Winchester Homes for Sale

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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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  /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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  /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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  /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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  /40

  $289,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,692 Sq Ft

  54 Locust Dr, Winchester, KY 40391

  Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a

  Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  54 Locust Dr, Winchester, KY 40391
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  /36

  $265,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  20 Jackson St, Winchester, KY 40391

  Beautifully updated and truly move-in ready, this 3-bedroom, 2-bath home blends timeless charm with modern convenience. Step inside to a spacious living room and an updated kitchen featuring abundant cabinetry, while original hardwood flooring, luxury vinyl plank, and stylish finishes create a warm and inviting atmosphere throughout. The versatile utility room provides the perfect space for a

  Zova Rothchild Keller Williams Legacy Group

  20 Jackson St, 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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  /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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  /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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  /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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  /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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  /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
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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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  /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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  /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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  /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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  /30

  $329,900

  $20K PRICE DROP

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

  410 W Lexington Ave, Winchester, KY 40391

  Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for

  Tracy Ison Bluegrass Home Group

  410 W Lexington Ave, 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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  /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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  /41

  $329,900

  $10K PRICE DROP

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

  23 Windridge Dr, Winchester, KY 40391

  Welcome home to Windridge!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family

  Holly Goeing The Agency

  23 Windridge Dr, Winchester, KY 40391
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  /6

  $299,000

  $151K PRICE DROP

  550 E Broadway St, Winchester, KY 40391

  Prime land located on the outskirts of Winchester ready for possible development. Parcel has frontage on both East Broadway and Washington Street. Land is currently zoned A-1. Utilities available. The future awaits!!!

  Keith Wilson Coldwell Banker McMahan

  550 E Broadway St, 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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  /29

  $279,999

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  103 Southern Ct, Winchester, KY 40391

  Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

  Mila Ensor Ensor Real Estate, LLC

  103 Southern Ct, 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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  /49

  $445,500

  • 3 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

  Markus Cross McCallie Real Estate

  42 Mockingbird Valley Rd, Winchester, KY 40391

Showing Results 41 - 67, Page 2 of 2