Winchester Real Estate | Winchester Properties between $200,000 and $300,000 for Sale

Welcome to this freshly renovated farmhouse in the heart of Trapp, Kentucky! Blending timeless farmhouse charm with fresh updates, this property is ready for its next chapter. The possibilities are endless—come see all this special home has to offer. An absolute must-see!

11304 Irvine Rd, Winchester

$235,000

3 Beds ⋅ 1 Baths ⋅ 26023896 MLS

Welcome to 119 Tower Lane! This beautifully remodeled 3-bedroom, 1-bath home offers the perfect combination of modern updates and peaceful country living. Situated on 5 acres, there's plenty of room to enjoy the outdoors, spread out, and make the property your own. Whether you're looking for a move-in-ready home with acreage or a peaceful place to call home, this property is one you won't want to miss! Privately positioned and surrounded by natural beauty, this renovated berm-style residence offers the perfect balance of seclusion and sophistication. Inside, you'll find thoughtfully curated updates including fresh paint, updated flooring, and a bright, inviting interior that feels both modern and timeless. The kitchen has been refreshed with contemporary appliances and stylish finishes, offering a functional and comfortable space for everyday living. Featuring three bedrooms and an updated bath, the home delivers comfort with understated elegance. Energy-efficient berm construction enhances year-round efficiency and quiet living. Outdoors is where this property truly shines. Five unrestricted acres create endless potential for recreation, gardening, animals, or simply enjoying unmatched privacy and open space. A covered carport adds convenience. A distinctive property that combines modern updates, privacy, and opportunity all just minutes from town!

119 Tower Ln, Winchester

$225,000

4 Beds ⋅ 2 Baths ⋅ 26023784 MLS

This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. The property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

522 Acadia Way, Winchester

$219,900

3 Beds ⋅ 3 Baths ⋅ 26023771 MLS

Bring your vision and make this home your own! Situated on a huge corner lot on the outskirts of Winchester, this three-bedroom, two-and-a-half-bath home offers plenty of space and potential. Features include a two-car garage and a convenient location just minutes from the Bypass and I-64. The interior needs some TLC, including new flooring and/or carpet, seller is willing to give up to $10,000 in concessions at closing towards repairs making this a great opportunity to update the home to your personal style. Located in a quiet neighborhood, this property has so much to offer. Don't miss out—schedule your private showing today!

330 Vanover Way, Winchester

$244,000

3 Beds ⋅ 2 Baths ⋅ 26023633 MLS

SHORT SALE OPPORTUNITY! 54 Locust Dr. is an all-brick ranch in Westland Park offering 3 bedrooms, 2 baths and 1,692 sq. ft. of finished living space, plus a full unfinished basement. The home features hardwood flooring, a 2-car attached garage, fenced backyard and covered patio. Previous owners completed structural work in the basement that includes a transferable lifetime warranty. The home retains much of its original character and offers an opportunity for a buyer to update the kitchen, baths and finishes to their own style. This property is being offered as a short sale, meaning the seller's lender must review and approve the purchase price and terms. Please allow approximately 30-45 days for lender review and approval of any offer. Property is being sold AS-IS; inspections are welcome.

54 Locust Dr, Winchester

$250,000

2 Beds ⋅ 1 Baths ⋅ 26023419 MLS

Discover the timeless charm of this storybook river house, perfectly nestled on a private 2 acres with river views and access.Completely renovated, new stove, full of character and warmth, this unique 2 bedroom, one bath retreat offers a peaceful escape with an incredible connection to the water and quiet nature. Inside the charming shiplap walls and two fireplaces create a cozy, inviting atmosphere. The impressive stone fireplace serves as beautiful focal point, while a second fireplace adds even more warmth and ambiance. Step outside and enjoy your own private connection with the river, perfect for launching your kayak into the water or just enjoy the sounds of the water by the riverbank. Private weekend getaway or full time residence, or one of a kind investment property, this charming river house offers something truly special- privacy, character, tranquility, and direct access to the Ky River. Bonus, Halls on the River is a stones throw away! Would be an amazing VRBO

682 Athens Boonesboro Rd, Winchester

$280,000

4 Beds ⋅ 2 Baths ⋅ 26023223 MLS

Excellent location! 4 bedroom, 2 bath. This home offers one level living on the edge of town and close to the interstate! AMAZING VIEWS of country side! Two living room spaces! Split bedroom design. Covered back patio. NEW LVP flooring. NEW electric service panel and meter base. Freshly painted throughout. NEW appliances. Fully fenced backyard. This home is move in ready. Come see today!

198 Hilltop Dr, Winchester

$275,000

3 Beds ⋅ 2 Baths ⋅ 26023105 MLS

Immaculately maintained and move-in ready! This 3-bedroom, 2-bath home is tucked along a cul-de-sac street and offers a spacious living room with vaulted ceiling, light-filled sunroom, well-kept kitchen with stainless appliances, and both bathrooms updated within the last four years. Enjoy even more living space outdoors on the covered, screened back deck overlooking the backyard. Conveniently located near shopping, restaurants and I-64 for an easy commute to Lexington.

204 Lindsey Ct, Winchester

$229,900

3 Beds ⋅ 1 Baths ⋅ 26023054 MLS

Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable one-level living.

125 Kittison Dr, Winchester

$249,900

26022811 MLS

Has your small business officially outgrown the garage, basement, spare bedroom- or possibly all three? It might be time for a space of its own! This versatile property offers approximately 550 square feet of finished office space plus approximately 1100 square feet of shop/warehouse space. The office area gives you plenty of flexibility for a private office, reception/waiting area, additional workspace or storage, plus one restroom. Out back, the shop/warehouse is ready to work with a gas heater, new LED lighting and two 14' x 14' overhead doors with openers- perfect for vehicles, equipment, inventory or whatever your business needs to keep moving. Most of the work has already been done for you! You'll find fresh paint inside and out, new flooring throughout, and a brand-new blacktop parking lot. Convenient to I-64, Lexington and surrounding Central Kentucky communities, this could be a great fit for a contractor, service-based business or small business owner who simply needs more room to work, store, and grow. Because eventually, your kitchen table would probably like to go back to just being a kitchen table. Listing agent is related to seller.

506 N Main St, Winchester

$215,000

3 Beds ⋅ 2 Baths ⋅ 26022771 MLS

Welcome to 3 Nunnelly Ct, Winchester, KY This charming 3-bedroom, 2-bathroom home offers comfortable living with several important updates already in place. Featuring a newer HVAC system and newer roof, this home provides peace of mind for its next owner while offering plenty of opportunity to make the space your own. Inside, you'll find a bright, inviting layout with fresh, neutral finishes, updated flooring, and plenty of natural light. The spacious living area features a classic brick fireplace, creating a warm focal point for relaxing or entertaining. The updated kitchen offers new white cabinetry, stainless steel appliances, subway tile backsplash, ample counter space, and new granite countertops. Both bathrooms have been updated with clean, modern finishes, including attractive tile work and contemporary fixtures. The home's three bedrooms provide flexibility for family, guests, a home office, or additional living space. Outside, enjoy a covered front porch and established, tree-lined surroundings that provide a private and welcoming setting. The rear of the property offers additional outdoor space and a detached storage/outbuilding area. Conveniently located in Winchester, this home combines a comfortable residential setting with easy access to local shopping, dining, schools, and major roadways. Whether you're looking for a primary residence or an investment opportunity, this well-maintained home is worth a look!

3 Nunnelly Ct, Winchester

$254,900

3 Beds ⋅ 3 Baths ⋅ 26022409 MLS

Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for entertaining or gathering with family and friends. The lower level adds even more flexibility with a bonus room that could serve as a home office, recreation room, workout space, or additional living area. Upstairs you'll find 3 bedrooms, 2 full bathrooms, and ample closet space throughout. Outside, enjoy a large backyard backing to green space, along with the convenience of a rear-facing garage and a neighborhood walking trail. Ideally located with quick access to I-64 and approximately 20 minutes from Lexington's Hamburg area, this home combines space, updates, low-maintenance living, and a convenient location in one inviting package. Schedule your private showing today!

127 Bay Hill Dr, Winchester

$265,000

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

$234,500

3 Beds ⋅ 2 Baths ⋅ 26022078 MLS

NEW roof, NEW kitchen appliances, NEW deck, and more! Welcome to 527 Hidden Hills Way! Located on a quiet cul-de-sac, this renovated one level home is ready for you to move right in. Vaulted ceilings give an open and airy feel, while fresh paint throughout offers a neutral palette for any design style. The spacious kitchen includes plenty of oak cabinetry, a separate pantry, stainless steel appliances, and easy access to the backyard. Hardwood flooring extends from the living room to the hallway, and new carpet has been installed in the bedrooms. The large primary bedroom includes an updated ensuite bathroom. The new deck overlooks the private backyard, and the covered front porch offers the perfect spot to enjoy views of your peaceful, low traffic street. Conveniently located just minutes from downtown Winchester, schools, shopping, dining, and easy access to I-64, this home provides the best of both convenience and small town charm. Schedule your showing today!

527 Hidden Hills Way, Winchester

$295,000

2 Beds ⋅ 1 Baths ⋅ 26022030 MLS

Come see this beautiful 13-acre property in the Historic Boonesborough area of Clark County, offering peaceful country living with the convenience of being just minutes from Winchester, Richmond, and Lexington. The property features a 2-bedroom, 1-bath home with 1,344 sq. ft., surrounded by beautiful acreage with plenty of room for animals, recreation, gardening, or simply enjoying the outdoors. The home has new plumbing, as well as new wiring. A brand-new 30x40 metal garage on a concrete slab provides excellent space for vehicles, equipment, storage, or hobbies. An additional workshop area next to the garage offers even more room for projects and workspace. With 13 beautiful acres, usable land, new outbuildings, and a convenient location, this property offers a great opportunity to enjoy country living while staying close to town. Schedule your showing today!

405 Nick Ln, Winchester

$300,000

4 Beds ⋅ 2 Baths ⋅ 26021718 MLS

Classic character and generous living space come together at 224 W Hickman Street in Winchester. This single-family residence offers 4 bedrooms, 2 full bathrooms, and approximately 2,479 square feet, providing a flexible layout with room for a variety of everyday living needs. The home's substantial interior footprint creates opportunities for comfortable gathering spaces, private bedrooms, a home office, hobbies, or additional storage. Conveniently located in Winchester, this property offers an appealing combination of space and established residential character.

224 W Hickman St, Winchester

$229,900

3 Beds ⋅ 2 Baths ⋅ 26021639 MLS

This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location

106 Quail Ridge Rd, Winchester

$205,400

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

$234,900

3 Beds ⋅ 2 Baths ⋅ 26021123 MLS

This 3 Bedroom, 2 bath home is quietly nestled within the Saddle Brook subdivision. Conveniently located just outside of Winchester New Bypass, this property also qualifies for zero down rural housing financing. Updates can be seen throughout along with spacious master bedroom with on-suite, large back yard and open concept living. Schedule your showing today!

227 Leslie Dr, Winchester

$219,900

26020972 MLS

PRIME COMMERCIAL PROPERTY!!!! High traffic, high visibilty, with a ton of potential! Exceptional commercial property located in an excellent location with outstanding exposure for your business. Positioned on a busy roadway, this property offers maximum visibility to thousands of passing vehicles each day, making it an ideal location for retail, office space, a restaurant, medical practice, or service-based business. With easy access, excellent frontage, and endless potential, this is a rare opportunity to establish or expand your business in one of the area's most sought-after commercial corridors. Don't miss your chance to invest in a location where your business can thrive. Located within close proximity to the planned Publix and new shopping center. Agent/owner

106 Mcclure Rd, Winchester

$250,000

4 Beds ⋅ 2 Baths ⋅ 26020680 MLS

PRICED TO SELL | BRING AN OFFER! Highly Motivated Seller! 59 Hillcrest Dr, Winchester, KY 40391 3 Beds | 2 Baths | ~2,066 Total Sq Ft | Full Basement | Large Lot Attention buyers, DIYers, and investors: Don't miss this incredible value! The seller is highly motivated and ready to entertain offers, making this attractive ranch home priced to sell immediately with the oppurtunity to unlock instant equity! Key Highlights: Potential Mother-in-Law Suite: The fully finished, remodeled lower level includes a full bath, separate living area, dedicated laundry, its own entrance, and a non-conforming 4th bedroom (or ideal home office/hobby room)—offering the perfect layout for a mother-in-law suite, guest quarters, or independent living space. New HVAC! Original Hardwood Floors: Character and potential await! Classic original hardwood flooring runs through the main level, begging to be refinished to showcase its natural warmth and beauty. Expansive Yard Space: Enjoy outdoor freedom on a huge lot! Featuring a spacious, fully fenced back yard with endless possibilities for play, pets, or entertaining. Versatile Layout: Upstairs main-level living area combined with a versatile basement setup to suit any household's needs. Walk out basement provides seperate entrances to each level. Location & Value: Nestled in an established neighborhood in winchester, moments from GRC, and quick access to Lexington and Richmond! Opportunities with this much space, flexible living arrangements, and upside don't last long—bring all reasonable offers! Agent is owner.

59 Hillcrest Dr, Winchester

$289,900

4 Beds ⋅ 3 Baths ⋅ 26020651 MLS

Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and bathroom on the main floor, cathedral ceiling , covered front porch, large basement garage facing the rear of the home. Home is very convenient to downtown area and I-64. Dont drag your feet this one wont be on the market long.

428 Waycross Dr, Winchester

$225,000

26019968 MLS

Located on the very visible corner of Lexington Avenue and Main Street, this property has recently been updated. Wonderful tenants in both the upstairs and downstairs unit makes this a great investment property. The historic Leeds Center for the Arts, numerous other restaurants and shops are in walking distance. This is an ideal location for an investment property or bring your business here. This property is also located in the Opportunity Zone. Lots of options! Winchester, KY is conveniently situated just 18 miles east of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, La Trattoria, Loma's, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown Winchester - residents and tourists want to be Downtown! Property Highlights: -Excellent investment property with Tenants in place -Ideal location in Downtown Winchester -Located in the Opportunity Zone

1 N Main St, Winchester

$234,900

3 Beds ⋅ 2 Baths ⋅ 26018492 MLS

*NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining. Step outside and enjoy your own Aurora above-ground pool, just in time for summer fun! The partially fenced backyard also includes an oversized storage/tool shed, providing plenty of room for hobbies and extra storage. Enjoy peace of mind with major updates, including a newer HVAC system, water heater, Window World windows (approximately 5 years old), and a new roof with a 5-year warranty. As an added bonus, the seller is offering up to a $2,500 flooring allowance with an acceptable offer. Please include the flooring allowance in any written offer. Don't miss the opportunity to make this inviting home yours!

528 Estes Dr, Winchester

$259,000

3 Beds ⋅ 2 Baths ⋅ 26018346 MLS

Welcome home to this beautifully renovated home in the desirable Bon Haven subdivision! From the moment you step inside, you'll appreciate the bright and inviting living room that flows seamlessly into the updated kitchen, creating a warm and functional space for everyday living. The main level features two spacious bedrooms and two full bathrooms, while the second floor offers a private third bedroom; perfect for a guest room, home office, or primary retreat. The unfinished 780-square-foot basement provides endless possibilities for additional living space, a recreation room, or extra storage. Located within walking distance of the popular Legacy Grove Park, you'll enjoy easy access to walking trails, green space, and outdoor recreation. Move-in ready and thoughtfully renovated, this home is ready for its next owner.

33 Bon-Haven Ave, Winchester

$259,900

3 Beds ⋅ 1 Baths ⋅ 26016881 MLS

SELLING "AS IS" Welcome to country living!! approximately 1 acre lot with 3-car garage. updates include; new basement doctor system, new range, refrigerator, dishwasher, and washer/dryer. New LVP flooring, new light fixtures inside and out. New septic system, new front storm door and new sliding glass door in dining room. New electric outlets and switch plates. New garage door on lower one car garage. New gutters. Motivated seller. Move-in condition. Schedule your viewing appointment today!!

2379 Big Stoner Rd, Winchester

$219,500

3 Beds ⋅ 2 Baths ⋅ 26017144 MLS

Welcome home to this charming 3-bedrooms, 2-bath ranch perfectly situated in the heart of Winchester! Offering the convenience of one-level living, this inviting 1200 sq ft home combines comfort, functionality, and an unbeatable location. Primary bedroom is en suite and offers plenty of closet space. Additional 2-bedrooms and 1-bath provide plenty of space. Enjoy easy access to schools, shopping, restaurants, parks, and local amenities—all just minutes from your front door. Inside, you'll find a spacious and welcoming open floor plan with comfortable living areas, generously sized bedrooms, and plenty of natural light throughout. Whether you're a first-time home buyer, looking to downsize, or searching for the perfect home, this property offers endless potential to make it your own. Don't miss this opportunity to own a well-located home that puts everything you need within reach. Seller offering $3000.00 paint and flooring allowance to buyer with accepted contract.

491 Hidden Hills Way, Winchester

$219,900

26016689 MLS

Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find. Conveniently located just minutes from Winchester off the Mountain Parkway, exit 10, and an easy commute to Lexington.

3686 Crowe Ridge Rd, Winchester

$225,000

26005737 MLS

Wonderful 24 acre retreat with gentle sloping land, and a creek bed running thru part of the front portion of the lots (6.1 acre parcel & 18.4 acre parcel at the rear). Build your dream home or just use as recreational or farm land until you do. 1 1/2 miles to the first exit on the Mountain Parkway exit #10. 12 miles to I-64 at Winchester. See attached pictures & plat/overhead pictures.

3934 Trapp-Goffs Corner Rd, Winchester

$219,000

3 Beds ⋅ 2 Baths ⋅ 26011961 MLS

Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

14 Cook Ave, Winchester

$299,900

4 Beds ⋅ 3 Baths ⋅ 26015653 MLS

Very motivated sellers, Get here first, make an offer on this 4 bedroom, 3 bath, 1 1/2 story home, 2 car garage, showroom fresh condition, vaulted ceiling, hardwood floors, tile, carpet, deck, nice back yard, call today to view.

209 Connie Ln, Winchester

$270,000

20111867 MLS

Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

800 Interstate Dr, Winchester

$299,999

25001584 MLS

An excellent opportunity to own a fully leased, income-producing property in the heart of Downtown Winchester, Kentucky. This beautifully renovated 2,310 SF retail storefront is being offered at a 10% cap rate, making it an attractive turnkey investment from day one. The building may be old, but nearly everything inside is new! Recent improvements include a new roof, four new skylights, exposed beams, new hardwood flooring throughout, updated electrical and plumbing, and HVAC. The space is plumbed for four bathrooms and also includes a laundry room and private back office with a window overlooking the main retail area. This property boasts a large rear parking lot—one of the largest in Downtown Winchester—providing convenient parking for tenants, customers, and employees. The location is surrounded by continued downtown growth. Seven new high-end apartments across the street, while the same block is already home to five restaurants, numerous shops, and the Leeds Center for the Arts. Property Highlights: -Recently renovated with a new roof, 4 new skylights, exposed beams, new hardwood floors, new plumbing and new electrical. -The property is located directly across from a brand-new apartment building and is surrounded by retail and restaurants. -The property boasts the largest back parking lot in the downtown area, a bonus for staff and customer accessibility. -Downtown Winchester, KY is booming - everyone wants to be Downtown, introducing shops, restaurants, and new apartment living options. Winchester, KY is conveniently situated just 18 miles east of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, La Trattoria, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown Winchester - residents and tourists want to be Downtown!

16 N Main St, Winchester

$300,000

20111875 MLS

Easy Location, Metal/Pole Barn approx 1675sqft, type garage on site with three 10x10 garage doors, two 8ft doors and 2 entrances, currently split access to each side, Utilities on site per seller/per plat, water and gas is not hooked up to building, zoned B-3. .58 acres located at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property sold As Is buyer to verify all information and access to water, gas, electric and locations. Per seller egress and ingress rights down Holiday Drive to building.

1045 Early Dr, Winchester

$249,500

26007074 MLS

Discover the perfect blend of beauty, privacy, and opportunity with this stunning 14.511-acre tract on Irvine Road. Featuring gently rolling hills, this property offers multiple ideal building sites to bring your dream home to life, whether you're envisioning a modern farmhouse, barndominium, or private country retreat. A barn is already in place, adding immediate functionality for storage, livestock, or future homesteading plans. The property also includes partial fencing, making it even more appealing for those looking to accommodate animals or create a mini-farm setup. One of the standout features is the picturesque creek that runs through the property, adding both natural beauty and a peaceful setting you'll enjoy year-round. With a balance of open space and scenic landscape, this land offers the kind of tranquility that's getting harder to find while still being conveniently located near town. Looking for even more space? The adjoining 11.362-acre tract (MLS #26007067) is also available, creating a rare opportunity to own over 25 acres of contiguous land. perfect for a private estate, multi-generational living, or future investment potential. Whether you?re ready to build now or invest for the future, this property checks all the boxes for Kentucky land buyers seeking space, scenery, and flexibility. Don't miss your chance to own a slice of Kentucky countryside! RESTRICTIONS MAY BE REMOVED BY SELLER IF BOTH TRACTS 2996 AND 3056 ARE PURCHASED. Schedule your showing today.

3056 Irvine Rd, Winchester

$250,000

26013923 MLS

Exciting opportunity for congregations, investors, or visionaries seeking a one-of-a-kind property! This spacious one-level property offers over 2,500 sq ft with 2 bathrooms, a roof that is approximately 6 years old, and endless possibilities for renovation or repurposing. Situated on a quiet street, this unique space provides the perfect canvas to bring your vision to life. Property is being sold as-is. Buyers to verify square footage and lot size.

3150 Waterworks Rd, Winchester

$258,900

2 Beds ⋅ 1 Baths ⋅ 26013194 MLS

Newly renovated Cabin sitting on +- 5 acres. Renovations began in 2024 and were completed in 2026. An ideal property for a first-time home buyer or anyone looking for a remote quiet location located within 20 minutes of downtown Winchester.

955 Right Angle Rd, Winchester

$239,000

4 Beds ⋅ 4 Baths ⋅ 26000922 MLS

Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

1128-1130 Dale Dr, Winchester

$239,900

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. All this in a great location, just minutes from Lexington, the horse capital of the world, with beautiful Kentucky horse farms! And just 45 minutes from the famous Red River Gorge! This home is right in the center of it all, city life and the beautiful outdoors! Don't miss this wonderful opportunity to make this charming home your own!

377 Crescent Ave, Winchester

$280,000

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

$275,000

3 Beds ⋅ 2 Baths ⋅ 26007260 MLS

Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

103 Southern Ct, Winchester

$220,000

4 Beds ⋅ 3 Baths ⋅ 26004331 MLS

Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income potential in a prime downtown location with continued upside. Selling as-is.

130 E Broadway St, Winchester

$274,500

3 Beds ⋅ 2 Baths ⋅ 26011465 MLS

Welcome to this delightful 1.5-story home perfectly situated on a spacious corner lot just off the Eastern Bypass and only minutes from I-64. Convenience meets comfort in this beautifully maintained property offering 3 bedrooms, 2 full baths, and an inviting layout designed for everyday living. Step inside to an open living area ideal for entertaining, a spacious kitchen and dining space, and plenty of room for family and friends to gather. Natural light fills the home, creating a warm and welcoming atmosphere throughout. Outside, enjoy an oversized backyard complete with a charming white picket fence — perfect for children, pets, gardening, or hosting outdoor entertaining. Whether you're a first time buyer or searching for your forever home, this property offers comfort, convenience, and character all in one. Call today for more information or to schedule your private showing. Note: Offer to Purchase with Contingency and Kick-out Clause. Buyer cannot perform without the sale of current property.

137 Eastridge Dr, Winchester

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Amanda Marcum - MARCUMsold

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