Madisonville, KY Homes for Sale under $500,000

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  /66

  $449,500

  $66K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,060 Sq Ft

  706 University Cir, Madisonville, KY 42431

  Timeless elegance meets enduring craftsmanship in this stately brick home on University Circle. Custom-built and lovingly cared for by one family since its completion, this residence radiates warmth, grace, and quality at every turn. Refined details—rich hardwood floors, elegant molding, and custom built-ins—reflect the quality and care poured into this home. With 5 bedrooms, 4 full baths, and

  Sara Spencer Haven Realty, LLC

  706 University Cir, Madisonville, KY 42431
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  /34

  $265,000

  $95K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 3,094 Sq Ft

  1029 Princeton Rd, Madisonville, KY 42431

  In-ground pool & a Newer HVAC! This stately brick 4-bedroom, 2.5-bath home sits on a scenic 2.4-acre corner lot and features an inground pool with a brand-new pump! Perfect for summer entertaining! Inside, you'll find elegant crown and dental moldings, classic wainscoting, granite countertops, and a sunroom with luxurious travertine tile flooring. The large primary suite offers large bathroom

  Cindy Mckenzie Coldwell Banker Complete Realty

  1029 Princeton Rd, Madisonville, KY 42431
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  /11

  $350,000

  • Land
  • 32.52 Acres
  • $10,763 per Acre

  208/300 Mcleod Ln, Madisonville, KY 42431

  This 32.52 Acres with 2 rental houses is definitely a rare find due to its location. The property has so many possibilities. Could be a great property for future development, or small hunting farm. The 2 rental houses would be a great source of income as well. Call to check this one out. Chad Cunningham 270.875.5454

  Chad Cunningham Heritage Homes Real Estate

  208/300 Mcleod Ln, Madisonville, KY 42431
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  /35

  $245,000

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft

  103 E Broadway St, Madisonville, KY 42431

  Charming 1925 brick property full of character and income potential. Most recently operated as a successful Airbnb, this fully furnished property is move-in or rent-ready from day one. Previous monthly rental income was $2,221, offering a strong opportunity for investors or owner-occupants alike. The sale includes a parking lot located directly across the street, providing added convenience and

  Dean Sheets Heritage Homes Real Estate

  103 E Broadway St, Madisonville, KY 42431
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  /27

  $239,000

  • 4 Beds
  • 2.5 Baths
  • 2,027 Sq Ft

  148 Woodlawn Ct, Madisonville, KY 42431

  Welcome to 148 Woodlawn Court in Madisonville. This is an inviting 4-bedroom, 2.5-bath house nestled on a peaceful dead-end street in a quiet neighborhood. This property offers both privacy and comfort. Enjoy relaxing or entertaining in your spacious family room and separate living room, both designed with neutral colors to suit any style. The fenced backyard is perfect for kids, pets, or weekend

  Merideth Tyson Heritage Homes Real Estate

  148 Woodlawn Ct, Madisonville, KY 42431
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  /35

  $279,900

  $40K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,767 Sq Ft

  64 Calumet Ln, Madisonville, KY 42431

  Charming Home with Cathedral Ceilings, Stunning Kitchen & Dream Outdoor Living Spaces! Welcome to this beautifully updated home featuring cathedral ceilings, hardwood floors, and gorgeous shiplap and board and batten accents throughout. The completely renovated kitchen has hard surface countertops, modern cabinetry, and premium finishes—perfect for both everyday living and entertaining. The

  Maggie Sheets Heritage Homes Real Estate

  64 Calumet Ln, Madisonville, KY 42431
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  /3

  $500,000

  Pending

  • Land
  • 3.19 Acres
  • $156,740 per Acre

  110 Quinten Dr, Madisonville, KY 42431

  This location is a PRIME spot for a commercial property with the recent growth on the North side of Madisonville. The seller is preparing a site that will be brought to a grade conducive to construction! 2 PARCELS & 1/2 LOT 5 QUINTEN ADD

  Kristy Saint Coldwell Banker Complete Realty

  110 Quinten Dr, Madisonville, KY 42431
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  /41

  $430,000

  • 5 Beds
  • 3.5 Baths
  • 2,795 Sq Ft

  120 Shamrock Dr, Madisonville, KY 42431

  This beautifully upgraded home offers 2,795 square feet of thoughtfully designed living space on a spacious 1.33-acre lot. A 2022 addition created an impressive primary suite featuring a luxurious bathroom with a large soaking tub, dual vanities, a generous walk-in closet, dedicated laundry room, and a bright sunroom. Throughout the home, you'll find numerous updates including luxury vinyl

  Javin Vannoy Bhg Realty

  120 Shamrock Dr, Madisonville, KY 42431
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  /20

  $206,750

  $32K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,644 Sq Ft

  1417 Crestview Dr, Madisonville, KY 42431

  BACK ON MARKET AT NO FAULT OF THE SELLERS!Completely updated and move-in ready! This beautifully renovated 3-bedroom, 2-bath brick ranch offers over 1,600 square feet of comfortable single-level living in an established Madisonville neighborhood. The heart of the home is the spacious eat-in kitchen featuring new cabinetry, updated countertops, a large center island, refrigerator, dishwasher,

  Nathan Endres Keller Williams Realty Clarksville

  1417 Crestview Dr, Madisonville, KY 42431
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  /16

  $229,900

  $10K PRICE INCREASE

  • 4 Beds
  • 1.5 Baths
  • 1,392 Sq Ft

  1821 Ash St, Madisonville, KY 42431

  New roof being installed July 2026! Move-in ready and beautifully updated! This 4-bedroom, 1.5-bath home offers fresh updates throughout, a few to mention are - new flooring and windows, an updated kitchen, and renovated bathrooms. The spacious layout provides comfortable living with an oversized laundry room for added convenience. The kitchen features brand-new stainless steel appliances and

  Robin Duke My Ky Homes Realty

  1821 Ash St, Madisonville, KY 42431
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  /34

  $499,000

  $51K PRICE DROP

  220 Tucker Schoolhouse Rd, Madisonville, KY 42431

  6.9 acres on Pee Wee Lake featuring excellent investment potential and stunning lake views. Property includes three rental homes currently occupied and producing a combined rental income of $1700/month. Multiple potential building sites offer the perfect opportunity to construct a private residence overlooking the water. Prime location with peaceful surrounding and convenient access - Just 8

  Nathan Eaves Eaves Realty Auc-KW 1st Choice

  220 Tucker Schoolhouse Rd, Madisonville, KY 42431
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  /21

  $214,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft

  503 W Center St, Madisonville, KY 42431

  This 3-bed, 2-bath home offers the perfect blend of comfort and functionality. Situated on .26 acres, this move-in-ready home features an open-concept floor plan designed for both everyday living and entertaining. The spacious kitchen offers abundant cabinetry, a large island with bar seating, and flows seamlessly into the living area. Enjoy sitting on the covered front porch or relax on the

  Melanie White Heritage Homes Real Estate

  503 W Center St, Madisonville, KY 42431
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  /2

  $329,900

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  104 Oates St, Madisonville, KY 42431

  Welcome to 104 Oates St. At Ruby Junction! Located in a thoughtfully planned community featuring a blend of residential and commercial spaces along with shared common areas, this home offers a lifestyle that is both connected and convenient. With Construction beginning soon, an early buyer will have the opportunity to make some material & color choices along with the option of more finished

  Ginger Driver Haven Realty, LLC

  104 Oates St, Madisonville, KY 42431
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  /35

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft

  7431 Beulah Rd, Madisonville, KY 42431

  Welcome to 7431 Beulah Rd! This well-maintained 3-bedroom, 2-bath home offers approximately 1,556 sq. ft. on a spacious 1-acre lot. The home also has a 2-car attached garage, and recent updates include new laminate and tile flooring (2025), fresh interior paint (2025), a new 30-year architectural shingle roof (2024), a high-efficiency HVAC system (2024), professionally cleaned ductwork (2025), a

  April Perdue Tradewater Realty

  7431 Beulah Rd, Madisonville, KY 42431
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  /23

  $416,250

  • Land
  • 111 Acres
  • $3,750 per Acre

  0000 Curtis Mine Rd, Madisonville, KY 42431

  Waterfowl farm in proven area hot spot. This farm is low ground with great blind locations. Two ponds with great cover.

  Chad Cunningham Heritage Homes Real Estate

  0000 Curtis Mine Rd, Madisonville, KY 42431
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  /14

  $289,900

  • 3 Beds
  • 2 Baths
  • 2,040 Sq Ft

  711 Shamrock Dr, Madisonville, KY 42431

  Welcome to a 3 bed 2 bath home located on Shamrock Drive in Madisonville. This property also has a large detached storage building. Property is being sold b the executor of the Mitchell Estate.

  Allen Davis Coldwell Banker Complete Realty

  711 Shamrock Dr, Madisonville, KY 42431
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  /17

  $290,000

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  1601 Valley Dr, Madisonville, KY 42431

  Welcome home to this beautiful 4-bedroom, 2-bathroom property located in a well-established neighborhood! This move-in-ready home offers a spacious layout with a well-equipped kitchen featuring an island, and all kitchen appliances will remain with the home. Step outside to enjoy the fenced backyard with an in-ground pool—perfect for relaxing, entertaining, and making lasting memories. Situated

  Maggie Sheets Heritage Homes Real Estate

  1601 Valley Dr, Madisonville, KY 42431
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  /15

  $249,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,108 Sq Ft

  29 Salisbury St, Madisonville, KY 42431

  Well-maintained 3 bedroom, 2 bath brick home located in an established neighborhood. Situated on approximately 0.41 acres, this property offers a functional layout with comfortable living spaces throughout. Features include a 2-car attached garage and a sunroom providing additional space for relaxing or entertaining. Conveniently located near local amenities, shopping, and schools. Contact Kim

  Kim Harper Heritage Homes Real Estate

  29 Salisbury St, Madisonville, KY 42431
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  /2

  $200,000

  $65K PRICE INCREASE

  • Land
  • 38,332 Sq Ft
  • $227,273 per Acre

  0 Pebble Creek Dr, Madisonville, KY 42431

  Great location, just off of North Main Street, and just a stroll from the YMCA. This .88 acre is zoned: Neighborhood Commercial. There is another lot that borders this .88 ac. approx. the same size priced at $200,000 and 12.9 acres on the other side priced at $448,000. All totaling approximately 14.7 acres!

  Teresa Oliver Kentucky Homes Realty

  0 Pebble Creek Dr, Madisonville, KY 42431
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  /33

  $255,900

  • 10 Beds
  • 7 Baths
  • 2,946 Sq Ft

  118 S Franklin St, Madisonville, KY 42431

  Turnkey multi-family investment opportunity on S. Franklin Street in Madisonville, just a short walk to downtown shops, restaurants, and local attractions. This unique property features 3 established rental units currently operating as Airbnb properties. Unit 1 offers 2 bedrooms and 2 baths, Unit 2 features 1 bedroom, 1 bath, plus an office, and Unit 3 includes 2 bedrooms and 1 bath. Each unit

  Sara Spencer Haven Realty, LLC

  118 S Franklin St, Madisonville, KY 42431
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  /35

  $329,900

  • 3 Beds
  • 3 Baths
  • 2,246 Sq Ft

  131 Carlisle Dr, Madisonville, KY 42431

  Located on a quiet dead-end street in the desirable Tanglewood neighborhood, this well-maintained home offers over 3,000 square feet of living space and endless possibilities. The oversized living room is perfect for entertaining, while the finished basement includes a separate rec room, full bath, and private exterior access that could easily accommodate guests or separate living quarters.

  Sarah Stone Wilkes Heritage Homes Real Estate

  131 Carlisle Dr, Madisonville, KY 42431
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  /48

  $305,000

  $5K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,819 Sq Ft

  834 Homewood Dr, Madisonville, KY 42431

  Take a look at 843 Homewood Drive. This well built 5 bedroom, 3 bath ranch home has over 2800 square feet of living space. Located in a quiet established neighborhood on a shady landscaped lot you will find ample space both inside and out. With spacious rooms the home has received many updates in recent years including new roof shingles, some appliances, 2 water heaters, kitchen and foyer

  Ginger Driver Haven Realty, LLC

  834 Homewood Dr, Madisonville, KY 42431
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  /37

  $240,000

  $3K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,923 Sq Ft

  867 Legion Dr, Madisonville, KY 42431

  LISTED BELOW APPRAISAL...Beautifully updated and move-in ready, this charming 3-bedroom, 2-bath home features a warm blend of hardwood, laminate, and tile flooring throughout. The soaring cathedral ceiling enhances the open living space, complemented by two fireplaces that create inviting areas for relaxing and entertaining. The spacious kitchen/dining area with an island offers plenty of room

  Brandon Ratliff Coldwell Banker Complete Realty

  867 Legion Dr, Madisonville, KY 42431
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  /30

  $220,000

  • 4 Beds
  • 2.5 Baths
  • 1,948 Sq Ft

  273 Sugg St, Madisonville, KY 42431

  Renovated and ready, this older home offers the charm buyers love with the updates they don't want to have to do themselves. Features include new HVACs, new flooring, new windows, new cabinets, new countertops, and renovated bathrooms. The large covered porch adds great curb appeal, and the attached carport, detached garage, and two driveways give you plenty of space for parking, storage, and

  Sarah Stone Wilkes Heritage Homes Real Estate

  273 Sugg St, Madisonville, KY 42431
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  /28

  $207,400

  $13K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft

  41 N Seminary St, Madisonville, KY 42431

  This beautifully remodeled home in Madisonville, Kentucky offers the perfect blend of modern charm and functional living. Featuring 3 bedrooms and 2 bathrooms across 1,909 square feet, the home showcases stylish upgrades throughout, including quartz countertops, stainless steel appliances, recessed lighting, high ceilings, and unique modern cabinetry that adds character and sophistication. The

  Josh Parish Bhg Realty

  41 N Seminary St, Madisonville, KY 42431
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  /46

  $309,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  575 Pennyrile Dr, Madisonville, KY 42431

  Welcome to this one-of-a-kind home nestled on a peaceful dead-end road in Madisonville. This spacious 4-bedroom, 2.5-bath property offers the perfect blend of comfort, character, and functionality on a beautiful 1.3-acre lot. Inside, you'll find fresh updates throughout, including new flooring and paint, along with a large family room designed for gathering and entertaining. The finished sunroom

  Landon Black Bhg Realty

  575 Pennyrile Dr, Madisonville, KY 42431
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  /26

  $219,900

  • 3 Beds
  • 2 Baths
  • 2,010 Sq Ft

  1134 Whit Ln, Madisonville, KY 42431

  Lovely brick ranch situated on a 1-acre lot at the end of Whit Lane! Offering over 2,000 sq ft all on one level, this home features a spacious and functional floor plan with room to spread out both inside and out. The attached garage and double driveway provide plenty of parking and convenience, while the sunroom offers a great bonus space to relax, entertain, or enjoy the view of the property.

  Sarah Stone Wilkes Heritage Homes Real Estate

  1134 Whit Ln, Madisonville, KY 42431
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  /28

  $209,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,164 Sq Ft

  400 Mcleod Ln, Madisonville, KY 42431

  Welcome to 400 Mcleod Lane. This spacious well maintained 3 bedroom Bedford stone home has lots to offer. The interior features a large kitchen with tiled floor and plenty of cabinetry, a sunroom plus a spacious living room with a fireplace along with a family room and additional fireplace. New roof shingles, gutters and vinyl plank flooring in living room, hallway and 2 bedrooms in 2025. Sitting

  Ginger Driver Haven Realty, LLC

  400 Mcleod Ln, Madisonville, KY 42431
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  /46

  $369,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft

  2167 Rose Creek Rd, Madisonville, KY 42431

  New on the market is this truly one-of-a-kind property offering space, versatility, and comfort in every direction. Sitting on a generous 2-acre tract. The property features an impressive 5040 pole barn—ideal for equipment storage, hobby space, or anyone needing substantial workshop capabilities. In addition, there's a 4030 detached garage complete with an office area that can easily double as a

  Charles Lambdin Tradewater Realty

  2167 Rose Creek Rd, Madisonville, KY 42431

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