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| Address | Bed / Bath | Listing Price |
|---|---|---|
24 N Burns Avenue
Historic charm with all the modern amenities! An inviting front porch and entry lead to a welcoming space warmed by refinished original hardwood floors and a new electric fireplace. Other updates include a brand-new kitchen with granite countertops and new appliances, new lighting fixtures, tile in
Living Area:
2526 Sqft.
|
3
Beds,
4
Baths
|
$309,900 |
314 E Broadway Street
Welcome to this beautifully maintained 3-bedroom, 1-bath ranch offering 1,188 sqft of classic charm on a spacious 0.26-acre lot! This home blends timeless character with thoughtful updates, featuring an inviting single-level layout, bright living areas, well-sized bedrooms, and an updated kitchen wi
Living Area:
1188 Sqft.
|
3
Beds,
1
Bath
|
$229,000 |
22 N Bloomfield Road
Welcome to this beautiful Craftsman style house on a very large lot, with a beautiful backyard. The newly finished stunning original hardwood floors invite you into the living room and family/dining room. There are two functioning wood burning fireplaces one in the family/dining room and another one
Living Area:
1913 Sqft.
|
3
Beds,
2
Baths
|
$318,000 |
117 Buffalo Trace
Move-In Ready! 3 bedrooms, 2 bath, brand new kitchen cabinets with stylish butcher block counter tops, fresh light fixtures throughout, and durable, sleek laminate flooring. This home combines comfort and style with updates that make it truly shine. Perfect for families or first-time home buyers! C
Living Area:
1072 Sqft.
|
3
Beds,
2
Baths
|
$199,900 |
120 Jackson Street
Step into modern comfort just minutes from the heart of downtown Winchester. This nearly new home blends contemporary style with timeless charm. Featuring bright, open living spaces, and thoughtful upgrades throughout, it offers a move-in-ready opportunity in one of Winchester's most convenient loca
Living Area:
1342 Sqft.
|
3
Beds,
3
Baths
|
$248,000 |
246 Geronimo Court
This little cutie sits at the end a cul-de-sac and backs to a farm. I'm not sure it gets much better! This 3 bedroom/2 full bath home is ready for you! The living room opens up into the eat-in kitchen boasting stainless steel appliances. The kitchen leads to the back deck that overlooks your fen
Living Area:
1092 Sqft.
|
3
Beds,
2
Baths
|
$210,000 |
41 7th Street
Welcome to 41 7th Street! This all-brick ranch features 3 bedrooms, 2 full baths, and beautiful hardwood floors throughout the living room, hallway, and bedrooms. Tucked at the end of the street, the property offers added privacy and peaceful farm views behind the home. Enjoy newer windows, a new H
Living Area:
1116 Sqft.
|
3
Beds,
2
Baths
|
$190,000 |
214 S Burns Avenue
Open House Sunday, 1-4PM!!! Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Avenue. This charming home features an inviting wrap-around porch perfect for year-round enjoyment and outstanding curb appeal. Step into a warm and welcoming entryway where refinished
Living Area:
2170 Sqft.
|
4
Beds,
2
Baths
|
$318,500 |
114 Magnolia Street
Great opportunity for investors, flippers, or anyone looking for a project with tons of potential! This 2 bedroom, 1 bath home features a 2 year old roof, giving you a solid head start on future updates. With its convenient location and plenty of possibilities, this property is ready for someone to
Living Area:
910 Sqft.
|
2
Beds,
1
Bath
|
$115,000 |
8 Village Drive
Newly renovated 3 bedroom, 2 full bathroom home located close to downtown, shopping, and medical services as well as College Park which features a indoor pool, tennis, pickleball courts, and much more. Home features all new paint, flooring, updated bathrooms, updated appliances, new lighting, and mu
Living Area:
1979 Sqft.
|
3
Beds,
2
Baths
|
$295,000 |
12 Linden Avenue
Cute ranch with easy access to I-64 and downtown Winchester. 3 bedrooms with 2 full baths with 1 car detached garage with fenced in back yard. This property has a interesting feature of a building that's 14 x 40 that has been a rental but can be used as storage or a mother in-law suite.
Living Area:
Sqft.
|
3
Beds,
2
Baths
|
$240,000 |
205 E Washington Street
PRICE DROP!!! FLIP This House! Seller Has Added A Large Primary Addition And Front Porch. This 4 Bedroom 2 1/1 Bath Home Is Ready For Your Finishes And Has A Fantastic Floor Plan With Large Loft (Whole Home At Stud Level). Finish This Home It Will Be A Showstopper Better Than New Construction Wi
Living Area:
2131 Sqft.
|
4
Beds,
3
Baths
|
$124,900 |
414 Fairholme Way
Welcome to Fairholme Estates—where luxury meets comfort! This brand-new ranch-style home offers 4 bedrooms, 3 full baths, and 9' ceilings throughout for a spacious, airy feel. The designer kitchen features a huge island, beautiful finishes, and flows seamlessly into the vaulted great room filled w
Living Area:
2300 Sqft.
|
4
Beds,
3
Baths
|
$499,900 |
21 Virginia Avenue
Welcome to 21 Virginia Avenue! This updated and well-cared for home offers comfort, flexibility, and room to grow. You'll love the bright living area, the updated flooring, and the beautiful new kitchen. The kitchen offers plenty of workspace, modern finishes, new appliances, butcher-block counte
Living Area:
1749 Sqft.
|
3
Beds,
2
Baths
|
$260,000 |
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 |
357 Crescent Avenue
Welcome to this charming 3-bedroom, 1.5-bath home situated on a lovely corner lot. Step inside to discover a well-maintained interior with a thoughtful layout that flows effortlessly from room to room. The cozy living area opens to the dining space. You'll also find two versatile flex spaces, each f
Living Area:
2188 Sqft.
|
3
Beds,
2
Baths
|
$255,000 |
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
|
$209,900 |
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
Sellers willing to pay towards closing cost! 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 throughou
Living Area:
1274 Sqft.
|
3
Beds,
1
Bath
|
$167,500 |
605 College Street
Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedro
Living Area:
1484 Sqft.
|
2
Beds,
1
Bath
|
$230,000 |
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 |
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 |
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
|
$140,000 |
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 |
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 |
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 |
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 |
208 Citation Court
One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. Great for downsizing or first time homeowner! The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more.
Living Area:
1568 Sqft.
|
2
Beds,
2
Baths
|
$345,000 |
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
Check out this lovely all brick, beautifully renovated 3-bedroom,1bath home located in Winchester perfectly blending timeless charm with modern updates. This move-in ready home features a new roof, updated electrical and plumbing, an upgraded kitchen, new flooring, a fully renovated bathroom, fresh
Living Area:
1354 Sqft.
|
3
Beds,
1
Bath
|
$210,500 |
|
3
Beds,
3
Baths
|
$250,000 |
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 |