Winchester, KY Homes for Sale

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  $574,000

  • 5 Beds
  • 3 Baths
  • 3,102 Sq Ft

  110 White Conkwright Rd, Winchester, KY 40391

  Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

  

  Philip 'PJ' Elder

  Omega Real Estate Brokerage LLC

  (859) 209-6934

  110 White Conkwright Rd, Winchester, KY 40391
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  /67

  $699,000 Open Sun 1PM - 3PM

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

  1775 Irvine Rd, Winchester, KY 40391

  Just 12 minutes from Lexington, 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

  

  Oxana Lopetegui-Pineda

  Lifstyl Real Estate

  (859) 659-6462

  1775 Irvine Rd, Winchester, KY 40391
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  /117

  $3,175,000

  • 8 Beds
  • 7.5 Baths
  • 12,702 Sq Ft

  4664 Lexington Rd, Winchester, KY 40391

  Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot

  Zach Davis Kirkpatrick & Company

  4664 Lexington Rd, Winchester, KY 40391
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  /65

  $713,500

  • 6 Beds
  • 4.5 Baths
  • 6,243 Sq Ft

  418 David Ln, Winchester, KY 40391

  This impeccable house is a Buyer's Delight. Located in the most desirable residential neighborhood, Stoney Brook. Discover a serene retreat in this beautifully appointed home, offering spacious interiors and breathtaking outdoor spaces. Step into the front door and discover the soaring ceilings with beautifully appointed crown molding. The flowing space from the dining room to the great room to

  Craig Bridgewater Bridgewater Real Estate

  418 David Ln, Winchester, KY 40391
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  /34

  $380,000

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  148 Gibson Way, Winchester, KY 40391

  NEW PRICE!Better Than New Construction!!! This Spacious 4 Bedroom 2 1/2 Bath Home Is Move In Ready And Has A Beautiful Farm View From Your Covered Porch. Features Include A Large Open Living Room And Kitchen With Plenty Of Cabinet Space; Large Island With Faucet; Granite Countertops; Tile Backsplash; Stainless Steel Appliances; Large pantry; Gas Log Fireplace; Gas Heat; Gas Water Heater;

  Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
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  /53

  $559,000

  • 4 Beds
  • 3 Baths
  • 2,482 Sq Ft

  5 Fairwood Ln, Winchester, KY 40391

  Just a two minute walk from Winchester Country Club, this architect-designed 4BR/3BA split-level home was taken to the studs in 2013 and rebuilt with timeless craftsmanship and modern ease. Light-filled spaces, rich hardwood floors, a custom kitchen by Shaker Village's Terry Craycraft, granite countertops, abundant cabinetry, and a hidden pantry.. The spa-like main-level primary suite is a true

  Kathryn Cheuvront Coldwell Banker McMahan

  5 Fairwood Ln, Winchester, KY 40391
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  /36

  $419,900

  • 4 Beds
  • 4.5 Baths
  • 2,800 Sq Ft

  136 College St, Winchester, KY 40391

  Welcome to this stunning, fully renovated 4-bedroom, 4.5-bathroom home in the heart of downtown Winchester. Thoughtfully redesigned with a rear addition, this property now features a spacious first-floor primary suite complete with a private bathroom, walk-in closet, and convenient laundry access.Each of the four bedrooms has its own private en-suite bathroom, offering comfort and privacy

  Danielle Hatton The Brokerage

  136 College St, Winchester, KY 40391
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  /2

  $395,000

  • 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
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  /80

  $598,000

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft

  160 Agawam Rd, Winchester, KY 40391

  Charming Brick Ranch on 5 Fenced Acres - Ideal for Country Living! Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-acre fenced lot. This versatile property offers the perfect blend of comfort, functionality, and rural charm - ideal for families, hobby farmers, or equestrian enthusiasts. Inside, you'll find 3 bedrooms and 3 bathrooms with a fully finished

  Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
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  /56

  $729,000

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

  4455 Colby Rd, Winchester, KY 40391

  Gorgeous Ranch Home On Basement, Situated Perfectly On Over 3.5 Lush Acres Of Level Seclusion, As Property Is Lined Beautiful, Mature Trees! Enjoy Peace & Quiet In This Newly Renovated Home, Offering 6 Bedrooms, 5 Baths, Ample Family Space, Home Office, (Fiber Optic Internet), Large Separate Laundry, Sun Room, 2 Covered Porches, Deck, Fire Pit, 2 Car Garage, Barn/ Workshop... THE LIST GOES ON!

  Melissa Thompson Keller Williams Legacy Group

  4455 Colby Rd, Winchester, KY 40391
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  $379,000

  • 4 Beds
  • 2.5 Baths
  • 2,829 Sq Ft

  219 Hampton Ave, Winchester, KY 40391

  This ranch home in Winchester, Kentucky offers spacious living, modern comfort, and tons of updates that have been made to ensure purchase confidence. Inside, the living room features a brick fireplace and a large picture window that fills the space with natural light. The kitchen is outfitted with white cabinetry, a peninsula-style countertop, and stainless steel appliances, and flows into a

  Slava Furs 85W Real Estate

  219 Hampton Ave, Winchester, KY 40391
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  /51

  $445,000

  • 4 Beds
  • 2 Baths
  • 3,181 Sq Ft

  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
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  /39

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  600 Ferry Rd, Winchester, KY 40391

  Experience abundant wildlife with turkey and deer in your own hunting retreat, or simply enjoy the views from your backyard on this stunning 33-acre property. Conveniently located near the Kentucky River, with a boat ramp nearby, this home offers the perfect blend of nature and accessibility, making it ideal for nature lovers or those who enjoy fishing and hunting.Step inside to the foyer,

  Cathleen Gedeon CENTURY 21 Advantage Realty

  600 Ferry Rd, Winchester, KY 40391
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  /3

  $380,000

  • 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 and a

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  265 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, walkout unfinished basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  265 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
• 

  

  /3

  $380,000

  • 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
• 

  

  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  220 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

  Rex Hall United Real Estate Bluegrass

  220 Evergreen Dr, Winchester, KY 40391
• 

  

  /3

  $380,000

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

  200 Evergreen Dr, Winchester, KY 40391

  Introducing the Run For The Roses - 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 bathroom. The kitchen

  Rex Hall United Real Estate Bluegrass

  200 Evergreen Dr, Winchester, KY 40391
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  /62

  $379,900

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  309 Gallahadion Ct, Winchester, KY 40391

  This beautiful home located in desirable Fairholme Estates is a must see!! Amazing open floor plan with kitchen granite countertops, a large island and upgraded Frigidaire Elite Stainless Appliances. The waterproof Pergo laminate flooring is throughout the home. Don't miss the primary bedrooms with walk in closet, double sinks and tile shower in the bathroom. The two car garage is located on

  Josh Wood Freedom Realty & Property Mgt

  309 Gallahadion Ct, Winchester, KY 40391
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  /17

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  104 Colby Hills Dr, Winchester, KY 40391

  Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

  Garry Milton Milton and Associates Real Estate

  104 Colby Hills Dr, Winchester, KY 40391
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  /46

  $455,000

  • 3 Beds
  • 2.5 Baths
  • 3,261 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  Beautiful Hampton Manor home offers easy access to all Winchester has to offer! Located right off Boone Ave, this home boasts tons of updates including an Entertaiment Kitchen with granite countertops, Bosch appliances and great storage, refinished hardwoods, new windows, Updated bathroom showers, a pool, covered front porch back porch and separate covered area outback to enjoy all summer long. 3

  Whitney Ensor Ensor Real Estate LLC

  42 Mockingbird Valley Rd, Winchester, KY 40391
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  /2

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 2,189 Sq Ft

  4541 Colby Rd, Winchester, KY 40391

  ''Discover the perfect blend of comfort and country charm in this 4-bedroom, 2.5-bath home! Nestled in a serene setting, this property boasts a beautifully front and back yard, offering ample space for relaxation and outdoor enjoyment. Whether you're savoring the peaceful surroundings or entertaining guests, this home is a true gem. Don't miss your chance—More pictures to come,Not available for

  Darrell Tackett Dream Maker Realty, LLC

  4541 Colby Rd, Winchester, KY 40391
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  /14

  $292,000

  124 S Burns Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This duplex has a 3 bed 1 bath unit and a 3 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  124 S Burns Ave, Winchester, KY 40391
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  /3

  $221,000

  • 4 Beds
  • 2 Baths

  223 W Hickman St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This duplex has a 2 bed 1 bath unit and a 2 bed one bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  223 W Hickman St, Winchester, KY 40391
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  /9

  $274,000

  • 5 Beds
  • 3 Baths

  135 Winn Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This duplex has a 3 bed 2 bath unit and a 2 bed one bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  135 Winn Ave, Winchester, KY 40391
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  /34

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  37 7th St, Winchester, KY 40391

  Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

  Andrew Fugitt Coldwell Banker McMahan

  37 7th St, Winchester, KY 40391
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  /31

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,201 Sq Ft

  210 Moss Ct, Winchester, KY 40391

  Nice 3 bedroom, 2 bath, all one level, ranch home! Convenient location! Nice patio to sit out back in the mostly privacy fenced in yard. Only needs a few panels to be completely fenced if desired. One car garage. Easy to maintain lot. Large kitchen. Good sized bedrooms. Windows, HVAC, and roof all replaced within the last 8 years. This will make someone a great home!

  Jason Townsend Kentucky Residential Real Estate, LLC

  210 Moss Ct, Winchester, KY 40391
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  /32

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft

  116 Linden Ave, Winchester, KY 40391

  Welcome to 116 Linden Avenue located minutes from Winchester's charming downtown. This move in ready 3-bedroom, 2-bath home is complete with fresh paint and a great layout that offers both comfort and functionality. Enjoy the convenience of a first-floor primary bedroom and the bonus of a spacious yard, perfect for outdoor entertaining, gardening, or relaxing. Whether you're looking for your next

  Robert Bratton Bluegrass Sotheby's International Realty

  116 Linden Ave, Winchester, KY 40391
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  /27

  $278,900

  • 3 Beds
  • 3 Baths
  • 1,813 Sq Ft

  9 Hillcrest Dr, Winchester, KY 40391

  Built To Last, This Extra Solid Ranch Home, Was Built With Top Of The Line Materials! Turn It Into Your Dream Home Or Use As A Great Investment Property, Where As, You Can Easily Double Your Square Footage When Finishing The Basement. A Beautiful Layout, Offering 3 Bedrooms, 2 Full Baths, Chef's Kitchen, Separate Laundry, Off The Attached Garage, Open Concept Living & Dining Space, On The Main.

  Melissa Thompson Keller Williams Legacy Group

  9 Hillcrest Dr, Winchester, KY 40391
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  /14

  $265,000

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  10 Upper St, Winchester, KY 40391

  Modern Ranch residence full un-finished basement, large lot.

  E. Clark Toleman Real Estate Appraisal Services

  10 Upper St, Winchester, KY 40391
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  /47

  $259,000

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft

  17 Euclid Ave, Winchester, KY 40391

  Welcome to 17 Euclid Ave, a charming two-story home in the heart of Winchester! This beautifully maintained property features 3 bedrooms and 2 full baths, offering ample space and comfort. Enjoy the outdoors with a spacious deck perfect for relaxing or entertaining, surrounded by mature trees that provide shade and privacy. Convenient off-street parking ensures easy access, and the home's prime

  Donna Thwaites Thwaites Realtors® LLC

  17 Euclid Ave, Winchester, KY 40391
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  /46

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft

  7875 Bybee Rd, Winchester, KY 40391

  2021 Sout, Giles Double wide mobile home with 1616 square feet. Three bedrooms, 2 full baths. Primary bedroom has walk-in closet and the bath has a walk-in shower and double sink. In fact, all three bedrooms have walk-in closets. Range, dishwasher and refrigerator stay. There is a front porch and a covered deck on the back for your enjoyment. Mobile home has been attached to the land. Barn with

  Joyce Ratliff Tom Goebel & Company

  7875 Bybee Rd, Winchester, KY 40391
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  /38

  $285,000

  • 4 Beds
  • 2 Baths
  • 1,924 Sq Ft

  217 Morris Rd, Winchester, KY 40391

  OPEN HOUSE this Saturday (6/28) & Sunday (6/29) 2-4pm! This is The one You Have Been Waiting For! Room For The Whole Family In The Country But Within 5 Minutes Of The Interstate. This 4 Bedroom 2 Bathroom Home With A Living Room And Family Room/Den With Open Kitchen Has It All. Property Includes An Above Ground Swimming Pool, TinyHome/Shed That Has Plumbing Already Ran And Electric At The Pole

  Patrick Arvin Keller Williams Commonwealth

  217 Morris Rd, Winchester, KY 40391
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  $224,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  59 Holiday Rd, Winchester, KY 40391

  With limited inventory on the market, don't wait too long to view this brick ranch that offers comfort, updates, and a spacious outdoor area—all at an affordable price!This home features 3 bedrooms and 1 full bath, with fresh interior paint and newer laminate flooring for a clean, modern feel. The living spaces are filled with natural light, making the home feel warm and inviting from the

  Kathy Burton Coldwell Banker McMahan

  59 Holiday Rd, Winchester, KY 40391
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  /23

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  26 Stefanie Ct, Winchester, KY 40391

  Welcome to this charming 3BR-1BA brick ranch nestled in a quiet court in Winchester. The home features classic hardwood flooring throughout, offering timeless style and easy maintenance. Outback you will enjoy a fenced in yard and a detached 1 car garage. Don't miss the opportunity to own a move-in-ready gem. Call today for your showing.

  Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391
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  /57

  $362,000 Open Sun 12PM - 2PM

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

  356 Boone Ave, Winchester, KY 40391

  Your chance to live in a beautiful, renovated home on historic Boone Avenue. Walk to downtown, the public library or college park. This two-story home has loads of renovations and is ready for you to move right in. This home features 4 bedrooms and a bonus room, currently used as an office. The updated kitchen is a cooks dream! Granite counters and huge island, newer appliances and

  Nancy Smith Rector Hayden Realtors

  356 Boone Ave, Winchester, KY 40391
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  /31

  $174,900

  • 3 Beds
  • 1 Bath
  • 1,332 Sq Ft

  120 E Lexington Ave, Winchester, KY 40391

  Looking for an affordable home? Look no further than this recently updated 3 bedroom 1 bath with possible 4th bedroom or bonus room. New flooring, appliances, fixtures and new hvac. Replacement windows before current owner. Great starter home located convenient to downtown area and shopping.

  Chris Johnson Plum Tree Realty

  120 E Lexington Ave, Winchester, KY 40391
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  /37

  $1,249,500

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

  700 Nick Ln, Winchester, KY 40391

  🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you

  Darrell Tackett Dream Maker Realty, LLC

  700 Nick Ln, Winchester, KY 40391
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  /54

  $274,900

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  137 Sturbridge Ln, Winchester, KY 40391

  This lovely story and a half home is conveniently located close to Bypass road with easy access to everything Winchester has to offer. The main floor offers a comfortable living area that connects to the spacious eat-in kitchen, a convenient half bathroom, and the laundry room. Take a step out the back patio door to experience the generous, shaded, privacy fenced back yard perfect for kids or

  Josh Wood Freedom Realty & Property Mgt

  137 Sturbridge Ln, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 5

Why Live in Winchester

Winchester, KY, the largest city in Clark County, is known for its vibrant community and unique local flavors, including the birthplace of beer cheese and Ale-8-One soda. Main Street is the hub for dining, featuring popular spots like La Trattoria and Loma’s, and the Beer Cheese Trail, which includes around 15 restaurants with signature beer cheese recipes. The city offers practical amenities with nearby grocery stores like Kroger and Walmart Supercenter, and retail options such as TJ Maxx and Lowe’s. Housing in Winchester includes Victorian-era inspired homes and newer subdivisions, with properties often featuring gravel driveways and spacious lawns suitable for gardens. Clark County Public Schools provide strong academic programs, including AP and dual enrollment courses at George Rogers Clark High School. For outdoor activities, residents enjoy Legacy Grove Park, College Park, and Lykins Park, which offer facilities for basketball, tennis, hiking, and disc golf. Winchester hosts annual events like the Beer Cheese Festival and the Daniel Boone Pioneer Festival, attracting visitors with arts, crafts, and food. The Bluegrass Heritage Museum showcases the history of Central Kentucky. Commuting is convenient with Winchester located 16 miles from Lexington and 20 miles from Richmond. The city has a cooperative community spirit, bolstered by investments from younger residents and a thriving local economy.

Learn more about living in Winchester

Frequently Asked Questions

What is the average home price in Winchester, KY?

Homes for sale in Winchester, KY have an average home price of $342,677.

How many homes have sold over the last 12 months in Winchester, KY?

372 homes have sold in Winchester, KY over the last 12 months.

Is Winchester, KY a safe city?

In general, the safest neighborhoods in Winchester, KY with lower crime scores are Old Pine Grove, Becknerville and Wyandotte.

What are the most popular zip codes in Winchester, KY?

The most popular zip codes in Winchester, KY include 40391, 40361, 40353, 40516 and 40475.

What are the most popular neighborhoods in Winchester, KY?

The most popular neighborhoods in Winchester, KY with the most homes for sale are Old Pine Grove, Becknerville and Wyandotte.

How much do you need to make to afford a house in Winchester?

The median home price in Winchester is $275,000. If you put a 20% down payment of $55,000 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $1,420 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $61K a year to afford the median home price in Winchester.

How are the schools in Winchester, KY?

Winchester, KY has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Strode Station Elementary School, Baker Intermediate School and George Rogers Clark High School. The neighborhoods in Winchester with the highest rated schools are Old Pine Grove, Becknerville and Wyandotte. Browse all the schools in Winchester, KY to learn more.

Home Trends in Winchester, KY

On average, homes in Winchester, KY sell after 29 days on the market compared to the national average of 50 days. The median sale price for homes in Winchester, KY over the last 12 months is $248,500, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$248,500

Median Single Family Sale Price

$271,950

Median Townhouse Sale Price

$192,000

Average Price Per Sq Ft

$162

Number of Homes for Sale

104

Last 12 months Home Sales

372

Months of Supply

3.40

Median List Price

$275,000

Median Change From 1st List Price

3%

Median Home Sale Price YoY Change

4%