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5127 Combs Ferry Rd, Winchester
$210,525
26011064 MLS
8+ Acres of Prime land available in the Heart of the Bluegrass! Whether you're looking to design your ideal homestead or simply building your custom country home with plenty of space to roam, this property offers an optimal blend of space, beauty, tranquility, and convenience. Enjoy peaceful rural living with open skies and scenic countryside views, surrounded by picturesque farms and a nearby vineyard that add to the charm of the area. The flat terrain provides some ideal options for building sites with plenty of room for gardens, livestock, barns and recreational use. Located just a short drive from Lexington, Richmond and historic downtown Winchester, you'll enjoy country living without sacrificing city amenities. Bring your plans and make it your own!

5127 Combs Ferry Rd, Winchester
59 Holiday Rd, Winchester
$208,000
3 Beds ⋅ 1 Baths ⋅ 26004165 MLS
Don't Wait - this home is priced to Sell! All one level brick ranch features 3 Bedrooms, 1-bath. Newer updates include interior paint and laminate flooring giving the home a clean modern feel. The living spaces are filled with natural light, making the home feel warm and inviting. Step out to a spacious deck and large backyard - great for entertaining or just enjoying the outdoor space. Need extra storage or a workshop? The 16 ft. X 8 ft. storage building with loft area and electricity offers just that! Additional updates include the roof being replace in 2017, a new HVAC/Gas Furnace system installed in 2021, giving you peace of mind and year-round comfort. 24 hour Notice Preferred - Schedule your appointment today.

59 Holiday Rd, Winchester
128 Abbeywood Ct, Winchester
$207,500
3 Beds ⋅ 4 Baths ⋅ 26017061 MLS
This beautifully maintained 3 bedroom, 3.5 bath townhouse offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally situated in a desirable location, this spacious home features a functional floor plan with generous living areas, well appointed bedrooms, and a bathroom for each bedroom, providing comfort and privacy for family and guests alike. Enjoy the benefits of townhouse living with less exterior maintenance, all while being just minutes from shopping, restaurants, schools, and everything Winchester has to offer. Whether you're a first time homebuyer, or searching for an investment opportunity, this move in ready home is one you won't want to miss!

128 Abbeywood Ct, Winchester
415 L E Junction Rd, Winchester
$205,000
3 Beds ⋅ 2 Baths ⋅ 26006620 MLS
Tucked away on just under 3 peaceful acres in Winchester, this charming 3-bedroom, 2-bath manufactured home on a permanent foundation offers the perfect blend of comfort and country living. Enjoy the privacy and space you've been looking for, with a beautiful creek running along the back of the property—creating a serene backdrop for relaxing evenings or outdoor entertaining. Inside, you'll find a functional layout with ample living space, while outside offers endless possibilities for gardening, recreation, or simply soaking in the natural surroundings. Whether you're looking for your first home, downsizing, or wanting a quiet retreat, this property delivers the best of rural charm with convenient access to town.

415 L E Junction Rd, Winchester
34 Hays St, Winchester
$205,000
4 Beds ⋅ 2 Baths ⋅ 26007612 MLS
This spacious 4-bedroom bungalow is tucked away in downtown Winchester in a great walkable location. Located less than a 5-minute walk to the College Park recreation center. This charming home blends timeless character with modern comfort. The kitchen and baths have been updated. The main living space has the original hardwood flooring and new flooring throughout the remaining house. The living room and kitchen flows with simplicity. There is an abundance of storage in the unfinished basement. The large back patio and fenced backyard is ready for your outdoor enjoyment.

34 Hays St, Winchester
301 Snowden Dr, Winchester
$205,000
3 Beds ⋅ 1 Baths ⋅ 26010643 MLS
Charming all-brick ranch offering timeless character and everyday functionality! Step inside to a light-filled living room featuring beautiful hardwood floors and a warm, welcoming feel throughout. This home offers three bedrooms and one full bathroom, along with an eat-in kitchen perfect for casual dining and gathering. A dedicated laundry/mud room just off the kitchen provides convenient access to the covered carport and attached storage shed. Outside, enjoy a spacious backyard with plenty of room to relax, entertain, or garden. Additional updates include a new roof installed in 2025. A wonderful opportunity for first-time buyers, downsizers, or investors alike!

301 Snowden Dr, Winchester
25 Hiawatha Trl, Winchester
$203,900
3 Beds ⋅ 1 Baths ⋅ 25502983 MLS
This cozy three-bedroom ranch on a basement is only minutes to downtown and the Veterans Memorial Bypass. This meticulously maintained home is full of natural light. The partially finished basement offers lots of potential for customization. The fenced backyard includes a deck and patio perfect for entertaining and a nice-sized storage building. Perfect for a first-time homebuyer or someone looking to downsize. Schedule your showing today!

25 Hiawatha Trl, Winchester
2366 Ironworks Rd, Winchester
$202,000
3 Beds ⋅ 2 Baths ⋅ 26005485 MLS
3-bedroom, 2-bath ranch home located in rural Clark County, offering peaceful country living with plenty of potential. This home features a versatile bonus room—ideal for a home office, playroom, or additional living space. Outside, enjoy a fully fenced yard, beautiful curb appeal, and a large storage shed for added convenience. While the home does need some TLC, it has been priced accordingly—making it a great opportunity for buyers looking to add value and make it their own.

2366 Ironworks Rd, Winchester
58 Hughes Ave, Winchester
$202,000
3 Beds ⋅ 2 Baths ⋅ 26002214 MLS
Nice remodeled 3 bedroom and 2 bath home...Ranch on a basement...2 bed 1 bath upstairs and Basement has another living area with 1 bedroom and 1 bath. Fresh paint , new lights, newer hvac and newer windows. Kitchen has been updated with granite, appliances and fresh paint....agent owner

58 Hughes Ave, Winchester
245 Ecton Rd, Winchester
$200,000
3 Beds ⋅ 1 Baths ⋅ 25504692 MLS
Will not qualify for FHA because of garage. Welcome to this fully updated home that is cozy and full of character. Featuring brand new central heating and air, electric, drywall, spray foam insulation, kitchen cabinets, water heater, and stunning hardwood floors throughout. This beautiful kitchen boasts all brand new appliances, butcher block countertops, sage green cabinets, a 30 inch farmhouse sink, and also features a 6 foot island creating the perfect space for cooking, dining, and entertaining. Featuring a very large new deck overlooking a spacious and shaded backyard, ideal for entertainment. The property includes a garage with a loft that features a tremendous amount of storage—and with some work it could become a great personal work shop or EDU.

245 Ecton Rd, Winchester
47 Watts Rd, Winchester
$200,000
3 Beds ⋅ 2 Baths ⋅ 26003845 MLS
This home is located in a quiet cul-de-sac on Watts Road in Winchester. The outside has great curb appeal and features a brick mailbox, extended blacktop driveway, 2 car garage and a fenced in backyard. Inside, there are 3 bedrooms and 2 full bathrooms with abundant living space. The downstairs has endless possibilities! Use it for a home office, 4th bedroom or a family room!

47 Watts Rd, Winchester
60 Hiawatha Trl, Winchester
$200,000
3 Beds ⋅ 1 Baths ⋅ 26006850 MLS
Updated, affordable, and ready for you! This 3-bedroom, 1-bath home offers approximately 1,300 square feet of comfortable living space with tasteful updates that make it easy to move right in. The layout provides a welcoming feel with bright living areas and an updated kitchen and bath. Downstairs you have a possible 4th bedroom or office space. Conveniently located in Winchester close to everyday amenities, this home is a great option for homeowners or investors alike. Don't miss your chance to see it!

60 Hiawatha Trl, Winchester
190 Privacy Ln, Winchester
$200,000
25501332 MLS
6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

190 Privacy Ln, Winchester
117 Buffalo Trce, Winchester
$199,900
3 Beds ⋅ 2 Baths ⋅ 25507380 MLS
Move-In Ready! 3 bedrooms, 2 bath, brand new kitchen cabinets with stylish butcher block counter tops, fresh light fixtures throughout, and durable, sleek laminate flooring. This home combines comfort and style with updates that make it truly shine. Perfect for families or first-time home buyers! Conveniently located in a great neighborhood. Owner/Agent

117 Buffalo Trce, Winchester
215 Short St, Winchester
$199,900
3 Beds ⋅ 1 Baths ⋅ 26007746 MLS
ATTENTION First Time Home Buyers! This precious brick ranch home is totally updated and ready for you to move on it and enjoy the simple life! With a wide open concept between the living, dining and kitchen areas you have options for furniture placement. The kitchen features stainless appliances including a gas range for those who love to cook! The laundry room is more like a mud room and has ample storage for over flow kitchen, drop zone, etc. All of the bedrooms and living spaces have gorgeous hardwood floors. The back yard is fully fenced with a patio space and storage building that conveys with the sale. Some mechanical updates to the house include: windows 2021, gutters 2021, gas water heater 2023, gas furnace about 8-9 years, electric air 2023, roof in 2019.

215 Short St, Winchester
265 Cunningham Ln, Winchester
$199,900
3 Beds ⋅ 2 Baths ⋅ 26010094 MLS
(back on the market due to buyers financing) Adventure is always within reach at this property! Located just 35 minutes from Red River Gorge and only 26 minutes from Natural Bridge State Resort Park, this home puts you close to some of Kentucky's most popular outdoor attractions. Spend your weekends hiking scenic trails, canoeing, kayaking, fishing, swimming, riding the sky lift, playing mini golf, enjoying lakeside picnics, or exploring the area's breathtaking mountain views. Looking for a weekend getaway close to home? Enjoy nearby camping, cozy cabins, cottages, and lodge stays that make the perfect escape for outdoor lovers, nature enthusiasts, and adventure seekers year-round. Now is your chance to snatch up this adorable home!! There's nothing sweeter than countryside views! 30 Minutes to Hamburg in Lexington & USDA eligible at 0% down! Located off the Mountain Parkway & Ironworks Rd, this property features over an acre of land, a fenced-in backyard, and a new septic tank system. Well maintained and only 2 years old, this home is the perfect opportunity to start your mini farm. (3rd bedroom not photographed, being used as storage)

265 Cunningham Ln, Winchester
313 S Burns Ave, Winchester
$197,377
3 Beds ⋅ 2 Baths ⋅ 25508192 MLS
This 3 bedroom, 2 bath home sits on a corner lot with hardwood floors and a two-car detached garage behind the home. Plus, it's walkable to downtown Winchester, the public library, and College Park. Inside, you'll find tall ceilings, a traditional living and dining room, and a unique layout that gives you options for how you use the space. The kitchen opens to the back deck, and a ramp at the back door provides easy access. A partial unfinished basement offers extra storage, and with this great in-town location, the home is priced below a recent appraisal and ready for its new owner to come in and make it their own. Inspections welcomed, selling as-is.

313 S Burns Ave, Winchester
388 Colby Ridge Blvd, Winchester
$195,000
3 Beds ⋅ 3 Baths ⋅ 25500673 MLS
Need to see inside of this one! Seller bought in May 2021. Remodeled kitchen. Removed one wall between kitchen and living room. Installed a granite bar/island and countertops. Installed all new kitchen cabinets. Installed all new stainless steel appliances (including a top-of-the-line Kitchen Aid dishwasher). Put in deep sink and garbage disposal. Pantry cabinet beside refrigerator. Spice rack beside range. Backsplash. Put in all new flooring except one bedroom. All electric KU home. Schedule your appointment today.

388 Colby Ridge Blvd, Winchester
222 Holiday Rd, Winchester
$195,000
3 Beds ⋅ 1 Baths ⋅ 24023173 MLS
Great location close t o down town Winchester, shopping, school, recreation areas, I 64 ,in beautiful Winchester,nice 3 bedroom ,1 bath , all brick home, with all appliances, including washer and dryer roof 1 year old, fenced yard, storage building private drive. nice back yard and more.

222 Holiday Rd, Winchester
319 Essex Ct, Winchester
$195,000
3 Beds ⋅ 3 Baths ⋅ 26003610 MLS
This Colby Ridge neighborhood townhome location is hard to beat as it is just minutes from Kroger, Walmart, the Bypass, interstate access, and a wide variety of restaurants and everyday conveniences. The main floor offers a convenient half bath, a welcoming living room that opens naturally into the dining area and kitchen, and a laundry room tucked just inside the one-car garage entry. Off the dining area, step out onto the back deck (built in 2023) overlooking a fully fenced yard which is a great spot to relax or let pets play. The unfinished walkout basement adds plenty of storage space with room to expand in the future. Upstairs, you'll find three bedrooms and a full bath, including a primary suite with double closets and a private bath with a shower. With a practical layout, inviting outdoor space, and an unbeatable location, this townhome is ready for its next owner.

319 Essex Ct, Winchester
611 College St, Winchester
$195,000
2 Beds ⋅ 2 Baths ⋅ 26025674 MLS
This updated ranch is an easy walk to College Park and College Gym. You will love the huge backyard with a 2-car detached garage for storage or possibly a workshop plus extra storage in the storage building. No steps in the house! New flooring has recently been installed with fresh paint and updated lighting. Each bedroom is very spacious. The roof is only 3 years old. This cutie has a spacious open concept living area. The home checks all the boxes for the perfect first-time home buyer. It would also be perfect for someone wanting to downsize. 611 College St. is your reason to stop renting and start owning.

611 College St, Winchester
246 Geronimo Ct, Winchester
$192,565
3 Beds ⋅ 2 Baths ⋅ 25506870 MLS
This little cutie sits at the end a cul-de-sac and backs to a farm. I'm not sure it gets much better! This 3 bedroom/2 full bath home is ready for you! The living room opens up into the eat-in kitchen boasting stainless steel appliances. The kitchen leads to the back deck that overlooks your fenced in backyard and views of the farm behind the house. 3 bedrooms and 2 full bathrooms round out this home. The roof was replaced in mid-November. Schedule your showing today!

246 Geronimo Ct, Winchester
29 Euclid Ave, Winchester
$190,000
3 Beds ⋅ 2 Baths ⋅ 26006180 MLS
Welcome to 29 Euclid Ave in the heart of downtown Winchester! This charming home features 3 bedrooms, 2 bathrooms, and a versatile bonus room that can be used as a home office, playroom, guest space, or additional living area. The home offers generously sized bedrooms with plenty of space to relax and unwind. Located just minutes from local shops, restaurants, and everything downtown Winchester has to offer, it's perfect for anyone looking for both comfort and convenience. Step outside to enjoy the deck, ideal for entertaining or relaxing in the evenings, along with a backyard shed that provides extra storage space. With its great location, spacious layout, and flexible bonus room, this home has so much to offer. Don't miss the opportunity to make it yours!

29 Euclid Ave, Winchester
2721 Pretty Run Rd, Winchester
$190,000
3 Beds ⋅ 2 Baths ⋅ 24025198 MLS
Back on market due to buyer financing, no fault of the seller! Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer flexibility for family, guests, or work-from-home needs. Outside, the acreage provides ample space for outdoor projects, recreation, or enjoying the peaceful surroundings. Two storage sheds add convenience for tools, equipment, or additional storage. This property is ready for a new owner to bring their vision and make it their own. Experience the quiet charm of country living just a short drive from town!

2721 Pretty Run Rd, Winchester
325 Essex Ct, Winchester
$190,000
2 Beds ⋅ 2 Baths ⋅ 26022515 MLS
FRESHLY PAINTED BRAND NEW APPLIANCES HUGE FENCED BACKYARD NEWER PRIVACY FENCE FIRST TIME BUYER OPPORTUNITY INVESTMENT OPPORTUNITY $1,000 BUYER CREDIT Welcome to 325 Essex Ct in Winchester! This charming 2 bedroom, 1.5 bath home offers an excellent opportunity for a first time homebuyer or investor looking for an affordable property with great potential. Inside, you'll find fresh paint and brand new appliances, giving the home a clean and refreshed feel. The spacious backyard is a standout feature, offering plenty of room for pets, entertaining, gardening, or simply enjoying your own private outdoor space, with a newer privacy fence already in place. With a functional layout, desirable updates, and a large fenced in yard, this home is ready for its next owner. Whether you're looking to stop renting and make homeownership a reality or add another property to your investment portfolio, this one is worth a look! Plus, the lender I work with is offering a $1,000 buyer credit to qualified buyers. Don't miss your opportunity to make 325 Essex Ct your next home or investment!

325 Essex Ct, Winchester
357 E Washington St, Winchester
$189,900
3 Beds ⋅ 2 Baths ⋅ 26000958 MLS
Completely renovated and move-in ready, this beautifully updated home combines modern finishes with an unbeatable walkable location. Featuring a brand-new roof, new flooring throughout, and fresh paint from top to bottom, every inch of this home has been thoughtfully refreshed. The kitchen has been fully remodeled with new cabinets, new appliances, and a stylish butcher block countertop—perfect for both everyday living and entertaining. Both bathrooms have also been completely renovated with clean, contemporary finishes. Enjoy the convenience of being less than one mile from downtown Winchester, just 0.4 miles from the local elementary school, and only a 5-minute walk to Massie Park. Whether you're looking for charm, location, or turnkey condition, this home delivers on all fronts. A rare opportunity to own a fully renovated property in one of Winchester's most walkable areas.

357 E Washington St, Winchester
13015 Irvine Rd, Winchester
$189,500
25014720 MLS

13015 Irvine Rd, Winchester
111 Quail Ridge Rd, Winchester
$189,000
2 Beds ⋅ 3 Baths ⋅ 26000646 MLS
Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining guests. Enjoy the privacy of your fenced backyard, ideal for outdoor dining or relaxing evenings. The attached garage adds storage and year-round convenience. With easy access to shopping, parks, and restaurants—and just a short drive to Lexington—this home combines modern comfort with a great location. Move-in ready and beautifully maintained, this townhome is a must-see for anyone looking for low-maintenance living with lasting appeal

111 Quail Ridge Rd, Winchester
27 Ashland Ave, Winchester
$188,000
3 Beds ⋅ 2 Baths ⋅ 25501148 MLS
Motivated Seller! Move right in and enjoy this well-maintained 3-bed, 2-bath ranch in the heart of Massie Addition! Thoughtfully updated with a recent roof on both the home and garage, a brand-new hot water heater (2025), and a modern, fresh interior paint palette, this home is ready for you. A home warranty covering all major systems and appliances is included for added peace of mind. This stately older home has many original features, adding to its timeless character and charm. The generous ~half-acre lot offers room to garden, play, or relax under the trees, while the detached 2-car garage provides excellent storage and parking. With everything on one level and just a short stroll to downtown Winchester's refreshed shops, dining, and year-round events, this property is ready for its next chapter.

27 Ashland Ave, Winchester
31 Vine St, Winchester
$186,500
3 Beds ⋅ 1 Baths ⋅ 25017033 MLS
Welcome to this beautifully updated 3-bedroom, 1-bath home, perfectly situated in the vibrant heart of Winchester. Bursting with charm and character, this home offers the best of modern updates and classic appeal. Step inside to discover a bright, open living area with new flooring, fresh paint, and stylish finishes throughout. The updated kitchen features sleek cabinetry, granite countertops, and stainless steel appliances. Enjoy cozy evenings in the spacious living room or host summer gatherings in the expansive backyard. The remodeled bathroom boasts contemporary tilework and updated fixtures. With thoughtful upgrades and move-in ready condition, this home is perfect for first-time buyers, downsizers, or investors. All this just minutes from Winchester's shops, dining, parks, and commuter routes. Don't miss your chance to own this delightful home in a desirable location—schedule your showing today!

31 Vine St, Winchester

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