Winchester, KY Homes

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  /22

  $265,000 Sold Aug 23, 2024

  • 1,400 Sq Ft
  • $189/SF
  • 8 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1975

  759 Wayland Dr, Winchester, KY 40391

  Wonderful Brick Ranch with beautiful large yard. 2 car detached garage with side workshop. Storage bldg for lawn equipment. Generator is a bonus. Great location minutes from shopping, hospital and interstate. Same owner for 22 years. Sunroom w patio doors and screens. Plenty of room for entertaining or just relaxing, Great home for anyone! Showings begin at the Open house this Saturday August

  Michelle Riggs Waldron Properties, LLC

  759 Wayland Dr, Winchester, KY 40391
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  /12

  Est $209,156 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,264 Sq Ft

  8 Nunnelly Ct, Winchester, KY 40391

  8 Nunnelly Ct, Winchester, KY 40391
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  /38

  $749,000

  • 6 Beds
  • 4.5 Baths
  • 4,021 Sq Ft

  4455 Colby Rd, Winchester, KY 40391

  Experience country living in this stunning home on 3.56 acres located in a highly desirable area. Minutes from town and a short 15 minute drive to Hamburg. Enjoy beautiful views of the country from the covered front and back porches, perfect for morning coffee or evening gatherings. Open concept living. Spacious bedrooms. Partially finished basement. Beautiful sunroom. Updates throughout. Call

  Brian England Keller Williams Bluegrass Realty

  4455 Colby Rd, Winchester, KY 40391
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  /72

  $460,000 Sold Aug 05, 2024

  • 2,800 Sq Ft
  • $164/SF
  • 60 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2024

  127 Hibiscus Ln, Winchester, KY 40391

  This new construction house will be completed soon and ready for you to move in and call home! From the moment you step inside, you'll find stunning features including 9 foot ceilings for an open and airy feel, with hardwood floors throughout. In the kitchen will be granite countertops with white cabinets including an island with bar top seating. New stainless appliances will complete the

  Josh Wood Freedom Realty & Property Mgt

  127 Hibiscus Ln, Winchester, KY 40391
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  /30

  Est $261,206 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,714 Sq Ft

  119 W Hickman St, Winchester, KY 40391

  119 W Hickman St, Winchester, KY 40391
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  /32

  $425,000

  • 4 Beds
  • 3.5 Baths
  • 2,904 Sq Ft

  210 College St, Winchester, KY 40391

  HISTORIC PRESERVATION AWARD! This stately brick residence, was among the winners of the 2024 Historic Preservation Award by the Clark County-Winchester Heritage Board and the Winchester Historic Preservation Board. Great attention was given to preserving/replicating original features of the home while bringing it to modern day living. Features of this gorgeous home include original heart pine

  Angie Conley Dixon Dixon Properties

  210 College St, Winchester, KY 40391
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  /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
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  /43

  Est $259,583 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,415 Sq Ft

  144 W Lexington Ave, Winchester, KY 40391

  144 W Lexington Ave, Winchester, KY 40391
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  /32

  $275,000

  • 4 Beds
  • 2 Baths
  • 2,808 Sq Ft

  16 Taylor Ave, Winchester, KY 40391

  STOP scrolling and LOOK! This charming and pristine home is clean as a whistle and just a short walk to active and historic downtown Winchester. Sit on the covered front porch in the summertime shade or on the deck/patio overlooking the spacious/private backyard. Move-in ready with lots of space inside and out (over 2800 sq.ft. finished!), 4 large bedrooms, 2 full baths (one upstairs and one

  Jim Woodrum RE/MAX Creative, Winchester

  16 Taylor Ave, Winchester, KY 40391
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  /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
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  /35

  Est $251,593 Not Listed For Sale

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

  231 W Hickman St, Winchester, KY 40391

  231 W Hickman St, Winchester, KY 40391
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  /93

  $749,000

  • 4 Beds
  • 4 Baths
  • 4,644 Sq Ft

  110 Camelot Dr, Winchester, KY 40391

  Don't miss this rare opportunity to abide in one of Winchester's finest locations, Camelot Drive. A hidden gem tucked away in the back of Hampton Manor, this home boasts space and privacy on an idyllic cul-de-sac just off Boone Avenue. Details such as crown molding, built-in cabinetry, high ceilings, 2 fireplaces, transom windows, and hardwood floors fill this home with character and charm.

  Joyce Ratliff Tom Goebel & Company

  110 Camelot Dr, Winchester, KY 40391
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  /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
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  /32

  Est $240,714 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,053 Sq Ft

  227 W Hickman St, Winchester, KY 40391

  227 W Hickman St, Winchester, KY 40391
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  /16

  $175,000

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft

  117 Buffalo Trace, Winchester, KY 40391

  NEW Price Reduction!!! Perfect 3 Bedroom 2 Bathroom Home For A First Time HomeBuyer Or Someone Downsizing. Location Is Convenient To The Interstate, Shopping And Downtown! Nice Size Backyard And Plenty Of Parking In The Front. Shed In The Backyard Is Included. Make This Beautiful And Affordable Home Yours Before The Holidays!

  Patrick Arvin Keller Williams Commonwealth

  117 Buffalo Trace, Winchester, KY 40391
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  /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
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  /24

  Est $294,238 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,180 Sq Ft

  114 S Burns Ave, Winchester, KY 40391

  114 S Burns Ave, Winchester, KY 40391
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  /29

  $427,900

  • 4 Beds
  • 3 Baths
  • 2,361 Sq Ft

  4732 Old Boonesboro Rd, Winchester, KY 40391

  NEW PRICE REDUCTION!!! This Is The One You Have Been Waiting For!!! This Completely Remodeled 4 Bedroom 3 Bathroom Home On An Unfinished Basement Has It All. Features Include An Open Floor Plan; Dining Room With Fireplace; Big Kitchen With Lots Of Cabinets; Granite Tops; Stainless Steel Appliances; Range Hood; Farmhouse Sink; Huge Laundry Room Off Kitchen/Master Bedroom; First Floor Master

  Patrick Arvin Keller Williams Commonwealth

  4732 Old Boonesboro Rd, Winchester, KY 40391
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  /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
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  /52

  Est $272,759 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,092 Sq Ft

  328 S Burns Ave, Winchester, KY 40391

  328 S Burns Ave, Winchester, KY 40391
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  /48

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft

  40 N Burns Ave, Winchester, KY 40391

  This stunning fully remodeled 3-bedroom, 2-bathroom home is move-in ready with top-to-bottom updates. Every detail has been thoughtfully upgraded, from the modern lighting in every room to the brand-new flooring and fresh paint throughout. The kitchen is a standout with granite countertops, new cabinetry, and brand-new appliances, while the bathrooms boast quartz countertops and elegant tiled

  Ernesto Martinez Berkshire Hathaway HomeServices Foster Realtors

  40 N Burns Ave, Winchester, KY 40391
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  /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
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  /32

  Est $293,764 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,991 Sq Ft

  322 S Burns Ave, Winchester, KY 40391

  322 S Burns Ave, Winchester, KY 40391
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  /2

  $150,000

  • Land
  • 2.77 Acres
  • $54,152 per Acre

  3385 Colby Rd, Winchester, KY 40391

  Small acreage lot on Colby Road! Accessed by easement from neighbors driveway.

  Steve Adams Steven D Adams Real Est Serv

  3385 Colby Rd, Winchester, KY 40391
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  /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
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  /51

  Est $369,037 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,227 Sq Ft

  200 College St, Winchester, KY 40391

  200 College St, Winchester, KY 40391
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  /67

  $715,000

  • 3 Beds
  • 4 Baths
  • 4,123 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Own the most charming home atop a scenic hill at Blue Ridge Manor—a breathtaking 5.13-acre retreat where modern comfort meets classic elegance. As you drive up the long, private driveway, you'll feel like you're entering your own exclusive retreat, a sanctuary of peace and tranquility. Lovingly maintained by its original owner for the past 30 years, this beautifully renovated brick home (updated

  Oxana Lopetegui-Pineda Lifstyl Real Estate

  1775 Irvine Rd, Winchester, KY 40391
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  /53

  Est $263,281 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,170 Sq Ft

  214 S Burns Ave, Winchester, KY 40391

  214 S Burns Ave, Winchester, KY 40391
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  /10

  $1,500,000

  • Land
  • 74 Acres
  • $20,322 per Acre

  3505 Basin Springs Rd, Winchester, KY 40391

  Located in the heart of Clark County this 73+/- acre property has been a part of the family since the 1800s. With its expansive space and fertile land, it offers endless possibilities for agricultural ventures, recreational use or development. Whether you're looking to expand your farming operation or create a private estate, this rare property presents a fantastic opportunity to invest in land

  Kathryn Cheuvront Coldwell Banker McMahan

  3505 Basin Springs Rd, Winchester, KY 40391
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  /16

  Est $167,512 Not Listed For Sale

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

  227 W Broadway St, Winchester, KY 40391

  227 W Broadway St, Winchester, KY 40391
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  /5

  $110,000

  • Land
  • 2.06 Acres
  • $53,398 per Acre

  1185 Craig Crossing Rd, Winchester, KY 40391

  Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  1185 Craig Crossing Rd, Winchester, KY 40391
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  /28

  Est $185,400 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  18 A St, Winchester, KY 40391

  18 A St, Winchester, KY 40391
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  /6

  $180,000

  • Land
  • 4.45 Acres
  • $40,449 per Acre

  1030 Craig Crossing Rd, Winchester, KY 40391

  Lot # 14 contains 4.450 acres of gently rolling land with small stream perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  1030 Craig Crossing Rd, Winchester, KY 40391
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  /22

  Est $178,894 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  339 W Washington St, Winchester, KY 40391

  339 W Washington St, Winchester, KY 40391
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  /7

  $195,000

  • Land
  • 6 Acres
  • $31,707 per Acre

  990 Craig Crossing Rd, Winchester, KY 40391

  Lot # 13 contains 6.153 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  990 Craig Crossing Rd, Winchester, KY 40391
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  /35

  Est $322,895 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,270 Sq Ft

  149 Milwood Dr, Winchester, KY 40391

  149 Milwood Dr, Winchester, KY 40391
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  /24

  $329,500

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  360 N Middletown Rd, Winchester, KY 40391

  Investment Opportunity! This is the Child Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 (titled) Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of potential. You could

  Danielle Haggard Keller Williams Commonwealth

  360 N Middletown Rd, Winchester, KY 40391
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  /41

  Est $309,103 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  173 Milwood Dr, Winchester, KY 40391

  173 Milwood Dr, Winchester, KY 40391
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  /29

  $329,500

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  374 N Middletown Rd, Winchester, KY 40391

  Investment Opportunity! This is the Parent Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 (titled) Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of potential. You could

  Danielle Haggard Keller Williams Commonwealth

  374 N Middletown Rd, Winchester, KY 40391
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  /27

  Est $263,633 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,650 Sq Ft

  36 Fitch Ave, Winchester, KY 40391

  36 Fitch Ave, Winchester, KY 40391

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