581 ft
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Discover the Bluegrass Heritage Museum located at 217 South Main Street in Winchester, Kentucky. This educational and entertaining point of interest is open Monday through Saturday from 12:00 to 16:00. Explore the history and culture of the bluegrass region with exhibits and activities suitable for all ages. Visit the Bluegrass Heritage Museum for a fun and informative experience.
| Address | Bed / Bath | Listing Price |
|---|---|---|
218 E Washington Street
Four Bedroom home in Winchester, Ky which includes a bonus room ready for a makeover for whatever you would like to make it. Enjoy a good sized backyard that is fenced in, along with a detached garage.
Living Area:
1743 Sqft.
|
4
Beds,
1
Bath
|
$225,000 |
612 Boone Avenue
Newly remodeled brick ranch with two bedrooms. There are two bathrooms. One is remodeled and oversized with additional storage. The kitchen has new refrigerator, range and dishwasher. The laundry room is conveniently located at the back door off the concrete back porch. The large back yard is pr
Living Area:
1262 Sqft.
|
2
Beds,
2
Baths
|
$200,000 |
200 Madison Avenue
Charming 3-bedroom, 2-bath ranch featuring a spacious living room and a separate dining area that opens to a back deck—perfect for entertaining or relaxing outdoors. The primary bedroom includes its own private bathroom for added convenience. Enjoy a partially fenced yard with a separate storage s
Living Area:
1124 Sqft.
|
3
Beds,
2
Baths
|
$179,000 |
245 Ecton Road
Welcome to this fully updated home that is cozy and full of character. Featuring brand new central heating and air, electric, drywall, spray foam insulation, kitchen cabinets, water heater, and stunning hardwood floors throughout. This beautiful kitchen boasts all brand new appliances, butcher block
Living Area:
1074 Sqft.
|
3
Beds,
1
Bath
|
$219,900 |
121 Fitch Avenue
This beautifully updated 4-bedroom, 3-bath ranch home includes a private mother-in-law suite, offering flexible living options for guests or extended family. With 2,100 square feet of inviting living space and an attached two-car garage, this home perfectly combines timeless charm with thoughtful mo
Living Area:
2100 Sqft.
|
4
Beds,
3
Baths
|
$379,000 |
136 College Street
Welcome to this exceptional, fully renovated home located in the heart of downtown Winchester. Meticulously redesigned with a thoughtful rear addition, this 4-bedroom, 4.5-bath residence offers the perfect blend of historic charm and modern luxury. Step inside to discover a bright and open floor pl
Living Area:
2800 Sqft.
|
4
Beds,
5
Baths
|
$399,999 |
110 Hampton Ave Exd
Beautifully remodeled 4-bedroom, 3-full bath ranch nestled on a picturesque lot in one of Winchester's most desirable and well-established neighborhoods. Step inside to find a perfect blend of timeless charm and modern updates throughout. The main level offers a spacious and inviting layout with st
Living Area:
2516 Sqft.
|
4
Beds,
3
Baths
|
$374,900 |
175 Magnolia Street
Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the
Living Area:
1046 Sqft.
|
3
Beds,
1
Bath
|
$199,000 |
146 Cook Avenue
Welcome to 146 Cook Avenue in Winchester, Kentucky — an updated home combining classic charm with modern style. This 3-bedroom, 1-bath property offers around 1,274 sq. ft. of comfortable living space with an open-concept layout, newer flooring throughout, and a completely renovated kitchen. The ti
Living Area:
1274 Sqft.
|
3
Beds,
1
Bath
|
$170,000 |
528 Estes Drive
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
Living Area:
1904 Sqft.
|
3
Beds,
2
Baths
|
$249,900 |
363 S Main Street
Built in the 1940s, this 3-bedroom, 2-bath home blends timeless character with thoughtful updates. Enjoy original wood floors, a spiral staircase, a gorgeous fireplace, and an updated kitchen with ample storage. Flexible nooks, a huge master closet, and mudroom add convenience. Outdoor living shines
Living Area:
2142 Sqft.
|
3
Beds,
2
Baths
|
$225,000 |
6 Monroe Avenue
Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifully maintained 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is fill
Living Area:
1305 Sqft.
|
3
Beds,
2
Baths
|
$182,000 |
297 S Main Street
Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy th
Living Area:
3544 Sqft.
|
6
Beds,
4
Baths
|
$335,000 |
536 S Maple Street
No Expense was spared on this beautiful, updated home! The Living Room showcases new hardwood flooring and an electric fireplace with changing lights to set the mood! Updated kitchen with new white cabinets, granite counter tops, tile backsplash and all new appliances for easy entertaining! A dini
Living Area:
1832 Sqft.
|
3
Beds,
3
Baths
|
$352,500 |
213 Hood Avenue
This newly updated 4-bedroom home with lots of character sits in an established neighborhood on just under a half-acre lot in the heart of Winchester. Do you enjoy golfing, tennis, and swimming? Located less than a 5-minute walk to the Winchester Country Club. Great space with over 2200 square feet
Living Area:
2244 Sqft.
|
4
Beds,
3
Baths
|
$361,000 |
208 4th Street
Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile bar
Living Area:
1 Sqft.
|
2
Beds,
1
Bath
|
$150,000 |
120 E Lexington Avenue
Looking for an affordable home? Look no further than this recently updated 3 bedroom 1 bath with possible 4th bedroom or bonus room. New flooring, appliances, fixtures and new hvac. Replacement windows before current owner. Great starter home located convenient to downtown area and shopping.
Living Area:
1332 Sqft.
|
3
Beds,
1
Bath
|
$172,500 |
42 Mockingbird Valley Road
The term 'Move In Ready' really and truly applies here at 42 Mockingbird Valley Road! Versatility, Family Friendly, Well Constructed and Maintained, Mature Landscaping and Quiet Location are among the many attributes you'll find. This beautiful one level home on a full basement is ready for your p
Living Area:
2961 Sqft.
|
3
Beds,
3
Baths
|
$457,900 |
15 Holly Avenue
New Construction! Modern 3 Bedroom, 2 Bath Home Near Downtown Winchester! Step into this beautiful new construction 3 bedroom, 2 full bath home featuring an open concept layout, granite countertops, stainless steel appliances, and stylish finishes throughout. The large backyard boasts a generous d
Living Area:
1200 Sqft.
|
3
Beds,
2
Baths
|
$214,900 |
27 Ashland Avenue
Motivated Seller! Move right in and enjoy this well-maintained 3-bed, 2-bath ranch in the heart of Massie Addition! Thoughtfully updated with a recent roof on both the home and garage, a brand-new hot water heater (2025), and a modern, fresh interior paint palette, this home is ready for you. A hom
Living Area:
1653.1 Sqft.
|
3
Beds,
2
Baths
|
$189,900 |
12 Apache Trail
Welcome to this charming 3-bedroom, 2-full bath ranch located in the desirable Indian Hills Subdivision! This home features a large covered front porch, perfect for relaxing and enjoying your morning coffee or evening sunsets. Inside, you'll find a spacious layout with plenty of potential to make it
Living Area:
1026 Sqft.
|
3
Beds,
2
Baths
|
$168,500 |
103 Hampton Avenue
A timeless brick ranch in one of Winchester's most established neighborhoods on a corner lot. This 3 bedroom, 2.5 bath home offers two living areas and a cozy fireplace. Spacious backyard, covered front porch, and a wrap-around driveway for a private entrance. All just minutes from downtown, schools
Living Area:
1715 Sqft.
|
3
Beds,
3
Baths
|
$275,000 |
129 Lana Lane
Check out the price adjustment! Stunning renovated 4-BR,3BA brick ranch with walkout basement, in-ground pool & pool house! The pool will be winterized this week! See it before the cover goes on! This home has undergone extensive remodeling to improve traffic flow while preserving distinct livin
Living Area:
2844 Sqft.
|
4
Beds,
3
Baths
|
$449,000 |
508 Boone Avenue
3 bedroom, 2 1/2 bath brick home in Witherspoon Subdivision. New roof, new freeze resistant water lines, new heat and air, new appliances, and backsplash. Full basement with double space garage. Spacious formal living room and separate formal dining room. Great room includes breakfast area and s
Living Area:
2868 Sqft.
|
3
Beds,
3
Baths
|
$350,000 |
600 Boone Avenue
Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer an
Living Area:
4374 Sqft.
|
4
Beds,
5
Baths
|
$612,900 |
102 W Hickman Street
102 W Hickman St, Winchester, KY 40391
Cozy and full of potential! This 1½-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
Living Area:
870 Sqft.
|
2
Beds,
1
Bath
|
$171,000 |
31 Vine Street
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
Living Area:
1443 Sqft.
|
3
Beds,
1
Bath
|
$186,500 |
210 College Street
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
Living Area:
2718 Sqft.
|
4
Beds,
4
Baths
|
$399,900 |
208 Citation Court
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 a
Living Area:
1568 Sqft.
|
2
Beds,
2
Baths
|
$345,000 |
433 Fairholme Way
This elegant ranch on a basement offers refined main-level living with upscale finishes throughout. The chef's kitchen is a standout featuring double ovens, custom soft-close cabintry, granite countertops, a large island with seating, a spacious walk-in pantry for entertaining and everyday ease. P
Living Area:
2900 Sqft.
|
3
Beds,
4
Baths
|
$619,000 |
150 Cook Avenue
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.
Living Area:
805 Sqft.
|
3
Beds,
1
Bath
|
$144,000 |
39 S Highland Street
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.
Living Area:
552 Sqft.
|
2
Beds,
1
Bath
|
$102,000 |
228 Jackson Street
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.
Living Area:
1020 Sqft.
|
3
Beds,
1
Bath
|
$146,000 |
410 W Lexington Avenue
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
Living Area:
4456 Sqft.
|
6
Beds,
4
Baths
|
$340,000 |
40 Garner Street
*Seller offering up to $5,000.00 toward buyer's closing costs!!* 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
Living Area:
1354 Sqft.
|
3
Beds,
1
Bath
|
$214,900 |
230 Evergreen Drive
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
Living Area:
1677 Sqft.
|
3
Beds,
2
Baths
|
$380,000 |
265 Evergreen Drive
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 s
Living Area:
1855 Sqft.
|
3
Beds,
2
Baths
|
$430,000 |
270 Evergreen Drive
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 basemen
Living Area:
1677 Sqft.
|
3
Beds,
2
Baths
|
$380,000 |
215 Evergreen Drive
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 expans
Living Area:
1800 Sqft.
|
3
Beds,
2
Baths
|
$345,000 |
225 Evergreen Drive
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 i
Living Area:
1677 Sqft.
|
3
Beds,
2
Baths
|
$345,000 |
250 Evergreen Drive
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 s
Living Area:
1855 Sqft.
|
3
Beds,
2
Baths
|
$430,000 |
220 Evergreen Drive
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 s
Living Area:
1855 Sqft.
|
3
Beds,
2
Baths
|
$430,000 |
205 Evergreen Drive
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, and thoughtful living spaces throughout.
The spa
Living Area:
1855 Sqft.
|
3
Beds,
2
Baths
|
$395,000 |
9 Linden Avenue
Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed
Living Area:
886 Sqft.
|
2
Beds,
1
Bath
|
$139,000 |
|
3
Beds,
3
Baths
|
$250,000 |
104 Colby Hills Drive
(Reducted 50,000) for fast sell. Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room
Living Area:
1950 Sqft.
|
4
Beds,
2
Baths
|
$439,000 |
37 7th Street
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
Living Area:
1680 Sqft.
|
3
Beds,
2
Baths
|
$235,000 |