View All Pinehurst NC Homes with Vacation Rental Listings

$425,000
2 Beds 2 Baths 100584975 MLS Lakeview Condos BLDG.
Short Term Rentals Allowed- STR Certificate attached to this property. Enjoy beautiful views of Lake Pinehurst from this fully furnished, 2nd floor, 2 bedroom, 2 bath waterfront condominium. Whether you're searching for a full time residence, a vacation getaway, or an exceptional investment opportunity, this turnkey property offers the perfect combination of comfort, location, and income potential. Relax on your private balcony while taking in views of Lake Pinehurst, or spend the day enjoying the community swimming pool just steps away. Inside, the spacious floor plan is furnished and move in ready, allowing you to immediately begin enjoying the Pinehurst lifestyle. The condo conveys fully furnished and includes a Village of Pinehurst Short Term Rental Certificate that conveys with the property, making it ready for immediate vacation rental use. With a proven history of strong VRBO and Airbnb rental income, this is a rare opportunity to own an income producing lakefront property in one of Pinehurst's most desirable communities. Located just minutes from the charming Village of Pinehurst, world renowned golf, dining, shopping, and area attractions, this exceptional waterfront condo offers resort style living with outstanding investment potential. Investor opportunity! The seller is also offering Unit 114, providing the rare chance to acquire two furnished lakefront condos with transferable Village of Pinehurst Short-Term Rental Certificates and established vacation rental income. Purchase one or both to expand your investment portfolio.

250 Sugar Gum Ln Unit # 237, Pinehurst

Courtesy of Living on The Bliss Realty

$465,000
2 Beds 2 Baths 100584967 MLS Lakeview Condos BLDG.
Short Term Rentals Allowed-STR Certificate attached to this property. Wake up to breathtaking views of Lake Pinehurst from this beautifully furnished, 1st floor, 2-bedroom, 2-bath waterfront condominium. Offering effortless one-level living, this turnkey property is perfectly suited as a primary residence, vacation retreat, or exceptional investment opportunity. Enjoy your morning coffee or evening cocktail while relaxing on the private balcony overlooking the sparkling waters of Lake Pinehurst. Residents also enjoy access to the community pool, making it easy to embrace the resort lifestyle. The condo conveys fully furnished and includes a Village of Pinehurst Short-Term Rental Certificate that conveys with the property, making it ready for immediate vacation rental use. With a proven history of strong VRBO and Airbnb rental income, this is a rare opportunity to own an income-producing lakefront property in one of Pinehurst's most desirable locations. Just minutes from the charming Village of Pinehurst, world-renowned golf, dining, shopping, and area attractions, this exceptional waterfront condo offers the perfect combination of lifestyle, location, and investment potential. Investor opportunity! The seller is also offering Unit 237, providing the rare chance to acquire two furnished lakefront condos with VOP Short Term Rental Certificates and established vacation rental income. Purchase one or both to expand your investment portfolio.

250 Sugar Gum Ln Unit # 114, Pinehurst

Courtesy of Living on The Bliss Realty

$2,950,000
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

Courtesy of Pines Sotheby's International Realty

$1,350,000
4 Beds 4 Baths 100534485 MLS
Old Town Pinehurst- Luxury Meets Location! Location truly matters and this home delivers! Nestled in the heart of Old Town Pinehurst, this beautifully updated 4 bedroom 3 1/5 bath home offers a Pinehurst Country Club membership & is just steps away to the charming Historic Village, renowned for its New England-style architecture, boutique shops, acclaimed restaurants, World-Class Golf, & the iconic Carolina Hotel & Spa. This unique & spacious residence now features 4 bedrooms and 3 full ensuite baths, each with bidets, walk-in closets, & high-end finishes—two with marble countertops, & a primary bath with space for a large tub. The lower level has been thoughtfully reconfigured to include a fourth bedroom, along with a mancave, workshop, storage area, and the original 2+-car garage. In total, the property offers 4 garage bays plus golf cart storage—ideal for vehicles & hobbies. The main level showcases 10-foot ceilings, natural white oak flooring, crown molding, & a stunning cook's kitchen featuring sleek European-style cabinets, new quartz countertops, a new Wolf Dual Fuel Range, new LG refrigerator, drawer microwave, & a large island with a new stainless undermount sink & Kohler faucet. The open layout flows seamlessly into the great room & formal/informal dining areas, centered around a cozy fireplace with a new modern gas insert. Additional upgrades include Andersen windows, a new Pella sliding door, professionally waterproofed basement, sealed & encapsulated crawlspace, central vacuum system, beverage/wine cooler, solar tubes, & a guest bath plumbed for a steam shower. The fully irrigated yard offers a private rear deck with privacy screen—perfect for relaxing or entertaining. With a flexible floor plan offering both private retreats & generous gathering spaces, this home is ideal as a full-time residence, vacation getaway, monthly rental, or long-term investment. A rare & exceptional opportunity in the heart of the Village of Pinehurst.

110 Mclean Rd, Pinehurst

Courtesy of Coldwell Banker Advantage-Southern Pines

Buyer Representative Old Glory Realty LLC

Start Your Search

IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS.  The MLS may, at its discretion, require use of other disclaimers as necessary to protect participants and/or the MLS from liability. 

Listings provided by LERA MLS

All information should be verified by the recipient and none is guaranteed as accurate by ARMLS. Copyright 2026 Arizona Regional Multiple Listing Service, Inc. All rights reserved.

Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .

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.

Pinehurst, NC · Curated MLS Search

Homes with Vacation Rental in Pinehurst, NC

An editorially curated view of every active homes with vacation rental listing in Pinehurst, NC. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings