Hillsborough Homes with Orange - Orange High High School

Welcome to Hillsborough, North Carolina, a charming town nestled in the heart of Orange County. Known for its rich history and vibrant community, Hillsborough offers a unique blend of small-town charm and modern amenities. With its picturesque landscapes, historic architecture, and welcoming atmosphere, it’s no wonder that families and individuals alike are drawn to this delightful area.

Hillsborough is steeped in history, evident in its beautifully preserved buildings and quaint downtown area. Stroll through the streets lined with local boutiques, art galleries, and inviting cafes, where you can savor the flavors of the region. The town is also surrounded by lush parks and scenic trails, perfect for outdoor enthusiasts looking to explore the natural beauty of North Carolina.

For families considering a move to Hillsborough, the area is served by the highly regarded Orange High School. With a commitment to academic excellence and a wide range of extracurricular activities, Orange High provides students with the tools they need to succeed. The school’s strong community ties and dedicated staff create an environment where students can thrive.

When it comes to housing, Hillsborough offers a diverse selection of homes that cater to various lifestyles and budgets. Whether you're seeking a historic home with character or a modern residence with all the latest amenities, you’ll find it here. The tight-knit community, combined with excellent schools and a wealth of recreational opportunities, makes Hillsborough an ideal place to call home. Come explore all that this enchanting town has to offer!

Newest Hillsborough Homes with Orange - Orange High High School

$870,000

4 Beds ⋅ 4 Baths ⋅ 10183195 MLS ⋅ ACTIVE Status

This rare Forest Ridge home is officially available! It is located in a highly sought-after Hillsborough neighborhood famous for its vibrant, active lifestyle. The community features a spectacular pool, a playground, a sports field, and an incredible nature trail system. This trail connects to the Eno River and the historic Occoneechee Speedway Trail. What's more, Orange County Sportsplex is right across the street from the neighborhood, where you can enjoy basketball courts, ice skating, fitness classes, etc. The home features a fully paid-off solar system for immediate, massive utility savings. The flexible layout includes a private main-floor office, an expansive upstairs gym/loft, and a handy built-in drop zone. Guests will love the highly coveted main-level suite with its own full bathroom. Dual fireplaces anchor both the cozy living room and the premium screened-in porch for ultimate year-round comfort. The gorgeous eat-in kitchen features an oversized island, stunning quartz countertops, a tile backsplash, stainless appliances, and a huge walk-in pantry. Upstairs, the massive primary suite shines with an elegant tray ceiling, a dual vanity, a spa-like bath, and a huge L-shaped custom walk-in closet. The secondary bedrooms are perfectly designed with a functional Jack-and-Jill layout. Custom organization is integrated throughout the property. This includes custom closets, dedicated laundry cabinetry, and clever built-in under-stair storage. The property is complete with a beautifully epoxied garage floor. Outside, the private, fully fenced yard features a bonus invisible fence system alongside thriving fruit and flower trees. A spectacular line of Green Giant trees lines the yard for beautiful, year-round natural privacy. This ideal location puts endless daily conveniences right at your fingertips. A short drive takes you straight to excellent local shopping, outlets, popular restaurants, Home Depot, and everyday retail hotspots. Commuting is an absolute breeze with quick, unbeatable access to I-85, I-40, Highway 70, and Highway 86. You are close to Durham, Chapel Hill, and RTP. Don't miss out on this absolute dream home! Seller is real estate agent

204 Garden Heights Ln, 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

$580,000

3 Beds ⋅ 3 Baths ⋅ 10179657 MLS ⋅ ACTIVE Status

Detached 2-Car Garage with Finished Bonus Room & Full Bath! Welcome to this beautifully maintained 3-bedroom, 2.5-bath home tucked away on a quiet cul-de-sac in Hillsborough. Surrounded by mature trees, this home offers privacy, peaceful views, and plenty of space to relax. Recent updates include fresh interior paint, new flooring throughout much of the home, new carpet on the stairs and bedroom hallway, a newer LP gas stove, and a newer dishwasher. A newer roof and professionally maintained two-zone HVAC system provide added peace of mind. Enjoy your mornings on the welcoming front porch watching hummingbirds and bluebirds, or spend evenings relaxing on the back deck. The patio is perfect for grilling, entertaining, or adding a hot tub. This move-in-ready home offers the perfect combination of modern updates, flexible living space, and a peaceful setting just minutes from historic downtown Hillsborough.

419 Calvary Ct, 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

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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 .