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$1,375,000

Set on 3.21 private acres in Weymouth Heights, this 1924 estate offers architectural character, established gardens, and a detached guest cottage in one of Southern Pines' most treasured neighborhoods. Historic brick fencing lines portions of the drive, while mature pines, hardwoods, evergreens, and more than 300 flowering azaleas create a setting that has evolved beautifully over generations, just moments from downtown Southern Pines and Weymouth Woods. The 4-bedroom main residence blends thoughtful updates with original character, featuring hardwood floors, extensive mill work, custom built-ins, and four working fireplaces. Large windows frame views of the surrounding grounds, while multiple gathering spaces--including a spacious Great Room, dedicated office, and light-filled Carolina Room--provide flexibility for everyday living and entertaining. The kitchen is appointed with custom Rutt cherry cabinetry, Sub-Zero refrigeration, Dacor double ovens, a five-burner gas cook top, generous workspace, and abundant storage. The main-level primary suite offers a spacious bath, walk-in closet, fireplace, and direct connection to the Carolina Room and outdoor living spaces. Outside, flagstone walkways, stone terraces, expansive lawn areas, and a brick fireplace courtyard create inviting spaces to enjoy the property's exceptional landscape. A detached 659-square-foot guest cottage with a bedroom, full bath, living area, and fireplace provides additional flexibility for guests, extended family, or a private workspace. A rare opportunity to own a significant Weymouth Heights property with privacy, character, and convenience in the heart of Southern Pines.

4 Beds ⋅ 4 Baths ⋅ LP765723 MLS

Set on 3.21 private acres in Weymouth Heights, this 1924 estate offers architectural character, established gardens, and a detached guest cottage in one of Southern Pines' most treasured neighborhoods. Historic brick fencing lines portions of the drive, while mature pines, hardwoods, evergreens, and more than 300 flowering azaleas create a setting that has evolved beautifully over generations, just moments from downtown Southern Pines and Weymouth Woods. The 4-bedroom main residence blends thoughtful updates with original character, featuring hardwood floors, extensive mill work, custom built-ins, and four working fireplaces. Large windows frame views of the surrounding grounds, while multiple gathering spaces--including a spacious Great Room, dedicated office, and light-filled Carolina Room--provide flexibility for everyday living and entertaining. The kitchen is appointed with custom Rutt cherry cabinetry, Sub-Zero refrigeration, Dacor double ovens, a five-burner gas cook top, generous workspace, and abundant storage. The main-level primary suite offers a spacious bath, walk-in closet, fireplace, and direct connection to the Carolina Room and outdoor living spaces. Outside, flagstone walkways, stone terraces, expansive lawn areas, and a brick fireplace courtyard create inviting spaces to enjoy the property's exceptional landscape. A detached 659-square-foot guest cottage with a bedroom, full bath, living area, and fireplace provides additional flexibility for guests, extended family, or a private workspace. A rare opportunity to own a significant Weymouth Heights property with privacy, character, and convenience in the heart of Southern Pines.

285 N Bethesda Rd Ne, Southern Pines

Seller Representative EVERYTHING PINES PARTNERS LLC

$1,375,000

Set on 3.21 private acres in Weymouth Heights, this 1924 estate offers architectural character, established gardens, and a detached guest cottage in one of Southern Pines' most treasured neighborhoods. Historic brick fencing lines portions of the drive, while mature pines, hardwoods, evergreens, and more than 300 flowering azaleas create a setting that has evolved beautifully over generations, just moments from downtown Southern Pines and Weymouth Woods. The 4-bedroom main residence blends thoughtful updates with original character, featuring hardwood floors, extensive mill work, custom built-ins, and four working fireplaces. Large windows frame views of the surrounding grounds, while multiple gathering spaces--including a spacious Great Room, dedicated office, and light-filled Carolina Room--provide flexibility for everyday living and entertaining. The kitchen is appointed with custom Rutt cherry cabinetry, Sub-Zero refrigeration, Dacor double ovens, a five-burner gas cook top, generous workspace, and abundant storage. The main-level primary suite offers a spacious bath, walk-in closet, fireplace, and direct connection to the Carolina Room and outdoor living spaces. Outside, flagstone walkways, stone terraces, expansive lawn areas, and a brick fireplace courtyard create inviting spaces to enjoy the property's exceptional landscape. A detached 659-square-foot guest cottage with a bedroom, full bath, living area, and fireplace provides additional flexibility for guests, extended family, or a private workspace. A rare opportunity to own a significant Weymouth Heights property with privacy, character, and convenience in the heart of Southern Pines.

4 Beds ⋅ 4 Baths ⋅ 765723 MLS

Set on 3.21 private acres in Weymouth Heights, this 1924 estate offers architectural character, established gardens, and a detached guest cottage in one of Southern Pines' most treasured neighborhoods. Historic brick fencing lines portions of the drive, while mature pines, hardwoods, evergreens, and more than 300 flowering azaleas create a setting that has evolved beautifully over generations, just moments from downtown Southern Pines and Weymouth Woods. The 4-bedroom main residence blends thoughtful updates with original character, featuring hardwood floors, extensive mill work, custom built-ins, and four working fireplaces. Large windows frame views of the surrounding grounds, while multiple gathering spaces--including a spacious Great Room, dedicated office, and light-filled Carolina Room--provide flexibility for everyday living and entertaining. The kitchen is appointed with custom Rutt cherry cabinetry, Sub-Zero refrigeration, Dacor double ovens, a five-burner gas cook top, generous workspace, and abundant storage. The main-level primary suite offers a spacious bath, walk-in closet, fireplace, and direct connection to the Carolina Room and outdoor living spaces. Outside, flagstone walkways, stone terraces, expansive lawn areas, and a brick fireplace courtyard create inviting spaces to enjoy the property's exceptional landscape. A detached 659-square-foot guest cottage with a bedroom, full bath, living area, and fireplace provides additional flexibility for guests, extended family, or a private workspace. A rare opportunity to own a significant Weymouth Heights property with privacy, character, and convenience in the heart of Southern Pines.

285 N Bethesda Road NE, Southern Pines

Courtesy of EVERYTHING PINES PARTNERS LLC

$3,350,000

Welcome to Stone Oaks Farm, a remarkable private estate nestled on 6 beautifully landscaped acres in an exceptional location. Majestic old-growth oak trees frame the property, creating a stunning setting of natural beauty, privacy, and timeless elegance. The main residence offers more than 6,000 square feet of thoughtfully designed living space, complemented by an 802 square-foot guest suite above the garage featuring a full bath, steam shower, and sauna--perfect for extended family, guests, or a private retreat. Designed for both grand entertaining and comfortable everyday living, this home features 4 bedrooms and 3.5 baths, including an expansive formal dining room and a chef's kitchen equipped with dual islands, a six-burner Wolf gas cooktop, double ovens, a Sub-Zero refrigerator, and a butler's pantry with sink and additional dishwasher. A substantial 2005 addition introduced an extraordinary family room, private office, guest suite, and expanded primary living spaces. The stunning family room showcases exposed wood beams, hardwood floors, a wood-burning fireplace, and picturesque views of the outdoor entertaining areas. Adjacent to the family room is a sophisticated beverage center complete with a large wine refrigerator and beverage fridge. Beyond, a richly paneled executive library/office with its own fireplace provides the ultimate work-from-home environment. The main level also includes a spacious guest suite with a private bath. Upstairs, the luxurious primary suite offers dual walk-in closets and a spacious bath, while two additional bedrooms share a well-appointed full bath. Also added in 2025 is a beautifully outfitted entertainment and gaming space in the basement level complete with sink and wet bar. An ideal space for watching movies and sporting events. Outside, the estate continues to impress. A circular driveway and gated entrance welcome you to the property, while a three-car garage provides abundant storage. The backyard is designed for entertaining with a built-in grill, fire pit, and multiple outdoor gathering spaces including a beautiful stone koi pond. Beyond the immediate grounds, additional acreage offers unmatched privacy and includes a barn ideal for equipment, recreational vehicles, hobbies, or storage. This portion of the property may be subdivided if the owner so chooses. Completely fenced and meticulously maintained, Stone Oaks Farm presents a rare opportunity to own a private estate where luxury, comfort, and acreage come together in perfect harmony.

4 Beds ⋅ 4 Baths ⋅ 100584270 MLS

Welcome to Stone Oaks Farm, a remarkable private estate nestled on 6 beautifully landscaped acres in an exceptional location. Majestic old-growth oak trees frame the property, creating a stunning setting of natural beauty, privacy, and timeless elegance. The main residence offers more than 6,000 square feet of thoughtfully designed living space, complemented by an 802 square-foot guest suite above the garage featuring a full bath, steam shower, and sauna--perfect for extended family, guests, or a private retreat. Designed for both grand entertaining and comfortable everyday living, this home features 4 bedrooms and 3.5 baths, including an expansive formal dining room and a chef's kitchen equipped with dual islands, a six-burner Wolf gas cooktop, double ovens, a Sub-Zero refrigerator, and a butler's pantry with sink and additional dishwasher. A substantial 2005 addition introduced an extraordinary family room, private office, guest suite, and expanded primary living spaces. The stunning family room showcases exposed wood beams, hardwood floors, a wood-burning fireplace, and picturesque views of the outdoor entertaining areas. Adjacent to the family room is a sophisticated beverage center complete with a large wine refrigerator and beverage fridge. Beyond, a richly paneled executive library/office with its own fireplace provides the ultimate work-from-home environment. The main level also includes a spacious guest suite with a private bath. Upstairs, the luxurious primary suite offers dual walk-in closets and a spacious bath, while two additional bedrooms share a well-appointed full bath. Also added in 2025 is a beautifully outfitted entertainment and gaming space in the basement level complete with sink and wet bar. An ideal space for watching movies and sporting events. Outside, the estate continues to impress. A circular driveway and gated entrance welcome you to the property, while a three-car garage provides abundant storage. The backyard is designed for entertaining with a built-in grill, fire pit, and multiple outdoor gathering spaces including a beautiful stone koi pond. Beyond the immediate grounds, additional acreage offers unmatched privacy and includes a barn ideal for equipment, recreational vehicles, hobbies, or storage. This portion of the property may be subdivided if the owner so chooses. Completely fenced and meticulously maintained, Stone Oaks Farm presents a rare opportunity to own a private estate where luxury, comfort, and acreage come together in perfect harmony.

1680 Midland Rd, Southern Pines

Courtesy of Pines Sotheby's International Realty

$895,000

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.

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

$1,375,000

Set on 3.21 private acres in Weymouth Heights, this 1924 estate offers architectural character, established gardens, and a detached guest cottage in one of Southern Pines' most treasured neighborhoods. Historic brick fencing lines portions of the drive, while mature pines, hardwoods, evergreens, and more than 300 flowering azaleas create a setting that has evolved beautifully over generations, just moments from downtown Southern Pines and Weymouth Woods. The 4-bedroom main residence blends thoughtful updates with original character, featuring hardwood floors, extensive mill work, custom built-ins, and four working fireplaces. Large windows frame views of the surrounding grounds, while multiple gathering spaces--including a spacious Great Room, dedicated office, and light-filled Carolina Room--provide flexibility for everyday living and entertaining. The kitchen is appointed with custom Rutt cherry cabinetry, Sub-Zero refrigeration, Dacor double ovens, a five-burner gas cook top, generous workspace, and abundant storage. The main-level primary suite offers a spacious bath, walk-in closet, fireplace, and direct connection to the Carolina Room and outdoor living spaces. Outside, flagstone walkways, stone terraces, expansive lawn areas, and a brick fireplace courtyard create inviting spaces to enjoy the property's exceptional landscape. A detached 659-square-foot guest cottage with a bedroom, full bath, living area, and fireplace provides additional flexibility for guests, extended family, or a private workspace. A rare opportunity to own a significant Weymouth Heights property with privacy, character, and convenience in the heart of Southern Pines.

4 Beds ⋅ 4 Baths ⋅ 100583485 MLS

Set on 3.21 private acres in Weymouth Heights, this 1924 estate offers architectural character, established gardens, and a detached guest cottage in one of Southern Pines' most treasured neighborhoods. Historic brick fencing lines portions of the drive, while mature pines, hardwoods, evergreens, and more than 300 flowering azaleas create a setting that has evolved beautifully over generations, just moments from downtown Southern Pines and Weymouth Woods. The 4-bedroom main residence blends thoughtful updates with original character, featuring hardwood floors, extensive mill work, custom built-ins, and four working fireplaces. Large windows frame views of the surrounding grounds, while multiple gathering spaces--including a spacious Great Room, dedicated office, and light-filled Carolina Room--provide flexibility for everyday living and entertaining. The kitchen is appointed with custom Rutt cherry cabinetry, Sub-Zero refrigeration, Dacor double ovens, a five-burner gas cook top, generous workspace, and abundant storage. The main-level primary suite offers a spacious bath, walk-in closet, fireplace, and direct connection to the Carolina Room and outdoor living spaces. Outside, flagstone walkways, stone terraces, expansive lawn areas, and a brick fireplace courtyard create inviting spaces to enjoy the property's exceptional landscape. A detached 659-square-foot guest cottage with a bedroom, full bath, living area, and fireplace provides additional flexibility for guests, extended family, or a private workspace. A rare opportunity to own a significant Weymouth Heights property with privacy, character, and convenience in the heart of Southern Pines.

285 N Bethesda Rd, Southern Pines

Courtesy of Everything Pines Partners LLC

$1,145,000

Originally built in 1952 and thoughtfully expanded and renovated in 2001, Maplewood Cottage seamlessly blends historic character with the comfort, functionality, and spaciousness of modern living. Complemented by a fully furnished detached guest house, the property offers a rare combination of flexible living space, privacy, and timeless appeal within Southern Pines' coveted Weymouth Heights Historic District. The 2001 expansion added 1,562 square feet while extensively re-imagining the original residence, preserving the neighborhood's architectural character while creating a home designed for the way people live today. Set on 1.68 beautifully landscaped acres, the single level residence offers 2,932 square feet with five bedrooms, multiple gathering spaces, and a seamless connection between indoor and outdoor living. Just beyond the front entry, an inviting sitting room gives way to the expansive great room and adjoining Carolina room, where vaulted ceilings, walls of windows, exposed brick accents, and French doors frame views of the surrounding pines and create an effortless connection between the home's principal living spaces. At the heart of the home, the kitchen balances timeless design with everyday functionality, featuring stone countertops, a ceramic tile backsplash, a Bertazzoni gas range, a generous center island, and an adjoining butler's pantry complete with a wet bar, additional storage, and serving space. The primary suite serves as a private retreat with custom armoire style storage, a striking fireplace feature wall, dual vanities, and a spacious walk in shower. Natural light fills the home through expansive windows that continually draw the outdoors inside. Brick patios, winding garden paths, mature landscaping, and a large fenced backyard create multiple destinations for relaxing or entertaining. A separate white picket enclosed garden accented with copper capped fencing adds another layer of charm, while the private hot tub patio extends directly from the primary suite beneath the canopy of mature trees. Above the detached two car garage, the fully furnished 479 square foot guest house offers exceptional flexibility with a kitchenette, full bath, and open living area ideal for guests, multi-generational living, a private office, or income producing opportunities. Located moments from the shops and restaurants of historic downtown Southern Pines and the scenic trails of Weymouth Woods, this exceptional property combines the charm of a historic neighborhood with the comfort and flexibility of a thoughtfully expanded home. Opportunities to own 1.68 acres with a detached guest house, generous living spaces, and this level of privacy within Weymouth Heights are exceptionally rare.

5 Beds ⋅ 4 Baths ⋅ 100579198 MLS

Originally built in 1952 and thoughtfully expanded and renovated in 2001, Maplewood Cottage seamlessly blends historic character with the comfort, functionality, and spaciousness of modern living. Complemented by a fully furnished detached guest house, the property offers a rare combination of flexible living space, privacy, and timeless appeal within Southern Pines' coveted Weymouth Heights Historic District. The 2001 expansion added 1,562 square feet while extensively re-imagining the original residence, preserving the neighborhood's architectural character while creating a home designed for the way people live today. Set on 1.68 beautifully landscaped acres, the single level residence offers 2,932 square feet with five bedrooms, multiple gathering spaces, and a seamless connection between indoor and outdoor living. Just beyond the front entry, an inviting sitting room gives way to the expansive great room and adjoining Carolina room, where vaulted ceilings, walls of windows, exposed brick accents, and French doors frame views of the surrounding pines and create an effortless connection between the home's principal living spaces. At the heart of the home, the kitchen balances timeless design with everyday functionality, featuring stone countertops, a ceramic tile backsplash, a Bertazzoni gas range, a generous center island, and an adjoining butler's pantry complete with a wet bar, additional storage, and serving space. The primary suite serves as a private retreat with custom armoire style storage, a striking fireplace feature wall, dual vanities, and a spacious walk in shower. Natural light fills the home through expansive windows that continually draw the outdoors inside. Brick patios, winding garden paths, mature landscaping, and a large fenced backyard create multiple destinations for relaxing or entertaining. A separate white picket enclosed garden accented with copper capped fencing adds another layer of charm, while the private hot tub patio extends directly from the primary suite beneath the canopy of mature trees. Above the detached two car garage, the fully furnished 479 square foot guest house offers exceptional flexibility with a kitchenette, full bath, and open living area ideal for guests, multi-generational living, a private office, or income producing opportunities. Located moments from the shops and restaurants of historic downtown Southern Pines and the scenic trails of Weymouth Woods, this exceptional property combines the charm of a historic neighborhood with the comfort and flexibility of a thoughtfully expanded home. Opportunities to own 1.68 acres with a detached guest house, generous living spaces, and this level of privacy within Weymouth Heights are exceptionally rare.

305 Maples Rd, Southern Pines

Courtesy of Everything Pines Partners LLC

$2,495,000

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 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

$2,495,000

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 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

$499,000

$6,000 Price Improvement! Welcome home to a hidden treasure in the heart of Downtown Southern Pines! The character and vibe of this 1930's cottage says it all from the original hardwood & brick floors to the craftsmanship of the Heart Pine wood-paneled LR walls, built-ins, rustic wood beams and slate roofs! The detached third-bedroom guest cottage offers a full bath, refrigerator & storage with privacy for family and guests. Perfect space for multipurpose use or an in-law suite! The charming main cottage offers 2 spacious BR's, each with walk in closets. A hallway butler's pantry houses kitchen items and other storage needs. Charming dining room overlooks a landscape filled with delightful seasonal colors and sounds! Outdoor living is an absolute treat on the spacious screened porch with quick access to living, dining and kitchen. Relax by the warmth of a natural gas fireplace, surrounded by cozy Heart Pine wood paneled living room walls. New energy efficient windows are found throughout the home! A secret English garden will delight your senses...where snapdragons keep company with ripening tomatoes on the vine. The home's gardens and lawn are beautifully maintained with an irrigation system throughout the landscape. Original brick lattice fencing frame heritage plantings, flowers and flowering shrubs and trees. Raised planting beds with young plants await summer's bountiful harvest. Enjoy an ever changing backdrop of lovely smells, colors and the sounds of nature from an inviting screened porch. A privacy fence surrounds the landscaped yard and detached storage shed, perfect for garden and/or workshop space. A brick lattice wall anchors the newer brick patio and was created to preserve the character of the original brick lattice fencing. Ample parking includes a circle drive and side parking for both the main & guest cottages! Enjoy all the conveniences of living within the vibrant Downtown community where shopping, restaurants and parks are just minutes away! Call for your personal tour of this unique property today! You'll leave with a feeling of home!

3 Beds ⋅ 2 Baths ⋅ 100563447 MLS

$6,000 Price Improvement! Welcome home to a hidden treasure in the heart of Downtown Southern Pines! The character and vibe of this 1930's cottage says it all from the original hardwood & brick floors to the craftsmanship of the Heart Pine wood-paneled LR walls, built-ins, rustic wood beams and slate roofs! The detached third-bedroom guest cottage offers a full bath, refrigerator & storage with privacy for family and guests. Perfect space for multipurpose use or an in-law suite! The charming main cottage offers 2 spacious BR's, each with walk in closets. A hallway butler's pantry houses kitchen items and other storage needs. Charming dining room overlooks a landscape filled with delightful seasonal colors and sounds! Outdoor living is an absolute treat on the spacious screened porch with quick access to living, dining and kitchen. Relax by the warmth of a natural gas fireplace, surrounded by cozy Heart Pine wood paneled living room walls. New energy efficient windows are found throughout the home! A secret English garden will delight your senses...where snapdragons keep company with ripening tomatoes on the vine. The home's gardens and lawn are beautifully maintained with an irrigation system throughout the landscape. Original brick lattice fencing frame heritage plantings, flowers and flowering shrubs and trees. Raised planting beds with young plants await summer's bountiful harvest. Enjoy an ever changing backdrop of lovely smells, colors and the sounds of nature from an inviting screened porch. A privacy fence surrounds the landscaped yard and detached storage shed, perfect for garden and/or workshop space. A brick lattice wall anchors the newer brick patio and was created to preserve the character of the original brick lattice fencing. Ample parking includes a circle drive and side parking for both the main & guest cottages! Enjoy all the conveniences of living within the vibrant Downtown community where shopping, restaurants and parks are just minutes away! Call for your personal tour of this unique property today! You'll leave with a feeling of home!

370 E Morganton Rd, Southern Pines

Courtesy of Sandhill Realty/Aberdeen

$636,000

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.

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

$185,500

Awesome corner Lot in Mid South Club bordering the Mid South Golf Course. Golf views of the 15th hole . Nice topography with gentle slope. This lot allows for flexibility in home design. No time frame to build and club membership can be activated upon closing with NO WAIT!! Mid Tal Golf Membership available thru the Membership office with the payment of applicable transfer fee and dues. Talamore and Mid-South are under one membership!! Club amenities are only allowed access with membership. Membership can include a full golf or a social membership. 2 superb golf courses (Arnold Palmer at Mid-South and the Rees Jones designed course at Talamore), 2 clubhouses, 2 pools and tennis. Features include a gated golf course community with 24 hour security, 2 gates and private roads. Community Internet and Cablevision thru Spectrum included with community discounted rate! See MidSouthPOA.com for community documents and ARB guidelines. The Southern Pines Greenway access is just outside the gate for walking, jogging or riding bikes. Close to shopping, schools, hospital and area amenities. Easy commute to Raleigh or Ft. Bragg! This is a great community so don't miss this opportunity to own one of the last few ''Custom Home '' lots available.

100423224 MLS

Awesome corner Lot in Mid South Club bordering the Mid South Golf Course. Golf views of the 15th hole . Nice topography with gentle slope. This lot allows for flexibility in home design. No time frame to build and club membership can be activated upon closing with NO WAIT!! Mid Tal Golf Membership available thru the Membership office with the payment of applicable transfer fee and dues. Talamore and Mid-South are under one membership!! Club amenities are only allowed access with membership. Membership can include a full golf or a social membership. 2 superb golf courses (Arnold Palmer at Mid-South and the Rees Jones designed course at Talamore), 2 clubhouses, 2 pools and tennis. Features include a gated golf course community with 24 hour security, 2 gates and private roads. Community Internet and Cablevision thru Spectrum included with community discounted rate! See MidSouthPOA.com for community documents and ARB guidelines. The Southern Pines Greenway access is just outside the gate for walking, jogging or riding bikes. Close to shopping, schools, hospital and area amenities. Easy commute to Raleigh or Ft. Bragg! This is a great community so don't miss this opportunity to own one of the last few ''Custom Home '' lots available.

115 Kings Ridge Ct, Southern Pines

Courtesy of Front Runner Realty Group

Buyer Representative Pine & Palm Real Estate Group

$620,000

This beautifully maintained 3-bedroom, 2.5-bath brick home is situated on a well-landscaped lot overlooking the second hole of the Talamore Golf Resort. Offering a blend of classic elegance and modern updates, this home is filled with fine architectural details including crown molding, ornate woodwork and chair rail trim to name a few. Step into the foyer with an arched entry leading to a breathtaking library/study featuring soaring ceilings, custom wood-stained cabinetry with built-in bookcases, a rolling ladder, and Palladian window. The spacious, light-filled living room boasts vaulted ceilings and a wall of windows that frame expansive golf course views, seamlessly flowing into the dining area with tree tall arched windows and gourmet kitchen. The kitchen features beautiful white cabinetry, quartz countertops, stainless steel appliances, a double wall oven, and electric cooktop—perfect for entertaining or everyday living. The secluded primary suite offers a luxurious retreat with a bay window wall, private access to the back deck, tray ceiling, and ceiling fan. The newly remodeled ensuite bath (2024) features a double-sink vanity, freestanding soaking tub, curbless shower, private water closet, and a large walk-in closet. Two additional bedrooms are connected by a stylishly updated Jack-and-Jill bathroom. Other highlights include a large unfinished, floored attic with permanent stairs—ideal for storage or future expansion. Recent upgrades include a new roof (2022), new HVAC system (2023), remodeled bathrooms (2024), a new hot water heater (2022), a new deck (2024), and extensive landscaping with an upgraded irrigation system. Located in a desirable neighborhood just minutes from the Village of Pinehurst and downtown Southern Pines, this home offers the perfect combination of tranquility, luxury, and convenience. Impeccably maintained and move-in ready—this is Southern living at its finest!

3 Beds ⋅ 3 Baths ⋅ 100511831 MLS

This beautifully maintained 3-bedroom, 2.5-bath brick home is situated on a well-landscaped lot overlooking the second hole of the Talamore Golf Resort. Offering a blend of classic elegance and modern updates, this home is filled with fine architectural details including crown molding, ornate woodwork and chair rail trim to name a few. Step into the foyer with an arched entry leading to a breathtaking library/study featuring soaring ceilings, custom wood-stained cabinetry with built-in bookcases, a rolling ladder, and Palladian window. The spacious, light-filled living room boasts vaulted ceilings and a wall of windows that frame expansive golf course views, seamlessly flowing into the dining area with tree tall arched windows and gourmet kitchen. The kitchen features beautiful white cabinetry, quartz countertops, stainless steel appliances, a double wall oven, and electric cooktop—perfect for entertaining or everyday living. The secluded primary suite offers a luxurious retreat with a bay window wall, private access to the back deck, tray ceiling, and ceiling fan. The newly remodeled ensuite bath (2024) features a double-sink vanity, freestanding soaking tub, curbless shower, private water closet, and a large walk-in closet. Two additional bedrooms are connected by a stylishly updated Jack-and-Jill bathroom. Other highlights include a large unfinished, floored attic with permanent stairs—ideal for storage or future expansion. Recent upgrades include a new roof (2022), new HVAC system (2023), remodeled bathrooms (2024), a new hot water heater (2022), a new deck (2024), and extensive landscaping with an upgraded irrigation system. Located in a desirable neighborhood just minutes from the Village of Pinehurst and downtown Southern Pines, this home offers the perfect combination of tranquility, luxury, and convenience. Impeccably maintained and move-in ready—this is Southern living at its finest!

24 Mcnish Rd, Southern Pines

Courtesy of The Gentry Team

Buyer Representative Coldwell Banker Advantage-Southern Pines