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Simpsonville, KY Homes for Sale

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  • /61

    $2,950,000

    • 4 Beds
    • 5 Baths
    • 7,352 Sq Ft

    486 Chesterfield Way, Simpsonville, KY 40067

    Turning off Chesterfield Way onto the newly sealed blacktop driveway, the pace of life immediately begins to slow. The drive winds through rolling pasture, four-board fencing, and across a picturesque tree-lined stream before arriving at the iron entrance gates. Beyond them, mature trees frame both sides of the lane, creating a beautiful approach that feels like a welcome home every time you

    Agent Photo

    Zach Tipton

    Torrey Smith Realty Co., LLC

    486 Chesterfield Way, Simpsonville, KY 40067
  • /87

    $1,499,900

    $175K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 4,265 Sq Ft

    37 Timberwood Dr, Simpsonville, KY 40067

    Welcome to your own private country retreat in sought-after Simpsonville, Kentucky! Situated on 10 beautifully laid-out acres at the end of a cul-de-sac, this exceptional property offers the perfect blend of comfort, recreation, and functionality. Fully fenced and surrounded by mature trees, you'll enjoy a peaceful setting complete with a pond, pavilion, treehouse, barn, and an impressive newly

    Cheryl Poore Weichert Realtors-H. Barry Smith Co.

    37 Timberwood Dr, Simpsonville, KY 40067
  • /23

    $350,000

    • Land
    • 5.01 Acres
    • $69,860 per Acre

    2 Landspur Ct, Simpsonville, KY 40067

    In the heart of Simpsonville—where rolling landscapes meet refined living—this exceptional 5-acre tract offers the rare opportunity to create your dream estate in one of Shelby County's premier communities. Perfectly positioned off Connor Station Road, with nearly 300 feet of road frontage, the property is framed by mature tree lines and set along a quiet, picturesque street, blending privacy

    Patti Kavanaugh Semonin Realtors

    2 Landspur Ct, Simpsonville, KY 40067
  • /29

    $218,900

    • 2 Beds
    • 1.5 Baths
    • 1,166 Sq Ft

    850 Garden Pointe Dr, Simpsonville, KY 40067

    Per the development plan, this is the largest unit in the complex. Custom built as handicapped accessible but these modifications would benefit anyone- wider hallways and door openings, step-in primary tiled shower with very low barrier, no steps into unit, etc. This rear corner unit means privacy for the fenced patio that many units don't have. One owner since new. You will find a very livable

    Fred Levein THINK Real Estate LLC

    850 Garden Pointe Dr, Simpsonville, KY 40067
  • /59

    $899,900

    $90K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,897 Sq Ft

    1948 Todds Point Rd, Simpsonville, KY 40067

    Welcome to one of Simpsonville's most versatile luxury properties, where beautifully renovated living spaces, exceptional craftsmanship, and a rare 30x60 insulated shop come together on a private, beautifully landscaped homesite. This move-in-ready estate offers over 4,500 finished square feet designed for both everyday comfort and entertaining. The completely renovated kitchen features custom

    Melinda Spencer Move With Me Realty

    1948 Todds Point Rd, Simpsonville, KY 40067
  • /61

    $1,100,000

    • 5 Beds
    • 4.5 Baths
    • 3,832 Sq Ft

    401 Old Stone Dr, Simpsonville, KY 40067

    Welcome home to this exceptional custom property nestled on 7.42 picturesque acres in the lush green countryside of Shelby County. Offering the perfect blend of luxury, comfort, and functionality, this stunning home features 5 spacious bedrooms, 4.5 bathrooms, and room for everyone to spread out. The heart of the home is the beautifully updated kitchen, designed to impress with three ovens, two

    Shelly Gardner Keller Williams Collective

    401 Old Stone Dr, Simpsonville, KY 40067
  • /105

    $999,950

    • 4 Beds
    • 2 Baths
    • 2,625 Sq Ft

    1219 Taylor Wood Rd, Simpsonville, KY 40067

    This 4-bedroom, 2-bath historic farmhouse is situated on 5 scenic acres (with an additional adjoining 5-acre tract available for purchase and possible owner financing) in the heart of Simpsonville and offers a rare combination of residential comfort, equestrian functionality, income potential, and Kentucky character. The property includes two barns, seven fenced paddocks, a pond, a detached

    Trish Segrest Segrest Flaherty Realtors LLC

    1219 Taylor Wood Rd, Simpsonville, KY 40067
  • /26

    $174,900

    • 2 Beds
    • 1.5 Baths
    • 902 Sq Ft

    799 Garden Pointe Dr, Simpsonville, KY 40067

    Come check out this cute 2 Bedroom/1 Full and 1 Half Bath Condo in The Gardens of Station Pointe. Home consists of a Living Room, Eat-in Kitchen, 1 Full Bath and 1 Half Bath/Laundry Room Combo. Nice privacy fenced patio off the Kitchen for your outdoor enjoyment. Stop by today before this one is SOLD!

    Sherry Bennett-Webb Bennett-Webb Realty

    799 Garden Pointe Dr, Simpsonville, KY 40067
  • /125

    $1,650,000

    • 5 Beds
    • 6 Baths
    • 7,141 Sq Ft

    107 My Kentucky Rose Cir, Simpsonville, KY 40067

    A rare offering to own this spectacular country estate in the gated community of Majestic Oaks, featuring over 7,000 square feet of living space on 5 verdant acres. The first floor has soaring 10 foot and vaulted ceilings, 3 fireplaces, 2 staircases, and extensive custom woodwork and built-ins. The first floor primary suite is the epitome of luxury, with a steam shower, quartz counters, towel

    Julie Pogue Julie Pogue Properties

    107 My Kentucky Rose Cir, Simpsonville, KY 40067
  • /31

    $267,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    210 Montclair School Rd, Simpsonville, KY 40067

    Welcome home to this beautifully updated 3-bedroom, 2-bath property situated on just over half an acre in Simpsonville, Kentucky. The refreshed kitchen and interior create a warm, move-in-ready atmosphere, while major recent improvements include a brand-new roof, brand-new water heater, and an oversized new deck that's perfect for entertaining, grilling, or relaxing outdoors. With generous yard

    Zach Carnahan 3C Property Management LLC

    210 Montclair School Rd, Simpsonville, KY 40067
  • /58

    $1,699,000

    $26K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 4,731 Sq Ft

    2259 Taylor Wood Rd, Simpsonville, KY 40067

    Welcome to 2259 Taylor Wood Road in Simpsonville, Kentucky. This stunning custom home sits on 6 private acres with no HOA, offering the perfect blend of luxury, privacy, and space in the heart of Shelby County. Built in 2023, this home features 4,731 square feet above grade with 5 bedrooms, a bonus room, 3 full bathrooms and 2 half baths. From the moment you step inside you will notice the

    Sam Stone Lenihan Sotheby's Int'l Realty

    2259 Taylor Wood Rd, Simpsonville, KY 40067
  • /66

    $875,000

    $75K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,250 Sq Ft

    451 Todd Dr, Simpsonville, KY 40067

    *NEW PRICE* Welcome to a truly extraordinary estate in Simpsonville, KY where luxury, space, and timeless elegance come together on more than 5 breathtaking acres. From the moment you arrive, the grand scale and stunning curb appeal make an unforgettable impression. This custom home was designed for those who appreciate refined living, exceptional entertaining spaces, and the flexibility for

    Rhonda Roberts Keller Williams Collective

    451 Todd Dr, Simpsonville, KY 40067
  • /20

    $189,000

    $10K PRICE DROP
    • Land
    • 5.33 Acres
    • $35,460 per Acre

    Tract 1 Hunters Ln, Simpsonville, KY 40067

    Imagine waking up to wide-open skies and quiet countryside on your own 5.33 acres in Shelby County. This gorgeous vacant land is the perfect setting to build your dream home, with plenty of space for outdoor living, gardens, and privacy. Surrounded by natural beauty and peaceful landscape, it's a rare opportunity to create the lifestyle you've always wanted, just the way you want it. Schedule

    Jenna Tracy Schuler Bauer Real Estate Services ERA Powered

    Tract 1 Hunters Ln, Simpsonville, KY 40067
  • /32

    $235,000

    $15K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,176 Sq Ft

    3936 Aiken Rd, Simpsonville, KY 40067

    Recently updated Cozy Cottage in the heart of horse country. Situated across from rolling pastures this two bedroom home is ready for its new owner to make memories as fond as the ones of the past family. Step inside to a large entry room which could double as office, reading nook, or dining space that flows into the living room. An updated kitchen invites you in with a large center island that

    Aaron Marsee EXP Realty LLC

    3936 Aiken Rd, Simpsonville, KY 40067
  • /87

    $649,900

    $50K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,925 Sq Ft

    209 Champions Way, Simpsonville, KY 40067

    Priced UNDER Fair Market Value AND Move-In Ready! Ideally located between Louisville and Lexington, Simpsonville combines small-town charm with convenient access to shopping, dining, and I-64. Nestled in the heart of Kentucky's renowned horse country, you'll enjoy scenic rolling landscapes, beautiful horse farms, and a peaceful setting just minutes from modern conveniences. Situated in the highly

    Margo Whisman Weichert Realtors-H. Barry Smith Co.

    209 Champions Way, Simpsonville, KY 40067
  • /50

    $1,900,000

    • 4 Beds
    • 3.5 Baths
    • 7,224 Sq Ft

    22 Timberwood Dr, Simpsonville, KY 40067

    Exceptional opportunity in desirable Timberwood Farms. Situated on approx. 10 acres, this impressive property offers space, privacy, and a prime Simpsonville location with convenient access to I-64, Shelbyville, and Louisville.

    KRISTY GOOCH RE/MAX Elite Realty

    22 Timberwood Dr, Simpsonville, KY 40067
  • /24

    $325,000

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    310 E Main St, Simpsonville, KY 40067

    Built in 2022 in the heart of Simpsonville, this beautifully designed home sits on a quiet street with a wooded lot that offers both privacy and charm. This home is currently used as a furnished short term rental but would also be a great full time residence! Step inside to a completely open first floor where the living room, dining area, and kitchen flow seamlessly together - perfect for

    Ic Lenihan Sotheby's Int'l Realty

    310 E Main St, Simpsonville, KY 40067
  • /8

    $180,000

    • Land
    • 5.57 Acres
    • $32,316 per Acre

    - Lemaster Ln, Simpsonville, KY 40067

    Over 5.5 acre lot is in the center of horse country!!!! Located just minutes from Jefferson County and it's perfectly located to give you a short drives to town and shopping along with the privacy you may want for home. This Lot is Partially wooded off of Fisherville Rd to Lemaster Ln which is a dead end road. Absolutely No traffic!

    Tasha Wright Diamond Key REALTORS

    - Lemaster Ln, Simpsonville, KY 40067
  • /61

    $749,000

    • 4 Beds
    • 3.5 Baths
    • 3,177 Sq Ft

    1051 Champions Cir, Simpsonville, KY 40067

    The rolling hills and sweet community of Simpsonville welcome you to this STUNNING home in the beautiful Cardinal Club Estates. A quick commute out of the busy-ness of Louisville leads you to the beautiful setting where your next home awaits. Built in 2014 (with 2x6 exterior wall construction) , this home features the updated convenience of an incorporated large kitchen and gathering/family room,

    Jennifer Toadvine Keller Williams Collective

    1051 Champions Cir, Simpsonville, KY 40067
  • /39

    $5,439,000

    • 4 Beds
    • 1.5 Baths
    • 1,966 Sq Ft

    4260 Fisherville Rd, Simpsonville, KY 40067

    Located just minutes away from Simpsonville and the Jefferson Co. line, this beautiful pristine farm offers all the amenities of country living along with the convenience of urban benefits. With almost 156 acres of rolling ground, there are limitless opportunities. The historic farm home features 4 BRs and 1.5 baths with almost all original hardwood flooring throughout. Spend the mornings and

    Steve Hornback Weichert Realtors-H. Barry Smith Co.

    4260 Fisherville Rd, Simpsonville, KY 40067
  • /7

    $1,260,000

    • Land
    • 25 Acres
    • $50,400 per Acre

    4317 Aiken Rd, Simpsonville, KY 40067

    Rarely does a parcel of this caliber become available for sale. Aiken Run is located on Aiken Road in Todd's Point and encompasses 25 breathtaking acres of some of Kentucky's finest horse country. Offering generous road frontage while maintaining exceptional privacy, the property features sweeping views of the surrounding countryside, a neighboring lake and an idyllic setting for building your

    Ic Lenihan Sotheby's Int'l Realty

    4317 Aiken Rd, Simpsonville, KY 40067
  • /29

    $230,000

    • 2 Beds
    • 1.5 Baths
    • 1,165 Sq Ft

    828 Garden Pointe Dr, Simpsonville, KY 40067

    Seller offering a $2000 Credit towards Buyers closing and or prepaid!!! Welcome home to this beautifully maintained patio home in the sought-after Gardens of Station Pointe community. Featuring a spacious family room with a cozy fireplace, a separate private living room, and you own private patio retreat. This home offers a lifestyle that's both comfortable and refined. Abundant storage

    Darlene Jones Abbot Realty & Auction

    828 Garden Pointe Dr, Simpsonville, KY 40067
  • /22

    $210,000

    $9K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,054 Sq Ft

    816 Garden Pointe Dr, Simpsonville, KY 40067

    Nice 2 bedroom condo conveniently located in the desirable town of Simpsonville. This condo features 2 bedrooms, Family room with tray ceiling, eat-in Kitchen, laundry room and 1.5 baths. The buyer of this condo unit can enjoy time outside on the covered front porch or the private back yard.

    Pam Wininger Coldwell Banker Larry Rogers

    816 Garden Pointe Dr, Simpsonville, KY 40067
  • /11

    $489,900

    • 4 Beds
    • 2.5 Baths
    • 1,990 Sq Ft

    1204 Divot Way, Simpsonville, KY 40067

    Welcome to this exceptional 4 BEDROOM + 2 1/2 BATH NEW CONSTRUCTION home in the highly sought-after Villas at Cardinal Club. Offering 1,990 square feet of thoughtfully designed living space, this home delivers the perfect balance of style, comfort, and functionality. This home features a spacious first-floor primary suite, providing privacy and convenience, while three additional bedrooms

    Melinda Mathis Watts Torrey Smith Realty Co., LLC

    1204 Divot Way, Simpsonville, KY 40067
  • /67

    $14,000,000

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

    10053 Shelbyville Rd, Simpsonville, KY 40067

    A landmark Kentucky estate of extraordinary provenance, 10053 Shelbyville Road offers approximately 55 acres along one of the region's most coveted corridors near the Jefferson/Shelby County line. Built in the early 1800s, near the formation of the Commonwealth, the historic main residence is listed on the historic registry and is believed to be among the oldest homes in Kentucky, with the

    Bowin Tichenor Fathom Realty Ky LLC

    10053 Shelbyville Rd, Simpsonville, KY 40067

Why Live in Simpsonville

Simpsonville, KY, is a growing community situated between Louisville and Frankfort, known for its blend of rural and suburban living. The area is characterized by rolling Bluegrass hills and numerous equestrian facilities. Residential options range from newer subdivisions with Cape Cod and ranch-style homes to luxury properties in the Cardinal Club golf course community. Many homes feature spacious lots, with some properties spanning over five acres, catering to those seeking more space and horse-friendly environments. The local real estate market includes single-family homes, cottages, custom estates, condos, and townhouses, with prices varying based on property size and features.

Simpsonville offers a variety of local attractions and amenities. The central commercial district on Shelbyville Road includes unique dining options like Dos Mundos, a Peruvian and Asian fusion restaurant, and local businesses such as Weathered Oak Farms bakery and Brick and Mortar Boutique and Coffeehouse. The Outlet Shoppes of the Bluegrass provide access to national brands, while the Shelby County Flea Market features numerous vendors on weekends. For outdoor activities, Fred Wiche Park hosts farmers markets and a fall festival, while Simpsonville Park offers sports fields and a playground. The University of Louisville Golf Club provides golf, swimming, and clubhouse amenities.

Educational opportunities in Simpsonville include Simpsonville Elementary, which is highly rated within the Shelby County Public Schools district. The city is conveniently connected to major cities via Interstate 64, with both Louisville and Frankfort approximately 30 miles away. The proximity to Louisville Muhammad Ali International Airport ensures easy access to domestic flights.

Frequently Asked Questions

What is the average home price in Simpsonville, KY?
Homes for sale in Simpsonville, KY have an average home price of $494,331.
Are home prices dropping in Simpsonville?
Yes, home prices in Simpsonville are down 15% in the last 12 months.
How many homes have sold over the last 12 months in Simpsonville, KY?
63 homes have sold in Simpsonville, KY over the last 12 months.
What is the average household income in Simpsonville, KY?
The average household income in Simpsonville, KY is $108K.
What are the most popular zip codes in Simpsonville, KY?
The most popular zip codes in Simpsonville, KY include 40067, 40065, 40023, 40245 and 40022.
How much do you need to make to afford a house in Simpsonville?
The median home price in Simpsonville is $384,500. If you put a 20% down payment of $76,900 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $1,980 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $85K a year to afford the median home price in Simpsonville. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Simpsonville is $108K.
How are the schools in Simpsonville, KY?
Simpsonville, KY has highly rated public and private schools. Some of the best schools in Simpsonville based on Niche Grades are Simpsonville Elementary School, Martha Layne Collins High School and Shelby County West Middle School. Browse all the schools in Simpsonville, KY to learn more.

Home Price Trends

Median Sale Price
$372,500
Median Single Family Sale Price
$393,450
Median 2 Bedroom Sale Price
$219,450
Average Price Per Sq Ft
$198
Number of Homes for Sale
12
Last 12 months Home Sales
63
Months of Supply
2.30
Median List Price
$384,500
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
3%
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