Highland Real Estate

Welcome to Highland, Illinois – a charming city nestled in the heart of Madison County. Known for its picturesque landscapes and vibrant community spirit, Highland offers a perfect blend of small-town charm and modern conveniences. With a population of just over 9,000 residents, this welcoming city is an ideal place for families, retirees, and everyone in between.

Highland boasts a rich history that dates back to the 1800s, reflected in its beautifully preserved architecture and local landmarks. The city is famous for its annual events, such as the Highland Homecoming Festival, which brings the community together to celebrate with food, music, and fun activities for all ages. Nature enthusiasts will appreciate the abundance of parks and recreational opportunities, including the scenic trails at the Highland City Park and the picturesque views along the Kaskaskia River.

Education is a cornerstone of Highland, with highly-rated schools that prioritize student success and community involvement. The city also offers a variety of local shops, restaurants, and services, ensuring that residents have everything they need right at their fingertips.

For those commuting to nearby cities, Highland is conveniently located just 30 miles from St. Louis, making it an ideal spot for those who want to enjoy the tranquility of suburban living while being close to the excitement of urban life.

Whether you’re searching for your dream home or looking to invest in a thriving community, Highland, IL, is a hidden gem that promises a fulfilling lifestyle. Come explore all that this delightful city has to offer!

Newest Listings in Highland

$400,000

3 Beds ⋅ 2 Baths ⋅ 26072135 MLS ⋅ ACTIVE Status

: Beautifully updated, full-brick ranch on 2 acres in the highly desirable Highland School District! Enjoy the best of country living with modern updates, spacious rooms, and room for all your hobbies and outdoor activities. Offering 3 bedrooms, 2 bathrooms, a 3-car attached garage, and a pole barn, this property combines comfort, charm, and functionality in a setting you’ll love! The main level has been completely transformed with an open, brighter feel, fresh paint throughout, all-new luxury vinyl plank flooring, and updated lighting. The stunning new kitchen features custom cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, and an oversized custom center island with electricity, creating the perfect space for cooking, gathering, and entertaining. The spacious dining room features a beautiful brick fireplace, adding warmth and character to the home. All three bedrooms are generously sized, including a large primary suite with an updated private bathroom featuring a brand-new glass shower, new flooring, and updated bathroom fixtures. The main bathroom has also been refreshed with a new tub, tub surround, flooring, and bathroom fixtures. The unfinished basement offers additional potential and features a second brick fireplace, providing a great opportunity to create additional living or entertaining space.Outside, enjoy the peaceful setting with a covered concrete front porch and a spacious covered concrete patio just off the back doors, both perfect for relaxing and enjoying the country views. The property backs up to an open farm field, offering a beautiful backdrop and a sense of privacy. Additional highlights include ample parking, a pole barn with concrete flooring, and two cisterns on the property. The pole barn provides plenty of room for vehicles, equipment, hobbies, or storage.If you’ve been searching for an updated brick ranch with acreage, outbuildings, and a peaceful country setting while still enjoying the benefits of the highly desirable Highland School District, this property is one you won’t want to miss! Buyer/buyers agent to independently verify all info. Continguent on sellers closing on a new home.

13469 Buckeye Rd, Highland

$250,000

4 Beds ⋅ 3 Baths ⋅ 26071525 MLS ⋅ COMING SOON Status

Open House 11/21 at 11AM to 1PM - Welcome home to this beautifully remodeled 4-bedroom, 2.5-bath home offering modern updates, thoughtful functionality, and plenty of space to enjoy! The main level features a spacious primary suite and the convenience of main-floor laundry, making everyday living easy. Upstairs, you’ll find three additional bedrooms, a full bathroom, and a versatile loft area that provides the perfect space for a second living area, home office, or playroom. Completely remodeled from top to bottom, this home offers peace of mind with an extensive list of improvements, including new siding, a new back deck, updated bathrooms, new flooring throughout, a beautifully remodeled kitchen with new appliances, updated electrical and plumbing, and a new roof installed in November 2025. With its blend of modern finishes, functional layout, and major updates already completed, this home is move-in ready and waiting for its next owners to enjoy. Don’t miss the opportunity to make this beautifully updated home yours! Agent Owned

1215 14th St, Highland

$304,900

3 Beds ⋅ 3 Baths ⋅ 26071340 MLS ⋅ ACTIVE Status

Enjoy This 2002 Ranch Home With Walkout Basement & Daylight Windows In An Excellent Established Neighborhood With Lots Of Trees; FEATURING: 3 Bedroom & 3 Bath HOME With 2 Bonus Rooms Which Could Be Utilized As Additional Bedrooms; Living Room With A Gas Fireplace; Main Floor Master Bedroom & A Master Bath Designed With A Skylight; Huge 20x12 EAT-IN Kitchen With Large Pantry; MAIN FLOOR LAUNDRY; Fully Finished Basement With A Beautiful Wood Bar Area, Recreational Area With A Decorative Free-Standing Natural Gas Stove, Family Room With Daylight Windows, 2 Bonus Rooms With Closets, OFFICE, & A Full Lower Bath; 200 AMP Electric Service; Newer Water Softener; New Roof 2022; Hot Water Heater 2021; Natural Gas Powered GENERAC Emergency Generator; Large 16 x 10 SHED; Fenced Back Yard; Large Traditional Covered Front Porch; RV Parking Could Be Possible; LOCATED: Near Bike/Walking Trail, Park, & Schools; High Speed Internet Available; EXCELLENT LOCATION: 30 Minutes From SCOTT AFB & 35 Minutes From Downtown St Louis

2106 Hill Crest Dr, Highland

$420,000

4 Beds ⋅ 3 Baths ⋅ 26068913 MLS ⋅ ACTIVE UNDER CONTRACT Status

List and Sold Same Day. This home is move in ready. In the 10 plus years that these Sellers have owned it, they completely remodeled it. So many upgrades of quality work and maintenance upkeep. When you walk in what you first notice is all the beautiful woodwork throughout the home and the open floor plan. The six panel doors and trim work is exceptional, along with the engineered wood floors. The living room has a cathedral ceiling and a a bay window. The dining room sits in-between the living room and kitchen boosting a masonry gas fireplace. Off of the dining room, the sellers added on a 12x22 Screened-n-Porch to enjoy the birds and wildlife in the woods behind them. Primary bath recently had a new all tile walk-n-shower added with multiple sprayers. Kitchen has plenty of oak cabinets, pantry and solid surface Corian counter tops and tile backsplash. Laundry Room is off of the Garage and Kitchen for convenience with an additional closet and deep sink, Lower level is a walkout basement with plenty of windows. There is a 4th bedroom with egress and a full bathroom and a family room. A huge storage room and workshop with double doors leads to outside. Walkout double doors goes to a patio under the above screen-n-porch. Home sits on 2 acres with a 12x24 shed on skids, great for all the mowers and tools. Oversized 2 car garage is attached to the home with additional parking area. Besides all the interior updates that have been done to the home the roof was replaced Oct. 2025. Furnace and AC was replaced 2017. Pro Alarm for security system. This home is ready to be moved into.

2912 Wellen Rd, Highland

$479,900

4 Beds ⋅ 4 Baths ⋅ 26070330 MLS ⋅ COMING SOON Status

You don't want to miss this beautiful brick-and-stone home in a great location within Highland’s Prairie Trails subdivision! Offering 4 bedrooms, 3.5 bathrooms, and approximately 3,400 square feet of finished living space, including the finished basement. This home provides plenty of room to relax and entertain. The open floor plan connects the kitchen, dining area, and living room, where built-in surround sound enhances movie nights and gatherings. Granite countertops and tile flooring complement the kitchen and bathrooms. Main-floor laundry adds everyday convenience, while office space right off the living room provides a dedicated spot for work or study. The spacious primary suite features a large walk-in closet and a private bathroom with heated tile flooring, granite countertops, double sinks, a large jetted tub, and a tiled walk-in shower. The finished lower level offers a bar, bedroom, bathroom and a generous entertaining room. Outside, enjoy beautiful landscaping and a concrete patio with a built-in fireplace—an inviting setting for evenings outdoors. A three-car garage, 0.28-acre lot, and roof replaced in 2025 complete this appealing home!

375 Baneberry Dr, Highland

$249,900

3 Beds ⋅ 1 Baths ⋅ 26070299 MLS ⋅ COMING SOON Status

Move-in-ready home on a spectacular 1.61+/-acre lot in the highly desirable Triad School District! This charming property offers the perfect blend of spacious indoor living and extensive outdoor space, making it an ideal place to call home just in time for the holidays. The main level features a large living room complete with a cozy wood-burning fireplace—perfect for relaxing with family or entertaining friends. Home cooks will love the expansive eat-in kitchen, offering ample counter space and room for the whole family to gather, cook holiday meals, and bake cookies together. With 3 comfortable bedrooms and a well-appointed large bathroom, this home delivers an excellent footprint. Storage is a breeze thanks to the partial basement, perfect for keeping things organized. Outside, the park-like 1.61-acre lot gives you room to breathe, spread out, and fully embrace your favorite outdoor hobbies, gardening, or recreation. Don't miss this incredible opportunity to move right in and start making memories! Agent related to seller.

11867 State Route 143, Highland

$165,000

26067275 MLS ⋅ ACTIVE Status

Investment opportunity in the heart of Highland! This two-family property features a spacious 3-bedroom unit ($1350 rent) and a separate 1-bedroom unit (rented for $800), offering flexibility for investors or owner-occupants looking to offset their mortgage with rental income. The property currently generates $25,800 in annual gross income. The water/sewer is included in rent for tenants as there is one water meter. The rest of utilities are covered by each tenant. Both units will be sold with its appliances, making the transition easy for the new owner and tenants. The basement provides two sets of washers and dryers, with a dedicated set available for each unit. Whether you’re adding to your rental portfolio or exploring multi-family ownership, this Highland property is well worth a look! Preapproval or proof of funds required to show as to not bother current tenants.

1020 9th St, Highland

$350,000

26070704 MLS ⋅ ACTIVE Status

Price listed is Starting Bid Only. The property will be auctioned off at @7 pm at the St Rose Development Club on 11/25/26. Property will be selling in one tract. Tract #4 +/- 35.5 acres of farmland. Property will sell under auction terms and be sold AS- IS, WHERE-IS. Seller will not make no repairs as a result of any building, occupancy, or environmental inspections. Buyer will be required to sign an Auction Purchase & Sale Agreement and put 5% down if final bid is accepted by Sellers.

802 Zilles Rd, Highland

$310,000

2 Beds ⋅ 2 Baths ⋅ 26070094 MLS ⋅ ACTIVE Status

WELCOME TO EASY LIVING! A beautifully loved villa on a quiet cul de sac with a pretty open backyard. The large open living & dining areas with cathedral ceiling give a freeing feeling. The full hall bath has tub/shower and the main bath has a walk-in/roll-in shower. The bedrooms have darkening shades installed. You'll really appreciate the separate office room or make it a large area for storing favorite keepsakes. The fully equipped kitchen has oak cabinets and tile backsplash. The handy laundry has a sink and wall cabinet. All rooms sport pristine updated flooring. The garage is over-size with ample storage space and easy-access ramp into home. Updates include disposal 6/2025, flooring 5/2023, shower 12/2024, furnace and ac new 10/2023, painting interior 2023, energy efficient furnace with hudmidifier. See the HOA attachment for all the amenities that maintain this villa - lots of peace of mind!

56 Malan Ct, Highland

$232,000

2 Beds ⋅ 2 Baths ⋅ 26068717 MLS ⋅ ACTIVE UNDER CONTRACT Status

List/Sold Same Day! Welcome home to this charming, newly renovated multi-level residence nestled on a picturesque, tree-lined cul-de-sac in Highland with close proximity to Schools, Dining, Shopping, Hospital and the town square! This BEAUTY features 2 bedrooms and 2 nicely-renovated bathrooms! The beautifully updated living space offers comfort, style and versatility! Step inside to discover all new flooring throughout and a completely renovated interior! The updated Kitchen shines with Granite Countertops, tiled backsplash, stainless appliances and pantry! The Spacious living room overlooks the peaceful tree-lined cul-de-sac creating a welcoming space to unwind or entertain! Upper level features 2 bedrooms, and a beautifully renovated full bathroom! Downstairs you'll find a versatile "flex/bonus" room and a Gorgeous 3/4 (updated) bathroom. Main Floor is also highlighted by the Spacious Laundry Room for "Everyday" convenience. Additional highlights include new roof, new windows (except for LR & DR), oversized 1 car garage, Charming Back patio with Bistro Lighting!

1302 Ash St, Highland

$205,000

26068695 MLS ⋅ ACTIVE Status

Looking to to add to your rental portfolio? Looking to get started out with your first investment property? Look no further that this Quadriplex in the highly desired town of Highland! All 4 units currently leased out and tenants would like to stay! One unit recently renovated! Back deck and stairs completely redone! Off-street parking available with a 4-car carport in the rear! Washer/Dryer in unfinished basement! Location, Location, Location! This one is walking distance to many popular business in the ever so popular Highland Town Square! Just minutes to 143, Highway 40, and Interstate 70 for quick and easy commutes! Contact your favorite agent to set up a showing today!

1413 9th St, Highland

$279,900

3 Beds ⋅ 3 Baths ⋅ 26064980 MLS ⋅ ACTIVE Status

Classic Charm, Modern Updates, and Room to Grow! Charming traditional two-story home in Highland offers a wonderful blend of classic character, recent improvements, comfortable living spaces, and exciting possibilities for its next owner. With three bedrooms, three bathrooms, an attached two-car garage, and an unfinished basement ready for your ideas, this home offers space, convenience, and flexibility to fit a variety of lifestyles. The main level features a spacious living and dining area that provides a welcoming setting for everyday living, family gatherings, and entertaining friends. An updated kitchen adds a refreshed feel and provides a functional space for preparing meals and spending time together as well as gorgeous cabinetry, Butcher Block Counters, Newer Appliances, Eat-In Area and Nice "Prep Space"! A convenient half bath and immediate garage access on the main floor adds practicality for both residents and guests. Inviting Outdoor Living space, Sliding glass door opens onto the level backyard deck, creating an easy connection between indoor and outdoor living. Whether you enjoy morning coffee outside, summer barbecues, or relaxing evenings with family and friends, the deck offers an appealing extension of the home's living space. The welcoming front porch and freshly painted front door further enhance the home's curb appeal. Upstairs, you'll find three bedrooms, a dedicated laundry area, and a spacious primary suite featuring a recently updated private en-suite bathroom & Walk-In Closet. The primary suite provides a comfortable retreat, while the additional bedrooms offer flexibility for family members, guests, a home office (built-in cabinets), or hobby space. With three bathrooms throughout the home, the layout offers added convenience for busy mornings, visiting guests, and daily household routines. One of the home's biggest attractions are the many recent updates, offering buyers a refreshed home with several major improvements already completed. New roof (3/26), New siding (3/26) Refreshes the home's exterior appearance and contributes to its overall curb appeal. New HVAC system (2025), New sliding glass door Enhances access to the backyard deck and improves the connection between indoor and outdoor spaces. Fresh interior paint throughout (10/26), Freshly painted front door (10/26) Adds a welcoming finishing touch to the home's exterior and Updated kitchen (2/2025). The Unfinished Basement offers Additional Space and Future Potential Living Space. The attached two-car provides convenient parking. Classic two-story character, the traditional layout offers a familiar, functional design with opportunities to make the home reflect the next owner's personal style. A Wonderful Opportunity in Highland.

1110 Tulip Ln, Highland

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Listings courtesy of Mid America Regional Information Systems Internet Data Exchange as distributed by MLS GRID.

Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.

Highland Real Estate

Newest Listings in Highland

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