Winchester Homes for Sale

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  /23

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,319 Sq Ft

  3 Nunnelly Ct, Winchester, KY 40391

  Welcome to 3 Nunnelly Ct, Winchester, KY This charming 3-bedroom, 2-bathroom home offers comfortable living with several important updates already in place. Featuring a newer HVAC system and newer roof, this home provides peace of mind for its next owner while offering plenty of opportunity to make the space your own. Inside, you'll find a bright, inviting layout with fresh, neutral finishes,

  Yasir Ahmed Black Mountain Realty

  3 Nunnelly Ct, Winchester, KY 40391
• Explore Winchester

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  /32

  $175,000

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft

  24 Spring St, Winchester, KY 40391

  Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer

  Jason Szaks EXIT Town & Country Realtors

  24 Spring St, Winchester, KY 40391
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  /36

  $125,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  16 Denny Ave, Winchester, KY 40391

  Well priced and well located, 16 Denny Avenue is conveniently located near Eugene Gay Splash Park, downtown Winchester, shopping and schools. Home features 1152 sq ft with 3 bedrooms, 1 full bath, eat in kitchen and living room. Enclosed porch is located on front of house. Upgrades include laminate flooring, ductless heating and cooling and roof. Property has been tenant occupied and is sold as

  ROBIN TRIMBLE HomeFirst Real Estate

  16 Denny Ave, Winchester, KY 40391
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  /34

  $229,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,297 Sq Ft

  13 Long Ave, Winchester, KY 40391

  Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities.

  Kathryn Cheuvront Coldwell Banker McMahan

  13 Long Ave, Winchester, KY 40391
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  /19

  $205,400

  • 2 Beds
  • 1 Bath
  • 1,154 Sq Ft

  606 College St, Winchester, KY 40391

  606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom

  Jennifer Woods Marshall Lane Real Estate

  606 College St, Winchester, KY 40391
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  /27

  $270,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  15 Kittison Dr, Winchester, KY 40391

  Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and

  Cheri Shaffer Lifstyl Real Estate

  15 Kittison Dr, Winchester, KY 40391
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  /30

  $150,000

  • 2 Beds
  • 1 Bath
  • 630 Sq Ft

  108 Franklin Ave, Winchester, KY 40391

  Property includes a detached secondary structure, a 600 sq. ft., 1-bedroom, 1-bath. This structure offers potential for investment use. Property and secondary structure are being sold as-is. Buyer and buyer's agent to independently verify square footage, zoning, permitted use, occupancy requirements, and suitability for buyer's intended purpose.

  Cheri Shaffer Lifstyl Real Estate

  108 Franklin Ave, Winchester, KY 40391
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  /12

  $137,500

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  48 Judy Ann Ct, Winchester, KY 40391

  Affordable and inviting townhome conveniently located in Winchester! This well-maintained home offers a functional layout with a spacious kitchen featuring plenty of room for everyday cooking and dining. The main level includes a comfortable living room, convenient half bath, and access to a private patio, perfect for relaxing or enjoying your morning coffee. A dedicated storage area provides

  Holly Spradlin KY Realty Co

  48 Judy Ann Ct, Winchester, KY 40391
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  /110

  $724,889

  • 4 Beds
  • 4.5 Baths
  • 4,255 Sq Ft

  132 Lana Ln, Winchester, KY 40391

  This gorgeous home is a rare find. Perfect for anyone looking for a spacious home with room to grow. The beautiful sunroom overlooks the luxurious in-ground salt water pool. Inside the home you'll find over 4,000 square feet of easy living. A beautiful kitchen with a breakfast nook and bar top, a formal dining area, large living room, a family room with a fireplace, spacious bedrooms, and a

  Rebecca Harvey Napier Realtors

  132 Lana Ln, Winchester, KY 40391
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  /22

  $239,500

  • 3 Beds
  • 2 Baths
  • 1,130 Sq Ft

  527 Hidden Hills Way, Winchester, KY 40391

  NEW roof, NEW kitchen appliances, NEW deck, and more! Welcome to 527 Hidden Hills Way! Located on a quiet cul-de-sac, this renovated one level home is ready for you to move right in. Vaulted ceilings give an open and airy feel, while fresh paint throughout offers a neutral palette for any design style. The spacious kitchen includes plenty of oak cabinetry, a separate pantry, stainless steel

  Jarran Thomas The Agency

  527 Hidden Hills Way, Winchester, KY 40391
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  /23

  $194,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  143 Spruce Ct, Winchester, KY 40391

  Welcome to 143 Spruce Court in Winchester! This charming brick ranch offers comfortable one-level living with 3 bedrooms and 1 full bath. Inside, you'll find beautiful hardwood flooring and a warm, inviting layout. Outside, enjoy a well-manicured yard with plenty of space to relax or entertain. Conveniently located near a local park featuring a splash park and recreational amenities, this home

  John Wilson Bluegrass Properties Group

  143 Spruce Ct, Winchester, KY 40391
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  /31

  $300,000

  • 4 Beds
  • 2 Baths
  • 2,479 Sq Ft

  224 W Hickman St, Winchester, KY 40391

  Classic character and generous living space come together at 224 W Hickman Street in Winchester. This single-family residence offers 4 bedrooms, 2 full bathrooms, and approximately 2,479 square feet, providing a flexible layout with room for a variety of everyday living needs. The home's substantial interior footprint creates opportunities for comfortable gathering spaces, private bedrooms, a

  Bob Sophiea eXp Realty, LLC

  224 W Hickman St, Winchester, KY 40391
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  /31

  $455,000

  $50K PRICE DROP

  • 8 Beds
  • 4 Baths
  • 5,058 Sq Ft

  265 S Highland St, Winchester, KY 40391

  Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8

  J Corey Griffo RE/MAX Elite Lexington

  265 S Highland St, Winchester, KY 40391
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  /28

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,665 Sq Ft

  106 Quail Ridge Rd, Winchester, KY 40391

  This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location

  Mila Ensor Ensor Real Estate, LLC

  106 Quail Ridge Rd, Winchester, KY 40391
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  /24

  $280,000

  $20K PRICE DROP

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

  209 Boone Ave, Winchester, KY 40391

  Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a

  Todd Hyatt Lois Ann Disponett Real Est

  209 Boone Ave, Winchester, KY 40391
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  /24

  $365,900

  New Construction $4K PRICE DROP

  • 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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  /27

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,108 Sq Ft

  227 Leslie Dr, Winchester, KY 40391

  This 3 Bedroom, 2 bath home is quietly nestled within the Saddle Brook subdivision. Conveniently located just outside of Winchester New Bypass, this property also qualifies for zero down rural housing financing. Updates can be seen throughout along with spacious master bedroom with on-suite, large back yard and open concept living. Schedule your showing today!

  Michael Hilario The Agency

  227 Leslie Dr, Winchester, KY 40391
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  /40

  $299,900

  $6K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft

  428 Waycross Dr, Winchester, KY 40391

  Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and

  Wayne Elkins RE/MAX Creative Realty

  428 Waycross Dr, Winchester, KY 40391
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  /32

  $199,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  32 Jackson St, Winchester, KY 40391

  This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.

  Dale Hatton Dream Maker Realty, LLC

  32 Jackson St, Winchester, KY 40391
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  /4

  $389,900

  • 9 Beds
  • 6 Baths
  • 1,116 Sq Ft

  341 Carolina Ave, Winchester, KY 40391

  Exceptional investment opportunity! This fully occupied triplex is a turnkey addition to any investment portfolio, offering three spacious units, each with approximately 1,116 square feet, 3 bedrooms, and 1.5 bathrooms. With strong rental potential and separately metered utilities paid by the tenants, this property provides an excellent income-producing opportunity. Each unit features a

  Erin Lewis Christies International Real Estate Bluegrass

  341 Carolina Ave, Winchester, KY 40391
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  /12

  $495,000

  $34K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,054 Sq Ft

  443 Oxford Dr Unit 443,445,447,449, Winchester, KY 40391

  Don't miss this rare quadruplex opportunity in Winchester. Featuring four units (443, 445,447 and 449 Oxford Drive), this property is perfect for investors seeking multiple income streams in one location. Each unit offers a similar layout with approximately 1,054 ft, 2 bedrooms, and 1.5 baths. The photos shown are from one updated unit, and all units have comparable layouts—making this an ideal

  Tracey Goebel Tom Goebel & Company

  443 Oxford Dr Unit 443,445,447,449, Winchester, KY 40391
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  /45

  $272,900

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  316 Buffalo Trace, Winchester, KY 40391

  Welcome home to this beautifully maintained 3 bedroom, 2 bath home offering comfort, style and fantastic outdoor living! The spacious two-car garage provides plenty of room for parking and storage, while the fully fenced backyard with a new privacy fence creates the perfect space to relax or entertain. Step outside to enjoy the inviting covered outdoor entertaining area, complete with lighting

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  316 Buffalo Trace, Winchester, KY 40391
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  /55

  $410,000

  $5K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 3,306 Sq Ft

  351 Boone Ave, Winchester, KY 40391

  Classic Williamsburg inspired home with charming dormers, timeless character, and an exceptional location that's a short walk to historic downtown Winchester. This spacious 4-bedroom , 2 bath home offers a flexible floor plan with 2 main-level bedrooms and a full bath, plus two additional bedrooms and a full bath upstairs. Enjoy elegant formal living and dining rooms, a large home office, and a

  Jim Woodrum RE/MAX Creative, Winchester

  351 Boone Ave, Winchester, KY 40391
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  /12

  $239,000

  $116K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,072 Sq Ft

  1128 Dale Dr, Winchester, KY 40391

  Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
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  /37

  $259,000

  $37K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  33 Bon-Haven Ave, Winchester, KY 40391

  Welcome home to this beautifully renovated home in the desirable Bon Haven subdivision! From the moment you step inside, you'll appreciate the bright and inviting living room that flows seamlessly into the updated kitchen, creating a warm and functional space for everyday living. The main level features two spacious bedrooms and two full bathrooms, while the second floor offers a private third

  Erika Beatty Plum Tree Realty

  33 Bon-Haven Ave, Winchester, KY 40391
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  /50

  $229,900

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

  491 Hidden Hills Way, Winchester, KY 40391

  Welcome home to this charming 3-bedrooms, 2-bath ranch perfectly situated in the heart of Winchester! Offering the convenience of one-level living, this inviting 1200 sq ft home combines comfort, functionality, and an unbeatable location. Primary bedroom is en suite and offers plenty of closet space. Additional 2-bedrooms and 1-bath provide plenty of space. Enjoy easy access to schools, shopping,

  ROBIN TRIMBLE HomeFirst Real Estate

  491 Hidden Hills Way, Winchester, KY 40391
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  /41

  $225,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,609 Sq Ft

  120 Windsor Dr, Winchester, KY 40391

  Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful

  Cathie Witt-Pyle Keller Williams Commonwealth

  120 Windsor Dr, Winchester, KY 40391
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  /30

  $299,900

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,840 Sq Ft

  209 Connie Ln, Winchester, KY 40391

  Very motivated sellers, Get here first, make an offer on this 4 bedroom, 3 bath, 1 1/2 story home, 2 car garage, showroom fresh condition, vaulted ceiling, hardwood floors, tile, carpet, deck, nice back yard, call today to view.

  Mila Ensor Ensor Real Estate, LLC

  209 Connie Ln, Winchester, KY 40391
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  /4

  $159,000

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,472 Sq Ft

  13 Maryland Ave, Winchester, KY 40391

  Welcome Home! Located across the street from a park with walking trails and 2 dog runs, this home is ready for a new owner. Featuring 2 bedrooms on the first floor and an optional 3rd bedroom or bonus room in the partially finished attic space. The original hardwood floors are located throughout the home. VA assumable loan with a 2.99% interest rate - you can't beat that in today's market! Home

  Clay David Sutherland ERA Select Real Estate

  13 Maryland Ave, Winchester, KY 40391
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  /31

  $89,900

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft

  308 Market St, Winchester, KY 40391

  Newly built and ready for its first owner, this 2-bedroom, 2-bathroom home in Quick Shop delivers the layout and finishes most buyers want without the price tag of new site-built construction. The main living area opens directly into the kitchen, giving the space a connected, airy feel that suits quiet evenings and gatherings alike. Down the hall, 2 bedrooms are sized for real furniture and real

  Hailey Blaylock Quick Shop MHC

  308 Market St, Winchester, KY 40391
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  /9

  $500,000

  $100K PRICE DROP

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
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  /7

  $270,000

  $50K PRICE DROP

  • Land
  • 36,590 Sq Ft
  • $321,429 per Acre

  800 Interstate Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

  Whitney Ensor Ensor Real Estate, LLC

  800 Interstate Dr, Winchester, KY 40391
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  /43

  $319,900

  Open Sat 1PM - 3PM $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft

  8 Monroe Ave, Winchester, KY 40391

  If you love to entertain and are looking for a cozy home that is move in ready, you don't want to let the one pass you by! Includes 3 bedrooms and two full baths this home has it all. Equipped with a primary bedroom suite with spacious bathroom and walk in closet. This home has beautiful hardwood floors in kitchen living and dining areas. In the gallery kitchen you will find granite countertops,

  Lisa Barker Freedom Realty & Property Management

  8 Monroe Ave, Winchester, KY 40391
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  /27

  $149,900

  $3K PRICE DROP

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

  65 Fitch Ave, Winchester, KY 40391

  Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS",

  Mila Ensor Ensor Real Estate, LLC

  65 Fitch Ave, Winchester, KY 40391
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  /14

  $650,000

  • Land
  • 3 Acres
  • $216,667 per Acre

  205 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Homes

  205 Codella Dr, Winchester, KY 40391
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  /13

  $400,000

  • Land
  • 2.19 Acres
  • $182,648 per Acre

  145 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Homes

  145 Codella Dr, Winchester, KY 40391
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  /25

  $221,500

  $8K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,454 Sq Ft

  2 Western Ave, Winchester, KY 40391

  MOTIVATED SELLER!! Don't miss this wonderful home offering convenience, comfort, and value!! Ideally situated near shopping, dining, schools, churches and everyday amenities. This property is perfect for first-time buyers or downsizers. The backyard provides ample space for entertaining is completely fenced in for children and pets. Home also provides room to grow. The attic space has plenty of

  A. Rebecca Woods Woods Realty Group

  2 Western Ave, Winchester, KY 40391
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  /46

  $229,000

  $18K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  30 Virginia Ave, Winchester, KY 40391

  Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  30 Virginia Ave, Winchester, KY 40391
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  /16

  $124,500

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  122 Calloway St, Winchester, KY 40391

  Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

  Darrell Tackett Dream Maker Realty, LLC

  122 Calloway St, Winchester, KY 40391
• 

  

  /37

  $219,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,261 Sq Ft

  14 Cook Ave, Winchester, KY 40391

  Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a

  Janna Chalfant Smith United Real Estate Bluegrass

  14 Cook Ave, Winchester, KY 40391

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