Old Town Real Estate

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Newest Listings in Old Town

$2,495,000

5 Beds ⋅ 6 Baths

''Blinkbonnie'' located in one of Pinehurst's most desirable neighborhoods, Old Town, was built by Simon B. Chapin,a New York financier and philanthropist. Mr. Chapin built five other cottages in Pinehurst during his time. Chapin was also credited with developing Myrtle beach, S.C. ''Blinkbonnie'' ,a popular name for 18th century estates in Scotland, conveyed a sense of charm, pastoral beauty and peace. Built in 1917, a formative period of Pinehurst's development, 50 McCaskill Rd is a fine example of the architecture and lifestyle that defined OLD TOWN in the early 1900s. Close to the Village shops, Carolina Hotel and Pinehurst Country Club, this 1.018 acre lot is full of old world charm. Upon entering the foyer, an exquisite living room with a stunning wood burning fireplace awaits. The sunny, elegant dining room entertains easily for small or large gatherings. The Carolina Sunroom boasts French doors, an oversized curved bay window, and a view overlooking pool area, Large den at end of hallway, can convert to 5th bedroom if desired. Kitchen has Subzero refrigerator, double Viking oven, 6 gas burner stove, large island. Butlers pantry has built in glass door cabinetry, lockable liquor cabinet and wine cooler. Easy access to kitchen and garage, first floor mudroom has washer, dryer, cubbies, and closet. Downstairs, a finished basement with rec room, kitchenette, mini fridge, ice maker, dishwasher, pool table, large closets. Media room has TV, full bath, closets, restaurant size walk in refrigerator. Upstairs, a beautiful staircase leads to 4 bedrooms, all with ensuite baths. Light and airy master bedroom has private sitting room, multiple closets and large bathroom. Library sits at the end of hallway with fireplace.Mature landscaping and vintage iron gates lead to brick and blue stone pathways, a tranquil French garden, fenced in area for dog park. Classic rectangular POOL (20x45) and POOL HOUSE with sauna, wet bar, wood smoker grill, full bath. GENERATOR

50 Mccaskill Rd W, Pinehurst

$1,275,000

4 Beds ⋅ 4 Baths

Pinehurst ''New Construction'' in OLD TOWN. WALK TO PINEHURST ELEMENTARY SCHOOL! Seller to consider OWNER FINANCING. Call listing agent for details. One block from the new Pinehurst Elementary School and less than one mile from the Historic Village of Pinehurst. Great old town location near Rassie Wicker Park, walking trails, ball fields and summer splash pad. Stunning new construction with all the features buyers demand - open floorpan, pre-finished 3/4 inch solid Brazilian hardwood, plantation shutters, cooks kitchen, high end appliances, quartz countertop and more. Handsome fireplace with slate surround is the focal point of the main living area. Utility room has a reclaimed sink from the original house on the property plus a slate countertop. Screened porch off the kitchen with access to very large fenced back yard. First floor master bedroom with walk-in closet and wood shelving, plus heated floors and quartz countertop in Master bath. Second bedroom on the first floor with full bath. Upstairs there are two more ensuite bedrooms and large bonus room/game room. Pool table and card table convey. Home has natural gas.

30 Medlin Rd, Pinehurst

$849,750

Rare opportunity to own a beautiful building lot in a prime Pinehurst location! Situated on the well-known and highly desirable Donald Ross Drive, this gorgeous lot offers the perfect setting to build your dream home in the heart of the Village of Pinehurst. Opportunities like this don't come along often, especially in such a sought-after location! Enjoy the charm, character, and convenience of Village living while creating a home that's truly your own. An incredible opportunity to build in one of Pinehurst's most desirable locations!

555 Donald Ross Dr, Pinehurst

$899,000

4 Beds ⋅ 4 Baths

Historic Pinehurst property with exceptional character and an opportunity for restoration in the heart of Old Town. Located within the Pinehurst Historic District, this spacious two-story residence offers approximately 3,600+ square feet, four bedrooms, three full baths and one half bath on approximately .62 acres encompassing Lots 210-A and 210-B. The home retains many of the architectural details and features that reflect its history, including wood flooring, fireplaces, generous living and dining spaces, and a large Carolina/sunroom. A detached garage and established landscaping add to the property's potential. This is a substantial home in need of repairs, updating, and general deferred maintenance. Please note that part of living room ceiling is damaged. Conveniently located near the Village of Pinehurst, local shops, restaurants and Pinehurst Resort. Sale is subject to court approval.

15 Mccaskill Rd W, Pinehurst

$254,900

3 Beds ⋅ 2 Baths

Beautifully renovated 3-bedroom, 2-bath home in SoGlo Historic Old Town! This move-in-ready home blends original character with modern updates, featuring refinished original hardwood floors, a NEW ROOF, fresh interior and exterior paint, renovated bathrooms, and a completely renovated kitchen with new cabinets, countertops, and appliances. Enjoy the screened-in front porch and second-floor balcony that preserve the home's classic Southern charm. Located in the desirable Old Town area near highly rated schools and just minutes from downtown dining, shopping, entertainment, and waterfront attractions. Historic character, modern updates, and an incredible location—all in one home.

507 1st Ave, Brunswick

$1,530,000

4 Beds ⋅ 4 Baths

LOCATION, CHARM & LIFESTYLE in the heart of Old Town Pinehurst! Just steps from the iconic Pinehurst Hotel, Spa, historic district, and an inviting collection of shops, pubs, and restaurants. For the golf enthusiast, hop in your golf cart and head to the first tee of Pinehurst Courses No. 1-5--a truly exceptional village lifestyle. This charming and thoughtfully updated home features spacious, open rooms with an effortless flow that is ideal for both everyday living and entertaining. The inviting living room is anchored by a beautiful stone fireplace, while the Carolina Room provides a warm, sunny gathering space filled with natural light. French doors open to the deck, extending the living experience outdoors to enjoy morning coffee, casual gatherings, or evening entertaining in a private setting. The luxurious primary suite is designed for comfort and convenience, featuring a large walk-in shower and elegant double vanity. For exceptional convenience the adjoining laundry room connects directly to the kitchen, creating a seamless and highly functional flow rarely found in a home of this character. The lower level has an additional 448 heated square footage not counted in the total square footage of the home. The lower level adds an incredible dimension to the home, featuring a 2-car garage plus a heated and cooled recreation room and separate office, providing abundant space for hobbies, projects, guests, or additional entertaining. The golf cart garage bay is an especially desirable amenity for enjoying Pinehurst's renowned golf and village lifestyle. Pinehurst CC membership available for transfer with buyer to pay prevailing transfer and applicable membership fees. With its enviable walkable location, charming character, stylish updates, generous living spaces, and exceptional garage and recreation areas, this is a rare opportunity to own a home in one of Pinehurst's most sought-after locations.

12 Village Ln, Pinehurst

$1,150,000

3 Beds ⋅ 4 Baths

Nestled in the heart of the charming Historic Village of Pinehurst, this stunning home offers an unparalleled level of privacy and tranquility. Accessed via a secluded pea gravel driveway, this property spans over an acre of lush land providing a serene location for this beautifully renovated cottage. Surrounded by mature landscaping, this home boasts a remote setting that feels like a retreat, yet remains close to the village's rich culture and amenities only being a golf cart ride away. The spacious grounds are perfect for gardening, outdoor entertaining or simply enjoying the peaceful surroundings on one of the outdoor patio areas. Step inside to find a thoughtfully designed and meticulously remodeled interior that blends modern comforts with timeless elegance. With gorgeous engineered hardwoods on the main level, you will find spacious living areas with large windows that invite in natural light. There are two wood-burning fireplaces with one being in the den/family room and the other in the formal living area. Downstairs you will find two ensuite bedrooms with generous closets and beautifully tiled bathrooms. The kitchen has all new Forno appliances, leathered granite countertops with modern black subway tile. There are also two pantry storage closets, a half bath and large laundry area accessible from the detached two car garage with breezeway. Upstairs you will find a bonus room area which can also be a full guest suite complete with sitting area, walk-in closet and large bathroom, all of which was recently added making the total living space over 3500 sqft!! Full list of updates provided in documents. Whether you're looking for a weekend getaway or a permanent residence, this property in Pinehurst is a rare gem that offers the perfect balance of seclusion and convenience. Don't miss the opportunity to make this private sanctuary your own!

180 Frye Rd, Pinehurst

$3,500,000

Historic Downtown Pinehurst Investment Opportunity Located in the heart of downtown Pinehurst, 15 Chinquapin Road presents a unique opportunity to own a historic commercial property with a strong tenant mix and 100% occupancy. Originally built in 1921 for the Bank of Pinehurst, the ±9,500 SF building offers a distinctive combination of historic character and established commercial use. The property spans four levels, including a basement, two primary commercial floors, and a potential third-floor space that could accommodate future commercial or residential use. The current tenant mix includes retail, service, and office uses, with established tenants including Agora Bakery and Cafe, Form V Chocolates, Harlow A Lux Salon, and Moore County Economic Development Partnership. With its historic significance, downtown location, diverse tenant mix, and full occupancy, 15 Chinquapin Road offers an exceptional opportunity for an investor seeking a distinctive commercial property in Pinehurst.

15 Chinquapin Rd, Pinehurst

$1,549,000

4 Beds ⋅ 3 Baths

Welcome to "Sweet Bay Cottage" in the Village of Pinehurst where history, elegance, and the good life converge. This stunning new construction home, built by award-winning third-generation builder and developer F. Calvin Riddle, Jr., offers 2,742 square feet of thoughtfully designed living space, four bedrooms, and three full bathrooms. Clad in fiber cement shake and lap siding, this beautifully proportioned New England Cottage-style home fits naturally and gracefully into the historic streetscape of the Village, a fitting nod to the New England resort heritage that gave Pinehurst its very soul. Two bedrooms and bathrooms on the main floor offer convenient and comfortable single-level living, while two additional bedrooms upstairs each enjoy private access to a dedicated full bath and sitting room. Wide-plank wood floors flow throughout the majority of the main level, lending warmth and enduring character at every turn. The kitchen is anchored by a natural gas range, while a natural gas fireplace in the living room sets the perfect scene for cozy Sandhills evenings. Comfort and efficiency are built in from the ground up: a natural gas furnace serves to heat the main level, an electric heat pump handles the upper level, and a tankless natural gas water heater ensures timely hot water throughout. Step through to the screened porch, accessible from the living room, and you will find the ideal setting for morning coffee, alfresco entertaining, or simply listening to the whisper of the pines. A two-car detached garage completes the property, tucked discreetly behind the home in keeping with the Village's traditional and refined character. Established in 1895 and master planned by Frederick Law Olmsted, the legendary landscape architect behind Central Park, the Village of Pinehurst was conceived as a gracious retreat whose winding roads and timeless cottages remain to this day. In 1996, the Village earned designation as a National Historic Landmark, the first golf resort and community ever to receive the honor. Residents enjoy navigating the village's storied streets by golf cart, strolling beneath longleaf pines, and savoring a lifestyle rooted in tradition and world-class recreation, all just steps from the Pinehurst Country Club and its iconic Course #2, confirmed anchor site for the 2029 Back-to-Back Men's and Women's U.S. Open and the 2035, 2041, and 2047 Men's U.S. Opens. A transferable PCC charter membership is available for the buyer to pay the initiation fee and subsequent monthly dues. Buyer to transfer membership within 60 days of closing.

275 Magnolia Rd, Pinehurst

$2,245,000

4 Beds ⋅ 6 Baths

Introducing The Mayflower Cottage, circa 1917--a timeless gem exuding relaxed elegance and historic charm. Set on 1.15 acres at the corner of Linden Road and McCaskill Rd. W in Old Town, the main residence spans over 4,400 square feet with 4 exquisite bedroom suites. Complementing this, a detached three-car garage with a charming guest cottage with over 880 sq.ft. oﬀers a bedroom suite, oﬃce, living area, and kitchen--a perfect retreat for quests or extended family. The gourmet kitchen, a chef's dream, boasts luxury stainless steel appliances,3 sinks, a breakfast bar, and a breakfast nook with a dedicated coﬀee bar. The formal dining room impresses with a coﬀered ceiling, and the expansive living room centers around a natural gas fireplace. Also on the first floor, you'll find a welcoming family room, a full bathroom, a powder room, and a spacious laundry room. The unfinished basement with a full dehumidifying system features a sauna and a wine cellar . The home features a hardwired full-house generator for peace of mind. This rare estate ,a sanctuary of timeless sophistication and modern comfort, invites you to embrace a serene yet sophisticated lifestyle in one of the most coveted neighborhoods. Access the property from the Linden Road or McCaskill Road driveways. There is a transferable Pinehurst Country Club membership-buyer to pay transfer fee.

55 Linden Rd, Pinehurst

$1,500

Executive office space available in the Harvard Building located in the Village of Pinehurst.

95 Market Sq, Pinehurst

$2,795,000

7 Beds ⋅ 10 Baths

Thistle Dhu is a celebrated Pinehurst landmark where American golf history and refined living converge. Built in 1919 by James Barber, this storied estate was home to the first 18-hole miniature golf course in the United States, with original holes still visible today, including one on the front lawn near the driveway. The name ''Thistle Dhu'' is a playful nod to Barber's admiring words upon completion: ''This'll do.'' Located in Olde Town Pinehurst, the property is just a short golf cart ride to Pinehurst Village, offering boutique shopping, dining, live entertainment, and the renowned Pinehurst Hotel & Spa. Thistle Dhu offers exceptional versatility as a primary residence, vacation home, or income-producing property. The estate may be utilized as a high-end Airbnb or short-term rental. The estate is ideal for hosting corporate retreats, family gatherings, and major golf events. Timeless and irreplaceable, Thistle Dhu remains one of Pinehurst's most iconic estates, where history lives on with modern luxury woven seamlessly throughout. The residence was extensively updated to modern standards while carefully preserving its original architectural character. The residence now features seven luxurious suites, including expansive owner's suites on both the main and upper levels with private living areas. The main level offers a gourmet kitchen with island and butler's pantry, breakfast nook, formal and casual dining spaces, a grand foyer, and elegant living and Carolina rooms that open to enclosed porches. Restored heart pine floors, original moldings, Palladian doors, and hand-carved staircases honor the home's historic character throughout. The lower level is designed for entertaining, featuring a recreation room with fireplace, a hidden speakeasy bar, movie theater, and ample storage. Outdoors, the 1.19 acre grounds include brick walkways, historic fountain, charming gazebo and gated entryways, creating a private garden retreat.

12 E Barrett Rd, Pinehurst

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Old Town Real Estate

Newest Listings in Old Town

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