Refine Search
Map
Sort by
$240,000
3 Beds ⋅ 2 Baths ⋅ 24009950 MLS ⋅ 1,265 SqFt. ⋅ ACTIVE Status

216 Bartram Court, Winchester
$290,000
3 Beds ⋅ 2 Baths ⋅ 24009682 MLS ⋅ 1,475 SqFt. ⋅ ACTIVE Status
Clean, Cozy, Low Maintenance, One Level, Great Neighborhood! What more could you ask for? This one owner brick home has been very well maintained! Nice sized living room with a gas log fireplace for those cool mornings! Located in a sought-after location close to the Winchester Country Club and downtown offering easy access to everything! Make your appointment to see this one before it's gone!

305 Gallahadion Court, Winchester
$65,000
24009813 MLS ⋅ ACTIVE Status
Escape the hustle and bustle of city life and immerse yourself in the natural beauty of this five-acre wooded lot. Towering trees and lush vegetation offer both privacy and a rich habitat for local wildlife. The land is teeming with mature timber, adding both aesthetic and practical value. Whether you envision building your dream home, a rustic cabin, or simply want a secluded spot for weekend getaways, this property is for you. For outdoor enthusiasts, this land is a haven for recreational activities. Enjoy the tranquility of camping under the stars, explore the woods on nature hikes, or indulge in hunting in your own backyard. Located just minutes from the Mountain Parkway for easy access. Utilities are available at the road. Road Dept has been out to approve a driveway location and sellers will be installing a culvert.

4450 Trapp-Goffs Corner Road, Winchester
$315,000
4 Beds ⋅ 2 Baths ⋅ 24009807 MLS ⋅ 2,015 SqFt. ⋅ ACTIVE Status
**OPEN HOUSE This Sunday 2-4PM** Gorgeous 4 Bedroom 2 Bath Home With Beautiful Updates Throughout! The main level features a huge family room that flows into the updated Kitchen... grey cabinets, granite tops, tile backsplash, and stainless appliances. The main level also has 2 huge bedrooms and a full bath with tile surround. The upper level features 2 additional large bedrooms and a 2nd full bath. The backyard Is private, and really good size, ready For your backyard BBQ. Play-set & trampoline convey. Call Today For Your Private Showing Before It Is Too Late!

3479 Stamper Drive, Winchester
$299,900
6 Beds ⋅ 4 Baths ⋅ 24009808 MLS ⋅ ACTIVE Status
Looking for a ''House Hack''? Well, opportunity awaits...This four-plex is conveniently located in the heart of downtown Winchester and the options are endless. There is one vacant unit that would be ideal for an owner/occupant. Upstairs features two units, both are two bed, one bath units. Downstairs units are each one bed, one bath. All occupied units have been updated. There is a ton of potential for value adds. This property can be packaged with 221 S. Highland (tr-plex). Call today with questions.

127 - 129 South Highland Street, Winchester
$269,900
3 Beds ⋅ 2 Baths ⋅ 24009506 MLS ⋅ 2,078 SqFt. ⋅ ACTIVE Status
Enjoy this wonderful home in the heart of Winchester on a quiet street with Legacy Park literally steps away! This home is great for entertaining as it has plenty of space. Three large, open rooms have plenty of diversity to allow for arranging needs and preferences. The front bedroom would also make the perfect home office, and the sunroom is AMAZING! Step out onto the new deck and enjoy this wonderful back yard with or without the above ground pool-Buyer's choice! The back deck includes a wheelchair ramp and the back doorways are wheelchair accessible. Several upgrades the Seller has made for the next owner to enjoy are new windows with a transferrable warranty, Nest thermostat, new flooring in bathrooms, new gutters and guards, kitchen, pantry and both back rooms, new fridge and granite countertops! The air ducts have also recently been cleaned and there is an air filtration system as well. Schedule your appointment today!

9 Bon Haven Avenue, Winchester
$825,000
24009769 MLS ⋅ ACTIVE Status
Excellent location on the By-Pass in Winchester. Large office building that is one unit but could be converted back to 3 units. 11 private offices on main floor with 2 conference rooms. Upstairs has large rooms as well as private offices.

920 Bypass Road, Winchester
$175,000
3 Beds ⋅ 2 Baths ⋅ 24009765 MLS ⋅ 1,280 SqFt. ⋅ ACTIVE Status
NEW LISTING! Beautiful 6.5 acre property that's mostly wooded would be great for recreational use! Storage barn for all your recreational vehicles as well as a small storage shed. Perfect spot in back for bonfire and seller is leaving the picnic table. The manufactured home could be primary residence or hunter's retreat. Three-bedroom, 2-bath split bedroom floor plan. The primary bedroom has its own bath. Kitchen includes range, dishwasher and refrigerator. The above-ground pool has a newer liner and new pump and works great! It also has a covered front and back deck perfect for having your morning coffee and listening to the sounds of nature. Selling AS-IS but inspections are welcome!

3604 Pine Ridge Road, Winchester
$175,000
3 Beds ⋅ 2 Baths ⋅ 24009743 MLS ⋅ 1,280 SqFt. ⋅ ACTIVE Status
NEW LISTING! Beautiful 6.5 acre property that's mostly wooded would be great for recreational use! Storage barn for all your recreational vehicles as well as a small storage shed. Perfect spot in back for bonfire and seller is leaving the picnic table. The manufactured home could be primary residence or hunter's retreat. Three-bedroom, 2-bath split bedroom floor plan. The primary bedroom has its own bath. Kitchen includes range, dishwasher and refrigerator. The above-ground pool has a newer liner and new pump and works great! It also has a covered front and back deck perfect for having your morning coffee and listening to the sounds of nature. Selling AS-IS but inspections are welcome!

3604 Pine Ridge Road, Winchester
$25,000
24009694 MLS ⋅ ACTIVE Status
Build to suit on this lot located in the Bradley Place subdivision close to restaurants, shopping, and much more.

215 Connie Lane, Winchester
$3,500,000
8 Beds ⋅ 8 Baths ⋅ 24009605 MLS ⋅ 12,702 SqFt. ⋅ ACTIVE Status
Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot residence offers eight bedrooms and 7.5 bathrooms. Classical elements, from the refined columns to the oversized fanlight, add gravitas. Immaculately maintained, the home's warm interiors and fine millwork provide a welcoming backdrop for decor. Designer details include stylish wallpapers, tray ceilings, marble accents, & elegant fireplaces. A sunny walk-out lower level provides additional living space including a full kitchen and second laundry room. Ample storage including well-designed closets are found throughout. An attached 4-car garage accommodates vehicles. Outside, a workshop adds space for leisure and hobbies. Mature trees provide a pleasing backdrop for the large in-ground pool and outdoor living spaces. A barn and verdant fields also allow for equestrian pursuits.

4664 Lexington Road, Winchester
$3,500,000
8 Beds ⋅ 8 Baths ⋅ 24009597 MLS ⋅ 12,702 SqFt. ⋅ ACTIVE Status
Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot residence offers eight bedrooms and 7.5 bathrooms. Classical elements, from the refined columns to the oversized fanlight, add gravitas. Immaculately maintained, the home's warm interiors and fine millwork provide a welcoming backdrop for decor. Designer details include stylish wallpapers, tray ceilings, marble accents, & elegant fireplaces. A sunny walk-out lower level provides additional living space including a full kitchen and second laundry room. Ample storage including well-designed closets are found throughout. An attached 4-car garage accommodates vehicles. Outside, a workshop adds space for leisure and hobbies. Mature trees provide a pleasing backdrop for the large in-ground pool and outdoor living spaces. A barn and verdant fields also allow for equestrian pursuits.

4664 Lexington Road, Winchester
$175,000
3 Beds ⋅ 2 Baths ⋅ 24009482 MLS ⋅ 1,696 SqFt. ⋅ ACTIVE Status
Welcome to this 2-story older home, just minutes to downtown! With 3 bedrooms and 2 bathrooms, this residence is a perfect blend of vintage charm and modern convenience and is awaiting your touches! Upon entering, you are greeted by a spacious entrance foyer that sets the tone for the character found throughout the home. The main level features the primary bedroom while upstairs you will find two additional bedrooms and a small room that could be a home office, a craft room, or even a walk-in closet! The eat-in kitchen is the heart of the home and leads to a covered back porch, a perfect spot for your grill. Out front, a sizable front porch spans the width of the house, providing the perfect spot to relax. This home's solid bones and location make it a wonderful opportunity and a blank slate for those looking to customize and create their dream home on a budget! There are many restaurants, boutiques and more downtown, the public library and two local parks are just a few blocks away and you are just minutes from the interstate for commuting. The building next down is now privately owned and no longer a church. Will not pass FHA or VA.

150 West Broadway Street, Winchester
$375,000
2 Beds ⋅ 1 Baths ⋅ 24009464 MLS ⋅ 1,116 SqFt. ⋅ ACTIVE Status
Embrace the potential of this 5-acre gem near Winchester & Hamburg, KY. This fixer-upper boasts 2 beds, 1 bath, and scenic farm views on flat land. Enjoy a long driveway and a detached 2-car garage. Ideal for a smaller homestead! Close to amenities but secluded enough for privacy. Get on the schedule to see this one today!

1363 Clintonville Road, Winchester
$249,900
3 Beds ⋅ 3 Baths ⋅ 24009417 MLS ⋅ 1,648 SqFt. ⋅ ACTIVE Status
Charming Craftsman-Style Home Featuring 3 Bedrooms, 2 Full and 1 Half Baths, and 1 Car Garage. The Main Floor of this Home Features and Open Concept Family Room, Kitchen & Dining, a Half Bath, Stainless Steel Applicances, & LVP Flooring. Head Upstairs to the Large Primary Suite with Full Bath & Walk-In Closet. 2 Additional Bedrooms, a 2nd Full Bath, Separate Laundry Room, & New Carpeting Complete the Upstairs. Move-In Ready.

309 Buffalo Trace, Winchester
$499,900
24009145 MLS ⋅ 5,780 SqFt. ⋅ ACTIVE Status
This multi-use building is currently used as an Auction House, Store and Restaurant. It is all one level, almost 5800 sq ft with 2400 sq ft of bonus storage space. The interior has LED lighting with Natural Gas, KU Electric, and high-speed internet. The exterior lot has 12 parking spots as well as 9 additional public parking spots in front of the building. Currently zoned B-2 and located just off Main Street. The kitchen equipment can be purchased from the owner. Schedule your showing today!

26 East Broadway Street, Winchester
$255,000
4 Beds ⋅ 3 Baths ⋅ 24009113 MLS ⋅ 1,618 SqFt. ⋅ ACTIVE Status
Escape the hustle and bustle of city life without sacrificing convenience - this stunning 4-bedroom home nestled on a serene dead-end street surrounded by lush greenery is the perfect sanctuary for your family. While being just moments away from the interstate, and dining hotspots. The spacious open kitchen and dining area seamlessly flow into the living room, offering a seamless blend of comfort and style. Plus, the first floor features a convenient laundry area and a half bath. Upstairs, retreat to your cozy bedrooms, each boasting ample closet space for all your storage needs. Experience the best of both worlds with this idyllic home - urban convenience meets suburban peace.

510 Mallory Lane, Winchester
$335,000
3 Beds ⋅ 2 Baths ⋅ 24008913 MLS ⋅ 1,680 SqFt. ⋅ ACTIVE Status
Are you looking for a place that has it all? Then you have found it. This property has an abundance of extras! From the serene 14.7 acres, woods, cleared walking trails, wildlife, places to ride your recreational vehicles or just relax in the peaceful surroundings! Enjoy the beautiful landscaping, sunsets and views from a spacious front porch overlooking a small pond. Manufactured home on a permanent foundation. 3-bedroom, two bath, eat-in kitchen, oversized 2-car garage, and paved driveway with lots of space for parking. Plus a 30' x 40' Pole Building workshop with electric. Small office trailer that could be perfect for guests or a home office, internet available. This property is a must see to appreciate. Don't miss this rare opportunity! Call today for your private showing. By appointment only.

2296 Trapp Goff Corner, Winchester
$279,900
5 Beds ⋅ 3 Baths ⋅ 24008911 MLS ⋅ ACTIVE Status
Calling all INVESTORS. You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. This property can be purchased as a package deal with another S. Highland property (4plex). Please call with any questions, please do not disturb the tenants!

221 South Highland Street, Winchester
$565,000
4 Beds ⋅ 4 Baths ⋅ 24008844 MLS ⋅ 5,440 SqFt. ⋅ ACTIVE Status
Welcome to 281 Rose Dr. located in the prestigious Mallard Place subdivision. This home features 4 bedrooms and 4 full bathrooms across 5,440 sq ft of total living space, perfectly designed for both grand entertaining and private comfort. The residence includes multiple walk-in closets, ensuring ample storage and organization. The second floor is pre-wired for a media room, creating an ideal space for a home theater or entertainment hub. Situated on a prime level corner lot, the home boasts over 1,500 sq ft of garage space alongside a vast driveway suitable for multiple vehicles. Relish the great outdoors from the comfort of your large patio or the screened-in deck, both perfect for relaxing or hosting events. With its luxurious amenities and desirable location, this home is a true gem waiting to be yours!

281 Rose Drive, Winchester
$599,900
5 Beds ⋅ 4 Baths ⋅ 24008612 MLS ⋅ 4,515 SqFt. ⋅ ACTIVE Status
This meticulously crafted 5-bedroom home boasts exquisite trim and finishes throughout. The main level features a grand formal dining room leading to a light-filled family room with a dramatic vaulted coffered ceiling. Perfect for gatherings, the open-concept kitchen allows you to cook and socialize seamlessly.Upstairs, a second primary suite awaits, complete with a luxurious bathroom and a massive walk-in closet. The expansive basement offers additional living space with 3 bedrooms (2 non-compliant), a full bath, laundry area, and unfinished storage.A brand new 30x50 barn is perfect for all of your hobby and storage needs & don't worry, if you're caught in a snow storm or power outage this home is equipped with a wood burnin stove and propane in addition to electric heat. Enjoy outdoor entertaining on the covered deck overlooking your 2.3-acre property, conveniently located near I-64. Bonus: a brand new roof will be installed before closing!

6595 Mt Sterling Road, Winchester
$109,000
24008591 MLS ⋅ ACTIVE Status
Prime building lot - 4.15 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on your lot.

2058 Athens Boonesboro Road, Winchester
$199,000
4 Beds ⋅ 2 Baths ⋅ 24008590 MLS ⋅ 1,344 SqFt. ⋅ ACTIVE Status
Nice 4 bedroom, 2 bath home located on a quiet cul de sac close to Winchester bypass and downtown Winchester. This is your chance to have a piece of country living right in town. Home is being sold as is.

3617 Stamper Drive, Winchester
$109,000
24008576 MLS ⋅ ACTIVE Status
Prime building lot - 4 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on your lot.

2010 Athens Boonesboro Road, Winchester
$379,900
4 Beds ⋅ 2 Baths ⋅ 24008452 MLS ⋅ 2,413 SqFt. ⋅ ACTIVE Status
Charming all-brick ranch featuring 4 bedrooms and 2 full bathrooms with a delightful all-season room overlooking beautiful flower gardens on a spacious, flat lot. Located in Stoneybrook Subdivision! Make an appointment today, for your private viewing.

406 Lynnway Drive, Winchester
$650,000
24003079 MLS ⋅ ACTIVE Status
This money making car wash has three drive in bays and one automatic wash. Included with the sale is a vibrant oil change business which occupies two bays.

126 Shoppers Drive, Winchester
$150,000
24008145 MLS ⋅ ACTIVE Status
Looking for that perfect spot to build your dream home? These 2 beautiful lots, a 2.336 acre parcel (Lot 5) and a 1.722 acre parcel (Lot 6), might be just what you're looking for. The property is located in the new rural subdivision called Eskippakithiki Overlooks. Gorgeous views all around and plenty of room to breathe fresh air, yet you're only 8 minutes from Mountain Parkway. Lots are located 10 miles from downtown Winchester, 6 miles to Clay City, and 33 miles (36 minutes) to downtown Lexington. Gently rolling lots with electric attached and public water at the road. Lots can be purchased separately too. Why live in the city, when you have privacy with gorgeous views and the same commute time?

12591- 12651 Ironworks Road, Winchester
$75,000
24008141 MLS ⋅ ACTIVE Status
Looking for that perfect spot to build your dream home? This beautiful 1.722 acre parcel (Lot 6) might be just what you're looking for. The property is located in the new rural subdivision called Eskippakithiki Overlooks. Gorgeous views all around and plenty of room to breathe fresh air, yet you're only 8 minutes from Mountain Parkway. It's located 10 miles from downtown Winchester, 6 miles to Clay City, and 33 miles (36 minutes) to downtown Lexington. Gently rolling lot with utilities at the road, or if you're looking for a bigger lot, there's an additional 2.336 acre parcel (Lot 5) that can be purchased that adjoins this lot. That would be a combined 4.058 acres with both lots. Why live in the city, when you have privacy with gorgeous views and the same commute time?

12591 Ironworks Road, Winchester
$85,000
24008128 MLS ⋅ ACTIVE Status
Looking for that perfect spot to build your dream home? This beautiful 2.336 acre parcel (Lot 5) might be just what you're looking for. The property is located in the new rural subdivision called Eskippakithiki Overlooks. Gorgeous views all around and plenty of room to breathe fresh air, yet you're only 8 minutes from Mountain Parkway. It's located 10 miles from downtown Winchester, 6 miles to Clay City, and 33 miles (36 minutes) to downtown Lexington. Gently rolling lot with utilities at the road, or if you're looking for a bigger lot, there's an additional 1.722 acre parcel (Lot 6) that can be purchased that adjoins this lot. Why live in the city, when you have privacy with gorgeous views and the same commute time?

12651 Ironworks Road, Winchester
$579,500
3 Beds ⋅ 2 Baths ⋅ 24008060 MLS ⋅ 2,120 SqFt. ⋅ ACTIVE Status
Welcome to the cozy country house. There is plenty of room on this 5.72 acre mini farm that is at the end of the road. The farmhouse has three bedrooms, two full baths, three fireplaces and an in ground pool. When you come through the front door, you are greeted by a large living room with two fireplaces, one on either side. Down the hall, you will find the primary bedroom hall bath and second bedroom. At the end of the hall is the eat in kitchen with its own wood-burning fireplace. Through the kitchen you will find the back hallway, third bedroom, second full bath, and large laundry room. If you need workshops, this place features two large metal buildings. The buildings are insulated, on their own 200 amp service with separate meter and reinforced concrete floors. Building one is 50 x 60 with two overhead doors both 10 x 10 with one having a loading dock. Building two is 40 x 60 with a 12 x 12 overhead door. There is also a four car run in garage/shed that is 24 x 41. This is a must see unique property that has lots of potential.

485 Mccullough Lane, Winchester