Winchester, KY Homes

• 

  

  

  /27

  $199,900 Sold Jul 15, 2025

  • 1,348 Sq Ft
  • $148/SF
  • 18 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1940

  139 W Hickman St, Winchester, KY 40391

  Welcome Home! Featuring 3 bedrooms and 2 bathrooms, this home is everything you have been looking for. Recent updates include new flooring, appliances, roof, HVAC, and even the water heater. Sit out on your front porch and drink your morning coffee, or enjoy your large back deck for a weekend cookout. This home also has plenty of attic storage. The driveway makes a perfect place to plug in your

  Clay David Sutherland ERA Select Real Estate

  139 W Hickman St, Winchester, KY 40391
• 

  

  

  /7

  Est $168,271 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,106 Sq Ft

  301 Hummingbird Rd, Winchester, KY 40391

  301 Hummingbird Rd, Winchester, KY 40391
• 

  

  

  /85

  $640,000

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft

  180 Casa Landa Way, Winchester, KY 40391

  This stately yet inviting residence in the highly desirable Stoney Brook subdivision offers the perfect blend of elegance and comfort. Thoughtfully designed for everyday living and entertaining, the home features generously sized rooms throughout.The main level includes formal living and dining spaces, a convenient half bath, and a beautifully appointed kitchen with granite countertops,

  Janna Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
• 

  

  

  /26

  $239,500 Sold Jul 15, 2025

  • 2,017 Sq Ft
  • $119/SF
  • 26 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  129 Bay Hill Dr, Winchester, KY 40391

  Located in an established neighborhood this low maintenance spacious townhome with over 2000 square foot has curb appeal and backs to a greenspace with a large backyard and rear facing garage. The home has been well maintained and updated with a new roof and new flooring. The kitchen and family room are nice sized for all your gatherings. For an added convenience the lower level offers a bonus

  Tonya Skeens RE/MAX Elite Lexington

  129 Bay Hill Dr, Winchester, KY 40391
• 

  

  

  /30

  Est $160,932 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  222 Locust Grove Rd, Winchester, KY 40391

  222 Locust Grove Rd, Winchester, KY 40391
• 

  

  /99

  $749,000

  • 4 Beds
  • 4 Baths
  • 4,644 Sq Ft

  110 Camelot Dr, Winchester, KY 40391

  Don't miss this rare opportunity to abide in one of Winchester's finest locations, Camelot Drive. A hidden gem tucked away in the back of Hampton Manor, this home boasts space and privacy on an idyllic cul-de-sac just off Boone Avenue. Details such as crown molding, built-in cabinetry, high ceilings, 2 fireplaces, transom windows, and hardwood floors fill this home with character and charm.

  Joyce Ratliff Tom Goebel & Company

  110 Camelot Dr, Winchester, KY 40391
• 

  

  /14

  $222,500 Sold Jul 15, 2025

  • 1,064 Sq Ft
  • $209/SF
  • 112 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  313 Vanover Way, Winchester, KY 40391

  Charming 3-bedroom, 2-bath brick home with both an attached and detached 1-car garage for added storage and convenience! This 1,064 sq ft home features a welcoming front entry with a ramp for easy access. Inside, enjoy a functional layout with comfortable living spaces. Outside, the detached garage offers extra workspace or storage. Conveniently located with easy access to I-64 and just minutes

  Bob Sophiea eXp Realty, LLC

  313 Vanover Way, Winchester, KY 40391
• 

  

  /31

  Est $220,579 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  208 Locust Grove Rd, Winchester, KY 40391

  208 Locust Grove Rd, Winchester, KY 40391
• 

  

  /58

  $525,000

  • 2 Beds
  • 1.5 Baths
  • 5,054 Sq Ft

  808 Bypass Rd, Winchester, KY 40391

  Unique Mixed-Use Opportunity! This versatile property offers prime potential for a restaurant, cafe, or retail space in a high-visibility location. The commercial space is turn key for a culinary venture or boutique business. Attached is a separate rental unit with private entrance, offering additional income or an ideal live/work setup. Additional space available for potential 2nd Apartment.

  Diana C Brooker Lifstyl Real Estate

  808 Bypass Rd, Winchester, KY 40391
• 

  

  /61

  $545,000 Sold Jul 15, 2025

  • 3,958 Sq Ft
  • $138/SF
  • 180 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2000

  1063 Wades Mill Rd, Winchester, KY 40391

  NEW ROOF INSTALLED MAY 28th. A fully remodeled 5-acre property offers a beautifully updated 3,958 sq ft home with 4 bedrooms, 3 full baths, and 1 half bath. Every inch of this spacious home has been thoughtfully updated, including brand-new flooring throughout and a newly installed HVAC unit upstairs for optimal comfort. The custom-designed primary closet provides a luxurious storage solution,

  Joseph Smallwood Christies International Real Estate Bluegrass

  1063 Wades Mill Rd, Winchester, KY 40391
• 

  

  /21

  Est $192,885 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 720 Sq Ft

  117 Spicer Rd, Winchester, KY 40391

  117 Spicer Rd, Winchester, KY 40391
• 

  /2

  $195,000

  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
• 

  

  /20

  $189,900 Sold Jul 14, 2025

  • 1,056 Sq Ft
  • $180/SF
  • 2 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  2342 Ironworks Rd, Winchester, KY 40391

  Welcome to 2342 Ironworks Road, where country charm meets effortless city access! Nestled on a lush, gently rolling lot, this brick ranch offers:Inviting Living Spaces: Original hardwood floors flow through a bright living room anchored by a classic painted-brick fireplace. The bonus room on the back side of the house would be ideal for a home office, nursery, or even a guest

  Dylan Justice GSP Homes

  2342 Ironworks Rd, Winchester, KY 40391
• 

  

  /15

  Est $181,637 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  223 Ecton Rd, Winchester, KY 40391

  223 Ecton Rd, Winchester, KY 40391
• 

  

  /4

  $100,000

  • Land
  • 2.62 Acres
  • $38,168 per Acre

  100 Spencer Ln, Winchester, KY 40391

  Eskippakithiki overlooks development. Has a 2.615 acre lot (parcel #8) available for sale waiting for you to build your dream home with beautiful views of serene countryside.

  Priscila Hale FC Tucker Bluegrass

  100 Spencer Ln, Winchester, KY 40391
• 

  

  /4

  $101,000 Sold Jul 14, 2025

  • Land
  • 4.02 Acres
  • $25,124 per Acre

  • 86 Days On Market

  2058 Athens Boonesboro Rd, Winchester, KY 40391

  Prime building lot - 4.15 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2058 and 2010 lots approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first

  Megan McCoy Keller Williams Legacy Group

  2058 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /28

  Est $253,509 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  273 Ecton Rd, Winchester, KY 40391

  273 Ecton Rd, Winchester, KY 40391
• 

  

  /32

  $399,500

  750 Providence Ln, Winchester, KY 40391

  Welcome to your own slice of country paradise tucked away in southern Clark County! This 51+ acre tract offers a mixture of cleared pasture and mature woods, ideal for a variety of uses including cattle, crops, horses, recreation, or even your dream home site. Currently enjoyed as a private recreational family farm, the property already has electricity in place and features a cistern at an old

  Michelle Blackburn RE/MAX Creative, Winchester

  750 Providence Ln, Winchester, KY 40391
• 

  

  /58

  $232,500 Sold Jul 12, 2025

  • 1,161 Sq Ft
  • $200/SF
  • 235 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1980

  114 Holiday Rd, Winchester, KY 40391

  Price Improvement!Charming Brick Ranch Home in Holiday HillsWelcome to this inviting 1161 sq ft brick ranch home, lovingly maintained by the same family since 1980. Nestled in the desirable Holiday Hills subdivision, this property offers comfort and convenience with easy access to Wiseman Park.Inside, you'll find a cozy spacious living area that features beautiful hardwood

  Karen Smith Emmerich Muzic Realty

  114 Holiday Rd, Winchester, KY 40391
• 

  

  /18

  Est $156,300 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  108 Crawford Ave, Winchester, KY 40391

  108 Crawford Ave, Winchester, KY 40391
• 

  

  /80

  $524,000

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft

  160 Agawam Rd, Winchester, KY 40391

  Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-acre fenced lot. This versatile property offers the perfect blend of comfort, functionality, and rural charm - ideal for families, hobby farmers, or equestrian enthusiasts. Inside, you'll find 3 bedrooms and 3 bathrooms with a fully finished basement that offers ample space for additional bedrooms, a home gym,

  Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
• 

  

  /58

  $460,000 Sold Jul 11, 2025

  • 4,448 Sq Ft
  • $103/SF
  • 18 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1978

  150 Stone Crest Rd, Winchester, KY 40391

  IMMEDIATE OCCUPANCY! WELCOME HOME with Room to spread out in this SPACIOUS Home of over 4000 sq. ft. sitting on 5.5 Acres! Offering 4 Bedrooms, 4 Bathrooms, Living Room, Beautiful Kitchen with appliances and tons of cherry cabinets, Den, utility room and 2 Large Bonus Rooms in the Basement. one could be a bedroom. There is a 3-car Detached Garage, 2-car attached Garage, Large Carport, Huge Patio

  Brenda Murphy Murphy Realty Group

  150 Stone Crest Rd, Winchester, KY 40391
• 

  

  /55

  Est $168,627 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  30 Ashland Ave, Winchester, KY 40391

  30 Ashland Ave, Winchester, KY 40391
• 

  

  /5

  $125,000

  • Land
  • 2.5 Acres
  • $50,000 per Acre

  1200 Craig Crossing, Winchester, KY 40391

  Welcome to Lot #18 in prestigious Thoroughbred Estates, an exceptional 2.5-acre corner parcel of gently rolling countryside, graced by a serene stream and picturesque views. This remarkable homesite offers the perfect canvas for your custom estate in one of western Clark County's most coveted locations, just off the highly sought-after McClure Road. A rare opportunity to claim a piece of

  N Seth Parker Lifstyl Real Estate

  1200 Craig Crossing, Winchester, KY 40391
• 

  

  /27

  $207,500 Sold Jul 11, 2025

  • 1,385 Sq Ft
  • $150/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1970

  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
• 

  

  /32

  Est $186,975 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,900 Sq Ft

  203 Crawford Ct, Winchester, KY 40391

  203 Crawford Ct, Winchester, KY 40391
• 

  /2

  $14,100,000

  • Land
  • 274.52 Acres
  • $51,362 per Acre

  2395 Paris Rd, Winchester, KY 40391

  NOW PRE-SELLING: Deerlawn Development is Winchester, Ky's most anticipated residential development—an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods.
 Located at 2395 Paris Road, and positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 single-family

  Melia Hord Keller Williams Bluegrass Realty

  2395 Paris Rd, Winchester, KY 40391
• 

  

  /21

  $259,900 Sold Jul 10, 2025

  • 1,321 Sq Ft
  • $197/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  302 April Way, Winchester, KY 40391

  This 3-bedroom, 2 full bath home is quietly located just off the Winchester Bypass. While convenient location may be obvious, updates can be seen throughout. Including stainless appliances, LVP flooring, new roof less than 1 year. With spacious yard, family room and sizeable master on-suite, this home may be what you have been waiting for. Schedule your showing today!

  Michael Hilario The Agency

  302 April Way, Winchester, KY 40391
• 

  

  /53

  Est $195,164 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,631 Sq Ft

  29 Fairview Ave, Winchester, KY 40391

  29 Fairview Ave, Winchester, KY 40391
• 

  

  /9

  $102,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  39 S Highland St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This Single Family home has 2 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  39 S Highland St, Winchester, KY 40391
• 

  

  /3

  $554,651 Sold Jul 10, 2025

  • 2,400 Sq Ft
  • $231/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  426 Alexis Way, Winchester, KY 40391

  Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

  Shane Underwood Keller Williams Commonwealth

  426 Alexis Way, Winchester, KY 40391
• 

  

  /29

  Est $164,638 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  4 Sylvania Ave, Winchester, KY 40391

  4 Sylvania Ave, Winchester, KY 40391
• 

  

  /12

  $144,000

  • 3 Beds
  • 1 Bath
  • 805 Sq Ft

  150 Cook Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This has a single family has 3 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  150 Cook Ave, Winchester, KY 40391
• 

  

  /22

  $220,000 Sold Jul 08, 2025

  • 1,210 Sq Ft
  • $182/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  122 Spruce Ct, Winchester, KY 40391

  RENOVATED Brick Ranch Home * 3 Bedrooms, 2 Full Baths, plus separate Laundry Room, Deck and Covered Front Porch! Updates in 2022 include: Tall White Kitchen Cabinets, Tile Backsplash, New Countertops, Sink, Faucet & Stainless Appliances * Primary Suite with Spacious Closet, New Vanity and Tiled Walk-in Shower with Body Sprayer Shower System * Guest Bath with New Vanity and Tiled Bathtub Area *

  Christal Browning Four Seasons Realty

  122 Spruce Ct, Winchester, KY 40391
• 

  

  /22

  Est $193,043 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,016 Sq Ft

  21 Sylvania Ave, Winchester, KY 40391

  21 Sylvania Ave, Winchester, KY 40391
• 

  

  /6

  $388,000

  • 5 Beds
  • 3 Baths
  • 2,762 Sq Ft

  101 E Lexington Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  101 E Lexington Ave, Winchester, KY 40391
• 

  

  /32

  $285,000 Sold Jul 03, 2025

  • 1,690 Sq Ft
  • $169/SF
  • 168 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1976

  602 Laura Dr, Winchester, KY 40391

  MOTIVATED SELLERS. Find peace in this updated all-brick ranch that's made for summer fun and year-round comfort — complete with an in-ground pool, walk-out basement, and a backyard that's calling for your next BBQ. Tucked in a quiet neighborhood just over the Fayette County line, you're only 10 minutes from Hamburg, giving you the best of both convenience and calm.Inside, this 3 bedroom,

  Ryan O'Gara Real Broker, LLC

  602 Laura Dr, Winchester, KY 40391
• 

  

  /30

  Est $195,324 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft

  280 Winn Ave, Winchester, KY 40391

  280 Winn Ave, Winchester, KY 40391
• 

  

  /17

  $1,350,000

  16 Linden Ave, Winchester, KY 40391

  Income-Producing 16-Unit Apartment complex in the Heart of WinchesterTurn-key opportunity on North Maple Avenue—just minutes from Downtown Winchester and a quick 20-minute drive to Lexington via I-64. Consisting of sixteen one-bed/one-bath apartments on a 0.34-acre lot with 20 parking spaces, the property has a 2022 new roof, new vinyl siding added in 2023, and several fully

  Patrick Doyle National Real Estate

  16 Linden Ave, Winchester, KY 40391
• 

  

  /28

  $265,000 Sold Jul 02, 2025

  • 1,305 Sq Ft
  • $203/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1980

  609 Clintonville Rd, Winchester, KY 40391

  Location, location, location! This house is located on a .48 Kentucky Bluegrass lot in a residential neighborhood, Wayland Heights. And within minutes you can be at the Hamburg area of Lexington or to the Historical Downtown Winchester. The owners of this home remodeled interior, added new windows, gutters and facia trim and painted the exterior of the house. The great room is a welcoming space

  Craig Bridgewater Bridgewater Real Estate

  609 Clintonville Rd, Winchester, KY 40391

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