481

Recently Sold Winchester, KY Homes

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  • /34

    $342,000 Sold Sep 16, 2025

    • 1,305 Sq Ft
    • $262/SF
    • 37 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1950

    3560 Wades Mill Rd, Winchester, KY 40391

    Welcome to your future farmette just minutes from town and the highway! With 5 acres offering privacy, beautiful views over the front pond, fenced in spaces for your animals and sheds and shelters, you are most of the way to tiny farm upon moving in. With a cozy 3 bed 2 bath home, and nearly all systems updated, as well as a fairly recent roof replacement, you are able to focus on customizing to

    Sarah MacHarg Kentucky Land and Home

    3560 Wades Mill Rd, Winchester, KY 40391
  • /5

    $41,500 Sold Sep 15, 2025

    • Land
    • 0.36 Acre
    • $115,278 per Acre
    • 6 Days On Market

    434 Fairholme Way, Winchester, KY 40391

    Ready to build your forever home? Look no further! This lot is conveniently located in the highly sought after Fairholme Estates, which is a short golf cart ride to the Winchester Country Club and downtown Winchester.

    Justin Lee JL Realty Group, LLC

    434 Fairholme Way, Winchester, KY 40391
  • /30

    $310,900 Sold Sep 12, 2025

    • 3,042 Sq Ft
    • $102/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1960

    115 Hampton Ave, Winchester, KY 40391

    BRAND NEW ROOF AUGUST 2025. Priced to sell and FULL of potential. This Hampton Avenue home has curb appeal! Beautiful 2 story home located on a gorgeous treed lot with home set back with a long driveway. Quiet street located near the Bypass! First floor features a large great room with fireplace, formal living room with fireplace, formal dining room, kitchen (with pantry), powder room. Second

    Lauren Ball Deborah Ball Realty

    115 Hampton Ave, Winchester, KY 40391
  • /75

    $510,000 Sold Sep 12, 2025

    • 3,741 Sq Ft
    • $136/SF
    • 11 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2005

    130 Winterberry Cir, Winchester, KY 40391

    Welcome to this beautifully maintained modern home located in the highly sought-after Royal Oaks Estates, perfectly positioned on the edge of Winchester with quick access to shopping, dining, and more. From the moment you step inside, you'll be captivated by the soaring vaulted ceilings in the central great room—an impressive space filled with natural light and designed for both comfort and

    Josh Wood Freedom Realty & Property Management

    130 Winterberry Cir, Winchester, KY 40391
  • /28

    $244,000 Sold Sep 12, 2025

    • 1,944 Sq Ft
    • $126/SF
    • 17 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1935

    252 S Highland St, Winchester, KY 40391

    Beautifully updated 3-bedroom, 2-bath home in the heart of Winchester! Brand-new siding and a welcoming front porch set the tone. Inside, you'll find a light-filled living room with a decorative fireplace and cozy reading nook, plus refinished hardwood floors throughout most of the main level. The first-floor bedroom has new carpet and easy access to a fully updated full bath. The remodeled

    Austina Bruton The Howard Realty Co

    252 S Highland St, Winchester, KY 40391
  • /29

    $227,500 Sold Sep 11, 2025

    • 1,220 Sq Ft
    • $186/SF
    • 0 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1970

    301 Cabin Creek Heights, Winchester, KY 40391

    Nice, clean, and move in ready! This 3 bedroom, all one level brick ranch sits on a really nice half acre lot in a small rural neighborhood. Lots of recent upgrades, the most recent being a brand new roof on the house and garage! Fresh paint, updated fixtures, some new flooring, updated kitchen. The 700 sq ft detached garage was once used as a separate residence and is still connected to

    Jason Townsend Kentucky Residential Real Estate, LLC

    301 Cabin Creek Heights, Winchester, KY 40391
  • /40

    $210,000 Sold Sep 11, 2025

    • 1,628 Sq Ft
    • $129/SF
    • 31 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1981

    635 Lisletown Ln, Winchester, KY 40391

    Being sold 'as is' furniture stays with home. Tucked away on a private lane behind a charming stone wall, this storybook 2BR/2BA dome-style cottage is a one-of-a-kind retreat. Greeted by a peaceful koi pond, the home's unique wood siding and architectural flair set the tone for something truly special. Inside, natural light pours in through skylights and stained-glass accents, creating a warm,

    Robin Jones Keller Williams Legacy Group

    635 Lisletown Ln, Winchester, KY 40391
  • /37

    $275,000 Sold Sep 10, 2025

    • 2,247 Sq Ft
    • $122/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2000

    279 Ascot Ave, Winchester, KY 40391

    This 4-bedroom, 2.5-bath property is situated on a spacious .38-acre corner lot in the highly desirable Colby Ridge subdivision. The home features abundant natural light, hardwood floors, renovated kitchen with newer appliances and HVAC system.The main level includes a foyer leading to a versatile den or office, which overlooks the dining area and flows into the kitchen and living room, along

    Chase Pennington Team Pannell Real Estate

    279 Ascot Ave, Winchester, KY 40391
  • /39

    $213,900 Sold Sep 10, 2025

    • 1,072 Sq Ft
    • $200/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    310 Sarah Ct, Winchester, KY 40391

    Welcome to 310 Sarah Court! This charming 3-bedroom, 2-bath home is move-in ready and located in a USDA eligibility zone for 0% down financing—based on buyer qualification. Inside, you'll find fresh paint throughout, a spacious living area, and a functional layout perfect for everyday living or entertaining. Outside, enjoy a fully fenced backyard—ideal for pets, kids, or relaxing evenings at

    Brooke Otis Mullins RO&CO Real Estate

    310 Sarah Ct, Winchester, KY 40391
  • /33

    $240,000 Sold Sep 10, 2025

    • 2,472 Sq Ft
    • $97/SF
    • 18 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1969

    752 Wayland Dr, Winchester, KY 40391

    This ranch style house is located minutes from Fayette County line and minutes from the I-64 and I-75 corridors. This house features 4 bedrooms and 2 full baths on a walk-out basement. The owners remodeled several years ago with new kitchen and primary suite. The house is situated on a .53 acre lot within a quiet residential neighborhood. Looking for a house to make your home? come see this

    Craig Bridgewater Bridgewater Real Estate

    752 Wayland Dr, Winchester, KY 40391
  • /17

    $190,000 Sold Sep 10, 2025

    • 1,059 Sq Ft
    • $179/SF
    • 50 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1960

    114 Sunset Heights, Winchester, KY 40391

    Conveniently located, well maintained ranch with 3 bedrooms in established neighborhood, awaiting its new owner! With a newer roof, gutters (with guards), furnace and water heater...it helps take some maintenance worries away! Ample storage with storage closet in carport, and detached shed. Three hundred sq.ft. 3-seasons area in rear of home, which could be used year-round with the addition of a

    Susan Baldwin Rector Hayden Realtors

    114 Sunset Heights, Winchester, KY 40391
  • /36

    $472,500 Sold Sep 09, 2025

    • 2,593 Sq Ft
    • $182/SF
    • 1 Day On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2007

    208 Royal Oak Dr, Winchester, KY 40391

    Elegant brick and Stone Beauty in sought-after Royal Oak Subdivision! This stunning 4-bedroom, 2.5 bath home seamlessly blends timeless charm with modern comfort. The spacious primary suite is conveniently located on the main level, featuring a luxurious ensuite bath and soaring cathedral ceilings that create a serene retreat. Entertain in style with a grand living room, also boasting cathedral

    Megan McCoy Keller Williams Legacy Group

    208 Royal Oak Dr, Winchester, KY 40391
  • /57

    $260,000 Sold Sep 09, 2025

    • 1,633 Sq Ft
    • $159/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1945

    7934 Ironworks Rd, Winchester, KY 40391

    Strategically located, this two story home was built to allow for a nice breeze during hotter months, leading to lower electricity bills. The home remains in pristine working order, as well as detached garage and 3 stall barn with water hookup. Nearly 5 acres, the property is already set up with multiple sized paddocks for horses, cattle, goats, etc. Built with the original house, the oversized

    Greg Wood Freedom Realty & Property Management

    7934 Ironworks Rd, Winchester, KY 40391
  • /37

    $392,500 Sold Sep 08, 2025

    • 2,991 Sq Ft
    • $131/SF
    • 24 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1991

    576 Marseille Blvd, Winchester, KY 40391

    **Priced to sell and well below the attached appraisal dated 7/16/2025.** Welcome to this beautifully maintained 4-bedroom, 3-bathroom home with a walkout basement, nestled in the desirable Oak Hill subdivision. Thoughtfully designed and extensively landscaped both front and back, this home offers the perfect blend of comfort, functionality, and outdoor living. Step inside to discover spacious

    James Turek Bluegrass Sotheby's International Realty

    576 Marseille Blvd, Winchester, KY 40391
  • /38

    $258,900 Sold Sep 08, 2025

    • 1,678 Sq Ft
    • $154/SF
    • 1 Day On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2000

    313 Geronimo Ct, Winchester, KY 40391

    Welcome to 313 Geronimo Court in Winchester, KY well-maintained home nestled on a quiet cul-de-sac, offering comfortable living with a functional layout and great outdoor space. Inside, you will find water-resistant laminate wood-look flooring and tile throughout the main living areas, creating a clean and durable foundation. The kitchen includes refrigerator and stove with a cozy dining area

    Shari Frasure Keller Williams Commonwealth

    313 Geronimo Ct, Winchester, KY 40391
  • /38

    $599,500 Sold Sep 08, 2025

    • 2,204 Sq Ft
    • $272/SF
    • 72 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2025

    102 Bella Shae Way, Winchester, KY 40391

    Introducing the Stonewall plan—a stunning brick and stone ranch ideally positioned on a corner lot in Mallard Cove. This 4 bedroom, 2 full bath home with a side-entry garage offers timeless curb appeal and high-end features throughout. The thoughtfully designed layout includes a spacious living room with vaulted ceilings, arched and lighted built-ins, and a gas fireplace with a floor-to-ceiling

    Shane Underwood Keller Williams Commonwealth

    102 Bella Shae Way, Winchester, KY 40391
  • /56

    $639,000 Sold Sep 06, 2025

    • 4,021 Sq Ft
    • $159/SF
    • 37 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 1975

    4455 Colby Rd, Winchester, KY 40391

    Gorgeous Ranch Home On Basement, Situated Perfectly On Over 3.5 Lush Acres Of Level Seclusion, As Property Is Lined Beautiful, Mature Trees! Enjoy Peace & Quiet In This Newly Renovated Home, Offering 6 Bedrooms, 5 Baths, Ample Family Space, Home Office, (Fiber Optic Internet), Large Separate Laundry, Sun Room, 2 Covered Porches, Deck, Fire Pit, 2 Car Garage, Barn/ Workshop... THE LIST GOES ON!

    Melissa Brown Keller Williams Legacy Group

    4455 Colby Rd, Winchester, KY 40391
  • /32

    $263,000 Sold Sep 05, 2025

    • 1,397 Sq Ft
    • $188/SF
    • 2 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1960

    2 Chickadee Ln, Winchester, KY 40391

    Beautifully updated 1,397 sq ft ranch-style home with modern upgrades throughout! This move-in ready property features a new roof, HVAC, water heater, gutters, and fresh landscaping. The exterior has been freshly painted, including the back deck, and the driveway and sidewalk have been pressure washed. Inside, you'll find all-new flooring and fresh paint throughout. The kitchen features updated

    Ashley Spencer Keller Williams Commonwealth

    2 Chickadee Ln, Winchester, KY 40391
  • /55

    $174,900 Sold Sep 05, 2025

    • 1,222 Sq Ft
    • $143/SF
    • 26 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1988

    20 Heather Ln, Winchester, KY 40391

    This charming 2-bedroom, 1.5-bath brick townhome offers a comfortable living space in a prime location. Inside, you'll find all-new LVP flooring, fresh carpet, and a fresh coat of paint throughout. The spacious living room flows into a well-sized kitchen featuring brand-new countertops and ample counter space—perfect for everyday cooking and entertaining.Appliances including the washer,

    Josh Wood Freedom Realty & Property Management

    20 Heather Ln, Winchester, KY 40391
  • /64

    $929,000 Sold Sep 05, 2025

    • 2,670 Sq Ft
    • $348/SF
    • 23 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2025

    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
  • /16

    $201,000 Sold Sep 05, 2025

    • 1,526 Sq Ft
    • $132/SF
    • 66 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1930

    128 Alabama St, Winchester, KY 40391

    Charm meets convenience in this delightful newly renovated home! Experience city living at its finest with the tranquility of your own spacious backyard, yet be within walking distance to shops and restaurants! Step inside the living room and let the natural light peeking through the large windows welcome you home. With a bedroom on the main floor, two bedrooms upstairs, and a bonus room that

    Paul Eads Woods Realty Group

    128 Alabama St, Winchester, KY 40391
  • /31

    $485,000 Sold Sep 05, 2025

    • 3,262 Sq Ft
    • $149/SF
    • 11 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1906

    10 French Ave, Winchester, KY 40391

    Remember when things were built to last? This home was built in 1906 and recently underwent a complete renovation to bring this 118 year old home into the 21st century. The owners maintained all of the architectural details while adding the modern luxuries of today. Improvements made to the home consist of new dimensional shingle roof, gutters, soffits rebuilt including rebuilding the decorative

    Brian England Keller Williams Bluegrass Realty

    10 French Ave, Winchester, KY 40391
  • /27

    $210,000 Sold Sep 04, 2025

    • 1,150 Sq Ft
    • $183/SF
    • 1 Day On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    305 Geronimo Ct, Winchester, KY 40391

    Welcome home to this beautifully appointed 3-bedroom, 2-bathroom residence designed for style and comfort. Step inside to a bright, open-concept living space featuring brand-new stainless steel appliances, complemented by luxurious granite and marble backsplash in the gourmet kitchen—perfect for culinary enthusiasts. Entertain or unwind on the expansive front and back decks, ideal for morning

    Aaron Kendall Lifstyl Real Estate

    305 Geronimo Ct, Winchester, KY 40391
  • /51

    $428,000 Sold Sep 04, 2025

    • 3,181 Sq Ft
    • $135/SF
    • 34 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1960

    17 Hampton Ave, Winchester, KY 40391

    This meticulous house is located within walking distance of many popular Winchester destinations; The Winchester Country Club, The Public Library and the indoor gym and swimming facility at College Park. Now back to the meticulous house. When you enter the front door you will immediately feel the how the owners have taken such great care of this house. The gleaming hardwoods, the large living

    Craig Bridgewater Bridgewater Real Estate

    17 Hampton Ave, Winchester, KY 40391
  • /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
  • /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
  • /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
  • /15

    $110,000 Sold Sep 04, 2025

    • 924 Sq Ft
    • $119/SF
    • 3 Beds
    • 2 Baths
    • Built 2024

    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
  • /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
  • /33

    $180,000 Sold Sep 02, 2025

    • 1,000 Sq Ft
    • $180/SF
    • 22 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1977

    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 Mullins RO&CO Real Estate

    307 Blair Ave, Winchester, KY 40391
  • /41

    $259,900 Sold Aug 31, 2025

    • 1,544 Sq Ft
    • $168/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2006

    315 Newcastle Ln, Winchester, KY 40391

    Nestled in a cul-de-sac in Winchester's Oakmont neighborhood, this 3-bedroom, 2.5-bath home offers comfort and convenience. The main level features vinyl plank flooring throughout, a spacious living room, and an eat-in kitchen, plus a laundry area and half bath. Upstairs, you'll find three generously sized bedrooms, including a primary suite with a walk-in closet and private bath. A second full

    Terra Long Keller Williams Commonwealth

    315 Newcastle Ln, Winchester, KY 40391
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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

Showing Results 1 - 40, Page 1 of 13

Frequently Asked Questions

What is the average home price in Winchester, KY?
Homes for sale in Winchester, KY have an average home price of $330,992.
What is the average time to sell a house in Winchester, KY?
The houses for sale in Winchester, KY spend an average of 30 days on the market.
What is the number of active homes for sale in Winchester, KY?
There are 91 active homes for sale in Winchester, KY.
How many homes have sold over the last 12 months in Winchester, KY?
323 homes have sold in Winchester, KY over the last 12 months.

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$240,000
Median Single Family Sale Price
$259,900
Median Townhouse Sale Price
$195,200
Average Price Per Sq Ft
$160
Number of Homes for Sale
91
Last 12 months Home Sales
323
Months of Supply
3.40
Median List Price
$260,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
0%
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