Madison, IL Homes

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  /99

  $1,329,000

  • 6 Beds
  • 5 Baths
  • 8,680 Sq Ft

  13642 Saint Rose Rd, Highland, IL 62249

  This exceptional property offers the perfect blend of luxury, privacy, and recreation—all just minutes from town. Set on 14 beautifully maintained acres, it features a stocked pond, saltwater pool, and lush landscaping that gives the estate a resort-like feel. Inside, the spacious chef’s kitchen is designed for entertaining, while large windows flood the home with natural light. The private

  Justin Bruehl LIVING THE DREAM INC.

  

  13642 Saint Rose Rd, Highland, IL 62249
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  Explore Highland

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  /15

  $680 - $800 per month

  Flax Meadow Townhomes

  2 - 3 Beds

  216 Flax Dr, Highland, IL 62249

  Equal Housing Opportunity Statement: We are pledged to the letter and spirit of U.S. policy for the achievement of equal housing opportunity throughout the Nation. We encourage and support an affirmative advertising and marketing program in which there are no barriers to obtaining housing because of race, color, religion, sex, handicap, familial status, or national origin.

  216 Flax Dr, Highland, IL 62249
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  /47

  $127,500 Sold Aug 04, 2025

  • 1,941 Sq Ft
  • $66/SF
  • 5 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1920

  218 Walnut St, Highland, IL 62249

  Charming 2-story traditional home in the heart of Highland! Features include a kitchen with breakfast bar, dining area, main-floor laundry & mudroom, a spacious half bath with room to expand, and a huge family room. Two bright flex spaces can serve as dining, living, or a potential bedroom. Upstairs offers 2 large bedrooms, 1 full bath, and a versatile loft perfect for an office, den, or 3rd

  Amanda Stehlik Equity Realty Group, LLC

  218 Walnut St, Highland, IL 62249
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  /19

  Est $195,393 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,275 Sq Ft

  90 Sunbeam Dr Unit B, Highland, IL 62249

  90 Sunbeam Dr Unit B, Highland, IL 62249
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  /38

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 2,463 Sq Ft

  1905 Zschokke St, Highland, IL 62249

  Your Next Chapter Starts on Zschokke! Welcome to this well-maintained 3-bedroom, 1.5-bath all-brick home situated on a spacious, beautifully landscaped lot. Offering a flexible floor plan, this home features a versatile main-level room that can easily serve as a 4th bedroom, home office, or guest space. Step inside to find a stylish eat-in kitchen complete with quartz countertops, luxury vinyl

  Lori Reid Gardner Century 21 Reid Baugher Realty

  1905 Zschokke St, Highland, IL 62249
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  /17

  $1,600 per month

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • Townhouse for Rent

  723 Sycamore St Unit A, Highland, IL 62249

  Three Bedroom Townhouse with Partially Finished Walk Out Basement, Vaulted Ceilings, 18 x 10 Living Room, 11 x 10 Kitchen with Breakfast Island Provides Glass Top Electric Range with Built In Microwave, Dishwasher, Garbage Disposal and Refrigerator, 11 x 10 Dining Room, Half Bathroom, 13 x 12 Master Bedroom with Walk In Closet and Private Bathroom, 13 x 8 Second Bedroom, Lower Level Includes 455

  Christopher Mendola Christone Enterprises, Inc.

  723 Sycamore St Unit A, Highland, IL 62249
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  /49

  $305,000 Sold Aug 01, 2025

  • 1,968 Sq Ft
  • $155/SF
  • 7 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1993

  170 Coventry Way, Highland, IL 62249

  WOW!!! Beautiful open 2 Story entrance into Living rm with tall ceiling open to loft & open stairway to upper level. Main floor Master Suite with walk-in closet. Master BA has nice walk-in shower. Kitchen features quartz countertops, backsplash, SS appliances, pantry. Breakfast rm has door to maintenance free deck, patio & shed. Main floor Laundry rm (W & D) stay. Newer laminate flooring in

  Sue Wurth Equity Realty Group, LLC

  170 Coventry Way, Highland, IL 62249
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  /55

  Est $216,072 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  1208 Main St, Highland, IL 62249

  1208 Main St, Highland, IL 62249
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  /45

  $335,000

  • 3 Beds
  • 2.5 Baths
  • 2,630 Sq Ft

  2364 Marine Rd, Highland, IL 62249

  Welcome to your dream retreat! This charming rural ranch home sits on a spacious 0.66-acre lot and offers the perfect blend of comfort, space, and functionality. With an attached 2-car garage, detached 4-car garage, and two carports, there’s plenty of room for vehicles, toys, or hobby space—plus ample parking for guests. Inside, you’ll find 3 bedrooms and 2 full baths on the main level, including

  Amanda Stehlik Equity Realty Group, LLC

  2364 Marine Rd, Highland, IL 62249
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  /7

  $850 per month

  • 1 - 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  508 Broadway Unit 506, Highland, IL 62249

  Conveniently located on Broadway, across from Michael's. Designated street parking out front, but plate window faces street.

  508 Broadway Unit 506, Highland, IL 62249
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  /27

  $225,800 Sold Aug 01, 2025

  • 1,782 Sq Ft
  • $127/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  11602 State Route 143, Highland, IL 62249

  3 bedroom brick ranch on 2.18 acres. Needs TLC, but can easily be brought back to its former condition. Main floor laundry could be a 4th bedroom . Laundry hookups located in lower level as well.The full basement could be finished to include a family room, game room and much more! Fenced back yard, 14 x 20 metal Storage building on a concrete slab has a riding lawnmower and wagon that are

  George Key RE/MAX Alliance

  11602 State Route 143, Highland, IL 62249
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  /57

  Est $618,301 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 5,804 Sq Ft

  2321 Park Hill Dr, Highland, IL 62249

  2321 Park Hill Dr, Highland, IL 62249
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  /47

  $465,000

  • 3 Beds
  • 2.5 Baths
  • 2,708 Sq Ft

  4303 State Route 160, Highland, IL 62249

  4.44 ACRES OF BEAUTIFUL TREES ADJOINING HIGHLAND SILVER LAKE! All brick home, remodeled kitchen in 2020, hardwood floors. The double sided masonry gas FP adds to the living room and first floor family room, with another masonry woodburning FP in the downstairs rec room. The laundry/mud room is just off the kitchen and inside the back door to the pool. The property includes a 30x40 outbuilding

  Lois Cremin Equity Realty Group, LLC

  4303 State Route 160, Highland, IL 62249
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  /14

  $215,000 Sold Jul 31, 2025

  • Land
  • 11 Acres
  • $19,963 per Acre

  • 8 Days On Market

  3672 State Route 160, Highland, IL 62249

  Rare find! 10.77 acres with outbuilding less than 2 miles north of Highland city limits! Consisting of two parcels one is 5.03 acres and the other is 5.74 acres. The 30 x 40 pole barn is located on the 5.03 acres and has electric service from the City of Highland and a water line (not currently used) from the Village of Grantfork. 5.74 acre parcel adjoins on the south. Approximately 6 acres

  Diane Korte-Lindsey Coldwell Banker Brown Realtors

  3672 State Route 160, Highland, IL 62249
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  /18

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,089 Sq Ft

  35 Colonial Manor Dr Unit B, Highland, IL 62249

  35 Colonial Manor Dr Unit B, Highland, IL 62249
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  /58

  $700,000

  • 4 Beds
  • 3.5 Baths
  • 4,090 Sq Ft

  112 Verrazanno, Highland, IL 62249

  EXQUISITE, CUSTOM-BUILT, FULL BRICK, SINGLE OWNER HOME IN THE COVETED STONEBRIDGE ESTATES! This STUNNING, LAKE-FRONT home was built with QUALITY & tons of 'BELLS & WHISTLES"! Upon arrival you'll be ENCHANTED by the "Look" of this 3-Car, Side Load Garage BEAUTY! Front Porch Entry is Uniquely Highlighted by the "forward thinking" Front Door and is just the BEGINNING of SO MANY AMAZING FEATURES!

  Kim Johnson Equity Realty Group, LLC

  112 Verrazanno, Highland, IL 62249
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  /37

  $165,000 Sold Jul 30, 2025

  • 1,577 Sq Ft
  • $105/SF
  • 0 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1965

  716 Sycamore St, Highland, IL 62249

  Welcome to this DELIGHTFUL & CONVENIENTLY located Ranch Home in the "Heart of Town"! This Charmer is "Move-In" ready and has SO MANY nice updates/features that include a Spacious Living Room highlighted with Plenty of "Natural Lighting", 3 beds (Closet Organizers)/1 Full (recently updated) Hall Bathroom (tub/shower combo), Open Kitchen/Dining, with a Full Basement! Hardwood & Newer LVP/Tile

  Kim Johnson Equity Realty Group, LLC

  716 Sycamore St, Highland, IL 62249
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  /36

  Est $329,642 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,537 Sq Ft

  130 N Porte Dr, Highland, IL 62249

  130 N Porte Dr, Highland, IL 62249
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  /36

  $305,000

  • 3 Beds
  • 2 Baths
  • 2,432 Sq Ft

  2 Stone Dr, Highland, IL 62249

  Welcome to the best of both worlds—peaceful country vibes with modern upgrades and city utilities! This 3-bedroom, 2-bath ranch sits on a spacious lot just outside Highland, offering the perfect blend of privacy and convenience.Step inside to soaring vaulted ceilings and gorgeous bamboo hardwood floors in the open-concept great room. The kitchen impresses with stainless steel appliances,

  Chris Kelly Real Broker LLC

  2 Stone Dr, Highland, IL 62249
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  /83

  $225,000 Sold Jul 30, 2025

  • 2,260 Sq Ft
  • $100/SF

  • 4 Beds
  • 2.5 Baths
  • Built 1928

  607 9th St, Highland, IL 62249

  Discover this elegant historic era home in the HEART of TOWN featuring 3 levels of finished living space! Full Brick BEAUTY with Large, Detached Amish Garage (Alley Access) and Fenced Yard! Step inside to the enormous & SPACIOUS Main Floor highlighted nicely with a large Living, Dining, Office, Kitchen, Bedroom, Full Bath (Step in Shower) & Laundry Room. You'll LOVE the BEAUTIFULLY remodeled

  Kim Johnson Equity Realty Group, LLC

  607 9th St, Highland, IL 62249
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  /68

  Est $480,681 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft

  2799 Water Lily Ln, Highland, IL 62249

  2799 Water Lily Ln, Highland, IL 62249
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  /27

  $274,000

  • 3 Beds
  • 2 Baths
  • 1,972 Sq Ft

  3 Noel Ln, Highland, IL 62249

  **Back on Market**No fault to seller...Come view this brick 3 bedroom, 2 bath home with 2 brick wood burning fireplaces located in the living room and basement. Very large master bedroom. 2 car attached garage located on cul-de-sac on the edge of town. Eat-in kitchen features pantry, cook top, double oven, microwave, dishwasher, refrigerator. Basement unfinished with lots of storage and great

  Jaclyn Delaney eXp Realty

  3 Noel Ln, Highland, IL 62249
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  /34

  $428,500 Sold Jul 30, 2025

  • 2,011 Sq Ft
  • $213/SF
  • 53 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2022

  108 Baileys Ct, Highland, IL 62249

  Modern Elegance Meets Everyday Comfort in Highland, IL!Step into this stunning open-concept home, perfectly positioned on a quiet cul-de-sac and designed to impress from the moment you walk in. Soaring vaulted ceilings create a grand sense of space in the expansive great room and kitchen, where sleek solid surface countertops and modern finishes elevate the entire living experience. The

  Boyd Jenningss Keller Williams Marquee

  108 Baileys Ct, Highland, IL 62249
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  /11

  Est $65,779 Not Listed For Sale

  1040 Buckeye Crossing, Highland, IL 62249

  1040 Buckeye Crossing, Highland, IL 62249
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  /18

  $425,000

  • 5 Beds
  • 3 Baths
  • 4,732 Sq Ft

  1312 Old Trenton Rd, Highland, IL 62249

  Step back in time to when homes were built to last for generations to come! This 1870 Victorian inspired, Colonial Revival was built by one of Highland's founding families and sits on 1.03 acres adjacent to a park with walking trails. Adjoining 2.06 parcel can be sold separately for $60,000 or combined with this parcel for $475,000 total. Step inside to discover 11 spacious rooms, 2 open

  Diane Korte-Lindsey Coldwell Banker Brown Realtors

  1312 Old Trenton Rd, Highland, IL 62249
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  /54

  $385,000 Sold Jul 25, 2025

  • 2,180 Sq Ft
  • $177/SF
  • 6 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1984

  36 Kay Dr, Highland, IL 62249

  Discover this perfect blend of comfort and functionality with this delightful 3-bedroom, 2-bath home nestled on a serene 1-acre lot. Offering a spacious layout and a host of unique amenities, this property is ideal for families, hobbyists, or those seeking a tranquil retreat. Outbuilding Galore: Several sturdy garages on the property that offer endless possibilities for storage, workshops, or

  Shelly Tite Tarrant and Harman Real Estate and Auction Co

  36 Kay Dr, Highland, IL 62249
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  /3

  Est $42,383 Not Listed For Sale

  1049 Buckeye Crossing, Highland, IL 62249

  1049 Buckeye Crossing, Highland, IL 62249
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  /43

  $374,900 New Construction

  • 2,320 Sq Ft

  4955 Fitz James Crossing, Highland, IL 62249

  Brand new and ready to move in! This 4 bedroom, 3 bath home sits on a large corner lot and features an open concept main floor with a spacious living room, dining area, and kitchen complete with granite countertops, under-mount sink, stainless appliances, and center island. The main floor includes a master suite with a private bath and 5-ft shower, two additional bedrooms, a full hall bath, and

  Carl Henrichs Equity Realty Group, LLC

  4955 Fitz James Crossing, Highland, IL 62249
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  /39

  $445,000 Sold Jul 25, 2025

  • 2,012 Sq Ft
  • $221/SF
  • 13 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1920

  13649 Pocahontas Rd, Highland, IL 62249

  Open House canceled! Discover your dream "Mini Farm" on 5 BEAUTIFUL acres! Fully rehabbed (down to studs) in 2010! You will be "DELIGHTED" upon arrival at this GORGEOUS HOME! Lovely Front or Side Porch (recently finished) to Relax in the "Lazy Days of Summer" Extraordinary Main Floor Highlights include Spacious Living Room/Dining Room with immediate Access to the "Dream Kitchen" complete with

  Kim Johnson Equity Realty Group, LLC

  13649 Pocahontas Rd, Highland, IL 62249
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  /3

  Est $58,333 Not Listed For Sale

  1019 Buckeye Crossing, Highland, IL 62249

  1019 Buckeye Crossing, Highland, IL 62249
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  /41

  $369,500 Pending

  • 5 Beds
  • 3.5 Baths
  • 2,858 Sq Ft

  105 N Porte Dr, Highland, IL 62249

  The One You Have Been Waiting For!! Sought after neighborhood and so many great features! Open floor plan living area on main floor, primary suite on one side with additional bedrooms and full bath on the other. Kitchen features stainless appliances, under cabinet lighting, soft close doors and a large island. The sunroom offers additional living area opening up to a stamped concrete patio,

  Diane Korte-Lindsey Coldwell Banker Brown Realtors

  105 N Porte Dr, Highland, IL 62249
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  /43

  $189,900 Sold Jul 24, 2025

  • 2,168 Sq Ft
  • $88/SF
  • 0 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1948

  1404 Lemon St, Highland, IL 62249

  Welcome home to this adorable residence offering 3 bedrooms and 2 bathrooms with the possibility of adding another bedroom and bathroom in the lower level. Situated in the heart of Highland, walking distance to shopping, dining, schools and more. Enjoy a level, fully fenced in backyard perfect for entertaining or pets. As well as the 1 car detached garage with large workshop attached. Large

  Ashley Cress RE/MAX Alliance

  1404 Lemon St, Highland, IL 62249
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  /15

  Est $323,272 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft

  1120 Tulip Ln, Highland, IL 62249

  1120 Tulip Ln, Highland, IL 62249
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  /29

  $259,900 Pending

  • 3 Beds
  • 3 Baths
  • 2,105 Sq Ft

  90 Sunfish Dr, Highland, IL 62249

  EXCELLENT-WELL MAINTAINED 3 BEDROOM/3 BATH RANCH STYLE HOME NESTLED IN TERRIFIC NEIGHBORHOOD! Featuring: Kitchen With A Breakfast Bar, Dishwasher, & Built In Microwave; TWO--LAUNDRY Rooms--One On Main & One On Lower Level; Huge Basement With A Family Room, Recreational Area, Bonus Room For A Possible 4th Bedroom & A Lower 3rd Bathroom; Unfinished 15 x 12 Storage Area Which Features A Kitchenette,

  Phil Hardas RE/MAX Alliance

  90 Sunfish Dr, Highland, IL 62249
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  /43

  $670,000 Sold Jul 23, 2025

  • 4,770 Sq Ft
  • $140/SF
  • 24 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1999

  13122 Fawn Creek Rd, Highland, IL 62249

  Welcome to 13122 Fawn Creek Rd—your private escape just 35 minutes from St. Louis. Sitting on two wooded acres in the Highland School District, this upgraded stunner is built for unforgettable gatherings and everyday comfort. The open layout showcases a spacious kitchen and living area, all flowing out to a resort-style backyard with a large patio, gazebo, and in-ground pool. The primary suite is

  Jason Hardas RE/MAX Alliance

  13122 Fawn Creek Rd, Highland, IL 62249
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  /84

  Est $510,885 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,002 Sq Ft

  2863 Wellen Rd, Highland, IL 62249

  2863 Wellen Rd, Highland, IL 62249
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  /47

  $369,900 Pending

  • 3 Beds
  • 3 Baths
  • 2,650 Sq Ft

  100 Quail Dr E, Highland, IL 62249

  Fully remodeled ENTERTAINER'S OASIS! This beautiful home offers a huge open concept living room/dining room/ kitchen area featuring engineered hardwood floors, vaulted ceiling, and french doors that open to a large 15'x24' Trex deck. The kitchen features custom maple cabinets, quartz countertops and a 4x4 island. Also on the main level are 3 bedrooms, laundry room, garage entrance and 1 full

  Emily Bierman Re/Max Alliance

  100 Quail Dr E, Highland, IL 62249
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  /50

  $462,000 Sold Jul 21, 2025

  • 2,919 Sq Ft
  • $158/SF
  • 1 Day On Market

  • 3 Beds
  • 4 Baths
  • Built 1993

  13345 Iberg Rd, Highland, IL 62249

  Tucked away in a quiet area of Highland, this beautifully updated ranch sits on 2 acres surrounded by mature trees. Step inside to brand new wood floors, fresh paint, updated lighting, and an elegant fireplace wall that adds warmth to the living space. The home offers 3 bedrooms, 2 full and 2 half bathrooms, and a finished basement with a bonus room—perfect for a home office, playroom, or guest

  Viktoriia Kovel Keller Williams Pinnacle

  13345 Iberg Rd, Highland, IL 62249
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  /35

  Est $322,381 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,509 Sq Ft

  4833 Cedar Spring Dr, Highland, IL 62249

  4833 Cedar Spring Dr, Highland, IL 62249
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  /2

  $315,000 Pending

  • 1,600 Sq Ft

  10 Arbor Crest Dr, Highland, IL 62249

  Sold before print

  Jacquelyn Poponi Real Broker LLC

  10 Arbor Crest Dr, Highland, IL 62249

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