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$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
$245,000
3 Beds ⋅ 3 Baths ⋅ 24008397 MLS ⋅ 1,575 SqFt. ⋅ ACTIVE Status
Beautiful home on a nice corner lot. You will enjoy the open kitchen/family room for entertaining or just relaxing. Kitchen has stainless steel appliances and new dishwasher. Pergola on back patio leads out to the large, fenced yard for your kids & doggo to run around in.Upstairs you will find the spacious primary with a walk-in closet, 2 more bedrooms along with 2 full bathrooms. Call today to schedule your tour!

411 Wellington Way, Winchester
$750,000
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
$25,000
24008224 MLS ⋅ ACTIVE Status
Escape the city hustle to this peaceful .59-acre rural land. Mostly clear with a few trees, it's your perfect spot for a dream home or getaway. Enjoy nature's serenity and make this tranquil haven yours. Contact me today to start your countryside adventure! 🌳🏡 ** ZONED R-1C. NO Mobile homes ro trailers allowed .

949 Muddy Creek Road, Winchester
$225,000
24008203 MLS ⋅ ACTIVE Status
Here is your opportunity to own a piece of rural Kentucky. This 9.26 acres lot has beautiful views and several locations to build a home. The back 2 +/- acres are wooded and spots to see the creek provide a breath-taking view.

2575 Grimes Mill Road, 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
$235,000
3 Beds ⋅ 2 Baths ⋅ 24007641 MLS ⋅ 1,734 SqFt. ⋅ ACTIVE Status
Stunning home in downtown Winchester, extensively and gorgeously remodeled. New (beautiful) kitchen and bathrooms, new roof, new heat pump, new windows, new flooring, new fixtures, and more! Upgrades galore, while keeping the charming character of this downtown beauty. Living room, kitchen, laundry/mud room, and three bedrooms downstairs, with large flex space upstairs. Who doesn't love a picturesque home with wrap around porch? Ideally situated on a corner lot, this wonderful home is a must see!

102 Kentucky Street, Winchester
$245,000
3 Beds ⋅ 2 Baths ⋅ 24007633 MLS ⋅ 1,422 SqFt. ⋅ ACTIVE Status
This three bedroom Ranch home has one and 1/2 baths,a large family room with a fireplace, has been updated, new flooring, new interior and exterior painting,New HVAC, new kitchen cabinets with grainte, new appliances ,It also has a large work shop.

142 Sunset Heights, Winchester
$120,000
3 Beds ⋅ 1 Baths ⋅ 24007520 MLS ⋅ 1,911 SqFt. ⋅ ACTIVE Status
Come and view this 1945 style home, sit on the front porch and enjoy a glass of tea. Inside the home, upstairs, is 2 bedrooms with plenty of storage. Downstairs is the primary bedroom, kitchen, family room, and living area. Outside is a nice size yard, and a concrete pad that once was a garage. Minutes to the interstate and close to downtown Winchester. This home does need some TLC and is being sold ''as is''. Don't delay, call today to schedule your showing.

29 Holly Avenue, Winchester
$975,000
4 Beds ⋅ 5 Baths ⋅ 24007462 MLS ⋅ 4,698 SqFt. ⋅ ACTIVE Status
One of a kind opportunity to live in history and in luxury in one of Winchester's finest offerings. This majestic home spares no detail, offering charming details throughout like hardwood floors, high ceilings, large windows, crown moldings, and fireplaces throughout. As well, the gracious lot offers expansive views and privacy with its large patio seating area and beautiful swimming pool. Ripe for entertaining or just relaxing in the privacy of this incredible estate, this home is located ideally in the south side of Winchester, conveniently located a golf cart drive across the street from Winchester Country Club and a straight shot to Lexington in under 15 minutes. This home has been painstakingly maintained and updated. See enclosed for an expansive list of improvements made.

511 Boone Avenue, Winchester
$469,900
4 Beds ⋅ 3 Baths ⋅ 24007441 MLS ⋅ 2,800 SqFt. ⋅ ACTIVE Status
This new construction house will be completed soon and ready for you to move in and call home! From the moment you step inside, you'll find stunning features including 9 foot ceilings for an open and airy feel, with hardwood floors throughout. In the kitchen will be granite countertops with white cabinets including an island with bar top seating. New stainless appliances will complete the kitchen. Upstairs will feature an open loft area with two bedrooms plus a bonus room over the garage that could also be used as a bedroom. The view from the upper floor overlooks beautiful farmland and a pond so you feel like you live in the country with all of the convenience of living in town. Out back there is a new covered deck for a wonderful place to enjoy the country view while entertaining or just relaxing on a cool summer evening. This home is not yet completely finished, so there is some opportunity for you to have some choices in the final touches.

127 Hibiscus Lane, Winchester
$469,000
3 Beds ⋅ 3 Baths ⋅ 24007336 MLS ⋅ 2,244 SqFt. ⋅ ACTIVE Status
Looking for a small farm? Check out this beautiful brick home with walk out basement located on 5.5 acres of flat land in Winchester. This is a rare jewel, you will enjoy the peace and quiet sitting on front porch drinking your coffee or relax on the large covered deck. The bonus is a nice metal unattached garage/workshop 26'X34'. Perfect little farm to have any kind of animals you desire. This beauty has hardwood floors through out main area, 3 bedrooms with carpet and 3 baths are tile. You will fall in love with the large master suite that leads to masterbath with jacuzzi tub and beautiful double vanities. A lovely home with many updates. New HVAC system, water heater, painted, all new light fixtures inside and out, kitchen subway tile backsplash, island butcherblock & tile floor. Bathrooms have new vanity tops, faucets, mirrors, ship lap, tile, shower head & hardware. You won't believe the huge laundry room. The unfinished walkout basement can be great storage area or finished for more space. This home is ready for its new owners to move in and enjoy country life at its best! Less than 30 minutes from Lexington & surrounding areas. Home has 48 hr kick out Contingency.

1159 Cabin Creek Road, Winchester
$399,900
2 Beds ⋅ 3 Baths ⋅ 24007122 MLS ⋅ 1,800 SqFt. ⋅ ACTIVE Status
This home built and loved by the Seller has many custom features Cabinets are either oak or cherry and handcrafter by the owner. The Laundry Room has a separate line to protect the septic system. House was built with yellow poplar siding and a truss roof. The roof is 3 years old. The HVAC system is 5 years old. The property is fenced on the sides and in the rear. There is a large Primary bedroom with a nice sized attached bath room and walk in closets. In addition there is a second good sized bedroom with an attached bath. There is a third room that could be used for a small bedroom or an office. Enjoy an eat in Kitchen with with refrigerator, stove, dishwasher and microwave. There is a nice sized Dining Room and a large Living Room. Mornings and evenings relax in an oak paneled sun porch with the view of cleared grass and woods. In the winter you''ll be cozy with a gas stove that can heat the entire house. The house has an attached 2 In the rear there is a 1420 SF shop. The shop was built 2011 and has different areas for different types of work to be done. Concrete drive runs to the shop and shop garage.

610 Old Ruckerville Road, Winchester
$499,900
3 Beds ⋅ 3 Baths ⋅ 24007103 MLS ⋅ 3,148 SqFt. ⋅ ACTIVE Status
This stunningly updated home is situated in the comfortable and desirable Hampton Manor subdivision right in the heart of Winchester. From the moment you pull into the driveway, you'll notice the impeccably landscaped yard and beautiful covered front porch. Take a step inside the front door and experience the refinished hardwood floors leading into spacious rooms including a gorgeous fully remodeled kitchen with granite countertops and new stainless Bosch appliances. Each of the two full bathrooms have newly updated, walk-in tile showers. Follow the steps down into the refinished basement and discover all new vinyl plank flooring in the open office and living space where you can enjoy one of the 3 ventless gas fireplaces on a cool evening. The updated sunroom also offers a lovely place to sit or entertain guests with its new windows, flooring and wooden ceiling. Outside, the improvements continue with a new covered patio beside the above ground pool where you can relax in the summer heat. Schedule your private showing today to experience all this home has to offer!

42 Mockingbird Valley Road, Winchester
$179,000
3 Beds ⋅ 2 Baths ⋅ 24007077 MLS ⋅ 1,680 SqFt. ⋅ ACTIVE Status
This newly remodeled home has a lot to offer. It has new flooring throughout, large deck on the front, and much more. Brand new heat and air is currently being installed. 3 spacious bedrooms with 2 full bathrooms. The home is just minutes from Hamburg or the Winchester Bypass. You would own the lot. Only fee is $100 a month for water and trash. Schedule a private tour before this beauty is gone.

737 Williamsburg Drive, Winchester
$99,900
2 Beds ⋅ 1 Baths ⋅ 24006600 MLS ⋅ 1,080 SqFt. ⋅ ACTIVE Status
Don't miss out on the chance to make this house your own! Whether you're seeking to add your personal touch or expanding your investment portfolio, this property offers endless possibilities! With some improvements, this 2 bedroom, 1 bathroom home is an ideal canvas for homeowners and savvy investors alike. Property is being sold AS IS. This property will not go FHA, VA, or USDA. Schedule your showing today!

129 Kentucky Street, Winchester
$125,000
24006840 MLS ⋅ ACTIVE Status
This is an unique opportunity to own a beautiful acre + building lot in Winchester! Walking distance to downtown, Country Club, College Park & library! The house seat has been graded to accommodate a daylight walk-out basement. City water, sewer, natural gas & electric are available. Currently being resurveyed to include closed alleyway. Minimal restrictions. Owner/agent.

210 Hood Avenue, Winchester
$27,500
24006777 MLS ⋅ ACTIVE Status
Situated at the end of Connie Lane is this nice building lot which is one of the largest in the subdivision. Adaptable to a variety of house plans. This will be a corner lot when Phase 3 is developed. Call today! Owner/agent

225 Connie Lane, Winchester
$175,000
24006770 MLS ⋅ ACTIVE Status
This is to be sold with 255 Connie Lane. Total acreage is 4 +/- acres. This parcel is located at the end of Dixon Way and 255 Connie Lane is located at the end of Connie Lane in Bradley Place Subdivision. Public water/sewer, electricity and cable are located at the end of each street. Property is zoned R-6 for 15 townhomes, R1E for 9 patio homes and R1D for 5 single family. Great opportunity for a small development! Owner/agent.

115 Dixon Way, Winchester
$559,900
5 Beds ⋅ 4 Baths ⋅ 24006758 MLS ⋅ 4,456 SqFt. ⋅ ACTIVE Status
This home has maximized all the space! All brick 1.5 story home on a basement in the coveted Mallard Place subdivision. Three levels of wonderful craftsmanship. The main floor has hardwood floors, vaulted ceilings, a gas fireplace, a spacious primary bedroom with an en suite bath, 2 bedrooms with a jack-n-jill bathroom, formal dining, and eat-in kitchen. The basement has an entertainment area with a bar, bonus room and storage room. The upstairs is perfect for a teen suite, or another place to relax. It has a bedroom that is a loft, bonus room/bedroom and a family room, plus more attic storage. This home is beautiful and you won't want to miss out on seeing it in person!

104 Teal Ln Lane, Winchester
$650,000
5 Beds ⋅ 4 Baths ⋅ 24005475 MLS ⋅ 4,091 SqFt. ⋅ ACTIVE Status
This is rare beauty and history located in the heart of Winchester. Embrace the essence of elegance in this beautifully appointed brick home, offering 5 bedrooms, 3 full baths and formal rooms. Main level of home boasts the primary suite as well as an additional bedroom. The large fully equipped kitchen is a delight for any chef. Home features a full walk-up basement that is unfinished with a half bath and additional laundry area. This home nestled on a spacious lot with a serene brick patio inviting relaxation. The 2 car carport situated close to home with plenty of storage.

31 Bonnie Brook Lane, Winchester
$360,000
24006648 MLS ⋅ ACTIVE Status
Create your own idyllic escape on this sprawling 93-acre property! Imagine exploring creeks, encountering diverse wildlife, or simply relaxing in the peacefulness of nature. This property boasts a charming barn, perfect for storage or hobbies, and an impressive ~4,000 feet of road frontage, providing ample space and accessibility. Whether you dream of building your forever home, establishing a working farm, or creating a nature retreat, this land offers endless possibilities. Call today for your private showing.

1410 Dry Fork Creek Road, Winchester
$799,000
4 Beds ⋅ 4 Baths ⋅ 24006529 MLS ⋅ 3,272 SqFt. ⋅ ACTIVE Status
As you meander down the winding driveway of 8 sprawling acres, a sense of tranquility washes over you-- just a short 8-minute drive from the bustling town of Winchester.The home boasts a spacious living room with fireplace, family room, eat-in kitchen, formal dining area, drop zone, two bedrooms, full bath, half bath, and master ensuite. These second floor has a wonderful size bonus room with full bathroom, and a bedroom.But perhaps the crowning jewel of this extraordinary estate lies beyond its walls--a haven of outdoor splendor awaiting your discovery. Complete with a sprawling in-ground pool and pool house with a bathroom, surrounded by meticulously manicured landscaping and stone hardscapes--a picturesque retreat where every day feels like a vacation.For the equestrian enthusiast, a charming barn awaits towards the front of the property, ready to accommodate your equine companions with multiple stables and ample storage space above. Whether you're an avid rider or simply appreciate the rustic charm of country living, this property offers endless possibilities for recreation and relaxation. Make 1995 Gay Evans your forever home!

1995 Gay Evans Road, Winchester
$289,000
4 Beds ⋅ 2 Baths ⋅ 24006544 MLS ⋅ 1,968 SqFt. ⋅ ACTIVE Status
An older home that offers the charm & character of days gone bye but has many updates of today. Step into a world of timeless charm and modern comfort with this meticulously maintained historic home. From the moment you enter, you'll be captivated by the enchanting character that fills every corner.As you cross the threshold, beautiful hardwood floors lead the way into a spacious living room and dining area, where accent columns add an elegant touch to the ambiance. Natural light pours in through large windows, illuminating the space and creating a warm, inviting atmosphere. The charm of yesterday w/updated kitchen & first floor bath. The Primary Bedroom on 1st floor has original pocket doors and a leaded glass window. Upstairs, three bedrooms offer peaceful retreats, each adorned with unique features that add to the home's allure. A sleeping porch off the primary bedroom invites you to indulge in moments of tranquility while soaking in the beauty of historic Main Street. Step outside in back to discover a covered porch with a charming brick floor, perfect for relaxing and enjoying the serene surroundings.

335 South Main Street, Winchester
$210,000
5 Beds ⋅ 4 Baths ⋅ 24006419 MLS ⋅ 2,830 SqFt. ⋅ ACTIVE Status
Investors!! Here is a chance to increase your portfolio with this Income Producing Triplex Downtown Winchester! 100% occupied generating $2,345 Monthly in rents ($28,140 annually). Units are as follows: Studio/1BA; 2B/1Ba; 2B/1.5 Ba. Tenants considered to be long term tenants. Additional side yard identified as Lot #9 included. Sold AS IS. Please do not go on property or disturb tenants.

25 Hays Street, Winchester
$220,000
5 Beds ⋅ 3 Baths ⋅ 24006420 MLS ⋅ 2,445 SqFt. ⋅ ACTIVE Status
Prime Investment Opportunity for a Cash flowing Triplex in the heart of Downtown Winchester. Three units combined produce $2,550/mo ($30,600 annually). Unit #1 has 2 bedrooms, living room, eat-in kitchen, laundry area, and a full bath. Unit #2 has 1 bedroom, living room, kitchen/dining, and a full bath. Unit #3 is a 2 bedroom unit and includes a living room, kitchen/dining, full bath, and laundry. All units are currently occupied and are considered long term tenants. Sold AS IS; Please do not go on property or disturb tenants.

130 East Broadway Street, Winchester
$385,000
3 Beds ⋅ 3 Baths ⋅ 24005987 MLS ⋅ 2,366 SqFt. ⋅ ACTIVE Status
Make your appointment today for this charming home nestled in a well-known neighborhood of Hampton Manor. It's nothing to see neighbors riding their golf carts to the nearby golf course, quiet and neighborly living. Now, to the 3 BR 2.5 BA brick ranch style home. Formal entry way going into a spacious family room with brick fireplace, dining area, eat-in kitchen. Flooring consists of hardwood, and tile. Partially finished basement has lots of potential for extra bedroom or for a perfect entertaining area with its own brick gas fireplace. As you can walk out to the plush back yard with endless possibilities, imagine taking it easy on the spring and summer nights.

20 Edgewood Drive, Winchester