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$285,000
3 Beds ⋅ 2 Baths ⋅ 26019908 MLS
Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded views—perfect for relaxing or entertaining\. The semi\-finished walkout basement provides additional living space and a rear\-entry garage for added convenience\. Don't miss this opportunity to own a home that combines comfort, privacy, and a great location\!

108 Milwood Dr, Winchester
$785,000
5 Beds ⋅ 3 Baths ⋅ 26019610 MLS
Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three additional bedrooms, and another full bath. The primary suite is a true retreat with exposed wood beams, a sitting area, tiled shower, and marble vanity. Upstairs you'll find a fifth bedroom, while the fully finished basement adds even more flexible living space with a second living area, kitchenette, bonus rooms, half bath, and radon mitigation system already in place. Throughout the home you'll find beautiful shiplap accents and a mix of hardwood, tile, vinyl, and carpet flooring. Step outside to enjoy the covered patio, pergola, fire pit, swing, above-ground pool with deck, and playset, all perfect for entertaining or relaxing. The attached two-car garage is complemented by an additional detached garage with its own upstairs space and separate electric meter, offering endless possibilities for a workshop, storage, or future expansion. Thoughtfully updated over the years and offering the perfect mix of space, comfort, and country charm, this property is ready to welcome you home.

217 Wades Mill Rd, Winchester
$229,000
3 Beds ⋅ 2 Baths ⋅ 26019206 MLS
Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities. Don't miss the opportunity to make this delightful property your new home!

13 Long Ave, Winchester
$374,900
3 Beds ⋅ 2 Baths ⋅ 26016576 MLS
Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of living space, this 3-bedroom, 2-bath home blends timeless character with thoughtful updates. The main level features a spacious family room with a cozy fireplace, custom cabinetry and new granite countertops in the kitchen, and a versatile dining room that can also serve as a home office. Don't miss the relaxing all-seasons room overlooking the professionally leveled and graded yard—perfect for morning coffee or evening gatherings. Upstairs, the private primary suite offers a generous bedroom, full bath, and three walk-in closets. An unfinished basement provides abundant storage or the opportunity to expand your living space. Conveniently located just minutes from historic downtown Winchester, the bypass, shopping, dining, and I-64, this move-in ready home offers comfort, charm, and exceptional convenience.

15 Moundale Ave, Winchester
$499,000
5 Beds ⋅ 3 Baths ⋅ 26013305 MLS
First time on the market! This one-owner, all brick home offers 5 bedrooms, 2.5 baths, and sits on a spacious 0.6-acre lot. The well-designed floor plan provides plenty of room for family living and entertaining. The finished basement features a dedicated office and recreation room, offering flexible space for work, hobbies, or play. Enjoy the quality and durability of brick construction, a large yard, and the pride of ownership that shines throughout this well-maintained property. Don't miss this rare opportunity to make this exceptional home your own!

182 Chardonnay Ct, Winchester
$312,000
3 Beds ⋅ 3 Baths ⋅ 26008021 MLS
Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full bath and nice walk in closet. Picture hosting your social events on the expansive two-level decks located at the back of your new home. If that is not enough this home is perfectly located within waking distance to Kroger & Walmart, shopping and dining. Come be the first to see this one or your likely to regret it. This home has never flooded but as of 2025 it does require flood insurance. The current owner has the flood insuance through ( The Hartford ) insurance company at a cost of $100 a month. Owner is offering to pay $1200 for the new owners first year of flood insurance.

200 Dubuy Dr, Winchester
$115,000
3 Beds ⋅ 1 Baths ⋅ 26014899 MLS
Welcome to 25 Oliver Street, an affordable 3 bedroom, 1 bathroom ranch home in Winchester offering a practical blend of charm and investment potential. With 900 sq ft of first-floor living space, this home features a comfortable layout with vinyl flooring and a manageable single-level design that works well for homeowners, renters, or buyers looking to build equity. The unfinished basement with interior and exterior access adds valuable storage, utility space, and future potential. With under-utilized *R-4 Zoning*, an intelligent investor may uncover additional return on investment. The front porch and rear deck create simple outdoor spaces to relax and enjoy. This property offers the everyday essentials buyers look for at an approachable price point. Whether you are searching for a personal home, a rental property, or your next value-add opportunity in Winchester, this Oliver Street home is worth a closer look.

25 Oliver St, Winchester
$2,999,000
6 Beds ⋅ 5 Baths ⋅ 25507353 MLS
Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter.

3049 Ironworks Rd, Winchester
$499,900
4 Beds ⋅ 3 Baths ⋅ 26010312 MLS
One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

16 Manor Dr, Winchester
$189,900
2 Beds ⋅ 1 Baths ⋅ 25506124 MLS
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 bedroom.

605 College St, Winchester
$413,000
3 Beds ⋅ 3 Baths ⋅ 26009517 MLS
Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a wooded area. The 2 car garage is right off the kitchen allowing for easy accessibility to bring your groceries in. The primary is on the first floor and has an en-suite with a separate sink area from the shower and toilet. There are two other bedrooms and another full bath on the first floor for guests. In the basement you will find the family room and another gas fireplace. There is enough room to have one corner of the basement be an office if needed. You will also find another half bath and utility room on the lower level. The back side of the basement has a large unfinished area with tons of possibilities. The basement family room has walk up/walk out access to the back yard patio where you will find an above ground pool, greenhouse, play set and trampoline (all can be conveyed if needed).

20 Edgewood Dr, Winchester
$445,500
3 Beds ⋅ 3 Baths ⋅ 26009944 MLS
This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

42 Mockingbird Valley Rd, Winchester
$294,900
3 Beds ⋅ 2 Baths ⋅ 26011009 MLS
This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and potential! On a large corner lot in a cute, established neighborhood, this property features a spacious detached garage ideal for storage, hobbies, or workshop space. Inside, you'll find a functional layout with plenty of natural light and room to make it your own. The large partially unfinished basement provides endless possibilities for additional living space, recreation, storage, or future expansion. Step outside to enjoy the oversized covered patio — the perfect spot for relaxing, entertaining, or enjoying quiet evenings outdoors. Conveniently located with a welcoming neighborhood feel, this home is full of opportunity and ready for its next owner!

147 Sunset Hts, Winchester
$284,900
4 Beds ⋅ 2 Baths ⋅ 26009371 MLS
Conveniently located, this charming well kept home features a functional floor plan offering space that can be tailored for those who love to entertain or the growing family. On the main level you'll find the living room, an eat in kitchen, 3 bedrooms and a full bathroom. Off of the kitchen is a large deck that's perfect for get togethers with family or friends. Downstairs has a second living area/flex space as well as an additional bedroom and bathroom. The fenced in backyard features plenty of shade and a 12'x24' storage shed. Don't miss out on this great move in ready home! Seller is offering $3,000 BUYER CREDIT!

618 Westmeade Dr, Winchester
$635,000
3 Beds ⋅ 3 Baths ⋅ 26010445 MLS
Experience the perfect balance of peaceful country living and modern comfort at 5865 Van Meter Road. Situated on 5.05 scenic acres with breathtaking farmland views, this spacious ranch-style home offers more than 2,700 square feet of thoughtfully designed living space with privacy, versatility, and charm throughout. A brand-new roof installed in May 2026 adds even more value and peace of mind. Inside, you'll find beautiful hardwood and tile flooring, a warm and inviting living room with fireplace, and an updated kitchen featuring abundant cabinetry, breakfast bar seating, and a cozy eat-in dining area. The spacious primary suite serves as a relaxing retreat with heated bathroom floors, towel warmer, and custom closet organization. The partially finished walk-out and walk-up basement provides flexible additional living space perfect for a recreation room, home office, guest quarters, or entertaining area. A wood-burning fireplace adds character and comfort, while the gas furnace with built-in humidifier enhances year-round efficiency and convenience. Outdoor amenities make this property truly stand out. Enjoy the large double rear deck overlooking rolling farmland, a massive 44x30 workshop/outbuilding, partial fencing, and a 50-amp RV hookup. Whether you need room for hobbies, equipment, animals, or simply want space to enjoy the outdoors, this property offers endless possibilities. The newly constructed pond is approximately 90% owned by the property owner and 10% shared with the neighboring property. Conveniently located with quick access to I-64 and I-75, this exceptional property delivers the serenity of rural Kentucky living while remaining only 15 minutes from Hamburg and approximately 25 minutes from UK Hospital. Acreage, updates, functionality, and stunning views come together in this rare opportunity.

5865 Van Meter Rd, Winchester
$247,500
3 Beds ⋅ 2 Baths ⋅ 26013350 MLS
"Motivated sellers—bring your offers!" Step into this charming 3-bedroom, 2-bath home that's full of character and timeless appeal. From the beautiful hardwood floors to the inviting living spaces, this older home offers warmth and personality you simply don't find in newer construction. The spacious living room provides plenty of room to relax or entertain, while the separate dining room is perfect for family meals and special gatherings. The large kitchen offers abundant space for cooking, storage, and everyday living. Outside, you'll enjoy a fully fenced backyard that's ideal for children, pets, gardening, or outdoor entertaining. Sip your morning coffee on the welcoming covered front porch or unwind on the back deck overlooking the private yard. This home offers the perfect combination of classic charm, generous living space, and inviting outdoor areas. Don't miss this wonderful opportunity to make this charming home your own!

377 Crescent Ave, Winchester
$539,500
4 Beds ⋅ 5 Baths ⋅ 26013378 MLS
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 and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the tone for the elegance that flows throughout the home. The formal living room exudes Southern charm, featuring intricate moldings, and large windows that bathe the space in natural light. The formal dining room is perfect for hosting memorable gatherings, with ample space for entertaining in style. Designed for both beauty and function, this home seamlessly blends historic inspiration with modern amenities, creating a warm and inviting atmosphere. Whether you're enjoying a quiet evening on the spacious screened in porch or hosting lavish celebrations, this extraordinary estate is a true embodiment of Southern grace and hospitality.

600 Boone Ave, Winchester
$310,000
4 Beds ⋅ 2 Baths ⋅ 26014681 MLS
Welcome home to this well-maintained, one-owner split-level offering space, comfort, and endless possibilities! Featuring 4 bedrooms and 2 full baths, this home provides room for everyone. Enjoy both a spacious living room and cozy family room wih a fireplace, perfect for relaxing or entertaining. The functional floor plan offers flexibility for today's lifestyle. New carpet and fresh paint throughout the house! Don't miss this opportunity to make this cherished home your own!

872 Stratton Ln, Winchester