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Middletown, KY Houses for Sale

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  • /30

    $485,000 Open Sat 10AM - 12PM

    • 4 Beds
    • 3 Baths
    • 3,134 Sq Ft

    729 Dehart Ln, Middletown, KY 40243

    Welcome to 729 Dehart Ln, a beautifully maintained and versatile home nestled in the sought-after Urton Woods community of Middletown. This spacious 2-story property is thoughtfully designed to meet the needs of both growing families and those who love to entertain. Boasting 4 large bedrooms—with the option to easily convert the first-floor flex space into a 5th bedroom—this home provides

    Griffin Hicks RE/MAX Properties East

    729 Dehart Ln, Middletown, KY 40243
  • /48

    $345,678

    • 3 Beds
    • 2 Baths
    • 2,579 Sq Ft

    207 N Madison Ave, Louisville, KY 40243

    Fantastic Cape Cod Cottage in the Heart of Historic MiddletownThis beautifully updated Cape Cod home combines classic curb appeal with modern upgrades, making it the perfect blend of charm and functionality. Located in the desirable and walkable community of historic Middletown, you'll love the tree-lined yard and welcoming presence of this well-maintained property.Step inside to

    Travis Cox 85W Real Estate

    207 N Madison Ave, Louisville, KY 40243
  • /34

    $379,900

    • 3 Beds
    • 2 Baths
    • 2,591 Sq Ft

    12408 Brightfield Dr, Louisville, KY 40243

    Nice brick cape cod in desirable Crosscreeke, super close to all Middletown has to offer. The first floor consists of a living room with fireplace, dining room, kitchen, bedroom, a den (which could easily be turned into a fourth bedroom) and a full bath. The second floor has two bedrooms and a full bath. The finished basement has a family room, game room and laundry. Nice backyard, 2-car attached

    Fred Levein THINK Real Estate LLC

    12408 Brightfield Dr, Louisville, KY 40243
  • /29

    $320,000

    • 3 Beds
    • 2 Baths
    • 1,518 Sq Ft

    12414 Crosswinds Dr, Louisville, KY 40243

    Welcome to 12414 Crosswinds, a well-kept 3-bedroom, 2-bath home in one of Louisville's most sought-after school districts. This move-in ready property combines everyday comfort with an unbeatable location close to shopping, dining, parks, and major highways.Inside, the bright living room features an inviting fireplace and flows easily into the kitchen and dining area. The primary suite

    Jason Switzer 85W Real Estate

    12414 Crosswinds Dr, Louisville, KY 40243
  • /38

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    12006 Old Henry Rd, Louisville, KY 40223

    Rare Renovated Cape Cod in Prime Middletown Location! Beautifully updated 3BR/2BA Cape Cod located just one minute from Shelbyville Road in the heart of Middletown. This charming home features a spacious open-concept kitchen and living area—perfect for modern living and entertaining. The kitchen boasts brand-new stainless steel appliances, updated lighting, and new insulation throughout. Major

    Bob Sokoler RE/MAX Properties East

    12006 Old Henry Rd, Louisville, KY 40223
  • /38

    $310,000

    • 3 Beds
    • 2.5 Baths
    • 1,678 Sq Ft

    12420 Brothers Ave, Louisville, KY 40243

    Welcome to Middletown Villa! This charming two-story, three-bedroom, 2.5-bath home is perfectly situated just minutes from all the shopping, dining, parks, and activities Middletown has to offer. Inside, you'll find fresh paint, updated LVP flooring, and an incredible layout ideal for both daily living and entertaining. The first floor boasts two spacious living rooms, plus a large kitchen and

    Shaun Wallace 1 Percent Lists Purple Door

    12420 Brothers Ave, Louisville, KY 40243
  • /31

    $339,000

    • 3 Beds
    • 2.5 Baths
    • 1,703 Sq Ft

    11713 Robindale Rd, Louisville, KY 40243

    11713 Robindale Ct is Looking for new owners to love on this great property and make it their own. a wonderful 2-story home nestled in the heart of sought-after Middletown! The first floor features a spacious Great Room with hardwood floors and a cozy fireplace—perfect for relaxing or entertaining. The bright Eat-In Kitchen offers white cabinetry, stainless steel appliances, and ample counter and

    Keren Benabou RE/MAX Properties East

    11713 Robindale Rd, Louisville, KY 40243
  • /11

    $549,900

    • 5 Beds
    • 3.5 Baths
    • 3,338 Sq Ft

    569 Wooded Falls Rd, Middletown, KY 40243

    Welcome to one of the largest and most desirable floor plans in Urton Woods - the Hartford II by Ball Homes! This expansive home offers over 3,300 square feet of finished living space on the first and second floors, plus an additional 1,800 square feet in the walkout basement, ready for your custom finish. Located in the heart of Middletown, this beautiful and well-designed home features 5

    Victoria Lyalin Semonin REALTORS

    569 Wooded Falls Rd, Middletown, KY 40243
  • /52

    $595,000

    • 5 Beds
    • 2.5 Baths
    • 3,031 Sq Ft

    12200 Old Henry Rd, Louisville, KY 40223

    This charming property is the perfect blank canvas, ready to transform into the home of your dreams with a little TLC. Situated on just under 3 sprawling acres, this home offers endless possibilities for creating your own private oasis. The thoughtfully designed floor plan features a first-floor primary bedroom with an en-suite bathroom, offering both convenience and privacy. The spacious layout

    Remire Heinze BERKSHIRE HATHAWAY HomeServices, Parks & Weisberg Realtors

    12200 Old Henry Rd, Louisville, KY 40223
  • /33

    $359,000

    • 2 Beds
    • 2 Baths
    • 1,436 Sq Ft

    1107 Belmont Park Way, Louisville, KY 40243

    Discover easy, one-story living in this delightful 2-bedroom, 2-full-bath ranch-style home located in a quiet, convenient neighborhood of Louisville, KY. Perfectly designed for comfort and functionality, this home offers spacious living areas with a welcoming layout ideal for both relaxing and entertaining.Enjoy the ease of a single-level floorplan with two generously sized bedrooms, each

    Autumn Boblitt Torrey Smith Realty Co, LLC

    1107 Belmont Park Way, Louisville, KY 40243
  • /68

    $840,000

    • 5 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    11805 Cedardale Rd, Louisville, KY 40223

    Welcome to this exceptional home in the heart of Anchorage, KY, located in the award-winning Anchorage School District. Nestled on 1.7 private acres, this five-bedroom home blends timeless charm with modern comfort. The first-floor primary suite offers soaring ceilings, a spacious en-suite bath with soaking tub and walk-in shower. The main level features hardwood floors, a sunken living room, and

    Shaun Wallace 1 Percent Lists Purple Door

    11805 Cedardale Rd, Louisville, KY 40223
  • /44

    $385,000

    • 3 Beds
    • 2 Baths
    • 2,221 Sq Ft

    11802 Running Creek Rd, Louisville, KY 40243

    Move in Ready 3 bedroom home in Douglass Hills. 2300 square feet of living space on the 1st floor and the finished basement. (possible bdrm in basement with no egress) Formal dining room and living room with hardwood floors. Kitchen attaches to a den/family room with stone fireplace and bookcases, vaulted ceiling and opens to the back deck. Back yard is fenced and generously landscaped for your

    Pam Lumley RE/MAX Ability Plus

    11802 Running Creek Rd, Louisville, KY 40243
  • /29

    $1

    • 3 Beds
    • 1 Bath
    • 1,625 Sq Ft

    215 S Madison Ave, Louisville, KY 40243

    Property to be sold at Auction by FourSquare Auctions. Internet bidding begins August 21, 2025 at Noon EDT. Bidding ends Thursday Sept 4 at 5:25. Final bids will be both internet and in-person at 11721 Main St, Middletown, KY. .For information and details go to

    Tom Cox RE/MAX Real Estate Champions

    215 S Madison Ave, Louisville, KY 40243

Why Live in Middletown

Middletown, Kentucky, is a historic settlement located approximately 15 miles from Louisville, blending the charm of a small Southern town with modern suburban living. The area features a mix of historic homes and new subdivisions, with architectural styles including ranch, new traditional, Craftsman, and Tudor-style homes. Streets vary from wide sidewalks to narrow, tree-lined roads. Middletown is served by the Jefferson County Public Schools District, with Eastern High School offering highly rated education and specialized academy programs. Residents can enjoy outdoor activities at Wetherby Park, Crosby Park, and Berrytown Park, which feature walking paths, ballfields, tennis courts, and playgrounds. Indoor fitness options are available at THE CAV Fitness. Main Street, known as Historical Midtown, is home to local restaurants like Cottage Café and LouVino, as well as essential shopping at Eastgate Shopping Center and Middletown Peddler’s Mall. The Middletown Chamber of Commerce hosts various community events throughout the year, fostering a strong sense of community spirit. The city is bordered by Interstate 64 and traversed by Shelbyville Road, providing direct routes for easy commutes. Middletown is safer than the national average, making it an attractive option for families seeking a blend of historical charm and modern amenities.

Home Trends in Middletown, KY

Housing Trends

Median Sale Price
$410,450
Median Single Family Sale Price
$508,000
Average Price Per Sq Ft
$162
Number of Homes for Sale
2
Last 12 months Home Sales
2
Months of Supply
12.00
Median List Price
$517,450
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-7%
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