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213 Hood Ave, Winchester
$354,000
4 Beds ⋅ 3 Baths ⋅ 25501832 MLS
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 with plenty of storage space and a 2-car garage. Step inside and check out all the updates! New AC system with a newer well maintained gas furnace, new concrete front porch, updated lighting and fresh paint throughout with crown molding on the first floor. The updated kitchen includes new cabinetry, quartz cabinetry and stainless appliances. The half bath has new tile flooring and a custom vanity. The primary bathroom has a custom tiled shower with a double vanity and new tile floor. The guest bathroom has new flooring and a custom vanity. The cozy living room has new gas logs. The large family room is open to the kitchen for ease of entertaining. The backyard is private with a large back patio. The 4th bedroom would make a great office space as well. Make an appointment for a tour today.

213 Hood Ave, Winchester

220 Hibiscus Ln, Winchester
$350,000
3 Beds ⋅ 2 Baths ⋅ 26007618 MLS
Welcome home to this immaculate gem nestled in the charming Hibiscus Terrace Subdivision! This beautifully maintained three-bedroom, two-bathroom home offers 1,640 square feet of thoughtfully designed living space that blends comfort with everyday functionality. Inside, discover a warm, inviting interior where fresh carpet installed in 2022 greets you with plush softness throughout. The well-planned layout provides generous living areas perfect for both quiet evenings and lively gatherings with friends and family. Each bedroom offers ample space and natural light, with the primary bedroom serving as a true retreat after long days. The kitchen and living areas flow seamlessly, creating an open atmosphere that makes this home feel even more spacious than its square footage suggests. Every corner reflects the pride of ownership that has gone into maintaining this property at its absolute best. Outside, the screened-in back deck is nothing short of a personal oasis. Imagine sipping your morning coffee without a single mosquito daring to interrupt your peace. The spacious two-car garage provides plenty of room for vehicles, storage, and weekend projects alike. Location lovers will appreciate the proximity to George Rogers Clark High School and the Winchester Traveling Trail, making this home ideal for those who value both education and outdoor recreation. The surrounding neighborhood offers a quiet, welcoming atmosphere with friendly curb appeal at every turn. Schedule your private showing today and prepare to fall in love!

220 Hibiscus Ln, Winchester

121 Fitch Ave, Winchester
$349,000
4 Beds ⋅ 3 Baths ⋅ 25504324 MLS
*Under contract with a 48-hour kick out clause. Please continue to show and bring offers* 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 modern updates. Conveniently located just minutes from the interstate close to Lexington, it offers easy access to everything while providing the comfort, character, and style you've been looking for! Inside, you'll find gleaming wood floors, updated light fixtures, and a stunning kitchen with granite countertops, a tile backsplash, and new cabinet doors. Just wait until you see the bathrooms! They have been refreshed with new toilets, and the washer and dryer are included for your convenience. Relax on the covered front porch accented by a new grey cobblestone walkway on the front and back patios, or entertain guests on the private rear patio and huge green yard—this home truly has it all!

121 Fitch Ave, Winchester

411 Boone Ave, Winchester
$349,000
4 Beds ⋅ 3 Baths ⋅ 26015962 MLS
Gracious, comfortable Cape Cod on a beautiful double lot directly across from the Winchester Country Club (golf, swimming, and tennis). With only three owners, this well-loved home offers exceptional space and an unbeatable location. THE SPACE: The front door opens to a generous foyer with a coat closet. The welcoming living room features a fireplace, abundant windows, and French doors leading to a delightful sunroom. The oversized dining room is ideal for entertaining, while the charming eat-in kitchen offers generous counter space and a second entrance to the sunroom. The massive family room, with its own fireplace and sliding doors to the rear deck, offers endless possibilities—family room, playroom, home office, exercise space, or even the foundation for a first-floor primary suite. A half bath and laundry complete the main level. Upstairs you'll find four bedrooms and two full baths. The spacious primary bedroom is adjacent to the main bath featuring a soaking tub, separate shower, and double vanity. The second bedroom is generously sized and overlooks the front yard. The third bedroom is perfect for an office or nursery. A second full bath is located within the large fourth bedroom above the family room. Two staircases—one from the foyer and one from the family room—add flexibility to the home's layout. THE LOT: The .43-acre double lot is shaded by mature trees, providing beauty and privacy with room to relax, garden, or play. THE LOCATION: Directly across from Winchester Country Club and within walking distance of the Clark County Public Library (.5 mile), downtown Winchester (.8 mile), Clark County Parks & Recreation (.7 mile), and Robert D. Campbell Junior High (.4 mile). Less than three miles from I-64, Kroger, Lowe's, Walmart, Rural King, Starbucks, Chipotle, restaurants, and more. Small town living just 15 miles to Hamburg in Lexington, where you'll find extensive dining and shopping including Malone's, Target, Barnes & Noble, Costco. If you or your children have been priced out of other Central Kentucky markets, discover the value Winchester still offers—and the opportunity to get in before the next wave of growth. Winchester - where history meets progress. Home of Beer Cheese, 19k+ people, 8k households, and 440+ businesses including Ale-8-1.

411 Boone Ave, Winchester

205 Chardonnay Ct, Winchester
$345,000
4 Beds ⋅ 3 Baths ⋅ 25018066 MLS
This charming 4-bedroom, 2.5-bath home with a classic white picket fence sits on a quiet cul-de-sac in Fontaine Estates. Inside, the versatile layout offers space for every occasion—a formal dining room for special gatherings, a bright sunroom for morning coffee, a comfortable living room, and a cozy family room featuring a masonry fireplace with built-ins. The eat-in kitchen is perfect for casual meals, while the laundry room and two-car garage add everyday convenience. Outside, imagine kids riding bikes safely in the cul-de-sac, evenings spent by the fire pit, and relaxed afternoons in your own backyard oasis. This home is ready for you to make it your own and create memories that will last a lifetime.

205 Chardonnay Ct, Winchester

145 Shanahan Ln, Winchester
$345,000
4 Beds ⋅ 3 Baths ⋅ 25506693 MLS
This 4-bedroom, 3-bath ranch on a basement offers over 2,500 sq ft of living space with modern updates, a welcoming layout and a safe neighborhood to live in. The large living room with cathedral ceilings flows into a well-appointed kitchen featuring ample counter space and newer appliances. New LVP flooring runs throughout the main level, while new patio doors open to a large deck; perfect for entertaining or relaxing evenings. You will enjoy a nice primary bedroom and bath on the main level, with 2 additional, good sized bedrooms or office space. Downstairs, the partially finished walkout basement adds 960 finished sq ft with flexible living space, a full bath, and easy access to the backyard. Situated in a quiet, safe neighborhood with sidewalks ideal for kids, walking, or biking, and conveniently close to local schools, this home blends comfort and convenience in one.

145 Shanahan Ln, Winchester

103 Mayfair Ct, Winchester
$345,000
3 Beds ⋅ 2 Baths ⋅ 25501461 MLS
This well-maintained ranch offers 3 bedrooms, 2 full baths, and a 3-car garage that's insulated, heated, and wired with a — Looks good. The garage has a 100amp service, 3each. 220v 30amp breakers—ideal for hobbies or extra storage. The property sits on a great lot with a fenced-in backyard, perfect for both privacy and entertaining. Inside, the split-bedroom design separates the secondary bedrooms from the primary suite. You'll enjoy vinyl plank flooring throughout the main living areas, with carpet in the bedrooms for added comfort. The kitchen features granite countertops and stainless steel appliances, while the nine-foot smooth ceilings throughout create an open, airy feel. The unfinished walk-out basement is roughed in for a full bath, offering endless possibilities for future expansion. A blend of practicality and style, this Colby Ridge home is ready for its next owner!

103 Mayfair Ct, Winchester

341-345 Carolina Ave, Winchester
$345,000
9 Beds ⋅ 6 Baths ⋅ 26020069 MLS
Exceptional investment opportunity! This fully occupied triplex is a turnkey addition to any investment portfolio, offering three spacious units, each with approximately 1,116 square feet, 3 bedrooms, and 1.5 bathrooms. With strong rental potential and separately metered utilities paid by the tenants, this property provides an excellent income-producing opportunity. Each unit features a well-designed two-story floor plan with a welcoming foyer, spacious living room, kitchen, utility area, and half bath on the main level. Upstairs, you'll find three generously sized bedrooms and a full bathroom, creating a comfortable layout that appeals to long-term tenants. Additional features include private decks, ceiling fans, window blinds, ample off-street parking, and generously sized yards. Conveniently maintained and fully leased, this multifamily property offers immediate cash flow with minimal owner responsibilities. Showings are available by appointment only with advance notice to accommodate the tenants.

341-345 Carolina Ave, Winchester

119 Gibson Way, Winchester
$345,000
4 Beds ⋅ 3 Baths ⋅ 26014834 MLS
Updated Price, below Apprisal value...Space, Location, and Great Finishes....4 bedrooms, 2.5 bathrooms, walk in sit down and relax...Dining Room/Living Room or Office welcomes you as you enter from the covered front porch. Guests can use the 1/2 bathroom on the main level...Open Kitchen and Family Room with granite counter tops, breakfast bar, and large pantry making cooking easy, 10 ft ceilings on the mail level offer a more open feel. Upstairs you will find a large laundry room 3 bedrooms a guest bathroom with double vanity! The primary bedroom offers plenty of room, double vanity bathroom, and custom walk-in closet. Outside the yard is fenced with vinyl style fencing, a patio for grilling and 2 car attached garage for your vehicles and storage. This home has all the space and it's priced to sell!

119 Gibson Way, Winchester

538 S Maple St, Winchester
$344,000
3 Beds ⋅ 3 Baths ⋅ 26000925 MLS
Be the first to call this stunning new construction home! Perfectly situated in the heart of Winchester, this two-story residence offers a fresh, modern feel with convenience at your doorstep. Step inside to discover a bright and airy open-concept main level, featuring durable and stylish Luxury Vinyl Plank (LVP) flooring throughout. The kitchen is a true showstopper, boasting crisp white cabinetry, gleaming quartz countertops, stainless appliances, and a large center island that overlooks the spacious great room—ideal for entertaining guests or keeping an eye on the family. A convenient half bath rounds out the main floor. Upstairs, you will find three comfortable bedrooms and pristine bathrooms finished with elegant tile work. The primary bedroom features a vaulted ceiling, lots of natural light, walk-in closet and en-suite bathroom with tile flooring, dual sink vanity, and step in shower! The guest bedrooms are a lovely size with lot of natural light and a guest bathroom to share with dual sink vanity and a tub/shower combo with tile surround. If you are looking for low-maintenance luxury and a prime location, this is the one. You will love the expansive back yard while sitting on your lovely deck. Extra features include a combination of casement and traditional windows, a fully insulated garage and garage doors, 2x6 construction, and poured wall foundation crawl space (not block). Located on a quiet, established street, you will love it!

538 S Maple St, Winchester

212 Woodbine Ct, Winchester
$344,000
3 Beds ⋅ 3 Baths ⋅ 25505033 MLS
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 fireplace in both rooms. Enjoy the cold winter evenings in front of either of the fireplaces with family and friends. The main level has Glistening Bamboo Flooring, updated kitchen with stainless appliances and gas range. The open living area and spacious kitchen has features like an oversized island plus a dining area, making the perfect set-up for large gatherings and entertainment. The primary suite offers large closet and a private full bath, plus 2 additional bedrooms and a full bath. The basement has an abundance of additional living space, a separate laundry room—with a half bath and a washer/dryer (which stays). The 2-car garage provides additional room for your cars or extra storage. The back deck is perfect for cooking out or just relaxing. Other recent updates includes: fresh paint, replaced roof, installed gas heating system, new front sidewalk and back deck. With modern updates and room to add your personal touch, this home is a fantastic opportunity you don't want to miss. Schedule your private showing today!

212 Woodbine Ct, Winchester

356 Boone Ave, Winchester
$340,000
4 Beds ⋅ 3 Baths ⋅ 25501566 MLS
**Step into timeless elegance in the heart of downtown Winchester!** This stunning 4-bedroom, 3-full-bath home on historic Boone Avenue has been *completely renovated* while thoughtfully preserving its historic charm. High ceilings, original woodwork, and classic architectural details blend seamlessly with modern updates, offering the best of both worlds. The spacious floor plan features a beautifully updated kitchen with custom cabinetry and stainless steel appliances, inviting living and dining spaces perfect for entertaining, and three luxurious full baths with contemporary finishes. Each bedroom is generous in size, with the primary suite offering a serene retreat. Enjoy outdoor living with a welcoming front porch and private backyard, just steps from local shops, dining, and Winchester's vibrant downtown. With careful attention to detail and a balance of character and comfort, this home is truly move-in ready and one-of-a-kind. On the National Register of Historic Places, this home is part of the historic Thomson Subdivision. Built between 1905-1910 it was originally the property of Sarah French. The French family was a prominent Winchester family and Sarah was first married to Henry Youtsey who was convicted in the conspiracy to assassinate Governor William Goebel, she divorced Henry while he was in prison and later remarried. Own a part of Kentucky history!

356 Boone Ave, Winchester

168 Buckingham Ln, Winchester
$340,000
4 Beds ⋅ 3 Baths ⋅ 26006049 MLS
Tucked away on a quiet cul-de-sac, this well-maintained 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and convenience. Featuring a 2-car garage plus an additional covered carport ideal for a boat, RV, or extra parking, this property is designed to fit a variety of lifestyles. Inside, you'll find a functional layout with a separate office and formal dining room, perfect for both everyday living and entertaining. The owner refreshed the home since purchasing with new paint and installed luxury vinyl plank flooring throughout the main living areas downstairs, giving it a clean, updated feel. Step outside to enjoy your own backyard retreat, complete with an above-ground pool featuring a new liner and updated decking, as well as raised garden beds ready for its next owners. Located just minutes from Kroger, Walmart, Downtown Winchester, and Boonesborough State Park—and only about 20 minutes to both Lexington and Richmond—this home offers peaceful living with unbeatable convenience. Don't miss your chance to make it yours!

168 Buckingham Ln, Winchester

1270 Sewell Shop Rd, Winchester
$340,000
5 Beds ⋅ 2 Baths ⋅ 26000914 MLS
Country Living with Convenience — 5 Fenced Acres in Winchester, KY Enjoy the perfect blend of peaceful country living and easy access to town with this well-maintained home on 5 fully fenced acres in Winchester, KY. Conveniently located just 30 minutes to Lexington, 5 miles to I-64, 10 minutes to Mt. Sterling, and 15 minutes to Winchester, this property offers country living without sacrificing convenience. Step inside to a spacious, functional layout featuring 5 bedrooms and 2 full bathrooms, offering room for everyone—whether you need extra bedrooms, a home office, playroom, or guest space. The home provides comfortable everyday living, a welcoming main living area, and an open feel that makes it easy to entertain or relax. Outside, you'll love the gated entrance and fully fenced acreage, ready for cattle, livestock, or hobby farming. The chicken coop stays, making it easy to start your homestead lifestyle right away. Modern conveniences include Spectrum fiber-optic internet availability and an ADT security system that remains. If you've been searching for room to roam, a property set up for animals, and country charm close to town—this one checks every box. Schedule your showing today!

1270 Sewell Shop Rd, Winchester

740 Pilot Ridge Ln, Winchester
$340,000
3 Beds ⋅ 3 Baths ⋅ 26006680 MLS
Tucked away on 1.25 fully fenced acres, this custom-built home offers some of the most breathtaking views in Winchester. Designed with charm and comfort in mind, this 3-bedroom, 2.5-bath home blends modern convenience with timeless farmhouse style. Step inside to an open, inviting layout filled with natural light and warm finishes throughout. The spacious vaulted master suite is a true retreat, featuring soaring ceilings and a massive walk-in closet that provides both luxury and functionality. The heart of the home flows effortlessly into a beautiful screened-in back porch—perfect for relaxing mornings or peaceful evenings while taking in the serene country landscape. Whether you're entertaining or enjoying quiet moments, this property delivers the perfect balance of privacy, style, and scenic beauty—all just minutes from town.

740 Pilot Ridge Ln, Winchester

27 Hampton Ave, Winchester
$340,000
3 Beds ⋅ 2 Baths ⋅ 26010286 MLS
Located on desirable Hampton Avenue, this all-brick ranch is full of timeless character and thoughtful updates. Beautiful original hardwood floors run throughout the main level, highlighted by detailed craftsmanship and charm you don't find every day. The spacious living room features built-ins, a fireplace, and flows into the dining area, creating a warm and inviting space for everyday living or entertaining. Just off the main level, the three-seasons room offers the perfect spot for hosting guests, relaxing, or enjoying views of the backyard year-round. All three bedrooms and two full baths are conveniently located on the main level, including one bath that has been recently updated. Downstairs offers additional living space along with a laundry area, providing flexibility for a second den, office, or hobby space. Outside, you'll find a side-entry two-car attached garage and a beautifully landscaped backyard with a charming setting perfect for relaxing or entertaining.

27 Hampton Ave, Winchester

221 W Hickman St, Winchester
$339,500
4 Beds ⋅ 3 Baths ⋅ 26013573 MLS
Step inside this beautifully remodeled historic home and you'll immediately understand why homes like this are so special. With loads of space, four bedrooms, and three full bathrooms, this home offers the character buyers love with the modern updates they need. Every detail has been thoughtfully refreshed while preserving the charm and warmth that make historic homes so hard to duplicate. From the spacious rooms to the inviting natural flow, this home feels both timeless and move-in ready. The heart of the home is the stunning gourmet kitchen -- beautifully updated and ready for everyday living, entertaining, and gathering with family and friends. Major updates have already been completed, including updated electric, plumbing, and HVAC, giving buyers added peace of mind. The first-floor bedroom and full bathroom create flexibility for guests, a home office, or multi-generational living. Upstairs, the spacious primary suite offers a private bathroom and walk-in closet, giving you the comfort and function today's buyers are looking for. Located near the heart of downtown Winchester, you'll love being close to local shops, dining, and the charm of a welcoming community. This is more than just a remodeled home -- it is a rare opportunity to own a piece of history without sacrificing modern comfort. Beautifully restored, thoughtfully updated, full of character, and ready for its next owner.

221 W Hickman St, Winchester

107 Gibson Way, Winchester
$339,000
3 Beds ⋅ 3 Baths ⋅ 26013361 MLS
A beautiful designed spacious house that offers 3 bedrooms, 3 full bathrooms, and 2266 sq ft og thoughtfully designed living space. Step inside to discover an open-concept layout perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the main living areas, creating a warm and inviting atmosphere. Generously sized bedrooms provide comfort and privacy, while the flexible floor plan offers space to fit your lifestyle. Located in a growing Winchester community, you'll enjoy the small-town living with convenient access to shopping, dining, schools, and major roadways. Don't miss your opportunity to own this beautiful home. The home features custom made window blinds as a plus. There is a preschool and two elementary schools within walking distance! Quiet neighborhood.

107 Gibson Way, Winchester

536 S Maple St, Winchester
$335,000
3 Beds ⋅ 3 Baths ⋅ 25501757 MLS
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 dining room with a pantry make storage and dinner a breeze! 3 generous sized bedrooms, 3 full bathrooms with excellent classic tile work on the flooring, showers and around the primary bathtub, new modern classic cabinetry, fixtures, and countertops. You can welcome guest on the covered from pouch and entertain on your covered back deck. Alley access allows easy parking under the carport. This is not your average remodel, classic details, attention to detail with updates for modem convivences, you will love this home!

536 S Maple St, Winchester

201 Boone Ave, Winchester
$335,000
4 Beds ⋅ 3 Baths ⋅ 26007703 MLS
Beautifully updated historic cottage-style home in Winchester's Historic Thomson Neighborhood featuring a recently updated wraparound front porch, and a new roof installed in September 2024. Inside, this character-filled home offers original hardwood floors, tall ceilings, classic millwork, four decorative fireplaces, a spacious, updated kitchen, and a formal dining room. Just off the entry/sitting room, the family room can be closed off with a large pocket door for added privacy and flexibility. The floor plan also includes primary bedroom options on both the main level and upstairs, each with a full bath, plus a half bath on the main level. Upstairs features two large bedrooms, a separate oversized sitting room that could serve as a fifth bedroom, and a massive walk-in closet adjoining the upstairs primary bedroom. Situated on one of the largest in-town corner lots, this home also offers off-street parking, a storage shed, is just two blocks from College Park, and is minutes from downtown Winchester's shops and restaurants.

201 Boone Ave, Winchester

120 Pilot View Rd, Winchester
$334,000
3 Beds ⋅ 3 Baths ⋅ 26003979 MLS
Charming 1930 farmhouse that perfectly blends timeless character with modern updates, situated on 5 beautiful acres. This fully remodeled home offers 3 bedrooms, 2.5 baths, and a spacious bonus room currently used as a home office. Inside, you'll find a formal dining room, updated living spaces, and a large laundry room where the washer and dryer convey. Major improvements include a new roof (2021), updated HVAC system and ductwork (2023), new tankless water heater (2023), spray foam insulation added to the crawlspace, and a new septic pump for peace of mind. The property is ideal for those seeking space and functionality, featuring a 2,280 sq ft tobacco barn and a 1,240 sq ft detached garage with ample storage and workshop potential. For buyers interested in homesteading or gardening, the chicken coop, bee hive, and raised garden beds can remain. A rare opportunity to enjoy historic charm, modern upgrades, and country living just minutes from town. Buyer to verify schools and property square feet.

120 Pilot View Rd, Winchester

35 Mockingbird Valley Rd, Winchester
$330,000
3 Beds ⋅ 3 Baths ⋅ 25501905 MLS
A ranch in one of the most desirable neighborhoods in Winchester--Hampton Manor! Conveniently located to everything: downtown, the Bypass, Interstate 64, 627 going to Interstate 75 going to Lexington or Richmond, 60 going to Lexington. Master bath and laundry closet added on in 2008. New roof in 2017. New water heater for the master bath and laundry September 16, 2025. There is a tankless water heater in garage which serves the rest of the house--kitchen, 1 full bath and 1 half bath. Kitchen drawers slide out and back. The fireplace is a see through between the living room and dining room. The sellers have never used it. Several other updates were done approximately 5 years ago. Flooring in kitchen, 1 full bath and 1 half bath replaced. Several new windows will be installed in next 3 or 4 weeks. House is across the street from the Winchester Country Club. You can enjoy the screened-in porch and the deck out back in private,

35 Mockingbird Valley Rd, Winchester

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