Winchester, KY Homes

• 

  

  

  /10

  Est $206,246 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,230 Sq Ft

  282 Winn Ave, Winchester, KY 40391

  282 Winn Ave, Winchester, KY 40391
• 

  

  

  /46

  $624,000

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

  433 Fairholme Way, Winchester, KY 40391

  This elegant ranch on a basement offers refined main-level living with upscale finishes throughout. The chef's kitchen is a standout featuring double ovens, custom soft-close cabintry, granite countertops, a large island with seating, a spacious walk-in pantry for entertaining and everyday ease. Primary bedroom has Amish cutom built closet. Enjoy quiet evenings on the covered front porch with

  Kathryn Cheuvront Coldwell Banker McMahan

  433 Fairholme Way, Winchester, KY 40391
• 

  

  

  /23

  $135,000 Sold Jul 02, 2025

  • Land
  • 5 Acres
  • $27,000 per Acre

  • 69 Days On Market

  2100 Old Log Lick Rd, Winchester, KY 40391

  Dreaming of peaceful country living with a head start on the building process? This beautiful 5-acre tract in the country has everything you need to get started: electric and water already in place, a septic system installed, and a cleared, flat spot just waiting for your dream home. The property features a pond, a gravel driveway, and a small shop with a bathroom and attached carport, perfect

  Michelle Blackburn RE/MAX Creative, Winchester

  2100 Old Log Lick Rd, Winchester, KY 40391
• 

  

  

  /21

  Est $144,397 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  48 Watts Rd, Winchester, KY 40391

  48 Watts Rd, Winchester, KY 40391
• 

  

  

  /65

  $713,500

  • 6 Beds
  • 4.5 Baths
  • 6,243 Sq Ft

  418 David Ln, Winchester, KY 40391

  This impeccable house is a Buyer's Delight. Located in the most desirable residential neighborhood, Stoney Brook. Discover a serene retreat in this beautifully appointed home, offering spacious interiors and breathtaking outdoor spaces. Step into the front door and discover the soaring ceilings with beautifully appointed crown molding. The flowing space from the dining room to the great room to

  Craig Bridgewater Bridgewater Real Estate

  418 David Ln, Winchester, KY 40391
• 

  

  /13

  $75,000 Sold Jul 01, 2025

  • 1,113 Sq Ft
  • $67/SF
  • 74 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1920

  2431 Pine Ridge Rd, Winchester, KY 40391

  Looking for a quite place in the country that will give you enough room for a great garden, a few chickens and a huge helping of peace and quiet?? This little gem may be for you. A 1920 built wood home tucked away in the hills of Clark County. Call today for your private showing.

  A. Rebecca Woods Woods Realty Group

  2431 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /25

  Est $59,453 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft

  248 Cook Ave, Winchester, KY 40391

  248 Cook Ave, Winchester, KY 40391
• 

  

  /14

  $255,000

  • 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
• 

  

  /22

  $334,327 Sold Jul 01, 2025

  • 1,997 Sq Ft
  • $167/SF
  • 219 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  136 Gibson Way, Winchester, KY 40391

  The Laurel Square, part of the Trend Collection by Ball Homes, is two story plan with a very open first floor layout. The island kitchen offers both a breakfast area and countertop dining, and a large pantry. Granite kitchen counter tops with stainless steel 50/50 under-mount sink and full back splash. Stainless steel appliances including smooth top range, microwave and dishwasher. The kitchen

  Neshia Gaines Christies International Real Estate Bluegrass

  136 Gibson Way, Winchester, KY 40391
• 

  

  /4

  Est $84,924 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 940 Sq Ft

  234 Cook Ave, Winchester, KY 40391

  234 Cook Ave, Winchester, KY 40391
• 

  

  /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
• 

  

  /4

  $315,000 Sold Jun 30, 2025

  • 2 Days On Market

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391

  Welcome to this wonderful world , 48 acres of vacant land, you must see this gently rolling piece of property, build your next dream home, explore nature, call today! There is no survey or restrictions, buyer to have a septic analysis at their cost, buyer to check with Clark Co Road department about entrance to property, as per East Clark Water it is across the road. Posts are marked on

  Mila Ensor Ensor Real Estate, LLC

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391
• 

  

  /27

  Est $281,394 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  198 Hilltop Dr, Winchester, KY 40391

  198 Hilltop Dr, Winchester, KY 40391
• 

  

  /46

  $379,000

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft

  7875 Bybee Rd, Winchester, KY 40391

  Want 20 acres on which to roam and hunt or have a small farm operation? You will also have a nice 2021 3 bedroom, 2 full bath double wide home. There is a 3-bent barn where you can have a home for some animals. Primary bedroom has a walk-in shower, double sink, and walk-in closet. In fact, all bedrooms have a walk-in closet. Range, refrigerator and dishwasher stay. Front porch, deck on back and

  Joyce Ratliff Tom Goebel & Company

  7875 Bybee Rd, Winchester, KY 40391
• 

  

  /34

  $205,000 Sold Jun 30, 2025

  • 1,013 Sq Ft
  • $202/SF
  • 13 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  42 Wheeler Ave, Winchester, KY 40391

  Location and low maintenance combined with tons of hobby space describes this freshly remodeled bungalow near College Park! Two bedrooms with a bonus room upstairs previously used as 2 more small bedrooms, brand new refrigerator, stove, washer and dryer! Open concept living / dining area. Really nice, recently built detached 22'x24' garage and carport out back with another garage in the

  Jason Townsend Kentucky Residential Real Estate, LLC

  42 Wheeler Ave, Winchester, KY 40391
• 

  

  /23

  Est $248,414 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft

  130 Hilltop Dr, Winchester, KY 40391

  130 Hilltop Dr, Winchester, KY 40391
• 

  

  /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

  W Patrick Arvin Keller Williams Commonwealth

  217 Morris Rd, Winchester, KY 40391
• 

  

  /38

  $220,000 Sold Jun 30, 2025

  • 1,333 Sq Ft
  • $165/SF
  • 19 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1973

  212 Southwind Dr, Winchester, KY 40391

  Looking for a really nice, move-in ready, brick ranch home that won't break the bank? Look no further! This home is located on a low traffic neighborhood street that's very convenient to schools, shopping, and access to I-64. You can be in Hamburg in approximately 20 minutes! 3 nicely sized bedrooms, 1.5 baths, and a family room with a soaring vaulted ceiling. Relax in the shade of mature

  Jim Woodrum RE/MAX Creative, Winchester

  212 Southwind Dr, Winchester, KY 40391
• 

  

  /70

  Est $274,704 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,321 Sq Ft

  1131 Ironworks Rd, Winchester, KY 40391

  1131 Ironworks Rd, Winchester, KY 40391
• 

  

  /48

  $219,900 Open Sat 1PM - 3PM

  • 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
• 

  

  /31

  $231,000 Sold Jun 30, 2025

  • 1,404 Sq Ft
  • $165/SF
  • 17 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1980

  619 Laura Dr, Winchester, KY 40391

  This beautiful 3-bedroom ranch is ready for you to make it your own. The home boasts 1400 SQ FT and has a wonderful floor plan. Step inside and check out the living room, which has great natural light and lots of space to relax or enjoy company. Home also has a bonus room next to the living room that adds a ton of space for living, work, or play. The formal dining area allows for easy mealtimes

  Kevin Bradley KB Realty Group

  619 Laura Dr, Winchester, KY 40391
• 

  

  /26

  Est $227,548 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  1124 Ironworks Rd, Winchester, KY 40391

  1124 Ironworks Rd, Winchester, KY 40391
• 

  

  /9

  $500,000

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
• 

  

  /49

  $390,000 Sold Jun 30, 2025

  • 1,900 Sq Ft
  • $205/SF
  • 26 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1940

  1094 Ford Hampton Rd, Winchester, KY 40391

  Introducing 1094 Ford Hampton Road, a Nice, Updated Farmhouse On 5.015 Acres of Gently Rolling Hills. This Lovely Home Features an Updated Kitchen with Ample Counter and Cabinet Space with a Large Farm Sink and Quartz Countertops, a See-Through Gas Fireplace Between the Dining Area and Den, a 1st Floor Primary Bedroom/Bathroom, Plus a 1st Floor Laundry/Full Bathroom. Upstairs There is 2 Bedrooms.

  Tom D. Thomas The Real Estate Co.

  1094 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /41

  Est $237,062 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,982 Sq Ft

  273 Winn Ave, Winchester, KY 40391

  273 Winn Ave, Winchester, KY 40391
• 

  

  /7

  $270,000

  • Land
  • 0.84 Acre
  • $321,429 per Acre

  800 Interstate Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

  Whitney Ensor Ensor Real Estate, LLC

  800 Interstate Dr, Winchester, KY 40391
• 

  

  /17

  $30,000 Sold Jun 30, 2025

  • Land
  • 1.72 Acres
  • $17,442 per Acre

  • 51 Days On Market

  12591 Ironworks Rd, Winchester, KY 40391

  This 1.722-acre lot presents a fantastic opportunity to design your ideal home in the subdivision of Eskippakithiki Overlooks. Enjoy the lovely views and ample space to unwind and relax. Located just minutes from Bert T. Combs Mountain Parkway, this property offers both convenience and tranquility. Utilities are readily available at the road, allowing you to start planning your new home right

  Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391
• 

  

  /38

  Est $235,559 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  113 Mary Way, Winchester, KY 40391

  113 Mary Way, Winchester, KY 40391
• 

  

  /28

  $44,999

  • 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
• 

  

  /19

  $30,000 Sold Jun 30, 2025

  • Land
  • 2.34 Acres
  • $12,821 per Acre

  • 51 Days On Market

  12651 Ironworks Rd, Winchester, KY 40391

  This 2.336-acre lot presents a fantastic opportunity to design your ideal home in the subdivision of Eskippakithiki Overlooks. Enjoy the lovely views and ample space to unwind and relax. Located just minutes from Bert T. Combs Mountain Parkway, this property offers both convenience and tranquility. Utilities are readily available at the road, allowing you to start planning your new home right

  Cathleen Gedeon CENTURY 21 Advantage Realty

  12651 Ironworks Rd, Winchester, KY 40391
• 

  

  /30

  Est $218,865 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft

  306 Sarah Ct, Winchester, KY 40391

  306 Sarah Ct, Winchester, KY 40391
• 

  

  /21

  $202,500

  • 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

  Kim Dice EXP Realty, LLC

  109 Quail Ridge Rd, Winchester, KY 40391
• 

  

  /38

  $250,000 Sold Jun 27, 2025

  • 1,768 Sq Ft
  • $141/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  214 Southwind Dr, Winchester, KY 40391

  This turnkey home is located in a superb established location. You will love the outdoor space with a large deck overlooking the huge fenced in backyard. The tastefully updated and well-maintained home sits on a .23-acre lot. The large completely renovated kitchen with stainless appliances is ready for the cooking enthusiast. New flooring has been installed throughout and professionally painted

  Tonya Skeens RE/MAX Elite Lexington

  214 Southwind Dr, Winchester, KY 40391
• 

  

  /29

  Est $291,868 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  455 Greenway Dr, Winchester, KY 40391

  455 Greenway Dr, Winchester, KY 40391
• 

  

  /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

  Kim Dice EXP Realty, LLC

  363 Silverton Way, Winchester, KY 40391
• 

  

  /58

  $850,000 Sold Jun 27, 2025

  • 2,980 Sq Ft
  • $285/SF
  • 1 Day On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  2158 Venable Rd, Winchester, KY 40391

  Perched upon 5.34 acres of flat land, this idyllic white farmhouse is ready to be loved by new owners! The property is fully fenced and has a gated entry. Step inside to an open floor plan with gleaming hardwoods throughout the main level. The family room with wood-burning stove flows into a spacious dining area. The beautifully renovated kitchen is complete with custom cabinetry, large walk-in

  Emily Miller Bluegrass Sotheby's International Realty

  2158 Venable Rd, Winchester, KY 40391
• 

  

  /25

  Est $248,337 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft

  316 Jameson Way, Winchester, KY 40391

  316 Jameson Way, Winchester, KY 40391
• 

  

  /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
• 

  

  /48

  $341,500 Sold Jun 27, 2025

  • 1,834 Sq Ft
  • $186/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

  401 Cedar Ct, Winchester, KY 40391

  Step into this beautifully updated 3-bedroom, 2-bath gem and fall in love with the perfect blend of charm and modern finishes! From the moment you walk through the door, you'll be greeted by an open concept living area with vaulted ceilings that fill the home with light and warmth.Enjoy new luxury vinyl plank flooring throughout the home, complemented by stylish, updated tile in the

  Geneva Wilder Selling the South Realty

  401 Cedar Ct, Winchester, KY 40391
• 

  

  /38

  Est $178,401 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,073 Sq Ft

  412 Jameson Way, Winchester, KY 40391

  412 Jameson Way, Winchester, KY 40391

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