Winchester, KY Homes

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  /37

  Est $279,485 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,853 Sq Ft

  120 Milwood Dr, Winchester, KY 40391

  120 Milwood Dr, Winchester, KY 40391
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  /29

  $252,500 Pending

  • 4 Beds
  • 2 Baths
  • 1,593 Sq Ft

  306 Snowden Dr, Winchester, KY 40391

  Home is quietly nestled within the Wesleyan Park subdivision just off the Winchester Bypass. While convenient location is obvious this home boast many updates throughout. Including flooring, appliances, New roof, HVAC, Water heater and so much more. Schedule your showing while you can!

  Michael Hilario The Agency

  306 Snowden Dr, Winchester, KY 40391
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  /27

  $190,000 Sold Apr 18, 2025

  • 1,550 Sq Ft
  • $123/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1969

  7 Pocahontas Trail, Winchester, KY 40391

  Step inside this raised ranch, sun filled rooms, hardwood in most of the upstairs, kitchen with all the appliances, washer/dryer stay, large detached garage, hot tub on covered deck, great space in back yard, some fencing, lovely home close to historic downtown Winchester, not far from I-75 and I-64, shopping, church, schools, large partial finished walkout basement, call today this one won't

  Mila Ensor Ensor Real Estate, LLC

  7 Pocahontas Trail, Winchester, KY 40391
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  /48

  Est $247,197 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,496 Sq Ft

  132 Boone Ave, Winchester, KY 40391

  132 Boone Ave, Winchester, KY 40391
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  /26

  $224,900 Pending

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

  34 N Burns Ave, Winchester, KY 40391

  Welcome to 34 N Burns Avenue, a classic Winchester home with plenty of charm and thoughtful updates. Step inside to find a warm and inviting layout that balances comfort with functionality. The living spaces are filled with natural light, creating an easy flow whether you're relaxing at home or gathering with friends and family.The kitchen offers plenty of room for meal prep and everyday

  Ashley Barreto Indigo & Co

  34 N Burns Ave, Winchester, KY 40391
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  /87

  $250,000 Sold Apr 18, 2025

  • 1,680 Sq Ft
  • $149/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1996

  418 Jameson Way, Winchester, KY 40391

  Welcome to this charming split-level home in Maple Ridge subdivision! Designed with comfort and convenience in mind, this home features an updated eat-in kitchen with granite countertops, an all purpose kitchen island that fits 2 barstools and a stylish tiled backsplash. All bedrooms are on the first level, complete with your very own primary bathroom. The inviting living room offers a cozy

  Josh Wood Freedom Realty & Property Management

  418 Jameson Way, Winchester, KY 40391
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  /39

  Est $363,937 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,660 Sq Ft

  14 Euclid Ave, Winchester, KY 40391

  14 Euclid Ave, Winchester, KY 40391
• 

  

  /42

  $619,000 Pending

  • 6 Beds
  • 3.5 Baths
  • 5,227 Sq Ft

  439 Lynnway Dr, Winchester, KY 40391

  Welcome to 439 Lynnway, an expansive 5,000+ sq ft home, where every inch was designed for comfort, style, and entertainment. The main floor features a primary en-suite, office space, and laundry area. As you make your way upstairs, you will find spacious bedrooms throughout. New roof placed early 2025.The finished basement is a standout, offering the ultimate experience with an in home

  Reagan Rainey Dream Maker Realty, LLC

  439 Lynnway Dr, Winchester, KY 40391
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  /49

  $442,500 Sold Apr 18, 2025

  • 3,882 Sq Ft
  • $114/SF
  • 134 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 2005

  321 Frontier Way, Winchester, KY 40391

  OPEN HOUSE Saturday 3/1/25 2-4pm. Apart from home being in a great location, right across the street from the Elementary School, home is minutes from shopping, food and entertainment (Applebees,Woody's Bar and Grill, Tjmaxx, Kroger, Movie Theatre, Ft. Boonesborough) & only a 20 minute drive to Hamburg in Lexington or 15 miutes to Mt. Sterling. This beautiful home is complete with a newly

  Olivia White Deborah Ball Realty

  321 Frontier Way, Winchester, KY 40391
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  /40

  Est $231,549 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft

  313 S Burns Ave, Winchester, KY 40391

  313 S Burns Ave, Winchester, KY 40391
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  /63

  $439,500 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,921 Sq Ft

  259 Hibiscus Ln, Winchester, KY 40391

  IT'S YOUR LUCKY DAY! Due to no fault of the home or sellers, this beauty is BACK ON THE MARKET! This beautiful home blends comfort, space, & charm in a quiet, family-friendly neighborhood.The main level offers a generous living room w/ cozy fireplace for relaxed gatherings, a formal dining room is perfect for special occasions, while the spacious kitchen offers a pantry & casual dining

  Janna Smith United Real Estate Bluegrass

  259 Hibiscus Ln, Winchester, KY 40391
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  /2

  $110,000 Sold Apr 18, 2025

  • Land
  • 0.59 Acre
  • $186,441 per Acre

  • 847 Days On Market

  210 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  210 Duclair Dr, Winchester, KY 40391
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  /54

  Est $255,957 Not Listed For Sale

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

  17 Euclid Ave, Winchester, KY 40391

  17 Euclid Ave, Winchester, KY 40391
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  /33

  $299,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,760 Sq Ft

  314 Hanover Dr, Winchester, KY 40391

  Your search is over with this beautiful 3 bedroom 2 bath home with lots of potential. Enter into the 2-story foyer and enjoy the Great Room with overlooking loft. Home has large 1st floor Primary Bedroom with two additional bedrooms on the second floor. There is an option for a second family room or 4th bedroom as well. You will love the 2-car garage, back patio w/hot tub and the large Privacy

  Keith Wilson Coldwell Banker McMahan

  314 Hanover Dr, Winchester, KY 40391
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  /34

  $260,000 Sold Apr 17, 2025

  • 1,565 Sq Ft
  • $166/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  597 Marseille Blvd, Winchester, KY 40391

  Welcome to this 3-bedroom, 2-bathroom ranch-style home conveniently located off McClure Road in a desirable neighborhood, perfect for those looking to create their dream space. The layout features a spacious yet cozy living area with a fireplace and a functional kitchen, ready for your personal touch. Step outside to a large fenced backyard that's perfect for outdoor activities, pets, or

  Michelle Blackburn RE/MAX Creative, Winchester

  597 Marseille Blvd, Winchester, KY 40391
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  /32

  Est $257,016 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,893 Sq Ft

  13 Euclid Ave, Winchester, KY 40391

  13 Euclid Ave, Winchester, KY 40391
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  /69

  $284,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  227 Cross Brook Ln, Winchester, KY 40391

  This beautifully maintained brick ranch offers the perfect blend of comfort and convenience—all on one level. Featuring 3 bedrooms and 2 full baths, the open great room is anchored by durable LVP flooring installed in 2017 and flows seamlessly into a spacious kitchen with abundant cabinets, counter space, and a center island for casual seating. The dining area opens to a covered and partially

  Josh Wood Freedom Realty & Property Management

  227 Cross Brook Ln, Winchester, KY 40391
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  /17

  $390,000 Sold Apr 16, 2025

  • 1,854 Sq Ft
  • $210/SF
  • 73 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1983

  3750 Becknerville Rd, Winchester, KY 40391

  Are you longing for a quiet country home? A place to have a few farm animals, raise a garden and enjoy the peacefulness of living away from town. Presenting to you 3750 Becknerville Road. It checks all of the boxes! This lovely 5.5 acre mini farm is situated between Winchester and Lexington on a gorgeous, partially fenced tract, with amazing mature trees. With roughly 1850 square feet of living

  Holly Goeing The Agency

  3750 Becknerville Rd, Winchester, KY 40391
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  /43

  Est $337,313 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,513 Sq Ft

  201 Boone Ave, Winchester, KY 40391

  201 Boone Ave, Winchester, KY 40391
• 

  

  /40

  $225,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,699 Sq Ft

  5620 Ironworks Rd, Winchester, KY 40391

  Enjoy country living with a short commute to town! This 3 bedroom, 2 bath ranch also features a dedicated office that can be used as a 4th bedroom if needed, providing flexible living options. Inside, you'll find a cozy family room with a wood-burning fireplace. The eat-in kitchen features a pass-through window and bar seating, making an open connection to the living room. Situated on just over

  Michelle Blackburn RE/MAX Creative, Winchester

  5620 Ironworks Rd, Winchester, KY 40391

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