Recently Sold Winchester, KY Homes

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  /33

  $385,000 Sold Sep 04, 2025

  • 2,741 Sq Ft
  • $140/SF
  • 12 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1985

  113 Shala Mar Rue, Winchester, KY 40391

  Beautifully maintained brick ranch on a full basement, offering over 4,000 square feet under roof in a highly desirable location just minutes from Hamburg, I-64, Lexington, and Clark County Regional Hospital. This spacious home features 4 bedrooms, 3 full baths, and stunning hardwood floors. Two impressive floor-to-ceiling fireplaces add charm on both levels. The kitchen includes new stainless

  Rebakah Goodpaster Keller Williams Legacy Group

  113 Shala Mar Rue, Winchester, KY 40391
• 

  Explore Winchester

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  /22

  $201,000 Sold Sep 04, 2025

  • 1,235 Sq Ft
  • $163/SF
  • 26 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1980

  110 Colonial Park Dr, Winchester, KY 40391

  Relax in your private paradise! The fully privacy fenced backyard hides the pool and deck area along with the really cool hot tub room, huge dog kennel, and storage shed. 3 bedrooms, all one level, newer roof and HVAC system. Come see what sets this home apart from all the rest!

  Jason Townsend Kentucky Residential Real Estate, LLC

  110 Colonial Park Dr, Winchester, KY 40391
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  /48

  $550,000 Sold Sep 04, 2025

  • 3,489 Sq Ft
  • $158/SF
  • 43 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2007

  594 Earlymeade Dr, Winchester, KY 40391

  This stunning 5BR,3BA brick home blends classic charm with modern comfort, all situated in a highly desirable neighborhood. The exterior features clean lime wash brick with contrasting painted trim and a crisp new black roof, new black 6mm gutters, exuding timeless curb appeal. A wide front porch with elegant columns welcomes you into the home, perfect for relaxing or greeting guest.Inside you

  Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391
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  /28

  $370,000 Sold Sep 03, 2025

  • 3,078 Sq Ft
  • $120/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  220 Spring Valley Dr, Winchester, KY 40391

  This beautiful 5 acre property is a rare find! Located on a quiet cul-de-sac just minutes from I-64, Winchester and Bourbon County, this home offers the perfect blend of tranquility and convenience. The home includes 4 bedrooms, 2.5 baths with a mostly finished basement providing additional living space and storage. There are 2 wood burning fireplaces, perfect for cozy evenings. Additionally,

  Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
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  /10

  $325,000 Sold Aug 29, 2025

  • 1,584 Sq Ft
  • $205/SF

  • 3 Beds
  • 2 Baths
  • Built 1999

  210 Cabin Creek Rd, Winchester, KY 40391

  3 Bedroom 2 Bath brick ranch home on almost 2 acres.

  Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
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  /25

  $375,000 Sold Aug 29, 2025

  • 3,111 Sq Ft
  • $121/SF
  • 8 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2001

  317 Hanover Dr, Winchester, KY 40391

  Looking for room to grow? Welcome to 317 Hanover Drive, a spacious and inviting home located in the popular Colby Ridge neighborhood—just minutes from all the shopping, dining, and conveniences Winchester has to offer. This beautiful 5-bedroom, 3.5-bath home offers a finished walkout basement and thoughtful touches throughout. Enjoy relaxing evenings on the charming front porch or entertain on

  Mike Wheatley Bluegrass Properties Group

  317 Hanover Dr, Winchester, KY 40391
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  /41

  $249,900 Sold Aug 29, 2025

  • 2,146 Sq Ft
  • $116/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  407 Walnut St, Winchester, KY 40391

  Welcome to this beautifully remodeled brick ranch sitting on a massive 1.2-acre corner lot in the heart of Winchester! This home blends modern updates with timeless charm and offers 3 spacious bedrooms, 2 full bathrooms, and a versatile bonus room that could easily serve as a fourth bedroom, home office, or playroom. Step inside to find fresh paint, brand new flooring throughout, all-new windows,

  Jason Crask THRIVE Realty

  407 Walnut St, Winchester, KY 40391
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  /40

  $331,000 Sold Aug 29, 2025

  • 1,988 Sq Ft
  • $166/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  13544 Irvine Rd, Winchester, KY 40391

  Experience Stunning Sunrises and Starry Nights!Nestled on nearly 4 peaceful acres, this charming brick ranch offers the tranquility of country living with modern comfort. Surrounded by a beautiful tree grove, the home features a full walk-out basement with exciting potential—finish the lower level and additional bathroom to expand your living space!Inside, you'll find 3 spacious

  Susan Baldwin Rector Hayden Realtors

  13544 Irvine Rd, Winchester, KY 40391
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  /23

  $335,000 Sold Aug 27, 2025

  • 2,936 Sq Ft
  • $114/SF
  • 8 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1986

  413 Lyon Dr, Winchester, KY 40391

  Well maintained in an established neighborhood on a large corner lot. Nice hardwood floors in the dining area. Dental crown molding and chair rail in the living room and kitchen/dining area. Book shelves and wood stove in the den. Room in the basement could be an additional bedroom. Large basement garage with cabinets. Front brick porch, rear 10'x16' all season room, rear court yard and deck

  Ray Rush Rush Real Estate

  413 Lyon Dr, Winchester, KY 40391
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  /27

  $270,000 Sold Aug 25, 2025

  • 1,813 Sq Ft
  • $149/SF
  • 13 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2005

  9 Hillcrest Dr, Winchester, KY 40391

  Built To Last, This Extra Solid Ranch Home, Was Built With Top Of The Line Materials! Turn It Into Your Dream Home Or Use As A Great Investment Property, Where As, You Can Easily Double Your Square Footage When Finishing The Basement. A Beautiful Layout, Offering 3 Bedrooms, 2 Full Baths, Chef's Kitchen, Separate Laundry, Off The Attached Garage, Open Concept Living & Dining Space, On The Main.

  Melissa Brown Keller Williams Legacy Group

  9 Hillcrest Dr, Winchester, KY 40391
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  /52

  $500,000 Sold Aug 25, 2025

  • 2,020 Sq Ft
  • $248/SF
  • 103 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2015

  1778 Elkin Rd, Winchester, KY 40391

  Peaceful Living on 8.83 acres of gently rolling hills in the heart of Kentucky. Breathtaking countryside features a newer custom-built home that offers peace, privacy and serene surroundings. Wake up to birdsong, watch deer wander at dusk and soak in the golden sunsets from your own front porch. Highlights include: spacious open concept kitchen with white custom cabinetry, beautiful engineered

  Vicki VanWinkle Pacesetters Real Estate

  1778 Elkin Rd, Winchester, KY 40391
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  /19

  $281,000 Sold Aug 22, 2025

  • 1,708 Sq Ft
  • $165/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1999

  223 Cross Brook Ln, Winchester, KY 40391

  Nice 3 bedroom 2 1/2 bath in one of the most desirable neighborhoods in Winchester, Colby Ridge. Brand new hvac units, large yard, and convenient to almost everything in Winchester

  Dwight Donaldson Murphy Realty Group

  223 Cross Brook Ln, Winchester, KY 40391
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  /45

  $269,000 Sold Aug 22, 2025

  • 2,136 Sq Ft
  • $126/SF
  • 2 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  402 Mcdowell Dr, Winchester, KY 40391

  Very clean, well kept home! Split foyer with plenty of space including a large kitchen with peninsula and open to dining area. Four bedrooms, 2.5 baths. Nice size living room on main level with additional family room with wood burning fireplace featuring full brick wall on lower level.Very large 2 car garage. Beautiful back covered deck that leads to a lovely gazebo in the spacious fenced in

  Christine McDonald FC Tucker Bluegrass

  402 Mcdowell Dr, Winchester, KY 40391
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  /34

  $269,500 Sold Aug 22, 2025

  • 2,456 Sq Ft
  • $110/SF
  • 11 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2022

  148 Gibson Way, Winchester, KY 40391

  NEW PRICE!Better Than New Construction!!! This Spacious 4 Bedroom 2 1/2 Bath Home Is Move In Ready And Has A Beautiful Farm View From Your Covered Porch. Features Include A Large Open Living Room And Kitchen With Plenty Of Cabinet Space; Large Island With Faucet; Granite Countertops; Tile Backsplash; Stainless Steel Appliances; Large pantry; Gas Log Fireplace; Gas Heat; Gas Water Heater;

  W Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
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  /3

  $94,000 Sold Aug 22, 2025

  • Land
  • 4.02 Acres
  • $23,383 per Acre

  • 140 Days On Market

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  Prime building lot - 4 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). 2010 and 2058 approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

  Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
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  /24

  $277,500 Sold Aug 21, 2025

  • 1,588 Sq Ft
  • $175/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  10 Howard Dr, Winchester, KY 40391

  Charming All-Brick Ranch with Bonus Space & Huge Yard!This beautifully updated 3-bedroom, 2-bathroom all-brick ranch offers timeless charm and modern touches throughout. Situated on a generous, fully fenced lot with mature trees, this home features fresh neutral paint, stylish shiplap accents, and abundant natural light. The spacious detached bonus room is perfect for a home office, gym,

  Holly Goeing The Agency

  10 Howard Dr, Winchester, KY 40391
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  /23

  $225,000 Sold Aug 21, 2025

  • 1,080 Sq Ft
  • $208/SF
  • 12 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1972

  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
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  /33

  $335,000 Sold Aug 20, 2025

  • 1,527 Sq Ft
  • $219/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1946

  543 S Maple St, Winchester, KY 40391

  Nestled on the charming street of South Maple this beautiful ranch home offers the perfect blend of comfort and convenience. Featuring three bedrooms and two modern bathrooms, this single-level living space is designed for ease and elegance. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating a welcoming atmosphere for gatherings. Large windows fill

  Lucy Martin Jenkins United Real Estate Bluegrass

  543 S Maple St, Winchester, KY 40391
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  /25

  $287,000 Sold Aug 20, 2025

  • 1,402 Sq Ft
  • $205/SF
  • 36 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  220 Mcdowell Dr, Winchester, KY 40391

  This beautiful 3BR, 2BA ranch style home offers a blend of comfort and style. Featuring an inviting open concept layout, the spacious living area flows effortlessly into the kitchen and dining spaces- perfect for family gatherings or entertaining guests. The exterior boasts charming curb appeal with a well maintained lawn, new siding, stone accents, and a cozy covered front porch. A 2 car

  Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
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  /20

  $205,000 Sold Aug 19, 2025

  • 1,113 Sq Ft
  • $184/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  202 Custer Ct, Winchester, KY 40391

  Welcome to this inviting 3-bedroom, 2-bath home. Whether you're looking for a starter home to make your own or a smart investment property, this one checks all the boxes. Living area filled with natural lighting leading into the kitchen. The primary suite features its own private bath and walk in closet. While two additional bedrooms share a full hall bathroom. Outside, enjoy a generous

  Brittany Beer EXP Realty, LLC

  202 Custer Ct, Winchester, KY 40391
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  /32

  $200,000 Sold Aug 19, 2025

  • 1,164 Sq Ft
  • $172/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1945

  116 Linden Ave, Winchester, KY 40391

  Welcome to 116 Linden Avenue located minutes from Winchester's charming downtown. This move in ready 3-bedroom, 2-bath home is complete with fresh paint and a great layout that offers both comfort and functionality. Enjoy the convenience of a first-floor primary bedroom and the bonus of a spacious yard, perfect for outdoor entertaining, gardening, or relaxing. Whether you're looking for your next

  Robert Bratton Bluegrass Sotheby's International Realty

  116 Linden Ave, Winchester, KY 40391
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  /22

  $600,000 Sold Aug 19, 2025

  • Land
  • 12 Acres
  • $48,465 per Acre

  • 125 Days On Market

  1203 Irvine Rd, Winchester, KY 40391

  This 12+ acre piece of prime real estate is full of potential! Zoned for business uses, the location is conveniently located with easy access to Veterans Memorial Bypass, I-64, and downtown Winchester. Utilities are already available at this property and there is a small structure included in as-is condition. Give us a call with any further questions.

  Josh Wood Freedom Realty & Property Management

  1203 Irvine Rd, Winchester, KY 40391
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  /81

  $599,500 Sold Aug 18, 2025

  • 2,222 Sq Ft
  • $270/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  2615 Crowe Ridge Rd, Winchester, KY 40391

  This one-owner, custom-built home sits on approximately 8 acres of beautiful Bluegrass land and offers space, comfort, and thoughtful design throughout. The open-concept great room and kitchen feature exposed beam ceilings and custom-stained concrete floors. The kitchen is a dream for cooks,with abundant counter space, storage, a large island, and window overlooking the backyard and pool. Just

  ROBIN TRIMBLE HomeFirst Real Estate

  2615 Crowe Ridge Rd, Winchester, KY 40391
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  /73

  $799,000 Sold Aug 18, 2025

  • 3,664 Sq Ft
  • $218/SF
  • 64 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1989

  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 & stainless steel appliances. Entertain in your custom dining room featuring a tray ceiling & wainscoting, or on your covered outdoor Trex deck. Relax in either your living

  Libby VanMeter Marshall Lane Real Estate - Lexington

  1183 the Ridings Rd, Winchester, KY 40391
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  /21

  $173,000 Sold Aug 15, 2025

  • 964 Sq Ft
  • $179/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  222 Buffalo Trace, Winchester, KY 40391

  Welcome home to this darling home located in the Buffalo Trace Subdivision. This home is one floor living and features 3 bedrooms and 2 baths and is freshened up and ready for a new owner! All electric, off-street parking.

  Elizabeth Herrington Bluegrass Sotheby's International Realty

  222 Buffalo Trace, Winchester, KY 40391
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  /22

  $217,000 Sold Aug 15, 2025

  • 1,400 Sq Ft
  • $155/SF
  • 14 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2001

  517 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 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

  517 Acadia Way, Winchester, KY 40391
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  /77

  $2,075,000 Sold Aug 15, 2025

  • Land
  • 71 Acres
  • $29,221 per Acre

  • 14 Days On Market

  27 Sundown Ln, Winchester, KY 40391

  Tucked just 10 minutes from Hamburg on the Fayette/Clark County line, this 71+acre estate on Sundown Lane truly lives up to its name—offering breathtaking sunset views, along with peaceful luxury in a scenic country setting. At the end of a gated driveway, a stately colonial-style home combines refined living with countryside charm. Highlights include hardwood floors, two stone fireplaces, dual

  Abby Jones Bluegrass Sotheby's International Realty

  27 Sundown Ln, Winchester, KY 40391
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  /65

  $275,000 Sold Aug 15, 2025

  • 1,873 Sq Ft
  • $147/SF
  • 130 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1960

  151 Hilltop Dr, Winchester, KY 40391

  Lovely ranch on a basement home in a small rural neighborhood. This location is the perfect blend of rural living but very convenient to everything! Less than 1 mile from the eastern bypass that provides fast access to I-64, downtown Winchester, parks, and shopping. Large half acre lot with fenced in backyard and a chicken coop! Large deck on the back for entertaining or just relaxing while

  Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
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  /32

  $360,000 Sold Aug 14, 2025

  • 2,746 Sq Ft
  • $131/SF
  • 12 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1990

  418 Skylark Dr, Winchester, KY 40391

  There's a certain kind of comfort you feel the moment you pull up, a classic brick home, shaded by mature trees, in a quiet neighborhood where kids still ride bikes and neighbors wave from their driveways. Inside, the layout just works. The kitchen has the kind of space that makes everyday life easier, granite counters, shaker cabinets, and an island that's seen everything from cereal mornings to

  Kymberly McCreary EXP Realty, LLC

  418 Skylark Dr, Winchester, KY 40391
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  /54

  $269,900 Sold Aug 12, 2025

  • 1,536 Sq Ft
  • $176/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  137 Sturbridge Ln, Winchester, KY 40391

  This lovely story and a half home is conveniently located close to Bypass road with easy access to everything Winchester has to offer. The main floor offers a comfortable living area that connects to the spacious eat-in kitchen, a convenient half bathroom, and the laundry room. Take a step out the back patio door to experience the generous, shaded, privacy fenced back yard perfect for kids or

  Josh Wood Freedom Realty & Property Management

  137 Sturbridge Ln, Winchester, KY 40391
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  /41

  $279,900 Sold Aug 12, 2025

  • 1,808 Sq Ft
  • $155/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  225 Prescott Ln, Winchester, KY 40391

  What are your thoughts on a residence featuring a prime location, within walking distance to several schools? Now that I've got your interest, the primary bedroom is situated on the main level. How do three or possibly four bedrooms, accompanied by 2.5 bathrooms, sound? This residence is located in the Oakmont subdivision and has been under the same ownership for over 15 years. Don't miss your

  Teresa Richmond Freedom Realty & Property Management

  225 Prescott Ln, Winchester, KY 40391
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  /29

  $180,000 Sold Aug 11, 2025

  • 1,025 Sq Ft
  • $176/SF
  • 0 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1970

  217 Blair Ave, Winchester, KY 40391

  Welcome to 217 Blair Avenue in the heart of Winchester—a charming and move-in-ready home offering comfort, character, and convenience. This property features 3 spacious bedrooms, 1 full bath, and an inviting layout featuring hardwood floors, a light-filled living room, and an updated kitchen with ample cabinet space. Outside, enjoy a large backyard ideal for gatherings, gardening, or relaxing

  Ashley Barreto Indigo & Co

  217 Blair Ave, Winchester, KY 40391
• 

  

  /50

  $465,000 Sold Aug 11, 2025

  • 2,784 Sq Ft
  • $167/SF
  • 2 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2008

  701 Lisletown Ln, Winchester, KY 40391

  Perfectly nestled at the end of shared private lane, this mid-century modern home w/full finished walkout basement offers luxury, privacy & natural beauty. Designed by architect R.L. Isenhour, this distinctive property is situated on just over 3 wooded acres, surrounded by forest & overlooking the Kentucky River. Step inside to soaring ceilings, expansive windows & a striking floor-to-ceiling

  Robin Jones Keller Williams Legacy Group

  701 Lisletown Ln, Winchester, KY 40391
• 

  

  /75

  $289,900 Sold Aug 11, 2025

  • 1,429 Sq Ft
  • $203/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  126 Ashley Dr, Winchester, KY 40391

  Don't miss out on this Beautiful RANCH Style home w/Private, new and Fully Fenced Yard. This Move-in Ready 3 Bed / 2 Bath is immaculate with many updates. Completely remodeled Bathroom with walk-in shower, Fresh Paint, Spacious living room w/ Vaulted Ceiling. Carpet all replaced with gorgeous, matching hardwood thru out. Granite Countertops, new can lighting and kitchen floor replaced with

  Jennifer Guyton White Realty, LLC

  126 Ashley Dr, Winchester, KY 40391
• 

  

  /39

  $450,000 Sold Aug 08, 2025

  • 2,076 Sq Ft
  • $217/SF
  • 32 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  600 Ferry Rd, Winchester, KY 40391

  Experience abundant wildlife with turkey and deer in your own hunting retreat, or simply enjoy the views from your backyard on this stunning 33-acre property. Conveniently located near the Kentucky River, with a boat ramp nearby, this home offers the perfect blend of nature and accessibility, making it ideal for nature lovers or those who enjoy fishing and hunting.Step inside to the foyer,

  Cathleen Gedeon CENTURY 21 Advantage Realty

  600 Ferry Rd, Winchester, KY 40391
• 

  

  /39

  $240,000 Sold Aug 08, 2025

  • 1,235 Sq Ft
  • $194/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  172 Ryans Mill Rd, Winchester, KY 40391

  This nicely maintained 3-bedroom, 2-bath ranch offers the perfect blend of comfort and convenience. Enjoy abundant natural light throughout the open floor plan, creating a bright and inviting atmosphere. The spacious kitchen and living areas are perfect for both daily living and entertaining. Step outside to a generous, fully fenced backyard, ideal for pets, play, or outdoor gatherings. Located

  Elizabeth Herrington Bluegrass Sotheby's International Realty

  172 Ryans Mill Rd, Winchester, KY 40391
• 

  

  /31

  $88,500 Sold Aug 08, 2025

  • 1,144 Sq Ft
  • $77/SF
  • 28 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1945

  15 Sycamore St, Winchester, KY 40391

  3 bedroom 1 bath house. Older home that needs some updates. This house is being sold online at www.goochsells.com. Selling as/is, must close within 30 days from close of auction. 10% Buyers Premium, 10% down night of sell. Rony Jo Ballou Auctioneer 859-595-6808

  Rony Jo Ballou Power House Realty

  15 Sycamore St, Winchester, KY 40391
• 

  

  /32

  $349,900 Sold Aug 01, 2025

  • 2,111 Sq Ft
  • $166/SF
  • 2 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  275 Cross Brook Ct, Winchester, KY 40391

  Tucked away on a quiet corner cul-de-sac, this 3-bedroom, 2.5-bath home offers space, style, and versatility. Inside, you'll find updated flooring, large bedrooms, and an open layout perfect for everyday living and entertaining. The oversized walk-in pantry and 2-car garage add function and storage, while the huge additional building out back sets this property apart—ideal for a workshop, home

  Amanda Stewart Selling the South Realty

  275 Cross Brook Ct, Winchester, KY 40391
• 

  

  /53

  $867,500 Sold Aug 01, 2025

  • 4,698 Sq Ft
  • $185/SF
  • 318 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1885

  511 Boone Ave, Winchester, KY 40391

  One of a kind opportunity to live in history and in luxury in one of Winchester's finest offerings. This majestic home spares no detail, offering charming details throughout like hardwood floors, high ceilings, large windows, crown moldings, and fireplaces throughout. As well, the gracious lot offers expansive views and privacy with its large patio seating area and beautiful swimming pool. Ripe

  Greg Leveridge Block + Lot Real Estate

  511 Boone Ave, Winchester, KY 40391
• 

  

  /43

  $129,900 Sold Jul 31, 2025

  • 858 Sq Ft
  • $151/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1959

  44 Watts Rd, Winchester, KY 40391

  Tucked away on a peaceful dead-end street with minimal traffic, this inviting 2-bedroom, 1-bath home offers comfort, convenience, and character. Step inside to find beautiful hardwood floors throughout, a spacious living room full of natural light, and a cozy eat-in kitchen perfect for casual meals and morning coffee.Enjoy the privacy of a fenced backyard—ideal for relaxing, gardening, or

  Josh Wood Freedom Realty & Property Management

  44 Watts Rd, Winchester, KY 40391

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