Winchester Real Estate | Winchester Single Family Homes for Sale

Really Nice all Brick 3 bedroom, 1 Bath Ranch with large garage and a fully enclosed covered back patio in desireable Colonial Valley Neighborhood. Low Electric bills, HVAC 2 years old, Water Heater 3 years. Most comparable homes in this neighborhood don't have a garage or enclosed porch. Picture of Range and refrigerator are for illustration only. Seller will give a $1,000 allowance for appliances

117 Colonial Park Dr, Winchester

$285,000

3 Beds ⋅ 2 Baths ⋅ 26029425 MLS

Enjoy Southern living in this charming Cape Cod-style home featuring three bedrooms, two full bathrooms, and a dedicated office. The main level includes the primary bedroom, office, full bathroom, laundry room, and a kitchen with a breakfast bar and dining area. Upstairs are two additional bedrooms and a second full bathroom. A spacious, level yard provides plenty of room for entertainment. Come enjoy today.

307 Mcdowell Dr, Winchester

$249,000

3 Beds ⋅ 2 Baths ⋅ 26029418 MLS

This charming Cape Cod home is tucked away in an established Winchester neighborhood only 14 miles to Hamburg and less than 5 minutes to I64. You will love the short walk to Legacy Park! Yes, it does have a 1st floor Primary bedroom. This cute home has lots of character throughout with a spacious living room and an inviting dining room. The roof is only 2 years old; the heating and cooling has been well maintained, and the exterior of the home has been recently painted. The upstairs area offers 2 additional bedrooms and a full bathroom. The basement has additional storage space and a laundry area. There is so much private outdoor space to enjoy! The huge backyard is fenced and backs up to greenspace. There is a large patio perfect for friends and family gatherings. If you need extra storage space, you will enjoy the detached 2 car garage for all your outdoor toys. For convenience the property also has two separate driveways. Don't wait on this one! Schedule your private tour today.

48 Bon-Haven Ave, Winchester

$56,700

3 Beds ⋅ 1 Baths ⋅ 26029234 MLS

INVESTMENT OPPORTUNITY — BUILD YOUR VISION! The existing home is in poor condition and may be suitable for renovation or a tear-down project. The property consists of almost 1/2 Acre (.45 acre) with a newer metal building 20 X 25. An excellent opportunity for investors, builders, or buyers looking to create something new! This could be an excellent place for storing equipment, boats, RVs, or other recreational toys! 1,000-gallon septic system installed in 2023.

121 Ralston Ln, Winchester

$519,900

5 Beds ⋅ 3 Baths ⋅ 26029059 MLS

*Owner Agent Welcome to this spacious 2023-built, manufactured home situated on 6.54 beautiful acres in Winchester, Kentucky. Offering 5 bedrooms and 3 full bathrooms, this home provides plenty of space for family, guests, and comfortable everyday living. The property combines the convenience of a newer home with the beauty and privacy of acreage. The land features a natural spring, adding a unique country-living feature and providing an additional natural water resource on the property. A detached one-car garage provides valuable space for parking, storage, hobbies, or a workshop. With 6.54 acres, there's plenty of room to enjoy the outdoors, garden, hobby farm, animals such as horses, goats, chickens or turkeys, have recreational space, or simply take in the peaceful surroundings. The property also offers very limited restrictions. The only known restriction is that no obstruction may be placed across the easement located along the rear of the property such as gate, fence etc., giving the new owner considerable flexibility in enjoying and utilizing the land. If you've been searching for a newer 5-bedroom home on acreage with a natural spring, detached garage, privacy, and limited restrictions, this property offers a rare combination of features in the Winchester area. Within 20 minutes of Richmond and 30 minutes of Lexington. Driveway easement at very rear of property. Utility easement for water through property with water meter near road. LISTING AGENT OWNS PROPERTY

7440 Bybee Rd, Winchester

$439,900

3 Beds ⋅ 2 Baths ⋅ 26028916 MLS

Welcome to 119 Winterberry Court! Offered at $439,900, this beautiful all-brick home is situated on a spacious corner lot and offers 3 bedrooms, 2 full bathrooms, and 2,276 square feet of living space, including the finished sunroom! Step inside to find beautiful hardwood flooring, an inviting open-concept living area, and a spacious kitchen featuring granite countertops, stainless steel appliances, abundant cabinetry, and a large island perfect for entertaining. The primary suite offers a tray ceiling and a beautifully remodeled bathroom complete with a custom tiled walk-in shower, double vanity, and generous closet space. One of the home's standout features is the finished sunroom, complete with its own mini-split heating and cooling system, providing a comfortable space to enjoy year-round! Outside, you'll find a fenced backyard, patio area, mature landscaping, and a two-car attached garage. This home has seen numerous improvements since 2019, including a new roof, replacement of all windows, two new garage doors and openers, remodeled bathrooms, a new fence, and 6-inch gutters. Additional improvements include professional crawlspace encapsulation in 2025 (see listing attachments for full details) and a brand-new HVAC system installed in 2026! Conveniently located less than half a mile from the interstate and approximately 20 minutes from both Hamburg and Paris, this home offers the perfect combination of space, updates, and accessibility. Schedule your private showing today!

119 Winterberry Cir, Winchester

$299,900

3 Beds ⋅ 2 Baths ⋅ 26028838 MLS

This stunning remodeled 3 bedroom 2 bathroom all brick ranch in Verna Hills subdivision is a must see! From the moment you walk in, your only concern is moving in. The following items have been done: new drywall in 50%+ of the home done to completely remove all wallpaper, new roof, soffit, gutters (2025), new hot water heater, new custom back sliding glass door, crawlspace completely waterproofed with vapor barrier and newly installed sump pump, brand new privacy fence, all new vinyl flooring and paint, completely upgraded kitchen with custom cabinetry, backsplash, quartz countertops, and stainless steel appliances, 2 custom designed bathrooms with custom tile and trim work and all new custom light fixtures. Schedule a showing soon to see this great home!

314 Botts Ct, Winchester

$250,000

3 Beds ⋅ 2 Baths ⋅ 26028494 MLS

Welcome to 13 Euclid, a rare find that keeps the original charm of an older downtown home without the upkeep that usually comes with one. This beautiful one-level, 3-bedroom, 2-bath home still has its character, including soaring 12-foot ceilings and original features. Both full bathrooms have been updated, and a fresh neutral color palette runs throughout. Most importantly, the systems and functional items have been updated, allowing for a more maintenance-free lifestyle, which is truly rare in an older home. The home has a dimensional shingle roof, HVAC, water heater, and sewer line that have all been updated within the past five years. The crawlspace vapor barrier and extra attic insulation were updated as well. Low-maintenance white vinyl siding and 200-amp electrical service complete the impressive improvements. A covered front porch welcomes you into the formal foyer, which is flanked by two bedrooms. One is currently used as a sitting area. From the foyer, you'll flow into the living room and adjacent dining room. Just off the dining space, the primary bedroom has a large closet and a private bath. The spacious kitchen is the heart of the home, equipped with all appliances, and a perfect setting for holiday meals. A home office is ready for working from home, and a mudroom and a large laundry room/pantry add everyday convenience. Step outside to the park-like backyard, which is fully fenced with large mature trees, a wide gate, and a parking pad. It's a gardener's dream, with daffodils, tulips, hyacinths, daylilies, and more blooming through the seasons. Park off the rear lane behind the home or on the street out front for easy access. Please note: All updates per seller, and there are 3 beautiful fireplaces in the home for aesthetic purposes only (non-functional).

13 Euclid Ave, Winchester

$617,000

3 Beds ⋅ 4 Baths ⋅ 26028684 MLS

If you're looking for space, character, and a home with plenty of possibilities, this one deserves a look! This beautiful ranch-style home offers a full basement, two garages, and an inviting floor plan with impressive architectural details throughout. Step inside and you'll immediately notice the gorgeous hardwood flooring, detailed trim work, and spacious living areas. The great room features a vaulted ceiling, brick fireplace, and beautiful custom built-in cabinetry. The kitchen offers an abundance of rich wood cabinetry, granite countertops, stainless steel appliances, double ovens, and a breakfast area. A formal dining room showcases elegant wainscoting, crown molding, and a beautiful chandelier, adding character and charm. The screened-in porch provides another great space to relax and enjoy the outdoors. The full basement offers additional space and flexibility, while the two garages provide plenty of room for vehicles, storage, or hobbies. With its generous living spaces, beautiful woodwork, and thoughtful design, this home has so much to offer. Come see the possibilities for yourself! Rony Jo Ballou Broker Auctioneer.

131 Teal Ln, Winchester

$424,500

5 Beds ⋅ 4 Baths ⋅ 26028682 MLS

You have to see this one! Spacious 5-bedroom, 4-bath home priced under recent appraisal! The primary bedroom and two other bedrooms are on the main level. This wonderful home sits on a large lot with a great backyard perfect for entertaining, play and relaxation. Conveniently located close to the Winchester bypass and shopping, you'll enjoy easy commutes and everyday errands. The basement offers flexible space for so much more- think game room, home office, gym, or all three. Plus, a separate garage keeps the lawnmower and yard equipment neatly out of the way. With generous living space throughout, this home truly offers room for everyone. Don't miss this fantastic value in a prime location- schedule your showing today.

323 Skylark Dr, Winchester

$457,900

4 Beds ⋅ 3 Baths ⋅ 26028668 MLS

***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** The Paddock offers approximately 1,986 square feet of thoughtfully designed main-level living with 3 bedrooms, 2.5 baths and a versatile flex room suitable for a home office or optional fourth bedroom. The open kitchen, dining and great-room layout features 10-foot ceilings, bar seating and an expanded walk-in pantry. A private primary suite includes a spacious walk-in closet and well-appointed bath, while two additional bedrooms and a second full bath provide comfortable accommodations for family or guests. Covered front and rear outdoor spaces and an attached 2-car garage complete the main level. The home is planned over an unfinished walkout basement, providing excellent storage and future finishing potential, with plumbing stubbed for a future basement bath. Floor plan, square footage, finishes and construction details are subject to final plans, specifications and selections. Images are conceptual renderings.

200 Evergreen Dr, Winchester

$513,600

3 Beds ⋅ 2 Baths ⋅ 26028669 MLS

***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** The perfect combination of style, comfort, and quality craftsmanship in the Run for the Roses floor plan. This thoughtfully designed ranch home offers an open-concept layout with spacious living areas, a split-bedroom floor plan, and upgraded finishes throughout. The heart of the home features an expansive great room that flows seamlessly into the dining area and beautifully designed kitchen, complete with a large center island, abundant cabinetry, and a walk-in pantry creating the ideal space for everyday living and entertaining alike. The private primary suite is designed as a true retreat, offering a spacious bedroom, luxurious ensuite bath with dual vanities, soaking tub, separate shower, private water closet, and an oversized walk-in closet with direct access to the laundry room for added convenience. On the opposite side of the home, two generously sized guest bedrooms share a full bath, providing privacy and flexibility for family, guests, or a dedicated home office. Need more space? This home is built on a full unfinished walkout basement, offering incredible potential to nearly double your living area. Whether you envision additional bedrooms, a family room, home theater, fitness space, workshop, or simply exceptional storage, the lower level is ready to be customized to fit your lifestyle. Outside, enjoy a welcoming covered front porch and an attached two-car garage, while the proposed construction gives you the opportunity to personalize many of the home's finishes and selections to make it uniquely yours. If you've been searching for the perfect blend of modern design, functional living space, and room to grow, the Run for the Roses is a home you won't want to miss. Pricing and specifications are subject to final plans, selected options, and lot availability. Photos and renderings are for illustrative purposes only and may depict optional features or upgrades not included in the base price.

220 Evergreen Dr, Winchester

$469,925

3 Beds ⋅ 2 Baths ⋅ 26028670 MLS

***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** Discover the perfect blend of timeless design, modern comfort, and future expansion potential in The Mulberry, a thoughtfully designed ranch home offering well-appointed main-level living plus a full unfinished walkout basement ready for your personal vision. The open-concept floor plan is designed for both everyday living and entertaining, featuring a spacious Great Room with a gas fireplace, a bright dining area, and a beautifully designed kitchen complete with a large center island, walk-in pantry, abundant cabinetry, and dedicated oven/microwave wall cabinet. The adjoining rear covered porch extends your living space outdoors, creating the perfect setting for relaxing or entertaining while overlooking your backyard. The private primary suite serves as a peaceful retreat with a generous walk-in closet, dual vanity, oversized walk-in shower, soaking tub, and convenient access to the laundry room through the owner's hall. On the opposite side of the home, two additional bedrooms, a full bath, and a dedicated office provide comfortable accommodations for family, guests, or working from home.

225 Evergreen Dr, Winchester

$462,738

3 Beds ⋅ 2 Baths ⋅ 26028671 MLS

***TO BE BUILT, NO CONSTRUCTION HAS STARTED*** Experience the perfect blend of modern farmhouse style and peaceful country living with The Equestrian floor plan, a beautifully designed proposed new construction home in the desirable Locust Hill Acres subdivision. This thoughtfully crafted ranch floor plan features 3 bedrooms, 2 full baths, and an open-concept design ideal for both everyday living and entertaining. The home also includes an unfinished walkout basement, offering incredible flexibility for future expansion, additional living space, a recreation room, home gym, workshop, or abundant storage. The spacious great room flows seamlessly into the dining area and chef-inspired kitchen, complete with a large center island, pantry, abundant cabinetry, and premium finishes throughout. The private owner's suite serves as a relaxing retreat with a generous walk-in closet and a luxurious ensuite bath featuring dual vanities and a tiled walk-in shower. Two additional bedrooms provide comfortable accommodations for family, guests, or a dedicated home office. Step outside to enjoy the oversized cathedral-ceiling covered rear deck, perfect for entertaining or taking in the peaceful surroundings of your one-acre homesite. A welcoming covered front porch with exposed timber accents and a charming breezeway connecting the home to the detached two-car garage adds timeless character and exceptional curb appeal. Enjoy the tranquility of rural living while remaining just minutes from downtown Winchester and an easy commute to Lexington. Pricing and specifications are subject to final plans, selected options, and lot availability. Photos and renderings are for illustrative purposes only and may depict optional features or upgrades not included in the base price.

230 Evergreen Dr, Winchester

$325,000

5 Beds ⋅ 3 Baths ⋅ 26028567 MLS

Distinctive character, generous space, and a convenient location near downtown Winchester! This five-bedroom, three-bath brick home offers room to spread out, with flexibility for guest rooms, a home office, or hobbies. Eye-catching architectural details and an inviting front porch give the home memorable curb appeal. With downtown shops and dining nearby, 25 W. Hickman Street combines the appeal of an established neighborhood with everyday convenience. Schedule your private showing and picture your next chapter here! Property can be used as residential or office space.

25 W Hickman St, Winchester

$255,000

3 Beds ⋅ 1 Baths ⋅ 26028523 MLS

Convenient, comfortable, and ready for its next owner! This 3-bedroom, 1-bath ranch home is located in the heart of Winchester and offers easy one-level living with a low-maintenance floor plan. Inside, you'll find comfortable living spaces with freshly cleaned carpets and a home that's ready to move into and make your own. A newer roof provides added peace of mind, while the fenced backyard offers plenty of space for pets, kids, entertaining, or simply enjoying the outdoors. One of the property's best features is the detached 2-car garage with electric, providing excellent space for parking, storage, a workshop, or hobbies. With its central Winchester location, fenced backyard, oversized garage space, and manageable one-level layout, 26 Holiday Road is a great opportunity for a first-time buyer, someone looking to downsize, or anyone searching for an affordable, low-maintenance home. Schedule your private showing today!

26 Holiday Rd, Winchester

$4,895,000

3 Beds ⋅ 4 Baths ⋅ 26028325 MLS

A Rare 77 ± acre Kentucky Estate with a new custom home & equestrian facilities offers privacy, commanding views, and the natural beauty of Kentucky's renowned horse country that truly define this exceptional recreational estate. Offering an extraordinary combination of luxury living, equestrian amenities and recreational opportunities, the property has been thoughtfully designed to provide both functionality and tranquility. The setting is simply spectacular, with Nursery Place Thoroughbreds and Harkness Edwards Winery as immediate neighbors, placing this estate in an impressive equestrian environment just minutes from Fayette County. A winding private drive passes the beautiful stocked ponds, leading to the highest point of the estate where an impressive custom stone residence and equestrian facility command panoramic views. The recently completed 5,800 ± square-foot custom 3 BR/3.5 BA stone manor home combines elegant finishes with a warm aesthetic. Features include rustic boxcar-wood flooring, a custom kitchen with granite center island and countertops, Wolf and Sub-Zero appliances and custom cabinetry. The spectacular great room provides generous space for both living and dining, highlighted by a floor-to-ceiling stone fireplace and an expansive wall of windows framing remarkable views of the surrounding countryside. Both the great room and first-floor primary suite open onto a massive covered deck featuring an outdoor fireplace and hot tub—an exceptional setting for entertaining or simply enjoying the serenity of the property. The private main floor primary suite includes its own fireplace, luxurious en suite bath, large walk-in closet, convenient laundry area, and private office. A beautiful stone entrance foyer leads to a loft overlooking the great room. The walkout lower level features 2 additional spacious bedrooms and an open family room, with direct access -through the walkout doors- to the impressive in-ground swimming pool. Adding another dimension to the estate is the remarkable barndominium which includes approx 1,000 sf of living quarters featuring 1 bedroom and 1½ baths. The clear-span main building is designed for extraordinary versatility- capable of accommodating aircraft, collector cars, RVs, and/ or other recreational vehicles. Impressive hydraulic doors and extra-tall ceilings provide easy access. Inside, rustic barnwood finishes create a warm and inviting atmosphere ideal for entertaining, gatherings, or displaying a collection. A substantial wood shop with additional storage extends along the edge of the building. The lower level incorporates a substantial barn area with 4 horse stalls, tack room, hay storage, and tractor/mower storage, with convenient access to the 10-acre fenced field for horse turnout. Whether envisioned as a private equestrian estate, recreational compound, luxury country residence or a combination of all three, this property offers a rare level of amenities and versatility in one of Central Kentucky's most desirable settings- it truly must be seen to be appreciated.

5825 Combs Ferry Rd, Winchester

$197,000

3 Beds ⋅ 1 Baths ⋅ 26028269 MLS

Welcome to 214 Center Drive! Tucked away at the end of a cul-de-sac, this charming 3-bedroom, 1-bath ranch offers a peaceful setting with convenient access to the interstate. Step inside to discover a functional floor plan featuring a spacious living area and an eat-in kitchen. Just off the kitchen, a versatile bonus room offers endless possibilities like a home office. The bathroom features a double vanity, providing extra counter space and convenience. Outside, enjoy a back deck overlooking a tree-lined backyard with neighboring farmland. A freshly paved driveway adds to the home's curb appeal, while the attached storage area, formerly a one-car garage, provides plenty of room for tools, lawn equipment, and more. Some rooms are virtually staged to showcase layout.

214 Center Dr, Winchester

$299,900

5 Beds ⋅ 4 Baths ⋅ 26028226 MLS

*****PRICED BELOW APPRAISAL & MOTIVATED SELLERS***** Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for multi-generational living, rental income opportunities, or for a great work setup. Opportunity with unlimited potential.

410 W Lexington Ave, Winchester

$265,000

3 Beds ⋅ 2 Baths ⋅ 26028125 MLS

Welcome home to this charming, move-in ready brick ranch in a quiet low-traffic neighborhood. Perfectly located within walking distance of historic downtown Winchester, College Park, the Public Library, and four local parks, this 3-bedroom, 2-bath gem offers convenience and community. Step inside to find newly refinished hardwood floors and smooth ceilings -- no carpet here for easy, low-maintenance living! Enjoy a bright, sunlit living space thanks to a newly replaced bay window, plus a cozy fireplace for chilly evenings. The home features a newly tiled den, a fully renovated second bathroom, and the kitchen equipped with stainless steel appliances (including a gas stove). Recent updates give you ultimate peace of mind, including a newly sealed driveway, brand new LB stackable washer and dryer and some modern finishes throughout the home. Outside the fenced backyard boasts a patio tucked away for privacy in hosting friends and family. With easy access to I-64 and Lexington Avenue, commuting is a breeze. Call and schedule your showing today!

122 Sunset Hts, Winchester

$2,299,000

5 Beds ⋅ 4 Baths ⋅ 26028074 MLS

Experience exceptional craftsmanship, privacy and resort-style living on over 12 acres in the highly desired Combs Ferry area of Clark County. Quietly tucked away yet conveniently located just 15 minutes from Hamburg in Lexington, as well as Winchester and Richmond, this extraordinary custom home was built in 2022 and offers 6,284 finished square feet, plus an additional 1,545 square feet of unfinished space ready for the next owner to customize. From the moment you enter, the quality and attention to detail are unmistakable. Andersen 400 Series windows and doors, decorative ceilings, custom trim and built-ins, engineered hardwood flooring, quartz countertops and designer lighting are featured throughout. The spacious kitchen is a true centerpiece, showcasing custom cabinetry, soft-close doors and drawers, under-cabinet lighting, a hidden walk-in pantry, double ovens, built-in microwave and a 5-burner gas range with built-in Thermador appliances. The main-level primary suite is a private retreat, complete with decorative beams, a stacked-stone gas fireplace, double vanities, soaking tub, expansive walk-in closet and an oversized tiled pass-through shower featuring dual shower heads and a centered rain head. Large walk-in closets accompany every bedroom, providing exceptional storage throughout. The finished lower level expands the possibilities with a home gym, dedicated movie theater with projector and equipment, home office/bonus room, wet bar with granite countertops, wine and beverage refrigerators and dishwasher, plus an additional bedroom with egress window, full bathroom, and walk-in closet. Multiple unfinished areas and the additional 1,545 square feet provide tremendous potential for future customization. Step outside and discover your own private entertainment destination. The 45,000-gallon oversized heated chlorine pool features a tanning ledge, deep-end swim ledge, fountain, LED lighting and energy-efficient variable-speed pump. Enjoy evenings around the custom outdoor fireplace, with the convenience of a dedicated outdoor bathroom. The property also includes a basketball court, shooting range, and detached garage with concrete floors and double garage bays. Additional thoughtful features include a formal dining room with custom moldings, laundry room with built-in cabinetry, mudroom/drop zone with built-ins and cubbies, spray foam insulation, three all-electric HVAC systems, and two 60-gallon water heaters. This is far more than a home; it is a custom-built private estate designed for everyday luxury, entertaining, recreation and relaxation, with room to make it uniquely your own. The combination of acreage, exceptional construction, extensive amenities and convenient location is truly rare. Schedule your private showing today and experience this breathtaking property firsthand. Seller is a licensed Realtor in Kentucky.

5039 Combs Ferry Rd, Winchester

$199,900

3 Beds ⋅ 1 Baths ⋅ 26028060 MLS

Check out this beautifully remodeled 3-bedroom, 1-bath home offering comfortable living and a convenient location within walking distance of the playground! Whether you're looking for your next home or an investment opportunity, this property has plenty of potential. The home is currently tenant-occupied, with the tenant leaving on 11/20/26 A minimum of 48 hours' notice is required for all showings. Please plan accordingly when scheduling your visit. Don't miss the opportunity to see what this property has to offer!

520 College St, Winchester

$289,900

3 Beds ⋅ 2 Baths ⋅ 26028007 MLS

Charming Brick Ranch with Beautiful Outdoor Living! Welcome home to this inviting brick ranch offering timeless charm, comfortable living, and plenty of space to make your own! Featuring 3 bedrooms, 2 full bathrooms, and a full walk-out basement, this home offers a versatile layout with endless possibilities. Enjoy the warmth and character of the mature trees surrounding the property, along with a covered front porch that creates the perfect welcome. The screened-in porch provides an ideal spot to enjoy your morning coffee, unwind in the evenings, or entertain family and friends while taking in the peaceful outdoor setting. Inside, you'll find granite countertops and fresh paint that give the home a clean, refreshed feel. A brand-new roof adds extra peace of mind for the next owner. With classic brick construction, inviting outdoor spaces, and a full walk-out basement offering additional potential, this property is a wonderful opportunity to find the comfort, charm, and space you've been looking for. Don't miss your chance to make this home your own!

47 Cherokee Ct, Winchester

$309,900

4 Beds ⋅ 3 Baths ⋅ 26027910 MLS

This 4 bedroom, 3 bath home is quietly nestled within the Colby Ridge subdivision just off Bypass road. Updates can be seen throughout. Spacious great room, open living/ kitchen areas, large master bedroom with on-suite and walk-in closet, fully fenced yard and so much more. Schedule your showing today!

444 Wellington Way, Winchester

$639,000

3 Beds ⋅ 1 Baths ⋅ 26027905 MLS

Possibilities Galore! This beautiful 3 bedroom brick home comes with 18 acres of land, a tobacco barn, and a 4700 square foot building. It is a prime location on the Clark and Montgomery County line. The huge building could be used for lots of things. It has electric and water. Come grab on to this great opportunity while it last.

9930 Mount Sterling Rd, Winchester

$220,000

3 Beds ⋅ 1 Baths ⋅ 26027559 MLS

Charming, move in ready 3-bedroom home just minutes from downtown Winchester! This inviting home features LVP flooring throughout, beautiful granite countertops, and a practical layout that makes everyday living easy. With three bedrooms and a full bath, there's plenty of space to make it your own. Enjoy the convenience of being close to downtown Winchester, local dining, shopping, and everything the community has to offer. Come see all this place has to offer and discover your next place to call home!

15 Maryland Ave, Winchester

$265,000

5 Beds ⋅ 4 Baths ⋅ 26027497 MLS

Welcome home to this spacious two-story residence offering plenty of room for family and guests. Featuring 5 bedrooms and 3 bathrooms, this home provides a comfortable and versatile layout with generous living space throughout. Beautiful wood floors add warmth and character, while the tile bathrooms offer durability and easy maintenance. Enjoy the charm of the front porch and inviting sunroom, perfect for relaxing or enjoying your morning coffee. The home also features new concrete patios in both the front and back, providing great outdoor spaces for entertaining, relaxing, or enjoying time with family. Conveniently located near Main Street, with easy access to local shops, restaurants, and amenities. A spacious home with character, comfort, and plenty of room to make it your own! Buyer to verify all aspects of the home, including exact square footage and schools!

109 5th St, Winchester

$200,000

3 Beds ⋅ 1 Baths ⋅ 26027397 MLS

213 E Broadway St, Winchester

$359,900

4 Beds ⋅ 2 Baths ⋅ 26027372 MLS

Built in 1913 and located two blocks from Main Street, 107 S Burns Avenue retains its original interior detail: coffered ceilings, cherry wood wainscoting, hardwood floors, leaded diamond-pane windows, brick fireplaces with their original mantels, and built-ins throughout. The home offers four bedrooms, two full baths, and 2,352 square feet. The upper level has been fully renovated and includes a private fourth bedroom, full bath, built-in workspace, generous knee-wall storage, and a dedicated heating and cooling system. In the kitchen, custom cabinetry complements an original double-drainboard cast-iron sink, while the main-level bath retains a beautifully reglazed original clawfoot tub. Outdoors, an eight-foot privacy fence creates a secluded backyard setting with an above-ground pool and ample space for relaxing and entertaining. An original carriage-door garage adds another layer of historic character, complemented by off-street parking for up to three vehicles. Located just two blocks from Main Street, the home offers convenient access to downtown Winchester's locally owned restaurants, boutiques, theater, festivals, and community events. College Park and the public library are also just a few blocks away.

107 S Burns Ave, Winchester

$439,000

3 Beds ⋅ 3 Baths ⋅ 26000113 MLS

This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

42 Mockingbird Valley Rd, Winchester

$299,900

3 Beds ⋅ 2 Baths ⋅ 26027106 MLS

Welcome to one of Winchester's best-kept secrets! This beautifully updated 3-bedroom home is truly move-in ready and packed with upgrades inside and out. From the moment you arrive, the beautifully landscaped yard sets the tone for what's waiting inside. Thoughtful updates throughout give the home a fresh, modern feel, while a new roof provides added peace of mind. Step outside and enjoy the large fenced backyard, offering plenty of room for entertaining, pets, play, or relaxing in your own private outdoor space. And it's the little extras that make this home stand out—even the bathroom features Bluetooth connectivity for an added touch of modern convenience! With upgrades around every corner and all the work already done, this is the kind of home you can simply move into and enjoy. Stylish, updated, and full of unexpected extras—this Winchester gem may not stay a secret for long!

8 Monroe Ave, Winchester

$769,900

3 Beds ⋅ 3 Baths ⋅ 26026365 MLS

Beautiful custom home built in 2024 with high-end upgrades throughout. Surrounded by mature trees on over 3 acres with mountain views, this home offers a beautiful mix of privacy, quality, and convenience. From the moment you walk up, you can see the quality of craftsmanship. A large front porch welcomes you with double front doors. Once inside, you're immediately drawn to the soaring ceilings, wood-planked ceiling, wall of black-framed windows, and abundant natural light. The open loft overlooking the great room adds to the unique design and makes the space feel even more impressive. The quality and craftsmanship throughout this home truly stand out and are increasingly hard to find in today's market. You'll find solid wood doors, engineered hardwood floors, custom cabinetry, quartz countertops, designer lighting, and thoughtful details throughout. The primary suite is located on the first floor and features a large walk-in closet and spa-like bathroom. The primary bath includes a beautiful marble tile wet room and freestanding soaking tub, creating a relaxing retreat. The setting is one of the things that makes this property so special. Mature trees surrounding the home give it a peaceful, private feel while still keeping you within an easy drive of Lexington. Outdoor living is just as impressive, with approximately 815 square feet of covered porches, including a screened porch accessible directly from both the primary bedroom and great room. It's the perfect place for morning coffee, quiet evenings, or gatherings with friends. The home is just 1.5 miles from Exit 10 on the Mountain Parkway, approximately 29 minutes from Hamburg Pavilion, 22 minutes from the Red River Gorge, and about 19 minutes from Kroger in Winchester. The oversized 24x30 garage, built in 2026, provides plenty of room for vehicles, storage, a workshop, or recreational equipment. Outside, the 3+ acre lot offers plenty of room to enjoy the property as it is or create your own outdoor space, with room for a future pool and entertaining area. If you've been looking for a newer home with acreage and privacy without feeling too far removed from everything, this is one you'll want to see. If you're tired of seeing the same cookie-cutter homes, this one is refreshingly different. The home has even been selected by Architectural Designs to be featured in a client album on their website.

330 Spencer Ln, Winchester

$1,125,000

3 Beds ⋅ 4 Baths ⋅ 26026878 MLS

Tucked away behind private gates on 28 beautiful acres, this one-of-a-kind cabin offers the perfect blend of privacy, luxury, and country living. Step inside to a stunning open-concept living, dining, and kitchen area designed for gathering and entertaining. The kitchen is a showstopper with custom cabinetry, quartz countertops, a waterfall island, top-of-the-line appliances, and a spacious walk-in pantry. Off the kitchen on the right wing of the house there is a mudroom area with half bathroom, followed by the primary suite. The main-level primary suite is a true retreat, very spacious bedroom area with a private sunroom and direct access to the patio and in-ground pool, walk-in closet and laundry closet. The bathroom features a soaking tub and a tiled walk-in shower. Upstairs, you'll find an additional spacious bedroom with built-in bunk beds, a walk-in closet, and full bath. The left wing of the home provides ideal in-law or guest quarters featuring its own kitchen, open concept living and bedroom area with fireplace, walk-in closet, full bath with walk-in shower, and private exterior entrance. Outside is where this property truly sets itself apart. Enjoy your own private oasis with an in-ground pool surrounded by picturesque acreage. The backyard also includes a "she shed" currently used as a workout room, chicken coop, run-in shed, and 30x33 detached garage. This property features an AKC-inspected kennel facility with 14 indoor/outdoor runs, an office, a grooming area, a bathing area, an open work space, half bathroom and a fenced exercise area. Another 6-hole kennel with overhangs. The remaining property features 7 paddocks, 5 run-in sheds, multiple fenced pastures with run-in sheds and water. Bring the horses, cows, dogs—and even the in-laws! This is an animal lover's dream with room to live, work, play, and enjoy the peace of the countryside, all while being just minutes from I-64 and approximately 24 minutes from Downtown Lexington. The possibilities for this property are endless, and it is a truly special property that has to be experienced in person!

2100 Irvine Rd Unit 40391, Winchester

$215,000

3 Beds ⋅ 1 Baths ⋅ 26026596 MLS

This brick ranch offers three bedrooms, a full bath and luxury vinyl flooring throughout. The spacious living room opens into the kitchen, and the unfinished basement gives you plenty of extra room for storage with space to use however you need it. Sitting on a corner lot, this home is a great option for anyone looking for an affordable home with room to make it their own. Plus, you're close to shopping and restaurants and just a few minutes from I-64 for an easy commute.

14 Shelley Dr, 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

$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

$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

$675,000

4 Beds ⋅ 4 Baths ⋅ 26026085 MLS

Rare opportunity to purchase a new construction home in the country on almost 5 acres in Clark County! Brand new modern farmhouse featuring 4 bedrooms, 3.5 baths, front and rear covered porches with stamped concrete floors and stained wood ceilings, 2 car garage, gas vented fireplace, and much more! From the inviting high vaulted ceiling foyer you will notice the tray ceilings with faux beams in the formal dining area and the spacious great room, which leads to the functionally designed kitchen and pantry. Enjoy the privacy of a secluded main-level en-suite bedroom, thoughtfully positioned away from the homes primary living spaces. The spacious bath offers a soaking tub, tiled shower, separated dual vanities, access to the massive upscale dual access laundry room, and windows with a beautiful view! Up the stairs above the garage you will find another private bedroom with full bath. The opposite side of the home contains 2 more bedrooms with a full bath between. It is truly a perfect layout to maximize the use of every square foot! Other features include LP smart siding, quality stainless appliances including a lower cabinet microwave, custom vented range hood, under cabinet lighting, disposal, quartz countertops throughout the entire house! It is uncommon to find this many upgrades at this price point! There is a full length concrete storm shelter under the front porch accessed via the crawlspace door for added piece of mind. The 4.82 acre lot features level areas ready to build your barn or detached workshop, a nice flat backyard area ready to install your pool, and plenty of room to fence off for your 4 legged friends of any kind! Located only 6 minutes (4.3 miles) from I-64, this location gives you the country life you want while still being easily accessed from Winchester or Mt Sterling and provides an easy 25 minute drive to Lexington. As an option, you can take the beautiful scenic drive out Ecton Rd to access the home if you prefer. Property is under a contingent contract with a 72 hour kick out clause.

1477 Sewell Shop 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

$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

$1,500,000

3 Beds ⋅ 2 Baths ⋅ 26025528 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, Winchester

$390,000

4 Beds ⋅ 1 Baths ⋅ 26025300 MLS

7353 Ironworks Road and 3015 Pilot View Road are deeded separate but being sold together. 7353 Ironworks includes the house and barn and 3.348 acres. 3015 Pilot View is the adjacent lot and has 3.38 acres. Total acreage is 6.728. There are 2 bedrooms upstairs that need cosmetic work. The historic barn is large, has electric and needs some repair. There is plenty of space to build your dream home. Plenty of road frontage on Ironworks and Pilot View. The lots are mostly level, some sloping and mainly cleared. Lots of things to like about this property! Transform this wonderful old farmhouse or plenty of room to build your dream home. Selling as is, Inspections welcome.

7353 Ironworks Rd, 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

$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

$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

$629,000

5 Beds ⋅ 4 Baths ⋅ 26023607 MLS

10/25 open house will be rescheduled! Space, craftsmanship, and versatility come together in this stunning all-brick 1.5-story home with a finished basement, located in the desirable Mallard Place subdivision! Designed to maximize every square foot, this home offers three levels of comfortable and flexible living space. The main level welcomes you with beautiful hardwood floors, vaulted ceilings, and a cozy gas fireplace. The spacious primary suite features an en suite bath, while two additional bedrooms are connected by a convenient Jack-and-Jill bathroom. A formal dining room and eat-in kitchen provide plenty of space for everyday living and entertaining. The basement is made for gathering, featuring an entertainment area complete with a bar, along with a bonus room and plenty of storage. Upstairs, you'll find even more flexible space, including a loft-style bedroom, two additional bonus rooms that could be used as bedrooms, a family room, and additional attic storage. Step outside to enjoy the backyard retreat, complete with an in-ground pool—perfect for relaxing and entertaining! With so much space and so many possibilities inside and out, this home is one you truly need to see in person. Schedule your private showing today!

104 Teal Ln, 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

$1,400,000

4 Beds ⋅ 4 Baths ⋅ 26023265 MLS

Magnificent Home sitting on 2.446 Acres, Fantastic Location --Great Views on this 4 Bedroom, 4 Bath Brick Home with over 5,600 Sq. Ft. of Living space. This has a Huge Primary Bedroom with walk in Shower, 2 closets, Large Formal Dining Rm,--Stone Fireplace, Large Sun room with lots of Windows, Another Primary Bedroom upstairs w/Full Bath, Large Finished Basement, with Mother's in Law Quarters. Don't Miss this Great opportunity--Come se this huge Magnificent Home-- Buyer to measure for exact sq.ft of Home Home is vacant and nearing Completion.

1400 Craig Xing, Winchester

$269,500

4 Beds ⋅ 2 Baths ⋅ 26023223 MLS

Seller offering a 2/1 rate buydown with an acceptable offer! 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

$219,900

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

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