Southern Pines Homes with Two Levels

Welcome to Southern Pines, North Carolina—a charming town nestled in the heart of Moore County. Known for its rich history, vibrant community, and stunning natural beauty, Southern Pines offers an exceptional quality of life that attracts families, retirees, and everyone in between. With its picturesque tree-lined streets and welcoming neighborhoods, this area is a true gem of the Sandhills region.

One of the standout features of Southern Pines is its diverse selection of homes, particularly those with two levels. These multi-story residences provide an ideal blend of space and comfort, perfect for both entertaining and everyday living. Whether you’re seeking a cozy family home or a spacious retreat, Southern Pines boasts a variety of architectural styles that cater to every taste. The two-level homes often feature open floor plans, allowing for seamless transitions between living spaces, while also providing the privacy of separate bedrooms and offices on upper levels.

Beyond the homes themselves, Southern Pines is a community that embraces an active lifestyle. Residents enjoy access to beautiful parks, golf courses, and outdoor recreational activities, making it easy to connect with nature and stay active. The downtown area is filled with charming boutiques, delightful eateries, and cultural attractions, ensuring that there’s always something to explore.

If you’re looking for a place that combines the warmth of a small town with the amenities of modern living, Southern Pines is the perfect destination. Discover your dream two-level home in this enchanting community today, and experience the Southern Pines lifestyle for yourself!

Newest Southern Pines Homes with Two Levels

$324,000

3 Beds ⋅ 3 Baths ⋅ 100586732 MLS

Step into modern comfort with this beautifully maintained 2022 home featuring 3 bedrooms, 2.5 bathrooms, and a 2-car garage. Conveniently located minutes from Southern Pines shopping, dining, schools, and entertainment. The open-concept main level features a spacious living room that flows seamlessly into the dining area and kitchen. The eat-in kitchen offers stainless steel appliances, granite countertops, ample cabinet space and a pantry for additional storage. Upstairs, you'll find all three bedrooms, including a comfortable primary suite, along with the convenience of a second-floor laundry area. Outside, enjoy a large rear deck overlooking the fully fenced backyard. Enjoy the freedom of no HOA. Schedule your showing today!

645 S Gaines St, Southern Pines

Listing courtesy of Everything Pines Partners Sanford.

$799,000

5 Beds ⋅ 4 Baths ⋅ 100580821 MLS

Life in downtown Southern Pines is all about convenience, connection, and charm, and 460 N. May Street places you right in the heart of it. Just moments from local restaurants, coffee shops, boutiques, parks, and community events, this nearly new home offers the rare opportunity to enjoy a walkable downtown lifestyle without sacrificing space. Built just two years ago, this beautifully designed five-bedroom, four-bathroom home offers more than 2,600 square feet of thoughtfully planned living space. Filled with natural light and warm, inviting finishes, the home combines timeless style with the flexibility today's lifestyles demand. The open-concept main living area features engineered hardwood flooring, Visual Comfort lighting, and seamless flow between the living, dining, and kitchen spaces. The kitchen is both beautiful and functional, showcasing white cabinetry, a contrasting wood-tone island, quartz countertops, stainless steel appliances, a gas range with decorative hood, and a generous walk-in pantry. One of the home's most desirable features is its flexible first-floor layout. The spacious primary suite is conveniently located on the main level and includes a walk-in closet customized by Closets by Design along with a well-appointed bath featuring dual vanities, a fully tiled shower, and linen storage. A second bedroom and full bath on the main level offer excellent accommodations for guests, currently staged as an office and provides the flexibility for a guest room, workspace, or multi-generational living arrangement. Upstairs, you'll find 3 additional bedrooms and 2 full bathrooms, including a versatile room currently styled as a moody media space, perfect for movie nights, gaming, or a private retreat. Practical features abound, including a laundry room with built-in cabinetry, folding counter, and storage, an encapsulated crawlspace with commercial-grade dehumidifier, detached garage for additional storage, ample parking along the extended concrete driveway, and a screened porch that invites year-round enjoyment. New sod was installed last year, and a private paver patio behind the garage creates the perfect setting for grilling and outdoor gatherings. In a downtown market where homes with five true bedrooms are exceptionally rare, 460 N. May Street stands apart by offering the space, flexibility, and modern amenities so many buyers are searching for, all in one of Southern Pines' most sought-after locations. This is downtown living at its finest: close to everything, beautifully maintained, and designed for the way you live today.

460 N May St, Southern Pines

Listing courtesy of Keller Williams Pinehurst.

$319,000

3 Beds ⋅ 3 Baths ⋅ 100556040 MLS

Just minutes from downtown Southern Pines, this stunning new build offers incredible value! Featuring luxury vinyl plank (LVP) flooring throughout the main level, sleek granite countertops, and an attached garage, this home perfectly blends style and functionality. Enjoy the convenience of modern living in a prime location--all at a fantastic price! Ask about our preferred lender incentives!!!

565 S Glover St, Southern Pines

Listing courtesy of Carolina Summit Group, LLC.

Start Your Search

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.