15,923

Winchester, KY Homes

Section Image
  • /2

    $110,000

    • Land
    • 0.32 Acre
    • $343,750 per Acre

    115 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    115 Jacob Ct, Winchester, KY 40391
  • /2

    $180,000 Sold Jul 01, 2025

    • 2,250 Sq Ft
    • $80/SF
    • 4 Beds
    • 4 Baths
    • Built 1953

    23 Meadowbrook Dr, Winchester, KY 40391

    Location, Location, Location! Property sold as is.

    A. Rebecca Woods Woods Realty Group

    23 Meadowbrook Dr, Winchester, KY 40391
    • /53

      Est $489,020 Not Listed For Sale

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

      148 Teal Ln, Winchester, KY 40391

      148 Teal Ln, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.27 Acre
    • $407,407 per Acre

    125 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    125 Jacob Ct, Winchester, KY 40391
  • /2

    $286,000 Sold Jun 12, 2025

    • 2,394 Sq Ft
    • $119/SF
    • 0 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1998

    209 Locust Grove Rd, Winchester, KY 40391

    For comp purposes

    Lindsay Barsotti ERA Select Real Estate

    209 Locust Grove Rd, Winchester, KY 40391
    • /21

      Est $255,142 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,266 Sq Ft

      445 Chaucer Ct, Winchester, KY 40391

      445 Chaucer Ct, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.32 Acre
    • $343,750 per Acre

    135 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    135 Jacob Ct, Winchester, KY 40391
  • /2

    $165,000 Sold May 30, 2025

    • 1,200 Sq Ft
    • $138/SF
    • 3 Beds
    • 1.5 Baths
    • Built 1988

    44 Heather Ln, Winchester, KY 40391

    COMP SALE

    Null Non-Member Non-Member Office

    44 Heather Ln, Winchester, KY 40391
    • /32

      Est $258,889 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,632 Sq Ft

      411 Wellington Way, Winchester, KY 40391

      411 Wellington Way, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.47 Acre
    • $234,043 per Acre

    139 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    139 Jacob Ct, Winchester, KY 40391
  • /2

    $401,500 Sold May 15, 2025

    • 2,000 Sq Ft
    • $201/SF
    • 3 Beds
    • 2 Baths
    • Built 1998

    108 Royal Oak Dr, Winchester, KY 40391

    FSBO For Comp Purposes Only ! High ceilings freshly painted home. Both bathrooms and kitchen remodeled in 2015. Roof replaced 2015.

    Null Non-Member Non-Member Office

    108 Royal Oak Dr, Winchester, KY 40391
    • /43

      Est $277,020 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft

      218 Abbeywood Dr, Winchester, KY 40391

      218 Abbeywood Dr, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.59 Acre
    • $186,441 per Acre

    255 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    255 Duclair Dr, Winchester, KY 40391
  • /2

    $195,000 Sold May 15, 2025

    • 1,822 Sq Ft
    • $107/SF
    • 4 Beds
    • 2 Baths
    • Built 1980

    105 Churchill Dr, Winchester, KY 40391

    comp purposes

    Null Non-Member Non-Member Office

    105 Churchill Dr, Winchester, KY 40391
    • /48

      Est $339,809 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,952 Sq Ft

      208 Abbeywood Dr, Winchester, KY 40391

      208 Abbeywood Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 1.10 Acres
    • $90,909 per Acre

    270 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    270 Duclair Dr, Winchester, KY 40391
  • /2

    $216,450 Sold Apr 30, 2025

    • 1,628 Sq Ft
    • $133/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    408 Paisley Ct, Winchester, KY 40391

    New Paint and Carpet.

    John Wilson Bluegrass Properties Group

    408 Paisley Ct, Winchester, KY 40391
    • /15

      Est $244,613 Not Listed For Sale

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

      434 Wellington Way, Winchester, KY 40391

      434 Wellington Way, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.50 Acre
    • $220,000 per Acre

    260 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    260 Duclair Dr, Winchester, KY 40391
  • /2

    $201,000 Sold Apr 18, 2025

    • 960 Sq Ft
    • $209/SF
    • 2 Beds
    • 2 Baths
    • Built 1993

    203 Arbor Ct, Winchester, KY 40391

    Beautifully remodeled and updated cottage home! Gorgeous kitchen with white cabinets & new stainless steel appliances. Primary bedroom has attached bath with new fixtures & 5' shower. Main bath has all new fixtures including soaking tub. All new laminate flooring thru-out. Upgraded 200 amp electrical service, new heat pump, new shingles, new windows & more! Relax on your screened in porch

    Angie Conley Dixon Dixon Properties

    203 Arbor Ct, Winchester, KY 40391
    • /11

      Est $238,134 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,699 Sq Ft

      119 Sturbridge Ln, Winchester, KY 40391

      119 Sturbridge Ln, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.32 Acre
    • $343,750 per Acre

    250 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    250 Duclair Dr, Winchester, KY 40391
  • /2

    $415,000 Sold Mar 03, 2025

    • 2,470 Sq Ft
    • $168/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths

    1480 White Turley Rd, Winchester, KY 40391

    Charming 3-bedroom, 2-bath home on 5 acres with beautiful views, featuring new flooring throughout. This property is full of life, with abundant wildlife and a variety of fruit-bearing trees, including 2 apple trees, 2 peach trees, 2 pear trees, a grapevine, blackberry bushes, and walnut trees. There's also a chicken coop, a goat enclosure, and a fenced yard, providing ample space for all your

    Hannah Porter DEE'S REAL ESTATE SERVICE

    1480 White Turley Rd, Winchester, KY 40391
    • /3

      Est $247,893 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,719 Sq Ft

      128 Sturbridge Ln, Winchester, KY 40391

      128 Sturbridge Ln, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.34 Acre
    • $323,529 per Acre

    230 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    230 Duclair Dr, Winchester, KY 40391
  • /2

    $125,000 Sold May 23, 2025

    • Land
    • 1.01 Acres
    • $123,762 per Acre
    • 0 Days On Market

    265 Duclair Dr, Winchester, KY 40391

    John Wilson Bluegrass Properties Group

    265 Duclair Dr, Winchester, KY 40391
    • /6

      Est $233,894 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 22,043 Sq Ft

      126 Sturbridge Ln, Winchester, KY 40391

      126 Sturbridge Ln, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.38 Acre
    • $289,474 per Acre

    200 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    200 Duclair Dr, Winchester, KY 40391
  • /2

    $260,000 Sold May 01, 2025

    • 2,766 Sq Ft
    • $94/SF
    • 4 Beds
    • 3.5 Baths
    • Built 1993

    497 Goose Creek Rd, Winchester, KY 40391

    Shari Frasure Keller Williams Commonwealth

    497 Goose Creek Rd, Winchester, KY 40391
    • /3

      Est $256,427 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,519 Sq Ft

      124 Sturbridge Ln, Winchester, KY 40391

      124 Sturbridge Ln, Winchester, KY 40391
  • /2

    $150,000

    • Land
    • 2.11 Acres
    • $71,090 per Acre

    125 Knox Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    125 Knox Ct, Winchester, KY 40391
  • /2

    $4,360,000 Sold Jan 09, 2025

    • 1,330 Sq Ft
    • $3278/SF
    • 0 Days On Market
    • Built 2006

    1403 Westwood Dr, Winchester, KY 40391

    Wes Durrant Crye-Leike Executive Realty

    1403 Westwood Dr, Winchester, KY 40391
    • /4

      Est $240,206 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,281 Sq Ft

      122 Sturbridge Ln, Winchester, KY 40391

      122 Sturbridge Ln, Winchester, KY 40391
  • /2

    $150,000

    • Land
    • 2.16 Acres
    • $69,444 per Acre

    120 Knox Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    120 Knox Ct, Winchester, KY 40391
    • /19

      Est $227,591 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,192 Sq Ft

      120 Sturbridge Ln, Winchester, KY 40391

      120 Sturbridge Ln, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.29 Acre
    • $379,310 per Acre

    160 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    160 Duclair Dr, Winchester, KY 40391
    • /3

      Est $237,675 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,719 Sq Ft

      116 Sturbridge Ln, Winchester, KY 40391

      116 Sturbridge Ln, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.35 Acre
    • $314,286 per Acre

    150 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    150 Duclair Dr, Winchester, KY 40391
    • /4

      Est $260,878 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,519 Sq Ft

      114 Sturbridge Ln, Winchester, KY 40391

      114 Sturbridge Ln, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.49 Acre
    • $224,490 per Acre

    130 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    130 Duclair Dr, Winchester, KY 40391

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