Winchester, KY Homes for Sale

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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, own the most charming home atop a scenic hill at Blue Ridge Manor, a breathtaking 5.13 acre retreat where modern comfort meets classic elegance. As you drive up the long, private driveway, you'll feel like you're entering your own exclusive retreat, a sanctuary of peace and tranquility. Lovingly maintained by its original owner for the past 30 years, this

  

  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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  /40

  $219,000

  • 2 Beds
  • 2 Baths
  • 1,628 Sq Ft

  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

  (859) 328-1145

  635 Lisletown Ln, 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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  /63

  $439,500

  • 4 Beds
  • 3.5 Baths
  • 3,921 Sq Ft

  259 Hibiscus Ln, Winchester, KY 40391

  IT'S YOUR LUCKY DAY! Due to no fault of the home or sellers, this beauty is BACK ON THE MARKET! This beautiful home blends comfort, space, & charm in a quiet, family-friendly neighborhood.The main level offers a generous living room w/ cozy fireplace for relaxed gatherings, a formal dining room is perfect for special occasions, while the spacious kitchen offers a pantry & casual dining

  Janna Chalfant Smith United Real Estate Bluegrass

  259 Hibiscus Ln, Winchester, KY 40391
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  /27

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft

  5705 Mount Sterling Rd, Winchester, KY 40391

  The one you've been waiting for. This beautiful home has so much to offer. 4 bedrooms, 2 1/2 bathrooms, with full basement and mother in law suite. It sits on just over 3 spacious acres. There is a 24X36 work shop just built in 2022. The roof and HVAC are just 6 years old. The water heater is 6 months old. The property has 10 beautiful apple trees and 3 pear trees. The home is just minutes from

  Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
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  /36

  $469,900

  • 4 Beds
  • 2.5 Baths
  • 2,593 Sq Ft

  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
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  /68

  $500,000

  • 4 Beds
  • 4 Baths
  • 3,523 Sq Ft

  946 Pine Ridge Rd, Winchester, KY 40391

  Custom country home on 8.07+/- acres!!! 4 bed, 4 bath 2 story on a finished basement! Huge insulated and heated detached garage / workshop! Amazing wrap around porch with a back deck! Inside you will find 80 year old oak barnwood flooring, industrial steel wrapped gas log fireplace, very spacious primary suite, cherry cabinets, breakfast bar, laundry room with hidden recycle bins all on the main

  Jason Townsend Kentucky Residential Real Estate, LLC

  946 Pine Ridge Rd, Winchester, KY 40391
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  $419,000

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  188 Big Stoner Rd, Winchester, KY 40391

  Come home every day to this 2-story beauty! You need country life? Well here is it! A little over 1 acre to spread out & enjoy the outdoors w/farm views & beautiful sunsets in the evening. This home opens up to a huge living room with hardwood floors and a vaulted ceiling. Kitchen has all stainless steel appliances & granite counter tops. First floor has a primary suite and a bonus room

  Trina Penn RE/MAX Creative Realty

  188 Big Stoner Rd, Winchester, KY 40391
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  /36

  $360,000

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  208 Citation Ct, Winchester, KY 40391

  One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under. (see photos) Kitchen appliances include

  Garnett Davis Tom Goebel & Company

  208 Citation Ct, Winchester, KY 40391
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  /75

  $535,000

  • 5 Beds
  • 3.5 Baths
  • 3,741 Sq Ft

  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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  /85

  $650,000

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft

  180 Casa Landa Way, Winchester, KY 40391

  This stately yet inviting residence in the highly desirable Stoney Brook subdivision offers the perfect blend of elegance and comfort. Thoughtfully designed for everyday living and entertaining, the home features generously sized rooms throughout.The main level includes formal living and dining spaces, a convenient half bath, and a beautifully appointed kitchen with granite countertops,

  Janna Chalfant Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
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  $419,900

  • 4 Beds
  • 3.5 Baths
  • 2,718 Sq Ft

  210 College St, Winchester, KY 40391

  Welcome to one of Winchester's most iconic and award-winning homes—a stunning 4-bedroom, 3.5-bath historic residence spanning over 2,700 square feet. This exceptional property, recipient of a Historic Preservation Award, beautifully balances timeless character with modern comfort. From the moment you step onto the newly built wide front porch, the home's undeniable charm begins to unfold. Inside,

  Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
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  /36

  $412,900

  • 4 Beds
  • 4.5 Baths
  • 2,800 Sq Ft

  136 College St, Winchester, KY 40391

  Welcome to this stunning, fully renovated 4-bedroom, 4.5-bathroom home in the heart of downtown Winchester. Thoughtfully redesigned with a rear addition, this property now features a spacious first-floor primary suite complete with a private bathroom, walk-in closet, and convenient laundry access.Each of the four bedrooms has its own private en-suite bathroom, offering comfort and privacy

  Danielle Hatton The Brokerage

  136 College St, Winchester, KY 40391
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  /120

  $559,900

  • 6 Beds
  • 3.5 Baths
  • 3,846 Sq Ft

  1953 Cabin Creek Rd, Winchester, KY 40391

  ***Click on the Virtual Tour section to see the video walk through!*** This unique property includes not only one, but two beautiful homes in the heart of Kentucky Bluegrass country. The first home is a brick ranch with a covered front porch and back patio that overlook this beautiful piece of farm land. This 2046 sq ft home contains 3 bedrooms and 2 full baths with a large great room in the

  Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
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  /99

  $749,000

  • 4 Beds
  • 4 Baths
  • 4,644 Sq Ft

  110 Camelot Dr, Winchester, KY 40391

  Don't miss this rare opportunity to abide in one of Winchester's finest locations, Camelot Drive. A hidden gem tucked away in the back of Hampton Manor, this home boasts space and privacy on an idyllic cul-de-sac just off Boone Avenue. Details such as crown molding, built-in cabinetry, high ceilings, 2 fireplaces, transom windows, and hardwood floors fill this home with character and charm.

  Joyce Ratliff Tom Goebel & Company

  110 Camelot Dr, Winchester, KY 40391
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  /58

  $575,000

  • 2 Beds
  • 1.5 Baths
  • 5,054 Sq Ft

  808 Bypass Rd, Winchester, KY 40391

  Unique Mixed-Use Opportunity! This versatile property offers prime potential for a restaurant, cafe, or retail space in a high-visibility location. The commercial space is turn key for a culinary venture or boutique business. Attached is a separate rental unit with private entrance, offering additional income or an ideal live/work setup. Additional space available for potential 2nd Apartment.

  Diana C Brooker Lifstyl Real Estate

  808 Bypass Rd, Winchester, KY 40391
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  $365,000

  • 4 Beds
  • 2.5 Baths
  • 2,929 Sq Ft

  219 Hampton Ave, Winchester, KY 40391

  Open House-Sun 2-4 p.m. This beautiful brick ranch-style home sits on a generous .31 acre lot -property extends to the right, well beyond the fenced area, reaching to the tree stump & pink flag, offering more space, & on a quiet dead end street with mature trees. The property features a natural stone front and partial stone skirt(added in 2023), enhancing its curb appeal. Inside, you'll find

  Jo Gawthrop Keller Williams Bluegrass Realty

  219 Hampton Ave, Winchester, KY 40391
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  /37

  $399,900 Open Sun 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,991 Sq Ft

  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
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  /39

  $472,000

  • 3 Beds
  • 2 Baths
  • 2,727 Sq Ft

  865 Pretty Run Rd, Winchester, KY 40391

  Situated on 1.5 acres along a sought after country road, this one level home features a split bedroom layout with a primary suite that includes an en suite bath and walk in closet. The living room offers vaulted ceilings, hardwood floors, and a gas log fireplace, opening to a dining area and an eat in kitchen. A sunroom provides additional living space with skylights and views of the backyard.

  Shane Underwood Keller Williams Commonwealth

  865 Pretty Run Rd, Winchester, KY 40391
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  /34

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft

  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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  $369,900

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  309 Gallahadion Ct, Winchester, KY 40391

  This beautiful, new-construction home located in desirable Fairholme Estates is a must see!! Amazing open floor plan with kitchen granite countertops, a large island and upgraded Frigidaire Elite Stainless Appliances. The waterproof Pergo laminate flooring is throughout the home. The builder has installed window blinds throughout the home and stained the back deck. Don't miss the primary

  Josh Wood Freedom Realty & Property Management

  309 Gallahadion Ct, Winchester, KY 40391
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  /18

  $389,900

  • 3 Beds
  • 3 Baths
  • 2,516 Sq Ft

  110 Hampton Ave, Winchester, KY 40391

  Move-in ready mid- century brick ranch home! Features 3 bedrooms, 3 full baths, new kitchen with granite countertops, 3 woodburning fireplaces, formal dining or family room, full basement with huge rec room or space to have 4th bedroom, 1 car garage, 2 storage buildings & fenced in yard! Updates include windows, doors, metal roof, new paint inside & out, new flooring in basement & bedrooms, all

  Angie Conley Dixon Dixon Properties

  110 Hampton Ave, Winchester, KY 40391
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  /57

  $357,000

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

  356 Boone Ave, Winchester, KY 40391

  Step into timeless charm with this beautifully renovated home on one of Winchesters most historic streets. Built over 100 years ago, this 3200 sq ft residence blends classic character with modern updates. You will love the updated kitchen featuring granite countertops, stainless appliances and plenty of space for cooking and entertaining in the large dining room. This home showcases re-tiled

  Nancy Smith Rector Hayden Realtors

  356 Boone Ave, Winchester, KY 40391
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  /3

  $380,000

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  270 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  265 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, walkout unfinished basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  265 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
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  /3

  $380,000

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  230 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  230 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  220 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

  Rex Hall United Real Estate Bluegrass

  220 Evergreen Dr, Winchester, KY 40391
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  /36

  $324,900

  • 4 Beds
  • 2 Baths
  • 2,430 Sq Ft

  510 Kimberly Dr, Winchester, KY 40391

  Welcome to 510 Kimberly Drive! This charming 4-bedroom, 2-bath home blends classic character with modern comfort, offering over 2,400 sq ft of inviting living space. You'll love the warm hardwood floors, cozy fireplace, and versatile bonus room perfect for a sunroom or breakfast nook. The fully finished basement expands your possibilities with an additional flex room ideal as a fifth bedroom,

  Ashley Barreto Indigo & Co

  510 Kimberly Dr, Winchester, KY 40391
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  /25

  $250,000

  • 4 Beds
  • 2.5 Baths
  • 3,024 Sq Ft

  816 Stratton Ln, Winchester, KY 40391

  Welcome to your dream home! Nestled in an excellent location in Winchester, KY, this charming 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort and convenience. Enjoy the backyard, ideal for outdoor entertainment and relaxation, as well as the inviting front deck, perfect for sipping your morning coffee or watching the sunset. The above ground pool stays with the home and will be a

  Haley Rollins Dream Maker Realty, LLC

  816 Stratton Ln, Winchester, KY 40391
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  /14

  $330,000

  • 4 Beds
  • 2 Baths

  3431 Colby Rd, Winchester, KY 40391

  This sprawling all stone ranch is waiting for someone to come bring it back to life! The hard part has been done, now it's ready for the finishing touches. Prime location! Easy access to Lexington and 1.5 miles away form the Winchester bypass. Situated on 3.1 acres.

  Holly Goeing The Agency

  3431 Colby Rd, Winchester, KY 40391
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  /37

  $1,595,000

  • 37 Beds
  • 19.5 Baths
  • 26,124 Sq Ft

  2 N Main St, Winchester, KY 40391

  Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule!The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC

  Blanca Cheung Tsubaki Group, LLC

  2 N Main St, Winchester, KY 40391
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  /41

  $259,900

  • 3 Beds
  • 2.5 Baths
  • 1,544 Sq Ft

  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
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  /3

  $230,000

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  106 W Hickman St, Winchester, KY 40391

  106 W Hickman St, Winchester, KY 40391This charming 11⁄2-story home is currently used as a rental and features 3 bedrooms and 2 bathrooms, offering plenty of space for comfortable living. The well-laid-out floor plan provides a welcoming atmosphere with ample natural light and a functional flow between rooms. Located in a convenient Winchester neighborhood, close to schools, shopping, and

  David Espinosa Bluegrass Realty Pros, Inc

  106 W Hickman St, Winchester, KY 40391
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  /6

  $171,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  102 W Hickman St, Winchester, KY 40391

  102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

  David Espinosa Bluegrass Realty Pros, Inc

  102 W Hickman St, Winchester, KY 40391
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  /3

  $251,000

  • 6 Beds
  • 3 Baths
  • 2,302 Sq Ft

  133 S Highland St, Winchester, KY 40391

  16 Central Ave, Winchester, KY 40391Prime multi-family investment in a great Winchester location! This 2-story property features two spacious rental units, both offering strong income potential. The first unit includes 3 bedrooms and 2 bathrooms, while the second unit offers 3 bedrooms and 1 bathroom—ideal for accommodating a range of tenant needs. With an established rental history and close

  David Espinosa Bluegrass Realty Pros, Inc

  133 S Highland St, Winchester, KY 40391
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  /2

  $131,000

  • 2 Beds
  • 1 Bath
  • 804 Sq Ft

  206 Chaplin Ave, Winchester, KY 40391

  206 Chaplin Ave, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

  David Espinosa Bluegrass Realty Pros, Inc

  206 Chaplin Ave, Winchester, KY 40391
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  /3

  $290,000

  • 6 Beds
  • 4 Baths
  • 2,511 Sq Ft

  16 Central Ave, Winchester, KY 40391

  16 Central Ave, Winchester, KY 40391Excellent multi-family investment opportunity in a convenient Winchester location! This 11⁄2-story property features two spacious rental units, offering strong income potential. The first unit boasts 4 bedrooms and 3 bathrooms, providing ample space for larger households. The second unit includes 2 bedrooms and 1 bathroom, perfect for smaller families or

  David Espinosa Bluegrass Realty Pros, Inc

  16 Central Ave, Winchester, KY 40391
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  /3

  $224,000

  • 3 Beds
  • 1 Bath
  • 1,645 Sq Ft

  136 Alabama St, Winchester, KY 40391

  136 Alabama St, Winchester, KY 40391Charming 11⁄2-story home with investment potential! Currently used as a rental, this property offers 3 bedrooms and 1 bathroom, making it a great option for tenants seeking comfort and convenience. The home's layout features a spacious main level with living and dining areas, plus additional space upstairs. Located on a quiet street yet close to schools,

  David Espinosa Bluegrass Realty Pros, Inc

  136 Alabama St, Winchester, KY 40391
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  /3

  $426,000

  • 5 Beds
  • 4 Baths

  1028 W Lexington Ave, Winchester, KY 40391

  1028 W Lexington Ave, Winchester, KY 40391Investor's dream in the heart of Winchester! This 11⁄2-story property features four rental units, offering a great mix of layouts to appeal to a variety of tenants. The main unit includes 2 bedrooms and 1 bathroom, while the remaining three units each offer 1 bedroom and 1 bathroom, providing consistent rental income potential. With its established

  David Espinosa Bluegrass Realty Pros, Inc

  1028 W Lexington Ave, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 5

Why Live in Winchester

Winchester, KY, the largest city in Clark County, is known for its vibrant community and unique local flavors, including the birthplace of beer cheese and Ale-8-One soda. Main Street is the hub for dining, featuring popular spots like La Trattoria and Loma’s, and the Beer Cheese Trail, which includes around 15 restaurants with signature beer cheese recipes. The city offers practical amenities with nearby grocery stores like Kroger and Walmart Supercenter, and retail options such as TJ Maxx and Lowe’s. Housing in Winchester includes Victorian-era inspired homes and newer subdivisions, with properties often featuring gravel driveways and spacious lawns suitable for gardens. Clark County Public Schools provide strong academic programs, including AP and dual enrollment courses at George Rogers Clark High School. For outdoor activities, residents enjoy Legacy Grove Park, College Park, and Lykins Park, which offer facilities for basketball, tennis, hiking, and disc golf. Winchester hosts annual events like the Beer Cheese Festival and the Daniel Boone Pioneer Festival, attracting visitors with arts, crafts, and food. The Bluegrass Heritage Museum showcases the history of Central Kentucky. Commuting is convenient with Winchester located 16 miles from Lexington and 20 miles from Richmond. The city has a cooperative community spirit, bolstered by investments from younger residents and a thriving local economy.

Learn more about living in Winchester

Frequently Asked Questions

What is the average home price in Winchester, KY?

Homes for sale in Winchester, KY have an average home price of $454,398.

How many homes have sold over the last 12 months in Winchester, KY?

59 homes have sold in Winchester, KY over the last 12 months.

Is Winchester, KY a safe city?

In general, the safest neighborhood in Winchester, KY with lower crime scores is Becknerville.

What are the most popular zip codes in Winchester, KY?

The most popular zip codes in Winchester, KY include 40391, 40361, 40353, 40516 and 40475.

What are the most popular neighborhoods in Winchester, KY?

The most popular neighborhoods in Winchester, KY with the most homes for sale are Old Pine Grove, Becknerville and Wyandotte.

How much do you need to make to afford a house in Winchester?

The median home price in Winchester is $380,000. If you put a 20% down payment of $76,000 and had a 30-year fixed mortgage with an interest rate of 6.63%, your estimated principal and interest payment would be $1,950 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $84K a year to afford the median home price in Winchester.

How are the schools in Winchester, KY?

Winchester, KY has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Strode Station Elementary School, Baker Intermediate School and George Rogers Clark High School. The neighborhoods in Winchester with the highest rated schools are Old Pine Grove, Becknerville and Wyandotte. Browse all the schools in Winchester, KY to learn more.

Home Trends in Winchester, KY

On average, homes in Winchester, KY sell after 27 days on the market compared to the national average of 70 days. The median sale price for homes in Winchester, KY over the last 12 months is $233,000, down 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$233,000

Median Single Family Sale Price

$380,000

Median Townhouse Sale Price

$225,000

Average Price Per Sq Ft

$229

Number of Homes for Sale

14

Last 12 months Home Sales

59

Months of Supply

2.80

Median List Price

$380,000

Median Change From 1st List Price

1%

Median Home Sale Price YoY Change

-7%