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Simpsonville, KY Homes for Sale | Realty.com
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3 bedsNew constructionWith a pool
19 listings
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Homes for Sale in Simpsonville, KY

Homes for Sale in Simpsonville, KY

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19 Listings
Map

Homes for Sale in Simpsonville, KY

19 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas
  1. 60 Lizas Cir — photo84Active

    $1,590,000

    5 bd · 5 ba · 5,821 sqft

    60 Lizas Cir, Simpsonville, KY

    Lauren Arnwine · Covenant Realty LLC

  2. 107 My Kentucky Rose Cir — photo124Active

    $1,550,000

    5 bd · 6 ba · 7,141 sqft

    107 My Kentucky Rose Cir, Simpsonville, KY

    Julie W Pogue · Julie Pogue Properties

  3. 220 Rolling Ridge Way — photo48Active

    $340,000

    3 bd · 3 ba · 1,836 sqft

    220 Rolling Ridge Way, Simpsonville, KY

    Rebecca Smith · United Real Estate Louisville

  4. 2259 Taylor Wood Rd — photo57Active

    $1,699,000

    5 bd · 5 ba · 4,731 sqft

    2259 Taylor Wood Rd, Simpsonville, KY

    Sam Stone · Lenihan Sotheby's Int'l Realty

  5. 268 Lang Run Ct — photoPrice Reduced44Active

    $360,000

    4 bd · 3 ba · 2,560 sqft

    268 Lang Run Ct, Simpsonville, KY

    Larry W Baker · Realty Advanced

  6. 210 Montclair School Rd — photoPrice Reduced31Active

    $259,900

    3 bd · 2 ba · 1,200 sqft

    210 Montclair School Rd, Simpsonville, KY

    Zackery D Carnahan · 3C Property Management LLC

  7. 486 Chesterfield Way — photo61Active

    $2,950,000

    4 bd · 5 ba · 7,352 sqft

    486 Chesterfield Way, Simpsonville, KY

    Zachary Tipton · Torrey Smith Realty Co., LLC

  8. 799 Garden Pointe Dr — photoPrice Reduced26Active

    $164,900

    2 bd · 2 ba · 902 sqft

    799 Garden Pointe Dr, Simpsonville, KY

    Sherry L Bennett-Webb · Bennett-Webb Realty

  9. 1219 Taylor Wood Rd — photoPrice Reduced105Active

    $985,000

    4 bd · 2 ba · 2,625 sqft

    1219 Taylor Wood Rd, Simpsonville, KY

    Trish Segrest · Segrest Flaherty Realtors LLC

  10. 3936 Aiken Rd — photoPrice Reduced32Active

    $228,500

    2 bd · 1 ba · 1,176 sqft

    3936 Aiken Rd, Simpsonville, KY

    Aaron Marsee · EXP Realty LLC

  11. 1204 Divot Way — photoPrice Reduced43Active

    $459,900

    4 bd · 3 ba · 1,990 sqft

    1204 Divot Way, Simpsonville, KY

    Melinda Mathis Watts · Torrey Smith Realty Co., LLC

  12. 37 Timberwood Dr — photoPrice Reduced87Active

    $1,450,000

    3 bd · 3 ba · 4,265 sqft

    37 Timberwood Dr, Simpsonville, KY

    Cheryl Poore · Weichert Realtors-H. Barry Smith Co.

  13. 850 Garden Pointe Dr — photo29Active

    $218,900

    2 bd · 2 ba · 1,166 sqft

    850 Garden Pointe Dr, Simpsonville, KY

    Fred Levein · THINK Real Estate LLC

  14. 816 Garden Pointe Dr — photoPrice Reduced22Active

    $210,000

    2 bd · 2 ba · 1,054 sqft

    816 Garden Pointe Dr, Simpsonville, KY

    Pam H Carter · Coldwell Banker Larry Rogers

  15. 10053 Shelbyville Rd — photo67Active

    $14,000,000

    7 bd · 3 ba · 5,338 sqft

    10053 Shelbyville Rd, Simpsonville, KY

    Bowin Tichenor · Fathom Realty Ky LLC

  16. 310 E Main St — photo24Active

    $325,000

    3 bd · 3 ba · 1,320 sqft

    310 E Main St, Simpsonville, KY

    Beam | Feather | Hurley · Lenihan Sotheby's Int'l Realty

  17. 22 Timberwood Drive — photo50Active

    $1,900,000

    4 bd · 4 ba · 7,224 sqft

    22 Timberwood Drive, Simpsonville, KY

    Kristy L Gooch · RE/MAX Elite Realty

  18. 401 Old Stone Dr — photo61Active

    $1,100,000

    5 bd · 5 ba · 3,832 sqft

    401 Old Stone Dr, Simpsonville, KY

    Shelly H Gardner · Keller Williams Collective

  19. 828 Garden Pointe Dr — photo29Active

    $230,000

    2 bd · 2 ba · 1,165 sqft

    828 Garden Pointe Dr, Simpsonville, KY

    Darlene Jones · Abbot Realty & Auction

Explore Simpsonville homes

By price

  • Under $300K
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  • Under $700K
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  • 2 beds
  • 3 beds
  • 4 beds
  • 5 beds

By type

  • Single family
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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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Listing data & MLS disclosures

Imagine MLS (Bluegrass REALTORS)
The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by IDX brokerage firms other than Realty.com, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this web site comes in part from the IDX Program of GLAR\Metro Search,Inc. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Information is deemed reliable but not guaranteed, .
Listing information ©2026 Greater Louisville AOR® and Metro Search, Inc. All Rights Reserved. Last Updated: 2026-09-06 02:17:25 UTC
  • By feature

    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #221881

    Call Thomas

    Simpsonville, KY community profile

    Population
    3,173
    Median income
    $91,706
    Housing units
    1,253
    People per sq. mi.
    67.7
    Area
    46.9 sq. mi.

    Source: HJN community data

    Simpsonville housing market

    August 2026 · This period is still settling

    Selling at 98.8% of asking price

    Buyers here are paying below asking. MLS · 10 sales · as of Aug 21, 2026

    Homes on the market · MLS, as of Aug 30, 2026

    Median list price
    $479,900
    Homes for sale
    19

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,854 sq. ft.

    Nearby areas

    ZIP codes

    • 40291 (137)
    • 40059 (126)
    • 40229 (121)
    • 40245 (120)
    • 40047 (119)
    • 40299 (116)
    • 40165 (115)
    • 40065 (109)

    Cities

    • Louisville (1,307)
    • Prospect (124)
    • Mt Washington (119)
    • Shepherdsville (115)
    • Shelbyville (109)
    • La Grange (64)
    • Taylorsville (56)
    • Crestwood (52)