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600 College St, Winchester
$220,000
3 Beds ⋅ 2 Baths ⋅ 26026485 MLS
Welcome to 600 College Street! Offering over 1,700 square feet, this versatile Winchester home features 3 bedrooms, 2 full bathrooms, plus an additional room ideal for a 4th bedroom, home office, or flex space. Inside, you'll find a spacious living room and a dining room with plenty of room to create additional living or entertaining space. The kitchen offers a walk-in pantry and conveniently located laundry area. An unfinished basement provides ample storage and walkout access, while the attached one-car garage adds everyday convenience. Outside, enjoy a covered front porch and a peaceful back porch surrounded by mature trees for added privacy. Conveniently located near Downtown Winchester, College Park, Legacy Grove, local shopping, dining, and everyday amenities, with easy access to I-64 for a straightforward commute toward Lexington. Improvements, including a roof replacement, LVP flooring, renovated kitchen and baths, and updated plumbing all done in 2024. Schedule your private showing today!

600 College St, Winchester

609 W Barlow Dr, Winchester
$375,000
4 Beds ⋅ 2 Baths ⋅ 26026446 MLS
Welcome to your new home. Move-in ready inside and out, this 4-bedroom, 2-full-bath home offers comfortable living, plenty of finished space, and a backyard that truly feels like your own private retreat! The home has been well cared for and thoughtfully updated, including new flooring throughout the entire finished portion of the basement, new toilets, and a new dishwasher and stove. Step outside and you'll quickly see what makes this property special. The in-ground pool and surrounding outdoor living space are an absolute dream, with extensive improvements completed to make it ready for years of enjoyment. All-new concrete was installed around the pool in 2025, along with a new pool liner and gas pool heater, plus a newer pool pump. A new privacy fence installed in 2023 creates a secluded setting, while the gazebo—complete with electricity—provides the perfect spot to relax, entertain, or spend summer evenings by the pool. The improvements continue with a brand-new back porch completed in May 2026 and a new concrete driveway in 2026, adding even more value and curb appeal. Whether you're entertaining friends around the pool, enjoying a quiet evening under the gazebo, or taking advantage of the additional finished basement space, this home offers a lifestyle that's hard to duplicate. Move in, unpack, and start enjoying it from day one!

609 W Barlow Dr, Winchester

335 Newcastle Ln, Winchester
$304,900
3 Beds ⋅ 3 Baths ⋅ 26026107 MLS
Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite. Recent updates include a brand-new roof, along with manufactured hardwood flooring installed in the living area, foyer, and primary bedroom. Conveniently located near the Winchester Bypass, this home offers quick access to shopping, dining, and everyday amenities, while also providing easy access to I-64, I-75, Lexington, and the Mountain Parkway for commuters and travelers. Offering a desirable combination of space, updates, and location, this home is ready for its next owner to enjoy. Schedule your private showing today!

335 Newcastle Ln, Winchester

102 Quail Ridge Rd, Winchester
$239,000
3 Beds ⋅ 3 Baths ⋅ 26025942 MLS
This move-in ready townhome is located in Greenfield subdivision and sits on a quiet street with no through traffic. On the main level you will find 2 nicely sized bedrooms , 2 full baths, laundry closet along with a fully closed in sun-porch. The living room is spacious and the kitchen is equipped with top notch appliances. Below you will find the walkout basement where there is another bedroom, nice storage area with a half bath and a nice living or office area. Roof replaced this year, hot water heater replaced in 2025 and air replaced in 2023. Great location!! Close to schools, restaurants and shopping with I-64 only 2 miles away! Approximately 20 minutes from Hamburg. There is a very friendly cat that will be closed in the sun porch please don't let him out.

102 Quail Ridge Rd, Winchester

6 French Ave, Winchester
$296,000
4 Beds ⋅ 2 Baths ⋅ 26025571 MLS
SPACE, CHARACTER & LOCATION—THIS HOME HAS IT ALL! Step inside and discover a home filled with charm, character, and plenty of room to make your own. Featuring 4 generously sized bedrooms and 2 bathrooms, this home offers space for everyone to spread out. Beautiful original wood floors throughout the home add warmth and timeless character you just can't recreate. Enjoy the charm of the beautiful front porch, perfect for morning coffee or relaxing at the end of the day. Out back, the privacy-fenced yard provides a wonderful space for entertaining, pets, play, or simply enjoying the outdoors. Add in the convenience of a great location, and this home has so much to offer. Spacious rooms, original character, and a location you'll love—this is one you'll want to see in person!

6 French Ave, Winchester

115 Quail Ridge Rd, Winchester
$225,000
3 Beds ⋅ 3 Baths ⋅ 26025201 MLS
Looking for low-maintenance living without giving up space? This Winchester townhouse offers three bedrooms, 2.5 baths and a comfortable two-story layout with room to spread out. The main level features a spacious living room with a fireplace, dining area, kitchen and half bath. Just off the dining area, the back deck gives you a nice spot to relax or enjoy some time outside. Upstairs, the primary bedroom has its own private bath and large walk-in closet, along with two additional bedrooms, another full bath and laundry. There's also an attached garage and plenty of closet space throughout. A great option for anyone looking for an easy-to-maintain home with the space and storage you don't always find in a townhouse.

115 Quail Ridge Rd, Winchester

209 E Washington St, Winchester
$159,000
3 Beds ⋅ 1 Baths ⋅ 26024016 MLS
Conveniently located in Winchester, this one-story home offers three bedrooms, one bath, and plenty of potential for a first-time buyer or investment property. Inside, you'll find laminate and vinyl flooring throughout, a spacious kitchen, and a separate laundry room. The bathroom received new fixtures in 2025, while the roof is approximately 1.5 years old, taking care of two worthwhile updates for the next owner. Gas freestanding heaters provide heat, and the home does not currently have central air. Outside, there's a covered front porch and a nice-sized backyard with an alley running behind the property. Whether you're looking for an affordable place to call your own or an addition to your rental portfolio, this home is ready for its next chapter.

209 E Washington St, Winchester

119 Tower Ln, Winchester
$227,900
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

54 Locust Dr, 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

3208 Ford Hampton Rd, Winchester
$135,000
2 Beds ⋅ 1 Baths ⋅ 26023193 MLS
Set on a half-acre in a rural Winchester setting, this 2-bedroom, 1-bath home offers an efficient one-level layout with approximately 807 square feet of living space. The eat-in kitchen provides a comfortable spot for everyday meals, while main-level laundry hookups add convenience. Front and rear porches extend the living space outdoors and offer places to enjoy the surrounding trees, countryside, and views. A metal roof adds practicality, and the property's location near the Kentucky River provides easy access to one of the area's notable natural features. Whether you're looking for a primary residence, weekend getaway, or a smaller property with a little room around it, 3208 Ford Hampton Road offers a straightforward home in a scenic rural setting.

3208 Ford Hampton Rd, Winchester

15 Moundale Ave, Winchester
$359,900
3 Beds ⋅ 2 Baths ⋅ 26023052 MLS
Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of finished living space, this 3-bedroom, 2-bath home combines timeless character with an impressive list of thoughtful updates. The main level features a spacious family room with ventless gas logs, a beautifully updated kitchen with custom cabinetry, granite countertops, and stainless appliances, and a versatile dining room that can easily serve as a home office. The former sunroom was converted to finished living space in 2021 and now provides an inviting all-seasons room along with a convenient laundry area overlooking the backyard. Upstairs, the private primary suite offers a generously sized bedroom, full bath, and an impressive three walk-in closets. An unfinished basement provides abundant storage and additional possibilities for future use. The extensive improvements throughout the property add tremendous value and peace of mind, including PEX plumbing lines, HVAC and water heater replaced in 2021, a whole-home generator installed in 2021, a new roof in 2025, new gutters, exterior doors, chimney cap, French drain, and fencing. Kitchen appliances, including the refrigerator, range, dishwasher, and microwave, were replaced in 2020, while the exterior brick has also been freshly painted as part of the home's updates. Outside, enjoy a professionally leveled and graded yard with plenty of room to relax or entertain. And with the whole-home generator, you'll have the added comfort of backup power when you need it most. Conveniently located just minutes from historic downtown Winchester, the bypass, shopping, dining, and I-64, this move-in-ready home offers the character of an established property with many of the major updates today's buyers are looking for. Schedule your private showing and see everything this exceptional Winchester home has to offer!

15 Moundale Ave, Winchester

3 Nunnelly Ct, Winchester
$205,000
3 Beds ⋅ 2 Baths ⋅ 26022771 MLS
Price Improvement! FHA and USDA Loan Eligible! Welcome to 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! Motivated Sellers!

3 Nunnelly Ct, Winchester

127 Bay Hill Dr, Winchester
$249,000
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

15 Kittison 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

527 Hidden Hills Way, Winchester
$219,500
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

405 Nick Ln, Winchester
$280,000
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

130 Winterberry Cir, Winchester
$544,900
5 Beds ⋅ 4 Baths ⋅ 26021642 MLS
Welcome to this beautifully maintained modern home located in the highly sought-after Royal Oaks Estates, perfectly positioned on the edge of Winchester with quick access to shopping, dining, and more. From the moment you step inside, you'll be captivated by the soaring vaulted ceilings in the central great room--an impressive space filled with natural light and designed for both comfort and entertaining. The gourmet kitchen is a chef's dream, offering ample counter space, modern appliances, and a casual dining nook. Just off the kitchen, you'll find a spacious formal dining area, a private home office, and a first-floor primary suite tucked away for peace and privacy. Upstairs, a second primary suite provides additional flexibility--ideal for guests or multi-generational living--along with three more generously sized bedrooms and a full bath. Step outside through elegant French doors to a beautifully landscaped patio and garden area that backs up to a tranquil greenspace--perfect for morning coffee or evening gatherings. The covered front porch offers another peaceful spot to relax and enjoy the neighborhood.

130 Winterberry Cir, Winchester

606 College St, Winchester
$199,900
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

59 Hillcrest Dr, Winchester
$249,000
4 Beds ⋅ 2 Baths ⋅ 26020680 MLS
PRICED TO SELL! 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

2725 Goshen Rd, Winchester
$385,000
3 Beds ⋅ 2 Baths ⋅ 26020495 MLS
Welcome to this one-owner home offering the perfect combination of space, thoughtful updates, and country living! Built in 1996 and situated on 1.67 beautiful acres, this well-maintained 3-bedroom, 2-bath home features 1,344 square feet of comfortable living space with numerous improvements already completed for its next owner. Inside, you'll find updated interior paint, durable LifeProof laminate flooring, beautiful hardwood flooring, and replacement windows (house windows installed in 2021). Pride of ownership is evident throughout, and the home has never had indoor pets. One of the standout features is the impressive 896-square-foot attached garage. With insulated walls, an oversized 8-foot-tall by 18-foot-wide garage door, and a freshly painted interior (2026), this space offers endless possibilities. Whether you need room for oversized vehicles, a workshop, hobbies, or even future finished living space, this garage provides exceptional flexibility. Outside, enjoy the spacious 1.67-acre lot from the newer concrete front porch with handrails and thoughtful landscaping with plenty of shade trees or relax on the concrete back patio added in 2024. The detached 330-square-foot tool shed is equipped with water, electricity, and a 220-volt RV hookup, making it ideal for projects, storage, or RV owners. Major improvements include: • New HVAC system (2009) • Roof replaced (2015) • Vinyl siding and new concrete front porch with handrails (2016) • Garage door opener replaced (2018) • New garage door springs (2020) • Replacement house windows (2021; garage windows excluded) • Updated interior paint and LifeProof laminate flooring (2023) • HVAC professionally serviced (2023) • New concrete back patio (2024) • Garage interior repainted (2026) • Termite treatment maintained and updated • Updated most of the exterior hardware If you've been searching for a move-in-ready home with acreage, a massive insulated garage, an equipped workshop, and a long history of meticulous maintenance by its original owner, this property deserves a place at the top of your list. Schedule your private showing today!

2725 Goshen Rd, Winchester

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