Highland Homes for Sale

Highland Homes for Sale

Welcome to Highland, Illinois – a charming city nestled in the heart of Madison County, where small-town warmth meets modern convenience. Known for its rich history and vibrant community spirit, Highland offers a delightful blend of picturesque landscapes and a welcoming atmosphere. With its tree-lined streets, friendly neighbors, and a strong sense of community, it's no wonder that many people are calling Highland home.

Highland is conveniently located just a short drive from the bustling city of St. Louis, making it an ideal choice for those seeking a peaceful retreat without sacrificing access to urban amenities. The city boasts an array of parks, recreational facilities, and local shops, ensuring there’s always something to do. Families will appreciate the highly-rated schools and a variety of community events throughout the year, fostering a strong connection among residents.

If you’re in the market for a new home, Highland has a diverse selection of properties for sale that cater to various tastes and budgets. From charming single-family homes with spacious yards to modern townhouses and cozy bungalows, there’s something for everyone. Whether you’re a first-time homebuyer or looking to upgrade, Highland's real estate market offers ample opportunities to find your dream home.

Explore the beauty and charm of Highland, where quality living meets affordability. With its friendly community, excellent amenities, and a range of homes for sale, Highland is ready to welcome you home. Discover your perfect property today and experience all that this delightful city has to offer!

Newest Highland Homes for Sale

$235,000
5 Beds ⋅ 2 Baths ⋅ 26047836 MLS ⋅ ACTIVE Status
NO SHOWINGS. DO NOT DISTURB OCCUPANTS. Welcome to 1700 Olive Street in Highland, where timeless character and everyday functionality come together in a convenient location. Offering approximately 1,910 square feet of living space, this home features a layout that provides flexibility for a variety of living arrangements. Natural light fills the interior, creating inviting spaces for daily living, entertaining, or working from home. Situated on a manageable lot, the property offers outdoor space for gardening, recreation, or relaxing while remaining easy to maintain. Its location provides convenient access to Highland's historic downtown, shopping, dining, and major roadways, making commuting and everyday errands simple. This Highland home is ready for its next chapter. ALL information is deemed reliable but is not guaranteed and should be verified by the buyer and/or buyers agent before making an offer.

1700 Olive St, Highland
$339,900
3 Beds ⋅ 3 Baths ⋅ 26046471 MLS ⋅ COMING SOON Status
Luxury meets timeless elegance in this one of kind full brick villa. Rich travertine tile sets the tone in the inviting living room. The vaulted great room flows into the beautifully updated kitchen featuring stunning Brazilian quartzite countertops, farmhouse sink, and designer faucet.(2025) Convenient main floor laundry includes washer and dryer. The private primary suite offers a spa inspired bath with double bowl vanity, jetted tub and walk-in closet. The finish lower level expands your living space with a spacious family room featuring a wet bar( separate freestanding sink) third bedroom, full bath and a dedicated room with refrigeration in place for a wine cellar or tasting room. Unwind on the covered patio while enjoying peaceful views of neighboring corn fields. This exceptional villa with custom finishes is truly one of a kind. Seller will have lot surveyed with new PID prior to closing.

125 Warren Mnr Unit B, Highland
$565,000
5 Beds ⋅ 3 Baths ⋅ 26045112 MLS ⋅ ACTIVE Status
Welcome home! Beautifully updated and maintained, 5 bedroom ranch, 2 acres, and large outbuilding! Enter into an open, vaulted, great room with gas fireplace. Spacious open kitchen with new quartz countertops (2026), large island with breakfast bar, and beautiful cabinetry. New kitchen and living floor (2025). The primary bedroom is located on its own wing, and features luxury upgrades with a large walk-in closet, patio access, and bathroom remodeled in 2022. Two additional spacious bedrooms are found on the main level, and the lower level includes two more bedrooms, for a total of 5 bedrooms. Lower level boasts plenty of space for relaxing or entertaining with a spacious family room and recreation area. The lower level bonus room makes a great gym or home office. Enjoy the scenic 2 acre lot from the composite deck. Plenty of space for storage, fun, and projects in the 30 x 45 detached outbuilding, which includes a bar for entertaining. An additional storage shed is perfect for mower storage. The best of subdivision living combined with a rural feel. Many updates since the home was built in 2015, including roof (2024), sump pump (2022), septic aerator replaced (2024), water heater (2021), and several rooms with new flooring. This home is a must see!

3099 Final Dr, Highland
$349,900
4 Beds ⋅ 3 Baths ⋅ 26046556 MLS ⋅ ACTIVE UNDER CONTRACT Status
MOVE IN READY!! Completely Remodeled including New Roof and Deck, Situated on a beautiful 1-acre lot, this stunning 4-bedroom, 3-bath home has been completely remodeled from top to bottom and offers the perfect combination of modern updates and spacious living. The bright, open floor plan features a gorgeous new kitchen with white cabinetry, solid surface countertops, stainless steel appliances, and a large breakfast bar overlooking the dining and living areas. Multiple living spaces, including a spacious family room with a beautiful brick fireplace, provide plenty of room for entertaining or relaxing. The updated bathrooms showcase stylish finishes, while the generously sized bedrooms offer comfort for the whole family. Step outside to enjoy the large deck overlooking the private backyard, mature trees, and peaceful surroundings. The attached garage and ample storage complete this incredible property. If you're looking for a turnkey home with modern finishes, plenty of space, and a country feel just minutes from town, this is one you won't want to miss!

4624 State Route 160, Highland
$245,000
2 Beds ⋅ 2 Baths ⋅ 26044510 MLS ⋅ ACTIVE Status
Welcome home to 45 Chase Way Dr. in Highland! This well-maintained 2-bedroom, 2-bath home is situated on a desirable corner lot and offers comfortable living with plenty of room to grow. Step inside to an inviting living room featuring cathedral ceilings and a cozy gas fireplace. The spacious primary bedroom includes an attached private bathroom with a convenient step-in shower. Enjoy outdoor living on the rear deck, and appreciate the convenience of the attached 2-car garage. Major exterior updates provide added peace of mind, including a new roof, siding, and windows in 2025, along with fresh interior paint. The unfinished basement offers incredible potential with 9-foot walls, an egress window, and plumbing already stubbed for an additional bathroom—ready for you to create additional living space, bedrooms, a recreation room, or whatever best fits your needs. With its thoughtful layout, recent updates, and excellent potential for future expansion, this Highland home is ready for its next owner.

45 Chase Way, Highland
$439,000
4 Beds ⋅ 3 Baths ⋅ 26045426 MLS ⋅ ACTIVE Status
Welcome to this stunning, fully remodeled 4-bedroom, 3-bath quad-level home situated on 2 beautifully landscaped acres. Step through the new mahogany front door with sidelights to discover new flooring, modern fixtures, and thoughtful updates throughout. The impressive kitchen features soft-close cabinetry, quartz countertops, and stainless steel appliances, while all three bathrooms have been completely renovated. Enjoy two inviting living spaces, each featuring a cozy gas fireplace. The spacious sub-basement provides abundant storage and offers excellent flexibility as a second family room, recreation room, home gym, or hobby space. Exterior improvements include a roof less than one year old, new siding, new garage doors, and new rear concrete sidewalks and patio. Additional highlights include an attached 2-car garage, covered front porch, back patio, and charming gazebo. With extensive updates, generous living space, and a peaceful 2-acre setting, this move-in-ready home is a must-see! Agent Owned!

5573 State Route 160, Highland
$334,900
3 Beds ⋅ 2 Baths ⋅ 26045122 MLS ⋅ ACTIVE Status
Want the look and feel of new construction? This completely renovated home is a must see. Spacious entry foyer welcomes you into the great room featuring gas fireplace flanked by windows that fill the space with natural light. The updated kitchen showcases a modern design with new white cabinetry and countertops. The primary suite offers a generous walk-in closet and renovated bath with new vanity (2026) and shower. Stylish luxury vinyl plank flooring flows throughout the main level with new carpet (2026) in each of the bedrooms. The lower level is ready for future expansion with an egress window and bath plumbing in place. Major replacements include furnace, water heater, and sump pump (2026). Roof replaced (2025). Enjoy these modern updates designed for today.

70 Bridgewater Ln, Highland
$450,000
3 Beds ⋅ 3 Baths ⋅ 26044281 MLS ⋅ ACTIVE UNDER CONTRACT Status
One of a Kind Custom Country Home with Exceptional Craftsmanship! Experience the warmth, character, and timeless quality of this truly one of a kind custom built home, thoughtfully designed by its original owner and lovingly crafted by the family. Situated on 9+ acres with a blend of timber and pasture, this 3 bedroom, 3 bathroom property offers breathtaking country views, abundant wildlife, and convenient access to Rt. 40. Inside, you'll find extraordinary craftsmanship throughout. The walls are finished with 3/4 inch tongue and groove walnut, cherry, and oak paneling harvested directly from the property. Distinctive hand chiseled interior brickwork adds warmth and character throughout the home. The spacious family room features angled windows designed to reduce glare and heat transfer while filling the space with natural light and showcasing the surrounding countryside. Every closet is cedar lined with built in lighting, and the attached garage includes a service pit for convenient vehicle maintenance. Outside, the home is full brick with Andersen windows, and is accented by five custom stone pillars, a unique personal touch incorporated into the original design. A 60' x 80' equipment shed with electric and concrete floor, provides excellent space for equipment, storage, or hobbies. Deer are frequent visitors, making this a peaceful country retreat. All kitchen appliances stay, making this exceptional home move in ready. Combining remarkable craftsmanship, thoughtful design, and beautiful acreage, this is a rare opportunity to own a truly unique property. Property is being sold "AS-IS"

11405 Lake Rd, Highland
$200,000
3 Beds ⋅ 3 Baths ⋅ 26039455 MLS ⋅ ACTIVE Status
Welcome to 24 Cardinal Lane in Highland! This 3-bedroom, 2.5-bath home offers a functional floor plan, generous living spaces, and endless potential to make it your own. The primary bedroom features a private half bath, while the partially finished walk-out lower level provides additional living space, a bathroom, laundry area, and plenty of storage. Whether you're looking for a family room, home office, recreation space, or room to expand, the flexible lower level offers countless possibilities. Plus, enjoy added peace of mind knowing the roof is only 5 years old. Conveniently located in an established neighborhood close to schools, parks, shopping, and dining, this home is ready for its next chapter. Bring your ideas and make it your own!

24 Cardinal Ln, Highland
$270,000
4 Beds ⋅ 3 Baths ⋅ 26043129 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome Home to comfort and functionality! On a spacious corner lot, at 155 Keeven Dr, sits a full brick ranch home in Highland School District 5. Inviting 20'x6' concrete porch. Three full bathrooms. Main floor laundry. Three bedrooms on main level with a 4th non-conforming bedroom (no egress window) downstairs with a large closet! Well-appointed kitchen provides plenty of counter area for meal prep and abundant cabinet space. Separate dining room features a beautiful crystal chandelier and flows in the living room complete with a homey gas fireplace. Patio door from the Living Room leads to the 13'x14' concrete patio perfect for day or night! Downstairs you'll find additional living space! Family room with a wet bar welcomes entertaining family and friends or just relaxing! Gas Heatilator fireplace adds ambiance to the family room area! 19' x 24' mechanical/storage area completes the basement. Oversized, 2 car attached garage. New roof 2025. School Bus Stop right across the street at Keeven and Sunfish! Check out the lake view from the living room and patio!! Contact your favorite Real Estate Agent for a private tour. And then, be ready to pack up and move in. Thank you.

155 Keeven Dr, Highland
$140,000
3 Beds ⋅ 1 Baths ⋅ 26042098 MLS ⋅ ACTIVE Status
Step into a piece of history at 407 S. Mulberry in Grantfork! Nestled on approximately one beautiful acre in the Highland School District. This charming 120+ year-old farmhouse is a rare opportunity to own a property full of character and self-sustaining beauty- ready to make your own. From the moment you arrive, you'll fall in love with the opportunities of a covered front porch and picturesque setting surrounded by mature trees, native landscaping, and thriving gardens. The land is a gardener's dream, featuring cherry, pear, apricot, and multiple varieties of apple trees, elderberry bushes, a squash and pumpkin patch, and plenty of space to enjoy nature year-round. A charming chicken coop adds to the property's homestead appeal. Inside, timeless details shines through with some original hardwood floors, beautiful bead board features and ceilings, and many original architectural details that preserve the home's historic charm while creating a warm atmosphere. Upstairs has been mostly gutted with the plan to make it a true family home of 4 spacious bedrooms. Additional highlights include an oversized two-car garage, established garden areas, abundant outdoor space, and a peaceful setting that's hard to find while still offering the convenience of living right outside of Highland. Whether you've dreamed of hobby farming, gardening, raising chickens, homesteading, or simply enjoying the beauty of a classic farmhouse, this one-of-a-kind property offers endless possibilities. Come experience the charm, character, and tranquility that make this special home unlike anything else.

407 S Mulberry St, Highland
$235,000
2 Beds ⋅ 2 Baths ⋅ 26042391 MLS ⋅ ACTIVE UNDER CONTRACT Status
A VILLA TO LOVE! This villa in Faith Countryside area is on a beautiful lot with mature trees and an open backyard. This home is very well kept with an open floor plan with cathedral ceilings throughout and sky lights making everything bright. The beautiful real oak floors give a warm inviting feeling. The sunroom off the dining area gives an expansive view and a wonderful outdoor feeling. Newer HVAC and kitchen appliances. 100 amp breakers. Ceiling fans throughout. The oversize garage gives storage space and "no-step" access to the kitchen. Faith Countryside is a senior villa area, 55yrs and up. COME SEE - YOU'LL LIKE IT!

4 Latzer, Highland
Start Your Search