16,203

Winchester, KY Homes

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  • /2

    $14,100,000

    • Land
    • 274.52 Acres
    • $51,362 per Acre

    2395 Paris Rd, Winchester, KY 40391

    Welcome to Deerlawn, Winchester's newest approved residential development and a major new-construction opportunity in Clark County. Located at 2395 Paris Road, Deerlawn is a 274-acre master-planned community designed to deliver 438 single-family homes, along with additional duplex and townhome opportunities, creating long-term scale for builders and more choices for buyers looking to build in

    Agent Photo

    Melia Hord

    MELIA Realty LLC

    2395 Paris Rd, Winchester, KY 40391
  • /10

    $1,045 Per Month

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Condo for Rent

    163-165 Westside Dr Unit 163 Westside Dr, Winchester, KY 40391

    Very centrally located 2 bedroom 2 bath apartment! Easy interstate access! 2 full baths! Cats/Dogs welcome!!!

    163-165 Westside Dr Unit 163 Westside Dr, Winchester, KY 40391
  • /85

    $1,370,000

    Sold Sep 09, 2026

    1200 Craig Crossing, Winchester, KY 40391

    • 4 Beds
    • 4.5 Baths
    • 3,350 Sq Ft
    • Built 2026

    Last Sold Summary

    • 2% Above List Price
    • $409/SF
    • 49 Days On Market

    Last Listing Agent Michael Hilario The Agency

    1200 Craig Crossing, Winchester, KY 40391
    • /39

      Est $401,610

      Not Listed For Sale

      900 Vienna Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 2,314 Sq Ft
      • Built 2005
      900 Vienna Rd, Winchester, KY 40391

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Devin Ramsey Berkshire Hathaway HomeServices Foster Realtors

  • /2

    $78,500

    • Land
    • 15,246 Sq Ft
    • $224,286 per Acre

    2395 Paris Rd Unit Lot 2, Winchester, KY 40391

    Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

    Agent Photo

    Melia Hord

    MELIA Realty LLC

    2395 Paris Rd Unit Lot 2, Winchester, KY 40391
  • /2

    $1,650 Per Month

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    135 Winn Ave Unit A, Winchester, KY 40391

    Welcome to this beautifully renovated 3-bedroom, 2-bathroom home, offering the perfect combination of modern style and everyday comfort. The bright and spacious living area flows seamlessly into a stylish, updated kitchen, creating an inviting space for relaxing or entertaining. Thoughtfully designed with contemporary finishes and a functional layout, this move-in-ready home is ideal for

    135 Winn Ave Unit A, Winchester, KY 40391
  • /8

    $160,000

    Sold Jul 13, 2026

    107 Patio St, Winchester, KY 40391

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1997

    Last Sold Summary

    • $185/SF
    • 0 Days On Market

    Current Estimated Value $161,771

    Last Listing Agent Sherry Stephens Murphy Realty Group

    107 Patio St, Winchester, KY 40391
    • /23

      Est $825,101

      Not Listed For Sale

      1275 Old Log Lick Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1982
      1275 Old Log Lick Rd, Winchester, KY 40391

      Last Sold Summary

      • 474 Days On Market

      Last Listing Agent John Wilson Bluegrass Properties Group

  • /23

    $249,500

    • Land
    • 14.51 Acres
    • $17,194 per Acre

    3056 Irvine Rd, Winchester, KY 40391

    Discover the perfect blend of beauty, privacy, and opportunity with this stunning 14.511-acre tract on Irvine Road. Featuring gently rolling hills, this property offers multiple ideal building sites to bring your dream home to life, whether you're envisioning a modern farmhouse, barndominium, or private country retreat. A barn is already in place, adding immediate functionality for storage,

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    3056 Irvine Rd, Winchester, KY 40391
  • /7

    $924 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    106 Alabama St Unit 3, Winchester, KY 40391

    Available September 8,2026! – Recently Renovated Winchester Apartment!Welcome to your next home in the heart of Winchester! This beautifully updated 1-bedroom, 1-bath apartment is nestled just off Lexington Avenue and Bypass Road close to shopping, dining, and just minutes from downtown Winchester.At Bluegrass Rental Management, we strive to provide an experience that is

    106 Alabama St Unit 3, Winchester, KY 40391
  • /38

    $484,900

    Sold Aug 13, 2026

    414 Fairholme Way, Winchester, KY 40391

    • 4 Beds
    • 3 Baths
    • 2,418 Sq Ft
    • Built 2025

    Last Sold Summary

    • $201/SF
    • 53 Days On Market

    Current Estimated Value $474,841

    Last Listing Agent Morgan Withrow The Brokerage

    414 Fairholme Way, Winchester, KY 40391
    • /44

      Est $312,946

      Not Listed For Sale

      2482 Mina Station Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft
      • Built 1962
      2482 Mina Station Rd, Winchester, KY 40391

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  • /2

    $78,500

    • Land
    • 13,982 Sq Ft
    • $244,548 per Acre

    2395 Paris Rd Unit LOT 7, Winchester, KY 40391

    Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

    Agent Photo

    Melia Hord

    MELIA Realty LLC

    2395 Paris Rd Unit LOT 7, Winchester, KY 40391
  • /25

    $223,000

    Sold Nov 04, 2025

    204 Crawford Ct, Winchester, KY 40391

    • 4 Beds
    • 2 Baths
    • 1,636 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $136/SF
    • 1 Day On Market

    Current Estimated Value $229,223

    Last Listing Agent Tisha Monte Bluegrass Properties Group

    204 Crawford Ct, Winchester, KY 40391
    • /43

      Est $287,801

      Not Listed For Sale

      2270 Mina Station Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,358 Sq Ft
      • Built 1971
      2270 Mina Station Rd, Winchester, KY 40391

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  • /41

    $343,900

    New Construction
    • 3 - 5 Beds
    • 2 - 4 Baths
    • 1,424 Sq Ft

    Lucy Plan at Boone's Crossing, Winchester, KY 40391

    Experience the Lucy floor plan, a versatile and thoughtfully designed new construction home that gives every member of the family the space they need to live, work, and thrive. Built by one of the most trusted home builders in Central Kentucky, the Lucy is a top choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want flexibility, comfort, and

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824256, Winchester, KY 40391
  • /26

    $274,900

    Sold Aug 25, 2026

    136 Sturbridge Ln, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 1,604 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Below List Price
    • $171/SF
    • 21 Days On Market

    Current Estimated Value $279,661

    Last Listing Agent Sarah MacHarg Kentucky Land and Home

    136 Sturbridge Ln, Winchester, KY 40391
    • /70

      Est $597,936

      Not Listed For Sale

      519 Right Angle Rd, Winchester, KY 40391

      • 6 Beds
      • 3 Baths
      • 3,712 Sq Ft
      • Built 2000
      519 Right Angle Rd, Winchester, KY 40391

      Last Sold Summary

      • 186 Days On Market

      Last Listing Agent The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  • /37

    $378,900

    New Construction
    • 3 - 5 Beds
    • 2.5 - 3.5 Baths
    • 2,098 Sq Ft

    Nancy Plan at Boone's Crossing, Winchester, KY 40391

    Experience the Nancy floor plan, a masterfully designed two-story new construction home that blends smart functionality with open-concept living. Built by one of the most trusted home builders in Central Kentucky, the Nancy is an ideal choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want style, flexibility, and efficient use of space.From the

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824252, Winchester, KY 40391
  • /16

    $165,000

    Sold Apr 30, 2026

    47 Buckner St, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,635 Sq Ft
    • Built 1930

    Last Sold Summary

    • 8% Below List Price
    • $101/SF
    • 24 Days On Market

    Current Estimated Value $171,741

    Last Listing Agent Michael Hilario The Agency

    47 Buckner St, Winchester, KY 40391
    • /69

      Est $378,525

      Not Listed For Sale

      3975 Wills Rupard Rd, Winchester, KY 40391

      • 4 Beds
      • 3 Baths
      • 3,021 Sq Ft
      • Built 1986
      3975 Wills Rupard Rd, Winchester, KY 40391

      Last Sold Summary

      • 218 Days On Market

      Last Listing Agent Tonya Morrow KY Local

  • /45

    $429,900

    New Construction
    • 3 - 5 Beds
    • 2.5 - 4.5 Baths
    • 2,722 Sq Ft

    Eleanor Plan at Boone's Crossing, Winchester, KY 40391

    Experience elevated living with the Eleanor floor plan, a thoughtfully designed new construction home available through one of the most trusted home builders in Central Kentucky. Created for today’s buyers seeking flexibility, luxury, and energy efficiency, the Eleanor blends timeless design with modern functionality for families looking for new construction homes in Lexington KY and surrounding

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824255, Winchester, KY 40391
  • /74

    $320,000

    Sold Sep 10, 2026

    13 Bel Air Dr, Winchester, KY 40391

    • 3 Beds
    • 3 Baths
    • 2,068 Sq Ft
    • Built 1962

    Last Sold Summary

    • 6% Below List Price
    • $155/SF
    • 36 Days On Market

    Current Estimated Value $333,822

    Last Listing Agent Robin Jones Keller Williams Legacy Group

    13 Bel Air Dr, Winchester, KY 40391
    • /61

      Est $470,369

      Not Listed For Sale

      2601 Crowe Ridge Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 2,435 Sq Ft
      • Built 2002
      2601 Crowe Ridge Rd, Winchester, KY 40391

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Morton Trimble HomeFirst Real Estate

  • /35

    $360,900

    New Construction
    • 3 - 4 Beds
    • 2.5 - 3.5 Baths
    • 1,828 Sq Ft

    Grace Plan at Boone's Crossing, Winchester, KY 40391

    Discover the Grace floor plan, a thoughtfully designed new construction home that blends open-concept living with private, comfortable bedroom spaces. Built by one of the leading home builders in Central Kentucky, the Grace is a perfect fit for buyers searching for new construction homes in Lexington KY and nearby communities who want flexibility, style, and energy efficiency.From the moment you

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824257, Winchester, KY 40391
  • /56

    $320,000

    Sold Jun 03, 2026

    215 Old Log Lick Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 2002

    Last Sold Summary

    • 9% Below List Price
    • $221/SF
    • 53 Days On Market

    Current Estimated Value $317,779

    Last Listing Agent Kerry Ball Local First Realty, LLC

    215 Old Log Lick Rd, Winchester, KY 40391
    • /56

      Est $725,871

      Not Listed For Sale

      9953 Ironworks Rd, Winchester, KY 40391

      • 6 Beds
      • 2.5 Baths
      • 3,800 Sq Ft
      • Built 2003
      9953 Ironworks Rd, Winchester, KY 40391

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Tara Smith Keller Williams Commonwealth

  • /46

    $347,900

    New Construction
    • 3 - 6 Beds
    • 2 - 4 Baths
    • 1,580 Sq Ft

    Martha Plan at Boone's Crossing, Winchester, KY 40391

    The Martha floor plan is your canvas for creating a home that perfectly fits your lifestyle, offering unmatched flexibility, thoughtful design, and timeless appeal. Built by one of the leading home builders in Central Kentucky, the Martha is an excellent choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space that adapts to how they

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824258, Winchester, KY 40391
  • /94

    $759,000

    Sold Jun 17, 2026

    4040 Muddy Creek Rd, Winchester, KY 40391

    • 4 Beds
    • 3.5 Baths
    • 4,584 Sq Ft
    • Built 2007

    Last Sold Summary

    • 15% Below List Price
    • $166/SF
    • 262 Days On Market

    Current Estimated Value $767,253

    Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

    4040 Muddy Creek Rd, Winchester, KY 40391
    • /17

      Est $454,075

      Not Listed For Sale

      1026 Crowe Ridge Rd, Winchester, KY 40391

      • 1 Bath
      • Built 1945
      1026 Crowe Ridge Rd, Winchester, KY 40391

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Sophia Herald Herald Real Estate

  • /28

    $363,900

    New Construction
    • 4 - 5 Beds
    • 2.5 - 3.5 Baths
    • 2,100 Sq Ft

    Elizabeth Plan at Boone's Crossing, Winchester, KY 40391

    Experience the Elizabeth floor plan, a beautifully crafted new construction home designed for families who value open-concept living, thoughtful organization, and flexible bedroom space. Offered by one of the most trusted home builders in Central Kentucky, the Elizabeth is a standout option for buyers searching for new construction homes in Lexington KY and surrounding communities.From the moment

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824250, Winchester, KY 40391
  • /20

    $217,500

    Sold May 22, 2026

    7 Hiawatha Trail, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,190 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Below List Price
    • $183/SF
    • 10 Days On Market

    Current Estimated Value $220,844

    Last Listing Agent Serena Cassidy Coldwell Banker McMahan

    7 Hiawatha Trail, Winchester, KY 40391
    • /39

      Est $491,999

      Not Listed For Sale

      600 Ferry Rd, Winchester, KY 40391

      • 3 Beds
      • 2.5 Baths
      • 2,076 Sq Ft
      • Built 2003
      600 Ferry Rd, Winchester, KY 40391

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  • /85

    $397,900

    New Construction
    • 3 - 5 Beds
    • 2.5 - 4.5 Baths
    • 2,263 Sq Ft

    Abigail Plan at Boone's Crossing, Winchester, KY 40391

    Step into the award-winning Abigail floor plan, a standout choice for buyers searching for new construction homes in Lexington, KY and Central Kentucky. Designed with today’s lifestyle in mind, this home offers the perfect blend of flexible floor plans, energy efficiency, and modern comfort—everything you expect from a trusted home builder in Lexington, KY.From the moment you arrive, the Abigail

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824251, Winchester, KY 40391
  • /39

    $340,000

    Sold Oct 10, 2025

    219 Hampton Ave, Winchester, KY 40391

    • 4 Beds
    • 2.5 Baths
    • 2,929 Sq Ft
    • Built 1972

    Last Sold Summary

    • 7% Below List Price
    • $116/SF
    • 48 Days On Market

    Current Estimated Value $345,254

    Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

    219 Hampton Ave, Winchester, KY 40391
    • /40

      Est $350,885

      Not Listed For Sale

      13544 Irvine Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,988 Sq Ft
      • Built 1969
      13544 Irvine Rd, Winchester, KY 40391

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Susan Baldwin Threshold Real Estate Services

  • /52

    $369,900

    New Construction
    • 3 - 6 Beds
    • 2 Baths
    • 1,770 Sq Ft

    Barbara Plan at Boone's Crossing, Winchester, KY 40391

    Experience the true essence of homecoming with the Barbara floor plan, a beautifully designed new construction home available through one of the most trusted home builders in Central Kentucky. Thoughtfully crafted for modern living, this plan blends timeless exterior charm with a warm, open interior designed for comfort, flexibility, and everyday functionality.Step onto the inviting covered front

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824253, Winchester, KY 40391
  • /28

    $83,000

    Sold May 08, 2026

    32 Hays St, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • Built 1950

    Last Sold Summary

    • 8% Below List Price
    • $54/SF
    • 5 Days On Market

    Current Estimated Value $93,237

    Last Listing Agent Christa Joynt Keller Williams Commonwealth

    32 Hays St, Winchester, KY 40391
    • /26

      Est $322,566

      Not Listed For Sale

      11705 Irvine Rd, Winchester, KY 40391

      • 3 Beds
      • 1.5 Baths
      • 2,668 Sq Ft
      • Built 1988
      11705 Irvine Rd, Winchester, KY 40391

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Matthew J. Reffett Re/Max Legacy Group - Paintsville

  • /127

    $3,450,000

    • 2 Beds
    • 2.5 Baths
    • 2,725 Sq Ft

    510 - 612 Quisenberry Ln, Winchester, KY 40391

    Adjoining the banks of the Lower Howard's Creek in Clark County lies a very special 145.6± acre farm. With some of the oldest settlements in the county, this region near the Old Stone Church (or Old Providence Church) is immensely historic. Daniel Boone's first eleven surveys in Kentucky were conducted for the Bush family, early inhabitants of the area and farm. With gated stone entrances and

    Zach Davis Kirkpatrick & Company

    510 - 612 Quisenberry Ln, Winchester, KY 40391

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