Commonwealthrepro.com Search Results

Enjoy peaceful country living on 9.09 acres, just off Boonesboro Road with convenient access to both Winchester and Richmond! Surrounded by beautiful wooded scenery, this spacious 5-bedroom, 2.5-bath home offers plenty of privacy and room to spread out. The main level features hardwood flooring, a welcoming living room, a kitchen with granite countertops and stainless steel appliances, a dining area, and access to the screened-in back porch. You'll also find three bedrooms on the main level, including the primary suite, while upstairs offers two generously sized additional bedrooms and a half bath. Step outside to the covered, screened-in back porch, updated in 2025, where you can relax and enjoy the peaceful wooded surroundings. The finished walkout basement provides even more flexible living space, perfect for a second living area, recreation room, or entertaining. The property also features a detached garage, carport, and a mix of cleared and wooded acreage. The sellers have enjoyed hunting on the property, with deer frequently captured on their trail cameras (see photos)! Major improvements include a new roof in 2021, HVAC units in 2022, remodeled bathrooms, added insulation, and new carpet in the primary suite and on steps. With its easy access to town, this property offers the space and privacy of rural living without sacrificing convenience!

5 Beds ⋅ 3 Baths ⋅ 26030232 MLS

Enjoy peaceful country living on 9.09 acres, just off Boonesboro Road with convenient access to both Winchester and Richmond! Surrounded by beautiful wooded scenery, this spacious 5-bedroom, 2.5-bath home offers plenty of privacy and room to spread out. The main level features hardwood flooring, a welcoming living room, a kitchen with granite countertops and stainless steel appliances, a dining area, and access to the screened-in back porch. You'll also find three bedrooms on the main level, including the primary suite, while upstairs offers two generously sized additional bedrooms and a half bath. Step outside to the covered, screened-in back porch, updated in 2025, where you can relax and enjoy the peaceful wooded surroundings. The finished walkout basement provides even more flexible living space, perfect for a second living area, recreation room, or entertaining. The property also features a detached garage, carport, and a mix of cleared and wooded acreage. The sellers have enjoyed hunting on the property, with deer frequently captured on their trail cameras (see photos)! Major improvements include a new roof in 2021, HVAC units in 2022, remodeled bathrooms, added insulation, and new carpet in the primary suite and on steps. With its easy access to town, this property offers the space and privacy of rural living without sacrificing convenience!

843 Ford Hampton Rd, Winchester

$209,000

Really Nice all Brick 3 bedroom, 1 Bath Ranch with large garage and a fully enclosed covered back patio in desireable Colonial Valley Neighborhood. Low Electric bills, HVAC 2 years old, Water Heater 3 years. Most comparable homes in this neighborhood don't have a garage or enclosed porch. Picture of Range and refrigerator are for illustration only. Seller will give a $1,000 allowance for appliances

3 Beds ⋅ 1 Baths ⋅ 26029492 MLS

Really Nice all Brick 3 bedroom, 1 Bath Ranch with large garage and a fully enclosed covered back patio in desireable Colonial Valley Neighborhood. Low Electric bills, HVAC 2 years old, Water Heater 3 years. Most comparable homes in this neighborhood don't have a garage or enclosed porch. Picture of Range and refrigerator are for illustration only. Seller will give a $1,000 allowance for appliances

117 Colonial Park Dr, Winchester

$325,000

Distinctive character, generous space, and a convenient location near downtown Winchester! This five-bedroom, three-bath brick home offers room to spread out, with flexibility for guest rooms, a home office, or hobbies. Eye-catching architectural details and an inviting front porch give the home memorable curb appeal. With downtown shops and dining nearby, 25 W. Hickman Street combines the appeal of an established neighborhood with everyday convenience. Schedule your private showing and picture your next chapter here! Property can be used as residential or office space.

5 Beds ⋅ 3 Baths ⋅ 26028567 MLS

Distinctive character, generous space, and a convenient location near downtown Winchester! This five-bedroom, three-bath brick home offers room to spread out, with flexibility for guest rooms, a home office, or hobbies. Eye-catching architectural details and an inviting front porch give the home memorable curb appeal. With downtown shops and dining nearby, 25 W. Hickman Street combines the appeal of an established neighborhood with everyday convenience. Schedule your private showing and picture your next chapter here! Property can be used as residential or office space.

25 W Hickman St, Winchester

$390,000

7353 Ironworks Road and 3015 Pilot View Road are deeded separate but being sold together. 7353 Ironworks includes the house and barn and 3.348 acres. 3015 Pilot View is the adjacent lot and has 3.38 acres. Total acreage is 6.728. There are 2 bedrooms upstairs that need cosmetic work. The historic barn is large, has electric and needs some repair. There is plenty of space to build your dream home. Plenty of road frontage on Ironworks and Pilot View. The lots are mostly level, some sloping and mainly cleared. Lots of things to like about this property! Transform this wonderful old farmhouse or plenty of room to build your dream home. Selling as is, Inspections welcome.

4 Beds ⋅ 1 Baths ⋅ 26025300 MLS

7353 Ironworks Road and 3015 Pilot View Road are deeded separate but being sold together. 7353 Ironworks includes the house and barn and 3.348 acres. 3015 Pilot View is the adjacent lot and has 3.38 acres. Total acreage is 6.728. There are 2 bedrooms upstairs that need cosmetic work. The historic barn is large, has electric and needs some repair. There is plenty of space to build your dream home. Plenty of road frontage on Ironworks and Pilot View. The lots are mostly level, some sloping and mainly cleared. Lots of things to like about this property! Transform this wonderful old farmhouse or plenty of room to build your dream home. Selling as is, Inspections welcome.

7353 Ironworks Rd, Winchester

$160,000

Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer to verify all information including schools

3 Beds ⋅ 1 Baths ⋅ 26022678 MLS

Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer to verify all information including schools

24 Spring St, Winchester

$265,000

Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and a cozy den perfect for movie nights or a home office. Outside, unwind in the private screened-in patio attached to an impressive, oversized barn-style two-car garage, which features massive bonus storage space above. Don't miss your chance to own a piece of Winchester charm—schedule your tour today and make Kittison Drive your next chapter!

3 Beds ⋅ 2 Baths ⋅ 26022208 MLS

Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and a cozy den perfect for movie nights or a home office. Outside, unwind in the private screened-in patio attached to an impressive, oversized barn-style two-car garage, which features massive bonus storage space above. Don't miss your chance to own a piece of Winchester charm—schedule your tour today and make Kittison Drive your next chapter!

15 Kittison Dr, Winchester

$199,900

606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside, you'll find a fenced backyard, detached one-car garage, storage shed, and welcoming front porch. The seller reports the roof and HVAC are both under six years old. A wonderful home with charm, practical space, and a great Winchester location!

2 Beds ⋅ 1 Baths ⋅ 26021605 MLS

606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside, you'll find a fenced backyard, detached one-car garage, storage shed, and welcoming front porch. The seller reports the roof and HVAC are both under six years old. A wonderful home with charm, practical space, and a great Winchester location!

606 College St, Winchester

$785,000

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.

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

$1,595,000

NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3 Beds ⋅ 3 Baths ⋅ 26011538 MLS

NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3166 Colby Rd, Winchester

$490,000

Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

5 Beds ⋅ 3 Baths ⋅ 26007022 MLS

Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

110 White Conkwright Rd, Winchester

$419,900

Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your own peaceful getaway Whether you're looking for steady income, a smart investment, or a quiet escape, this riverfront property delivers.

4 Beds ⋅ 3 Baths ⋅ 26004512 MLS

Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your own peaceful getaway Whether you're looking for steady income, a smart investment, or a quiet escape, this riverfront property delivers.

240 Athens Boonesboro Rd, Winchester

$255,000

Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a private bath. Upstairs you'll find two additional generously sized bedrooms along with a convenient half bath. Enjoy relaxing mornings on the covered front porch made for rocking chairs or unwind on the covered rear porch overlooking the backyard. Additional features include two carports, storage building, rear drive access, fresh paint, some new flooring, central heat and air, and much more! Don't miss your opportunity to own this move-in ready home with space, updates, and charm throughout. Schedule your showing today! This is a Fannie Mae HomePath property.

3 Beds ⋅ 3 Baths ⋅ 26011097 MLS

Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a private bath. Upstairs you'll find two additional generously sized bedrooms along with a convenient half bath. Enjoy relaxing mornings on the covered front porch made for rocking chairs or unwind on the covered rear porch overlooking the backyard. Additional features include two carports, storage building, rear drive access, fresh paint, some new flooring, central heat and air, and much more! Don't miss your opportunity to own this move-in ready home with space, updates, and charm throughout. Schedule your showing today! This is a Fannie Mae HomePath property.

209 Boone Ave, Winchester

How much is your home worth?

How much is your home worth?