Winchester, KY Homes

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  /67

  $699,000

  • 3 Beds
  • 4 Baths
  • 4,123 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Just 12 minutes from Lexington, this charming home rests atop 5 acres of breathtaking rolling hills, offering a perfect mix of privacy, elegance, and convenience. The long private driveway may seem steep at first glance, but after a few trips, you'll find it feels completely natural, and the elevated vantage point rewards you with sweeping countryside views and unmatched tranquility, exactly the

  

  Oxana Lopetegui-Pineda

  Lifstyl Real Estate

  (859) 659-6462

  1775 Irvine Rd, Winchester, KY 40391
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  Explore Winchester

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  /32

  $800 - $1,300 per month

  Summit Apartments

  1 - 3 Beds

  260 Oxford Dr, Winchester, KY 40391

  The Summit located in Winchester; KY is just minutes away from major employers. We are just a short drive from Lexington, KY. Come see our pet friendly community with lots of green space. We have spacious one-, two-, and three-bedroom apartment homes with caring on-site management. Our homes feature walk-in closets, new Laminate Vinyl Plank Flooring, fully equipped kitchens, washer/dryer

  260 Oxford Dr, Winchester, KY 40391
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  /19

  $219,000 Sold Sep 17, 2025

  • 1,335 Sq Ft
  • $164/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  521 Hidden Hills Way, Winchester, KY 40391

  Charming 3-Bedroom Home with Modern Upgrades & Outdoor Living!Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that offers both comfort and functionality. Step inside to discover a spacious open-concept living and dining area, perfect for entertaining or relaxing with family. The generous kitchen features ample counter space, a walk-in pantry, and plenty of room for the

  Cathy Cornett-Wilson Rector Hayden Realtors

  521 Hidden Hills Way, Winchester, KY 40391
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  /30

  Est $74,154 Not Listed For Sale

  690 Lisletown Ln, Winchester, KY 40391

  690 Lisletown Ln, Winchester, KY 40391
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  /71

  $799,999

  • 4 Beds
  • 2.5 Baths
  • 5,290 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Step into a world of both comfort and convenience with this beautiful 3/4 bedroom, two and one half bath, perfectly designed for relaxation and entertainment. Key features of this property include outdoor spaces to enjoy morning coffee or quiet evening chats. The cozy back porch extends your living space, ideal for dining and enjoying the tranquil surroundings, The beautifully designed patio

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 813-4308

  186 Chardonnay Ct, Winchester, KY 40391
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  /8

  $675 per month

  • Studio
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  192 Wabash Ave, Winchester, KY 40391

  This property at 192 Wabash Ave features a studio layout with 0 bedrooms and 1 bathroom, encompassing a total of 600 square feet. The living area is designed for efficiency, providing ample space for both relaxation and functionality. The property includes smoke-free living and access to on-site laundry facilities for added convenience. This unit is ideal for individuals seeking a compact

  192 Wabash Ave, Winchester, KY 40391
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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
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  /49

  Est $384,183 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,095 Sq Ft

  21 Colby Hills Dr, Winchester, KY 40391

  21 Colby Hills Dr, Winchester, KY 40391
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  /14

  $312,975

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft

  1363 Clintonville Rd, Winchester, KY 40391

  Here's your chance to own a rare 5-acre property in Clark County, one of Central Kentucky's most desirable areas. Tucked just minutes from downtown Winchester, the Hamburg corridor, and Lexington, this property blends convenience with the peacefulness of country living. Whether you're dreaming of building a brand-new home, expanding into a mini farm, or investing in future growth, this land gives

  

  Rebakah Goodpaster

  Keller Williams Legacy Group

  (859) 659-6863

  1363 Clintonville Rd, Winchester, KY 40391
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  /18

  $1,000 - $1,050 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  127 W Hickman St, Winchester, KY 40391

  Please read all details before contacting:1. Unit has 4 rooms: 1 Bedroom with 1 walk-in closet, Living Room, Kitchen & Dining Room in one with pantry, 1 Bathroom.2. Apartment is on the second floor, but it is not wheelchair accessible3. Parking space available in rear parking lot and/or front street parking.4. Tenant pays for electric, gas (optional for extra heat),

  127 W Hickman St, Winchester, KY 40391
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  /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
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  /51

  Est $508,593 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,654 Sq Ft

  2051 Kiddville Rd, Winchester, KY 40391

  2051 Kiddville Rd, Winchester, KY 40391
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  /40

  $355,000

  • 3 Beds
  • 3 Baths
  • 2,166 Sq Ft

  115 Woodford Dr, Winchester, KY 40391

  Discover a perfect blend of comfort and elegance as you step inside this charming home. Sitting on a generous 1/4 acre lot, this property offers a peaceful retreat with space to relax and entertain both inside and out. The heart of the home is the airy and open kitchen, featuring an oversized island that is perfect for gathering and sharing a meal. A dedicated keeping room provides a cozy

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 251-8500

  115 Woodford Dr, Winchester, KY 40391
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  /18

  $1,000 - $1,050 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  127 W Hickman St, Winchester, KY 40391

  Please read all details before contacting:1. Unit has 4 rooms: 1 Bedroom with 1 walk-in closet, Living Room, Kitchen & Dining Room in one with pantry, 1 Bathroom.2. Apartment is on the second floor, but it is not wheelchair accessible3. Parking space available in rear parking lot and/or front street parking.4. Tenant pays for electric, gas (optional for extra heat),

  127 W Hickman St, Winchester, KY 40391
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  /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
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  /44

  Est $497,880 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,056 Sq Ft

  1927 Kiddville Rd, Winchester, KY 40391

  1927 Kiddville Rd, Winchester, KY 40391
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  /48

  $398,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,087 Sq Ft

  213 Honeysuckle Ln, Winchester, KY 40391

  Welcome to one of Winchester's most established neighborhoods. This charming 2 story offers 4 bedrooms, 2 full baths, and 2 half baths, one in the finished basement. The layout features cozy nooks throughout the second story and a recently added bedroom over the garage with its own mini split hvac, perfect for guests, a home office, or creative space. The finished basement provides room for

  Shari Frasure Keller Williams Commonwealth

  213 Honeysuckle Ln, Winchester, KY 40391
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  /25

  $814 per month

  Studio 28 Apartments

  Studio

  27 E Washington St, Winchester, KY 40391

  *One Month Free Rent!* All Utilities Included! Nice Studio Apt Near Downtown Winchester!Marketing DescriptionStudio Apartment Available at Studio 29 Apartments, Winchester, KY! One Bath; Only 5 Minutes from Downtown! Off-Street Parking, Small Pets Ok; All Utilities Included! Kitchen includes a Stove, Refrigerator, and Microwave; Non-smoking.Conveniently located near Shopping, Grocery

  27 E Washington St, Winchester, KY 40391
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  /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
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  /112

  Est $723,332 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,311 Sq Ft

  703 Kiddville Rd, Winchester, KY 40391

  703 Kiddville Rd, Winchester, KY 40391
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  /29

  $427,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,361 Sq Ft

  4732 Old Boonesboro Rd, Winchester, KY 40391

  NEW PRICE REDUCTION!!! This Is The One You Have Been Waiting For!!! This Completely Remodeled 4 Bedroom 3 Bathroom Home On An Unfinished Basement Has It All. Features Include An Open Floor Plan; Dining Room With Fireplace; Big Kitchen With Lots Of Cabinets; Granite Tops; Stainless Steel Appliances; Range Hood; Farmhouse Sink; Huge Laundry Room Off Kitchen/Master Bedroom; First Floor Master

  W Patrick Arvin Keller Williams Commonwealth

  4732 Old Boonesboro Rd, Winchester, KY 40391
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  /25

  $1,299 - $1,499 per month

  SPECIALS: The Reserve & Enclave at Fairholme

  2 - 3 Beds

  100-145 Sam Winston Way, Winchester, KY 40391

  Beautiful Townhomes with 2 Bedrooms and 2.5 Baths, located within both The Enclave at Fairholme & The Reserve at Fairholme Townhome Communities. Built between 2019-2022. Fully equipped kitchens feature Stainless Steel Appliances, and includes Stove, Refrigerator, Dishwasher, and Microwave. Washer and Dryer Included! Hardwood LVT Flooring throughout.Off-Street Parking. Select Units Have a

  100-145 Sam Winston Way, Winchester, KY 40391
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  /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
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  /43

  Est $403,735 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,826 Sq Ft

  700 Vienna Rd, Winchester, KY 40391

  700 Vienna Rd, Winchester, KY 40391
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  /117

  $3,175,000

  • 8 Beds
  • 7.5 Baths
  • 12,702 Sq Ft

  4664 Lexington Rd, Winchester, KY 40391

  Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot

  Zach Davis Kirkpatrick & Company

  4664 Lexington Rd, Winchester, KY 40391
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  /10

  $1,450 - $1,800 per month

  7 North Main

  1 - 2 Beds

  7 N Main St, Winchester, KY 40391

  Brand New Apartments in the Heart of Downtown WinchesterMultiple Layouts AvailableHighlights:-Quartz Countertops, New Cabinets, and New Appliances (Dishwasher, Fridge, Range)-New LVP Floors-Off-Street Parking Lot for Tenants and Guests-Prime Downtown Location on Main St-Close to Interstate to Lexington-In the Heart of Downtown Winchester

  7 N Main St, Winchester, KY 40391
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  /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
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  /96

  Est $448,803 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,700 Sq Ft

  2430 Log Lick Rd, Winchester, KY 40391

  2430 Log Lick Rd, Winchester, KY 40391
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  /23

  $498,900

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare find! Gorgeous 25 acres of gently rolling land with a barn and creek is perfect for building your dream home and creating your homestead! Don't miss this opportunity! This is farm is conveniently located 20 miles from Hamburg and 5 miles from the Winchester bypass. No city sewage. Deed restrictions apply. Relax and enjoy the spectacular views. Get ready to enjoy life! Land consists of 2

  Lura Justice Rector Hayden Realtors

  2996/3056 Irvine Rd, Winchester, KY 40391
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  /12

  $1,300 per month

  • 3 Beds
  • 2 Baths
  • 1,133 Sq Ft
  • Townhouse for Rent

  401 Cricket Ln Unit 403 Cricket, Winchester, KY 40391

  Spacious 3BR/2BA home, all on 1 level with attached vaulted ceilings, garage, and patio. Hardwood laminate floors and a Stainless Steel kitchen. Washer/Dryer hook ups. Near Wal-Mart just off Colby rd. Close to everything in Winchester and 15 minutes to Lexington. Small dogs with pre-approval and additional fees.All electric, utilities and yard care to be paid by tenant

  401 Cricket Ln Unit 403 Cricket, Winchester, KY 40391
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  /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
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  /30

  Est $184,371 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  3604 Pine Ridge Rd, Winchester, KY 40391

  3604 Pine Ridge Rd, Winchester, KY 40391
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  /28

  $325,000

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft

  398 Pine Ridge Rd, Winchester, KY 40391

  Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
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  /2

  Call for Price

  Cambridge Square Apartments - Income Based

  1 - 3 Beds

  300 C G Stephenson Dr, Winchester, KY 40391

  This community is open by appt only. Office hours are 9am to 12pm and 1pm to 4pm. Please call to schedule your appt!Cambridge Square is a community with beautifully maintained grounds, offering one, two and three bedroom apartment homes with some one bedroom homes reserved for the elderly/dis-abled, all rent based on income. We are located in quiet Winchester, Kentucky, with easy

  300 C G Stephenson Dr, Winchester, KY 40391
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  /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
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  /44

  Est $207,723 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,170 Sq Ft

  2420 Trapp Goffs Corner Rd, Winchester, KY 40391

  2420 Trapp Goffs Corner Rd, Winchester, KY 40391
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  /34

  $312,750

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  123 Strawberry Ln, Winchester, KY 40391

  Priced below recent appraisal this almost new 3 bed 2 bath open layout ranch. This split bedroom design places two bedrooms and the hall bath off the entry and the primary bedroom suite at the rear of the home. The central kitchen offers both a breakfast area and countertop dining at the island, and opens to the family room. Granite kitchen counter tops with stainless steel 50/50 under-mount sink

  Joseph Smallwood Christies International Real Estate Bluegrass

  123 Strawberry Ln, Winchester, KY 40391
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  /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
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  /101

  Est $429,120 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft

  3642 Crowe Ridge Rd, Winchester, KY 40391

  3642 Crowe Ridge Rd, Winchester, KY 40391
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  /48

  $359,000

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft

  356 Boone Ave, Winchester, KY 40391

  **Step into timeless elegance in the heart of downtown Winchester!** This stunning 4-bedroom, 3-full-bath home on historic Boone Avenue has been *completely renovated* while thoughtfully preserving its historic charm. High ceilings, original woodwork, and classic architectural details blend seamlessly with modern updates, offering the best of both worlds. The spacious floor plan features a

  Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391

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