Winchester, KY Homes

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  /103

  $2,995,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 10-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /37

  $207,000 Sold May 23, 2025

  • 1,120 Sq Ft
  • $185/SF
  • 41 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  632 Laura Dr, Winchester, KY 40391

  Discover the perfect blend of comfort and convenience in this charming 3-bedroom home, nestled in a sought-after neighborhood. Boasting a spacious fenced-in backyard, it's an ideal retreat for privacy and outdoor enjoyment. This gem offers a harmonious balance of community feel and personal sanctuary. Welcome to your dream home where memories await!'

  Dale Hatton Dream Maker Realty, LLC

  632 Laura Dr, Winchester, KY 40391
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  /53

  Est $274,530 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,170 Sq Ft

  214 S Burns Ave, Winchester, KY 40391

  214 S Burns Ave, Winchester, KY 40391
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  /17

  $195,000

  • 3 Beds
  • 1 Bath
  • 1,059 Sq Ft

  114 Sunset Heights, Winchester, KY 40391

  Conveniently located, well maintained ranch with 3 bedrooms in established neighborhood, awaiting its new owner! With a newer roof, gutters (with guards), furnace and water heater...it helps take some maintenance worries away! Ample storage with storage closet in carport, and detached shed. Three hundred sq.ft. 3-seasons area in rear of home, which could be used year-round with the addition of a

  Susan Baldwin Rector Hayden Realtors

  114 Sunset Heights, Winchester, KY 40391
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  /82

  $275,000 Sold May 23, 2025

  • 2,994 Sq Ft
  • $92/SF
  • 202 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1920

  111 S Burns Ave, Winchester, KY 40391

  Reduced for quick sale!! Don't miss out on your opportunity to own a 100+ year old home located near historic downtown Winchester, KY. The detail and charm located within the walls of this 2 story craftsman are what many dream of. Tall ceilings, fireplaces, in almost evey room, beautiful original wood work is abundant as you enter from the quintessential front porch that's perfect for casual

  Melodie Lincavage RE/MAX Elite Realty

  111 S Burns Ave, Winchester, KY 40391
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  /16

  Est $199,260 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  227 W Broadway St, Winchester, KY 40391

  227 W Broadway St, Winchester, KY 40391
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  /52

  $549,900

  • 4 Beds
  • 2 Baths
  • 2,940 Sq Ft

  5515 Van Meter Rd, Winchester, KY 40391

  Welcome to your dream home, perfectly nestled in a highly desired location. This stunning property spans a generous 5 acres, offering an idyllic setting for homesteading. Experience the best of country living with the convenience of nearby amenities.The home boasts beautiful views that will take your breath away every morning. Imagine waking up to the serene beauty of nature, right at

  Robyn Bradley Woods Realty Group

  5515 Van Meter Rd, Winchester, KY 40391
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  /31

  $194,000 Sold May 22, 2025

  • 1,352 Sq Ft
  • $143/SF
  • 3 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2004

  429 Paisley Ct, Winchester, KY 40391

  Excellent Townhome ready for you to move in! Great location, 2 Primary Bedrooms, 2 Full Bathrooms, and one 1/2 Bathroom! Fenced in yard, Spacious Deck, One Car attached Garage! Call today to schedule your showing!

  Whitney Ensor Ensor Real Estate LLC

  429 Paisley Ct, Winchester, KY 40391
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  /28

  Est $182,473 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  18 A St, Winchester, KY 40391

  18 A St, Winchester, KY 40391
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  /67

  $549,000

  • 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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  /44

  $225,000 Sold May 22, 2025

  • 1,790 Sq Ft
  • $126/SF
  • 0 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  308 Vaught Ct Unit A & B, Winchester, KY 40391

  Investor's Dream! All-Brick Duplex Fully Rented & Priced Below Appraisal! This all-brick duplex is the perfect addition to your investment portfolio! Featuring a brand new roof, this property is fully occupied with great tenants already in place.Side A is a 2 bed 1 bath unit with fireplace.Side B is a 2 bed 1 bath unit on a basement.Washer dryer hook ups in both units.Located in a convenient &

  Kimberley A Buckner EXP Realty, LLC

  308 Vaught Ct Unit A & B, Winchester, KY 40391
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  /22

  Est $187,016 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  339 W Washington St, Winchester, KY 40391

  339 W Washington St, Winchester, KY 40391
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  /92

  $1,200,000

  • 5 Beds
  • 7 Baths
  • 8,236 Sq Ft

  6237 Bybee Rd, Winchester, KY 40391

  Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
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  /35

  $248,000 Sold May 22, 2025

  • 1,773 Sq Ft
  • $140/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  206 Moss Cir, Winchester, KY 40391

  This 3 bedroom 2 bathroom home is located in the established Spring Hill Subdivision. Separate Utility/Mud room and one car garage. Two very spacious full bathrooms. Covered front porch creates nice space for relaxing. The rear patio overlooks a nice fenced in back yard with storage building. Roof shingles replaced in 2022.

  David Baesler Kentucky Dreams Realty

  206 Moss Cir, Winchester, KY 40391
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  /35

  Est $322,399 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,270 Sq Ft

  149 Milwood Dr, Winchester, KY 40391

  149 Milwood Dr, Winchester, KY 40391
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  /19

  $135,000

  • Land
  • 4.01 Acres
  • $33,666 per Acre

  1940 Athens Boonesboro Rd, Winchester, KY 40391

  Escape to tranquility with this beautiful 4-acre lot in Clark County, offering the perfect setting to build your dream home. Tucked away on a quiet road, this property is surrounded by expansive farmland, ensuring ultimate privacy and peaceful living. A serene pond adds to the charm, providing a perfect spot to relax and enjoy the natural beauty of the land. This lot sits directly across from the

  Laura Sizemore Kentucky Land and Home

  1940 Athens Boonesboro Rd, Winchester, KY 40391
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  /2

  $366,363 Sold May 22, 2025

  • 2,269 Sq Ft
  • $161/SF
  • 162 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  140 Gibson Way, Winchester, KY 40391

  This Haywood Park is framed and at plumbing stage, is part of the Trend Collection by Ball Homes. It's a two story plan on a walk-out basement with plenty of room to grow! When you walk through the front door, you're greeted with a versatile flex space then down the hall opens up to the large living room and spacious kitchen. Cozy up next to the fireplace or sip your morning coffee outside on

  Neshia Gaines Christies International Real Estate Bluegrass

  140 Gibson Way, Winchester, KY 40391
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  /41

  Est $319,106 Not Listed For Sale

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

  173 Milwood Dr, Winchester, KY 40391

  173 Milwood Dr, Winchester, KY 40391
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  /48

  $570,000

  • 5 Beds
  • 3 Baths
  • 3,489 Sq Ft

  594 Earlymeade Dr, Winchester, KY 40391

  This stunning 5BR,3BA brick home blends classic charm with modern comfort, all situated in a highly desirable neighborhood. The exterior features clean lime wash brick with contrasting painted trim and a crisp new black roof, new black 6mm gutters, exuding timeless curb appeal. A wide front porch with elegant columns welcomes you into the home, perfect for relaxing or greeting guest.Inside you

  Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391
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  /44

  $206,500 Sold May 21, 2025

  • 1,107 Sq Ft
  • $187/SF
  • 23 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1962

  206 W Clark Dr, Winchester, KY 40391

  Don't miss out on this move-in ready home in Winchester, 15 minutes from Lexington. The beautifully updated home features a NEW furnace & water heater. It has stylish laminate flooring throughout and modern stainless steel appliances. The kitchen shines with updated cabinets, countertops, backsplash, and light fixtures, while the bathroom boasts new tiles and a sleek vanity. A detached single-car

  Peggy Baldridge HomeFirst Real Estate

  206 W Clark Dr, Winchester, KY 40391
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  /27

  Est $275,281 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,650 Sq Ft

  36 Fitch Ave, Winchester, KY 40391

  36 Fitch Ave, Winchester, KY 40391
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  /57

  $475,000

  • 8 Beds
  • 5 Baths
  • 3,845 Sq Ft

  1731 Ford Hampton Rd, Winchester, KY 40391

  Price Improvement Reflects Room forPersonal Updates!Recent price adjustment provides buyers the opportunity to add their own style with updates like fresh paint or new flooring. This spacious property offers exceptional value and strong potential in a sought-after area.Versatile Home on 5.47 Acres with Horse Barn & Multi-Unit Living.Welcome to your private hilltop retreat with

  Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
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  /36

  $309,000 Sold May 21, 2025

  • 1,958 Sq Ft
  • $158/SF
  • 29 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1999

  172 Buckingham Ln, Winchester, KY 40391

  Absolutely Fabulous, this home lots of character, updated kitchen, granite counter tops, 3 bedrooms, master suite down, 2 1/2 baths, large fenced in back yard, located on a cul-de-sac, bonus room, family room, dining, eat in kitchen, 1 large storage building, 1 small storage building, call today!

  Mila Ensor Ensor Real Estate LLC

  172 Buckingham Ln, Winchester, KY 40391
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  /53

  Est $258,108 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,667 Sq Ft

  18 Village Dr, Winchester, KY 40391

  18 Village Dr, Winchester, KY 40391
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  /42

  $265,500

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft

  9 Apache Trail, Winchester, KY 40391

  Beautiful remodeled move-in ready four bedroom, 2 full bath split foyer. Here are some of the updates: New LVP floors throughout entire home. New carpet on the stairs. New paint throughout home. New fan with remote in living room. Range dishwasher, & new refrigerator stay. New mirrors and lights above them in both baths. New garage door and garage door opener (with 2-year warranty). One side of

  Joyce Ratliff Tom Goebel & Company

  9 Apache Trail, Winchester, KY 40391
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  /3

  $219,000 Sold May 20, 2025

  • 1,628 Sq Ft
  • $135/SF
  • 18 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  410 Paisley Ct, Winchester, KY 40391

  Completely remodeled unit! New Granite countertops, Lighting, Plumbing fixtures, Stainless steel appliances, New Painting and carpeting throughout. Will be finished in the next few days and is ready to show. 408 Paisley could be purchased as well.

  John Wilson Bluegrass Properties Group

  410 Paisley Ct, Winchester, KY 40391
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  /41

  Est $214,244 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  314 Snowden Dr, Winchester, KY 40391

  314 Snowden Dr, Winchester, KY 40391
• 

  

  /25

  $279,900

  • 4 Beds
  • 2.5 Baths
  • 3,024 Sq Ft

  816 Stratton Ln, Winchester, KY 40391

  Welcome to your dream home! Nestled in an excellent location in Winchester, KY, this charming 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort and convenience. Enjoy the backyard, ideal for outdoor entertainment and relaxation, as well as the inviting front deck, perfect for sipping your morning coffee or watching the sunset. The above ground pool stays with the home and will be a

  Haley Rollins Dream Maker Realty, LLC

  816 Stratton Ln, Winchester, KY 40391
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  /43

  $165,000 Sold May 20, 2025

  • 1,130 Sq Ft
  • $146/SF
  • 96 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1980

  12005 Irvine Rd, Winchester, KY 40391

  $15K PRICE REDUCTION!!! Perfect Investment Opportunity In The Country! You Can Live In This Cool Berm Home And Rent The Cabin Out Or Have Two Great Cash Flowing Rentals. The Cabin Is Currently Rented For $799 Per Month (Tenant Pays Utilities). There is Also Potential To Build On Top Of The Current Home And Increase Your Rental Portfolio Or Footprint Of The Home! The Berm Home Has 2 Bedrooms

  Patrick Arvin Keller Williams Commonwealth

  12005 Irvine Rd, Winchester, KY 40391
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  /33

  Est $120,347 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,028 Sq Ft

  636 W Lexington Ave, Winchester, KY 40391

  636 W Lexington Ave, Winchester, KY 40391
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  /26

  $219,900

  • 3 Beds
  • 1 Bath
  • 1,354 Sq Ft

  40 Garner St, Winchester, KY 40391

  Charming & Updated Home in College Park! This beautifully renovated 3-bedroom, 1-bath home in Winchester blends timeless charm with modern updates. Featuring new roof electrical, plumbing, kitchen, flooring, bathroom, fresh paint, and brand-new appliances, this home is truly move-in ready. Situated on a spacious corner lot, it offers ample parking with a rare 3-car garage—perfect for storage or a

  Chaney Hughes Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
• 

  /2

  $374,738 Sold May 20, 2025

  • 2,519 Sq Ft
  • $149/SF
  • 9 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2024

  138 Gibson Way, Winchester, KY 40391

  Contract writing period through 12:00 noon on Thursday, November 7th.The Sycamore Bend, part of the Trend Collection by Ball Homes, is a two-story plan that includes a first-floor guest bedroom. The plan offers a versatile flex room off the entry and an open kitchen and family room at the rear of the home. The kitchen offers both a breakfast area, countertop dining at the island, and a pantry.

  Jennifer Sisson Christies International Real Estate Bluegrass

  138 Gibson Way, Winchester, KY 40391
• 

  

  /13

  Est $169,482 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  2 Victory Ave, Winchester, KY 40391

  2 Victory Ave, Winchester, KY 40391
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  /32

  $264,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  528 Estes Dr, Winchester, KY 40391

  Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

  Josh Wood Freedom Realty & Property Mgt

  528 Estes Dr, Winchester, KY 40391
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  /28

  $205,000 Sold May 19, 2025

  • 1,080 Sq Ft
  • $190/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2023

  303 W Washington St, Winchester, KY 40391

  Built in 2023 this home features 3 bedrooms, 2 bathrooms with a great amount of closet space, beautiful LVP flooring, stainless steel appliances and granite countertops in the kitchen. Located near downtown Winchester and I-64.

  Katherine G Pate Bluegrass Properties Group

  303 W Washington St, Winchester, KY 40391
• 

  

  /18

  Est $267,796 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,607 Sq Ft

  14 Long Ave, Winchester, KY 40391

  14 Long Ave, Winchester, KY 40391
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  /38

  $599,500 Open Sun 2PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft

  102 Bella Shae Way, Winchester, KY 40391

  Introducing the Stonewall plan—a stunning brick and stone ranch ideally positioned on a corner lot in Mallard Cove. This 4 bedroom, 2 full bath home with a side-entry garage offers timeless curb appeal and high-end features throughout. The thoughtfully designed layout includes a spacious living room with vaulted ceilings, arched and lighted built-ins, and a gas fireplace with a floor-to-ceiling

  Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
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  /36

  $390,513 Sold May 19, 2025

  • 2,698 Sq Ft
  • $145/SF
  • 32 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1980

  21 Edgewood Dr, Winchester, KY 40391

  This spacious 4-bedroom, 2.5-bathroom, 2,698 sq. ft. ranch in Hampton Manor sits on nearly an acre double lot just 20 minutes from Lexington/Hamburg. The primary suite boasts a walk-in closet, Jacuzzi tub, and ample storage, while three additional large bedrooms offer flexibility for guests or a home office. A well-equipped kitchen, a laundry/pantry room, and formal living with fireplace and

  Kelly Nisbet Coldwell Banker McMahan

  21 Edgewood Dr, Winchester, KY 40391
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  /19

  Est $195,299 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,007 Sq Ft

  30 Upper St, Winchester, KY 40391

  30 Upper St, Winchester, KY 40391
• 

  

  /24

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,306 Sq Ft

  110 Albany Ln, Winchester, KY 40391

  Lovely one level brick ranch on a corner lot conveniently located in the Meadows just off of McClure Rd. 3 bedroom, 2 full bath with a beautiful yard and a storage building out back.

  Jason Townsend Kentucky Residential Real Estate, LLC

  110 Albany Ln, Winchester, KY 40391

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