Map location of
Winchester Traveling Trail, Winchester, KY, USA

Winchester, Kentucky, United States

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Homes for sale near Winchester Traveling Trail, Winchester, KY, USA

Address Bed / Bath Listing Price
Picture of 612 Boone Avenue
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
Winchester, KY
Living Area: 1262 Sqft.
2 Beds, 2 Baths
$200,000
Picture of 404 Wellington Way
404 Wellington Way
This house is located minutes from the Winchester Bypass and within walking distance of the new Clark County Pre-school. The house features 3 bedrooms and 2 full baths. The kitchen is open to a large dining area. The kitchen is supplied with all the appliances. And the house also has a washer and dr
Winchester, KY
Living Area: 1682 Sqft.
3 Beds, 2 Baths
$279,700
Picture of 212 Woodbine Court
212 Woodbine Court
Step right up - come on in! Its appeal is undeniable, both inside and out! Move-in ready. This well-maintained all-brick ranch on a full basement is full of charm and functionality! — Inside, you'll love having two separate living areas, 1 upstairs and 1 in the basement with a wood burning firepl
Winchester, KY
Living Area: 2475 Sqft.
3 Beds, 3 Baths
$349,000
Picture of 300 Calmes Boulevard
300 Calmes Boulevard
Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 4-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *E
Winchester, KY
Living Area: 2636 Sqft.
3 Beds, 3 Baths
$387,000
Picture of 121 Fitch Avenue
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
Winchester, KY
Living Area: 2100 Sqft.
4 Beds, 3 Baths
$379,000
Picture of 136 College Street
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
Winchester, KY
Living Area: 2800 Sqft.
4 Beds, 5 Baths
$399,999
Picture of 110 Hampton Ave Exd
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
Winchester, KY
Living Area: 2516 Sqft.
4 Beds, 3 Baths
$374,900
Picture of 213 Southwind Drive
213 Southwind Drive
Stunning all-brick ranch home with a finished basement! This home features an open kitchen, beautiful hardwood floors, and updated bathrooms. The spacious primary suite is located in the basement and includes access to a screened-in porch — perfect for enjoying your morning coffee or relaxing in t
Winchester, KY
Living Area: 2127 Sqft.
3 Beds, 2 Baths
$260,000
Picture of 23 Kittison Drive
23 Kittison Drive
ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the
Winchester, KY
Living Area: 1346 Sqft.
3 Beds, 2 Baths
$235,000
Picture of 528 Estes Drive
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
Winchester, KY
Living Area: 1904 Sqft.
3 Beds, 2 Baths
$249,900
Picture of 724 Terry Drive
724 Terry Drive
 Charming Split-Level Home in a Peaceful Winchester Neighborhood Discover this beautiful 3-bedroom, 2 full bath split-level home featuring a cozy finished basement perfect for relaxing or entertaining. Enjoy both front and rear porches, ideal for morning coffee or evening gatherings. The spacious,
Winchester, KY
Living Area: 2250 Sqft.
3 Beds, 2 Baths
$279,500
Picture of 363 S Main Street
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
Winchester, KY
Living Area: 2142 Sqft.
3 Beds, 2 Baths
$225,000
Picture of 6 Monroe Avenue
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
Winchester, KY
Living Area: 1305 Sqft.
3 Beds, 2 Baths
$182,000
Picture of 134 Fontaine Boulevard
134 Fontaine Boulevard
Some homes are just houses—but this one was built for connection, creativity, and meaningful moments. Located in the desirable Oak Hill neighborhood, just minutes from GRC High School, this meticulously maintained 4-bedroom, 2.5-bath home offers the space and flexibility today's families are looki
Winchester, KY
Living Area: 2747 Sqft.
4 Beds, 3 Baths
$434,500
Picture of 128 Cherokee Drive
128 Cherokee Drive
Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022, an
Winchester, KY
Living Area: 2082 Sqft.
5 Beds, 2 Baths
$319,900
Picture of 114 Mallard Lane
114 Mallard Lane
Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area we
Winchester, KY
Living Area: 2105 Sqft.
4 Beds, 3 Baths
$372,900
Picture of 536 S Maple Street
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
Winchester, KY
Living Area: 1832 Sqft.
3 Beds, 3 Baths
$352,500
Picture of 213 Hood Avenue
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
Winchester, KY
Living Area: 2244 Sqft.
4 Beds, 3 Baths
$361,000
Picture of 397 Calmes Boulevard
397 Calmes Boulevard
This stunning, renovated home is move-in ready and packed with upgrades that make it an absolute must-see! Step inside and enjoy the fresh, modern feel of the newly painted interior, with updated flooring throughout—including brand-new flooring in the basement, kitchen, and upstairs hall, along wi
Winchester, KY
Living Area: 2637 Sqft.
4 Beds, 4 Baths
$399,550
Picture of 42 Mockingbird Valley Road
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
Winchester, KY
Living Area: 2961 Sqft.
3 Beds, 3 Baths
$457,900
Picture of 103 Hampton Avenue
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
Winchester, KY
Living Area: 1715 Sqft.
3 Beds, 3 Baths
$275,000
Picture of 20 Bon-Haven Avenue
20 Bon-Haven Avenue
Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers ali
Winchester, KY
Living Area: 1850 Sqft.
4 Beds, 3 Baths
$289,000
Picture of 129 Lana Lane
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
Winchester, KY
Living Area: 2844 Sqft.
4 Beds, 3 Baths
$449,000
Picture of 508 Boone Avenue
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
Winchester, KY
Living Area: 2868 Sqft.
3 Beds, 3 Baths
$350,000
Picture of 202 dubuy Drive
202 dubuy Drive
Welcome to this move-in ready 3-bedroom, 2.5-bath home built in 2022. With 1,745 sq. ft., a finished walk-out basement, and thoughtful upgrades, it's designed for comfort with a modern touch. The kitchen features upgraded high-gloss cabinetry, custom granite countertops, and stainless steel appli
Winchester, KY
Living Area: 1800 Sqft.
3 Beds, 3 Baths
$309,000
Picture of 600 Boone Avenue
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
Winchester, KY
Living Area: 4374 Sqft.
4 Beds, 5 Baths
$612,900
Picture of 3614 Stamper Drive
3614 Stamper Drive
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 buil
Winchester, KY
Living Area: 1247 Sqft.
3 Beds, 2 Baths
$259,500
Picture of 102 Ashley Drive
102 Ashley Drive
This cute 3 bedroom and 2 bath home is waiting for you in the quiet neighborhood of Holiday Hills. You will enjoy the convenience to all the things Winchester has to offer as well as easy access to I64 for commuting to Mount Sterling and Lexington. The inside is waiting for you to add your personal
Winchester, KY
Living Area: 1132 Sqft.
3 Beds, 2 Baths
$265,000
Picture of 210 College Street
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
Winchester, KY
Living Area: 2718 Sqft.
4 Beds, 4 Baths
$399,900
Picture of 118 Windridge Drive
118 Windridge Drive
Located in the Windridge neighborhood with easy access to both Bypass Rd and Boone Ave, this charming brick ranch offers 3 bedrooms, 2 full baths, and character throughout. Inside, you'll find hardwood and tile floors (no carpet!), a spacious kitchen with plenty of cabinet space that opens into the
Winchester, KY
Living Area: 1617 Sqft.
3 Beds, 2 Baths
$325,000
Picture of 208 Citation Court
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
Winchester, KY
Living Area: 1568 Sqft.
2 Beds, 2 Baths
$345,000
Picture of 433 Fairholme Way
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
Winchester, KY
Living Area: 2900 Sqft.
3 Beds, 4 Baths
$619,000
Picture of 59 Holiday Road
59 Holiday Road
UPDATED PRICE! Stop paying rent! This brick ranch 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 natur
Winchester, KY
Living Area: 1050 Sqft.
3 Beds, 1 Bath
$214,900
Picture of 410 W Lexington Avenue
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
Winchester, KY
Living Area: 4456 Sqft.
6 Beds, 4 Baths
$340,000
Picture of 40 Garner Street
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
Winchester, KY
Living Area: 1354 Sqft.
3 Beds, 1 Bath
$214,900
Picture of 110 Albany Lane
110 Albany Lane
Lovely one level brick ranch on a corner lot conveniently located in the Meadows just off of McClure Rd. 3 bedroom, 2 full bath with a beautiful yard and a storage building out back.
Winchester, KY
Living Area: 1306 Sqft.
3 Beds, 2 Baths
$275,000
Picture of 186 Chardonnay Court
186 Chardonnay Court
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 livi
Winchester, KY
Living Area: 5290 Sqft.
4 Beds, 3 Baths
$799,999
Picture of 104 Colby Hills Drive
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
Winchester, KY
Living Area: 1950 Sqft.
4 Beds, 2 Baths
$439,000

Points of Interest near Winchester Traveling Trail