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$445,000

Tucked among the pines, this charming 4-bedroom, 3-bath brick home offers flexibility, privacy, and a layout that works beautifully for everyday living, multi-generational needs, or investment potential, long or short-term. The main level features a spacious kitchen, hardwood floors, tile, and three comfortable bedrooms with plenty of natural light and character throughout. Downstairs, you'll find a private fourth bedroom and full bathroom arranged as its own mother-in-law suite, complete with both exterior access and interior access to the home. This level also features new LVP flooring, a cozy living area with chic décor, laundry space, and access to an unfinished storage room--giving you additional room for storage, hobbies, or future possibilities. Outside, enjoy a large, private fenced backyard, a spacious deck perfect for relaxing or entertaining, and plenty of parking for guests or multiple vehicles. Adding even more versatility, the home has a long Airbnb history as two separate units and may be sold fully furnished, making it an appealing option for an investor or a buyer looking for a move-in-ready property. The home may also be eligible for assumption of an existing 2.75% VA loan, subject to lender and VA approval. Additional updates include a 2015 roof and HVAC installed in 2021. Termite Warranty in place. Conveniently located just minutes from Downtown Southern Pines and Highway 1, approximately 20 minutes to Camp Mackall and 40 minutes to Fort Bragg, this home combines a tucked-away setting with easy access to shopping, dining, world class golf. Zoned for McDeeds Elementary

4 Beds ⋅ 3 Baths ⋅ 100595903 MLS

Tucked among the pines, this charming 4-bedroom, 3-bath brick home offers flexibility, privacy, and a layout that works beautifully for everyday living, multi-generational needs, or investment potential, long or short-term. The main level features a spacious kitchen, hardwood floors, tile, and three comfortable bedrooms with plenty of natural light and character throughout. Downstairs, you'll find a private fourth bedroom and full bathroom arranged as its own mother-in-law suite, complete with both exterior access and interior access to the home. This level also features new LVP flooring, a cozy living area with chic décor, laundry space, and access to an unfinished storage room--giving you additional room for storage, hobbies, or future possibilities. Outside, enjoy a large, private fenced backyard, a spacious deck perfect for relaxing or entertaining, and plenty of parking for guests or multiple vehicles. Adding even more versatility, the home has a long Airbnb history as two separate units and may be sold fully furnished, making it an appealing option for an investor or a buyer looking for a move-in-ready property. The home may also be eligible for assumption of an existing 2.75% VA loan, subject to lender and VA approval. Additional updates include a 2015 roof and HVAC installed in 2021. Termite Warranty in place. Conveniently located just minutes from Downtown Southern Pines and Highway 1, approximately 20 minutes to Camp Mackall and 40 minutes to Fort Bragg, this home combines a tucked-away setting with easy access to shopping, dining, world class golf. Zoned for McDeeds Elementary

435 Midland Rd, Southern Pines

Listing courtesy of Carolina Property Sales. Contact:

$749,000

A rare gem nestled in the heart of downtown Southern Pines, this gorgeous home which is listed on the National Historic Registry, offers the perfect blend of charm, privacy and walkable downtown living. Just steps from local boutiques, restaurants, coffee shops, and everything downtown has to offer, you'll love the convenience of being able to walk almost everywhere. Inside, High Ceilings, Original hardwood floors, Three Fireplaces, Four spacious Bedrooms, 2.5 bathrooms, and a screened in porch showcase the character and craftsmanship of a bygone era. Step outside to discover a truly one-of-a-kind private backyard, a retreat in downtown Southern Pines that's ideal for entertaining, gardening, or simply relaxing beneath the Carolina pines. More than just a home, this is a chance to own a piece of Southern Pines history and enjoy one of the area's most sought after locations.

4 Beds ⋅ 3 Baths ⋅ 764169 MLS

A rare gem nestled in the heart of downtown Southern Pines, this gorgeous home which is listed on the National Historic Registry, offers the perfect blend of charm, privacy and walkable downtown living. Just steps from local boutiques, restaurants, coffee shops, and everything downtown has to offer, you'll love the convenience of being able to walk almost everywhere. Inside, High Ceilings, Original hardwood floors, Three Fireplaces, Four spacious Bedrooms, 2.5 bathrooms, and a screened in porch showcase the character and craftsmanship of a bygone era. Step outside to discover a truly one-of-a-kind private backyard, a retreat in downtown Southern Pines that's ideal for entertaining, gardening, or simply relaxing beneath the Carolina pines. More than just a home, this is a chance to own a piece of Southern Pines history and enjoy one of the area's most sought after locations.

360 S Ashe Street, Southern Pines

Listing courtesy of NORTHGROUP REAL ESTATE. Contact:

$749,000

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.

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

Listing courtesy of NorthGroup. Contact: