Winchester, KY Homes

• 

  

  

  /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
• 

  

  

  /20

  Est $203,488 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,593 Sq Ft

  4 Hiawatha Trail, Winchester, KY 40391

  4 Hiawatha Trail, Winchester, KY 40391
• 

  

  

  /14

  $319,975

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft

  1363 Clintonville Rd, Winchester, KY 40391

  Embrace the potential of this 5-acre gem near Winchester and Hamburg, KY. Located in beautiful Clark County, this fixer-upper boasts 2 bedrooms, 1 bath, and scenic farm views on flat, versatile land perfect for building or farming. The property features a long driveway and a detached 2-car garage, ideal for creating a smaller homestead. Enjoy the tranquility of country living with the convenience

  Rebakah Goodpaster Keller Williams Legacy Group

  1363 Clintonville Rd, 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
• 

  

  

  /38

  Est $256,490 Not Listed For Sale

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

  116 Dixon Way, Winchester, KY 40391

  116 Dixon Way, Winchester, KY 40391
• 

  

  /4

  $334,327 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,997 Sq Ft

  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
• 

  

  /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
• 

  

  /26

  Est $183,051 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,030 Sq Ft

  306 Hummingbird Rd, Winchester, KY 40391

  306 Hummingbird Rd, Winchester, KY 40391
• 

  

  /48

  $339,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft

  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 kitchen and

  Geneva Wilder Selling the South Realty

  401 Cedar Ct, 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
• 

  

  /21

  Est $170,772 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,102 Sq Ft

  117 Spicer Rd, Winchester, KY 40391

  117 Spicer Rd, Winchester, KY 40391
• 

  

  /4

  $315,000

  • Land
  • 49 Acres
  • $6,487 per Acre

  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 the

  Mila Ensor Ensor Real Estate LLC

  4550 Schollsville Rd Unit 40391, 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
• 

  

  /17

  Est $142,246 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,096 Sq Ft

  431 E Broadway St, Winchester, KY 40391

  431 E Broadway St, Winchester, KY 40391
• 

  

  /23

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  26 Stefanie Ct, Winchester, KY 40391

  Welcome to this charming 3BR-1BA brick ranch nestled in a quiet court in Winchester. The home features classic hardwood flooring throughout, offering timeless style and easy maintenance. Outback you will enjoy a fenced in yard and a detached 1 car garage. Don't miss the opportunity to own a move-in-ready gem. Call today for your showing.

  Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391
• 

  

  /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
• 

  

  /15

  Est $178,265 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  223 Ecton Rd, Winchester, KY 40391

  223 Ecton Rd, Winchester, KY 40391
• 

  

  /27

  $214,900

  • 3 Beds
  • 1 Bath
  • 1,385 Sq Ft

  2350 Ironworks Rd, Winchester, KY 40391

  Escape to the country with the perfect blend of space, privacy, and convenience at 2350 Ironworks Rd. Nestled on a generous lot just minutes from downtown Winchester and a short drive to Lexington, this charming 3-bedroom, 1-bath home offers the peaceful feel of rural living without sacrificing accessibility. Step inside to find an inviting living space with natural light, original hardwood

  Dylan Justice GSP Homes

  2350 Ironworks 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
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  /28

  Est $239,662 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  273 Ecton Rd, Winchester, KY 40391

  273 Ecton Rd, Winchester, KY 40391
• 

  

  /24

  $300,000

  • 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
• 

  

  /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
• 

  

  /27

  Est $223,347 Not Listed For Sale

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

  410 E Broadway St, Winchester, KY 40391

  410 E Broadway St, Winchester, KY 40391
• 

  

  /44

  $839,000

  • 5 Beds
  • 3.5 Baths
  • 3,384 Sq Ft

  150 Jones Nursery Rd, Winchester, KY 40391

  Experience the perfect blend of modern comfort and country charm in this stunning 4-bedroom, 3.5-bathroom Craftsman-style home, built in 2018. Nestled on 2.58 acres of scenic countryside, this property offers the serenity of rural living with convenient access to Lexington.Designed for both style and functionality, the spacious interior features a chef's kitchen with custom countertops, a large

  Joshua Davis The Agency

  150 Jones Nursery Rd, Winchester, KY 40391
• 

  

  /24

  $207,000 Sold May 12, 2025

  • 1,040 Sq Ft
  • $199/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2023

  411 Pueblo Ct, Winchester, KY 40391

  Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the desirable Ft. Estill neighborhood in Winchester. Only 2 years old, this home offers peace of mind with all major systems—including HVAC, roof, and water heater—just 2 years young. Enjoy an open, functional layout perfect for modern living, with spacious bedrooms and a comfortable primary suite.Situated in a quiet,

  Zach Johnson The Brokerage

  411 Pueblo Ct, Winchester, KY 40391
• 

  

  /9

  Est $210,112 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,192 Sq Ft

  415 E Broadway St, Winchester, KY 40391

  415 E Broadway St, Winchester, KY 40391
• 

  

  /43

  $290,000

  • 4 Beds
  • 2 Baths
  • 1,475 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
• 

  

  /22

  $90,000 Sold May 12, 2025

  • Land
  • 3.49 Acres
  • $25,788 per Acre

  • 50 Days On Market

  9776 Ironworks Rd, Winchester, KY 40391

  Beautiful piece of land to build your dream Barndominium, house, tiny house, manufactured home, workshop, whatever meets county regulations. No deed restrictions! 40' x 60' x 16' pole barn style garage / home already started for you! An older barn with stalls for the animals! Barn needs a little love. Approximately 515 feet of road frontage. Current access to property is a small easement from the

  Jason Townsend Kentucky Residential Real Estate, LLC

  9776 Ironworks Rd, Winchester, KY 40391
• 

  

  /18

  Est $148,899 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  108 Crawford Ave, Winchester, KY 40391

  108 Crawford Ave, Winchester, KY 40391
• 

  

  /63

  $1,950,000

  • Land
  • 55 Acres
  • $35,455 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
• 

  

  /21

  $207,000 Sold May 12, 2025

  • 1,344 Sq Ft
  • $154/SF
  • 35 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2001

  513 Acadia Way, Winchester, KY 40391

  This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of AMI for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  513 Acadia Way, Winchester, KY 40391
• 

  

  /30

  Est $171,497 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft

  280 Winn Ave, Winchester, KY 40391

  280 Winn Ave, Winchester, KY 40391
• 

  

  /34

  $220,000

  • 2 Beds
  • 1 Bath
  • 1,013 Sq Ft

  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, 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 unfinished basement! Plenty of parking with very

  Jason Townsend Kentucky Residential Real Estate, LLC

  42 Wheeler Ave, Winchester, KY 40391
• 

  

  /22

  $173,000 Sold May 09, 2025

  • 1,287 Sq Ft
  • $134/SF
  • 1 Day On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  160 Autumn Ct, Winchester, KY 40391

  Attention Investors, Flippers & First-Time Buyers! This 2-bedroom, 1-bath home is bursting with potential! Whether you're looking to renovate and resell, add to your rental portfolio, or put your personal touch on your first home, this is the opportunity you've been waiting for. With solid bones and a great layout, a little modernizing will go a long way in maximizing its value.Outside, the

  Phillip Neeley-Morrison Bluegrass Home Group

  160 Autumn Ct, Winchester, KY 40391
• 

  

  /10

  Est $187,258 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,230 Sq Ft

  282 Winn Ave, Winchester, KY 40391

  282 Winn 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
• 

  

  /21

  $199,500 Sold May 09, 2025

  • 1,539 Sq Ft
  • $130/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  445 Colby Ridge Blvd, Winchester, KY 40391

  Spacious 3 bedroom duplex townhome in the Heart of Winchester! This beautifully maintained 3 bedroom, 2.5 bath townhome offers the perfect blend of space, convenience and comfort right in the heart of Winchester. The main level features a large living room, ideal for relaxing or entertaining, along with a spacious kitchen & dining area that offers plenty of room for cooking & gathering, along

  Mary Layton FC Tucker Bluegrass

  445 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /21

  Est $145,943 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  48 Watts Rd, Winchester, KY 40391

  48 Watts Rd, 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
• 

  

  /40

  $206,000 Sold Apr 29, 2025

  • 1,053 Sq Ft
  • $196/SF
  • 25 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1970

  194 Spruce Ct, Winchester, KY 40391

  Beautiful remodeled home. Enjoy this ready to move in home, all you need is your keys! Sold as is, inspections welcome. Agent owner. Brick Ranch, 3 Bedrooms, 1 Full Bath, with Attached 2 Car Garage. Home Features Over 1050 sq ft with Spacious Living Room, Eat In Kitchen with Dishwasher, Stove and Refrigerator and Adjoining Utility Space with Washer/Dryer Hook Up. HVAC is less than 2 years old.

  Peggy Baldridge HomeFirst Real Estate

  194 Spruce Ct, Winchester, KY 40391

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