Old Town Homes with False Waterfront

Old Town Homes with False Waterfront

Welcome to Old Town, a charming subdivision nestled in the heart of Pinehurst, North Carolina. Known for its picturesque landscapes and friendly community, Old Town offers a unique blend of Southern charm and modern living. This delightful neighborhood is perfect for families, retirees, and anyone seeking a serene lifestyle in one of the most desirable areas of Moore County.

One of the standout features of Old Town is its enchanting homes that boast false waterfront views. Imagine waking up each morning to the gentle sounds of nature and the tranquil ambiance of water, all from the comfort of your own backyard. These thoughtfully designed residences provide the illusion of waterfront living without the premium price tag, allowing residents to enjoy the beauty of nature right at their doorstep.

Old Town is not just about beautiful homes; it's also about community. The subdivision is conveniently located near Pinehurst’s vibrant downtown, where you’ll find an array of boutique shops, delightful cafes, and exceptional dining options. Outdoor enthusiasts will appreciate the proximity to golf courses, parks, and walking trails, making it easy to embrace an active lifestyle.

Whether you're looking to settle down or seeking a vacation retreat, Old Town in Pinehurst, NC, offers a perfect blend of comfort, community, and charm. Come explore the possibilities and discover why so many are proud to call this enchanting subdivision home. Your dream home awaits in Old Town!

Newest Old Town Homes with False Waterfront

$1,530,000
4 Beds ⋅ 4 Baths ⋅ 100603091 MLS
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

Listing courtesy of Lin Hutaff's Pinehurst Realty Group. Contact:

$1,150,000
3 Beds ⋅ 4 Baths ⋅ 100602456 MLS
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

Listing courtesy of Keller Williams Pinehurst. Contact:

$3,500,000
100599571 MLS
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

Listing courtesy of Carolina Summit Group, LLC. Contact:

$1,549,000
4 Beds ⋅ 3 Baths ⋅ 100580260 MLS
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

Listing courtesy of Coldwell Banker Advantage-Southern Pines. Contact:

$768,000
4 Beds ⋅ 3 Baths ⋅ 100573731 MLS
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

Listing courtesy of Premier Real Estate of the Sandhills LLC. Contact:

$2,295,000
4 Beds ⋅ 5 Baths ⋅ 100571799 MLS
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

Listing courtesy of Lin Hutaff's Pinehurst Realty Group. Contact:

$1,845,000
4 Beds ⋅ 4 Baths ⋅ 100571346 MLS
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

Listing courtesy of Taproot Realty Group LLC. Contact:

$1,100,000
3 Beds ⋅ 3 Baths ⋅ 100566358 MLS
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

Listing courtesy of Better Homes and GardensReal Estate Lifestyle Property Partners/SP. Contact:

$2,245,000
4 Beds ⋅ 6 Baths ⋅ 100558617 MLS
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

Listing courtesy of Lin Hutaff's Pinehurst Realty Group. Contact:

$1,500
100554336 MLS
Executive office space available in the Harvard Building located in the Village of Pinehurst.

95 Market Sq, Pinehurst

Listing courtesy of Taproot Realty Group LLC. Contact:

$1,275,000
4 Beds ⋅ 4 Baths ⋅ 100550322 MLS
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

Listing courtesy of Lin Hutaff's Pinehurst Realty Group. Contact:

$2,795,000
7 Beds ⋅ 10 Baths ⋅ 100550100 MLS
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

Listing courtesy of Pines Sotheby's International Realty. Contact:

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