Highland DIST 5 Homes for Sale

Highland DIST 5 Homes for Sale

Welcome to Highland District 5 in beautiful Madison County, Illinois! This charming area is known for its top-tier educational opportunities, making it an ideal choice for families seeking a nurturing environment for their children. Highland District 5 prides itself on its commitment to academic excellence, offering a range of programs designed to foster learning and personal growth. With dedicated teachers and a supportive community, students thrive in a setting that encourages exploration and innovation.

The schools within Highland District 5 are characterized by their small class sizes, allowing for personalized attention and a strong sense of community. Parents can rest assured knowing their children are receiving a quality education in a safe and engaging atmosphere. From innovative STEM programs to a variety of extracurricular activities, Highland District 5 cultivates well-rounded individuals prepared for future success.

As you explore homes for sale in this desirable area, you’ll find a diverse selection of properties that cater to various lifestyles and budgets. Whether you’re looking for a cozy single-family home or a spacious residence perfect for entertaining, Highland offers a wealth of options to suit your needs. The picturesque neighborhoods are complemented by beautiful parks, recreational facilities, and a welcoming community spirit.

Living in Highland District 5 not only means access to quality education but also a vibrant lifestyle filled with charm and convenience. Don’t miss the opportunity to become a part of this exceptional community—your dream home awaits in Highland, Illinois!

Newest Highland DIST 5 Homes for Sale

$197,500
3 Beds ⋅ 2 Baths ⋅ 26048664 MLS ⋅ ACTIVE Status
TURN KEY READY! Spacious Rooms with large closets throughout. Corner Lot with a large back yard. Laundry room and mud room right off the kitchen. Attached 2 car garage with a 29 x 10 workshop. New carpeting in Primary Bedroom and laminate flooring throughout.

510 W Douglas St, New Douglas
$250,000
3 Beds ⋅ 2 Baths ⋅ 26047662 MLS ⋅ ACTIVE Status
Welcome to 3535 Pierland Drive, Pocahontas! This three bed, two bath home is picture perfect and ready to move right in! Imagine sipping coffee or tea as you start your day on the dreamy covered front porch. The front door welcomes you into the invitingly open living room, dining, and kitchen. To the right of the dining area is the laundry room, full bath, and access to the garage. To the left is the hallway for the bedrooms and second bathroom. This lovely home has been completely renovated since 2019 in all the right ways from the detailed walls to the expansive kitchen. Could you even fill all those cabinets?? The massive countertop space just beckons you to roll out cookies and prepare loaves of sourdough! Step out through the sliding glass doors beyond the dining room to relax and entertain on your 12x16 composite back deck (built in 2007). You'll love the ease of maintaining a level back yard completely enclosed with vinyl fencing. Mature shade trees and beautiful landscaping make the whole space cozy even though it's so spacious. The oversized two-car garage has room for everything! The floor in the attic space above has even been reinforced for additional storage. Additionally, a new roof was installed in April 2025 and the crawl space vapor barrier replaced in Aug 2023. This one is going to go quickly, my friends! Contact your favorite agent for a private showing (beginning Thurs) or attend the OPEN HOUSE this Sunday, August 2nd from 1-4pm. professional photos to be posted by Friday.

3535 Pierland Dr, Pocahontas
$410,000
3 Beds ⋅ 1 Baths ⋅ 26047840 MLS ⋅ ACTIVE Status
Properties like this are few and far between. Tucked away on 2.5 beautiful acres, this one-of-a-kind country retreat offers the perfect blend of rural charm, modern comfort, and a lifestyle that's becoming harder to find. The inviting 3-bedroom farmhouse is full of character and feels like home the moment you walk through the door. Warm, welcoming, and surrounded by peaceful countryside, it's the kind of place where you can slow down, enjoy the view, and make memories for years to come. Step outside and you'll discover what makes this property truly special. Designed for horse lovers, hobby farmers, or anyone wanting more space to live, the property features fenced pasture and dry lot areas, a 5-stall horse barn, a chicken coop, dog kennel, garden space, and multiple outbuildings ready for whatever your lifestyle demands. The entertainment barn is the centerpiece of it all. The spacious loft has been transformed into the ultimate gathering space with a custom bar, pool table, basketball hoop, and plenty of room to host family and friends in every season. Whether you're celebrating holidays, watching the big game, or simply enjoying a weekend together, it's a space that few properties can offer. Afterward, unwind in the dedicated hot tub room and enjoy everything this incredible property has to offer. Opportunities to own a property that combines a charming farmhouse, usable acreage, equestrian amenities, and an entertainment space like this are incredibly rare. Located just minutes from Highland and Edwardsville with convenient access to St. Louis, this is more than just a home—it's the country lifestyle you've been waiting for.

9965 Fruit Rd, Alhambra
$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
$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
$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
$695,000
3 Beds ⋅ 2 Baths ⋅ 26031882 MLS ⋅ ACTIVE Status
Experience country living at its finest with this Custom Build Home and Pole Barn on 5.09 acres. A welcoming wraparound porch sets the tone, offering morning coffee spots and evening sunsets. The bright, open interior features a well-appointed kitchen with spacious living and dining areas for gatherings, and comfortable bedrooms with plenty of natural light. Endless possibilities with 2 Main Level Bonus Rooms, one on each side of the home, perfect for office space, extra entertaining area or hobbies. The Upper Level is also plumbed for a 3rd bathroom, Geothermal Furnace, Gas Fireplace, and Roof 2024. Pole Barn is 40X60, 220 hookup with an enclosed Lean-to, and separate well pump. Thoughtful touches and quality finishes create a warm, move-in ready atmosphere. Outside, the expansive yard, mature landscaping, Pecan Trees, and potential for gardens, or outdoor enjoyment and homestead living. Conveniently located yet private, this property marries rural tranquility with everyday comfort.

14218 Schuster Rd, Pocahontas
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