Winchester, KY Homes

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  /14

  Est $318,667 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,084 Sq Ft

  900 Beckwood Ln, Winchester, KY 40391

  900 Beckwood Ln, Winchester, KY 40391
• 

  

  

  /41

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft

  118 Windridge Dr, Winchester, KY 40391

  Located in the Windridge neighborhood with easy access to both Bypass Rd and Boone Ave, this charming brick ranch offers 3 bedrooms, 2 full baths, and character throughout. Inside, you'll find hardwood and tile floors (no carpet!), a spacious kitchen with plenty of cabinet space that opens into the dining area and living room, complete with a cozy ventless gas fireplace. Step out back to your own

  Michelle Blackburn RE/MAX Creative, Winchester

  118 Windridge Dr, Winchester, KY 40391
• 

  

  

  /51

  $428,000 Sold Sep 04, 2025

  • 3,181 Sq Ft
  • $135/SF
  • 34 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1960

  17 Hampton Ave, Winchester, KY 40391

  This meticulous house is located within walking distance of many popular Winchester destinations; The Winchester Country Club, The Public Library and the indoor gym and swimming facility at College Park. Now back to the meticulous house. When you enter the front door you will immediately feel the how the owners have taken such great care of this house. The gleaming hardwoods, the large living

  Craig Bridgewater Bridgewater Real Estate

  17 Hampton Ave, Winchester, KY 40391
• 

  

  

  /33

  Est $302,503 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft

  11440 Irvine Rd, Winchester, KY 40391

  11440 Irvine Rd, Winchester, KY 40391
• 

  

  

  /42

  $399,900

  • 4 Beds
  • 3.5 Baths
  • 2,718 Sq Ft

  210 College St, Winchester, KY 40391

  Welcome to one of Winchester's most iconic and award-winning homes—a stunning 4-bedroom, 3.5-bath historic residence spanning over 2,700 square feet. This exceptional property, recipient of a Historic Preservation Award, beautifully balances timeless character with modern comfort. From the moment you step onto the newly built wide front porch, the home's undeniable charm begins to unfold. Inside,

  Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
• 

  

  /33

  $385,000 Sold Sep 04, 2025

  • 2,741 Sq Ft
  • $140/SF
  • 12 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1985

  113 Shala Mar Rue, Winchester, KY 40391

  Beautifully maintained brick ranch on a full basement, offering over 4,000 square feet under roof in a highly desirable location just minutes from Hamburg, I-64, Lexington, and Clark County Regional Hospital. This spacious home features 4 bedrooms, 3 full baths, and stunning hardwood floors. Two impressive floor-to-ceiling fireplaces add charm on both levels. The kitchen includes new stainless

  Rebakah Goodpaster Keller Williams Legacy Group

  113 Shala Mar Rue, Winchester, KY 40391
• 

  

  /26

  Est $291,413 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,668 Sq Ft

  11705 Irvine Rd, Winchester, KY 40391

  11705 Irvine Rd, Winchester, KY 40391
• 

  

  /18

  $389,900

  • 3 Beds
  • 3 Baths
  • 2,516 Sq Ft

  110 Hampton Ave, Winchester, KY 40391

  Move-in ready mid- century brick ranch home! Features 3 bedrooms, 3 full baths, new kitchen with granite countertops, 3 woodburning fireplaces, formal dining or family room, full basement with huge rec room or space to have 4th bedroom, 1 car garage, 2 storage buildings & fenced in yard! Updates include windows, doors, metal roof, new paint inside & out, new flooring in basement & bedrooms, all

  Angie Conley Dixon Dixon Properties

  110 Hampton Ave, Winchester, KY 40391
• 

  

  /22

  $201,000 Sold Sep 04, 2025

  • 1,235 Sq Ft
  • $163/SF
  • 26 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1980

  110 Colonial Park Dr, Winchester, KY 40391

  Relax in your private paradise! The fully privacy fenced backyard hides the pool and deck area along with the really cool hot tub room, huge dog kennel, and storage shed. 3 bedrooms, all one level, newer roof and HVAC system. Come see what sets this home apart from all the rest!

  Jason Townsend Kentucky Residential Real Estate, LLC

  110 Colonial Park Dr, Winchester, KY 40391
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  /49

  Est $451,634 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,800 Sq Ft

  8360 Irvine Rd, Winchester, KY 40391

  8360 Irvine Rd, Winchester, KY 40391
• 

  

  /13

  $340,000

  • 6 Beds
  • 4 Baths
  • 4,456 Sq Ft

  410 W Lexington Ave, Winchester, KY 40391

  Estate Sale. Selling 'AS IS', in 2024 new roof, walls repaired and freshly painted throughout.Great home for a growing family, covered front porch, 10-foot ceilings upstairs and down, handicap ramp, ample parking in rear. Motivated seller, call for your private showing today

  Melisa McDonald Wrenn Realty

  410 W Lexington Ave, Winchester, KY 40391
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  /48

  $550,000 Sold Sep 04, 2025

  • 3,489 Sq Ft
  • $158/SF
  • 43 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2007

  594 Earlymeade Dr, Winchester, KY 40391

  This stunning 5BR,3BA brick home blends classic charm with modern comfort, all situated in a highly desirable neighborhood. The exterior features clean lime wash brick with contrasting painted trim and a crisp new black roof, new black 6mm gutters, exuding timeless curb appeal. A wide front porch with elegant columns welcomes you into the home, perfect for relaxing or greeting guest.Inside you

  Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391
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  /33

  Est $266,346 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,592 Sq Ft

  510 Wills Rupard Rd, Winchester, KY 40391

  510 Wills Rupard Rd, Winchester, KY 40391
• 

  

  /4

  $369,900 New Construction

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

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
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  /15

  $110,000 Sold Sep 04, 2025

  • 924 Sq Ft
  • $119/SF

  • 3 Beds
  • 2 Baths
  • Built 2024

  706 Williamsburg Dr, Winchester, KY 40391

  This is your opportunity to buy a brand new Clayton tru elation single wide mobile home. 3 bed 2 bath all electric. The .11 acre lot conveys. New front porch and back steps. This house is in the Yorktown trailer park. They currently have an HOA fee of $150 a month and that covers your water, sewer, and trash. The park also offers a play ground for the kids. Please confirm you read over all park

  Andrew Fugitt Coldwell Banker McMahan

  706 Williamsburg Dr, Winchester, KY 40391
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  /33

  Est $238,842 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  7344 Ironworks Rd, Winchester, KY 40391

  7344 Ironworks Rd, Winchester, KY 40391
• 

  

  /3

  $380,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  270 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
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  /28

  $370,000 Sold Sep 03, 2025

  • 3,078 Sq Ft
  • $120/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  220 Spring Valley Dr, Winchester, KY 40391

  This beautiful 5 acre property is a rare find! Located on a quiet cul-de-sac just minutes from I-64, Winchester and Bourbon County, this home offers the perfect blend of tranquility and convenience. The home includes 4 bedrooms, 2.5 baths with a mostly finished basement providing additional living space and storage. There are 2 wood burning fireplaces, perfect for cozy evenings. Additionally,

  Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
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  /82

  Est $398,433 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,173 Sq Ft

  380 L E Junction Rd, Winchester, KY 40391

  380 L E Junction Rd, Winchester, KY 40391
• 

  

  /3

  $380,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  230 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  230 Evergreen Dr, Winchester, KY 40391
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  /33

  $180,000 Sold Sep 02, 2025

  • 1,000 Sq Ft
  • $180/SF
  • 22 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1977

  307 Blair Ave, Winchester, KY 40391

  This charming 3-bedroom, 1-bath ranch offers fresh updates throughout, including brand new flooring and interior paint. The inviting side porch features a ramp for easy accessibility and leads to a spacious patio—perfect for relaxing or entertaining. A detached two-car garage adds great storage and functionality. Located just minutes from downtown Winchester and I-64, this move-in-ready home

  Brooke Otis Mullins RO&CO Real Estate

  307 Blair Ave, Winchester, KY 40391
• 

  

  /51

  Est $524,222 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,841 Sq Ft

  5600 Ecton Rd, Winchester, KY 40391

  5600 Ecton Rd, Winchester, KY 40391
• 

  

  /3

  $345,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  225 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  225 Evergreen Dr, Winchester, KY 40391
• 

  

  /41

  $259,900 Sold Aug 31, 2025

  • 1,544 Sq Ft
  • $168/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  315 Newcastle Ln, Winchester, KY 40391

  Nestled in a cul-de-sac in Winchester's Oakmont neighborhood, this 3-bedroom, 2.5-bath home offers comfort and convenience. The main level features vinyl plank flooring throughout, a spacious living room, and an eat-in kitchen, plus a laundry area and half bath. Upstairs, you'll find three generously sized bedrooms, including a primary suite with a walk-in closet and private bath. A second full

  Terra Long Keller Williams Commonwealth

  315 Newcastle Ln, Winchester, KY 40391
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  /38

  Est $384,573 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,866 Sq Ft

  3070 Goshen Rd, Winchester, KY 40391

  3070 Goshen Rd, Winchester, KY 40391
• 

  /2

  $345,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  215 Evergreen Dr, Winchester, KY 40391

  Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  215 Evergreen Dr, Winchester, KY 40391
• 

  

  /10

  $325,000 Sold Aug 29, 2025

  • 1,584 Sq Ft
  • $205/SF

  • 3 Beds
  • 2 Baths
  • Built 1999

  210 Cabin Creek Rd, Winchester, KY 40391

  3 Bedroom 2 Bath brick ranch home on almost 2 acres.

  Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /49

  Est $374,428 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,560 Sq Ft

  2068 Goshen Rd, Winchester, KY 40391

  2068 Goshen Rd, Winchester, KY 40391
• 

  

  /46

  $284,900

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft

  165 Hilltop Dr, Winchester, KY 40391

  This stunning property is ideally located and is an absolute must see! This lovely home is located on over a quarter acre lot with gorgeous farm views. Featuring an open floor plan that is perfect for entertaining, a beautiful kitchen with granite countertops, stainless appliances, and a large island. The primary suite offers a large en-suite full bath with a double bowl raised vanity. This

  Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
• 

  

  /25

  $375,000 Sold Aug 29, 2025

  • 3,111 Sq Ft
  • $121/SF
  • 8 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2001

  317 Hanover Dr, Winchester, KY 40391

  Looking for room to grow? Welcome to 317 Hanover Drive, a spacious and inviting home located in the popular Colby Ridge neighborhood—just minutes from all the shopping, dining, and conveniences Winchester has to offer. This beautiful 5-bedroom, 3.5-bath home offers a finished walkout basement and thoughtful touches throughout. Enjoy relaxing evenings on the charming front porch or entertain on

  Mike Wheatley Bluegrass Properties Group

  317 Hanover Dr, Winchester, KY 40391
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  /32

  Est $307,021 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  810 Howard Creek Rd, Winchester, KY 40391

  810 Howard Creek Rd, Winchester, KY 40391
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  /4

  $64,900

  • Land
  • 0.64 Acre
  • $101,406 per Acre

  102 Royal Oak Dr, Winchester, KY 40391

  A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..64 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

  Melia Hord Keller Williams Bluegrass Realty

  102 Royal Oak Dr, Winchester, KY 40391
• 

  

  /41

  $249,900 Sold Aug 29, 2025

  • 2,146 Sq Ft
  • $116/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  407 Walnut St, Winchester, KY 40391

  Welcome to this beautifully remodeled brick ranch sitting on a massive 1.2-acre corner lot in the heart of Winchester! This home blends modern updates with timeless charm and offers 3 spacious bedrooms, 2 full bathrooms, and a versatile bonus room that could easily serve as a fourth bedroom, home office, or playroom. Step inside to find fresh paint, brand new flooring throughout, all-new windows,

  Jason Crask THRIVE Realty

  407 Walnut St, Winchester, KY 40391
• 

  

  /53

  Est $286,339 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,126 Sq Ft

  1489 White Conkwright Rd, Winchester, KY 40391

  1489 White Conkwright Rd, Winchester, KY 40391
• 

  

  /4

  $64,900

  • Land
  • 0.52 Acre
  • $124,808 per Acre

  101 Royal Oak Dr, Winchester, KY 40391

  A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..52 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

  Melia Hord Keller Williams Bluegrass Realty

  101 Royal Oak Dr, Winchester, KY 40391
• 

  

  /40

  $331,000 Sold Aug 29, 2025

  • 1,988 Sq Ft
  • $166/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  13544 Irvine Rd, Winchester, KY 40391

  Experience Stunning Sunrises and Starry Nights!Nestled on nearly 4 peaceful acres, this charming brick ranch offers the tranquility of country living with modern comfort. Surrounded by a beautiful tree grove, the home features a full walk-out basement with exciting potential—finish the lower level and additional bathroom to expand your living space!Inside, you'll find 3 spacious

  Susan Baldwin Rector Hayden Realtors

  13544 Irvine Rd, Winchester, KY 40391
• 

  

  /23

  Est $305,454 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  440 White Conkwright Rd, Winchester, KY 40391

  440 White Conkwright Rd, Winchester, KY 40391
• 

  

  /10

  $215,000

  211 Ashton Oak Way, Winchester, KY 40391

  Here is the Blank Canvas to build your Dream Home in the Plantation Subdivision. This two story brick building, formerly the Sales Office for the Subdivision, has been gutted to offer the unique opportunity to build a 3118 Sq Ft Home consisting of Four Bedrooms, Two and Half Baths, an open concept on the main level with the addition of a two car garage. Contact listing agent to discuss current

  Melia Hord Keller Williams Bluegrass Realty

  211 Ashton Oak Way, Winchester, KY 40391
• 

  

  /23

  $335,000 Sold Aug 27, 2025

  • 2,936 Sq Ft
  • $114/SF
  • 8 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1986

  413 Lyon Dr, Winchester, KY 40391

  Well maintained in an established neighborhood on a large corner lot. Nice hardwood floors in the dining area. Dental crown molding and chair rail in the living room and kitchen/dining area. Book shelves and wood stove in the den. Room in the basement could be an additional bedroom. Large basement garage with cabinets. Front brick porch, rear 10'x16' all season room, rear court yard and deck

  Ray Rush Rush Real Estate

  413 Lyon Dr, Winchester, KY 40391
• 

  

  /78

  Est $606,556 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,689 Sq Ft

  7625 Irvine Rd, Winchester, KY 40391

  7625 Irvine Rd, Winchester, KY 40391

Showing Results 81 - 120, Page 3 of 18