Homes in ZIP Code 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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /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
• 

  

  /38

  Est $138,005 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft

  114 Magnolia St, Winchester, KY 40391

  114 Magnolia St, 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
• 

  

  /24

  Est $171,531 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,248 Sq Ft

  121 Magnolia St, Winchester, KY 40391

  121 Magnolia St, 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
• 

  

  /22

  Est $153,367 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,596 Sq Ft

  108 4th St, Winchester, KY 40391

  108 4th St, 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
• 

  

  /19

  Est $120,800 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,078 Sq Ft

  40 6th St, Winchester, KY 40391

  40 6th St, Winchester, KY 40391
• 

  

  /8

  $129,000

  • 2 Beds
  • 1 Bath
  • 637 Sq Ft

  109 Spring St, Winchester, KY 40391

  Investment opportunity in Winchester! This 2-bedroom, 1-bath home at 109 Spring St is currently tenant-occupied and leased at $900/month. Functional layout with a spacious kitchen and separate living area. Conveniently located near downtown, schools, and local amenities. Whether you're expanding your portfolio or looking for a starter investment, this property offers steady rental income from day

  Shari Frasure Keller Williams Commonwealth

  109 Spring St, 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
• 

  

  /30

  Est $222,619 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,570 Sq Ft

  13 7th St, Winchester, KY 40391

  13 7th St, Winchester, KY 40391
• 

  

  /42

  $635,000

  • 6 Beds
  • 3.5 Baths
  • 5,227 Sq Ft

  439 Lynnway Dr, Winchester, KY 40391

  --Contingent Offer w/ 72hr Kick-Out in place--Welcome to 439 Lynnway, an expansive 5,000+ sq ft home, where every inch was designed for comfort, style, and entertainment. The main floor features a primary en-suite, office space, and laundry area. As you make your way upstairs, you will find spacious bedrooms throughout. New roof placed early 2025.The finished basement is a standout,

  Reagan Rainey Dream Maker Realty, LLC

  439 Lynnway Dr, 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
• 

  

  /36

  Est $213,292 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  11 Meadow St, Winchester, KY 40391

  11 Meadow St, Winchester, KY 40391
• 

  

  /5

  $29,000

  • Land
  • 0.46 Acre
  • $63,043 per Acre

  102 Augusta Dr, Winchester, KY 40391

  This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

  Dale Hatton Dream Maker Realty, LLC

  102 Augusta Dr, Winchester, KY 40391
• 

  

  /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
• 

  

  /3

  Est $221,168 Not Listed For Sale

  • 2 Beds

  28 Denny Ave, Winchester, KY 40391

  28 Denny Ave, Winchester, KY 40391
• 

  

  /62

  $269,950

  • 3 Beds
  • 2 Baths
  • 1,247 Sq Ft

  3614 Stamper Dr, Winchester, KY 40391

  Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, 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
• 

  

  /3

  Est $227,585 Not Listed For Sale

  • 2 Beds

  30 Denny Ave, Winchester, KY 40391

  30 Denny Ave, Winchester, KY 40391
• 

  /2

  $240,000

  • Land
  • 12 Acres
  • $19,835 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 lotsR-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
• 

  

  /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
• 

  /2

  Est $228,990 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,214 Sq Ft

  106 Spruce Ct, Winchester, KY 40391

  106 Spruce Ct, Winchester, KY 40391
• 

  

  /3

  $40,000

  • Land
  • 0.19 Acre
  • $210,526 per Acre

  113 Mayfair Ct, Winchester, KY 40391

  Wowser! Looking for a lot that backs up to greenspace and will NOT have another home on one side? Here it IS! This may be just what you're looking for. Originally, the street was supposed to connect, but due to the changes in grade, this won't be happening! Plus, with the way the lot sits, you can enjoy many beautiful sunsets. It's a hidden gem just waiting for you to find it! The home to

  Jo Gawthrop Keller Williams Bluegrass Realty

  113 Mayfair Ct, Winchester, KY 40391
• 

  

  /22

  $88,000 Sold May 08, 2025

  • 2,363 Sq Ft
  • $37/SF
  • 23 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1878

  423 E Broadway St, Winchester, KY 40391

  Absolute Auction-Selling to the Highest Bidder Regardless of Listing Price. Live On-Site Saturday April 19th at 10:00 a.m. Contracted to sell at Absolute Auction Only! Offers Prior to Auction Will Not Be Entertained. Visit for Bidder & Agent Registration forms and Complete Terms & Conditions. Don't miss this great opportunity to own this Beautiful, Very Large downtown Winchester property.

  Tanya M M Miller Bluegrass Auction, Appraisal & Realty, LLC

  423 E Broadway St, Winchester, KY 40391
• 

  

  /25

  Est $209,803 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft

  212 Forest Ct, Winchester, KY 40391

  212 Forest Ct, Winchester, KY 40391
• 

  /2

  $40,000

  • Land
  • 0.26 Acre
  • $153,846 per Acre

  105 Bella Ct, Winchester, KY 40391

  Vacant Lot in a quiet cul-de-sac

  Jo Gawthrop Keller Williams Bluegrass Realty

  105 Bella Ct, Winchester, KY 40391
• 

  

  /17

  $175,000 Sold May 07, 2025

  • 1,228 Sq Ft
  • $143/SF
  • 1 Day On Market

  • 2 Beds
  • 1 Bath
  • Built 1940

  220 Jackson St, Winchester, KY 40391

  Welcome to this beautifully remodeled 2-bedroom home with a bonus room that could easily serve as a third bedroom or office space. Fall in love with the fresh, modern updates throughout—from the stylish flooring to the bright, spacious kitchen that is perfect for cooking. Outside, you'll find a cozy patio for relaxing evenings and a huge backyard with room to entertain, garden or play. No need to

  Joanna Howell Bluegrass Properties Group

  220 Jackson St, Winchester, KY 40391
• 

  

  /55

  Est $204,008 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,026 Sq Ft

  220 W Clark Dr, Winchester, KY 40391

  220 W Clark Dr, Winchester, KY 40391
• 

  /2

  $42,500

  • Land
  • 0.20 Acre
  • $212,500 per Acre

  108 Dorset Ln, Winchester, KY 40391

  The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

  Jo Gawthrop Keller Williams Bluegrass Realty

  108 Dorset Ln, Winchester, KY 40391
• 

  

  /37

  $228,000 Sold May 02, 2025

  • 1,247 Sq Ft
  • $183/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1962

  102 E Clark Dr, Winchester, KY 40391

  OPEN HOUSE SCHEDULED FOR Sunday, March 2nd has been CANCELLED since the home is now under contract. Looking for a move-in ready brick ranch home that's in pristine condition? Well, look no further! LOTS of updates! Some of the features of this 3 bedroom / 1.5 bath home include gleaming hardwood flooring, recently replaced HVAC system (the entire system), new gas water heater, and a separate

  Jim Woodrum RE/MAX Creative, Winchester

  102 E Clark Dr, Winchester, KY 40391
• 

  

  /20

  Est $207,029 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,065 Sq Ft

  224 W Robinson Ct, Winchester, KY 40391

  224 W Robinson Ct, Winchester, KY 40391

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