Winchester, KY Homes

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  /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
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  /19

  $220,000 Sold Apr 23, 2025

  • 1,200 Sq Ft
  • $183/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  112 Central Ave, Winchester, KY 40391

  NEW CONSTRUCTION! Located just steps from Winchester's charming downtown area, you'll have access to shops, restaurants, local events and more. This beautiful home offers 3 bedrooms, 2 baths, sleek modern kitchen with granite counter tops and stainless still appliances. At $217,000, this home offers unbeatable value for a brand-new construction in a well-established neighborhood in downtown

  Nena Honaker Tom Goebel & Company

  112 Central Ave, Winchester, KY 40391
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  /27

  Est $243,327 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,626 Sq Ft

  116 Alabama St, Winchester, KY 40391

  116 Alabama St, Winchester, KY 40391
• 

  

  

  /50

  $989,000

  • 4 Beds
  • 2.5 Baths
  • 2,670 Sq Ft

  1110 Craig Crossing, Winchester, KY 40391

  Discover timeless elegance and modern luxury in this newly constructed residence, perfectly situated on over 2.5 acres in Winchester. With 2,670 sq ft of custom designed living space, this 4-bedroom, 2.5-bath home offers craftsmanship, high-end finishes, and exceptional outdoor living. White oak engineered hardwood flooring, moulding throughout, and exquisite details. The spacious great room

  Michael Hilario The Agency

  1110 Craig Crossing, Winchester, KY 40391
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  /29

  $385,000 Sold Apr 21, 2025

  • 2,800 Sq Ft
  • $138/SF
  • 25 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1982

  1623 Little Stoner Rd, Winchester, KY 40391

  A ranch house on a basement with 7 Acres sounds like an ideal setup for someone who wants space, privacy, and the potential for a variety of activities! The combination of a ranch-style home and basement gives you flexibility-whether it's extra storage, living space, or even a potential hobby area. A Must See!

  Sharon Ben David Berkshire Hathaway de Movellan Properties

  1623 Little Stoner Rd, Winchester, KY 40391
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  /35

  Est $282,023 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,769 Sq Ft

  8 French Ave, Winchester, KY 40391

  8 French Ave, Winchester, KY 40391
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  /69

  $995,000

  • 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
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  /19

  $175,000 Sold Apr 18, 2025

  • 1,188 Sq Ft
  • $147/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  11 Shelley Dr, Winchester, KY 40391

  Investors take a look! 3 bedrooms, 2 bathrooms brick ranch on full unfinished basement with large 2 car detached garage & large, covered patio on back of home. Hardwood flooring, updated bathrooms, one with walk-in shower, newer roof and newer HVAC system. Home is selling As-Is but inspections are welcome.

  Tonya Morrow KY Local

  11 Shelley Dr, Winchester, KY 40391
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  /71

  Est $290,541 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,402 Sq Ft

  16 French Ave, Winchester, KY 40391

  16 French Ave, Winchester, KY 40391
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  /54

  $540,000

  • 3 Beds
  • 2.5 Baths
  • 2,020 Sq Ft

  1778 Elkin Rd, Winchester, KY 40391

  Peaceful Living on 8.83 aces of gently rolling hills in the heart of Kentucky. Breathtaking countryside features a charming home that offers peace, privacy and serene surroundings. Whether you're dreaming of a small hobby farm, a quiet artist retreat or just want space to breathe. This is the place. Wake up to birdsong, watch deer wander at dusk and soak in the golden sunsets from your own

  Valeria Kaidanov Pacesetters Real Estate

  1778 Elkin Rd, Winchester, KY 40391
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  /27

  $190,000 Sold Apr 18, 2025

  • 1,550 Sq Ft
  • $123/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1969

  7 Pocahontas Trail, Winchester, KY 40391

  Step inside this raised ranch, sun filled rooms, hardwood in most of the upstairs, kitchen with all the appliances, washer/dryer stay, large detached garage, hot tub on covered deck, great space in back yard, some fencing, lovely home close to historic downtown Winchester, not far from I-75 and I-64, shopping, church, schools, large partial finished walkout basement, call today this one won't

  Mila Ensor Ensor Real Estate LLC

  7 Pocahontas Trail, Winchester, KY 40391
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  /36

  Est $232,120 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,116 Sq Ft

  250 S Highland St, Winchester, KY 40391

  250 S Highland St, Winchester, KY 40391
• 

  

  /15

  $135,000

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  706 Williamsburg Dr, Winchester, KY 40391

  This is your opportunity to buy a brand new Clayton tru elation single wide mobile home. 3 bed 2 bath all electric. The .11 acre lot conveys. New front porch and back steps. This house is in the Yorktown trailer park. They currently have an HOA fee of $150 a month and that covers your water, sewer, and trash. The park also offers a play ground for the kids. Please confirm you read over all park

  Andrew Fugitt Coldwell Banker McMahan

  706 Williamsburg Dr, Winchester, KY 40391
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  /87

  $250,000 Sold Apr 18, 2025

  • 1,680 Sq Ft
  • $149/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1996

  418 Jameson Way, Winchester, KY 40391

  Welcome to this charming split-level home in Maple Ridge subdivision! Designed with comfort and convenience in mind, this home features an updated eat-in kitchen with granite countertops, an all purpose kitchen island that fits 2 barstools and a stylish tiled backsplash. All bedrooms are on the first level, complete with your very own primary bathroom. The inviting living room offers a cozy

  Josh Wood Freedom Realty & Property Mgt

  418 Jameson Way, Winchester, KY 40391
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  /29

  Est $229,533 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft

  144 E Broadway St, Winchester, KY 40391

  144 E Broadway St, Winchester, KY 40391
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  /9

  $210,000

  • Land
  • 8 Acres
  • $27,027 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
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  /49

  $442,500 Sold Apr 18, 2025

  • 3,882 Sq Ft
  • $114/SF
  • 134 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 2005

  321 Frontier Way, Winchester, KY 40391

  OPEN HOUSE Saturday 3/1/25 2-4pm. Apart from home being in a great location, right across the street from the Elementary School, home is minutes from shopping, food and entertainment (Applebees,Woody's Bar and Grill, Tjmaxx, Kroger, Movie Theatre, Ft. Boonesborough) & only a 20 minute drive to Hamburg in Lexington or 15 miutes to Mt. Sterling. This beautiful home is complete with a newly finished

  Olivia White Deborah Ball Realty

  321 Frontier Way, Winchester, KY 40391
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  /8

  Est $143,752 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 984 Sq Ft

  12 Buckner St, Winchester, KY 40391

  12 Buckner St, Winchester, KY 40391
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  /73

  $850,000

  • 5 Beds
  • 3 Baths
  • 3,664 Sq Ft

  1183 the Ridings Rd, Winchester, KY 40391

  This beautiful 5 bedroom 3 full bath home sits on 5 acres in The Ridings at Colby. This neighborhood has horseback riding trails throughout & is a 15 minute drive to the Hamburg/Lexington area. Large eat in kitchen with island, granite countertops & stainless steel appliances. Entertain in your custom dining room featuring a tray ceiling & wainscoting, or on your covered outdoor Trex deck. Relax

  Libby VanMeter Marshall Lane Real Estate - Lexington

  1183 the Ridings Rd, Winchester, KY 40391
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  /2

  $110,000 Sold Apr 18, 2025

  • Land
  • 0.59 Acre
  • $186,441 per Acre

  • 847 Days On Market

  210 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

  210 Duclair Dr, Winchester, KY 40391
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  /17

  Est $153,689 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 956 Sq Ft

  30 Rowland Ave, Winchester, KY 40391

  30 Rowland Ave, Winchester, KY 40391
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  /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
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  /34

  $260,000 Sold Apr 17, 2025

  • 1,565 Sq Ft
  • $166/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  597 Marseille Blvd, Winchester, KY 40391

  Welcome to this 3-bedroom, 2-bathroom ranch-style home conveniently located off McClure Road in a desirable neighborhood, perfect for those looking to create their dream space. The layout features a spacious yet cozy living area with a fireplace and a functional kitchen, ready for your personal touch. Step outside to a large fenced backyard that's perfect for outdoor activities, pets, or

  Michelle Blackburn RE/MAX Creative, Winchester

  597 Marseille Blvd, Winchester, KY 40391
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  /16

  Est $187,201 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,442 Sq Ft

  10 Rowland Ave, Winchester, KY 40391

  10 Rowland Ave, Winchester, KY 40391
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  /26

  $244,700

  • 3 Beds
  • 2.5 Baths
  • 2,017 Sq Ft

  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
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  /17

  $390,000 Sold Apr 16, 2025

  • 1,854 Sq Ft
  • $210/SF
  • 73 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1983

  3750 Becknerville Rd, Winchester, KY 40391

  Are you longing for a quiet country home? A place to have a few farm animals, raise a garden and enjoy the peacefulness of living away from town. Presenting to you 3750 Becknerville Road. It checks all of the boxes! This lovely 5.5 acre mini farm is situated between Winchester and Lexington on a gorgeous, partially fenced tract, with amazing mature trees. With roughly 1850 square feet of living

  Holly Goeing The Agency

  3750 Becknerville Rd, Winchester, KY 40391
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  /19

  Est $145,109 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,081 Sq Ft

  43 Jackson St, Winchester, KY 40391

  43 Jackson St, Winchester, KY 40391
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  /33

  $184,900

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  307 Blair Ave, Winchester, KY 40391

  This charming 3-bedroom, 1-bath ranch offers fresh updates throughout, including brand new flooring and interior paint. The inviting side porch features a ramp for easy accessibility and leads to a spacious patio—perfect for relaxing or entertaining. A detached two-car garage adds great storage and functionality. Located just minutes from downtown Winchester and I-64, this move-in-ready home

  Brooke Otis-Mull RO&CO Real Estate

  307 Blair Ave, Winchester, KY 40391
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  /17

  $278,000 Sold Apr 15, 2025

  • 1,292 Sq Ft
  • $215/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  218 Bracken Ct, Winchester, KY 40391

  Since warm weather is near you will love the updated huge back deck with new railing overlooking a large, fenced backyard. This spacious turnkey open concept 3-bedroom 2-bath home sitting on a .29-acre lot has been completely updated and ready for you to move in and enjoy. Since it is located in a cul-de-sac no worries regarding busy traffic. This budget friendly home has a newer roof less than

  Tonya Skeens RE/MAX Elite Lexington

  218 Bracken Ct, Winchester, KY 40391
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  /61

  Est $256,736 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,318 Sq Ft

  229 E Broadway St, Winchester, KY 40391

  229 E Broadway St, Winchester, KY 40391
• 

  

  /20

  $289,000

  • 2 Beds
  • 2 Baths
  • 1,674 Sq Ft

  800 Country Club Ct, Winchester, KY 40391

  Great Investment Property. This cozy Winchester duplex is in a prime location. Just minutes from the Bypass and downtown. Two bedrooms with 2 full baths. The location is close to several retail stores, restaurants, and golf courses. Property is being sold together and will not separate.

  Dale Hatton Dream Maker Realty, LLC

  800 Country Club Ct, Winchester, KY 40391
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  /16

  $240,000 Sold Apr 15, 2025

  • 1,350 Sq Ft
  • $178/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  13385 Ironworks Rd, Winchester, KY 40391

  Charming and move-in ready, this 3-bedroom, 2-bath ranch home on 1 acre offers the perfect blend of space, comfort, and convenience. The low-maintenance vinyl siding allows for easy upkeep, while the freshly painted interior creates a bright and inviting atmosphere. The large 10x20 covered rear porch provides the perfect spot to relax or entertain, with the potential to be converted into a

  Joshua Davis The Agency

  13385 Ironworks Rd, Winchester, KY 40391
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  /11

  Est $187,679 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft

  110 E Hickman St, Winchester, KY 40391

  110 E Hickman St, Winchester, KY 40391
• 

  

  /41

  $259,000

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft

  363 S Main St, Winchester, KY 40391

  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 space, there's plenty of room for a growing family to spread out and feel right at home.

  Zachary Otis HomeLand Real Estate Inc

  363 S Main St, Winchester, KY 40391
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  /24

  $179,500 Sold Apr 11, 2025

  • 1,050 Sq Ft
  • $171/SF
  • 44 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1945

  606 College St, Winchester, KY 40391

  Imagine yourself in this stunning home, where classic charm blends seamlessly with modern sophistication. This lovely, remodeled ranch home is ready for you to make your own. As you step inside, you'll be greeted by an open concept living area, complete with a beautiful fireplace and built-ins that add warmth and character. The newly renovated kitchen is a culinary dream, boasting crisp white

  Angelica Hebert Lifstyl Real Estate

  606 College St, Winchester, KY 40391
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  /21

  Est $148,322 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 931 Sq Ft

  29 Oliver St, Winchester, KY 40391

  29 Oliver St, Winchester, KY 40391
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  /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
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  /16

  $221,000 Sold Apr 10, 2025

  • 1,053 Sq Ft
  • $210/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  717 Estes Dr, Winchester, KY 40391

  Cozy 3 Bed, 2 Bath ranch in Winchester, KY. This delightful home offers a perfect blend of comfort and convenience, located just minutes from shopping and only 25 minutes from Lexington. Ideal for anyone looking to enjoy the tranquility of suburban living while being close to city amenities. Enjoy the beauty of hardwood floors throughout the main living areas and bedrooms and plenty of extra

  Rebecca Worth Redfin

  717 Estes Dr, Winchester, KY 40391
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  /12

  Est $143,598 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  25 Oliver St, Winchester, KY 40391

  25 Oliver St, Winchester, KY 40391
• 

  

  /49

  $645,000

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

  439 Lynnway Dr, Winchester, KY 40391

  Welcome to 439 Lynnway Drive, where a brand new roof was just installed April 2025. The main floor boasts a primary en-suite, office space, and laundry room, while the second floor offers additional bedrooms and a versatile bonus room. The basement offers private bed/bath, custom bar, home theater, and in-home gym. Step outside and prepare to be enchanted by an outdoor oasis. Outdoor kitchen

  Reagan Rainey Dream Maker Realty, LLC

  439 Lynnway Dr, Winchester, KY 40391

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