Winchester, KY Homes for Sale

• 

  

  

  /103

  $2,650,000

  $345K PRICE DROP

  • 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
• 

  

  

  /57

  $350,000

  • 4 Beds
  • 2 Baths
  • 3,261 Sq Ft

  443 S Maple St, Winchester, KY 40391

  Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make

  Terra Long Keller Williams Commonwealth

  443 S Maple St, Winchester, KY 40391
• 

  

  /2

  $110,000

  • Land
  • 20,473 Sq Ft
  • $234,043 per Acre

  139 Jacob Ct, 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

  139 Jacob Ct, Winchester, KY 40391
• 

  

  

  /20

  $210,000

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft

  301 Snowden Dr, Winchester, KY 40391

  Charming all-brick ranch offering timeless character and everyday functionality! Step inside to a light-filled living room featuring beautiful hardwood floors and a warm, welcoming feel throughout. This home offers three bedrooms and one full bathroom, along with an eat-in kitchen perfect for casual dining and gathering. A dedicated laundry/mud room just off the kitchen provides convenient access

  Julia Lark The Brokerage

  301 Snowden Dr, Winchester, KY 40391
• 

  

  /2

  $150,000

  • Land
  • 2.11 Acres
  • $71,090 per Acre

  125 Knox Ct, 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

  125 Knox Ct, Winchester, KY 40391
• 

  

  /24

  $365,900

  New Construction $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
• 

  

  /16

  $124,500

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  122 Calloway St, Winchester, KY 40391

  Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

  Darrell Tackett Dream Maker Realty, LLC

  122 Calloway St, Winchester, KY 40391
• 

  

  /10

  $550,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  107 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  107 Bella Shae Way, Winchester, KY 40391
• 

  

  /8

  $1,500,000

  1015 Old Stone Church Rd, Winchester, KY 40391

  Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

  Walker Mack Bluegrass Property Exchange

  1015 Old Stone Church Rd, Winchester, KY 40391
• 

  

  /87

  $2,999,000

  $101K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 3,693 Sq Ft

  3049 Ironworks Rd, Winchester, KY 40391

  Some properties are special simply because of the story behind them. This 150-acre farm with 3,168 ft of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
• 

  

  /16

  $1,200,000

  • 16 Beds
  • 16 Baths
  • 7,480 Sq Ft

  16 Linden Ave, Winchester, KY 40391

  You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof

  Kevin Bradley KB Realty Group

  16 Linden Ave, Winchester, KY 40391
• 

  

  /29

  $344,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  23 Windridge Dr, Winchester, KY 40391

  Welcome home!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The

  Holly Goeing The Agency

  23 Windridge Dr, Winchester, KY 40391
• 

  

  /12

  $129,999

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  471 Goose Creek Rd, Winchester, KY 40391

  CASH BUYERS! This 3-bedroom, 2-bath manufactured home on 1.49 acres offers strong potential for those looking to renovate, rent, or resell. Property is being sold as-is and will require repairs, making it best suited for cash buyers. Located just minutes from I-64 and convenient to Lexington, this property combines rural privacy with accessibility — a desirable combination for future resale or

  Shari Frasure Keller Williams Commonwealth

  471 Goose Creek Rd, Winchester, KY 40391
• 

  

  /10

  $575,000

  $75K PRICE DROP

  • Land
  • 2.6 Acres
  • $221,154 per Acre

  529 Bullion Blvd Unit 3B, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Homes

  529 Bullion Blvd Unit 3B, Winchester, KY 40391
• 

  

  /11

  $50,000

  • Land
  • 17,859 Sq Ft
  • $121,951 per Acre

  308 Duclair Dr, Winchester, KY 40391

  Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

  Joseph Miller Keller Williams Legacy Group

  308 Duclair Dr, Winchester, KY 40391
• 

  

  /22

  $665,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  414 Alexis Way, Winchester, KY 40391

  Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

  Shane Underwood Keller Williams Commonwealth

  414 Alexis Way, Winchester, KY 40391
• 

  

  /9

  $785,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  425 Alexis Way, Winchester, KY 40391

  Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

  Shane Underwood Keller Williams Commonwealth

  425 Alexis Way, Winchester, KY 40391
• 

  

  /72

  $406,900

  New Construction

  • 3 - 6 Beds
  • 2.5 - 5.5 Baths
  • 2,570 Sq Ft

  Jackie Plan at Boone's Crossing, Winchester, KY 40391

  Unleash your creativity with the Jackie floor plan, a flexible and thoughtfully designed new construction home that empowers you to shape your ideal living space. Built by one of the most trusted home builders in Central Kentucky, the Jackie is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space, versatility, and modern

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824254, Winchester, KY 40391
• 

  

  /38

  $370,000

  $10K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 2,179 Sq Ft

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses , whatever you always dreamed of. Maybe just kicking back on the wrap around porch watching the

  Wayne Elkins RE/MAX Creative Realty

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /23

  $99,900

  • 3 Beds
  • 2 Baths
  • 675 Sq Ft

  2799 Pine Ridge Rd, Winchester, KY 40391

  If your looking for a fixer upper, this is it. House on 2 acres in the country with lots of potential. Laundry is off the kitchen, but floor is soft from a water leak. From the kitchen you will see a guest bath, dining and living area. To the left is a hallway that leads to 2 bedrooms, drywalled just needs to be finished. To the right of the living area is your master bedroom and bath. With some

  Robin Horn Keller Williams Commonwealth

  2799 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /13

  $239,900

  $7K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,007 Sq Ft

  221 S Highland St, Winchester, KY 40391

  INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered

  Joshua Lynch The Brokerage

  221 S Highland St, Winchester, KY 40391
• 

  

  /19

  $125,000

  $10K PRICE DROP

  • Land
  • 4.01 Acres
  • $31,172 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
• 

  

  /4

  $137,500

  • Land
  • 3.94 Acres
  • $34,898 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
• 

  

  /24

  $199,900

  • 3 Beds
  • 2 Baths
  • 915 Sq Ft

  225 Buffalo Trace, Winchester, KY 40391

  This move in ready ranch home offering 3 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC 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

  225 Buffalo Trace, Winchester, KY 40391
• 

  

  /17

  $398,000

  $66K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  104 Colby Hills Dr, Winchester, KY 40391

  Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

  Garry Milton Milton and Associates Real Estate

  104 Colby Hills Dr, Winchester, KY 40391
• 

  

  /24

  $239,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  125 Kittison Dr, Winchester, KY 40391

  Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable

  Kathryn Cheuvront Coldwell Banker McMahan

  125 Kittison Dr, Winchester, KY 40391
• 

  

  /3

  $84,900

  • Land
  • 3.39 Acres
  • $25,044 per Acre

  160 Rector Ln, Winchester, KY 40391

  UNIQUE Opportunity - 3.39 acres with a small pond - tucked away on a private lane, flat land and totally surrounded by trees. What a unique setting!! Convenience is the key to this property. Water is available at the main road. Internet has been extended down Rector Lane, electricity is accessible for connection. Deed Restrictions apply. Do Not Miss Your Chance to own this SPECIAL piece of land.

  M Gail Cleaver United Real Estate Bluegrass

  160 Rector Ln, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  Lot 3 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  Melia Hord MELIA Realty LLC

  Lot 3 Plantations Dr, Winchester, KY 40391
• 

  /2

  $110,000

  • Land
  • 13,939 Sq Ft
  • $343,750 per Acre

  250 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

  250 Duclair Dr, Winchester, KY 40391
• 

  

  /21

  $139,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
• 

  /2

  $188,500

  • Land
  • 12.1 Acres
  • $15,579 per Acre

  155 Spring Ridge Way, Winchester, KY 40391

  Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are- R-1E, 4000 sq. Ft lots for 80 lots R-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue. Please feel free to call the listing

  Jo Gawthrop Keller Williams Bluegrass Realty

  155 Spring Ridge Way, Winchester, KY 40391
• 

  

  /64

  $259,900

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft

  17 Holiday Rd, Winchester, KY 40391

  This classic brick ranch house is move-in ready and waiting for you to call it home! Take a step inside the front door to appreciate the gleaming laminate wood floors in the open concept living space. Around the corner, the beautiful kitchen cabinets and updated, stainless, kitchen appliances are ready for family meals and social gatherings around the dining table. In the full bath, you'll find a

  Josh Wood Freedom Realty & Property Management

  17 Holiday Rd, Winchester, KY 40391
• 

  

  /15

  $284,900

  $12K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,693 Sq Ft

  327 Newcastle Ln, Winchester, KY 40391

  PRICE REDUCTION!!! Perfect for investment or primary residence. Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase that overlooks the main floor. Upstairs are 3

  Huong Dunn Bluegrass Property Exchange

  327 Newcastle Ln, Winchester, KY 40391
• 

  

  /33

  $339,900

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  740 Pilot Ridge Ln, Winchester, KY 40391

  Tucked away on 1.25 fully fenced acres, this custom-built home offers some of the most breathtaking views in Winchester. Designed with charm and comfort in mind, this 3-bedroom, 2.5-bath home blends modern convenience with timeless farmhouse style. Step inside to an open, inviting layout filled with natural light and warm finishes throughout. The spacious vaulted master suite is a true retreat,

  Holly Goeing The Agency

  740 Pilot Ridge Ln, Winchester, KY 40391
• 

  /2

  $1,800,000

  $2M PRICE INCREASE

  • Land
  • 4.36 Acres
  • $412,844 per Acre

  722 Colby Rd Unit 1, Winchester, KY 40391

  Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

  Cheryl Johnston CMI Properties

  722 Colby Rd Unit 1, Winchester, KY 40391
• 

  

  /103

  $3,500,000

  $170K PRICE INCREASE

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 78-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
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 16,117 Sq Ft
  • $270,270 per Acre

  225 Jacob Ct, 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

  225 Jacob Ct, Winchester, KY 40391
• 

  

  /5

  $365,900

  New Construction $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
• 

  /2

  $195,000

  $2M PRICE DROP

  6699 Boonesboro Rd, Winchester, KY 40391

  READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

  Jennifer Ray RE/MAX Elite Lexington

  6699 Boonesboro Rd, Winchester, KY 40391
• 

  

  /3

  $670,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,261 Sq Ft

  113 Bella Shae Way, Winchester, KY 40391

  Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

  Shane Underwood Keller Williams Commonwealth

  113 Bella Shae Way, Winchester, KY 40391

Showing Results 41 - 80, Page 2 of 6