Old Town Real Estate

Old Town Real Estate

Welcome to Old Town, a charming neighborhood nestled in the heart of Pinehurst, North Carolina, within the picturesque Moore County. Known for its rich history and serene ambiance, Old Town offers a unique blend of Southern charm and modern conveniences, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle.

As you stroll through the tree-lined streets of Old Town, you'll be captivated by the beautifully preserved homes that reflect the area's historical roots. Many of these residences boast classic architectural styles, complete with inviting front porches and lush gardens, creating a warm and welcoming atmosphere. The community is known for its strong sense of camaraderie, where neighbors greet each other with smiles and gatherings are a common occurrence.

Old Town is not just about its stunning homes; it also provides easy access to an array of amenities. The neighborhood is conveniently located near top-rated schools, vibrant shopping districts, and delightful dining options. Outdoor enthusiasts will appreciate the proximity to Pinehurst's renowned golf courses, scenic parks, and nature trails, perfect for leisurely walks or weekend picnics.

Cultural and recreational activities abound, with the historic Pinehurst Village just a short drive away, offering art galleries, local events, and seasonal festivities. Whether you're enjoying a quiet evening at home or exploring the vibrant community, Old Town promises a lifestyle filled with charm, comfort, and connection. Discover your dream home in this enchanting neighborhood, where every day feels like a getaway!

Newest Listings in Old Town

$625,000
2 Beds ⋅ 1 Baths ⋅ 100589352 MLS ⋅ ACTIVE Status ⋅ 1,156 SqFt. ⋅ 1966 Year Built
Perfectly positioned in the heart of Pinehurst, this beautifully updated 2-bedroom, 1-bath home offers timeless charm, modern updates and an unbeatable location. Situated on a desirable corner lot, the property features a fenced backyard and a spacious attached covered carport that doubles as an exceptional outdoor living space - ideal for relaxing, entertaining, or enjoying Carolina evenings. Inside, you will find warm hardwood floors throughout the bedrooms and living areas, abundant natural light, and a cozy living room centered around a fireplace. The updated kitchen features white cabinetry, stainless steel appliances, and ample cabinet space. The renovated bathroom offers a beautiful walk in shower with glass enclosure and modern vanity. A versatile bonus room provides the perfect space for a home office, den, fitness room, or hobby area. Outside, the fully fenced backyard offers privacy with plenty of room for pets, gardening, or outdoor gatherings. Conveniently located in the Village of Pinehurst, golf, dining, shopping and parks, this move-in ready home is ideal as a primary residence, second home, or investment opportunity.

85 Mcintyre Rd, Pinehurst
$1,549,000
4 Beds ⋅ 3 Baths ⋅ 100580260 MLS ⋅ ACTIVE Status ⋅ 2,742 SqFt. ⋅ 2026 Year Built
Welcome to 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
$768,000
4 Beds ⋅ 3 Baths ⋅ 100573731 MLS ⋅ ACTIVE Status ⋅ 2,006 SqFt. ⋅ 1979 Year Built
LOCATION IS EVERYTHING! Set in the heart of the Village of Pinehurst, this 4-bedroom, 3-bath home was completely renovated in 2021 and offers modern comfort in a highly desirable historic district setting. Just a short stroll to all of the restaurants and shopping the Village has to offer. Thoughtfully updated throughout, the home features a spacious split-bedroom layout with an inviting open living area centered around a wood-burning fireplace. The kitchen is beautifully designed with updated cabinetry, a large center island, quartz countertops, a tile backsplash, and stainless steel appliances. Hardwood floors extend through the main living areas and into the primary suite, adding warmth and character throughout. The generous primary suite includes an oversized walk-in tile shower, dual vanities, and a conveniently located closet near the laundry room. A private guest en suite provides added comfort and flexibility for visitors or extended stays. Out back, enjoy a deck overlooking the completely fenced backyard, offering a wonderful space for outdoor living, pets, play, or entertaining. With major systems including the roof, HVAC, plumbing, and electrical updated in 2021, this move-in-ready home delivers the feel of newer construction in one of Pinehurst's most charming and sought-after locations. Ask about our preferred lender credit.

5 Mcleod Rd, Pinehurst
$2,295,000
4 Beds ⋅ 5 Baths ⋅ 100571799 MLS ⋅ ACTIVE Status ⋅ 3,393 SqFt. ⋅ 1970 Year Built
ALL NEW WINDOWS, new stunning wood and glass double front doors. FULL VIEW OF PINEHURST NO 2, the famed Donald Ross masterpiece and site of the 2024 U.S. Open. Situated across the street from the first Green of the No 2 Course with full views of multiple fairways on this Historic course. Walk one hole on the golf cart trail to the 1st tee of No 2 and Pinehurst Country Club Main Clubhouse. Located two tenths of a mile from the quaint Village of Pinehurst with shops, pubs, restaurants, weekly farmer's market and year round events on the Green. Walk everywhere or take your golf cart! Home is situated on large lot with storybook Gazebo. Outdoor private patio, special collection of David Austin English roses, plus irrigated raised beds for the avid gardener. Inside home is totally updated with handsome fireplace in living room, formal dining room and kitchen open to bright family room with glass wall. Four ensuite bedrooms, plus office, plus wine room, plus powder room, with 2 master bedrooms. Large climate controlled garage with built in refrigerator and freezer (36'' each), and cabinetry completed in 2021. Purchase price based on recent appraisal. Will share with serious buyers who make an offer. Listing agent must be present for all showings.

55 Palmetto Rd, Pinehurst
$1,845,000
4 Beds ⋅ 4 Baths ⋅ 100571346 MLS ⋅ ACTIVE Status ⋅ 3,959 SqFt. ⋅ 2009 Year Built
Welcome to this beautifully designed home in the heart of historic Old Town Pinehurst, offering spacious living just minutes from the Village of Pinehurst with its shopping, dining, and local charm. The home is also within walking distance to Pinehurst Country Club, featuring world class golf, dining, pools, and fitness amenities. This thoughtfully designed residence features 4 bedrooms, 3.5 bathrooms, and a newly completed basement level that adds exceptional flexibility with additional guest space, a bedroom, and an entertainment area. Generous basement and attic storage provide room for everything. Inside, the main level offers a formal dining room, dedicated office or guest bedroom, and a private primary suite with trey ceilings, direct deck access, and a spa style bath featuring a walk in tiled shower, soaking tub, double vanity, and oversized walk in closet. The gourmet kitchen is equipped with a large island, gas cooktop, double wall ovens, walk in pantry, and abundant cabinetry. Sliding doors open to a screened porch overlooking the peaceful backyard. Upstairs, two additional bedrooms with walk in closets share a full bath and loft area overlooking the living room below. Fresh paint throughout the home and newly refinished hardwood floors allow this home to be move in ready. Outside, enjoy beautifully landscaped grounds, a spacious deck with screened and open areas, outdoor shower, and easy indoor outdoor living in one of Pinehurst's most desirable locations.

50 Dundee Rd, Pinehurst
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 100566358 MLS ⋅ ACTIVE Status ⋅ 2,800 SqFt. ⋅ 1975 Year Built
Extraordinary, all-brick home in the Village of Pinehurst showcasing exceptional upgrades and modern design throughout. Recent improvements include a new roof installed in January 2026. The gourmet kitchen features beautiful cabinetry, granite countertops, a butler's pantry, center island, and breakfast bar--all opening seamlessly to a spacious family room with fireplace. This single-level home offers a bright and open floor plan, elegant tray ceilings in the master, living, and family rooms, a formal dining room, Carolina Room with backyard views, two show-stopping full bathrooms and a powder room for guests. The stunning primary suite includes his-and-her walk-in closets and a luxurious bathroom with a tiled walk-in shower and soaking tub. Each additional bedroom is generously sized, and the home also includes a large laundry room/mud room, and an expansive deck perfect for entertaining. Situated on almost an acre only blocks to the Village shops and restaurants, parks, and trails. In addition to its outstanding features this house has successfully been rented the week of the US Open for @10k. Transferrable PCC membership is available.

30 Dalrymple Rd, Pinehurst
$2,245,000
4 Beds ⋅ 6 Baths ⋅ 100558617 MLS ⋅ ACTIVE Status ⋅ 5,286 SqFt. ⋅ 1917 Year Built
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
$1,275,000
4 Beds ⋅ 4 Baths ⋅ 100550322 MLS ⋅ ACTIVE Status ⋅ 2,841 SqFt. ⋅ 2022 Year Built
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
$2,950,000
7 Beds ⋅ 10 Baths ⋅ 100550100 MLS ⋅ ACTIVE Status ⋅ 10,405 SqFt. ⋅ 1919 Year Built
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
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 100547881 MLS ⋅ ACTIVE Status ⋅ 2,897 SqFt. ⋅ 1968 Year Built
Highly desirable single-level home located in the heart of Old Town Pinehurst. This beautifully updated brick residence offers the perfect blend of charm, craftsmanship, and modern convenience. Featuring 3 bedrooms and 3 full baths, the home showcases white pine hardwood floors throughout, a 2-car attached garage, plus a 1-car detached garage. The chef's kitchen is a standout with Monogram stainless steel appliances, a gas range with hood vent, nicely appointed granite countertops, and a high-end stainless sink handcrafted by American Indians--a truly unique detail echoed in one of the bathroom sinks as well. Two tankless hot water heaters add efficiency and comfort. The living room is warm and inviting with a stone fireplace with gas logs, built-in shelving, and a belvedere that floods the space with natural light. The spacious primary suite features a large walk-in closet with custom built-ins, slipper tub, double vanities, and a large walk-in shower. Additional highlights include a private office, Easy Breeze screened porch usable year-round, and a billiard room complete with bar--ideal for entertaining. Step outside to a beautifully landscaped backyard featuring established blue berry bushes, a relaxing patio, firepit, and a private hot tub--perfect for unwinding after a long day or enjoying peaceful evenings under the stars. One of the largest maple trees in the area provides stunning seasonal color. A 3-bay dog kennel, fully powered by electricity and also ideal for use as a workshop, is backed up by the whole-house propane generator during power outages, providing added peace of mind. The owners thoughtfully took this home down to the studs, creating a more efficient layout and offering confidence with updated plumbing and electrical systems. Conveniently located near Pinehurst Village, Pinehurst Golf Club, and shopping, this exceptional home presents a rare opportunity in one of Pinehurst's most sought-after neighborhoods. Transferable Pinehurst CC Membership!

700 Linden Rd, Pinehurst
$2,495,000
5 Beds ⋅ 6 Baths ⋅ 100538542 MLS ⋅ ACTIVE Status ⋅ 5,972 SqFt. ⋅ 1917 Year Built
''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
Start Your Search

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.