Winchester, KY Houses for Sale

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  /34

  $235,000

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

  37 7th St, Winchester, KY 40391

  Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

  Andrew Fugitt Coldwell Banker McMahan

  37 7th St, Winchester, KY 40391
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  /31

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,201 Sq Ft

  210 Moss Ct, Winchester, KY 40391

  Nice 3 bedroom, 2 bath, all one level, ranch home! Convenient location! Nice patio to sit out back in the mostly privacy fenced in yard. Only needs a few panels to be completely fenced if desired. One car garage. Easy to maintain lot. Large kitchen. Good sized bedrooms. Windows, HVAC, and roof all replaced within the last 8 years. This will make someone a great home!

  Jason Townsend Kentucky Residential Real Estate, LLC

  210 Moss Ct, Winchester, KY 40391
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  /14

  $265,000

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  10 Upper St, Winchester, KY 40391

  Modern Ranch residence full un-finished basement, large lot.

  E. Clark Toleman Real Estate Appraisal Services

  10 Upper St, Winchester, KY 40391
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  /47

  $259,000

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

  17 Euclid Ave, Winchester, KY 40391

  Welcome to 17 Euclid Ave, a charming two-story home in the heart of Winchester! This beautifully maintained property features 3 bedrooms and 2 full baths, offering ample space and comfort. Enjoy the outdoors with a spacious deck perfect for relaxing or entertaining, surrounded by mature trees that provide shade and privacy. Convenient off-street parking ensures easy access, and the home's prime

  Donna Thwaites Thwaites Realtors LLC

  17 Euclid Ave, Winchester, KY 40391
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  /53

  $559,000

  • 4 Beds
  • 3 Baths
  • 2,482 Sq Ft

  5 Fairwood Ln, Winchester, KY 40391

  Just a two minute walk from Winchester Country Club, this architect-designed 4BR/3BA split-level home was taken to the studs in 2013 and rebuilt with timeless craftsmanship and modern ease. Light-filled spaces, rich hardwood floors, a custom kitchen by Shaker Village's Terry Craycraft, granite countertops, abundant cabinetry, and a hidden pantry.. The spa-like main-level primary suite is a true

  Kathryn Cheuvront Coldwell Banker McMahan

  5 Fairwood Ln, Winchester, KY 40391
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  /56

  $639,000

  • 6 Beds
  • 4.5 Baths
  • 4,021 Sq Ft

  4455 Colby Rd, Winchester, KY 40391

  Gorgeous Ranch Home On Basement, Situated Perfectly On Over 3.5 Lush Acres Of Level Seclusion, As Property Is Lined Beautiful, Mature Trees! Enjoy Peace & Quiet In This Newly Renovated Home, Offering 6 Bedrooms, 5 Baths, Ample Family Space, Home Office, (Fiber Optic Internet), Large Separate Laundry, Sun Room, 2 Covered Porches, Deck, Fire Pit, 2 Car Garage, Barn/ Workshop... THE LIST GOES ON!

  Melissa Thompson Keller Williams Legacy Group

  4455 Colby Rd, Winchester, KY 40391
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  /48

  $219,900

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  59 Holiday Rd, Winchester, KY 40391

  NEW PRICE! With limited inventory on the market, don't wait too long to view this brick ranch that offers comfort, updates, and a spacious outdoor area—all at an affordable price!This home features 3 bedrooms and 1 full bath, with fresh interior paint and newer laminate flooring for a clean, modern feel. The living spaces are filled with natural light, making the home feel warm and

  Kathy Burton Coldwell Banker McMahan

  59 Holiday Rd, Winchester, KY 40391
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  /57

  $359,000

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft

  356 Boone Ave, Winchester, KY 40391

  Step into timeless charm with this beautifully renovated home on one of Winchesters most historic streets. Built over 100 years ago, this 3200 sq ft residence blends classic character with modern updates. You will love the updated kitchen featuring granite countertops, stainless appliances and plenty of space for cooking and entertaining in the large dining room. This home showcases re-tiled

  Nancy Smith Rector Hayden Realtors

  356 Boone Ave, Winchester, KY 40391
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  /37

  $1,249,500

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

  700 Nick Ln, Winchester, KY 40391

  🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you

  Darrell Tackett Dream Maker Realty, LLC

  700 Nick Ln, Winchester, KY 40391
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  /33

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  1831 Kiddville Rd, Winchester, KY 40391

  Offering a perfect blend of modern comfort, energy efficiency, and country charm. Conveniently located just 1.3 miles from Exit 10 off the Bert T. Combs Mountain Parkway, this property provides easy access to both natural beauty and city amenities, with Downtown Winchester only 15 miles away and Natural Bridge State Park just 27 miles down the road. The living area features a cozy vent-free gas

  Joshua Davis The Agency

  1831 Kiddville Rd, Winchester, KY 40391
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  /40

  $332,000

  • 3 Beds
  • 2 Baths
  • 1,988 Sq Ft

  13544 Irvine Rd, Winchester, KY 40391

  Experience Stunning Sunrises and Starry Nights!Nestled on nearly 4 peaceful acres, this charming brick ranch offers the tranquility of country living with modern comfort. Surrounded by a beautiful tree grove, the home features a full walk-out basement with exciting potential—finish the lower level and additional bathroom to expand your living space!Inside, you'll find 3 spacious

  Susan Baldwin Rector Hayden Realtors

  13544 Irvine Rd, Winchester, KY 40391
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  /34

  $289,900

  • 4 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  410 E Broadway St, Winchester, KY 40391

  Completely remodeled 4 bedroom, 2.5 bath home located in the heart of downtown Winchester. This home features a spacious open floor plan, a first-floor primary suite and a lot of charm. The kitchen, living, and dining areas flow together seamlessly, offering ample space and natural light. Upstairs includes three additional bedrooms and a full bath. Outside, enjoy a large backyard with pool and

  Erin Hurst Bluegrass Properties Group

  410 E Broadway St, Winchester, KY 40391
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  /114

  $649,000

  • 5 Beds
  • 4.5 Baths
  • 5,524 Sq Ft

  315 The Woods Ln, Winchester, KY 40391

  Beautiful 1.5-story brick home on a cul-de-sac with in-ground pool and walkout basement! The main level features hardwood floors, office, formal dining room, and spacious family room with gas fireplace. The kitchen includes stainless appliances (all convey), double oven, gas cooktop, island, eat-in area, and large pantry. Oversized mudroom/laundry adds great storage. First-floor primary suite

  Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
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  /3

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  225 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

  225 Evergreen Dr, Winchester, KY 40391
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  /2

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  215 Evergreen Dr, Winchester, KY 40391

  Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  215 Evergreen Dr, Winchester, KY 40391
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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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  /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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  /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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  /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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  /35

  $315,000

  • 3 Beds
  • 2.5 Baths
  • 1,948 Sq Ft

  607 Colby Ridge Blvd, Winchester, KY 40391

  Built by Kessinger Construction, this open floor plan home offers plenty of layout and entertaining options. The durable luxury vinyl tile flooring is through the first floor, utility room and bathrooms. The first floor also features 9' ceilings. The kitchen offers an island ideal for bar stools and there is a spacious dining area. A door leads to a covered porch with a ceiling fan overlooking a

  Suzanne Elliott Berkshire Hathaway de Movellan Properties

  607 Colby Ridge Blvd, 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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  /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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  /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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  /13

  $340,000

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

  410 W Lexington Ave, Winchester, KY 40391

  Estate Sale. Selling 'AS IS', in 2024 new roof, walls repaired and freshly painted throughout.Great home for a growing family, covered front porch, 10-foot ceilings upstairs and down, handicap ramp, ample parking in rear. Motivated seller, call for your private showing today

  Melisa McDonald Wrenn Realty

  410 W Lexington Ave, Winchester, KY 40391
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  /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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  /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
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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 Management

  528 Estes Dr, Winchester, KY 40391
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  /38

  $599,500

  • 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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  /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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  /78

  $890,000

  • 4 Beds
  • 3.5 Baths
  • 4,221 Sq Ft

  1701 Gay Evans Rd, Winchester, KY 40391

  Escape to your own private retreat with this beautiful brick ranch set on 8 plus acres. This home boasts a bright and airy sunroom, perfect for enjoying morning coffee watching the sunrise or unwinding with the nature views. The fully finished basement offers extra living space, while the in-ground pool is ready for summer fun. This property offers a two-car attached garage as well as a

  Kathryn Cheuvront Coldwell Banker McMahan

  1701 Gay Evans Rd, Winchester, KY 40391
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  /69

  $639,900

  • 3 Beds
  • 3 Baths
  • 2,927 Sq Ft

  2085 Hancock Valley Dr, Winchester, KY 40391

  Spacious 3-Bedroom Home on Nearly 5 Acres in Winchester, KY!Discover country living at its finest with this beautiful 3-bedroom, 3-bathroom home set on nearly 5 acres of picturesque land. Featuring beautiful hardwood floors, a finished basement, and plenty of space for entertaining and friends, this property is designed for comfort and social gatherings. Enjoy the in-ground pool, pole barn,

  Terry Billiter Premier Property Consultants

  2085 Hancock Valley Dr, Winchester, KY 40391
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  /69

  $975,000

  • 5 Beds
  • 3.5 Baths
  • 2,842 Sq Ft

  1150 Craig Crossing, Winchester, KY 40391

  Stunning new construction featuring 5 bedroom. 3.5 bath nestled on roughly 2.5 serene acres, surrounded by picturesque farmland and panoramic views. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden walk in pantry with custom cabinets and well appointed appliances. Hardwood floors and

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  1150 Craig Crossing, Winchester, KY 40391
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  /36

  $829,900

  • 2 Beds
  • 3 Baths
  • 12,900 Sq Ft

  8129 Wades Mill Rd, Winchester, KY 40391

  This is what BARDOMINIUM Dreams are made of!!!! Welcome to your barndo retreat — an expansive 92' x 120' steel-framed structure situated on 4.27 partially fenced acres with breathtaking pond views and unmatched amenities for both living and working.This massive structure boasts an open-concept interior layout with endless potential! Ideal for combining luxury living with functional workspace.

  Holly Goeing The Agency

  8129 Wades Mill Rd, Winchester, KY 40391
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  /42

  $239,000

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft

  363 S Main St, Winchester, KY 40391

  ** Seller is offering a $10,000 credit at close with an acceptable offer!**Welcome to 363 South Main Street in the heart of Winchester, Kentucky! This charming 3-bedroom, 2-bath home offers the perfect blend of timeless character and modern convenience. Built in 1940, the home exudes classic appeal with thoughtful updates that meet today's lifestyle. With 2,142 square feet of living

  Zachary Otis HomeLand Real Estate Inc

  363 S Main St, Winchester, KY 40391
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  /8

  $129,000

  • 2 Beds
  • 1 Bath
  • 637 Sq Ft

  109 Spring St, Winchester, KY 40391

  Investment opportunity in Winchester! This 2-bedroom, 1-bath home at 109 Spring St is currently tenant-occupied and leased at $900/month. Functional layout with a spacious kitchen and separate living area. Conveniently located near downtown, schools, and local amenities. Whether you're expanding your portfolio or looking for a starter investment, this property offers steady rental income from day

  Shari Frasure Keller Williams Commonwealth

  109 Spring St, Winchester, KY 40391
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  /42

  $635,000

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

  439 Lynnway Dr, Winchester, KY 40391

  --Contingent Offer w/ 72hr Kick-Out in place--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,

  Reagan Rainey Dream Maker Realty, LLC

  439 Lynnway Dr, Winchester, KY 40391
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  /62

  $269,950

  • 3 Beds
  • 2 Baths
  • 1,247 Sq Ft

  3614 Stamper Dr, Winchester, KY 40391

  Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, Winchester, KY 40391
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  /73

  $334,900

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft

  407 Fairholme Way, Winchester, KY 40391

  Looking for a newer home in a beautiful, family friendly neighborhood? Look no further than this lovely, low maintenance home in the desirable Fairholme Estates subdivision. Take a step inside and enjoy the sunlight streaming in through the abundant windows in the great room. Gleaming, easy to clean, laminate wood plank flooring spills into the spacious kitchen area which features an oversized

  Josh Wood Freedom Realty & Property Management

  407 Fairholme Way, Winchester, KY 40391
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  /48

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft

  40 N Burns Ave, Winchester, KY 40391

  This stunning fully remodeled 3-bedroom, 2-bathroom home is move-in ready with top-to-bottom updates. Every detail has been thoughtfully upgraded, from the modern lighting in every room to the brand-new flooring and fresh paint throughout. The kitchen is a standout with granite countertops, new cabinetry, and brand-new appliances, while the bathrooms boast quartz countertops and elegant tiled

  Ernesto Martinez Berkshire Hathaway HomeServices Foster Realtors

  40 N Burns Ave, Winchester, KY 40391
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  /79

  $239,900

  • 4 Beds
  • 2 Baths
  • 3,295 Sq Ft

  133 S Burns Ave, Winchester, KY 40391

  Beautiful, Old-World style in the heart of Winchester! From the red, domed porch roof to the arched doorways and multiple fireplaces, this home is full of character and class. Being sold as-is, but with many renovations and updates already done to maintain and restore the charm of this old beauty including a new shingle roof (2024), replaced porch boards, and a fresh coat of interior paint. The

  Josh Wood Freedom Realty & Property Management

  133 S Burns Ave, Winchester, KY 40391

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