Winchester, KY Homes

• 

  

  

  /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
• 

  

  

  /19

  Est $187,734 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  360 W Washington St, Winchester, KY 40391

  360 W Washington St, Winchester, KY 40391
• 

  

  

  /63

  $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
• 

  

  

  /36

  $214,000 Sold May 19, 2025

  • 1,402 Sq Ft
  • $153/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2000

  509 Hidden Hills Way, Winchester, KY 40391

  This home is a must-see and would be perfect for a Welcome Home Grant, a program that gets the buyer a chance for a $20,000 purchase grant. Offering 3 or 4 bedrooms and 2 full baths, this home also features a large covered back patio and secluded back yard area so you can enjoy the Spring days ahead. If you have a lot of 'stuff', no worries. The storage building stays also. Need more info on

  Teresa Richmond Freedom Realty & Property Mgt

  509 Hidden Hills Way, Winchester, KY 40391
• 

  

  

  /44

  Est $143,710 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,053 Sq Ft

  23 Waveland Ave, Winchester, KY 40391

  23 Waveland Ave, Winchester, KY 40391
• 

  

  /5

  $45,000

  • Land
  • 0.36 Acre
  • $125,000 per Acre

  434 Fairholme Way, Winchester, KY 40391

  Ready to build your forever home? Look no further! This lot is conveniently located in the highly sought after Fairholme Estates, which is a short golf cart ride to the Winchester Country Club and downtown Winchester.

  Justin Lee JL Realty Group, LLC

  434 Fairholme Way, Winchester, KY 40391
• 

  

  /47

  $396,500 Sold May 19, 2025

  • 2,400 Sq Ft
  • $165/SF
  • 51 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1980

  520 Bailey Ln, Winchester, KY 40391

  Beautiful large ranch completely remodeled manufactured home on 24 acres with large addition. large bedrooms, family room, dining room, formal living room, 4 Bedroom and 3 baths. 30 foot above ground pool multiple outbuildings, front porch large back patio and just minutes from downtown Winchester. All new Bathrooms, All new Kitchen, All new fixtures, All new flooring. All new paint. House

  Paul Waddelow Hand in Hand Realty Central KY

  520 Bailey Ln, Winchester, KY 40391
• 

  

  /81

  Est $215,456 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,236 Sq Ft

  245 Mutual Ave, Winchester, KY 40391

  245 Mutual Ave, Winchester, KY 40391
• 

  

  /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
• 

  

  /44

  $515,000 Sold May 19, 2025

  • 4,091 Sq Ft
  • $126/SF
  • 294 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1958

  31 Bonnie Brook Ln, Winchester, KY 40391

  This Warfield Gratz designed rare beauty and history is located in the heart of Winchester. Embrace the essence of elegance in this beautifully appointed brick home, offering 5 bedrooms, 3 full baths and formal rooms. Main level of home boasts the primary suite as well as an additional bedroom. The large fully equipped kitchen is a delight for any chef. Home features a full walk-up basement

  Kelly Nisbet Coldwell Banker McMahan

  31 Bonnie Brook Ln, Winchester, KY 40391
• 

  

  /28

  Est $155,856 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  223 Pendleton St, Winchester, KY 40391

  223 Pendleton St, Winchester, KY 40391
• 

  

  /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
• 

  

  /41

  $240,000 Sold May 16, 2025

  • 1,874 Sq Ft
  • $128/SF
  • 16 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1974

  860 Harkins Dr, Winchester, KY 40391

  Welcome to 860 Harkins Drive! This spacious split-foyer home features 4 bedrooms, 2 full bathrooms, a garage, and a large back deck perfect for outdoor entertaining. Conveniently located near public parks, the public library, and easy access to the Winchester Bypass. A fantastic opportunity for comfortable living in Winchester!

  Joseph Miller Keller Williams Commonwealth

  860 Harkins Dr, Winchester, KY 40391
• 

  

  /17

  Est $177,522 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,032 Sq Ft

  54 Melbourne St, Winchester, KY 40391

  54 Melbourne St, Winchester, KY 40391
• 

  

  /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
• 

  

  /18

  $246,500 Sold May 16, 2025

  • 1,176 Sq Ft
  • $210/SF
  • 35 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1978

  6278 Irvine Rd, Winchester, KY 40391

  **Attention Investors, Homesteaders, and First-Time Home Buyers!** Seize this rare opportunity to own a charming 3 bedroom 1.5 bath Ranch Home tucked away on a stunning 13.9-acre property! Being sold ''as is''. Step inside to an inviting open-concept design featuring beautiful hardwood floors, stylishly updated bathrooms, and modern laminate flooring in the master bedroom. Don't let this hidden

  Angela Yonts EXP Realty, LLC

  6278 Irvine Rd, Winchester, KY 40391
• 

  

  /19

  Est $186,848 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,352 Sq Ft

  29 Cook Ave, Winchester, KY 40391

  29 Cook Ave, Winchester, KY 40391
• 

  

  /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
• 

  

  /55

  $520,000 Sold May 15, 2025

  • 4,659 Sq Ft
  • $112/SF
  • 61 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1995

  427 Calmes Blvd, Winchester, KY 40391

  Welcome to 427 Calmes Blvd, a spacious and beautifully updated home in the desirable Oak Hill subdivision. This 4-bedroom, 3.5-bath home sits on a corner lot with a fenced yard, offering plenty of space both inside and out. The main level features a first-floor primary suite, along with two additional bedrooms, while a second master suite upstairs provides extra privacy—perfect for guests or

  Kymberly Clem EXP Realty, LLC

  427 Calmes Blvd, Winchester, KY 40391
• 

  

  /13

  Est $138,460 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 943 Sq Ft

  234 Pendleton St, Winchester, KY 40391

  234 Pendleton St, Winchester, KY 40391
• 

  

  /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
• 

  

  /63

  $1,325,000 Sold May 15, 2025

  • 5,736 Sq Ft
  • $231/SF
  • 72 Days On Market

  • 5 Beds
  • 8 Baths
  • Built 2021

  6755 Boonesboro Rd, Winchester, KY 40391

  Stunning and private! This bluegrass property spans 13.9 acres and is ideally located 15 minutes from Lexington, and minutes to Richmond, and Winchester. It boasts a custom, designer chef's kitchen with a gas range, double oven, double refrigerator, and a massive granite island that seats 10+ people. The open concept features a gorgeous great room with shiplap ceilings, exposed wood beams and a

  Jennifer Ray RE/MAX Elite Lexington

  6755 Boonesboro Rd, Winchester, KY 40391
• 

  

  /26

  Est $164,585 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  37 Sterling St, Winchester, KY 40391

  37 Sterling St, Winchester, KY 40391
• 

  

  /7

  $825,000

  • Land
  • 4.87 Acres
  • $169,405 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
• 

  

  /24

  $186,000 Sold May 14, 2025

  • 1,188 Sq Ft
  • $157/SF
  • 77 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  205 Arbor Ct, Winchester, KY 40391

  Charming 3 bedroom, 2 bath cottage with a fenced side yard, perfect for the furbabies or just for outdoor relaxation. Property includes a shed for extra storage. Your cozy new home awaits!

  Kathryn Cheuvront Coldwell Banker McMahan

  205 Arbor Ct, Winchester, KY 40391
• 

  

  /37

  Est $177,400 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft

  27 Magnolia St, Winchester, KY 40391

  27 Magnolia St, Winchester, KY 40391
• 

  

  /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
• 

  

  /6

  $51,000 Sold May 14, 2025

  • Land
  • 0.25 Acre
  • $204,000 per Acre

  • 325 Days On Market

  214 Ashton Oak Way, Winchester, KY 40391

  A Unique Opportunity to Build your Dream Home in the Plantation Section of Royal Oaks in Clark County. Situated on..25. acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

  Melia Hord Keller Williams Bluegrass Realty

  214 Ashton Oak Way, Winchester, KY 40391
• 

  

  /12

  Est $167,210 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  23 Magnolia St, Winchester, KY 40391

  23 Magnolia St, Winchester, KY 40391
• 

  

  /52

  $530,000

  • 3 Beds
  • 2.5 Baths
  • 2,020 Sq Ft

  1778 Elkin Rd, Winchester, KY 40391

  Peaceful Living on 8.83 acres of gently rolling hills in the heart of Kentucky. Breathtaking countryside features a newer custom-built home that offers peace, privacy and serene surroundings. Wake up to birdsong, watch deer wander at dusk and soak in the golden sunsets from your own front porch. Highlights include: spacious open concept kitchen with white custom cabinetry, beautiful engineered

  Vicki VanWinkle Pacesetters Real Estate

  1778 Elkin Rd, Winchester, KY 40391
• 

  

  /36

  $177,500 Sold May 13, 2025

  • 1,259 Sq Ft
  • $141/SF
  • 3 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1998

  406 Pepperwood Ct, Winchester, KY 40391

  Looking for stress free living with a beautiful view in a great location? This townhouse overlooks the rolling hills of KY, located just off I-64 with easy access to Lexington and the Mountain Parkway. Features hardwood floors, ceramic tile and LVT flooring. Separate utility room and spacious 2 car garage with a large unfinished room in the basement. 2 bedrooms upstairs, each with their own

  Peggy Baldridge HomeFirst Real Estate

  406 Pepperwood Ct, Winchester, KY 40391
• 

  

  /15

  Est $196,631 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  12 Linden Ave, Winchester, KY 40391

  12 Linden Ave, Winchester, KY 40391
• 

  

  /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
• 

  

  /20

  $135,000 Sold May 13, 2025

  • 1,194 Sq Ft
  • $113/SF
  • 13 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  100 Dallas Alley, Winchester, KY 40391

  Check out this beautifully refreshed home featuring a brand-new metal roof and a unique floorplan designed for flexibility. Enjoy easy access to downtown and ample parking space for 4 to 6 vehicles. The versatile layout allows for additional bedrooms, making it perfect for growing families or guests. Don't miss this opportunity for modern comfort with convenient urban access!

  Emidio Figueroa Rector Hayden Realtors

  100 Dallas Alley, Winchester, KY 40391
• 

  

  /59

  Est $180,613 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,520 Sq Ft

  114 Holly Ave, Winchester, KY 40391

  114 Holly Ave, Winchester, KY 40391
• 

  

  /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
• 

  /2

  $110,000 Sold May 13, 2025

  • Land
  • 0.42 Acre
  • $261,905 per Acre

  • 900 Days On Market

  140 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

  140 Duclair Dr, Winchester, KY 40391
• 

  

  /30

  Est $196,031 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,244 Sq Ft

  141 Holly Ave, Winchester, KY 40391

  141 Holly Ave, Winchester, KY 40391
• 

  

  /41

  $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
• 

  

  /23

  $210,000 Sold May 12, 2025

  • 1,200 Sq Ft
  • $175/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  202 Washington Square, Winchester, KY 40391

  Step into this beautifully updated home featuring 3 spacious bedrooms and 2 full bathrooms. The modern kitchen boasts sleek granite countertops, stainless steel appliances, and plenty of cabinet space perfect for cooking or entertaining.

  Aaron Kendall Lifstyl Real Estate

  202 Washington Square, Winchester, KY 40391

Showing Results 281 - 320, Page 8 of 18