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$489,000
4 Beds ⋅ 4 Baths ⋅ 26022723 MLS
Welcome home to this 4 bedroom, 3.5 bathroom home offering plenty of room to spread out. The open kitchen and living room create a comfortable gathering space, while a separate dining room provides additional space for meals and entertaining. The fully finished basement offers even more living space, including a room with a closet that could provide flexibility for a home office, hobby room or potential 5th bedroom depending on your needs. Step outside to enjoy the nice back deck and fire pit area, perfect for relaxing or entertaining. With versatile living spaces both inside and out, this home offers plenty of room to make it your own. Property is under contract with a 48 hour kick out in place.

1137 Lafayette Blvd, Winchester
$279,500
3 Beds ⋅ 3 Baths ⋅ 26022702 MLS
This house is located within walking distance of Clark County Preschool, Strode Station and Baker and is within minutes of Winchester Bypass and I-64. The house has 3 bedrooms and 2.5 baths and a bonus room on the 2nd floor that would make a great game room or office. The bonus room would also make a nice 4th bedroom. The owner of the house has replaced all of the kitchen appliances and replaced all carpet. The interior of the house has been painted throughout including the garage. The house features a large open great room with a wood burning fireplace. Lots to like about this house; make an appointment today; it could be your new HOME!

304 Newcastle Ln, Winchester
$175,000
3 Beds ⋅ 1 Baths ⋅ 26022678 MLS
Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer to verify all information including schools

24 Spring St, Winchester
$98,500
3 Beds ⋅ 1 Baths ⋅ 26022585 MLS
Well priced and well located, 16 Denny Avenue is conveniently located near Eugene Gay Splash Park, downtown Winchester, shopping and schools. Home features 1152 sq ft with 3 bedrooms, 1 full bath, eat in kitchen and living room. Enclosed porch is located on front of house. Upgrades include laminate flooring, ductless heating and cooling and roof. Property has been tenant occupied and is sold as is. No repairs.

16 Denny Ave, 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
$1,595,000
3 Beds ⋅ 2 Baths ⋅ 26022399 MLS
Welcome to your own slice of Kentucky countryside! Situated on 59.104 picturesque acres, this beautifully maintained 3 bedroom, 2 bath home offers the perfect blend of modern comfort and functional farm living. Built in 2015 with 1,860 sq ft of open-concept living space, the home features soaring ceilings, abundant natural light, a spacious kitchen with oversized island, and a warm, inviting living area ideal for entertaining or relaxing after a day outdoors. The property is thoughtfully equipped for livestock and equestrian use with a horse shed, automatic waterers, multiple fenced areas, 5 additional sheds, and a barn with lean-to for extra storage and shelter. A massive 2,040 sq ft attached garage provides ample room for vehicles, equipment, workshop space, or recreational storage. Whether you're looking for a working farm, horse property, hunting retreat, or peaceful country escape, this property offers endless opportunities with wide-open acreage and beautiful rural views, all while still being conveniently located near town amenities. 4578 Combs Ferry Rd is country living done right.

4578 Combs Ferry Rd Rd, Winchester
$168,000
3 Beds ⋅ 1 Baths ⋅ 26022281 MLS
This inviting 3- bedroom, 1- bath home offers a great combination of comfort, character,and convenience. Beautiful hardwood floors add warmth throughout, while the updated kitchen provides a fresh, functional space for everyday living. Outside, the fenced backyard offers plenty of room for pets, entertaining, gardening, or simply relaxing outdoors. Move in ready and easy to maintain, this home is a wonderful opportunity for anyone looking for value without sacrificing charm.

41 Hiawatha Trl, 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
$140,000
2 Beds ⋅ 1 Baths ⋅ 26022182 MLS
Property includes a detached secondary structure, a 600 sq. ft., 1-bedroom, 1-bath. This structure offers potential for investment use. Property and secondary structure are being sold as-is. Buyer and buyer's agent to independently verify square footage, zoning, permitted use, occupancy requirements, and suitability for buyer's intended purpose.

108 Franklin Ave, Winchester
$724,889
4 Beds ⋅ 5 Baths ⋅ 26022150 MLS
This gorgeous home is a rare find. Perfect for anyone looking for a spacious home with room to grow. The beautiful sunroom overlooks the luxurious in-ground salt water pool. Inside the home you'll find over 4,000 square feet of easy living. A beautiful kitchen with a breakfast nook and bar top, a formal dining area, large living room, a family room with a fireplace, spacious bedrooms, and a partially finished basement with a bathroom.

132 Lana Ln, 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
$282,500
3 Beds ⋅ 2 Baths ⋅ 26022065 MLS
Welcome to 158 Cabin Creek Heights, where comfortable one-level living meets a peaceful country setting just minutes from Winchester! This 3-bedroom, 2-bath ranch offers 1,580 square feet with a functional, easy-flowing layout and plenty of natural light throughout. The spacious primary suite features a walk-in closet and private bath, while the additional bedrooms offer flexibility for guests, a home office, or growing needs. Outside, enjoy nearly half an acre with room to relax, entertain, garden, or simply take in the surrounding rural views. An attached garage adds everyday convenience, and the location offers the quiet feel of country living while keeping Winchester amenities and I-64 within easy reach. A great opportunity for buyers looking for space, simplicity, and a little breathing room!

158 Cabin Creek Hts, 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
$410,000
4 Beds ⋅ 2 Baths ⋅ 26021961 MLS
*Seller has accepted a contingent offer with a 24 hour kickout.* Welcome to this inviting brick ranch in the desirable Stoney Brook neighborhood! Step inside through the foyer, where you'll find a formal dining room and a beautifully updated formal living room featuring fresh paint and wainscoting. The kitchen opens to the cozy living room/den with a masonry fireplace, making it a great space to relax or gather with friends and family. Just off the living area is a climate-controlled sunroom filled with windows and natural light, with direct access to the backyard and semi-permanent fencing. Down the hall are three bedrooms and a full guest bath that has been refreshed with new paint, beadboard and chair rail, plus a spacious primary bedroom with its own private bath. With a mix of hardwood, tile, carpet and vinyl flooring throughout and an attached two-car garage, this home has plenty of space, charm and potential to make it your own!

406 Lynnway Dr, Winchester
$194,900
3 Beds ⋅ 1 Baths ⋅ 26021903 MLS
Welcome to 143 Spruce Court in Winchester! This charming brick ranch offers comfortable one-level living with 3 bedrooms and 1 full bath. Inside, you'll find beautiful hardwood flooring and a warm, inviting layout. Outside, enjoy a well-manicured large corner lot (0.20 ac) with plenty of space to relax or entertain. Conveniently located near a local park featuring a splash park and recreational amenities, this home offers a great combination of comfort, location, and easy living. Schedule your showing today!

143 Spruce Ct, 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
$204,900
3 Beds ⋅ 1 Baths ⋅ 26021864 MLS
Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing convenient space for tools and outdoor equipment. Its desirable location combines privacy with easy access to local shops, dining, and downtown community events. Call today for your private showing. Owner/Agent

38 Mackay Ave, 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
$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
$80,000
1 Beds ⋅ 1 Baths ⋅ 26021134 MLS
Tucked away in a peaceful wooded setting, close to the Kentucky River, this unique property offers privacy, natural beauty, and plenty of potential. The rustic cabin is surrounded by mature trees, native stone, impressive rock formations, and remnants of old stonework that give the property a one-of-a-kind character. Loft bedroom 1 bath Cabin. This property would be great for fisherman or a weekend getaway. Just minutes from the Ky River.

141 Coffee Springs Ln, 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
$324,900
3 Beds ⋅ 2 Baths ⋅ 26005152 MLS
Rare opportunity with TWO lots!! This cozy ranch home, originally built in 1952, but was completely remodeled down to the studs in 2023 (per Seller), offering the charm of an established home with the feel of modern construction. The open concept floor plan features a spacious family room flowing seamlessly into the kitchen, perfect for every day, living and entertaining. The layout provides privacy with two guest bedrooms on one side of the home and the primary suite on the other, complete with a walk-in closet and en-suite bath. Enjoy the outdoors from the covered front porch or the covered pebble rock patio in the back. Property also includes a 2-car detached carport with a large shed behind it for additional storage. Driveway has a perfect place for an RV. Property is just minutes outside of city limits. The second lot offers its own separate driveway, while the current owners have added a new concrete driveway and block wall going to 1291 Muddy Creek. A rare fine with beautiful views, added privacy and extra space. Thanks to the two lots.--don't miss this unique opportunity.

1291-1299 Muddy Creek Rd, Winchester
$258,900
4 Beds ⋅ 1 Baths ⋅ 26021028 MLS
Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready property offers 4 bedrooms, an updated bathroom, a welcoming living room with a decorative (non-working) fireplace, and a cozy den featuring preserved French doors. The foyer leads to a beautifully painted staircase and second floor, while the spacious dining room and kitchen showcase custom painted cabinetry, stainless steel appliances, and a pantry. A large laundry room doubles as a walk-in closet for added convenience. Enjoy relaxing mornings on the wrap-around front porch with brick accents and composite steps, or unwind on the rear sunporch overlooking a vinyl-fenced yard complete with a patio area perfect for a fire pit and a 10X17 shed. The main bedroom is located on the first floor, with three additional bedrooms and a bonus room upstairs. Thoughtful touches like modern fixtures, fresh paint, exquisite wallpaper, and newly painted wood flooring elevate the entire home. With large rear parking and a prime location in the heart of downtown Winchester, you'll be within walking distance to local shops, dining, and upcoming festivals. The current owner will surely miss the convenience and wonderful neighbors and is confident the next owners will fall in love just as deeply. This is one you have to see! ONE year home warranty to buyer at closing.

162 French Ave, Winchester
$66,000
2 Beds ⋅ 2 Baths ⋅ 26020744 MLS
This 2 bedroom 2 bath home is perfect for an investor or a family looking for a nice home. All new flooring throughout. New bathroom sinks and commodes. The home backs up to the community park. It is located just minutes from Hamburg or the Winchester Bypass.

546 Constitution Dr, 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
$536,000
3 Beds ⋅ 3 Baths ⋅ 26019672 MLS
Welcome to this beautifully designed 3-bedroom, 2.5-bath ranch in the highly sought-after Earlymeade subdivision, where comfort, style, and exceptional efficiency come together. This spacious one-story home offers an open, inviting floor plan highlighted by a stunning floor-to-ceiling stone fireplace that anchors the expansive great room. The well-appointed kitchen features granite countertops, abundant workspace, and flows seamlessly into the living area—perfect for everyday living and entertaining. Throughout the home, you'll appreciate having no carpet, providing a clean, modern look that's both stylish and easy to maintain. What truly sets this home apart is its impressive investment in energy efficiency. Enjoy year-round comfort with a geothermal heating and cooling system, while solar panels paired with a Tesla battery backup help reduce energy costs and provide added peace of mind during power outages. Start your mornings on the covered front porch and relax in the evenings on the covered back porch, overlooking a beautiful greenspace with no rear neighbors directly behind you. Offering the perfect blend of quality construction, modern finishes, and cutting-edge energy-saving technology, this exceptional ranch is a rare opportunity in one of Winchesters most desirable neighborhoods.

267 Runnymeade Dr, 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
$2,299,000
5 Beds ⋅ 5 Baths ⋅ 26020418 MLS
This 5 Bedroom, 5 Bathroom home is quietly located in the highly desired Combs Ferry area of Clark County. Location is evident as you are minutes to Hamburg Lexington as well as Winchester and Richmond. This complete custom home was constructed in 2022. The 6284 sqft boasts custom features including built in appliances, in-ground oversized heated pool with outdoor bathroom, decorative ceilings, custom trim and built ins, finished basement, home gym, movie theatre, basement bar, Large walk-in closets attached to ALL bedrooms, basketball court, shooting range, detached garage with concrete floors and double garage bays. This list is endless. There is an additional 1545 sqft of unfinished space that new buyer can easily customize. Schedule your showing today and view this breathtaking property! Seller is a licensed Realtor in state of KY.

5039 Combs Ferry Rd, Winchester
$475,000
3 Beds ⋅ 2 Baths ⋅ 26020298 MLS
Beautiful all brick ranch home on 4.1 acres that has 3 bedrooms, 2 bathrooms, open concept floor plan, large stone fireplace with wood burning stove & blower. Kitchen has butcher block countertops, garbage disposal, pot filler, range hood, ample cabinets with large pantry cabinet & island. Large primary suite that includes a walk-in tiled shower, with 2 shower heads, has a place for soaking tub with easy access for hooking up, 2 vanities, toilet closet and large closet with lots of built-in shelving. Easy access to laundry room which is right off of the garage and connects to primary suite. Family room has bar sink and overlooks a beautiful view of the secluded wooded backyard and has 3 French doors and 2 atrium doors to access back deck. Home has Pella windows and doors that are triple lock and Bryant Smart Home Wi-Fi thermostat & MyQ garage door opener app opens and closes garage door from anywhere. Large 2 car garage with mechanical room. Only 5 minutes from Mountain Parkway and 45 minutes to Toyota in Georgetown. Schedule your showing today!

625 Pine Ridge Rd, Winchester