Winchester, KY Houses for Sale

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  /67

  $699,000

  • 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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  Explore Winchester

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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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  /82

  $440,000

  • 4 Beds
  • 3.5 Baths
  • 2,637 Sq Ft

  397 Calmes Blvd, Winchester, KY 40391

  This stunning, renovated home is move-in ready and packed with upgrades that make it an absolute must-see! Step inside and enjoy the fresh, modern feel of the newly painted interior, with updated flooring throughout—including brand-new flooring in the basement, kitchen, and upstairs hall, along with plush new carpet on the upper level. The two remodeled bathrooms feature sleek finishes that add a

  Omar Shalash Tru Life Real Estate

  397 Calmes Blvd, Winchester, KY 40391
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  /71

  $419,000

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  188 Big Stoner Rd, Winchester, KY 40391

  48 hr kick-out- Come home every day to this 2-story beauty! You need country life? Well here is it! A little over 1 acre to spread out & enjoy the outdoors w/farm views & beautiful sunsets in the evening. This home opens up to a huge living room with hardwood floors and a vaulted ceiling. Kitchen has all stainless steel appliances & granite counter tops. First floor has a primary suite

  Trina Penn RE/MAX Creative Realty

  188 Big Stoner Rd, Winchester, KY 40391
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  /102

  $547,900

  • 6 Beds
  • 4.5 Baths
  • 3,846 Sq Ft

  1953 Cabin Creek Rd, Winchester, KY 40391

  ***Click on the Virtual Tour section to see the video walk through!*** This unique property includes not only one, but two beautiful homes in the heart of Kentucky Bluegrass country. The first home is a brick ranch with a covered front porch and back patio that overlook this beautiful piece of farm land. This 2046 sq ft home contains 3 bedrooms and 2 full baths with a large great room in the

  Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
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  /67

  $539,000

  • 4 Beds
  • 2.5 Baths
  • 3,989 Sq Ft

  415 David Ln, Winchester, KY 40391

  Location, location, location!! This house, 415 David Lane, is located in the most sought after neighborhood, Stoneybrook. It is approximately 20 minutes from the Hamburg area of Lexington and minutes from the I-75 corridor. Enter the house from the welcoming front porch to a entryway and notice immediately the gleaming hardwood floors and the stairway leading to the second floor. The primary

  Craig Bridgewater Bridgewater Real Estate

  415 David Ln, Winchester, KY 40391
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  /64

  $440,000

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  1857 Ironworks Rd, Winchester, KY 40391

  Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acres in Clark County. Dreaming of the country life? This is it, originally built in 1865 this timeless home has been completely updated and seamlessly blended the history with modern elegant design and livability. Classic farmhouse style with tons of natural light that bring the outside in. Spacious great room

  Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
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  /53

  $470,000

  • 4 Beds
  • 3 Baths
  • 2,844 Sq Ft

  129 Lana Ln, Winchester, KY 40391

  Open House -Sunday 1-3 p.m.! Stunning renovated 4-BR,3BA brick ranch with walkout basement, in-ground pool & pool house! This home has undergone extensive remodeling to improve traffic flow while preserving distinct living spaces. These updates create a seamless and intuitive flow through, enhancing both functionality and style! Recent Improvements and Updates-fully remodeled kitchen, bathrooms,

  Jo Gawthrop Keller Williams Bluegrass Realty

  129 Lana Ln, Winchester, KY 40391
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  /57

  $630,000

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

  670 Lillies Ferry Rd, Winchester, KY 40391

  Escape to this serene and private 12+ acre property, boasting a 3BR/2BA home sitting on a partially finished walkout basement, that provides ample space for a home office, playroom, or additional living area. This charming home has lots of recent upgrades, including a brand new HVAC system, ensuring a comfortable living space year-round. The exterior of the home has been upgraded with new

  Jennifer Helton EXP Realty, LLC

  670 Lillies Ferry Rd, Winchester, KY 40391
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  /9

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft

  508 Boone Ave, Winchester, KY 40391

  3 bedroom, 2 1/2 bath brick home in Witherspoon Subdivision. Full basement with double space garage. Spacious formal living room and separate formal dining room. Great room includes breakfast area and sitting area. Large master ensuite includes closet with plenty of storage space. Close to schools, shopping and dining. Convenient to Lexington, Richmond and Paris.

  Donna C. Slone-Crumbie Wright Realty

  508 Boone Ave, Winchester, KY 40391
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  /36

  $409,999

  • 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 reimagined with a rear addition, this residence now boasts a spacious first-floor primary suite featuring a private en-suite bathroom, walk-in closet, and convenient laundry access.Each of the four bedrooms includes its own private bath, offering exceptional comfort and

  Ellie Hatton The Brokerage

  136 College St, Winchester, KY 40391
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  /39

  $629,900

  • 4 Beds
  • 5 Baths
  • 4,374 Sq Ft

  600 Boone Ave, Winchester, KY 40391

  Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

  Holly Goeing The Agency

  600 Boone Ave, Winchester, KY 40391
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  /58

  $365,000

  • 4 Beds
  • 2.5 Baths
  • 2,179 Sq Ft

  205 Chardonnay Ct, Winchester, KY 40391

  This charming 4-bedroom, 2.5-bath home with a classic white picket fence sits on a quiet cul-de-sac in Fontaine Estates. Inside, the versatile layout offers space for every occasion—a formal dining room for special gatherings, a bright sunroom for morning coffee, a comfortable living room, and a cozy family room featuring a masonry fireplace with built-ins. The eat-in kitchen is perfect for

  Janna Smith United Real Estate Bluegrass

  205 Chardonnay Ct, Winchester, KY 40391
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  /27

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft

  5705 Mount Sterling Rd, Winchester, KY 40391

  The one you've been waiting for. This beautiful home has so much to offer. 4 bedrooms, 2 1/2 bathrooms, with full basement and mother in law suite. It sits on just over 3 spacious acres. There is a 24X36 work shop just built in 2022. The roof and HVAC are just 6 years old. The water heater is 6 months old. The property has 10 beautiful apple trees and 3 pear trees. The home is just minutes from

  Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
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  /36

  $360,000

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  208 Citation Ct, Winchester, KY 40391

  One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under. (see photos) Kitchen appliances include

  Garnett Davis Tom Goebel & Company

  208 Citation Ct, Winchester, KY 40391
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  /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
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  /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
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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

  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

  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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  /17

  $445,000

  • 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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  /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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  /64

  $369,900 New Construction

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

  309 Gallahadion Ct, Winchester, KY 40391

  This beautiful, new-construction 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. The builder has installed window blinds throughout the home and stained the back deck. Don't miss the primary

  Josh Wood Freedom Realty & Property Management

  309 Gallahadion Ct, 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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  /88

  $849,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 3.5 Baths
  • 4,345 Sq Ft

  1701 Gay Evans Rd, Winchester, KY 40391

  Your dream country retreat awaits! Nestled on 8+ scenic acres, this stunning brick ranch offers the perfect blend of modern efficiency, functional living space, and peaceful country charm. A brand-new geothermal heating and cooling system ensures year-round comfort and energy savings, giving you confidence in your home's efficiency for years to come.The main level boasts a spacious primary

  Nora Williams Keller Williams Commonwealth

  1701 Gay Evans Rd, Winchester, KY 40391
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  /21

  $149,000

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
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  /26

  $215,000

  • 3 Beds
  • 2.5 Baths
  • 1,224 Sq Ft

  388 Colby Ridge Blvd, Winchester, KY 40391

  Need to see inside of this one! Seller bought in May 2021. Remodeled kitchen. Removed one wall between kitchen and living room. Installed a granite bar/island and countertops. Installed all new kitchen cabinets. Installed all new stainless steel appliances (including a top-of-the-line Kitchen Aid dishwasher). Put in deep sink and garbage disposal. Pantry cabinet beside refrigerator.

  Joyce Ratliff Tom Goebel & Company

  388 Colby Ridge Blvd, Winchester, KY 40391
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  /20

  $159,900

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  103 Yorktowne Ct, Winchester, KY 40391

  Affordable and move-in ready! This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping, dining, and easy access to I-64 while still tucked away on a quiet

  Susy Esquivel Allied Realty

  103 Yorktowne Ct, Winchester, KY 40391
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  /22

  $269,900

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  115 Ashley Dr, Winchester, KY 40391

  Well maintained 3 bedroom 2 bath ranch with a fenced in backyard and 2 car garage on a very desirable street! All one level! Not a single step on the entire property! Double driveway plus street parking! Open concept living / dining area connects to an enclosed sunroom on the back. Just minutes from shopping, dining, and the interstate. Third bedroom is non-conforming due to not having an egress

  Jason Townsend Kentucky Residential Real Estate, LLC

  115 Ashley Dr, Winchester, KY 40391
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  /27

  $220,000

  • 3 Beds
  • 1.5 Baths
  • 1,209 Sq Ft

  7 Lisle Ln, Winchester, KY 40391

  Nestled on a picturesque tree-lined street, this beautifully updated home offers easy access to the country club, library, parks, and schools. Step inside to a bright, open living area highlighted by a wood-burning fireplace—perfect for cozy fall evenings.The remodeled kitchen features new cabinets, countertops, and appliances, while the main bathroom has been refreshed with modern

  Steve Charles Freedom Realty & Property Management

  7 Lisle Ln, Winchester, KY 40391
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  /33

  $170,000

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft

  646 Laura Dr, Winchester, KY 40391

  Ranch style home located in Verna Hills just across the Scott County line off Winchester Road. Home features four bedrooms, two full baths, eat in kitchen with laundry closet, primary bedroom with adjoining bath, Hall guest bathroom and large guest bedroom on the right side of the home. Backyard is fenced and has a large deck. Case # 201-735718 Insured with Escrow.

  Kimberly Brunson Hunter Real Estate

  646 Laura Dr, Winchester, KY 40391
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  /64

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft

  113 Olde Potomac Ave, Winchester, KY 40391

  This phenomenal property has had so many updates including the addition of a full bath on the second floor, an updated electric panel, new wiring throughout, added electrical outlets, all new plumbing, a heat pump for the second floor (there is gas heat on the first floor) and a walk-in closet in the primary bedroom on the first floor. The owners have given meticulous attention to every

  Susan Colwell Colwell Realty Professionals, Inc.

  113 Olde Potomac Ave, Winchester, KY 40391
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  /13

  $185,000

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  220 Pendleton St, Winchester, KY 40391

  Fully renovated home with new exterior vinyl walls and dimensional shingle rood. Interior has received new insulation, drywall, all new wiring, partial windows, new appliances and counters, new bathroom vanity/tub/toilet, new LVP floor coverings, new interior/exterior doors, new heat pump/water heater.

  Steve Adams Steven D Adams Real Estate Services, LLC

  220 Pendleton St, Winchester, KY 40391
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  /36

  $285,000

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft

  103 Hampton Ave, Winchester, KY 40391

  A timeless brick ranch in one of Winchester's most established neighborhoods on a corner lot. This 3 bedroom, 2.5 bath home offers two living areas and a cozy fireplace. Spacious backyard, covered front porch, and a wrap-around driveway for a private entrance. All just minutes from downtown, schools, and I-64. The home combines classic comfort, location, and room to grow on a walk-out basement.

  Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
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  /98

  $824,900

  • 6 Beds
  • 5 Baths
  • 4,843 Sq Ft

  3900 Mount Sterling Rd, Winchester, KY 40391

  More pictures coming! This extraordinary home located on 8.4 acres and nestled back from the main road, offers spectacular views from both the front and rear and those views can be enjoyed from the expansive covered front porch or the extra-large covered back porch. As you arrive, the meticulous care taken to maintain the property is apparent. Inside, discover a beautifully updated kitchen, five

  Teresa Richmond Freedom Realty & Property Management

  3900 Mount Sterling Rd, Winchester, KY 40391
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  /34

  $299,000

  • 4 Beds
  • 3 Baths
  • 1,850 Sq Ft

  20 Bon-Haven Ave, Winchester, KY 40391

  Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers alike.Step inside to find a bright and airy open floor plan, highlighted by brand-new plumbing and

  Jacqueline Marchildon Lifstyl Real Estate

  20 Bon-Haven Ave, Winchester, KY 40391
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  /43

  $239,700

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  2413 Log Lick Rd, Winchester, KY 40391

  Charming 3 bedroom, 1 bath home situated on 1.8 acres in a peaceful country setting. This property offers plenty of space for horses, chickens, gardening, or an orchard, with an attached lean-to that can easily be converted into a horse stall. Enjoy scenic views from both the front and back porches. Recent updates include a brand-new roof, newer heat pump, new HVAC vent, fresh paint, and bamboo

  E Anthony Phillips RE/MAX Creative Realty

  2413 Log Lick Rd, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 3

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

Home Trends in Winchester, KY

On average, homes in Winchester, KY sell after 30 days on the market compared to the national average of 52 days. The median sale price for homes in Winchester, KY over the last 12 months is $242,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$242,000

Median Single Family Sale Price

$262,750

Median Townhouse Sale Price

$194,000

Average Price Per Sq Ft

$160

Number of Homes for Sale

82

Last 12 months Home Sales

318

Months of Supply

3.10

Median List Price

$263,500

Median Change From 1st List Price

3%

Median Home Sale Price YoY Change

1%