Hillsborough Homes with Orange - Orange Middle Middle School

Hillsborough Homes with Orange - Orange Middle Middle School

Welcome to Hillsborough, North Carolina – a charming town steeped in history and surrounded by the breathtaking beauty of the Piedmont region. Nestled in Orange County, Hillsborough offers a unique blend of small-town charm and modern conveniences, making it an ideal place to call home. With its picturesque streets, vibrant community, and rich cultural heritage, Hillsborough is not just a place to live; it's a place to thrive.

The town is known for its historic architecture, with buildings dating back to the 18th century that tell the story of its past. Residents enjoy a variety of outdoor activities, thanks to the nearby Eno River State Park and the scenic trails that wind through the area. Whether you’re exploring the local farmers' market, indulging in the culinary delights of its quaint restaurants, or attending one of the many community events, there’s always something happening in Hillsborough.

Families will appreciate the proximity to Orange Middle School, which is highly regarded for its commitment to academic excellence and nurturing environment. Homes in this area are not only situated in a family-friendly neighborhood but also offer a range of styles and sizes to suit diverse preferences and budgets. From charming historic homes to modern developments, there’s something for everyone.

With its welcoming community, excellent schools, and rich history, Hillsborough stands out as a wonderful place to settle down. Explore the real estate options available and discover why so many choose to call this delightful town home!

Newest Hillsborough Homes with Orange - Orange Middle Middle School

$995,000
3 Beds ⋅ 3 Baths ⋅ 10184035 MLS ⋅ ACTIVE Status
This exquisitely crafted custom home, built by renowned builder Christopher Rand Construction and situated on 1.78 glorious acres in highly sought-after Fox Hill Farm, is truly something rare and special. From the moment you arrive by way of the gracious circular drive, the home makes an unforgettable impression. A welcoming front porch with beautiful stone accents invites you into a light-filled entry, where your eye is immediately drawn through the home to the serene, private backyard—made even more extraordinary by an adjoining four acres of land that will never be developed. Inside, the thoughtful layout and wonderful sense of space shine. The main-level primary suite is a peaceful retreat, featuring a tray ceiling, custom California Closets, direct access to the sweeping back porch, and a show-stopping bath with custom built-ins. The great room is, quite simply, great—with a soaring vaulted ceiling, a gas fireplace with flanking mirrored built-ins creating a space that feels both lux and cozy simultaneously. The open-concept kitchen features high-end appliances and is beautifully designed for gathering and entertaining. Just beyond, the vaulted, light-filled keeping room offers the perfect spot for game night, morning coffee, or curling up with a good book. Two additional bedrooms are connected by a Jack-and-Jill bath. One features a custom Murphy bed with built-ins, while the other offers a custom built-in desk and abundant storage, making both rooms as functional as they are beautiful. The home's extensive features and upgrades are almost too numerous to list, but highlights include a Generac whole-house generator, a fully insulated and conditioned three-car garage, site-finished hardwood floors, and exceptional storage throughout. Every detail has been thoughtfully considered. Every space feels gracious, comfortable, and beautifully connected to its surroundings. This is more than a home: it is an exceptionally crafted rare offering in one of Hillsborough's most desirable neighborhoods.

340 Fox Hill Farm Dr, Hillsborough
$499,000
3 Beds ⋅ 2 Baths ⋅ 10182820 MLS ⋅ ACTIVE Status
Welcome to this charming and historic home located at 627 Cedar Grove Rd in Hillsborough, NC. Built in 1931, this single-family residence offers a unique blend of vintage charm and beautiful modern updates. You will feel right at home in this quaint walkable historic town! The home is perfect for those that appreciate the character of original hardwood floors and baseboards, big picture windows that let in lots of light, but the modern luxuries of open concept floor plan, kitchen island, quartz counter tops, stainless appliances, double vanity in master bath and beautifully updated bathrooms. The views are perfect to watch the birds and the deer come by and enjoy the colorful seasons that North Carolina offers. Upon arrival, you will be greeted by a spacious lot size of 13,068 square feet, providing ample space for outdoor activities and entertaining. Enjoy the new outdoor kitchen and Pergola or take a seat at the fire pit with your guests to enjoy many gorgeous relaxing North Carolina evenings! Overall, 627 Cedar Grove Rd is a delightful property that combines the charm of yesteryear with the convenience of modern amenities. Hillsborough is a picture perfect town and you will enjoy walking to the shops and restaurants as well as the parks and festivities that are planned year round. You can walk to River Park or Gold Park, and you are in a perfect central location close to Duke, UNC, and Chapel Hill.

627 Cedar Grove Rd, Hillsborough
$450,000
3 Beds ⋅ 3 Baths ⋅ 10182204 MLS ⋅ ACTIVE Status
Move-in ready, this inviting home offers an open floor plan designed for comfortable everyday living and effortless entertaining. The spacious living area flows seamlessly into the kitchen and dining spaces, creating a bright and welcoming atmosphere. The kitchen provides plenty of cabinet and counter space, making meal preparation and gatherings a breeze. The second level primary suite offers a relaxing retreat, while the additional bedrooms provide flexibility for guests, a home office, hobbies, or other needs. Thoughtful finishes and a functional layout make this home easy to enjoy from the moment you arrive. Step outside to a fully fenced backyard with patio, offering space for outdoor dining, gardening, recreation, or simply relaxing in your own private setting. Whether hosting, enjoying quiet evenings outdoors, or spending time with pets, this backyard is ready to fit a variety of lifestyles. Conveniently located in Hillsborough, you'll enjoy easy access to shopping, dining, parks, schools, and major commuting routes while still appreciating the charm and character of the surrounding area. If you've been searching for a home that combines move-in ready convenience, an open layout, and inviting indoor and outdoor living spaces, this is one you won't want to miss. Schedule your showing today and discover all this property has to offer.

521 Terrell Rd, Hillsborough
$2,225,000
4 Beds ⋅ 4 Baths ⋅ 10180084 MLS ⋅ ACTIVE Status
Rare Opportunity to Own a Horse Farm in Hillsborough! Set on over 17 picturesque acres, this exceptional property offers endless possibilities as a private equestrian estate, working farm, homestead, or event venue. The thoughtfully designed home combines quality craftsmanship with comfortable living. A grand foyer opens to a spacious living room anchored by an impressive stone fireplace and expansive windows overlooking the beautiful grounds. The kitchen features granite countertops, a commercial 36" gas range, stainless steel appliances, and abundant cabinetry. A light-filled sunroom with skylights spans the rear of the home, while the main-level primary suite offers dual closets, dual vanities, and a custom walk-in shower. A spacious laundry room with granite counters and ample storage adds convenience. Upstairs are 3 generously sized bedrooms, a bonus room with hidden attic storage, and two full baths with separate vanity areas. Additional features include a whole-house intercom, central vacuum, water filtration system, and a 2,000+ sq. ft. walk-out basement with plumbing already in place, offering incredible potential for additional living space, guest quarters, or an event area. Step outside to enjoy the expansive rear deck, fire pit, and regulation horseshoe pits. The professionally landscaped gardens are truly spectacular, featuring winding hardscape paths through an extraordinary collection of labeled ornamental plants, flowering shrubs, and mature fruit-bearing trees including figs, kiwis, blueberries, pears, peaches, plums, grapes, pomegranates, and persimmons. For gardeners, entrepreneurs, or homesteaders, the property includes two large commercial-quality greenhouses, one with its own backup generator, creating exceptional year-round growing and income-producing opportunities. Multiple approved perk sites offer additional flexibility for future building or subdivision. Equestrians will appreciate the five-stall barn with two mare stalls, wash area, tack room with hot and cold water, attached workshop, hayloft, and two fenced pastures totaling approximately seven acres. The property also features two scenic ponds, one with a gazebo and mature koi, the other stocked with fish, approximately 2,300 feet of new trails for riding, hiking, or ATVs. This is more than a home—it's a rare lifestyle property offering beauty, functionality, income potential, and room to grow, all just minutes from Hillsborough. Come experience everything this remarkable property has to offer! A full Features sheet is available in MLS documents.

4811 New Sharon Church Rd, Hillsborough
$550,000
3 Beds ⋅ 2 Baths ⋅ 10179946 MLS ⋅ ACTIVE Status
Let me tell you 'bout the birds and the bees, and the flowers and the trees, and the moon up above, and a place you'll love! Nestled in between Churton Grove and Fox Hill Farms, this home offers the best of both worlds - super convenient to downtown Hillsborough, but in an incredibly private and peaceful setting. This retreat is almost your own private park with views from the back deck of Stroud's Creek, wildlife visitors, and beautiful plants and flowering trees all around. Enjoy a glass of sweet tea in the gazebo, or stargaze around the firepit, or cozy up on the front porch for the evening firefly show across the way. You can even bring your chickens. And don't forget to invite your human friends too! Plenty of space for entertaining, and the flow of the house is nearly perfect for guests. The kitchen and dining room open to the living room so everyone has a place to sit, and you can send the rowdy crowd on downstairs to the family room! Don't forget hot chocolate by the woodstove on those chilly fall nights. Large bedrooms make all feel like they have plenty of space, and storage options are great - walk-up storage above the detached two-car garage is so helpful! Big ticket maintenance items taken care of in the last few years include roof (2025), HVAC (2024), well and pump (2023), and water heater (2023). Settle in for a place you can truly call home.

1112 Meadowbrook Trl, Hillsborough
$495,000
3 Beds ⋅ 2 Baths ⋅ 10179611 MLS ⋅ ACTIVE Status
Nestled along the tranquil banks of the Eno River, this home is a completely reimagined waterfront retreat that offers a rare blend of secluded natural beauty and modern sophistication. Step out into your backyard to take in the soothing sights and sounds of the river, or look across to the iconic Mountains-to-Sea Trail running along the opposite bank. While you will feel miles away from the hustle and bustle in your private oasis, you are incredibly well-connected, sitting just a five-minute drive from the award-winning restaurants and boutique shopping of historic downtown Hillsborough, with grocery stores and major commuter routes just minutes further. No detail was spared in the extensive, top-to-bottom transformation of this home. The full-home premium remodel includes a brand-new HVAC system, a new water heater, fresh ceilings, energy-efficient windows that flood the rooms with natural light, and beautiful oak flooring running throughout. The true showpiece of the home is the stunning chef's kitchen, boasting completely new cabinetry, gorgeous countertops, an expansive layout, and ultra-high-end appliances highlighted by a professional-grade Wolf induction cooktop. The thoughtfully designed floor plan spans 1,737 square feet of finished living area, maximizing both private quarters and grand entertaining spaces. The main and upper levels feature a welcoming living and dining area, a convenient full bathroom, and three bedrooms, including a spacious primary retreat. Meanwhile, the lower level adds incredible versatility with a massive 24.5' x 22.8' recreation room—perfect for a home theater or secondary lounge—alongside a second full bathroom, a dedicated laundry room, and effortless walkout access to the rear patio. Outdoor living is just as impressive, featuring a welcoming back patio that is ideal for hosting unforgettable riverside barbecues. Whether you are hitting the nearby trails at River Park, exploring the vibrant local community, or simply relaxing by the water, this turnkey property delivers an unmatched North Carolina lifestyle. Don't miss this incredibly rare opportunity to own a fully remodeled waterfront masterpiece.

1713 Riverside Dr, Hillsborough
$780,000
5 Beds ⋅ 4 Baths ⋅ 10179417 MLS ⋅ ACTIVE Status
Welcome to 605 N. Scotswood, where timeless design and thoughtful spaces come together to create a home that's as functional as it is inviting. The spacious kitchen, main-level primary suite, flexible living areas, and screened porch overlooking the wooded backyard make everyday living feel both comfortable and effortless. Located in the sought-after Churton Grove community, you'll enjoy neighborhood amenities, mature landscaping, neighborhood trails, and the convenience of being just minutes from downtown Hillsborough, Durham, and Chapel Hill. This is the kind of home that's made for gathering with loved ones, celebrating life's milestones, and creating memories for years to come. Come take a look - you just might find yourself feeling at home the moment you walk through the front door.

605 N Scotswood Blvd, Hillsborough
$284,000
2 Beds ⋅ 2 Baths ⋅ 10179411 MLS ⋅ ACTIVE Status
**Move In Ready & $5,000 SELLER-PAID CLOSING COSTS!** Like-new appearance, spacious 0.36-acre lot, NO HOA, and just minutes from Historic Downtown Hillsborough, this home delivers exceptional value and flexibility. Stop renting and start building equity in this move-in-ready home priced under $300K! A complete 2021 remodel means the major systems and features—including the roof, HVAC, water heater, energy-efficient windows, gutters, light fixtures, and stacked washer/dryer—are only about 5 years old. The stylish, chef-inspired kitchen features shaker cabinetry, granite countertops, a custom tile backsplash, and stainless steel appliances. Step outside and enjoy the space! The generous lot gives you room to create the backyard you've always wanted, with no HOA restrictions, so much potential. Build a workshop, create a garden, add outdoor entertaining space, or simply enjoy having room to spread out. The expansive covered front porch adds classic Southern charm, the perfect spot for rocking chairs, morning coffee, or relaxing evenings. A substantial covered carport with attached storage and an additional storage shed, bring your life with you. Location matters, you're just minutes from the shops, restaurants, breweries, and events of Historic Downtown Hillsborough, while also enjoying convenient access to Durham, Chapel Hill, Duke University, UNC, Raleigh, and Greensboro. Fairview Park is just around the corner, offering playgrounds, ball fields, and tennis/pickleball courts for easy recreation close to home. Like-new condition. Spacious outdoor living. No HOA. Fantastic location. **$5,000 in seller-paid closing costs** Whether you're ready to stop renting or looking for an affordable home, this Hillsborough home is ready to welcome you! Recently refreshed with paint and a touch up professional cleaning to highlight it's recent 2021 remodel

539 Riddle Ave, Hillsborough
$1,055,000
4 Beds ⋅ 4 Baths ⋅ 10179341 MLS ⋅ ACTIVE Status
Private Custom brick home in a beautiful Grand Oak Estate neighborhood. A short drive to downtown Hillsborough and Duke. Spacious wrap-around rocking chair front porch with rear screened porch. Home features beautiful reclaimed hardwood floors from an old whiskey distillery throughout the main floor, the railings to go upstairs were locally designed and milled. Tile floor in baths and utility room, granite countertop with custom cherry cabinets in kitchen. Design ideas based on a Carolina "T" Farmhouse using a brick finish. Main living area has a wood burning fireplace and the piano room utilizes a gas burning fireplace. Heated and cooled walk out basement (not included in the square footage) that also features a wood burning stove. Located on over 8 acres. Backyard receives great light for a garden. Surrounded by beautiful hardwood trees perfect for cutting shaded walking trails. Grand Oak Estates has a playground common area with a tennis court. Eno River Farms berry picking in an exciting adventure just down the road.

417 Grand Oak Dr, Hillsborough
$430,000
3 Beds ⋅ 3 Baths ⋅ 10178877 MLS ⋅ ACTIVE Status
A quaint countryside home encircled by shade trees and situated on over an acre of land, this house offers a quiet and peaceful lifestyle only minutes to downtown Hillsborough. This 3 bedroom 2.5 half bath home has a large living room with a fireplace, and a flex room with hardwood floors. There is a spacious kitchen with plenty of cabinets and counter space, and room for a breakfast or dining table. Enjoy your morning coffee on the back deck overlooking the wonderful backyard. The generously sized primary suite is a peaceful retreat with a walk-in closet and a primary bathroom with double sinks, a separate shower and a garden tub. Two additional bedrooms provide flexibility for family, guests, or a home office. Outdoor features include a storage closet attached to the house, a roomy deck, a firepit, and a spacious backyard teeming with wildlife. This home is an opportunity perfect for those who want a cozy country lifestyle close to Hillsborough.

3012 Prophet Dr, Hillsborough
$275,000
2 Beds ⋅ 2 Baths ⋅ 10178828 MLS ⋅ ACTIVE Status
Major price improvement on this AMAZING location! Just minutes from the heart of downtown Hillsborough, you'll enjoy easy access to locally owned restaurants, a popular brewery, charming shops, and a specialty grocery store. This solidly built ranch home has been lovingly owned by the same family since 1960 and is ready for its next chapter. Situated on a flat 0.32-acre lot, the property offers plenty of outdoor space for gardening, entertaining, or simply enjoying the yard. Priced with room for cosmetic updates, it's a fantastic opportunity to create the home you've been dreaming of while preserving the quality craftsmanship that's hard to find today. Inside, you'll find 2 bedrooms, 2 full baths, and two versatile flex spaces that are perfect for a home office, hobby room, playroom, or additional living area. The spacious family room features a cozy gas log fireplace, while the kitchen offers beautiful solid wood cabinetry, abundant storage, and a peninsula that provides plenty of workspace for cooking and gathering. Outside, the large wired storage building is ideal for a workshop, hobbies, or extra storage. Whether you're looking for your first home or a place to personalize, this home offers endless potential in one of the area's most desirable locations.

422 Orange Heights Loop Rd, Hillsborough
$260,000
3 Beds ⋅ 2 Baths ⋅ 10178660 MLS ⋅ ACTIVE Status
Your chance to own this Hillsborough gem! Charming & Spacious Living Just Minutes from Downtown Hillsborough! This home offers a fantastic blend of space, comfort, and convenience. Nestled on a generous .34-acre lot with no HOA, this property provides the indoor and outdoor space you've been looking for. Inside, you'll find a bright, fully livable layout highlighted by brand-new flooring and fresh interior paint throughout. The functional, classic kitchen flows into a cozy family room with a fireplace and includes a new refrigerator (2025), perfect for moving right in now and updating to your personal taste over time! Outdoor living is easy with two large decks on the front and back of the home that are ready for grilling, relaxing, or entertaining. Major systems and updates have already been prioritized for the next owner: Brand-new water heater (2026) Brand-new interior flooring & fresh paint throughout New sliding glass door (2026) Newer bathroom updates (sink cabinets & toilets) Durable metal roof Public water and sewer connections Please note: To offer this incredible value, the property is being sold strictly in its current condition, and the seller will not be making any additional repairs. Located within walking distance to Fairview Park and the Dorothy N. Johnson Community Center, you are just a 5-minute drive from Downtown Hillsborough and only 15 minutes from Downtown Durham and Duke Hospital. Enjoy easy highway access and low-maintenance living from day one. Schedule your showing today!

548 Riddle Ave, Hillsborough
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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 .