, along with miles of nearby walking trails through protected longleaf pine forest characteristic of the Sandhills region. This 1.68 acre property offers a distinctive combination of privacy, updated living space, guest accommodations, and proximity to both downtown Southern Pines and Weymouth Woods within one of the area's most established neighborhoods.

305 Maples Road, Southern Pines

Courtesy of EVERYTHING PINES PARTNERS LLC

$541,000
4 Beds 3 Baths 100577127 MLS
Welcome to 125 Cliff Road -- a beautiful, low-maintenance brick home nestled on a lush 0.80-acre lot in one of Southern Pines' most sought-after neighborhoods. Classic curb appeal, and an unmatched outdoor living experience make this a truly special opportunity.. Inside, four generously sized bedrooms and 2.5 baths provide comfortable, flexible living for any lifestyle. Rich hardwood floors flow throughout the main living areas, while the family room anchors itself around a beautiful masonry fireplace with gas logs -- an inviting focal point through every season. Step into a kitchen that is equipped with stainless steel appliances, oak cabinets and breakfast bar area. The flow and layout are perfect for entertaining. The primary suite offers a nice retreat with his-and-her closets. The outdoor living space is nothing short of spectacular. A gorgeous pool takes center stage, surrounded by a spacious deck and patio that invite you to linger long after the sun begins to dip. The mature, established landscaping wraps the entire property in natural beauty, creating a sense of peace and serenity. Whether you're hosting a summer gathering or savoring a quiet morning with your coffee this yard delivers the peace and privacy you crave. As the temperatures cool, gather friends around the fire pit for warm evenings under the stars. The fully fenced backyard ensures a private, secure setting -- your own personal sanctuary just steps from the back door. This is outdoor living at its finest. The oversized two-car garage with insulated doors, a workshop area, and built-in storage cabinets offer exceptional utility. The encapsulated crawlspace is a great bonus feature for extra ease of mind and comfort. This home is perfectly located with easy access to downtown Southern Pines, parks, schools, shops, and a quick commute to Fort Bragg

125 Cliff Rd, Southern Pines

Courtesy of Rhodes and Co LLC

Buyer Representative Pineland Property Group LLC

$636,000
5 Beds 3 Baths 100546721 MLS
SELLERS OFFERING $10,000 ''USE AS YOU CHOOSE'' INCENTIVE with an acceptable offer!!! Fantastic opportunity to own your dream home in the highly sought-after Arboretum neighborhood in Southern Pines. Elegant and thoughtfully designed, this stunning 3,240-square-foot residence offers 5 bedrooms and 3 full baths with spacious, light-filled rooms ideal for both everyday living and entertaining. The heart of the home is the beautifully updated kitchen, featuring high-end appliances, custom lighting, tile backsplash, and a walk-in pantry, open to both the living room and casual dining area for easy everyday living and entertaining. A separate formal dining room offers an elegant setting for special occasions. A bedroom and full bath on the main level for guests or a home office, while upstairs you'll find the spacious primary suite, three additional bedrooms, and a conveniently located laundry room. Custom drapes and plantation shutters throughout the home frame picturesque views of the lush surroundings. Step outside to an exceptional, park-like setting that feels like a private retreat. The meticulously designed grounds feature mature trees, curated shrubs, hundreds of seasonal bulbs, and fragrant jasmine, gardenia, and magnolia trees. Outdoor living is elevated with custom stone walls, a private Brazilian hardwood deck, stamped concrete patio, wood fire-pit area, a natural gas fire table, and multiple spaces for gathering. Enjoy alfresco dining beneath a grapevine-covered pergola or unwind on the swing beneath a jasmine-covered arbor. Community residents enjoy sidewalks throughout the neighborhood, access to the community pool, clubhouse and playground. Ideally located, the Arboretum offers easy access to the Village of Pinehurst, downtown Southern Pines, and a short commute to Fort Bragg. This remarkable home offers timeless elegance, exceptional outdoor living, and an unbeatable location in one of Southern Pines' most desirable neighborhoods.

275 Wiregrass Ln, Southern Pines

Courtesy of Fore Properties

Buyer Representative Keller Williams Pinehurst

$732,800
4 Beds 3 Baths 100447882 MLS
Welcome to 225 S Valley Road! This meticulously maintained, charming classic house is located in Weymouth Heights, one of the most serene neighborhoods, just a few short blocks from downtown. The home features four bedrooms and three full baths, set on nearly an acre of manicured and vibrant land. The open and airy living room and kitchen form the heart of the home, perfect for gatherings and everyday living. With only some light remodeling, the kitchen can be easily remade into the one of your dreams! The master bedroom, along with another bedroom, is conveniently located downstairs. Upstairs, you'll find two additional bedrooms and a full bath; one of these bedrooms can easily be converted into a large office or workspace. The well-maintained kitchen, though older, adds to the home's charm. Additional features include a spacious mudroom, a formal dining room, and a formal living room. The expansive outdoor space offers endless possibilities for gardening, recreation, and relaxation. This beautiful home combines classic charm with modern conveniences, making it the ideal choice for those seeking tranquility close to downtown amenities. Don't miss the chance to make this house your new home. Contact us today for more information or to schedule a viewing.

225 S Valley Rd, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative Fore Properties

$640,000
4 Beds 3 Baths 100501499 MLS
Welcome to this stunning newer construction by Pineland Homes and Remodeling, perfectly blending timeless farmhouse style with modern upgrades. Nestled in the heart of Downtown Southern Pines, this picturesque home offers the best of both charm and convenience. Boasting 4 spacious bedrooms and 2 beautifully appointed bathrooms, this home was thoughtfully designed for both everyday living and entertaining. The open-concept layout features upgraded finishes throughout, creating a warm and stylish atmosphere. Step outside to your private backyard oasis complete with a cozy fire pit—perfect for relaxing evenings or gathering with friends. With its prime location, you're just a short stroll away from all the shops, dining, and vibrant community events that downtown has to offer. Don't miss this rare opportunity to own a move-in-ready modern farmhouse in one of the most desirable neighborhoods in Southern Pines!

225 W Vermont Ave, Southern Pines

Courtesy of Front Runner Realty Group

Buyer Representative Fore Properties

IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS.  The MLS may, at its discretion, require use of other disclaimers as necessary to protect participants and/or the MLS from liability. 

Listings provided by LERA MLS

All information should be verified by the recipient and none is guaranteed as accurate by ARMLS. Copyright 2026 Arizona Regional Multiple Listing Service, Inc. All rights reserved.

Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .

Copyright 2026 NCRMLS. All rights reserved. North Carolina Regional Multiple Listing Service, (NCRMLS), provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. NCRMLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of NCRMLS.