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Winchester Houses for Sale

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  • /17

    $448,000

    • 5 Beds
    • 3 Baths
    • 3,270 Sq Ft

    301 College St, Winchester, KY 40391

    Award-Winning Historic Home - Fully Renovated Gem Across from the ParkThis beautifully restored 5-bedroom, 3 full bath home was completely gutted and reimagined with care. Featuring a custom-built wrap-around porch matching the original design, dual HVAC systems, new sewer line, and a long concrete driveway with rear alley access with more than quarter acre. Best of two worlds- it charm

    Blanca Cheung Tsubaki Group, LLC

    301 College St, Winchester, KY 40391
  • /42

    $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
  • /36

    $414,900

    • 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
  • /31

    $499,000

    • 5 Beds
    • 3 Baths
    • 3,262 Sq Ft

    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
  • /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
  • /39

    $365,000

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

    219 Hampton Ave, Winchester, KY 40391

    Open House-Sunday 2-4 p.m. This beautificcally updated ranch-style home sits on a generous .31 acre lot on a quiet dead end street with mature trees providing shade and privacy. The property features a natural stone front and partial stone skirt(added in 2023), enhancing its curb appeal. Inside, you'll find 4 bedrooms and 2.5 baths., perfect for a large family. The main level boasts a bright

    Jo Gawthrop Keller Williams Bluegrass Realty

    219 Hampton Ave, Winchester, KY 40391
  • /14

    $265,000

    • 3 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    10 Upper St, Winchester, KY 40391

    Modern Ranch residence full un-finished basement, large lot.

    E. Clark Toleman Real Estate Appraisal Services

    10 Upper St, Winchester, KY 40391
  • /34

    $289,900

    • 4 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    410 E Broadway St, Winchester, KY 40391

    Completely remodeled 4 bedroom, 2.5 bath home located in the heart of downtown Winchester. This home features a spacious open floor plan, a first-floor primary suite and a lot of charm. The kitchen, living, and dining areas flow together seamlessly, offering ample space and natural light. Upstairs includes three additional bedrooms and a full bath. Outside, enjoy a large backyard with pool and

    Erin Hurst Bluegrass Properties Group

    410 E Broadway St, Winchester, KY 40391
  • /3

    $345,000

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

    225 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

    225 Evergreen Dr, Winchester, KY 40391
  • /2

    $345,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    215 Evergreen Dr, Winchester, KY 40391

    Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

    Rex Hall United Real Estate Bluegrass

    215 Evergreen Dr, Winchester, KY 40391
  • /42

    $265,500

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft

    9 Apache Trail, Winchester, KY 40391

    Beautiful remodeled move-in ready four bedroom, 2 full bath split foyer. Here are some of the updates: New LVP floors throughout entire home. New carpet on the stairs. New paint throughout home. New fan with remote in living room. Range dishwasher, & new refrigerator stay. New mirrors and lights above them in both baths. New garage door and garage door opener (with 2-year warranty). One side of

    Joyce Ratliff Tom Goebel & Company

    9 Apache Trail, Winchester, KY 40391
  • /13

    $340,000

    • 6 Beds
    • 4 Baths
    • 4,456 Sq Ft

    410 W Lexington Ave, Winchester, KY 40391

    Estate Sale. Selling 'AS IS', in 2024 new roof, walls repaired and freshly painted throughout.Great home for a growing family, covered front porch, 10-foot ceilings upstairs and down, handicap ramp, ample parking in rear. Motivated seller, call for your private showing today

    Melisa McDonald Wrenn Realty

    410 W Lexington Ave, Winchester, KY 40391
  • /32

    $264,900

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft

    528 Estes Dr, Winchester, KY 40391

    Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

    Josh Wood Freedom Realty & Property Management

    528 Estes Dr, Winchester, KY 40391
  • /62

    $269,950

    • 3 Beds
    • 2 Baths
    • 1,247 Sq Ft

    3614 Stamper Dr, Winchester, KY 40391

    Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

    Darrell Tackett Dream Maker Realty, LLC

    3614 Stamper Dr, Winchester, KY 40391
  • /48

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,256 Sq Ft

    40 N Burns Ave, Winchester, KY 40391

    This stunning fully remodeled 3-bedroom, 2-bathroom home is move-in ready with top-to-bottom updates. Every detail has been thoughtfully upgraded, from the modern lighting in every room to the brand-new flooring and fresh paint throughout. The kitchen is a standout with granite countertops, new cabinetry, and brand-new appliances, while the bathrooms boast quartz countertops and elegant tiled

    Ernesto Martinez Berkshire Hathaway HomeServices Foster Realtors

    40 N Burns Ave, Winchester, KY 40391
  • /4

    $369,900

    • 3 Beds
    • 2 Baths
    • 1,635 Sq Ft

    206 Jett Dr, Winchester, KY 40391

    New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

    Mila Ensor Ensor Real Estate, LLC

    206 Jett Dr, Winchester, KY 40391
  • /20

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,443 Sq Ft

    31 Vine St, Winchester, KY 40391

    Welcome to this beautifully updated 3-bedroom, 1-bath home, perfectly situated in the vibrant heart of Winchester. Bursting with charm and character, this home offers the best of modern updates and classic appeal. Step inside to discover a bright, open living area with new flooring, fresh paint, and stylish finishes throughout. The updated kitchen features sleek cabinetry, granite countertops,

    Jana Hooten Rock N' Realty LLC

    31 Vine St, Winchester, KY 40391
  • /19

    $219,000

    • 3 Beds
    • 2 Baths
    • 1,335 Sq Ft

    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
  • /29

    $259,900

    • 3 Beds
    • 2 Baths
    • 1,593 Sq Ft

    306 Snowden Dr, Winchester, KY 40391

    Home is quietly nestled within the Wesleyan Park subdivision just off the Winchester Bypass. While convenient location is obvious this home boast many updates throughout. Including flooring, appliances, New roof, HVAC, Water heater and so much more. Schedule your showing while you can!

    Michael Hilario The Agency

    306 Snowden Dr, Winchester, KY 40391
  • /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
  • /28

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    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
  • /28

    $219,900

    • 3 Beds
    • 1 Bath
    • 1,053 Sq Ft

    228 Forest Ct, Winchester, KY 40391

    This brick ranch style home is located on a quiet cul-de-sac in the residential neighborhood of Forest Park. Enjoy leisurely living in this one level home featuring a 12 X 18 Florida room overlooking a private back yard. The location is minutes from Lexington Avenue and the family/fun Legacy Park. It is move in ready and if you are ready, you may be the next owner. Make an appointment today!

    Craig Bridgewater Bridgewater Real Estate

    228 Forest Ct, Winchester, KY 40391
  • /33

    $179,900

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    307 Blair Ave, Winchester, KY 40391

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

    Brooke Otis-Mull RO&CO Real Estate

    307 Blair Ave, Winchester, KY 40391
  • /9

    $102,000

    • 2 Beds
    • 1 Bath
    • 552 Sq Ft

    39 S Highland St, Winchester, KY 40391

    Here's your chance to own a nice investment property. This Single Family home has 2 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

    David Espinosa Bluegrass Realty Pros, Inc

    39 S Highland St, Winchester, KY 40391
  • /3

    $146,000

    • 3 Beds
    • 1 Bath
    • 1,020 Sq Ft

    228 Jackson St, Winchester, KY 40391

    Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

    David Espinosa Bluegrass Realty Pros, Inc

    228 Jackson St, Winchester, KY 40391
  • /12

    $144,000

    • 3 Beds
    • 1 Bath
    • 805 Sq Ft

    150 Cook Ave, Winchester, KY 40391

    Here's your chance to own a nice investment property. This has a single family has 3 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

    David Espinosa Bluegrass Realty Pros, Inc

    150 Cook Ave, Winchester, KY 40391
  • /22

    $205,000

    • 3 Beds
    • 1 Bath
    • 1,235 Sq Ft

    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
  • /34

    $235,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    37 7th St, Winchester, KY 40391

    Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

    Andrew Fugitt Coldwell Banker McMahan

    37 7th St, Winchester, KY 40391
  • /31

    $245,000

    • 3 Beds
    • 2 Baths
    • 1,201 Sq Ft

    210 Moss Ct, Winchester, KY 40391

    Nice 3 bedroom, 2 bath, all one level, ranch home! Convenient location! Nice patio to sit out back in the mostly privacy fenced in yard. Only needs a few panels to be completely fenced if desired. One car garage. Easy to maintain lot. Large kitchen. Good sized bedrooms. Windows, HVAC, and roof all replaced within the last 8 years. This will make someone a great home!

    Jason Townsend Kentucky Residential Real Estate, LLC

    210 Moss Ct, Winchester, KY 40391
  • /47

    $259,000

    • 3 Beds
    • 2 Baths
    • 1,656 Sq Ft

    17 Euclid Ave, Winchester, KY 40391

    Welcome to 17 Euclid Ave, a charming two-story home in the heart of Winchester! This beautifully maintained property features 3 bedrooms and 2 full baths, offering ample space and comfort. Enjoy the outdoors with a spacious deck perfect for relaxing or entertaining, surrounded by mature trees that provide shade and privacy. Convenient off-street parking ensures easy access, and the home's prime

    Donna Thwaites Thwaites Realtors LLC

    17 Euclid Ave, Winchester, KY 40391
  • /18

    $395,000

    • 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
  • /48

    $219,900

    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft

    59 Holiday Rd, Winchester, KY 40391

    NEW PRICE! With limited inventory on the market, don't wait too long to view this brick ranch that offers comfort, updates, and a spacious outdoor area—all at an affordable price!This home features 3 bedrooms and 1 full bath, with fresh interior paint and newer laminate flooring for a clean, modern feel. The living spaces are filled with natural light, making the home feel warm and

    Kathy Burton Coldwell Banker McMahan

    59 Holiday Rd, Winchester, KY 40391
  • /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
  • /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
  • /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
  • /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
  • /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
  • /3

    $380,000

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

    200 Evergreen Dr, Winchester, KY 40391

    Introducing the Run For The Roses - 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 bathroom. The kitchen

    Rex Hall United Real Estate Bluegrass

    200 Evergreen Dr, Winchester, KY 40391
  • /17

    $195,000

    • 3 Beds
    • 1 Bath
    • 1,059 Sq Ft

    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
  • /26

    $219,900

    • 3 Beds
    • 1 Bath
    • 1,354 Sq Ft

    40 Garner St, Winchester, KY 40391

    Charming & Updated Home in College Park! This beautifully renovated 3-bedroom, 1-bath home in Winchester blends timeless charm with modern updates. Featuring new roof electrical, plumbing, kitchen, flooring, bathroom, fresh paint, and brand-new appliances, this home is truly move-in ready. Situated on a spacious corner lot, it offers ample parking with a rare 3-car garage—perfect for storage or a

    Chaney Hughes Guide Realty, Inc.

    40 Garner St, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 2

Why Live in Winchester

Winchester, nestled in Clark County, offers a blend of historical charm and modern amenities. Known for its beer cheese and Ale-8-One soda, Winchester boasts a thriving local economy with numerous unique recipes. The neighborhood features Victorian-era homes, Sears homes, and newer properties suitable for families, often with spacious lawns and gravel driveways. College Park, centrally located, offers basketball, tennis, hiking, and picnic spots, while Lykins Park provides a playground, skate park, and a nine-hole disc golf course. Legacy Grove Park, a 30-acre space, includes a playground, paved walking paths, and a dog park. Main Street is the hub for dining, with popular spots like La Trattoria and Loma’s, and the Beer Cheese Trail featuring around 15 restaurants with signature recipes. Local attractions include the annual Daniel Boone Pioneer Festival and the Beer Cheese Festival, which draw large crowds. The Bluegrass Heritage Museum showcases Central Kentucky's history. Winchester is 16 miles from Lexington and about 20 miles from Richmond, making it a convenient location for commuters. Clark Regional Medical Center has expanded its services in recent years, enhancing local healthcare options.

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$410,270
Median Single Family Sale Price
$396,605
Median Townhouse Sale Price
$535,000
Median 2 Bedroom Sale Price
$869,000
Median 1 Bedroom Sale Price
$415,000
Average Price Per Sq Ft
$269
Number of Homes for Sale
17
Last 12 months Home Sales
265
Months of Supply
0.80
Median List Price
$412,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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