Hillsborough

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About Hillsborough

The Town of Hillsborough offers a small-town vibe and plenty of natural beauty. Hillsborough’s downtown historic district is listed on the National Register of Historic Places, and it features homes, churches, schools, and other structures from the late 18th and 19th centuries. The town was established in 1754 where the Great Indian Trading Path crossed the Eno River. Hillsborough has easy access to both the Triangle and Triad regions via Interstates 85 & 40.

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TAMARINDSteeped in history and timeless romance, Tamarind is a rare offering in the heart of Hillsborough's cherished historic district. Built in 1903 and lovingly preserved over the course of 123 years, this remarkable estate has had only three owners, each serving as a thoughtful steward of its enduring legacy.Set just moments from the charm of downtown, Tamarind offers effortless walkability to local shops, cafés and restaurants, while remaining a private retreat tucked behind lush, mature landscaping. The main residence is rich with character and architectural detail, featuring soaring ceilings, eight fireplaces, and a seamless blend of historic craftsmanship and livable elegance.A sense of story carries throughout the home, most notably in the family room, where a chandelier from the North Carolina Governor's Mansion adds a layer of provenance and distinction. French doors in the primary suite open gracefully to the pool, creating a serene indoor-outdoor connection and a true sense of escape.The grounds are equally captivating, designed for both quiet enjoyment and effortless entertaining. A sparkling pool, expansive outdoor living areas, and a beautifully private yard create a setting that feels both intimate and inviting. Two separate guest cottages provide exceptional flexibility for hosting, creative pursuits, or extended stays.Tamarind is more than a home, it is a piece of Hillsborough's history, thoughtfully preserved and ready for its next chapter.Guest Cottage's are not included in the overall square footage.

$3,500,000 Active

318 N Churton Street Hillsborough, North Carolina

5 Beds 6 Baths 4,226 SqFt 0.68 Acres

Prime 38-Acre Opportunity! Exceptional location off I-40. Generous Frontage Road is perfect for a farm stand or farmers market. Currently in farming & forest use with rich soil, farm buildings, market structures, cabins, & shower house. Income potential via Airbnb, farm stand, farmers market, events. Development and soils study supports Barns, Houses and Farm Stand. A rare find with flexibility for homestead, retreat, or subdivided community.

$2,850,000 Active

4008 Old Nc 86 Hillsborough, North Carolina

1 Beds 1 Baths 500 SqFt 38 Acres

Beautiful pristine wooded 130 acre tract along Buckwater Creek between Hillsborough and Durham is full of possibilities. Develop into large lot subdivision, or build your dream estate, family compound, make this your private preserve, equestrian community, and more. Mature hardwoods, some pine forest, with rolling topography, a meandering stream, and remnants of an old homestead, this is a gorgeous property and truly a unique opportunity. Recent soil report shows great soils for septics. Pond(s) possible. Just off Pleasant Green Road near intersection with St. Mary's Rd. Across Buckwater Creek from state land and Eno River State Park. Nearby estate lot homes range from $800K to $1.5M+. Current zoning is Orange County AR with L-ENO-PW overlay. Access via public or private roads. Just 8 miles to Hillsborough and 10 miles to Duke & Durham.

$2,632,000 Active

1400 Happy Valley Farm Drive Hillsborough, North Carolina

5,658,008 SqFt 129.89 Acres

*NEWLY ADJUSTED PRICE + 1-year Home Warranty*Set on 10 acres in the Fox Hill Farm subdivision, 2601 Littleleaf Lane is a DREAM. This custom built features luxury amenities that makes it the perfect retreat. It features 5 FULL bedrooms and 5 FULL bathrooms of which 3 are ensuites, along with 2 half baths. As you enter from the covered porch through the grand foyer, you are greeted by 10' ceilings, elegant hardwood floors and arched entrance ways. The main level also showcases a formal dining area and formal living area, which provides more than adequate space for family gatherings and entertaining during holidays and special occasions. Follow the hallway to right and the stairs to the fully finished and furnished basement is to the left. This 1,540 square feet escape is to be seen to be believed. Featuring a 12-seat theater room with stadium style seating, projector and screen, full bath and wet bar, you will have enough room and space to entertain, watch the game, enjoy movie night with the family or have a cocktail to celebrate. The wellness retreat room is a gem! Featuring a full pedicure chair, salon-grade washing station and drying chair, bring your hair stylist and pedicurist to you! And you still have room for your massage table as well! This level features a half bath also. Back on the main-level, you'll find an expansive master suite that includes a double sided fireplace, dedicated sitting area with access to the outside deck, large walk-in closet, sunroom/den. The primary bath features, dual vanities, jacuzzi spa bath tub and a dual entry, walk in shower. All in the primary suite! 3 guest suite-style bedrooms on the main level are spacious and cozy. The kitchen was refreshed in 2023 with quartz countertops, new in-wall microwave/oven combo, gas cooktop, flooring and light fixtures. An abundance of natural lighting really helps the kitchen to shine. Off of the kitchen is the cozy breakfast nook for morning coffee. The family den ajoins to the sunroom. The double sided fireplace between the two rooms is a plus feature and makes enjoying family and friends more enjoyable. The second level of this luxury escape is equally as impressive. Featuring a 28'x22' bonus room, a 35'x25' gym and a 19'x13' flex space that could serve a bedroom, this is the perfect place to train, work, relax and recover. The second level also features two walk-in attic spaces: A HUGE 43'x69' walk-in unfinished attic area and 35'x14' utility area where the media, whole home audio and internet equipment is housed. Full shower bathroom on the second level.Outside of the home is a 66'x31' TREX deck. Installed in 2018, with new railing installed in 2024, this is the perfect location for a grill, deck furniture, and outdoor relaxation. The in ground pool measures at 18'x40'. New pool liner installed February 2026 refreshes this amenity for outdoor enjoyment and cooling off on those hot summer North Carolina days. New roof in 2018.Professionally landscaped yard and a concrete circular driveway. This home truly has it all--timeless style, modern updates, and peaceful acreage in sought-after Fox Hill Farm with miles of walking trails. Minutes to downtown Hillsborough and UNC Hillsborough Hospital, and 20 minutes to Duke and Downtown Durham. WELCOME HOME to 2601 Littleleaf Lane!

$2,375,000 Active

2601 Littleleaf Lane Hillsborough, North Carolina

5 Beds 7 Baths 7,905 SqFt 10.01 Acres

Stardust Farm: Where time slows, light shimmers, and the land remembers! There are places that feel discovered, and places that feel destined. Stardust Farm is the latter: A nearly 14-acre sanctuary where warm sunlight filters through ancient hardwoods, moonbeams sweep across open fields, and the air carries the quiet wisdom of a land loved for generations. At the heart of this enchanted property rests a historic farmhouse, accompanied by a cozy cabin and beautifully renovated one-bedroom home, creating a rare trio that forms a true heritage compound. Each dwelling has its own story, its own rhythm, yet all are united by the serenity of the landscape and the gentle hush of nature that surrounds them. This is land that has been tended with devotion; organically maintained for many years, the dedication shows its purity. The ground feels alive underfoot. Majestic trees create cathedral-like canopies. A tranquil koi pond glimmers like a hidden jewel. Everywhere you look, the property invites you to wander, explore, breathe, and simply be. Stardust Farm offers ancillary income from its current rental homes, but its true value lies in its potential: The ability to subdivide, expand, or create a one-of-a-kind retreat, gathering place, or legacy estate. From intimate weddings to wellness escapes, from compounds to visionary builds. The land welcomes every possibility. All of this magic exists within a gated, remarkably private setting with a subdividable lot and NO HOA, yet remains perfectly located: less than 3 miles from I-40 and minutes from downtown Hillsborough, Chapel Hill, and Carrboro. Stardust Farm is more than a property, it is a story waiting for its next author, a treasure seeking its next caretaker for this once-in-a-lifetime offering that glows with both sun and moon. There is simply nothing else like it! Make an appointment now and become entranced in a bit of its magic that you too can call home.

$2,200,000 Active

6202 Montgomery Estates Road Hillsborough, North Carolina

3 Beds 5 Baths 4,190 SqFt 13.64 Acres

Discover this stunning 51.3-acre parcel of land, perfectly situated just minutes from downtown Hillsborough. This beautiful property features lush, mature forests and an abundance of natural charm, offering the ideal blend of seclusion and convenience.Great for creating your dream home surrounded by nature—this land provides endless possibilities. With easy access to Hwy 70E, you can enjoy the tranquility of country living while remaining close to local amenities and attractions.Don't miss this opportunity to transform your vision into reality on this versatile and breathtaking land. Contact us today for more information.

$1,850,000 Active

51.3ac Nc-86 Hillsborough, North Carolina

2,234,628 SqFt 51.3 Acres

Experience unparalleled elegance in this architect-designed home by renowned builder Dennis Duffy, offering over 6,000 sq. ft. of living space, with an additional 3,000+ sq. ft. ready to finish in the basement and walk-up attic. Exceptional craftsmanship is evident throughout, from soaring ceilings and crown molding to the expansive floor-to-ceiling windows that fill the home with natural light and frame the stunning surrounding views.The gourmet kitchen is a chef's dream, featuring high-end Dacor appliances including a 6-burner stove, double oven, Sub-Zero fridge, granite countertops, and a detailed backsplash. The eat-in kitchen, framed by a bay window, is bathed in natural light. Floor-to-ceiling windows in the living room highlight the views and a cozy fireplace, opening to a spacious screened all-seasons room with another fireplace, stone accent walls, and stone flooring--perfect for year-round entertaining.The luxurious primary suite is a private retreat, with its own fireplace, expansive bathroom featuring a claw-foot tub, oversized walk-in shower, double vanities, and a dedicated beauty vanity with seating. Remote-controlled skylights in both master closets add a unique touch of convenience. Additional bedrooms are generously sized, and the main floor includes a guest bedroom and office.Thoughtful features extend throughout the home, including a two-story entryway with chandelier, two internal flights of stairs, external stairs to the upstairs, and a fenced backyard. The main floor laundry room includes a sink, extra storage, and almost-new washer and dryer. Comfort is ensured with three-zone AC, and peace of mind with a whole-house automatic generator. Connectivity is ready for modern living with a Starlink satellite dish and over-the-air TV antenna. A 2+1 car garage and outdoor patio complete this sophisticated and functional home, all set against serene 10+ acre views.

$1,850,000 Active

1101 Walnut Hill Hillsborough, North Carolina

5 Beds 6 Baths 6,131 SqFt 10.69 Acres

17.5-Acre Country Estate with Greenhouses, BarnIf you've been searching for a property that truly checks all the boxes, this one delivers--and then some.A standout feature is the two large, professional-grade greenhouses, complete with a dedicated backup generator--perfect for year-round growing, plant production, or serious gardening. The land is already thriving with established fruit trees and flowering plants, creating a turnkey homestead or small farm. Multiple approved perk sites add even more value, offering flexibility for future building or potential subdivision.The 4-bedroom, 3.5-bath home includes a versatile bonus room ideal for a guest suite, office, hobby space, or laundry. Inside, you'll find custom cabinetry, artisan sinks and lighting, and a newly coated garage floor--blending character with thoughtful updates.Set on 17.5 acres with extensive road frontage, the property also features a well-maintained five-stall barn with wash area, tack room with hot and cold water, fenced pasture, overhangs, and an attached workshop with hayloft--checking the box for equestrian or farm use.Inside the home, premium features continue with a Wolf gas range, Pella windows, passive solar design, wood-burning stove, tankless water heater, reverse osmosis filtration, and intercom system.A walk-out basement with plumbing already in place offers even more potential--whether for additional living space, workshop use, or storage.Greenhouses - Barn - Acreage - Privacy - Flexibility - Upgrades - Future PotentialIt's rare to find a property that brings it all together like this.

$1,700,000 Active

4811 New Sharon Church Road Hillsborough, North Carolina

4 Beds 4 Baths 4,455 SqFt 17.5 Acres

Sales Event 2/14!! 10-4pm; Welcome to Forrest Creek Estates, an exclusive 10-lot luxury enclave just minutes from historic downtown Hillsborough. Lot 1 offers over 2 acres of privacy in a serene, tree-lined setting surrounded by 15+ acres of preserved open space with scenic walking trails and a creek.Homes in Forrest Creek are custom-built by Hoeken Design Build, starting around $1.25 million, with architectural styles ranging from Modern Farmhouse to European-inspired designs. This is your opportunity to create a one-of-a-kind retreat where elegance meets natureâ€''convenient to Chapel Hill, Durham, Raleigh, and the Triangle's top universities and hospitals.

$1,635,000 Active

3516 Nc-57 Lot 2 Hillsborough, North Carolina

5 Beds 5 Baths 4,446 SqFt 2.68 Acres

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