Winchester, KY Homes for Sale

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  /38

  $275,000

  • 4 Beds
  • 2 Baths
  • 1,924 Sq Ft

  217 Morris Rd, Winchester, KY 40391

  This is the one you've been waiting for! Room for the whole family with country charm just five minutes from the interstate. This 4-bedroom, 2-bath home features both a living room and a cozy den/family room, plus an open kitchen perfect for entertaining. Outside, enjoy an above-ground pool and a versatile tiny home/shed with plumbing and electric nearby—ideal as a man cave, she shed, or

  Patrick Arvin Keller Williams Commonwealth

  217 Morris 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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  /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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  /28

  $49,500

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  706 Pear Ct, Winchester, KY 40391

  Cozy and full of charm! This 3-bedroom, 2-bath manufactured home offers an inviting space with plenty of natural light, a roomy kitchen, and comfortable bedrooms. Located on leased land in a peaceful community, this home is a hidden gem for those looking to own without the high price tag. Current lot rent is $420/ month. Includes a shed for extra storage. Call your agent to schedule an

  Deangela Robinson Keller Williams Commonwealth

  706 Pear Ct, 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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  /20

  $207,500

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  111 Quail Ridge Rd, Winchester, KY 40391

  Welcome Home - Comfortable Living or Smart Investment!Step into this inviting townhome, offering both spacious comfort and excellent investment potential. Featuring two bedrooms and two and a half bathrooms, this well-designed unit boasts a generous living area with a ventless fireplace, creating a warm, welcoming atmosphere.The home's layout connects the living room, dining area, and kitchen

  Kim Dice EXP Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
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  /21

  $205,000

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  109 Quail Ridge Rd, Winchester, KY 40391

  Welcome Home - Comfortable Living or Smart Investment!Step into this inviting townhome, offering both spacious comfort and excellent investment potential. Featuring two bedrooms and two and a half bathrooms, this well-designed unit boasts a generous living area with a ventless fireplace, creating a warm, welcoming atmosphere.The home's layout connects the living room, dining area, and kitchen

  Kim Dice EXP Realty, LLC

  109 Quail Ridge Rd, Winchester, KY 40391
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  /23

  $229,000

  • 3 Beds
  • 2.5 Baths
  • 1,348 Sq Ft

  363 Silverton Way, Winchester, KY 40391

  Unique Setting... Unlike Any Other!Wake up to the beauty of the surrounding countryside — every single day. This 3-bedroom, 2.5-bath townhome is nestled in the desirable Royal Oaks Village, just one mile from I-64, making it a perfect location for both homeowners and renters alike.This low-maintenance property features tile flooring in the foyer, kitchen, and baths. The kitchen comes fully

  Kim Dice EXP Realty, LLC

  363 Silverton Way, 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
• 

  

  /3

  $380,000

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

  200 Evergreen Dr, Winchester, KY 40391

  Introducing the Run For The Roses - 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 bathroom. The kitchen

  Rex Hall United Real Estate Bluegrass

  200 Evergreen Dr, Winchester, KY 40391
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  /103

  $2,650,000

  • 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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  /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 Open Sun 2PM - 4PM

  • 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

  $305,000

  • 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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  /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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  /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

  $259,900

  • 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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  /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

  $259,900

  • 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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  /24

  $280,000 Open Sun 1PM - 3PM

  • 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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  /43

  $270,000

  • 4 Beds
  • 2 Baths
  • 1,539 Sq Ft

  2832 Two Mile Rd, Winchester, KY 40391

  Brand new 4 Bedroom 2 bath home on an acre lot. Home features Master Bedroom suite, separate utility room, new front and back decks to enjoy your peace and quiet. Other features are new fencing and new septic tank. Move-in ready. Close to shopping and restaurants, less than 4 miles. 13 miles to I-75 and 6 miles to I-64. Within 30 minutes to Richmond and Hamburg area of Lexington.

  Robin Horn Keller Williams Commonwealth

  2832 Two Mile Rd, Winchester, KY 40391
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  /67

  $1,600,000

  • Land
  • 55 Acres
  • $29,091 per Acre

  345 Boone Ridge Ln, Winchester, KY 40515

  20 minutes from Lexington in the Iroquois Hunt Country you will find this sanctuary...its not about stellar fencing, a gated entrance or a mcmansion. Its ALL about the one half mile of frontage on the most beautiful stream in the Bluegrass, Boone Creek! This rare and easily accessible frontage is opposed on the other side with rock faced palisades and the most spectacular setting imaginable.

  Linda Willson Homes & Horse Farms Real Estate

  345 Boone Ridge Ln, Winchester, KY 40515
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  /5

  $105,000

  • Land
  • 1.00 Acre
  • $105,000 per Acre

  1730 Mcclure Rd, Winchester, KY 40391

  Awesome property, just waiting for you to build your perfect home, ready to fulfill your dreams, great area close to everything.Seller will run the water line to the propertyLots One and Two have entrances beside each other, shown on plat

  Mila Ensor Ensor Real Estate, LLC

  1730 Mcclure Rd, Winchester, KY 40391
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  /4

  $95,000

  • Land
  • 1.09 Acres
  • $87,156 per Acre

  1700 Mcclure Rd, Winchester, KY 40391

  Awesome property, just waiting for you to build your perfect home, ready to fulfill your dreams, great area close to everything.Seller will run the water line to the propertyLots One and Two have entrances beside each other, shown on plat

  Mila Ensor Ensor Real Estate, LLC

  1700 Mcclure Rd, Winchester, KY 40391
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  /3

  $135,000

  • Land
  • 10 Acres
  • $13,145 per Acre

  4150 Schollsville Rd, Winchester, KY 40391

  This land located in the center of hunting paradise, where nature excels her beauty, a place for you to build your perfect home,10.27acres, call todayCity water is East Clark Water and it is across road, as per the seller back of property has a fence that is not true to the property lineThe gate next to this acreage is not on this property, look for the orange markers on the front fence

  Mila Ensor Ensor Real Estate, LLC

  4150 Schollsville Rd, Winchester, KY 40391
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  /79

  $889,000

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

  1701 Gay Evans Rd, Winchester, KY 40391

  This exceptional home is now offering a brand-new geothermal heating and cooling system for year-round comfort and savings. 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

  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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  /7

  $800,000

  • Land
  • 4.87 Acres
  • $164,271 per Acre

  1108 W Lexington Ave, Winchester, KY 40391

  Rare opportunity to purchase a large multi-family development in the heart of Winchester! Directly across the street from Legacy Grove Park! All building and engineering plans included to build 66 approved townhomes with the possibility of adding 4 more. Currently zoned PD (Planned Development), could possibly be changed to commercial due to neighboring commercial property. Main property is 4.87

  Jason Townsend Kentucky Residential Real Estate, LLC

  1108 W Lexington Ave, 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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  /9

  $206,000

  • Land
  • 8 Acres
  • $26,512 per Acre

  Unlisted Address

  Build your dream home on this gorgeous 7.77-acre lot on Flannagan Station Road in Winchester. Offering a quiet, country setting with gently rolling land, this property is ideal for a custom home, hobby farm, or simply extra space to enjoy. Plenty of room for a house, garden, or recreational use, with beautiful views all around. Located just minutes from the Winchester Bypass for an easy commute

  Shari Frasure Keller Williams Commonwealth

  Unlisted Address
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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
• 

  

  /42

  $619,000

  • 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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  /5

  $29,000

  • Land
  • 0.46 Acre
  • $63,043 per Acre

  102 Augusta Dr, Winchester, KY 40391

  This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

  Dale Hatton Dream Maker Realty, LLC

  102 Augusta Dr, Winchester, KY 40391

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